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

An organometallic compound represented by Formula 1:  M1(L1)n1(L2)n2  Formula 1          wherein, M1 is a transition metal, L1 is a ligand represented by Formula 1A, and L2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2,                  wherein X1 and X2 are each independently C or N, Y1 is O, S, Se, C(R5)(R6), or N(R7), X44 is N or C(R44), X45 is N or C(R45), X46 is N or C(R46), and X47 is N or C(R47), and the other substituent groups are as defined herein.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0116672, filed on Sep. 15, 2022, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the content of which is incorporated by reference herein in its entirety.

BACKGROUND

The disclosure relates to an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emissive devices, and have improved characteristics in terms of viewing angles, response time, brightness, driving voltage, and response speed. In addition, OLEDS can produce full-color images.

SUMMARY

Provided are an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.

Additional aspects will be set forth in part in the detailed description that follows and, in part, will be apparent from the detailed description, or may be learned by practice of the presented exemplary embodiments herein.

According to an aspect, an organometallic compound is represented by Formula 1

M1(L1)n1(L2)n2Formula 1wherein, in Formula 1,M1is a transition metal,L1is a ligand represented by Formula 1A,L2is a ligand represented by Formula 1B, andn1 and n2 are each independently 1 or 2,

wherein, in Formulae 1A and 1B,X1is C or N, and X2is C or N,ring CY1and ring CY2are each independently a C5-C30carbocyclic group or a C1-C30heterocyclic group,ring CY3is a 5-membered heterocyclic group, a 5-membered heterocyclic group to which a C5-C30carbocyclic group is condensed, or a 5-membered heterocyclic group to which a C1-C30heterocyclic group is condensed,ring CY4is a 5-membered carbocyclic group or a 5-membered heterocyclic group,Y1is O, S, Se, C(R5)(R6), or N(R7),X44is N or C(R44), X45is N or C(R45), X46is N or C(R46), and X47is N or C(R47),R1to R7and R44to R47are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 C1-C60alkyl group, a substituted or unsubstituted C2-C60alkenyl group, a substituted or unsubstituted C2-C60alkynyl group, a substituted or unsubstituted C1-C60alkoxy group, a substituted or unsubstituted C1-C60alkylthio group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C7-C60alkyl aryl group, a substituted or unsubstituted C7-C60aryl alkyl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted C2-C60alkyl heteroaryl group, a substituted or unsubstituted C2-C60heteroaryl alkyl group, a substituted or unsubstituted C1-C60heteroaryloxy group, a substituted or unsubstituted C1-C60heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), —P(Q8)(Q9), or —P(═O)(Q8)(Q9),two or more of a plurality of R1are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group,two or more of a plurality of R2are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group,one or more of R1and one or more of R2are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic grouptwo or more of a plurality of R3are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group,two or more of a plurality of R4are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group, andtwo or more of R44to R47are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group,one or more of R4and one of R44to R47are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group,b1 to b3 are each independently an integer from 1 to 10,b4 is an integer from 1 to 3,at least one substituent of the substituted C5-C30carbocyclic group, the substituted C1-C30heterocyclic group, the substituted C1-C60alkyl group, the substituted C2-C60alkenyl group, the substituted C2-C60alkynyl group, the substituted C1-C60alkoxy group, the substituted C1-C60alkylthio group, the substituted C3-C10cycloalkyl group, the substituted C1-C10heterocycloalkyl group, the substituted C3-C10cycloalkenyl group, the substituted C1-C10heterocycloalkenyl group, the substituted C6-C60aryl group, the substituted C7-C60alkyl aryl group, the substituted C7-C60aryl alkyl group, the substituted C6-C60aryloxy group, the substituted C6-C60arylthio group, the substituted C1-C60heteroaryl group, the substituted C2-C60alkyl heteroaryl group, the substituted C2-C60heteroaryl alkyl group, the substituted C1-C60heteroaryloxy group, the substituted C1-C60heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, or a C1-C60alkylthio group,a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, or a C1-C60alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C1cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C7-C60alkyl aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a C2-C60alkyl heteroaryl group, a C1-C60heteroaryloxy group, a C1-C60heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —Ge(Q11)(Q12)(Q13), —N(Q14)(Q15), —B(Q16)(Q17), —P(Q18)(Q19), —P(═O)(Q18)(Q19), or a combination thereof,a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C7-C60alkyl aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a C2-C60alkyl heteroaryl group, a C1-C60heteroaryloxy group, a C1-C60heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group,a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C7-C60alkyl aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a C2-C60alkyl heteroaryl group, a C1-C60heteroaryloxy group, a C1-C60heteroarylthio 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, —SF5, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C1-C60alkylthio group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C7-C60alkyl aryl group, a C7-C60aryl alkyl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a C2-C60alkyl heteroaryl group, a C2-C60heteroaryl alkyl group, a C1-C60heteroaryloxy group, a C1-C60heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —Ge(Q21)(Q22)(Q23), —N(Q24)(Q25), —B(Q26)(Q27), —P(Q28)(Q29), —P(═O)(Q28)(Q29), or a combination thereof, or—Si(Q31)(Q32)(Q33), —Ge(Q31)(Q32)(Q33), —N(Q34)(Q35), —B(Q36)(Q37), —P(Q38)(Q39), or —P(═O)(Q38)(Q39),wherein Q1to Q9, Q11to Q19, Q21to Q29, and Q31to Q39are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 C1-C60alkyl group, a substituted or unsubstituted C2-C60alkenyl group, a substituted or unsubstituted C2-C60alkynyl group, a substituted or unsubstituted C1-C60alkoxy group, a substituted or unsubstituted C1-C60alkylthio group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C7-C60alkyl aryl group, a substituted or unsubstituted C7-C60aryl alkyl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted C2-C60alkyl heteroaryl group, a substituted or unsubstituted C2-C60heteroaryl alkyl group, a substituted or unsubstituted C1-C60heteroaryloxy group, a substituted or unsubstituted C1-C60heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to another aspect, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer further includes at least one of the organometallic compounds.

