ORGANIC LIGHT-EMITTING DEVICE AND ELECTRONIC APPARATUS INCLUDING THE SAME

Abstract

An organic light-emitting device including a first electrode; a second electrode facing the first electrode; an interlayer arranged between the first electrode and the second electrode, wherein the interlayer comprises an emission layer; a first compound represented by Formula 1; and a second compound represented by Formula 2:

##STR00001##

wherein ring CY.sub.11 to ring CY.sub.14, ring CY.sub.23, and ring CY.sub.24 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group; E.sub.1 is a group represented by Formula 1A; k1 is an integer from 1 to 5; n11 is an integer from 1 to 3; n12 is an integer from 0 to 3; X.sub.21 is N or C(R.sub.21a), X.sub.22 is N or C(R.sub.22a), X.sub.23 is N or C(R.sub.23a), and at least one of X.sub.21 to X.sub.23 is N; and the remaining substituents are as defined herein.

Claims

1. An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; an interlayer arranged between the first electrode and the second electrode, wherein the interlayer comprises an emission layer; a first compound represented by Formula 1; and a second compound represented by Formula 2: ##STR00262## wherein, in Formulae 1, 1A, and 2, ring CY.sub.11 to ring CY.sub.14, ring CY.sub.23, and ring CY.sub.24 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, E.sub.1 is a group represented by Formula 1 A, k1 is an integer from 1 to 5, n11 is an integer from 1 to 3, n12 is an integer from 0 to 3, X.sub.21 is N or C(R.sub.21a), X.sub.22 is N or C(R.sub.22a), X.sub.23 is N or C(R.sub.23a), and at least one of X.sub.21 to X.sub.23 is N, L.sub.21 and L.sub.22 are each independently a single bond, a substituted or unsubstituted C.sub.3-C.sub.60 carbocyclic group, or a substituted or unsubstituted C.sub.1-C.sub.60 heterocyclic group, n21 and n22 are each independently an integer from 1 to 5, R.sub.11 to R.sub.17, R.sub.21 to R.sub.24, R.sub.21a, R.sub.22a, and R.sub.23a 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, 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), wherein R.sub.17 is not a substituted or unsubstituted carbazolyl group, the first compound represented by Formula 1 comprises at least one deuterium, b15 and b16 are each independently an integer from 0 to 4, b17 is an integer from 0 to 5, b11 to b14 and b21 to b24 are each independently an integer from 1 to 10, * indicates a binding site to a neighboring atom, 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.3-C.sub.60 carbocyclic group, the substituted C.sub.1-C.sub.60 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —Ge(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.14)(Q.sub.15), —B(Q.sub.16)(Q.sub.17), —P(Q.sub.18)(Q.sub.19), —P(═O)(Q.sub.18)(Q.sub.19), or a combination thereof; a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.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.39), 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 organic light-emitting device of claim 1, wherein ring CY.sub.11 to ring CY.sub.14, ring CY.sub.23, and ring CY.sub.24 are each independently a benzene group, a naphthalene group, or a pyridine group.

3. The organic light-emitting device of claim 1, wherein the first compound represented by Formula 1 satisfies at least one of Conditions 1 to 7: Condition 1 at least one of R.sub.11 is deuterium; Condition 2 at least one of R.sub.12 is deuterium; Condition 3 at least one of R.sub.13 is deuterium; Condition 4 at least one of R.sub.14 is deuterium; Condition 5 at least one of R.sub.15 is deuterium; Condition 6 at least one of R.sub.16 is deuterium; or Condition 7 at least one of R.sub.17 is deuterium.

4. The organic light-emitting device of claim 1, wherein a moiety represented by: ##STR00263## in Formula 1 is a group represented by one of Formulae 1-1-a to 1-20-a: ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## wherein, in Formulae 1-1-a to 1-20-a, R.sub.11 to R.sub.14 are each as described in claim 1, b11 to b14 are each as described in claim 1, b13a and b13b are each as described in connection with b13 in claim 1, b14a and b14b are each as described in connection with b14 in claim 1, and * indicates a binding site to a neighboring atom.

5. The organic light-emitting device of claim 1, wherein a moiety represented by: ##STR00270## in Formula 1 is a group represented by one of Formulae 1-1-b to 1-17-b: ##STR00271## ##STR00272## wherein, in Formulae 1-1-b to 1-17-b, R.sub.15 is as described in claim 1, E.sub.11 to E.sub.13 are each as described in connection with E.sub.1 in claim 1, d12 is an integer from 0 to 2, d13 is an integer from 0 to 3, d14 is an integer from 0 to 4, and * indicates a binding site to a neighboring atom.

6. The organic light-emitting device of claim 1, wherein a group represented by Formula 1A is a group represented by one of Formulae 1A-1 to 1A-13: ##STR00273## ##STR00274## ##STR00275## wherein, in Formulae 1A-1 to 1A-13, R.sub.16, R.sub.17, b16, and b17 are each as described in claim 1, b16a and b16b are each as described in connection with b16, and * indicates a binding site to a neighboring atom.

7. The organic light-emitting device of claim 1, wherein X.sub.21 to X.sub.23 are each N.

8. The organic light-emitting device of claim 1, wherein L.sub.21 and L.sub.22 are each independently: a single bond; or a group represented by one of Formulae L-1 to L-12: ##STR00276## ##STR00277## wherein, in Formulae L-1 to L-12, Z.sub.21 and Z.sub.22 are each independently as described in connection with R.sub.21 in claim 1, d21 and d22 are each independently an integer from 0 to 4, d23 is an integer from 0 to 3, and * and *′ each indicate a binding site to a neighboring atom.

9. The organic light-emitting device of claim 1, wherein R.sub.21 and R.sub.22 are each independently a C.sub.6-C.sub.60 aryl group unsubstituted or substituted with at least one R.sub.10a, a group represented by Formula 2A, or a group represented by Formula 2B, and R.sub.10a is as described in connection with R.sub.23 in claim 1: ##STR00278## wherein, in Formulae 2A and 2B, Z.sub.23 to Z.sub.27 are each as described in connection with R.sub.23 in claim 1, d24 and d25 are each independently an integer from 1 to 4, d26 to d30 are each independently an integer from 1 to 5, L.sub.23 is as described in connection with L.sub.21 in claim 1, n23 is an integer from 1 to 5, m23 is an integer from 0 to 3, and * indicates a binding site to a neighboring atom.

