Patent ID: 12232410

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

According to an embodiment of the present disclosure, an organometallic compound is represented by Formula 1:

In Formula 1, M1and M2may each independently be selected from platinum (Pt), palladium (Pd), iridium (Ir), copper (Cu), cadmium (Cd), nickel (Ni), zinc (Zn), manganese (Mn), and gold (Au).

In one embodiment, M1and M2may be the same metals. For example, M1and M2may each be Pt.

In Formula 1, ring C1to ring C6may each independently be selected from a C5-C30carbocyclic group and a C1-C30heterocyclic group.

In one embodiment, ring C1to ring C6and ring A1and ring A2may each independently be selected from i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, and v) a condensed ring in which one or more first rings and one or more second rings are condensed with each other.

In one embodiment, the first ring may be selected from a cyclopentane group, a cyclopentene group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a borole group, a phosphol group, a silole group, a germole group, a selenophene 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, and a triazasilole group, and

the second ring may be selected from a cyclohexane group, a cyclohexene group, a cyclohexadiene group, an adamantane group, a norbornane group, a norbornene group, a benzene group, a pyridine group, a dihydropyridine group, a tetrahydropyridine group, a pyrimidine group, a dihydropyrimidine group, a tetrahydropyrimidine group, a pyrazine group, a dihydropyrazine group, a tetrahydropyrazine group, a pyridazine group, a dihydropyridazine group, a tetrahydropyridazine group, a triazine group, an oxasiline group, a thiasiline group, a dihydroazasiline group, a dihydrodisiline group, a dihydrosiline group, a dioxine group, an oxathiine group, an oxazine group, a pyran group, a dithiine group, a thiazine group, and a thiopyran group.

In one embodiment, at least one selected from ring C1to ring C6may be a heterocyclic group including a carbene moiety. For example, at least one selected from ring C1to ring C6may be a carbene group.

In one embodiment, ring C1and ring C4may be identical to each other. In one embodiment, ring C2and ring C5may be identical to each other. In one embodiment, ring C3and ring C6may be identical to each other. In one embodiment, ring C2, ring C3, ring C5, and ring C6may be identical to each other.

For example, a moiety represented by

may be a group represented by one selected from Formulae 1a to 1d, a moiety represented by

may be a group represented by one selected from Formulae 2a to 2h, a moiety represented by

may be a group represented by one selected from Formulae 3a to 3d, a moiety represented by

may be a group represented by one selected from Formulae 4a to 4d, a moiety represented by

may be a group represented by one selected from Formulae 5a to 5h, and a moiety represented by

may be a group represented by one selected from Formulae 6a to 6d:

In Formulae 1a to 1d,

Xamay be N or C(Z1a), Xbmay be N or C(Z1b), Xcmay be N or C(Z1c), Xdmay be N or C(Z1d), Xemay be N or C(Z1e), Xfmay be N or C(Z1f), and Xgmay be N or C(Z1g),

Z1ato Z1gmay each independently be the same as described in connection with R1in the present specification,

in Formulae 2a to 2h,

Xamay be N or C(Z2a), Xbmay be N or C(Z2b), Xcmay be N or C(Z2c), Xdmay be N or C(Z2d), Xemay be N or C(Z2e), Xfmay be N or C(Z2f), Xgmay be N or C(Z2g), and Xhmay be N or C(Z2h),

R2ato R2c, Z21to Z28, and Z2ato Z2hmay each independently be the same as described in connection with R2in the present specification,

in Formulae 3a to 3d,

Xamay be N or C(Z3a), Xbmay be N or C(Z3b), Xcmay be N or C(Z3c), and Xdmay be N or C(Z3d),

R3ato R3c, Z31to Z38, and Z3ato Z3dmay each independently be the same as described in connection with R3in the present specification,

in Formulae 4a to 4d,

Xamay be N or C(Z4a), Xbmay be N or C(Z4b), Xcmay be N or C(Z4c), Xdmay be N or C(Z4d), Xemay be N or C(Z4e), Xfmay be N or C(Z4f), and Xgmay be N or C(Z4g),

Z4ato Z4gmay each independently be the same as described in connection with R4in the present specification,

in Formulae 5a to 5h,

Xamay be N or C(Z5a), Xbmay be N or C(Z5b), Xcmay be N or C(Z5c), Xdmay be N or C(Z5d), Xemay be N or C(Z5e), Xfmay be N or C(Z5f), Xgmay be N or C(Z5g), and Xhmay be N or C(Z5h),

R5ato R5c, Z51to Z58, and Z5ato Z5hmay each independently be the same as described in connection with R5in the present specification,

in Formulae 6a to 6d,

Xamay be N or C(Z6a), Xbmay be N or C(Z6b), Xcmay be N or C(Z6c), and Xdmay be N or C(Z6d), and

R6ato R6c, Z61to Z68, and Z6ato Z6dmay each independently be the same as described in connection with R6in the present specification.

In Formula 1, Y1may be a constituent atom of ring C1, and may be C or N; Y2may be a constituent atom of ring C2, and may be C or N; Y3may be a constituent atom of ring C3, and may be C or N; Y4may be a constituent atom of ring C4, and may be C or N; Y5may be a constituent atom of ring C5, and may be C or N; and Y6may be a constituent atom of ring C6, and may be C or N, wherein one selected from a bond between Y1and M1, a bond between Y2and M1, and a bond between Y3and M1may be a covalent bond, and the others (i.e., the remaining two bonds excluding the one that is a covalent bond) may each be a coordinate bond, and one selected from a bond between Y4and M2, a bond between Y5and M2, and a bond between Y6and M2may be a covalent bond, and the others (i.e., the remaining two bonds excluding the one that is a covalent bond) may each be a coordinate bond.

In one embodiment, Y1and Y4may each be C, and a bond between Y1and M1and a bond between Y4and M2may each be a covalent bond.

In one or more embodiments, Y3and Y6may each be C, and a bond between Y3and M1and a bond between Y6and M2may each be a covalent bond.

In one embodiment, T1to T6may each independently be selected from a single bond, *—O—*′, *—S—*′, *—Se—*′, *—N(R7)—*′, *—B(R7)—*′, *—P(R7)—*′, *—P(═O)(R7)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—S(═O)(R7)(R8)—*′, *—C(═O)—*′, *—C(R7)(R8)—*′, *—Si(R7)(R8)—*′, and *—Ge(R7)(R8)—*′.

In one embodiment, T1and T2may each independently be selected from O, S, and Se, T3and T4may each be a single bond, and T5and T6may each independently be selected from a single bond and *—N(R7)—*′.

For example, T1and T2may each be O, T3and T4may each be a single bond, and T5and T6may each independently be selected from a single bond and *—N(R7)—*′, wherein, when T5and T6are each *—N(R7)—*′, R7may be linked to each of R1and R4to form a hetero condensed ring.

In Formula 1, R1to R8may each independently be selected from hydrogen, deuterium (D), —F, —Cl, —Br, —I, —CH2D, —CHD2, —CD3, —CH2F, —CHF2, —CF3, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, 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 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-C60alkylaryl 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 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Qi), —S(═O)2(Q1), and —P(═O)(Q1)(Q2), wherein adjacent groups from among R1to R8may optionally be linked to each other to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30heterocyclic group.

In one embodiment, R1to R8may each independently be selected from:hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, and a C1-C60alkoxy group;a C1-C60alkyl group and a C1-C60alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, and an indolocarbazolyl group;a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, and an indolocarbazolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, a C1-C60alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, an indolocarbazolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); and—Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Qi), —S(═O)2(Q1), and —P(═O)(C21)(Q2), but embodiments of the present disclosure are not limited thereto, andQ1to Q3and Q31to Q33may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60alkyl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60alkyl group, a phenyl group, and a biphenyl group, a C6-C60aryl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C10alkyl group, a phenyl group, and a biphenyl group and a C1-C60heteroaryl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C10alkyl group, a phenyl group, and a biphenyl group.