The organometallic compound may be included in the emission layer of the organic layer, and the organometallic compound included in the emission layer may act as a dopant.

According to another aspect, an electronic apparatus includes the organic light-emitting device.

DETAILED DESCRIPTION

Hereinafter, a work function or a highest occupied molecular orbital (HOMO) energy level is expressed as an absolute value from a vacuum level. In addition, when the work function or the HOMO energy level is referred to be “deep,” “high,” or “large,” the work function or the HOMO energy level has a large absolute value based on “0 electron Volts (eV)” of the vacuum level, while when the work function or the HOMO energy level is referred to be “shallow,” “low,” or “small,” the work function or HOMO energy level has a small absolute value based on “0 eV” of the vacuum level.

According to an aspect, an organometallic compound is represented by Formula 1:

For example, M1may be a Period 1 transition metal of the Periodic Table of Elements, a Period 2 transition metal of the Periodic Table of Elements, or a Period 3 transition metal of the Periodic Table of Elements.

In one or more embodiments, M1may be iridium, platinum, osmium, or rhodium.

In one or more embodiments, M1may be iridium.

In Formula 1, n1 is 1 or 2, n2 is 1 or 2.

In one or more embodiments, a sum of n1 and n2 may be 2 or 3.

In one or more embodiments, M1may be iridium, and the sum of n1 and n2 may be 3.

In one or more embodiments, M1may be platinum, and the sum of n1 and n2 may be 2.

L1in Formula 1 is a ligand represented by Formula 1A:

In Formula 1A, X1is C or N, and X2is C or N.

In one or more embodiments, X1may be N, X2may be C.

The bond between M1and X1in Formula 1A may be a covalent bond or a coordination bond.

The bond between M1and X2in Formula 1A may be a covalent bond or a coordination bond.

In one or more embodiments, X1may be N, X2may be C, a bond between X1and M1may be a coordination bond, and a bond between X2and M1may be a covalent bond.

Ring CY1and ring CY2in Formula 1A are each independently a C5-C30carbocyclic group or a C1-C30heterocyclic group.

In one or more embodiments, ring CY1and ring CY2may each independently be a first ring, a second ring, a condensed ring group in which at least two first rings are condensed, a condensed ring group in which at least two second rings are condensed, or a condensed ring group in which at least one first ring is condensed with at least one second ring,the first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, andthe second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

In one or more embodiments, ring CY1may be a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

In one or more embodiments, ring CY2may be a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group.

In one or more embodiments, a moiety represented by

in Formula 1A may be a group represented by one of Formulae 1-1 to 1-16:

wherein, in Formulae 1-1 to 1-16,R11to R14may each independently be as described herein in connection with R1, provided that R11to R14may not be hydrogen,two or more of R11to R14may optionally be bonded to each other to form a C5-C30carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group unsubstituted or substituted with at least one R10a,R10ais as described herein in connection with R1,* indicates a binding site to M1, and*″ indicates a binding site to an adjacent atom.