10. The organic light-emitting device of claim 1, wherein the first compound is at least one of Compounds H1 to H15, wherein at least one hydrogen is substituted with deuterium, and the second compound is at least one of Compounds E.sub.1 to E.sub.40: ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296##

11. The organic light-emitting device of claim 1, wherein the first electrode is an anode, the second electrode is a cathode, the interlayer further comprises a hole transport region 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.

12. The organic light-emitting device of claim 1, wherein the emission layer comprises the first compound and the second compound.

13. The organic light-emitting device of claim 1, wherein the emission layer further comprises a third compound, a fourth compound, or a combination thereof, the third compound comprises a transition metal, and the fourth compound has a difference between a triplet energy level and a singlet energy level of 0.4 electron Volts or less.

14. The organic light-emitting device of claim 13, wherein the third compound comprises an organometallic compound represented by Formula 3 or 5: ##STR00297## wherein, in Formula 3, M.sub.31 is a transition metal, X.sub.31 to X.sub.34 are each independently C or N, two of a bond between X.sub.31 and M.sub.31, a bond between X.sub.32 and M.sub.31, a bond between X.sub.33 and M.sub.31, and a bond between X.sub.34 and M.sub.31 are each a coordinate bond, and the other two are each a covalent bond, ring CY.sub.31 to ring CY.sub.34 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, L.sub.31 is a single bond, a double bond, *—N(R.sub.35a)—*′, *—B(R.sub.35a)—*′, *—P(R.sub.35a)—*′, *—C(R.sub.35a)(R.sub.35b)—*′, *—Si(R.sub.35a)(R.sub.35b)—*′, *—Ge(R.sub.35a)(R.sub.35b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, *—C(R.sub.35a)═*′, *═C(R.sub.35a)—*′, *—C(R.sub.35a)═C(R.sub.35b)—*′, *—C(═S)—*′, *—C≡C—*′, a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, L.sub.32 is a single bond, a double bond, *—N(R.sub.36a)—*′, *—B(R.sub.36a)—*′, *—P(R.sub.36a)—*′, *—C(R.sub.36a)(R.sub.36b)—*′, *—Si(R.sub.36a)(R.sub.36b)—*′, *—Ge(R.sub.36a)(R.sub.36b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, *—C(R.sub.36a)═*′, *═C(R.sub.36a)—*′, *—C(R.sub.36a)═C(R.sub.36b)—*′, *—C(═S)—*′, *—C≡C—*′, a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, L.sub.33 is a single bond, a double bond, *—N(R.sub.37a)—*′, *—B(R.sub.37a)—*′, *—P(R.sub.37a)—*′, *—C(R.sub.37a)(R.sub.37b)—*′, *—Si(R.sub.37a)(R.sub.37b)—*′, *—Ge(R.sub.37a)(R.sub.37b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, *—C(R.sub.37a)═*′, *═C(R.sub.37a)—*′, *—C(R.sub.37a)═C(R.sub.37b)—*′, *—C(═S)—*′, *—C≡C—*′, a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, L.sub.34 is a single bond, a double bond, *—N(R.sub.38a)—*′, *—B(R.sub.38a)—*′, *—P(R.sub.38a)—*′, *—C(R.sub.38a)(R.sub.38b)—*′, *—Si(R.sub.38a)(R.sub.38b)—*′, *—Ge(R.sub.38a)(R.sub.38b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, *—C(R.sub.38a)═*′, *═C(R.sub.38a)—*′, *—C(R.sub.38a)═C(R.sub.38b)—*′, *—C(═S)—*′, *—C≡C—*′, a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, n31 to n34 are each independently an integer from 0 to 5, and three or more of n31 to n34 are each independently an integer from 1 to 5, R.sub.31 to R.sub.34, R.sub.35a, R.sub.35b, R.sub.36a, R.sub.36b, R.sub.37a, R.sub.37b, R.sub.38a, and R.sub.38b 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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.1)(Q.sub.2), —Si(Q.sub.3)(Q.sub.4)(Q.sub.5), —Ge(Q.sub.3)(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), b31 to b34 are each independently an integer from 0 to 20, two or more of R.sub.31 are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, two or more of R.sub.32 are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, two or more of R.sub.33 are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, two or more of R.sub.34 are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, two or more of R.sub.31 to R.sub.34, R.sub.35a, R.sub.35b, R.sub.36a, R.sub.36b, R.sub.37a, R.sub.37b, R.sub.38a, and R.sub.38b are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, R.sub.10a is as described in connection with R.sub.31, and * and *′ each indicate a binding site to a neighboring atom, wherein, in Formula 5, M.sub.51 is a transition metal, L.sub.51 is a ligand represented by Formula 5A, and L.sub.52 is a ligand represented by Formula 5B: ##STR00298## wherein, in Formulae 5, 5A, and 5B, n51 is 1, 2 or 3, n52 is 0, 1, or 2, Y.sub.51 to Y.sub.54 are each independently C or N, ring CY.sub.51 to ring CY.sub.54 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, R.sub.51 to R.sub.54 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.7-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, —N(Q.sub.1)(Q.sub.2), —Si(Q.sub.3)(Q.sub.4)(Q.sub.5), —Ge(Q.sub.3)(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), b51 to b54 are each independently an integer from 1 to 20, * and *′ each indicates a binding site to M.sub.51, a substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.1-C.sub.60 alkylthio group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.7-C.sub.60 alkyl aryl group, the substituted C.sub.7-C.sub.60 aryl alkyl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted C.sub.2-C.sub.60 alkyl heteroaryl group, the substituted C.sub.2-C.sub.60 heteroaryl alkyl group, the substituted C.sub.1-C.sub.60 heteroaryloxy group, the substituted C.sub.1-C.sub.60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.11)(Q.sub.12), —Si(Q.sub.13)(Q.sub.14)(Q.sub.15), —Ge(Q.sub.13)(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, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.1-C.sub.60 alkylthio group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.21)(Q.sub.22), —Si(Q.sub.23)(Q.sub.24)(Q.sub.25), —Ge(Q.sub.23)(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; —N(Q.sub.31)(Q.sub.32), —Si(Q.sub.33)(Q.sub.34)(Q.sub.35), —Ge(Q.sub.33)(Q.sub.34)(Q.sub.35), —B(Q.sub.36)(Q.sub.37), —P(Q.sub.38)(Q.sub.39), or —P(═O)(Q.sub.38)(Q.sub.39); or a combination thereof, 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.

