Organic metal compound and organic light-emitting device comprising the same

Abstract

Disclosed is an organic metal compound and an organic light-emitting device comprising the same. The organic light-emitting device comprises an organic metal compound and an organic light-emitting device comprising the organic metal compound. 1 (L 1 ) n1 (L 2 ) n2 An organometallic compound represented by 1 The ligand is represented by Formula 1-1: Formula 1-1#imgabs0# In Formula 1-1, *1 to *4 represent 1 The binding position of Z 11 and Z 12 are boron (B) and nitrogen (N), or N and B, respectively. 1 When combined with the α position of the B atom or the N atom, the metal ligand charge transfer in the complex can be improved. An OLED including the organometallic compound can have a long lifetime as well as improved luminous efficiency and color purity.

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0146771 filed on November 23, 2018, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] One or more aspects of example embodiments of the present disclosure are directed to an organic metal compound and an organic light emitting device including the organic metal compound. Background Art

[0003] Organic light emitting devices (OLEDs) are self-emitting devices that can have wide viewing angles, high contrast ratios, and / or short response times. In addition, OLEDs can exhibit high brightness, low driving voltage, and / or high response speed characteristics, and can produce full-color images.

[0004] The example OLED includes a first electrode located on a substrate, and may include a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers (such as holes and electrons) may recombine in the emission layer to generate excitons. These excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0005] One or more aspects of example embodiments of the present disclosure relate to an organic metal compound and an organic light emitting device including the same.

[0006] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.

[0007] One or more example embodiments of the present disclosure provide an organometallic compound represented by Formula 1:

[0008] Formula 1

[0009] M 1 (L 1 ) n1 (L 2 ) n2 ,

[0010] Formula 1-1

[0011]

[0012] Among them, in Formula 1 and Formula 1-1,

[0013] M 1may be selected from the group consisting of first row transition metals, second row transition metals and third row transition metals,

[0014] L 1 It may be a ligand represented by Formula 1-1,

[0015] L 2 can be selected from monodentate ligands and bidentate ligands,

[0016] n1 can be 1,

[0017] n2 can be selected from 0, 1 and 2,

[0018] A 11 To A 16 can be independently selected from C 5 -C 60 Carbocyclic and C 1 -C 60 Heterocyclic group,

[0019] X 11 To X 18 can be independently selected from nitrogen (N) and carbon (C),

[0020] Y 11 To Y 14 may be independently selected from N, C, oxygen (O) and sulfur (S),

[0021] i) Z 11 may be boron (B), and Z 12 Can be N; or ii) Z 11 Can be N, and Z 12 It can be B,

[0022] T 11 To T 14 can be independently selected from a single bond, *-O-*', *-S-*', *-N(R 17 )-*' and *-C(R 17 )(R 18 )-*',

[0023] L 11 To L 13 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 19 )(R 20 )-*'、*-C(R 19 )=*'、*=C(R 19 )-*'、*-C(R 19 )=C(R 20 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R19 )-*'、*-N(R 19 )-*'、*-P(R 19 )-*'、*-Si(R 19 )(R 20 )-*'、*-P(R 19 )(R 20 )-*' and *-Ge(R 19 )(R 20 )-*',

[0024] a11 to a13 may be independently selected from 0, 1, 2 and 3, provided that at least two selected from a11 to a13 are selected from 1, 2 and 3,

[0025] When a11 is 0, A 11 and A 13 They may not be connected to each other; when a12 is 0, A 12 and A 14 may not be connected to each other; and when a13 is 0, A 11 and A 12 may not be connected to each other,

[0026] R 11 To R 20 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),

[0027] From R 11 To R 20 At least two adjacent groups selected from the group consisting of may be optionally combined to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0028] b11 to b16 can be independently selected from 1, 2, 3, 4, 5, 6, 7 and 8,

[0029] Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1-C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,

[0030] *1 to *4 can each independently represent 1 The binding site of

[0031] * and *' both indicate the binding sites with adjacent atoms.