In one or more embodiments, a moiety represented by

in Formula 1A may be a group represented by one of Formulae 2-1 to 2-16:

wherein, in Formulae 2-1 to 2-16,R21to R24may each independently be as described herein in connection with R2, provided that R21to R24may not be hydrogen,two or more of R21to R24may optionally be bonded to each other to form a C5-C30carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group unsubstituted or substituted with at least one R10a,R10ais as described herein in connection with R1,* indicates a binding site to M1, and*″ indicates a binding site to an adjacent atom.

L2in Formula 1 is a ligand represented by Formula 1B:

Ring CY3in Formula 1B is a 5-membered heterocyclic group, a 5-membered heterocyclic group to which a C5-C30carbocyclic group is condensed, or a 5-membered heterocyclic group to which a C1-C30heterocyclic group is condensed.

In one or more embodiments, ring CY3may be a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.

In one or more embodiments, a moiety represented by

in Formula 1B may be a group represented by one of Formulae 3-1 to 3-3:

wherein, in Formulae 3-1 to 3-3,X31may be C(R31a), C(R31a)(R31b), N, or N(R31a),X32may be C(R32a), C(R32a)(R32b), N, or N(R32a),X33may be C(R33a), C(R33a)(R33b), N, or N(R33a),ring CY34may be a C5-C30carbocyclic group or a C1-C30heterocyclic group,R31a, R31b, R32a, R32b, R33a, R33b, and R34may each independently be as described herein in connection with R3in the present specification,b34 may be an integer from 1 to 10,represents a single bond or a double bond,* indicates a binding site to M1, and*″ indicates a binding site to an adjacent atom.

In one or more embodiments, a moiety represented by

in Formula 1B may be a group represented by one of Formulae 3A-1 to 3A-16:

wherein, in Formulae 3A-1 to 3A-16,X31may be C(R31a)(R31b) or N(R31a),R31a, R31b, and R35to R38may each independently be as described herein in connection with R3,two or more of R35to R38may optionally be bonded to each other to form a C5-C30carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group unsubstituted or substituted with at least one R10a,R10ais as described herein in connection with R1,* indicates a binding site to M1, and*″ indicates a binding site to an adjacent atom.

Ring CY4in Formula 1B is a 5-membered carbocyclic group or a 5-membered heterocyclic group.

X44in Formula 1B is N or C(R44), X45is N or C(R45), X46is N or C(R46), and X47is N or C(R47), wherein R44to R47are each independently as defined herein.

In one or more embodiments, Formula 1B may be represented by one of Formulae 11B-1 and 1B-2:

wherein, in Formulae 1B-1 and 1B-2,ring CY3, R3, b3, Y1, and X44to X47are each as described herein,X41may be N, B, or C(R41a),X42may be O, S, Se, N(R42a), B(R42a), or C(R42a)(R42b),R41a, R42a, R42b, and R43may each independently be as described herein in connection with R4,* and *′ each indicates a binding site to M1.

wherein, in Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, “Ph” is a phenyl group, “TMS” is a trimethylsilyl group, and “TMG” is a trimethylgermyl group.

In Formula A, two or more of a plurality of R are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group,two or more of a plurality of R2are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group, andone or more of R1and one or more of R2are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group.

In Formula 1B, two or more of a plurality of R3are optionally be bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group,two or more of a plurality of R4are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group,two or more of R44to R47are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group, andone or more of R4and one of R44to R47are optionally bonded to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group.

In one or more embodiments, two or more of a plurality of R1; two or more of a plurality of R2; two or more of a plurality of R3; two or more of a plurality of R4; one or more of R1and one or more of R2; two or more of R44to R47; and/or one or more of R4and one of R44to R47may optionally be bonded together via a single bond, a double bond, or a first linking group to form a C5-C30carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group that is unsubstituted or substituted with at least one R10a(for example, a fluorene group, a xanthene group, an acridine group, or the like, each of which is unsubstituted or substituted with at least one R10a). R10ais as described herein in connection with R1.

The first linking group may be *—N(R8)—*′, *—B(R8)—*′, *—P(R8)—*′, *—C(R8)(R9)—*′, *—Si(R8)(R9)—*′, *—Ge(R8)(R9)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*, * —C(R8)═*′, *═C(R8)—*′, *—C(R8)═C(R9)—*′, *—C(═S)—*′, or *—C≡C—*′, R8and R9are each as described herein in connection with R1, and * and *′ each indicate a binding site to a neighboring atom.