15. The organic light-emitting device of claim 14, wherein n34 is 0, X.sub.31 is C, and a bond between X.sub.31 and M.sub.31 is a coordinate bond.

16. The organic light-emitting device of claim 14, wherein, in Formula 5, M.sub.51 is Ir, and a sum of n51 and n52 is 3; or M.sub.51 is Pt, and the sum of n51 and n52 is 2.

17. The organic light-emitting device of claim 13, wherein the third compound is at least one of Compounds P1 to P52: ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313##

18. The organic light-emitting device of claim 13, wherein the fourth compound comprises a compound represented by Formula 4: ##STR00314## wherein, in Formula 4, Z is B or N, ring CY.sub.41 to ring CY.sub.43 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, L.sub.41 is *—N(R.sub.44)—*′, *—B(R.sub.44)—*′, *—P(R.sub.44)—*′, *—C(R.sub.44)(R.sub.45)—*′, *—Si(R.sub.44)(R.sub.45)—*′, * Ge(R.sub.44)(R.sub.45)—*′, *—O—*′, *—S—*′, *—Se—*′, *—C(═O)—*′, or *—S(═O).sub.2—*′, L.sub.42 is *—N(R.sub.46)—*′, *—B(R.sub.46)—*′, *—P(R.sub.46)—*′, *—C(R.sub.46)(R.sub.47)—*′, *—Si(R.sub.46)(R.sub.47)—*′, *—Ge(R.sub.46)(R.sub.47)—*′, *—O—*′, *—S—*′, *—Se—*′, *—C(═O)—*′, or *—S(═O).sub.2—*′, L.sub.43 is *—N(R.sub.48)—*′, *—B(R.sub.48)—*′, *—P(R.sub.48)—*′, *—C(R.sub.48)(R.sub.49)—*′, *—Si(R.sub.48)(R.sub.49)—*′, * Ge(R.sub.48)(R.sub.49)—*′, *—O—*′, *—S—*′, *—Se—*′, *—C(═O)—*′, or *—S(═O).sub.2—*′, n41 to n43 are each independently 0 or 1, when n41 is 0, L.sub.41 is not present, when n42 is 0, L.sub.42 is not present, and when n43 is 0, L.sub.43 is not present, R.sub.41 to R.sub.49 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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.1)(Q.sub.2), —Si(Q.sub.3)(Q.sub.4)(Q.sub.5), —Ge(Q.sub.3)(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), b41 to b43 are each independently an integer from 1 to 20, two or more of R.sub.41 are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10b, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10b, two or more of R.sub.42 are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10b, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10b, two or more of R.sub.43 are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10b, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10b, two or more of R.sub.41 to R.sub.49 are optionally bonded to each other to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10b, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10b, R.sub.10b is as described in connection with R.sub.41, * and *′ each indicates a binding site to a neighboring atom, a substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.1-C.sub.60 alkylthio group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.7-C.sub.60 alkyl aryl group, the substituted C.sub.7-C.sub.60 aryl alkyl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted C.sub.2-C.sub.60 alkyl heteroaryl group, the substituted C.sub.2-C.sub.60 heteroaryl alkyl group, the substituted C.sub.1-C.sub.60 heteroaryloxy group, the substituted C.sub.1-C.sub.60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.11)(Q.sub.12), —Si(Q.sub.13)(Q.sub.14)(Q.sub.15), —Ge(Q.sub.13)(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, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.1-C.sub.60 alkylthio group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.21)(Q.sub.22), —Si(Q.sub.23)(Q.sub.24)(Q.sub.25), —Ge(Q.sub.23)(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; —N(Q.sub.31)(Q.sub.32), —Si(Q.sub.33)(Q.sub.34)(Q.sub.35), —Ge(Q.sub.33)(Q.sub.34)(Q.sub.35), —B(Q.sub.36)(Q.sub.37), —P(Q.sub.38)(Q.sub.39), or —P(═O)(Q.sub.38)(Q.sub.39); or a combination thereof, 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 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.

19. The organic light-emitting device of claim 13, wherein the fourth compound is at least one of Compounds D1 to D30: ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323##

20. An electronic apparatus, comprising the organic light-emitting device of claim 1.

Description

DESCRIPTION OF FIGURE

[0349] The FIGURE is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to one or more embodiments will be described in further detail in connection with the FIGURE, but embodiments are not limited thereto. The organic light-emitting device 10 includes a first electrode 11, an interlayer 15, and a second electrode 19, which are sequentially stacked in the stated order.

[0350] A substrate may be additionally arranged under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water repellency.

[0351] The first electrode 11 may be produced by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. 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 for easy 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).

[0352] The first electrode 11 may have a single-layer structure or a multi-layer structure including multiple layers. For example, the first electrode 11 may have a three-layer structure of ITO/Ag/ITO, but the structure of the first electrode 11 is not limited thereto.

[0353] The interlayer 15 may be arranged on the first electrode 11.

[0354] The interlayer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0355] The hole transport region may be arranged between the first electrode 11 and the emission layer.

[0356] 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.

[0357] The hole transport region may include only either a hole injection layer, or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, constituting layers may sequentially be stacked in the stated order from the first electrode 11.

[0358] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition, but embodiments are not limited thereto.

[0359] 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 of about 100° C. to about 500° C., a vacuum pressure of about 10.sup.−8 torr to about 10.sup.−3 torr, and a deposition rate of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec. However, the deposition conditions are not limited thereto.

[0360] When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment may be performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0361] The conditions for forming the hole transport layer and the electron blocking layer may be similar to or the same as the conditions for forming the hole injection layer.

[0362] 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, but embodiments are not limited thereto:

##STR00207## ##STR00208## ##STR00209##

[0363] In Formula 201, Ar.sub.101 and Ar.sub.102 may each independently be: [0364] 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 [0365] 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.