For example, R1to R8may each independently be selected from:hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an isopentyl group, a sec-pentyl group, a 3-methylpentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, and a tert-hexyl group;a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an isopentyl group, a sec-pentyl group, a 3-methylpentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, and a tert-hexyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;a cyclopentyl group a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyridinyl group, and a pyrimidinyl group; anda cyclopentyl group a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyridinyl group, and a pyrimidinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group a nitro group, an amidino group, a hydrazine group, a hydrazone group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an isopentyl group, a sec-pentyl group, a 3-methylCYpentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyridinyl group, and a pyrimidinyl group,but embodiments of the present disclosure are not limited thereto.

In Formula 1, a1 indicates the number of R1(s), and may be an integer from 0 to 10; a2 indicates the number of R2(s), and may be an integer from 0 to 10; a3 indicates the number of R3(s), and may be a integer from 0 to 10; a4 indicates the number of R4(s), and may be an integer from 0 to 10; a5 indicates the number of R5(s), and may be an integer from 0 to 10; and a6 indicates the number of R6(s), and may be an integer from 0 to 10.

In one embodiment, the organometallic compound may be represented by Formula 1-1:

In Formula 1-1,M1, M2, C1to C6, R1to R6, a1 to a6, T1to T6, and Y1to Y6may each be the same as respectively described above in the present specification,X11, X12, X21, X22, X31, X32, X41, X42, X51, X52, X61, and X62may each independently be C or N,when X21is N, X22may be N, and Y2may be C,when X31is N, X32may be N, and Y3may be C,when X51is N, X52may be N, and Y5may be C, andwhen X61is N, X62may be N, and Y6may be C.

In one embodiment, X31, X32, X61, and X62may each be N, and Y3and Y6may each be C.

In one or more embodiments, when X21and X22are each C, Y2may be N, and when X51and X52are each C, Y5may be N; orwhen X21and X22are each N, Y2may be C, and X22and Y2or X21and Y2may each include a *—N═C—*′ bond, and when X51and X52are each N, Y5may be C, and X52and Y5or X51and Y5may each include a *—N═C—*′ bond.

In one embodiment, the organometallic compound may be represented by Formula 1-2:

In Formula 1-2,M1, M2, C1, C2, C4, C5, R1, R2, R4, R5, a1, a2, a4, a5, T1to T6, Y1, Y2, Y4, and Y5may each be the same as respectively described above in the present specification,R3ato R3cmay each independently be the same as described in connection with R3in the present specification, andR6ato R6cmay each independently be the same as described in connection with R6in the present specification.

In one embodiment, the organometallic compound may be represented by Formula 1-3 or 1-4:

In Formulae 1-3 and 1-4,M1, M2, C2, C3, C5, C6, Y2, Y3, Y5, Y6, R2, R3, R5, R6, a2, a3, a5, a6, and T1to T6may each be the same as respectively described above in the present specification,X13may be N or C(R13), X14may be N or C(R14), X15may be N or C(R15), X16may be N or C(R16), X17may be N or C(R17), X18may be N or C(R18), and X19may be N or C(R19),X43may be N or C(R43), X44may be N or C(R44), X45may be N or C(R45), X46may be N or C(R46), X47may be N or C(R47), X48may be N or C(R48), and X49may be N or C(R49),R13to R19may each independently be the same as described in connection with R1in the present specification, andR43to R49may each independently be the same as described in connection with R4in the present specification.

In one embodiment, the organometallic compound may be represented by one of Formulae 1-5 to 1-7:

In Formulae 1-5 to 1-7,M1, M2, C1, C3, C4, C6, R1, R3, R4, R6, a1, a3, a4, a6, T1to T6, Y1, Y3, Y4, andY6may each be the same as respectively described above in the present specification,X21may be N or C(R21), X22may be N or C(R22), X23may be N or C(R23), and X24may be N or C(R24),X51may be N or C(R51), X52may be N or C(R52), X53may be N or C(R53), and X54may be N or C(R54),V21may be N or C(RV21), V22may be N or C(RV22), V23may be N or C(RV23), and V24may be N or C(RV24),V51may be N or C(RV51), V52may be N or C(RV52), V53may be N or C(RV53), and V54may be N or C(RV54),R2ato R2c, R21to R24, and RV21to RV24may each independently be the same as described in connection with R2in the present specification, andR5ato R5c, R51to R54, and RV51to RV54may each independently be the same as described in connection with R5in the present specification.

In one embodiment, the organometallic compound may be selected from Compounds BD 1 to BD 93:

The organometallic compound represented by Formula 1 is a heteronuclear complex including two central metals, and more bulky substituents may be introduced thereto by sharing a benzene ring as a ligand. Accordingly, the tilt angle between ligands becomes larger, and as a result, excimer and exciplex formation between compounds may be suppressed, thereby providing (e.g., improving) long lifespan characteristics.

In addition, because the organometallic compound represented by Formula 1 is a heteronuclear complex including two central metals, an area of a light-emitting moiety increases, thereby increasing the luminescence efficiency.

According to another embodiment of the present disclosure, 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 and including an emission layer,wherein the organic layer includes the organometallic compound.

In one embodiment, the emission layer may include the organometallic compound.

In one embodiment, the emission layer may further include a second compound and a third compound; the organometallic compound, the second compound, and the third compound may be different from each other; the second compound and the third compound may form an exciplex; and the organometallic compound and the second compound and/or the organometallic compound and the third compound may not form an exciplex.

When the organometallic compound has a heteronuclear complex structure, the exciplex formation with an organic compound may be suppressed, thereby improving color purity and luminescence efficiency of the organometallic compound.

In one embodiment, the second compound may be represented by Formula 2, andthe third compound may include a group represented by Formula 3:

In Formulae 2 and 3, ring CY51to ring CY53, ring CY71, and ring CY72may each independently be selected from a C5-C30carbocyclic group and a C1-C30heterocyclic group.

In one embodiment, in Formulae 2 and 3, ring CY51to ring CY53, ring CY71, and ring CY72may each independently be selected from i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, and v) a condensed ring in which one or more first rings and one or more second rings are condensed with each other,the first ring may be selected from a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole 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, and a triazasilole group, andthe second ring may be selected from 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, a triazine group, an oxasiline group, a thiasiline group, a dihydroazasiline group, a dihydrodisiline group, a dihydrosiline group, a dioxine group, an oxathiine group, an oxazine group, a pyran group, a dithiine group, a thiazine group, a thiopyran group, a cyclohexadiene group, a dihydropyridine group, and a dihydropyrazine group.

For example, in Formulae 2 and 3, ring CY51to ring CY53, ring CY71, and ring CY72may each independently be selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group, but embodiments of the present disclosure are not limited thereto.

In Formula 2, L51to L53may each independently be selected from a substituted or unsubstituted C5-C30carbocyclic group and a substituted or unsubstituted C1-C30heterocyclic group. In Formula 2, L51to L53may each independently be selected from a substituted or unsubstituted C1-C20alkylene group, a substituted or unsubstituted C2-C20alkenylene group, a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

In one embodiment, in Formula 2, L51to L53may each independently be selected from: a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, and a benzothiadiazole group;a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, and a benzothiadiazole group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); and—C(Q31)(Q32)-*′, *—Si(Q31)(Q32)-*′, *—N(Q31)-*′, *—B(Q31)-*′, *—C(═O)—*′, *—S(═O)2—*′, and *—P(═O)(Q31)-*′,Q31to Q33may each independently be selected from hydrogen, deuterium, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, but embodiments of the present disclosure are not limited thereto, and* and *′ each indicate a binding site to an adjacent atom.

In Formulae 2 and 3, a bond between L51and ring CY51, a bond between L52and ring CY52, a bond between L53and ring CY53, a bond between two or more L51(s), a bond between two or more L52(s), a bond between two or more L53(s), a bond between L51and the carbon atom between X54and X55in Formula 2, a bond between L52and the carbon atom between X54and X56in Formula 2, and a bond between L53and the carbon atom between X55and X56in Formula 2 may each be a carbon-carbon single bond.

In Formula 2, b51 to b53 may each independently be an integer from 0 to 5, wherein, when b51 is 0, *-(L51)b51-*′ may be a single bond, when b52 is 0, *-(L52)b52-*′ may be a single bond, and when b53 is 0, *-(L53)b53-*′ may be a single bond.