In Formulae 1A and 1B, b1 to b3 are each independently an integer from 1 to 10, and b4 is an integer from 1 to 3.

In one or more embodiments, the organometallic compound may be represented by any one of Formulae 5-1 to 5-4:

wherein, in Formulae 5-1 to 5-4,M1, n1, n2, and Y1are as described herein,X11may be C(R11) or N, X12may be C(R12) or N, X13may be C(R13) or N, and X14may be C(R14) or N,X21may be C(R21) or N, X22may be C(R22) or N, X23may be C(R23) or N, and X24may be C(R24) or N,X35may be C(R35) or N, X36may be C(R36) or N, X37may be C(R37) or N, and X38may be C(R38) or N,X41may be N, B, or C(R41a),X42may be O, S, Se, N(R42a), B(R42a), or C(R42a)(R42b),R11to R14may each independently be as described herein in connection with R1,R21to R24may each independently be as described herein in connection with R2,R31to R33and R35to R38may each independently be as described herein in connection with R3,R41a, R42a, R42b, and R43may each independently be as described herein in connection with R4,R44to R47may each be as described herein,two or more of R11to R14may be optionally linked to each other to form a C5-C30carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group that is unsubstituted or substituted with at least one R10a,two or more of R21to R24may be optionally linked to each other to form a C5-C30carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group that is unsubstituted or substituted with at least one R10a,two or more of R31to R33and R35to R38may optionally be linked together to form a C5-C60carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group that is unsubstituted or substituted with at least one R10a, two or more of R44to R47may optionally be linked together to form a C5-C30carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group that is unsubstituted or substituted with at least one R10a, andR10ais as described herein in connection with R1.

In one or more embodiments, non-limiting examples of the “C5-C30carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30heterocyclic group unsubstituted or substituted with at least one R10a” include a benzene group, a naphthalene group, a cyclopentane group, a cyclopentadiene group, a cyclohexane group, a cycloheptane group, a bicyclo[2.2.1]heptane group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, or the like, each of which is unsubstituted or substituted with at least one R10a. R10ais as described herein in connection with R10. The C5-C30carbocyclic group and the C1-C30heterocyclic group are each as described herein.

In one or more embodiments, the organometallic compound may be represented by one of Compounds 1 to 66, but embodiments are not limited thereto:

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

The organometallic compound represented by Formula 1 satisfies the structure of Formula 1A described above and includes a ligand having a structure represented by Formula 1B. Due to this structure, the organometallic compound represented by Formula 1 has excellent luminescence characteristics and has such characteristics suitable for use as a luminescent material with high color purity by controlling the emission wavelength range.

In addition, the organometallic compound represented by Formula 1 has excellent electrical mobility, and thus, electronic devices including the organometallic compound, for example, organic light-emitting devices including the organometallic compound may show a low driving voltage, a high efficiency, and a long lifespan.

The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, singlet (S1) energy level, and triplet (T1) energy level of selected organometallic compound represented by Formula 1 were calculated using a density functional theory (DFT) method of the Gaussian 09 program with the molecular structure optimized at the B3LYP level, and results thereof are shown in Table 1. The energy levels are expressed in electron volts (eV).

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

In one or more embodiments, a maximum emission wavelength (emission peak wavelength, λmax) of an emission peak of an emission spectrum or electroluminescence spectrum of the organometallic compound may be about 490 nanometers (nm) to about 550 nm. For example, the maximum emission wavelength of an emission peak of an emission spectrum or electroluminescence spectrum of the organometallic compound may be about 500 nm to about 550 nm, about 490 nm to about 550 nm, about 510 nm to about 550 nm, or about 500 nm to about 540 nm.

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

Accordingly, since the organometallic compound represented by Formula 1 may be suitable for use as a dopant in an organic layer of an organic light-emitting device, for example, an emission layer of the organic layer, another aspect provides an organic light-emitting device including a first electrode, a second electrode, and an organic layer which is disposed between the first electrode and the second electrode, wherein the organic includes an emission layer, and wherein the organic layer further includes at least one of the organometallic compounds represented by Formula 1.