[0366] In Formula 201, xa and xb may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

[0367] 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: [0368] hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, 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; [0369] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, or a C.sub.1-C.sub.10 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a combination thereof; [0370] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; or [0371] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a C.sub.1-C.sub.10 alkylthio group, or a combination thereof, but embodiments are not limited thereto.

[0372] In Formula 201, R.sub.109 may be: [0373] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group; or [0374] 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.1-C.sub.20 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.

[0375] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:

##STR00210##

wherein, in Formula 201A, R.sub.101, R.sub.111, R.sub.112, and R.sub.109 may each be as described herein.

[0376] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of Compounds HT1 to HT20, but embodiments are not limited thereto:

##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218##

[0377] A thickness of the hole transport region may be about 100 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 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 about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. Without wishing to be bound to theory, 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.

[0378] 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.

[0379] The charge-generation material may be, for example, a p-dopant. The p-dopant may be at least one of a quinone derivative, a metal oxide, or a cyano group-containing compound, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant may include a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ), or the like; a metal oxide, such as a tungsten oxide, a molybdenum oxide, or the like; or a cyano group-containing compound, such as Compounds HT-D1 or F12, but embodiments are not limited thereto:

##STR00219##

[0380] The hole transport region may include a buffer layer.

[0381] 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 the organic light-emitting device may be improved.

[0382] Then, the emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer, although the deposition or coating conditions may vary according to a material that is used to form the emission layer.

[0383] Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above, and materials for a host, to be explained later. However, the material for the electron blocking layer is not limited thereto.

[0384] The emission layer may include a host and a dopant.

[0385] For example, the host may include the first compound and the second compound.

[0386] For example, the dopant may include a phosphorescent dopant, a fluorescent dopant, or a combination thereof, the phosphorescent dopant may include the third compound, and the fluorescent dopant may include the fourth compound, but embodiments are not limited thereto.

[0387] In the emission layer, an amount of the dopant may be, based on weight, in a range of about 0.1 parts by weight to about 20 parts by weight per 100 parts by weight of the emission layer.

[0388] In one or more embodiments, when the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.

[0389] Next, an electron transport region may be arranged on the emission layer.

[0390] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0391] 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-layer structure or a multi-layer structure including two or more different materials.

[0392] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

[0393] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), but embodiments are not limited thereto:

##STR00220##

[0394] A thickness of the hole blocking layer may be about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. Without wishing to be bound to theory, when the thickness of the hole blocking layer is within the ranges above, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

[0395] The electron transport layer may further include, for example, at least one of BCP, Bphen, tris(8-hydroxy-quinolinato)aluminum (Alq3), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), but embodiments are not limited thereto:

##STR00221##

[0396] In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments are not limited thereto:

##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230##

[0397] A thickness of the electron transport layer may be about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Without wishing to be bound to theory, when the thickness of the electron transport layer is within the ranges above, the electron transport layer may have satisfactory electron transporting characteristics without a substantial increase in driving voltage.

[0398] The electron transport layer may include a metal-containing material in addition to the material as described herein.

[0399] The metal-containing material may include a Li complex. The Li complex may include, for example, at least one of Compound ET-D1 (lithium 8-hydroxyquinolate, LiQ) or ET-D2, but embodiments are not limited thereto:

##STR00231##

[0400] The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.

[0401] The electron injection layer may include LiF, NaCl, CsF, Li.sub.2O, BaO, or a combination thereof.

[0402] A thickness of the electron injection layer may be about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. Without wishing to be bound to theory, when the thickness of the electron injection layer is within the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

[0403] The second electrode 19 is arranged on the interlayer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. In one or more embodiments, the material for forming the second electrode 19 may be Li, Mg, Al, Ag, Al—Li, Ca, Mg—In, Mg—Ag, or the like. 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.

[0404] Hereinbefore, the organic light-emitting device has been described with reference to the FIGURE, but embodiments are not limited thereto.

[0405] The term “C.sub.1-C.sub.60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, or 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.

[0406] 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 non-limiting examples thereof include a methoxy group, an ethoxy group, an isopropyloxy group, or the like.

[0407] 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 non-limiting examples thereof include an ethenyl group, a propenyl group, a butenyl group, or 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.

[0408] 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 non-limiting examples thereof include an ethynyl group, a propynyl group, or 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.

[0409] The term “C.sub.3-C.sub.10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or 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.

[0410] 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, S, Se, Ge, and B as a ring-forming atom, and 1 to 10 carbon atoms as ring-forming atom(s), and non-limiting examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, or 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.

[0411] The term “C.sub.3-C.sub.10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, or 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.

[0412] The term “C.sub.1-C.sub.10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms as ring-forming atom(s), and at least one double bond in its ring. Non-limiting examples of the C.sub.1-C.sub.10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, or the like. The term “C.sub.1-C.sub.10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C.sub.1-C.sub.10 heterocycloalkenyl group.

[0413] The term “C.sub.6-C.sub.60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic ring 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 ring system having 6 to 60 carbon atoms. Non-limiting examples of the C.sub.6-C.sub.60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, or 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 rings may be fused to each other.

[0414] 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.

[0415] The term “C.sub.1-C.sub.60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic ring system that has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and 1 to 60 carbon atoms as ring-forming atom(s). The term “C.sub.1-C.sub.60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic ring system that has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and 1 to 60 carbon atoms as ring-forming atom(s). Non-limiting 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, or the like. When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60 heteroarylene group each includes two or more rings, the rings may be fused to each other.

[0416] 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.

[0417] The term “C.sub.6-C.sub.60 aryloxy group” as used herein indicates —OA.sub.102 (wherein A.sub.102 is a C.sub.6-C.sub.60 aryl group), and the term “C.sub.6-C.sub.60 arylthio group” as used herein indicates —SA.sub.103 (wherein A.sub.103 is a C.sub.6-C.sub.60 aryl group).

[0418] The term “C.sub.1-C.sub.60 heteroaryloxy group” as used herein refers to —OA.sub.104 (wherein A.sub.104 is the C.sub.1-C.sub.60 heteroaryl group), and the term “C.sub.1-C.sub.60 heteroarylthio group” as used herein refers to —SA.sub.105 (wherein A.sub.105 is the C.sub.1-C.sub.60 heteroaryl group).