[0032] One or more example embodiments of the present disclosure provide an organic light emitting device including: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer may include an emission layer and an organic metal compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] These and / or other aspects of the exemplary embodiments of the present disclosure will become apparent and more readily understood from the following description taken in conjunction with the accompanying drawings, in which:

[0034] Figure 1 shows a schematic cross-sectional view of an organic light emitting device according to an embodiment of the present disclosure;

[0035] Figure 2 shows a schematic cross-sectional view of an organic light emitting device according to an embodiment of the present disclosure;

[0036] Figure 3 A schematic cross-sectional view showing an organic light emitting device according to an embodiment of the present disclosure; and

[0037] Figure 4 A schematic cross-sectional view of an organic light emitting device according to an embodiment of the present disclosure is shown. DETAILED DESCRIPTION

[0038] Now will be more detailed with reference to the embodiment of its example shown in the accompanying drawings, wherein the same reference numerals always represent the same element, and its repeated description may not be provided. In this regard, the present embodiment may have different forms, and should not be construed as being limited to the description set forth herein. Therefore, the following only explains the aspects of this description by describing the embodiment with reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more related listed items. When the expressions such as "at least one (kind) (person) in ... ", "one (kind) (person) in ... " and "select from ... " are after a column of elements (elements), the elements (elements) of the entire column are modified, and the individual elements (elements) in the column are not modified. In addition, when describing the embodiments of the present disclosure, "may (may)" is used to represent "one or more embodiments of the present disclosure".

[0039] Since the present disclosure allows various changes and a large number of embodiments, selected embodiments will be shown in the drawings and described in more detail in the written description. By referring to the example embodiments of the present disclosure based on the drawings, the effects, features and methods of implementing the present disclosure will be obvious. However, the present disclosure can be implemented in many different forms and should not be interpreted as being limited to the embodiments set forth herein.

[0040] In the embodiments described in this specification, unless explicitly stated and / or alternative forms have clearly different meanings in the context, expressions used in the singular form include expressions in the plural form, and vice versa.

[0041] In the present specification, it will be understood that terms such as “include”, “have” and “comprising” are intended to indicate the presence of features or components disclosed in the specification, and are not intended to exclude the possibility that one or more other features or components may exist and / or may be added.

[0042] It will be understood that when a layer, region, or component is referred to as being "on," "over," or "onto" another layer, region, or component, the layer, region, or component may be formed directly or indirectly over the other layer, region, or component. In some embodiments, for example, there may be intervening layers, regions, or components. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.

[0043] For clarity and convenience of explanation, the sizes of components in the drawings (e.g., thickness of layers, films, panels, regions, etc.) may be exaggerated. In other words, since the sizes and thicknesses of components in the drawings are arbitrarily shown for convenience of explanation, the following embodiments are not limited thereto.

[0044] The organometallic compound can be represented by Formula 1:

[0045] Formula 1

[0046] M 1 (L 1 ) n1 (L 2 ) n2 ,

[0047] Among them, in formula 1, M 1 It can be selected from the first row transition metals, the second row transition metals and the third row transition metals.

[0048] For example, in Formula 1, M 1 It can be selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm), but the embodiments of the present disclosure are not limited thereto.

[0049] In some embodiments, in Formula 1, M 1 It may be selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, and Os, but the embodiments of the present disclosure are not limited thereto.

[0050] In some embodiments, in Formula 1, M 1 It may be selected from Pt and Pd, but the embodiments of the present disclosure are not limited thereto.

[0051] In formula 1, L 1 It may be a ligand represented by formula 1-1:

[0052] Formula 1-1

[0053]

[0054] In formula 1-1, A 11 To A 16 can be independently selected from C 5 -C 60 Carbocyclic and C 1 -C 60 Heterocyclic group.

[0055] In some embodiments, in Formula 1-1, A 11 and A 12 can be independently selected from C 5 -C 60 Carbocyclic and C 1 -C 60 a heterocyclic group, and

[0056] A 13 To A 16 can be independently selected from C5 -C 60 A carbocyclic group, but the embodiments of the present disclosure are not limited thereto.