Since the organic light-emitting device has an organic layer including at least one of the organometallic compounds represented by Formula 1 as described herein, excellent characteristics may be obtained with respect to a driving voltage, a current efficiency, an external quantum efficiency, a roll-off ratio, and a lifespan. In addition, a FWHM of the emission peak of the EL spectrum may be relatively narrow.

The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, at least one of the organometallic compounds represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the at least one of the organometallic compounds represented by Formula 1 in the emission layer is less than an amount of the host in the emission layer, based on weight). In one or more embodiments, an amount of the host in the emission layer is greater than an amount of the at least one organometallic compound represented by Formula 1 in the emission layer, based on weight.

In one or more embodiments, the emission layer may emit a green light. For example, the emission layer may emit a green light having a maximum emission wavelength of about 490 nm to about 550 nm. For example, the emission layer may emit a green light having a maximum emission wavelength of about 500 nm to about 550 nm, about 490 nm to about 550 nm, about 510 nm to about 550 nm, or about 500 nm to about 540 nm.

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

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

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

In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, and the organic layer may further include a hole transport region located between the first electrode and the emission layer, and an electron transport region located between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron-blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole-blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

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

The FIGURE is a schematic cross-sectional view of an organic light-emitting device10according to one or more embodiments. Hereinafter, the structure and manufacturing method of the organic light-emitting device10according to one or more embodiments will be described in connection with the FIGURE, but embodiments are not limited thereto. The organic light-emitting device10includes a first electrode11, an organic layer15, and a second electrode19, which are sequentially stacked in the stated order.

A substrate may be additionally disposed under the first electrode11or on the second electrode19. The substrate may be a conventional substrate used in organic light-emitting devices, for example, 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.

The first electrode11may be produced by depositing or sputtering, onto the substrate, a material for forming the first electrode11. The first electrode11may be an anode. The material for forming the first electrode11may be selected from materials with a high work function for easier hole injection. The first electrode11may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode11may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode11may 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).

The first electrode11may have a single-layered structure or a multi-layered structure including a plurality of layers. For example, the first electrode11may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode11is not limited thereto.

The organic layer15may be located on the first electrode11.

The organic layer15may include a hole transport region, an emission layer, an electron transport region, or a combination thereof.

The hole transport region may be located between the first electrode11and the emission layer.

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.

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 the hole transport region may have a hole injection layer/hole transport layer/electron-blocking layer structure, wherein, for each structure, respective layers are sequentially stacked in the stated order from the first electrode11.

When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode11by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.

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 material. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8torr to about 10−3torr, and a deposition rate of about 0.01 angstroms per second (A/sec) to about 100 Å/sec. However, the deposition conditions are not limited thereto.

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 material. 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 about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

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.

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

R101to R108, R111to R119, and R121to R124in Formulae 201 and 202 may each independently be:hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 C1-C10alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, or the like), a C1-C10alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like), or a C1-C10alkylthio group;a C1-C10alkyl group, a C10-C10alkoxy group, or a C1-C10alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, 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;a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; ora 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, —SF5, 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 C1-C10alkyl group, a C1-C10alkoxy group, a C1-C10alkylthio group, or a combination thereof, but embodiments are not limited thereto.

According to one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:

R101, R111, R112, and R109in Formula 201A may each be as described herein.

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

The charge-generation material may be, for example, a p-dopant. The p-dopant may be 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 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-TCNQ), 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:

The hole transport region may include a buffer layer.

The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer to increase efficiency.

Then, an 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.

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 herein and/or materials for a host to be explained herein. However, the material for the electron-blocking layer is not limited thereto. For example, when the hole transport region includes an electron-blocking layer, a material for the electron-blocking layer may be mCP, which will be explained herein.

The emission layer may include a host and a dopant, and the dopant may include at least one of the organometallic compounds represented by Formula 1.

In one or more embodiments, the host may include a compound represented by Formula 301, but embodiments are not limited thereto:

Ar111and Ar112in Formula 301 may each independently be:a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; ora phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group, each substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof.

Ar113to Ar116in Formula 301 may each independently be:a C1-C10alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group; ora phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group, each substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof.g, h, i, and j in Formula 301 may each independently be an integer from 0 to 4, and g, h, i, and j may each independently be, for example, 0, 1, or 2.

Ar113to Ar116in Formula 301 may each independently be:a C1-C10alkyl group that is substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof;a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group;a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF5, 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 C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C1-C60alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, or a combination thereof; ora group represented by formula:

but embodiments are not limited thereto.