For example, b51 to b53 may each independently be 0, 1, or 2.

In Formula 2, X54may be N or C(R54), X55may be N or C(R55), X56may be N or C(R56), and at least one selected from X54to X56may be N. R54to R56may be the same as described above in the present specification.

In Formula 3, X81may be a single bond, O, S, N(R81), B(R81), C(R81a)(R81b), or Si(R81a)(R81b). R81, R81a, and R81bmay be the same as described above in the present specification.

In Formulae 2 and 3, R51to R56, R71, R72, R81, R81a, and R81bmay each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, 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 C3-C10cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C7-C60alkylaryl 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-C60alkylheteroaryl 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2), and Q1to Q3may each independently be the same as described above in the present specification.

In one embodiment, in Formulae 2 and 3, R51to R56, R71, R72, R81, R81a, and R81bmay each independently be selected from:hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, and a C1-C60alkoxy group;a C1-C60alkyl group and a C1-C60alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, and an indolocarbazolyl group;a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, an indolocarbazolyl group, and a group represented by Formula 91, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, a C1-C60alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolyl group, an indolocarbazolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); and—Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Qi), —S(═O)2(Q1), and —P(═O)(Qi)(Q2), andwherein Q1to Q3and Q31to Q33may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60alkyl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60alkyl group, a phenyl group, and a biphenyl group, a C6-C60aryl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C10alkyl group, a phenyl group, and a biphenyl group, and a C1-C60heteroaryl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C10alkyl group, a phenyl group, and a biphenyl group, but embodiments of the present disclosure are not limited thereto:

In Formula 91,ring CY91and ring CY92may each independently be selected from a C5-C30carbocyclic group and a C1-C30heterocyclic group,X91may be a single bond, O, S, N(R91), B(R91), C(R91a)(R91b), or Si(R91a)(R91b),R91, R91a, and R91bare each the same as described in connection with R81, R81a, and R81b, respectively, in the present specification, and* indicates a binding site to a neighboring atom.

For example, in Formula 91,ring CY91and ring CY92may each independently be selected from a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group,R91, R91a, and R91bmay each independently be selected from:hydrogen and a C1-C10alkyl group;a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group; anda phenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, each substituted with at least one selected from deuterium, a C1-C10alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group,but embodiments of the present disclosure are not limited thereto.

In Formulae 2 and 3, a51 to a53, a71, and a72 each indicate the number of R51(s) to R53(s), the number of R71(s), and the number of R72(s), respectively, and may each independently be an integer from 0 to 10. When a51 is 2 or more, two or more R51(s) may be identical to or different from each other, and a52, a53, a71, and a72 are each understood in the same manner as in a51.

In one embodiment, a group represented by

in Formula 2 and a group represented by

in Formula 2 may not be each a phenyl group.

In one or more embodiments, a group represented by

in Formula 2 and a group represented by

in Formula 2 may be identical to each other.

In one or more embodiments, in Formula 2, ring CY51and ring CY52may each independently be selected from a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, and a triazine group,R51and R52may each independently be selected from 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-C60alkylaryl 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q1)(Q2)(Q3),Q1to Q3may each independently be selected from a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group and a C6-C60aryl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C10alkyl group, a phenyl group, and a biphenyl group, anda51 and a52 may each independently be 1, 2, or 3.

In one or more embodiments, in Formula 2, a moiety represented by

may be selected from groups represented by Formulae CY51-1 to CY51-18, and/or,a moiety represented by

may be selected from groups represented by Formulae CY52-1 to CY52-18, and/or,a moiety represented by

may be selected from groups represented by Formulae CY53-1 to CY53-19:

In Formulae CY51-1 to CY51-18, CY52-1 to CY52-18, and CY53-1 to CY53-19,T1may be a single bond, O, S, C(T11)(T12), or Si(T11)(T12),T2may be a single bond, O, S, N(T21), B(T21), C(T21)(T22), or Si(T21)(T22),T3may be a single bond, O, S, N(T31), B(T31), C(T31)(T32), or Si(T31)(T32),T4may be a single bond, O, S, N(T41), B(T41), C(T41)(T42), or Si(T41)(T42),T1and T2in Formulae CY51-16 and CY51-17 may not be a single bond at the same time, that is, T1and T2in Formulae CY51-16 and CY51-17 may not both be a single bond,T3and T4in Formulae CY52-16 and CY52-17 may not be a single bond at the same time, that is, T3and T4in Formulae CY52-16 and CY52-17 may not both be a single bond,R51ato R51g, T11, T12, T21, and T22may each independently be the same as described in connection with R51in the present specification, but R51ato R51emay not each be hydrogen, for example, none of R51ato R51emay be hydrogen,R52ato R52i, T31, T32, T41, and T42may each independently be the same as described in connection with R52in the present specification, but R52ato R52emay not each be hydrogen, for example, none of R52ato R52emay be hydrogen,R53ato R53gmay each independently be the same as described in connection with R53in the present specification, but R53ato R53emay not each be hydrogen, for example, none of R53ato R53emay be hydrogen,Z1to Z6, Z8and Z9in Formulae CY52-18 and CY53-19 may each independently be C or N, and* indicates a binding site to a neighboring atom.

For example, in Formulae CY51-1 to CY51-15 and CY52-1 to CY52-15, R51ato R51eand R52ato R52emay each independently be selected from:a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, and a group represented by Formula 91;a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, and a group represented by Formula 91, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and
—C(Q1)(Q2)(Q3) and —Si(Q1)(Q2)(Q3),Q1to Q3may each independently be selected from:a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group; anda phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, each substituted with at least one selected from deuterium, a C1-C10alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, andin Formulae CY51-16 and CY51-17, i) T1may be O or S, and T2may be Si(T21)(T22), or ii) T1may be Si(T11)(T12), and T2may be O or S, andin Formulae CY52-16 and CY52-17, i) T3may be O or S, and T4may be Si(T41)(T42), or ii) T3may be Si(T31)(T32), and T4may be O or S. However, embodiments of the present disclosure are not limited thereto.

In one or more embodiments, the third compound may be represented by one of Formulae 3-1 to 3-5:

In Formulae 3-1 to 3-5,ring CY71, ring CY72, X81, R71, R72, a71, and a72 may each be the same as respectively described above in the present specification,ring CY73, ring CY74, R73, R74, a73, and a74 may each be the same as described in connection with ring CY71, ring CY72, R71, R72, a71, and a72, respectively, in the present specification,L81may be selected from *—C(Q4)(Q5)—*′, *—Si(Q4)(Q5)—′, a substituted or unsubstituted C5-C30carbocyclic group, and a substituted or unsubstituted C1-C30heterocyclic group, wherein Q4and Q5may each independently be the same as described in connection with Q1in the present specification,b81 may be an integer from 0 to 5, wherein, when b81 is 0, *-(L81)b81-*′ may be a single bond, and when b81 is 2 or more, two or more L81(s) may be identical to or different from each other,X82may be a single bond, O, S, N(R82), B(R82), C(R82a)(R82b), or Si(R82a)(R82b),X83may be a single bond, O, S, N(R83), B(R83), C(R83a)(R83b), or Si(R83a)(R83b),in Formulae 3-2 and 3-4, X82and X83may not be a single bond at the same time, that is, X82and X83may not both be a single bond,X84may be C or Si,R80, R82, R83, R82a, R82b, R83a, R83b, and R84may each independently be the same as described in connection with R81in the present specification, and* and *′ each indicate a binding site to a neighboring atom.

For example, L81may be selected from:
*—C(Q4)(Q5)—*′ and *—Si(Q4)(Q5)—*′;a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, and a benzothiadiazole group; anda benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, and a benzothiadiazole group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —O(Q31), —S(Q31), —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32), andQ4, Q5, and Q31to Q33may each independently be selected from hydrogen, deuterium, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, but embodiments of the present disclosure are not limited thereto.