[0419] 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. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group or 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.

[0420] 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, S, Se, Ge, and B, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group or 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.

[0421] The term “C.sub.5-C.sub.30 carbocyclic group” as used herein refers to a saturated or unsaturated ring 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.

[0422] The term “C.sub.1-C.sub.30 heterocyclic group” as used herein refers to a saturated or unsaturated ring group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B, other than 1 to 30 carbon atoms as ring-forming atom(s). The C.sub.1-C.sub.30 heterocyclic group may be a monocyclic group or a polycyclic group.

[0423] 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.3-C.sub.60 carbocyclic group, the substituted C.sub.1-C.sub.60 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 may be: [0424] deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, or a C.sub.1-C.sub.60 alkylthio group; [0425] 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, —N(Q.sub.11)(Q.sub.12), —Si(Q.sub.13)(Q.sub.14)(Q.sub.15), —B(Q.sub.16)(Q.sub.17), —P(Q.sub.18)(Q.sub.19), —P(═O)(Q.sub.18)(Q.sub.19), or a combination thereof; [0426] 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; [0427] 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, —N(Q.sub.21)(Q.sub.22), —Si(Q.sub.23)(Q.sub.24)(Q.sub.25), —B(Q.sub.26)(Q.sub.27), —P(Q.sub.28)(Q.sub.29), —P(═O)(Q.sub.28)(Q.sub.29), or a combination thereof; or [0428] —N(Q.sub.31)(Q.sub.32), —Si(Q.sub.33)(Q.sub.34)(Q.sub.35), —B(Q.sub.36)(Q.sub.37), —P(Q.sub.38)(Q.sub.39), or —P(═O)(Q.sub.38)(Q.sub.39), and [0429] Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to Q.sub.29, and Q.sub.31 to Q.sub.39 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an 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.

[0430] Hereinafter, a compound and an organic light-emitting device according to exemplary embodiments are described in further detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto.

EXAMPLES

Synthesis Example 1. Synthesis of Compound 6

[0431] Compound 6 was synthesized according to the following reaction scheme:

##STR00232## ##STR00233##

Synthesis of Intermediate (1)

[0432] 1-bromo-3-iodobenzene (35 grams (g), 123.7 millimoles (mmol)), (phenyl-d5)boronic acid (15.3 g, 120.5 mmol), tetrakis(triphenylphosphine)palladium(0) (5.95 g, 5.15 mmol), and sodium bicarbonate (21.6 g, 257 mmol) were mixed with toluene (400 milliliters (mL)), ethanol (100 mL), and deionized (DI) water (100 mL), and the mixed solution was heated at 120° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous magnesium sulfate (MgSO.sub.4), concentrated under reduced pressure, and then a product was purified by silica column chromatography, to synthesize Intermediate (1) (28.3 g, 118.8 mmol, yield of 96%). The product was identified by liquid chromatography mass spectrometry (LC-MS).

[0433] LC-MS (calculated: 237.02, found (M+1): m/z (mass-to-charge ratio)=238.04).

Synthesis of Intermediate (2)

[0434] Intermediate (1) (28.3 g, 118.8 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d.sub.8 (20.8 g, 118.8 mmol), sodium tert-butoxide (17.1 g, 177.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (5.4 g, 5.9 mmol), and tri-tert-butylphosphine (4.8 mL, 11.9 mmol) were added to toluene (550 mL), and heated at 130° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under a reduced pressure, and then a product was purified by silica column chromatography, to synthesize Intermediate (2) (19.5 g, 60.5 mmol, yield of 51%). The product was identified by LC-MS.

[0435] LC-MS (calculated: 332.22, found (M+1): m/z=333.25).

Synthesis of Intermediate (3)

[0436] Intermediate (2) (19.5 g, 60.5 mmol) and dimethylformamide (DMF) (600 mL) were stirred at 0° C. While maintaining the temperature of 0° C., N-bromosuccinimide (NBS) (10.2 g, 57.5 mmol) was added dropwise thereto, and then stirred at room temperature for 16 hours. After completion of the reaction, an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under reduced pressure, and then the product was purified by silica column chromatography, to synthesize Intermediate (3) (23.2 g, 56.6 mmol, yield of 94%). The product was identified by LC-MS.

[0437] LC-MS (calculated: 409.12, found (M+1): m/z=410.13).

Synthesis of Compound 6

[0438] Intermediate (3) (23.2 g, 56.6 mmol), (9H-carbazole-1,2,3,4,5,6,7,8-d.sub.8) (10.4 g, 59.4 mmol), sodium tert-butoxide (8.2 g, 85.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (2.1 g, 2.3 mmol), and tri-tert-butylphosphine (1.8 mL, 4.5 mmol) were added to toluene (280 mL), and the reaction mixture was heated at 130° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under a reduced pressure, and then the product was purified by silica column chromatography, to synthesize Compound 6 (19.5 g, 38.6 mmol, yield of 68%). The product was identified by LC-MS.

[0439] LC-MS (calculated: 504.32, found (M+1): m/z=505.33).

Synthesis Example 2. Synthesis of Compound 22

[0440] Compound 22 was synthesized according to the following reaction scheme:

##STR00234##

Synthesis of Intermediate (4)

[0441] Intermediate (4) was synthesized in a similar manner as in the synthesis of Intermediate (1) of Synthesis Example 1, except that 1-bromo-3-iodobenzene-2,4,5,6-d.sub.4 was used instead of 1-bromo-3-iodobenzene in synthesizing Intermediate (1) (yield of 70%). The product was identified by LC-MS.

[0442] LC-MS (calculated: 241.05, found (M+1): m/z=242.08).

Synthesis of Intermediate (5)

[0443] Intermediate (4) (11.8 g, 49.0 mmol), bis(pinacolato)diboron (13.7 g, 53.9 mmol), potassium acetate) (11.1 g, 113 mmol), and bis(triphenylphosphine)palladium(II) dichloride (1.6 g, 2.3 mmol) were added to toluene (220 mL), and the reaction mixture was heated at 130° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under reduced pressure, and then the product was purified by silica column chromatography, to synthesize Intermediate (5) (11.2 g, 38.7 mmol, yield of 79%). The product was identified by LC-MS.