In one or more embodiments, the host may include a compound represented by Formula 302, but embodiments are not limited thereto:

Ar122to Ar125in Formula 302 may be as described herein in detail in connection with Ar113in Formula 301.

Ar126and Ar127in Formula 302 may each independently be a C1-C10alkyl group (for example, a methyl group, an ethyl group, a propyl group, or the like).

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

When the organic light-emitting device10is a full-color organic light-emitting device10, 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 a white light.

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

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

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

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

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.

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 (BAIq), but embodiments are not limited thereto:

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 these ranges, excellent hole characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (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:

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

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 range described above, the electron transport layer may have satisfactory electron transporting characteristics without a substantial increase in driving voltage.

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

The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode19thereinto.

The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.

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.

The second electrode19may be located on the organic layer15. The second electrode19may be a cathode. A material for forming the second electrode19may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (AI), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode19. 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 electrode19.

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

Another aspect provides a diagnostic composition including at least one of the organometallic compounds represented by Formula 1.

The organometallic compound represented by Formula 1 provides a high luminescent efficiency. Accordingly, a diagnostic composition including at least one of the organometallic compounds represented by Formula 1 may have a high diagnostic efficiency.

The diagnostic composition may be used in various applications, including a diagnosis kit, a diagnosis reagent, a biosensor, a biomarker, or the like, but embodiments are not limited thereto.

The term “C1-C60alkyl 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 “C1-C60alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60alkyl group.

The term “C2-C60alkenyl 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 C2-C60alkyl group, and non-limiting examples thereof include an ethenyl group, a propenyl group, a butenyl group, or the like. The term “C2-C60alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60alkenyl group.

The term “C1-C10heterocycloalkyl group” as used herein refers to a monovalent saturated cyclic group having at least one heteroatom selected from B, N, O, P, Ge, Se, Si, and S 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 “C1-C10heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10heterocycloalkyl group.

The term “C1-C10heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that has at least one heteroatom selected from B, N, O, P, Ge, Se, Si, and S 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 C1-C10heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, or the like. The term “C1-C10heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10heterocycloalkenyl group.

The term “C7-C60alkyl aryl group” as used herein refers to a C6-C60aryl group substituted with at least one C1-C60alkyl group. The term “C7-C60aryl alkyl group” as used herein refers to a C1-C60alkyl group substituted with at least one C6-C60aryl group.

The term “C2-C60alkyl heteroaryl group” as used herein refers to a C1-C60heteroaryl group substituted with at least one C1-C60alkyl group. The term “C2-C60heteroaryl alkyl group” as used herein refers to a C1-C60alkyl group substituted with at least one C1-C60heteroaryl group.

The term “C1-C60heteroaryloxy group” as used herein indicates —OA104(wherein A104is a C1-C60heteroaryl group), and the term “C1-C60heteroarylthio group” as used herein indicates —SA105(wherein A105is a C1-C60heteroaryl group).

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, Ge, Se, Si, and S, 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.

The term “C5-C30carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30carbocyclic group may be a monocyclic group or a polycyclic group.

The term “C1-C30heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, P, Ge, Se, Si, and S other than 1 to 30 carbon atoms as ring-forming atom(s). The C1-C30heterocyclic group may be a monocyclic group or a polycyclic group.

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

EXAMPLES

Synthesis Example 1: Synthesis of Compound 1

Synthesis of Compound 1A(1)

2-phenyl-pyridine (4.95 grams (g), 31.90 millimoles (mmol)) and iridium chloride trihydrate (5.00 g, 14.18 mmol) were mixed with 90 milliliters (mL) of ethoxyethanol and 30 mL of deionized (DI) water, then the resultant mixture was stirred and heated under reflux for 24 hours. Then, the temperature was allowed to lower to room temperature. The resultant solid was separated therefrom by filtration, washed sufficiently with water, methanol, and hexane, in this stated order, and then dried in a vacuum oven to obtain 6.91 g (yield of 81%) of Compound 1A(1).

Synthesis of Compound 1A

Compound 1A(1) (1.50 g, 1.24 mmol) and 45 mL of methylene chloride (MC) were combined. A mixture of silver trifluoromethanesulfonate (AgOTf) (0.67 g, 2.61 mmol) mixed with 15 mL of methanol was prepared separately, and then added thereto. Afterwards, the resultant reaction solution was stirred for 18 hours at room temperature while light was blocked with aluminum foil. The, the reaction contents were filtered through a Celite plug to remove a solid produced therein. The filtrate was then subjected to a reduced pressure to obtain a solid (Compound 1A) which was used in the next reaction without an additional purification process.