For example, in Formulae 3-1 and 3-2, a moiety represented by

may be selected from groups represented by Formulae CY71-1(1) to CY71-1(8),in Formulae 3-1 and 3-3, a moiety represented by

may be selected from groups represented by Formulae CY71-2(1) to CY71-2(8),in Formulae 3-2 and 3-4, a moiety represented by

may be selected from groups represented by Formulae CY71-3(1) to CY71-3(32),in Formulae 3-3 to 3-5, a moiety represented by

may be selected from groups represented by Formulae CY71-4(1) to CY71-4(32), andin Formula 3-5, a moiety represented by

may be selected from groups represented by Formulae CY71-5(1) to CY71-5(8). However, embodiments of the present disclosure are not limited thereto:

In Formulae CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),X81to X84, R80, and R84may each be the same as respectively described above in the present specification,X85may be a single bond, O, S, N(R85), B(R85), C(R85a)(R85b), or Si(R85a)(R85b),X86may be a single bond, O, S, N(R86), B(R86), C(R86a)(R86b), or Si(R86a)(R86b),in Formulae CY71-1(1) to CY71-1(8) and CY71-4(1) to CY71-4(32), X85and X86may not be a single bond at the same time, that is, X85and X86may not both be a single bond,X87may be a single bond, O, S, N(R87), B(R87), C(R87a)(R87b), or Si(R87a)(R87b), andX88may be a single bond, O, S, N(R88), B(R88), C(R88a)(R88b), or Si(R88a)(R88b), andin Formulae CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to CY71-5(8), X87and X88may not be a single bond at the same time, that is, X87and X88may not both be a single bond, andR85to R88, R85a, R85b, R86a, R86b, R87a, R87b, R88a, and R88bmay each independently be the same as described in connection with R81in the present specification.

In one embodiment, the second compound may be selected from Compounds ETH1 to ETH80:

In one or more embodiments, the third compound may be selected from Compounds HTH1 to HTH28:

In one embodiment, the organic light-emitting device may satisfy at least one of Condition 1 to Condition 4:
LUMO energy level (eV) of the third compound>LUMO energy level (eV) of the organometallic compound;  Condition 1
LUMO energy level (eV) of the organometallic compound>LUMO energy level (eV) of the second compound;  Condition 2
HOMO energy level (eV) of the organometallic compound>HOMO energy level (eV) of the third compound; and  Condition 3
HOMO energy level (eV) of the third compound>HOMO energy level (eV) of the second compound.  Condition 4

The HOMO energy levels and the LUMO energy levels of each of the organometallic compound, the second compound, and the third compound are negative values, and may be measured according to a suitable (e.g., a known) method, for example, a method described in Evaluation Example 1 in the present specification.

In one or more embodiments, an absolute value of the difference between the LUMO energy level of the organometallic compound and the LUMO energy level of the second compound may be 0.1 eV or more and 1.0 eV or less, an absolute value of the difference between the LUMO energy level of the organometallic compound and the LUMO energy level of the third compound may be 0.1 eV or more and 1.0 eV or less, an absolute value of the difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the second compound may be 1.25 eV or less (for example, 1.25 eV or less and 0.2 eV or more), an absolute value of the difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the third compound may be 1.2 5 eV or less (for example, 1.25 eV or less and 0.2 eV or more), and an absolute value of the difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the exciplex formed between the second compound and the third compound may be 1.25 eV or less.

When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described above, the balance between holes and electrons injected into the emission layer can be made.

The emission layer of the organic light-emitting device may include:1) the organometallic compound represented by Formula 1 (heteronuclear complex);2) the second compound represented by Formula 2 (wherein, in Formula 2, a bond between L51and ring CY51, a bond between L52and ring CY52, a bond between L53and ring CY53, a bond between two or more L51(s), a bond between two or more L52(s), a bond between two or more L53(s), a bond between L51and the carbon atom between X54and X55in Formula 2, a bond between L52and the carbon atom between X54and X56in Formula 2, and a bond between L53and the carbon atom between X55and X56in Formula 2 may each be a “carbon-carbon” single bond); and3) the third compound represented by Formula 3, which is different from the compounds represented by Formulae 1 and 2,and accordingly, the exciplex formation between the organometallic compound and either the second compound or the third compound is effectively suppressed, thereby implementing the organic light-emitting device having high color purity and a long lifespan.

The decay time of delayed fluorescence in the time-resolved electroluminescence (TREL) spectrum of the organic light emitting device may be 50 ns or more, for example, 50 ns or more and 2.5 μs or less. In one embodiment, the decay time of delayed fluorescence in the TREL spectrum of the organic light-emitting device may be 50 ns or more and 2.4 μs or less, 50 ns or more and 2.3 μs or less, 50 ns or more and 2.2 μs or less, 50 ns or more and 2.1 μs or less, or 50 ns or more and 2 μs or less. When the decay time of delayed fluorescence of the organic light-emitting device is within these ranges, the time that the organometallic compound remains in an excited state is relatively reduced, so that the organic light-emitting device may have high luminescent efficiency and a long lifespan.

In one embodiment, the electroluminescence (EL) spectrum of the organic light-emitting device may have a first peak and a second peak, wherein a maximum emission wavelength of the second peak may be greater than that of the first peak, a difference between the maximum emission wavelength of the second peak and the maximum emission wavelength of the first peak may be 5 nm or more and 10 nm or less, and an intensity of the second peak may be smaller than that of the first peak.

When the difference between the maximum emission wavelength of the second peak and the maximum emission wavelength of the first peak is within the ranges above, the organic light-emitting device having excellent color purity (for example, a blue organic light-emitting device having excellent color purity) may be implemented (e.g., obtained).

The maximum emission wavelength of the first peak may be 390 nm or more and 500 nm or less (for example, 430 nm or more and 470 nm or less). In this regard, the organic light-emitting device may emit blue light (for example, dark blue light) having excellent color purity.

The first peak and the second peak may each be an emission peak of phosphorescence emitted by the organometallic compound.

The organometallic compound may have a heteronuclear structure in which two metals are coordinated, and accordingly, the exciplex formation between the organometallic compound and either the second compound or the third compound may be suppressed, thereby achieving high efficiency and high color purity of the organometallic compound.

The intensity of the second peak may be 20% to 90% of the intensity of the first peak. When the intensity of each of the second peak and the first peak is within the range above, the light emission by the second peak may be suppressed by the organometallic compound while the efficiency of phosphorescence emitted by the second compound or the third compound is not reduced, thereby implementing the organic light-emitting device having improved color purity.

The organometallic compound, the second compound, and the third compound may be the same as described above.

Another aspect of the present disclosure provides an electronic apparatus including the organic light-emitting device. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the organic light-emitting device is electrically connected to the source electrode or the drain electrode.

[Description ofFIG.1]

FIG.1is a schematic cross-sectional view of an organic light-emitting device10according to an embodiment. The organic light-emitting device10includes a first electrode110, an organic layer150, and a second electrode190.

Hereinafter, the structure of the organic light-emitting device10according to an embodiment and a method of manufacturing the organic light-emitting device10will be described in connection withFIG.1.

[First Electrode110]

InFIG.1, a substrate may be additionally located under the first electrode110or above the second electrode190. The substrate may be a glass substrate or a plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water resistance.

The first electrode110may be formed by, for example, depositing or sputtering a material for forming the first electrode on the substrate. When the first electrode110is an anode, the material for forming the first electrode110may be selected from materials with a high work function to facilitate hole injection.

The first electrode110may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode110is a transmissive electrode, the material for forming the first electrode110may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode110is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combination thereof, but embodiments of the present disclosure are not limited thereto.

The first electrode110may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode110may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode110is not limited thereto.

[Organic layer150]

The organic layer150is located on the first electrode110. The organic layer150may include an emission layer.

The organic layer150may further include a hole transport region between the first electrode110and the emission layer and an electron transport region between the emission layer and the second electrode190.

[Hole transport region in organic layer150]

The hole transport region may have i) a single-layered structure including including (e.g., consisting of) a single material, ii) a single-layered structure including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.