[0444] LC-MS (calculated: 289.22, found (M+1): m/z=290.25).

Synthesis of Intermediate (6)

[0445] 1-bromo-3-iodobenzene) (17.3 g, 60.9 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d.sub.8 (8.9 g, 50.8 mmol), copper(I) iodide (4.8 g, 25.4 mmol), potassium phosphate (32.3 g, 152.4 mmol), and ethylenediamine (6.1 g, 101.6 mmol) were added to toluene (250 mL), and the reaction mixture was heated at 130° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under a reduced pressure, and then the product was purified by silica column chromatography, to synthesize Intermediate (6) (11.6 g, 35.2 mmol, yield of 70%). The product was identified by LC-MS.

[0446] LC-MS (calculated: 329.07, found (M+1): m/z=330.09).

Synthesis of Intermediate (7)

[0447] Intermediate (6) (11.6 g, 35.2 mmol), Intermediate (5) (11.2 g, 38.7 mmol), tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.4 mmol), and sodium bicarbonate (12.2 g, 88 mmol) were added to tetrahydrofuran (THF) (135 mL) and DI water (45 mL), and the reaction mixture was heated at 90° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under a reduced pressure, and then the product was purified by silica column chromatography, to synthesize Intermediate (7) (10.3 g, 25.0 mmol, yield of 71%). The product was identified by LC-MS.

[0448] LC-MS (calculated: 412.27, found (M+1): m/z=413.25).

##STR00235##

Synthesis of Intermediate (8)

[0449] Intermediate (8) was synthesized in a similar manner as in the synthesis of Intermediate (3) of Synthesis Example 1, except that Intermediate (7) was used instead of Intermediate (2) in synthesizing Intermediate (3) (yield of 88%). The product was identified by LC-MS.

[0450] LC-MS (calculated: 489.18, found (M+1): m/z=490.18).

Synthesis of Compound 22

[0451] Compound 22 was synthesized in a similar manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate (8) was used instead of Intermediate (3) in synthesizing Compound 6 (yield of 66%). The product was identified by LC-MS.

[0452] LC-MS (calculated: 584.38, found (M+1): m/z=585.39).

Synthesis Example 3. Synthesis of Compound 66

[0453] Compound 66 was synthesized according to the following reaction scheme:

##STR00236## ##STR00237##

Synthesis of Intermediate (9)

[0454] Intermediate (9) was synthesized in a similar manner as in the synthesis of Intermediate (1) of Synthesis Example 1, except that 1-bromo-2-fluorobenzene was used instead of 1-bromo-3-iodobenzene in synthesizing Intermediate (1) (yield of 45%). The product was identified by LC-MS.

[0455] LC-MS (calculated: 177.10, found (M+1): m/z=178.12).

Synthesis of Intermediate (10)

[0456] Intermediate (9) (8.2 g, 46.3 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d.sub.8 (8.76 g, 50.0 mmol), and cesium carbonate (24.4 g, 75.0 mmol) were added to DMF (100 mL), and the reaction mixture was heated and stirred at 165° C. for 20 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under reduced pressure, and then the product was purified by silica column chromatography, to synthesize Intermediate (10) (11.5 g, 34.7 mmol, yield of 75%). The product was identified by LC-MS.

[0457] LC-MS (calculated: 332.22, found (M+1): m/z=333.25).

Synthesis of Intermediate (11)

[0458] Intermediate (11) was synthesized in a similar manner as in the synthesis of Intermediate (3) of Synthesis Example 1, except that Intermediate (10) was used instead of Intermediate (2) in synthesizing Intermediate (3) (yield of 83%). The product was identified by LC-MS.

[0459] LC-MS (calculated: 409.12, found (M+1): m/z=410.13).

Synthesis of Compound 66

[0460] Compound 66 was synthesized in as similar manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate (11) was used instead of Intermediate (3) in synthesizing Compound 6 (yield of 63%). The product was identified by LC-MS.

[0461] LC-MS (calculated: 504.32, found (M+1): m/z=505.35).

Synthesis Example 4. Synthesis of Compound 110

[0462] Compound 110 was synthesized according to the following reaction scheme:

##STR00238##

Synthesis of Intermediate (15)

[0463] Intermediate (15) was synthesized in as similar manner as in the synthesis of Intermediate (3) of Synthesis Example 1, except that Compound 6 was used instead of Intermediate (2) in synthesizing Intermediate (3) (yield of 72%). The product was identified by LC-MS.

[0464] LC-MS (calculated: 581.22, found (M+1): m/z=582.23).

Synthesis of Compound 110

[0465] Compound 110 was synthesized in a similar manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate (15) was used instead of Intermediate (3) in synthesizing Compound 6 (yield of 52%). The product was identified by LC-MS.

[0466] LC-MS (calculated: 676.42, found (M+1): m/z=677.45).

Synthesis Example 5: Synthesis of Compound E1

[0467] Compound E1 was synthesized according to the following reaction scheme:

##STR00239##

[0468] 9,9′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (9.56 g, 21.45 mmol), triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (10.91 g, 23.59 mmol), tetrakis(triphenylphosphine)palladium(0) (2.48 g, 2.14 mmol), and K.sub.2CO.sub.3 (5.93 g, 42.90 mmol) were dissolved in THF/DI water (54 mL/22 mL). The mixed solution was heated and then stirred under reflux at 85° C. for 12 hours. After completion of the reaction, the temperature was allowed to lower to room temperature, and 1,000 mL of methanol was added to the reaction mixture. After filtering the resulting product, the filtrate was concentrated under a reduced pressure, and the product was purified by silica column chromatography, to obtain 8.50 g (yield of 53%) of Compound E1. The product was identified by LC-MS.

[0469] LC-MS (calculated: 745.27, found (M+1): m/z=746).