Synthesis of Compound 1B

Under a nitrogen environment, 2-bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo [d]imidazole (1.00 g, 2.31 mmol) and 2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxoborolane-2-yl)benzo[2,3]benzofuro[4,5-d]oxazole (1.04 g, 2.54 mmol) were dissolved in 60 mL of 1,4-dioxane to form a reaction mixture. Then, separately, potassium carbonate (K2CO3) (0.73 g, 6.92 mmol) was dissolved in 20 mL of DI water, and this was added to the reaction mixture. Then, a palladium catalyst (tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4) (0.13 g, 0.12 mmol) was added thereto. Afterwards, the resultant reaction mixture was stirred and heated under reflux at a temperature of 110° C. After an extraction process was performed thereon, the solid thus obtained was purified by column chromatography (eluents: ethyl acetate (EA) and n-hexane), to obtain 1.25 g (yield of 85%) of Compound 1B.

The obtained compound was identified by high resolution mass spectrometry using matrix assisted laser desorption ionization (HRMS (MALDI)) and high-performance liquid chromatography (HPLC) analysis.

Synthesis of Compound 1

Compound 1A (1.20 g, 1.69 mmol) and Compound 1B (1.18 g, 1.85 mmol) were mixed with 15 mL of 2-ethoxyethanol and 15 mL of N,N-dimethylformamide, stirred and heated under reflux for 24 hours, and then the temperature was allowed to lower to room temperature. The solvent was removed from the reaction mixture under a reduced pressure, and a solid thus obtained was purified to column chromatography (eluents: MC and hexane) to obtain 1.01 g (yield of 53%) of Compound 1. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

Synthesis Example 2: Synthesis of Compound 2

Synthesis of Compound 2

0.96 g (yield of 50%) of Compound 2 was obtained in a similar manner as in the synthesis of Compound 1, except that 2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxoborolane-2-yl)benzo[2,3]benzofuro[5,4-d]oxazole (1.04 g, 2.54 mmol) was used instead of 2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxoborolane-2-yl)benzo[2,3]benzofuro[4,5-d]oxazole. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

Synthesis Example 3: Synthesis of Compound 4

Synthesis of Compound 4

1.08 g (yield of 56%) of Compound 4 was obtained in a similar manner as used to synthesize Compound 1, except that 2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxoborolane-2-yl)benzofuro[6,7-b]benzofuran (1.04 g, 2.54 mmol) was used instead of 2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxoborolane-2-yl)benzo[2,3]benzofuro[4,5-d]oxazole. The obtained compound was identified by HRMS (MALDI) and HPLC analysis.

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

Compounds HT3 and F12-P-dopant were co-deposited by vacuum on the anode at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and then, Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,650 Å.

Then, Compound GH3 (host) and Compound 1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 92:8 to form an emission layer having a thickness of 400 Å.

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

Examples 2 and 3 and Comparative Example 1

Organic light-emitting devices were manufactured in a similar manner as in Example 1, except that compounds described in Table 2 were each used instead of Compound 1 in the formation of the emission layer.

Evaluation Example 1: Characterization of Organic Light-Emitting Devices

The driving voltage (Volts, V), maximum emission wavelength (nm), the maximum external quantum efficiency (Max EQE, %), and lifespan (LT97, relative %) of the organic light-emitting devices of Examples 1 to 3 and Comparative Example 1 were evaluated, and the results are shown in Table 2. As an evaluation device, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the lifespan (LT97) (at 18000 candela per square meter (cd/m2)) was evaluated as the time taken for luminance to reduce to 97% of 100% of the initial luminance.

From Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 3 have a low driving voltage, a high external quantum efficiency, and a long lifespan.

In addition, it was confirmed that the organic light-emitting devices of Examples 1 to 3 have a lower driving voltage, a higher external quantum efficiency, and a longer lifespan than the organic light-emitting device of Comparative Example 1.

Since the organometallic compound represented by Formula 1 has excellent electric characteristics, an electronic device using at least one of the organometallic compounds represented by Formula 1, for example, an organic light-emitting device, may have a low driving voltage, a high efficiency, and a long lifespan. Thus, due to the use of the organometallic compounds represented by Formula 1, a high-quality organic light-emitting device may be embodied.

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 in further detail 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.