[0057] In some embodiments, in Formula 1-1, A 11 To A 16 can be independently selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, phenanthrenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, cyclopentadienyl, tetrahydronaphthyl, furanyl, thienyl, thirolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirolyl, dibenzothirolyl, indenopyridyl, indolopyridyl, benzofuranopyridyl, benzothienopyridyl, benzothiazolinyl, indenopyridyl, indolopyridyl, benzofuranopyridyl, benzothienopyridyl, benzothiazolinyl, indenopyrimidinyl, indolopyrimidinyl, benzofuranopyrimidinyl, benzothienopyrimidinyl, benzothiazolinyl, dihydropyridyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenanthroline The invention also includes benzopyrazolyl, benzoimidazolyl, dihydrobenzimidazolyl, imidazopyridyl, dihydroimidazopyridyl, imidazopyrimidinyl, dihydroimidazopyrimidinyl, imidazopyrazinyl, dihydroimidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, tetrahydroisoquinolinyl, and tetrahydroquinolinyl, but the embodiments of the present disclosure are not limited thereto.

[0058] In some embodiments, in Formula 1-1, A 11 To A 16 They may be independently selected from phenyl, naphthyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, pyrazolyl, imidazolyl, dihydroimidazolyl, triazolyl, dihydrotriazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, dihydrobenzimidazolyl, dihydroimidazopyridinyl, dihydroimidazopyrimidinyl, dihydroimidazopyrazinyl, benzoxazolyl and benzothiazolyl, but the embodiments of the present disclosure are not limited thereto.

[0059] In some embodiments, in Formula 1-1, A 11 To A 16 Each may be independently represented by one selected from Formula 2-1 to Formula 2-43, but the embodiments of the present disclosure are not limited thereto:

[0060]

[0061]

[0062] In Formula 2-1 to Formula 2-43,

[0063] X 21 To X 23 can be independently selected from C(R 24 ) and C-*, provided that from X 21 To X 23 At least two of the selected ones are C-*,

[0064] X 24 Can be N-*, and X 25 and X 26 can be independently selected from C(R 24 ) and C-*, provided that from X 25 and X 26 At least one of the selected is C-*,

[0065] X 27 and X 28 can be independently selected from O, S, C(R 24 )、N、N(R 25 ) and N-*; and X 29 Can be selected from O, S, C (R 24 ) and C-*, provided that i) from X 27 and X 28 At least one of the selected ones is N-*, and X 29 C-*, or ii) X 27 and X 28 are all N-*, and X 29 Selected from O, S and C (R 24 ),

[0066] R 21 To R 25 can be independently connected to R in Formula 1 11 Defined similarly,

[0067] b21 can be selected from 1, 2 and 3,

[0068] b22 can be selected from 1, 2, 3, 4 and 5,

[0069] b23 can be selected from 1, 2, 3 and 4,

[0070] b24 can be selected from 1 and 2, and

[0071] *Indicates the binding site with the adjacent atom.

[0072] In some embodiments, in Formula 1-1, A 11 and A 12 can be independently selected from indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, pyrazolyl, imidazolyl, dihydroimidazolyl, triazolyl, dihydrotriazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, dihydrobenzimidazolyl, dihydroimidazopyridinyl, dihydroimidazopyrimidinyl, dihydroimidazopyrazinyl, benzoxazolyl and benzothiazolyl, and

[0073] A 13 To A 16 The groups may be independently selected from phenyl, naphthyl, indenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl and dibenzothienyl, but the embodiments of the present disclosure are not limited thereto.

[0074] In some embodiments, in Formula 1-1, A 13 To A 16 Each may independently be a phenyl group, but the embodiments of the present disclosure are not limited thereto.

[0075] In formula 1-1, X 11 To X 18 can be independently selected from N and C.

[0076] In some embodiments, in Formula 1-1, X 11 To X 18 They may all be C, but the embodiments of the present disclosure are not limited thereto.

[0077] In formula 1-1, Y 11 To Y 14 can be independently selected from N, C, O and S.

[0078] In some embodiments, in Formula 1-1, Y 11 To Y 14 They may be independently selected from N and C, but the embodiments of the present disclosure are not limited thereto.

[0079] In some embodiments, in Formula 1-1, Y 11 and Y 12 They may all be C, but the embodiments of the present disclosure are not limited thereto.