For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials, or a multi-layered structure having a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein for each structure, constituting layers are sequentially stacked from the first electrode110in the respective stated order, but the structure of the hole transport region is not limited thereto.

The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB(NPD), p-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PAN I/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,L201to L204may each independently be selected from a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,L205may be selected from *—O—*′, *—N(Q201)-*′, a substituted or unsubstituted C1-C20alkylene group, a substituted or unsubstituted C2-C20alkenylene group, a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,xa1 to xa4 may each independently be an integer from 0 to 3,xa5 may be an integer from 1 to 10, andR201to R204and Q201may each independently be selected from 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 C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R201and R202may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R203and R204may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

In one embodiment, in Formulae 201 and 202,L201to L205may each independently be selected from:a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group; anda phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an am idino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q31)(Q32)(Q33), and —N(Q31)(Q32), andQ31to Q33may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R201to R204and Q201may each independently be selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; anda phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q31)(Q32)(Q33), and —N(Q31)(Q32), andQ31to Q33may each independently be the same as described above in the present specification.

In one or more embodiments, at least one selected from R201to R203in Formula 201 may each independently be selected from:a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; anda fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R201and R202may be linked to each other via a single bond, and/or ii) R203and R204may be linked to each other via a single bond.

In one or more embodiments, at least one of R201to R204in Formula 202 may be selected from:a carbazolyl group; anda carbazolyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula 201-1:

In one embodiment, the compound represented by Formula 201 may be represented by Formula 201-2, but embodiments of the present disclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201-2(1), but embodiments of the present disclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A:

In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A(1), but embodiments of the present disclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1, but embodiments of the present disclosure are not limited thereto:

In one embodiment, the compound represented by Formula 202 may be represented by Formula 202-1:

In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202-1(1):

In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202A:

In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:

In Formulae 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A, and 202A-1,L201to L203, xa1 to xa3, xa5, and R202to R204may be the same as respectively described above in the present specification,L205may be selected from a phenylene group and a fluorenylene group,X211may be selected from O, S, and N(R211),X212may be selected from O, S, and N(R212),R211and R212may each independently be the same as described in connection with R203, andR213to R217may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.

The hole transport region may include at least one compound selected from Compounds HT1 to HT48, but embodiments of the present disclosure are not limited thereto:

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 selected from a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer, and the electron blocking layer may block or reduce the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may include the materials as described above.

[p-Dopant]

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.

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

In one embodiment, a LUMO energy level of the p-dopant may be −3.5 eV or less.

The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.

In one embodiment, the p-dopant may include at least one selected from:a quinone derivative, such as tetracyanoquinodimethane (TCNQ) and/or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);a metal oxide, such as tungsten oxide or molybdenum oxide;1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); anda compound represented by Formula 221,but embodiments of the present disclosure are not limited thereto:

In Formula 221,R221to R223may each independently be selected from 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 C1-C60heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and at least one selected from R221to R223may have at least one substituent selected from a cyano group, —F, —Cl, —Br, —I, a C1-C20alkyl group substituted with —F, a C1-C20alkyl group substituted with —Cl, a C1-C20alkyl group substituted with —Br, and a C1-C20alkyl group substituted with —I.
[Emission Layer in Organic Layer150]

When the organic light-emitting device10is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers may contact each other or may be separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.

The emission layer may include a host and a dopant. The dopant may include the organometallic compound represented by Formula 1. The host may include at least one of the second compound and the third compound. The third compound and the second compound may be the same as described above in the present specification.

An amount of a dopant in the emission layer may be, based on about 100 parts by weight of the host, about 0.01 parts by weight to about 15 parts by weight, but embodiments of the present disclosure are not limited thereto.

A thickness of the emission layer may be about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

[Electron Transport Region in Organic Layer150]

The electron transport region may have i) a single-layered structure including (e.g., consisting of) a single material, ii) a single-layered structure including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein for each structure, constituting layers are sequentially stacked from an emission layer. However, embodiments of the structure of the electron transport region are not limited thereto.

The electron transport region may include the second compound as described above.

In one embodiment, the electron transport region may include a buffer layer, the buffer layer may be in direct contact with the emission layer, and the buffer layer may include the second compound as described above.

In one or more embodiments, the electron transport region may include a buffer layer, an electron transport layer, and an electron injection layer stacked in this stated order from the emission layer, and the buffer layer may include the second compound as described above.

In one or more embodiments, the electron transport region (for example, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.

The term “π electron-depleted nitrogen-containing ring” as used herein refers to a C1-C60heterocyclic group having including at least one *—N═*′ moiety as a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *—N═*′ moiety, ii) a heteropolycyclic group in which two or more 5-membered to 7-membered heteromonocyclic groups each having at least one *—N═*′ moiety are condensed with each other, or iii) a heteropolycyclic group in which at least one of 5-membered to 7-membered heteromonocyclic groups, each having at least one *—N═*′ moiety, is condensed with at least one C5-C60carbocyclic group.

Examples of the π electron-depleted (or π electron-deficient) nitrogen-containing ring include an imidazole ring, a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an indazole ring, a purine ring, a quinoline ring, an isoquinoline ring, a benzoquinoline ring, a phthalazine ring, a naphthyridine ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, a phenanthridine ring, an acridine ring, a phenanthroline ring, a phenazine ring, a benzimidazole ring, an isobenzothiazole ring, a benzoxazole ring, an isobenzoxazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a triazine ring, a thiadiazole ring, an imidazopyridine ring, an imidazopyrimidine ring, and an azacarbazole ring, but are not limited thereto.

For example, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601])xe21Formula 601

In Formula 601,Ar601may be a substituted or unsubstituted C5-C60carbocyclic group or a substituted or unsubstituted C1-C60heterocyclic group,xe11 may be 1, 2, or 3,L601may be selected from a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,xe1 may be an integer from 0 to 5,R601may be selected from a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q601)(Q602)(Q603), —C(═O)(Q601), —S(═O)2(Q601), and —P(═O)(Q601)(Q602),Q601to Q603may each independently be a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, andxe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar601(s) in the number of xe11 andR601(s) in the number of xe21 may include the π electron-depleted nitrogen-containing ring.

In one embodiment, Ar601in Formula 601 may be selected from:a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; anda benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —S(═O)2(Q31), and —P(═O)(Q31)(Q32), andQ31to Q33may each independently be selected from a C1-C10alkyl group, a C1-C10alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

When xe11 in Formula 601 is 2 or more, two or more Ar601(s) may be linked to each other via a single bond.

In one or more embodiments, Ar601in Formula 601 may be an anthracene group.

In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

In Formula 601-1,X614may be N or C(R614), X615may be N or C(R615), X616may be N or C(R616), and at least one of X614to X616may be N,L611to L613may each independently be the same as described in connection with L601,xe611 to xe613 may each independently be the same as described in connection with xe1,R611to R613may each independently be the same as described in connection with R601, andR614to R616may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In one embodiment, L601and L611to L613in Formulae 601 and 601-1 may each independently be selected from:a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; anda phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group,but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.

In one or more embodiments, R601and R611to R613in Formulae 601 and 601-1 may each independently be selected from:a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; and
—S(═O)2(Q601) and —P(═O)(Q601)(Q602), and

Q601and Q602may be the same as respectively described above in the present specification.

The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:

In one or more embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:

Thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a substantial increase in driving voltage.

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. When the thickness of the electron transport layer is within the range described above, satisfactory electron transport characteristics may be obtained without a substantial increase in driving voltage.

The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth-metal complex. The alkali metal complex may include a metal ion selected from a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and a cesium (Cs) ion, and the alkaline earth-metal complex may include a metal ion selected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, and a barium (Ba) ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be selected from a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) and/or ET-D2:

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode190. The electron injection layer may directly contact the second electrode190.

The electron injection layer may have i) a single-layered structure including including (e.g., consisting of) a single material, ii) a single-layered structure including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.

In one embodiment, the electron injection layer may include Li, Na, K, Rb, Cs, Mg, Ca, Er, Tm, Yb, or any combination thereof, but embodiments of the present disclosure are not limited thereto.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li, or Cs, but embodiments of the present disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).