Synthesis Example 6: Synthesis of Compound E18

[0470] ##STR00240##

Synthesis of Intermediate A-1

[0471] 8.2 g of 9H-carbazole was dissolved in 80 mL of THF and cooled in a nitrogen atmosphere at −78° C. At −78° C., 24.4 mL of 2.5 molar (M) n-butyl lithium (n-BuLi) was slowly added dropwise thereto, and then stirred for 1 hour. 4.5 g of 2,4,6-trichloro-1,3,5-triazine was then added thereto and stirred for 4 hours after the temperature was raised to room temperature. DI water was slowly added dropwise to the reaction mixture at room temperature to terminate the reaction. An extraction process was performed thereon by using ethyl acetate, and an organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under a reduced pressure, and then the product was purified by silica column chromatography, so as to synthesize Intermediate A-1 (9.25 g, 20.7 mmol, yield of 85%). The product was identified by LC-MS.

[0472] LC-MS (calculated: 445.11, found (M+1): m/z=446.21).

##STR00241##

Synthesis of Intermediate B-1

[0473] 12.48 g of 9H-carbazole, 10 g of 1-bromo-2-fluorobenzene, and 30.51 g of potassium phosphate tribasic were added to 280 mL of DMF, and the contents were stirred at 165° C. for 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under a reduced pressure, and then the product was purified by silica column chromatography, to synthesize Intermediate B-1 (13.52 g, 41.97 mmol, yield of 73%). The product was identified by LC-MS.

[0474] LC-MS (calculated: 322.21, found (M+1): m/z=323.25).

Synthesis of Intermediate B-2

[0475] 13.52 g of Intermediate B-1, 13.91 g of bis(pinacolato)diboron, 1.71 g of bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl.sub.2), and 10.3 g of potassium acetate were added to 160 mL of xylene, and the reaction mixture was heated under reflux for 16 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using anhydrous MgSO.sub.4, concentrated under reduced pressure, and then the product purified through column chromatography, to obtain Intermediate B-2 (10.23 g, 27.7 mmol, yield of 66%). The product was identified by LC-MS.

[0476] LC-MS (calculated: 322.21, found (M+1): m/z=323.25).

##STR00242##

Synthesis of Compound E18

[0477] 7 g of Intermediate A-1, 10.14 g of Intermediate B-2, 1.1 g of Pd(PPh.sub.3).sub.4, and 6.55 g of potassium carbonate were added to 60 mL of THF and 30 mL of DI water, and then the reaction mixture was heated under reflux in a nitrogen atmosphere. Following the reaction for 18 hours, the reaction mixture was allowed to cool to room temperature, and an organic layer was separated therefrom to be purified through column chromatography, to obtain Compound E18 (9.75 g, 15.5 mmol, yield of 82%). The product was identified by LC-MS. LC-MS (calculated: 652.76, found (M+1): m/z=653.1873).

Synthesis Example 7: Synthesis of Compound E20

[0478] ##STR00243##

Synthesis of Intermediate D-1

[0479] Intermediate D-1 was synthesized in a similar manner as in the synthesis of Intermediate A-1, except that 9H-carbazole-1,2,3,4,5,6,7,8-d.sub.8 was used instead of 9H-carbazole in synthesizing Intermediate A-1 (8.23 g, 17.8 mmol). The product was identified by LC-MS.

[0480] LC-MS (calculated: 462.01, found (M+1): m/z=463.24).

##STR00244##

Synthesis of Intermediate E-1

[0481] Intermediate E-1 (7.2 g, 22.34 mmol) was synthesized in a similar manner as in the synthesis of Intermediate B-1, except that 9H-carbazole-1,2,3,4,5,6,7,8-d.sub.8 was used instead of 9H-carbazole in synthesizing Intermediate B-1 and 1-bromo-2-fluorobenzene-3,4,5,6-d.sub.4 was used instead of 1-bromo-2-fluorobenzene in synthesizing Intermediate E-1. The product was identified by LC-MS.

[0482] LC-MS [M].sup.+ (calculated: 322.21, found (M+1): m/z=323.46).

Synthesis of Intermediate E-2

[0483] Intermediate E-2 (6.85 g, 18.54 mmol) was synthesized in a similar manner as in the synthesis of Intermediate B-2, except that Intermediate E-1 was used instead of Intermediate B-1 in synthesizing Intermediate B-2. The product was identified by LC-MS.

[0484] LC-MS (calculated: 369.27, found (M+1): m/z=370.38).

##STR00245##

Synthesis of Compound E20

[0485] Compound E20 (9.21 g, 13.53 mmol) was synthesized in a similar manner as in the synthesis of Compound E18, except that Intermediate D-1 was used instead of Intermediate A-1 in synthesizing Intermediate E18 and Intermediate E-2 was used instead of Intermediate B-2 in synthesizing Intermediate E18. The product was identified by LC-MS.

[0486] LC-MS [M].sup.+ (calculated: 680.93, found (M+1): m/z=682.02).

Synthesis Example 8: Synthesis of Compound E40

[0487] ##STR00246##

Synthesis of Intermediate E40-1

[0488] 9H-carbazole-1,2,3,4,5,6,7,8-d.sub.8 (2 equivalents) was reacted with nBuLi at room temperature. After 15 minutes, cyanuric chloride (1 equivalent) was slowly added dropwise and reacted at 70° C. to synthesize Intermediate E40-1. The Intermediate E40-1 was confirmed by LC-MS.

[0489] LC-MS (calculated: 461.21, found (M+1): m/z=462.33).

##STR00247##

Synthesis of Intermediate E40-2

[0490] 1,3-dibromobenzene-2,4,5,6-d.sub.4 (1 equivalent) was reacted with nBuLi at −78° C. After 60 minutes, chlorotris(phenyl-d.sub.5)silane (1.2 equivalents) was slowly added dropwise thereto and reacted while the temperature was slowly raised to room temperature to synthesize Intermediate E40-2, The Intermediate E40-2 was confirmed by LC-MS.

[0491] LC-MS (calculated: 433.16, found (M+1): m/z=434.21).

Synthesis of Intermediate E40-3

[0492] The Intermediate E40-2 was reacted with nBuLi at −78° C. After 60 minutes, trimethyl borate was slowly added dropwise thereto and reacted while the temperature was slowly raised to room temperature to synthesize Intermediate E40-3. The Intermediate E40-3 was confirmed by LC-MS.

[0493] LC-MS (calculated: 399.26, found (M+1): m/z=400.10).