[0080] In formula 1-1, i) Z 11 can be B, and Z 12 Can be N, or ii) Z 11 Can be N, and Z 12It can be B. In formula 1-1, T 11 To T 14 can be independently selected from a single bond, *-O-*', *-S-*', *-N(R 17 )-*' and *-C(R 17 )(R 18 )-*'. R 17 and R 18 As described below.

[0081] In some embodiments, in Formula 1-1, T 11 To T 14 All may be single bonds, but the embodiments of the present disclosure are not limited thereto.

[0082] In formula 1-1, L 11 To L 13 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 19 )(R 20 )-*'、*-C(R 19 )=*'、*=C(R 19 )-*'、*-C(R 19 )=C(R 20 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 19 )-*'、*-N(R 19 )-*'、*-P(R 19 )-*'、*-Si(R 19 )(R 20 )-*'、*-P(R 19 )(R 20 )-*' and *-Ge(R 19 )(R 20 )-*'. R 19 and R 20 As described below.

[0083] In some embodiments, in Formula 1-1, L 11 To L 13 All may be single bonds, but the embodiments of the present disclosure are not limited thereto.

[0084] In formula 1-1, a11 to a13 can represent L 11 To L 13 a11 to a13 may be independently selected from 0, 1, 2 and 3, provided that at least two selected from a11 to a13 are selected from 1, 2 and 3. When any one of a11 to a13 is 2 or greater, at least two L 11 To L 13Each of them can be the same or different from each other. When a11 is 0, A 11 and A 13 They may not be connected to each other. When a12 is 0, A 12 and A 14 They may not be connected to each other. When a13 is 0, A 11 and A 12 May not be connected to each other.

[0085] In some embodiments, in Formula 1-1, a11 and a12 may be selected from 1, 2, and 3, but the embodiments of the present disclosure are not limited thereto.

[0086] In some embodiments, in Formula 1-1, a13 may be 0 or 1, but the embodiments of the present disclosure are not limited thereto.

[0087] In formula 1-1, R 11 To R 20 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ). In some embodiments, from R 11 To R 20 At least two adjacent groups selected from the group consisting of may be optionally combined to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group.

[0088] For R 11 To R 20 , Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group.

[0089] In some embodiments, in Formula 1-1, R 11 To R 20 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0090] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl and terphenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0091] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzosilyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, and indolocarbazolyl;

[0092] All are substituted with deuterium, -F, -Cl, -Br, -I, cyano, C1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazole yl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, indolocarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32 ) is at least one selected from cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, oxazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothiophenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothiophenyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothiophenyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, and indolocarbazolyl; and

[0093] -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),

[0094] Among them, Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 A heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, but the embodiments of the present disclosure are not limited thereto.

[0095] In some embodiments, in Formula 1-1, R 11 To R 20 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano and C 1 -C 20 alkyl;

[0096] C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and cyano 1 -C 20 alkyl;

[0097] A group represented by Formula 5-1 to Formula 5-138; and

[0098] -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), but the embodiments of the present disclosure are not limited thereto:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] In equations 5-1 to 5-138,

[0106] X 51 Can be selected from O, S, N (R 51 ) and C(R 51 )(R 60 ),

[0107] X 52 Can be N or C (R 52 ), X 53 Can be N or C (R 53 ), X 54 Can be N or C (R 54 ), X 55 Can be N or C (R 55 ), X 56 Can be N or C (R 56 ), X 57 Can be N or C (R 57 ), X 58 Can be N or C (R 58 ), and X 59 Can be N or C (R 59 ),

[0108] R 51 To R 60 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, thienyl, furyl, thiols, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, benzothiols, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiols, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31)、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32 ),

[0109] Among them, Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from C 1 -C 60 Alkyl, phenyl, biphenyl and terphenyl,

[0110] b51 can be selected from 1, 2, 3, 4 and 5,

[0111] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,

[0112] b53 can be selected from 1, 2, 3, 4, 5, 6, 7, 8 and 9,

[0113] b54 can be selected from 1, 2, 3 and 4,

[0114] b55 can be selected from 1, 2 and 3,

[0115] b56 can be selected from 1 and 2,

[0116] b57 may be selected from 1, 2, 3, 4, 5 and 6, and

[0117] *Indicates the binding site with the adjacent atom.