The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be selected from oxides and halides (for example, fluorides, chlorides, bromides, and/or iodides) of the alkali metal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, such as Li2O, Cs2O, or K2O, and alkali metal halides, such as LiF, NaF, CsF, KF, LiI, Nal, CsI, or KI. In one embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, Nal, CsI, and KI, but embodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkaline earth-metal oxides, such as BaO, SrO, CaO, BaxSr1-xO (0<x<1), or BaxCa1-xO (0<x<1). In one embodiment, the alkaline earth-metal compound may be selected from BaO, SrO, and CaO, but embodiments of the present disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an ion of alkali metal, alkaline earth-metal, and rare earth metal as described above, and a ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy phenyloxadiazole, hydroxy phenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

The electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth-metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

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

In one embodiment, the electron transport region of the organic light-emitting device10may include the buffer layer, the electron transport layer, and the electron injection layer, and

at least one layer selected from the electron transport layer and the electron injection layer may include the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof.

[Second Electrode190]

The second electrode190is located on the organic layer150having such a structure. The second electrode190may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode, a metal, an alloy, an electrically conductive compound, and a mixture thereof, each having a low work function, may be utilized.

The second electrode190may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are not limited thereto. The second electrode190may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode190may have a single-layered structure or a multi-layered structure including two or more layers.

[Description ofFIGS.2to4]

An organic light-emitting device20ofFIG.2includes a first capping layer210, a first electrode110, an organic layer150, and a second electrode190which are sequentially stacked in this stated order, an organic light-emitting device30ofFIG.3includes a first electrode110, an organic layer150, a second electrode190, and a second capping layer220which are sequentially stacked in this stated order, and an organic light-emitting device40ofFIG.4includes a first capping layer210, a first electrode110, an organic layer150, a second electrode190, and a second capping layer220.

RegardingFIGS.2to4, the first electrode110, the organic layer150, and the second electrode190may be understood by referring to the description presented in connection withFIG.1.

In the organic layer150of each of the organic light-emitting devices20and40, light generated in an emission layer may pass through the first electrode110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer210toward the outside, and in the organic layer150of each of the organic light-emitting devices30and40, light generated in an emission layer may pass through the second electrode190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer220toward the outside.

The first capping layer210and the second capping layer220may increase external luminescent efficiency according to the principle of constructive interference.

The first capping layer210and the second capping layer220may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

At least one selected from the first capping layer210and the second capping layer220may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth-based complexes. The carbocyclic compound, the heterocyclic compound, and the amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one of the first capping layer210and the second capping layer220may each independently include an amine-based compound.

In one embodiment, at least one selected from the first capping layer210and the second capping layer220may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

Hereinbefore, the organic light-emitting device according to an embodiment has been described in connection withFIGS.1to4. However, embodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region may be formed in a certain region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.

When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the vacuum deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8torr to about 10−3torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec by taking into account a compound to be included in the layer to be formed and the structure of the layer to be formed.

When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80° C. to about 200° C. by taking into account a compound to be included in the layer to be formed and the structure of the layer to be formed.

General Definition of Substituents

The term “C1-C60alkyl group” as used herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “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 having 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, and a butenyl group. The term “C2-C60alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60alkenyl group.

The term “C2-C60alkynyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60alkyl group, and non-limiting examples thereof include an ethynyl group, and a propynyl group. The term “C2-C60alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60alkynyl group.

The term “C1-C60alkoxy group” as used herein refers to a monovalent group represented by —OA101(wherein A101is the C1-C60alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.

The term “C3-C10cycloalkyl 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, and a cycloheptyl group. The term “C3-C10cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10cycloalkyl group.

The term “C1-C10heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10heterocycloalkyl group.

The term “C3-C10cycloalkenyl group” used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10cycloalkenyl group.

The term “C1-C10heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Non-limiting examples of the C1-C10heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10heterocycloalkenyl group.

The term “C6-C60aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluorenyl group, and a chrysenyl group. When the C6-C60aryl group and the C6-C60arylene group each include two or more rings, the two or more rings may be fused to each other. The term “C7-C60alkylaryl group” as used herein refers to a C6-C60aryl group substituted with at least one C1-C60alkyl group.

The term “C1-C60heteroaryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms.

The term “C1-C60heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. Non-limiting examples of the C1-C60heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiofuranyl group. When the C1-C60heteroaryl group and the C1-C60heteroarylene group each include two or more rings, the two or more rings may be condensed with each other. The term “C2-C60alkylheteroaryl group” as used herein refers to a C1-C60heteroaryl group substituted with at least one C1-C60alkyl group.

The term “C6-C60aryloxy group” as used herein refers to —OA102(wherein A102is the C6-C60aryl group), and the term “C6-C60arylthio group” as used herein refers to —SA103(wherein A103is the C6-C60aryl group).

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 with each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. A non-limiting example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl group, and an adamantyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, at least one heteroatom selected from N, O, Si, P, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. A non-limiting example of the monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group and an azaadamantyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C5-C60carbocyclic group” as used herein refers to a monocyclic or polycyclic group that includes only carbon atoms as a ring-forming atom and consists of 5 to 60 carbon atoms. The C5-C60carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C5-C60carbocyclic group may be a ring, such as benzene, a monovalent group, such as a phenyl group, or a divalent group, such as a phenylene group. In one or more embodiments, depending on the number of substituents connected to the C5-C60carbocyclic group, the C5-C60carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C1-C60heterocyclic group” as used herein refers to a group having the same structure as the C5-C60carbocyclic group, except that as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S is used in addition to carbon (the number of carbon atoms may be in a range of 1 to 60).

In the present specification, at least one substituent of the substituted C5-C60carbocyclic group, the substituted C1-C60heterocyclic group, the substituted C1-C20alkylene group, the substituted C2-C20alkenylene group, the substituted C3-C10cycloalkylene group, the substituted C1-C10heterocycloalkylene group, the substituted C3-C10cycloalkenylene group, the substituted C1-C10heterocycloalkenylene group, the substituted C6-C60arylene group, the substituted C1-C60heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C1-C60alkyl group, the substituted C2-C60alkenyl group, the substituted C2-C60alkynyl group, the substituted C1-C60alkoxy 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-C60alkylaryl group, the substituted C6-C60aryloxy group, the substituted C6-C60arylthio group, the substituted C1-C60heteroaryl group, the substituted C2-C60alkyl heteroaryl 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 may be selected from:

deuterium, —F, —Cl, —Br, —I, —CH2D, —CHD2, —CD3, —CH2F, —CHF2, —CF3, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, and a C1-C60alkoxy group;a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, and a C1-C60alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CH2D, —CHD2, —CD3, —CH2F, —CHF2, —CF3, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C7-C60alkylaryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a C2-C60alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(C211)(C212)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C7-C60alkylaryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a C2-C60alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 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-C60alkylaryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a C2-C60alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Br, —CH2D, —CHD2, —CD3, —CH2F, —CHF2, —CF3, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C7-C60alkylaryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a C2-C60alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32), andQ1to Q3, Q11to Q13, Q21to Q23, and Q31to Q33may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —CH2D, —CHD2, —CD3, —CH2F, —CHF2, —CF3, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C1-C60heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60alkyl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60alkyl group, a phenyl group, and a biphenyl group and a C6-C60aryl group that is substituted with at least one selected from deuterium, —F, a cyano group, a C1-C10alkyl group, a phenyl group, and a biphenyl group.

The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the term “ter-Bu” or “But” as used herein refers to a tert-butyl group, the term “OMe” as used herein refers to a methoxy group, the term “Ad” as used herein refers to an adamantyl group, and the term “i-Pr” as used herein refers to an isopropyl group.

The term “biphenyl group” as used herein refers to “a phenyl group substituted with a phenyl group”. In other words, the “biphenyl group” is a substituted phenyl group having a C6-C60aryl group as a substituent.

The term “terphenyl group” as used herein refers to “a phenyl group substituted with a biphenyl group”. In other words, the “terphenyl group” is a substituted phenyl group having, as a substituent, a C6-C60aryl group substituted with a C6-C60aryl group.* and *′ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organic light-emitting device according to embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.