##STR00248##

Synthesis of Compound E40

[0494] 3.1 g of Intermediate E40-1, 3.2 g of Intermediate E40-3, 0.31 g of Pd(PPh.sub.3).sub.4, and 2.3 g of potassium carbonate were dissolved in 40 mL of toluene, 10 mL of ethanol, and 10 mL of DI water, and the reaction mixture was heated at reflux for 12 hours. After completion of the reaction, an extraction process was performed thereon by using ethyl acetate. An organic layer thus obtained was dried by using MgSO.sub.4, concentrated under reduced pressure, and then the product was purified by silica column chromatography, to synthesize Compound E40 (3.4 g, yield of 64%). The Compound E40 was identified by LC-MS.

[0495] LC-MS (calculated: 780.49, found (M+1): m/z=781.51).

Example 1-1

[0496] A glass substrate with a 1,500 Å-thick indium tin oxide (ITO) electrode (first electrode, anode) formed thereon was cleaned by ultrasonication in DI water. After the DI water ultrasonication, ultrasonic cleaning was performed with isopropyl alcohol, acetone, and methanol in order, and the glass substrate was dried and transferred to a plasma cleaner. The glass substrate was cleaned by using oxygen plasma for 5 minutes, and then transferred to a vacuum deposition apparatus.

[0497] Compound HT3 and Compound HT-D2 were co-deposited by vacuum on the ITO electrode on the glass substrate to form a hole injection layer having a thickness of 100 Å, and Compound HT3 was deposited by vacuum on the hole injection layer to form a hole transport layer having a thickness of 1,300 Å, and mCP was deposited on the hole transport layer by vacuum to form an electron blocking layer having a thickness of 100 Å to form a hole transport region.

[0498] On the hole transport region, the first compound, the second compound, and the emitter shown in Table 1 were co-deposited by vacuum (at a weight ratio of 57:30:13) to form an emission layer having a thickness of 400 Å.

[0499] BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, and Compound ET3 and LiQ were co-deposited by vacuum on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, and LiQ was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and an Al second electrode (cathode) having a thickness of 1,200 Å was formed on the electron injection layer, thereby completing the manufacture of an organic light-emitting device.

Examples 1-2 to 1-7 and Comparative Example 1-1

[0500] Organic light-emitting devices were manufactured in a similar manner as in Example 1-1, except that compounds shown in Table 1 were each used for forming the emission layer.

Example 2-1

[0501] A glass substrate with a 1,500 Å-thick indium tin oxide (ITO) electrode (first electrode, anode) formed thereon was cleaned by ultrasonication in DI water. After the DI water ultrasonication, ultrasonic cleaning was performed with isopropyl alcohol, acetone, and methanol in order, and the glass substrate was dried and transferred to a plasma cleaner. The glass substrate was cleaned by using oxygen plasma for 5 minutes, and then transferred to a vacuum deposition apparatus.

[0502] Compound HT3 and Compound HT-D2 were co-deposited by vacuum on the ITO electrode on the glass substrate to form a hole injection layer having a thickness of 100 Å, and Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,300 Å, and mCP was vacuum-deposited on the hole transport layer to form an electron blocking layer having a thickness of 100 Å to form a hole transport region.

[0503] On the hole transport region, the first compound, the second compound, the first emitter, and the second emitter shown in Table 2 were co-deposited by vacuum (at a weight ratio of 56:30.2:13:0.8) to form an emission layer having a thickness of 400 Å.

[0504] BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, and Compound ET3 and LiQ were co-deposited by vacuum on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, and LiQ was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and an Al second electrode (cathode) having a thickness of 1,200 Å was formed on the electron injection layer, thereby completing the manufacture of an organic light-emitting device.

##STR00249## ##STR00250##

Examples 2-2 to 2-5 and Comparative Example 2-1

[0505] Organic light-emitting devices were manufactured in a similar manner as in Example 2-1, except that compounds shown in Table 2 were each used for forming the emission layer.

Evaluation Example 1: Characterization of Organic Light-Emitting Device

[0506] Regarding the organic light-emitting devices of Examples and Comparative Examples, the lifespan (LT.sub.95, %) was measured, and the results thereof are shown in Tables 1 and 2. Here, as evaluation devices, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the lifespan (LT.sub.95) (at 1,000 candela per square meter (cd/m.sup.2)) was evaluated by measuring the time required to reach 95% of luminance compared to 100% of the initial luminance. Examples 1-1 to 1-7 were evaluated relative to Comparative Example 1-1, and Examples 2-1 to 2-5 were evaluated relative to Comparative Example 2-1.

TABLE-US-00001 TABLE 1 Emission layer Host compound LT.sub.95 First host Second host Emitter (%) Example 1-1 6 E1 P31 509 Example 1-2 6  E20 P31 595 Example 1-3 22 E1 P31 359 Example 1-4 66 E1 P31 359 Example 1-5 110 E1 P31 259 Example 1-6 110  E20 P31 196 Example 1-7 6  E40 P31 677 Comparative Z1 Z2 P31 100 Example 1-1

TABLE-US-00002 TABLE 2 Emission layer Host compound First Second LT.sub.95 First host Second host emitter emitter (%) Example 2-1 6 E1 P31 D3 316 Example 2-2 6  E20 P31 D3 494 Example 2-3 22 E1 P31 D3 318 Example 2-4 66 E1 P31 D3 249 Example 2-5 6  E40 P31 D3 562 Comparative Z1 Z2 P31 D3 100 Example 2-1 [00251]6 [00252]22 [00253]66 [00254]110 [00255]E1 [00256]E20 [00257]P31 [00258]D3 [00259]E40 [00260]Z [00261]Z2

[0507] Referring to Table 1, it was confirmed that the organic light-emitting devices of Examples 1-1 to 1-7 had long lifespan characteristics of up to 677% as compared to the organic light-emitting device of Comparative Example 1-1 (100%).

[0508] Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 2-1 to 2-5 had long lifespan characteristics of up to 562% as compared to the organic light-emitting device of Comparative Example 2-1 (100%).

[0509] The organic light-emitting device as provided herein including a first compound and a second compound in an emission layer may have long lifespan characteristics. Thus, by using the organic light-emitting device, a high-quality electronic apparatus may be provided.

[0510] It should be understood that exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other exemplary embodiments. While one or more exemplary embodiments have been described with reference to the FIGURE, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.