EXAMPLES

Synthesis Example 1: Synthesis of Compound BD19

Synthesis of Intermediate [19-A]

4,5-dibromobenzene-1,2-diol (1.0 eq), 1-bromo-3-fluorobenzene (2.6 eq), and K3PO4(4.0 eq) were added to a reaction container, and the mixed solution was suspended in DMF (0.25 M). The reaction mixture was heated, and stirred at a temperature of 160° C. for 24 hours. After the completion of the reaction, the resulting product was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and ethylacetate. An organic layer extracted therefrom was washed with a saturated aqueous NaCl solution, and dried utilizing MgSO4. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain Intermediate [19-A] (yield of 64%).

Synthesis of Intermediate [19-B]

Intermediate [19-A] (1.0 eq), imidazole (5.2 eq), K2CO3(8.0 eq), CuI (0.4 eq), and 1,10-phenanthroline (0.4 eq) were added to a reaction container, and the mixed solution was suspended in DMF (0.25 M). The reaction mixture was heated, and stirred at a temperature of 160° C. for 24 hours. After the completion of the reaction, the resulting product was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and ethylacetate. An organic layer extracted therefrom was washed with a saturated aqueous NaCl solution, and dried utilizing MgSO4. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain Intermediate [19-B] (yield of 68%).

Synthesis of Intermediate [19-C]

Intermediate [19-B] (1.0 eq) and iodomethane-D3(CD3I) (40.0 eq) were added to a reaction container, and the mixed solution was suspended in toluene (0.1 M). The reaction mixture was heated, and stirred at the temperature of 110° C. for 24 hours. After the completion of the reaction, the resulting product was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and ethylacetate. An organic layer extracted therefrom was dried utilizing MgSO4, and the solvent was removed therefrom to obtain Intermediate [19-C] (yield of 89%).

Synthesis of Intermediate [19-D]

Intermediate [19-C] (1.0 eq) was added to a reaction container, and suspended in a mixed solution containing methanol and distilled water at a volume ratio of 2:1. In a sufficiently dissolved state, ammonium hexafluorophosphate (4.4 eq) was slowly added to the reaction solution, and the resulting reaction solution was stirred at room temperature for 24 hours. After completion of the reaction, a resulting solid was filtered and washed with diethyl ether. The washed solid was dried to obtain Intermediate [19-D] (yield of 87%).

Synthesis of Compound BD19

Intermediate [19-D] (1.0 eq), dichloro(1,5-cyclooctadiene)platinum (2.2 eq), and sodium acetate (12.0 eq) were suspended in 1,4-dioxane (0.1 M). The reaction mixture was heated, and stirred at the temperature of 120° C. for 72 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and dichloromethane. An organic layer extracted therefrom was washed with a saturated aqueous NaCl solution, and dried utilizing MgSO4. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain Compound BD19 (yield of 35%).

Synthesis Example 2: Synthesis of Compound BD63

Synthesis of Intermediate [63-A]

1,2-dibromo-4,5-difluorobenzene (1.0 eq), imidazole (3.0 eq), and K3PO4(4.0 eq) were added to a reaction container, and the mixed solution was suspended in DMF (0.25 M). The reaction mixture was heated, and stirred at a temperature of 160° C. for 24 hours. After the completion of the reaction, the resulting product was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and ethylacetate. An organic layer extracted therefrom was washed with a saturated aqueous NaCl solution, and dried utilizing MgSO4. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain Intermediate [63-A] (yield of 70%).

Synthesis of Intermediate [63-B]

2-methoxycarbazole (1.0 eq), 2-bromo-4-(tert-butyl)pyridine (2.6 eq), Pd2(dba)3(0.02 eq), SPhos (0.04 eq), and sodium tert-butoxide (1.6 eq) were added to a reaction container, and the mixed solution was suspended in toluene (0.17 M). The reaction mixture was heated, and stirred at the temperature of 110° C. for 24 hours. After the completion of the reaction, the resulting product was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and ethylacetate. An organic layer extracted therefrom was washed with a saturated aqueous NaCl solution, and dried utilizing MgSO4. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain Intermediate [63-B] (yield of 64%).

Synthesis of Intermediate [63-C]

Intermediate [63-B] (1.0 eq) was suspended in an excessive amount of a mixed solution containing HBr and AcOH at a volume ratio of 2:1. The reaction mixture was heated, and stirred at the temperature of 110° C. for 24 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and an excessive amount of distilled water was added thereto. The resulting solution was then neutralized with an aqueous sodium hydroxide solution and ammonium chloride. A solid precipitated therefrom was filtered, and the filtrate was dissolved in acetone. The resulting product was dried utilizing MgSO4, and the solvent was removed therefrom to obtain Intermediate [63-C] (yield of 90%).

Synthesis of Intermediate [63-D]

Intermediate [63-A] (1.0 eq), Intermediate [63-C] (2.6 eq), K2CO3(4.0 eq), CuI (0.2 eq), and 1,10-phenanthroline (0.2 eq) were added to a reaction container, and the mixed solution was suspended in DMF (0.25 M). The reaction mixture was heated, and stirred at a temperature of 160° C. for 24 hours. After the completion of the reaction, the resulting product was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and ethylacetate. An organic layer extracted therefrom was washed with a saturated aqueous NaCl solution, and dried utilizing MgSO4. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain Intermediate [63-D] (yield of 60%).

Synthesis of Intermediate [63-E]

Intermediate [63-D] (1.0 eq) and iodomethane-D3 (CD3I) (20.0 eq) were added to a reaction container, and the mixed solution was suspended in toluene (0.1 M). The reaction mixture was heated, and stirred at the temperature of 110° C. for 24 hours. After the completion of the reaction, the resulting product was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and ethylacetate. An organic layer extracted therefrom was dried utilizing MgSO4, and the solvent was removed therefrom to obtain Intermediate [63-E] (yield of 92%).

Synthesis of Intermediate [63-F]

Intermediate [63-E] (1.0 eq) was added to a reaction container, and suspended in a mixed solution containing methanol and distilled water at a volume ratio of 2:1. In a sufficiently dissolved state, ammonium hexafluorophosphate (2.2 eq) was slowly added to the reaction solution, and the resulting reaction solution was stirred at room temperature for 24 hours. After completion of the reaction, a resulting solid was filtered and washed with diethyl ether. The washed solid was dried to obtain Intermediate [63-F] (yield of 82%).

Synthesis of Compound BD63

Compound BD63 (yield of 37%) was obtained in the same manner as in the synthesis of Compound BD19, except that Intermediate [63-F] was utilized instead of Intermediate [19-D].

Synthesis Example 3: Synthesis of Compound BD69

Synthesis of Intermediate [69-A]

Intermediate [69-A] (yield of 55%) was obtained in the same manner as in the synthesis of Intermediate [19-A], except that 2-fluoro-1-methylimidazole was utilized instead of imidazole.

Synthesis of Intermediate [69-B]

Intermediate [69-B] was synthesized in the same manner as in the synthesis of Intermediate [63-B].

Synthesis of Intermediate [69-C]

Intermediate [69-C] was synthesized in the same manner as in the synthesis of Intermediate [63-C].

Synthesis of Intermediate [69-D]

Intermediate [69-D] (yield of 62%) was obtained in the same manner as in the synthesis of Intermediate [63-D], except that Intermediate [69-A] was utilized instead of Intermediate [63-A].

Synthesis of Compound BD69

Intermediate [69-D] (1.0 eq), potassium tetrachloroplatinate (2.2 eq), and tetrabutylammonium bromide (0.2 eq) were suspended in AcOH (0.03 M). The reaction mixture was heated, and stirred at the temperature of 110° C. for 72 hours. After the completion of the reaction, the resulting product was cooled to room temperature, and an extraction process was performed thereon utilizing distilled water and dichloromethane. An organic layer extracted therefrom was washed with a saturated aqueous NaCl solution, and dried utilizing MgSO4. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain Compound BD69 (yield of 29%).

Synthesis Example 4: Synthesis of Compound BD87

Synthesis of Intermediate [87-A]

Intermediate [87-A] was synthesized in the same manner as in the synthesis of Intermediate [63-A].

Synthesis of Intermediate [87-B]

Intermediate [87-B] (yield of 60%) was obtained in the same manner as in the synthesis of Intermediate [63-B], except that 2-bromo-1-methyl-1H-imidazole was utilized instead of instead of 2-bromo-4-(tert-butyl)pyridine.

Synthesis of Intermediate [87-C]

Intermediate [87-C] (yield of 87%) was obtained in the same manner as in the synthesis of Intermediate [63-C], except that Intermediate [87-B] was utilized instead of Intermediate [63-B].

Synthesis of Intermediate [87-D]

Intermediate [87-D] (yield of 65%) was obtained in the same manner as in the synthesis of Intermediate [63-D], except that Intermediate [87-C] was utilized instead of Intermediate [63-C].

Synthesis of Intermediate [87-E]

Intermediate [87-E] (yield of 87%) was obtained in the same manner as in the synthesis of Intermediate [63-E], except that Intermediate [87-D] was utilized instead of Intermediate [63-D].

Synthesis of Intermediate [87-F]

Intermediate [87-F] (yield of 85%) was obtained in the same manner as in the synthesis of Intermediate [63-F], except that Intermediate [87-E] was utilized instead of Intermediate [63-E].

Synthesis of Compound BD87

Compound BD87 (yield of 31%) was obtained in the same manner as in the synthesis of Compound BD19, except that Intermediate [87-F] was utilized instead of Intermediate [19-D].

The synthesized compounds were identified by1H NMR and MS/FAB, and results are shown in Table 1 below.

TABLE 1CompoundMS/FABNo.1H NMR (CDCl3, 400 MHz)foundcalc.BD197.00(d, 2H), 7.27(m, 4H),981.01980.227.31(t, 2H), 7.33(d, 2H),7.44(m, 4H)BD631.32(s, 18H), 7.16(m, 4H),1258.471258.347.27(d, 2H), 7.35(t, 2H),7.40(m, 4H), 7.44(d, 2H),7.95(d, 2H), 8.10(d, 2H),8.55(d, 2H), 8.75(d, 2H)BD691.33(s, 18H), 3.72(s, 6H),1253.101252.307.11(d, 2H), 7.13(d, 2H),7.17(m, 4H), 7.35(t, 2H),7.41(m, 4H), 7.94(d, 2H),8.08(d, 2H), 8.56(d, 2H),8.74(d, 2H)BD873.73(s, 6H), 7.11(d, 2H),1152.811152.247.13(d, 2H), 7.16(m, 4H),7.27(d, 2H), 7.35(t, 2H),7.44(d, 2H), 7.94(d, 2H),8.09(d, 2H), 8.55(d, 2H)

Evaluation Example 1

The HOMO energy level and LUMO energy level of each of Compounds BD19, BD63, BD69, BD87, ETH2, and HTH2 were evaluated according to a method described in Table 2, and the results are shown in Table 3.

TABLE 2HOMO energyCyclic voltammetry (CV) (electrolyte: 0.1Mlevel evaluationBu4NPF6/solvent: dimethylforamidemethod(DMF)/electrode: 3-electrode system(working electrode: GC, reference electrode:Ag/AgCl, auxiliary electrode: Pt)) wasutilized to obtain a voltage (V)-current(A) graph for each compound. Then, a HOMOenergy level of each compound was calculatedfrom an oxidation onset of the graph.LUMO energyCyclic voltammetry (CV) (electrolyte: 0.1Mlevel evaluationBu4NPF6/solvent: dimethylforamidemethod(DMF)/electrode: 3-electrode system (workingelectrode: GC, reference electrode: Ag/AgCl,auxiliary electrode: Pt)) was utilized toobtain a voltage (V)-current (A) graph foreach compound. Then, a LUMO energylevel of each compound was calculatedfrom a reduction onset of the graph.

TABLE 3CompoundNo.HOMO (eV)LUMO (eV)BD19−4.55−0.91BD63−4.49−1.37BD69−5.05−1.47BD87−4.41−0.83ETH2−6.44−1.78HTH2−5.67−1.34

Referring to Table 3, it was confirmed that Compounds BD19, BD63, BD69, BD87 ETH2, and HTH2 each have HOMO and LUMO energy levels suitable for the manufacture of an organic light-emitting device.

Example 1

An organic light-emitting device including an emission layer that includes an organometallic complex according to an embodiment was manufactured by the following method.

As an anode, an ITO/Ag/ITO substrate was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with acetone, isopropyl alcohol, and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO substrate was provided to a vacuum deposition apparatus.

Compound 2-TNATA was vacuum-deposited on the ITO substrate to form a hole injection layer having a thickness of 60 nm, and then, NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm.

Compound BD19 (dopant, 10 wt %) was co-deposited with a mixed host including Compounds ETH2 and HTH2 at a weight ratio of 5:5 on the hole transport layer to form an emission layer having a thickness of 30 nm. Subsequently, Compound

ETH2 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 5 nm. Then, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 30 nm, alkali metal halide LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and Al was vacuum-deposited to a thickness of 300 nm to form a LiF/Al electrode, thereby completing the manufacture of an organic light-emitting device.

Example 2 to 4 and Comparative Example 1 to 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, corresponding compounds shown in Table 4 were utilized.

Evaluation Example 2

Regarding the organic light-emitting devices of Examples 1 to 4 and Comparative Examples 1 to 5, the driving voltage (V) at 1,000 cd/m2, current density (mA/cm2), and luminescence efficiency (cd/A) were each measured by utilizing Keithley MU 236 and luminance meter PR650. In addition, the decay time of delayed fluorescence was evaluated based on the time-resolved spectra of the organic light-emitting devices measured by utilizing the Tektronix TDS 460 Four Channel Digitizing Oscilloscope while applying a voltage pulse by utilizing the AVTECCH AV-1011-B pulse generator (wherein a pulse width was between 100 ns and 1 ms), and the results are shown in Table 4.

TABLE 4OrganoDrivingCurrentEmissionmetallicSecondThirdvoltagedensityLuminanceEfficiencywavelengthLifespancompoundcompoundcompound(V)(mA/cm2)(cd/m2)(cd/A)(nm)LT95 (h)Example 1BD19ETH2HTH25.815042978.5949579.9Example 2BD63ETH2HTH25.785042058.4151082.7Example 3BD69ETH2HTH25.625043088.6253187.6Example 4BD87ETH2HTH25.455044108.8249689.1ComparativeBD19ETH2—5.825040918.1349670.4Example 1ComparativeBD19—HTH25.835039808.1649868.1Example 2ComparativeCompound AETH2HTH27.145033107.4247310.3Example 3ComparativeCompound BETH2HTH26.895028457.696067.9Example 4ComparativeCompound CETH2HTH25.505035487.914754.8Example 5

Referring to Table 4, it was confirmed that the organic light-emitting devices of Examples 1 to 4 emitted blue light, and showed high efficiency, long lifespan, and low driving voltage compared to those of the organic light-emitting devices of Comparative Examples 1 to 5.

According to the one or more embodiments, an organic light-emitting device should have high luminescence efficiency, high color purity, and/or a long lifespan.

The use of “may” when describing embodiments of the present invention refers to “one or more embodiments of the present invention.” Also, the term “exemplary” is intended to refer to an example or illustration. It will be understood that when an element or layer is referred to as being “on”, “connected to”, “coupled to”, or “adjacent to” another element or layer, it can be directly on, connected to, coupled to, or adjacent to the other element or layer, or one or more intervening elements or layers may be present. In contrast, when an element or layer is referred to as being “directly on,” “directly connected to”, “directly coupled to”, or “immediately adjacent to” another element or layer, there are no intervening elements or layers present.

As used herein, the term “substantially,” “about,” and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. Moreover, any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein. All such ranges are intended to be inherently described in this specification such that amending to expressly recite any such subranges would comply with the requirements of 35 U.S.C. § 112(a), and 35 U.S.C. § 132(a).

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