[0118] In some embodiments, in Formula 1-1, R 11 To R 20 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano and C 1 -C 20 alkyl;

[0119] C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and cyano 1 -C 20 Alkyl; and

[0120] The group represented by Formula 5-1, but the embodiments of the present disclosure are not limited thereto.

[0121] In some embodiments, in Formula 1-1, R 11 and R 12can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano and C 1 -C 20 alkyl;

[0122] C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and cyano 1 -C 20 Alkyl; and

[0123] A group represented by formula 5-1, and

[0124] R 13 To R 16 All may be hydrogen, but the embodiments of the present disclosure are not limited thereto.

[0125] In some embodiments, in Formula 1-1, R 11 To R 20 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl;

[0126] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, each of which is substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and cyano; and

[0127] The groups represented by Formula 6-1 to Formula 6-257, but the embodiments of the present disclosure are not limited thereto:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] In equations 6-1 to 6-257,

[0139] "i-Pr" means isopropyl,

[0140] "t-Bu" means tert-butyl,

[0141] "Ph" means phenyl,

[0142] "1-Naph" means 1-naphthyl,

[0143] "2-Naph" means 2-naphthyl, and

[0144] *Indicates the binding site with the adjacent atom.

[0145] In some embodiments, in Formula 1-1, R 11 To R 16 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl;

[0146] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, each of which is substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and cyano; and

[0147] The groups represented by Formula 6-1 to Formula 6-110, but the embodiments of the present disclosure are not limited thereto.

[0148] In some embodiments, in Formula 1-1, R 11 and R 12 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl;

[0149] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, each of which is substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and cyano; and

[0150] The groups represented by Formula 6-1 to Formula 6-31, but the embodiments of the present disclosure are not limited thereto.

[0151] In some embodiments, in Formula 1-1, R 13 To R 16 All may be hydrogen, but the embodiments of the present disclosure are not limited thereto.

[0152] In formula 1-1, b11 to b16 can represent R 11 To R 16 b11 to b16 may be independently selected from 1, 2, 3, 4, 5, 6, 7 and 8. When any one of b11 to b16 is 2 or greater, at least two R 11To R 16 The respective ones may be the same as or different from each other.

[0153] In Formula 1-1, *1 to *4 may be independently 1 The combination position.

[0154] In Formula 1-1, * and *' both represent the bonding site with the adjacent atom.

[0155] In some embodiments, in Formula 1, L 1 It may be a ligand represented by one selected from Formula 1-11 and Formula 1-12, but the embodiments of the present disclosure are not limited thereto:

[0156] Formula 1-11

[0157]

[0158] Formula 1-12

[0159]

[0160] In formula 1-11 and formula 1-12,

[0161] *1 to *4, A 11 To A 16 , Y 11 To Y 14 , L 11 , L 12 、a11、a12、R 11 To R 16 And b11 to b16 may each independently be the same as defined in combination with Formula 1-1.

[0162] In some embodiments, in Formula 1, L 1 It may be a ligand represented by one selected from Formula 1-21 and Formula 1-22, but the embodiments of the present disclosure are not limited thereto:

[0163] Formula 1-21

[0164]

[0165] Formula 1-22

[0166]

[0167] In Formula 1-21 and Formula 1-22,

[0168] *1 to *4, A 11 , A 12 , A 15 , A 16 , Y 11 To Y 14, L 11 , L 12 、a11、a12、R 11 To R 16 And b11 to b16 may each independently be the same as defined in combination with Formula 1-1.

[0169] In some embodiments, L 1 It may be a ligand represented by one selected from Formula 1-31 and Formula 1-32, but the embodiments of the present disclosure are not limited thereto:

[0170] Formula 1-31

[0171]

[0172] Formula 1-32

[0173]

[0174] In Formula 1-31 and Formula 1-32,

[0175] *1 to *4, A 11 , A 12 , Y 13 , Y 14 , L 11 , L 12 、a11、a12、R 11 , R 12 and b11 and b12 may each be independently defined as the same as defined in conjunction with formula 1-1, and

[0176] R 13a , R 13b , R 14a , R 14b , R 15a To R 15d and R 16a To R 16d can be independently combined with R in formula 1-1 13 same.

[0177] In formula 1, L 2 It can be selected from monodentate ligands and bidentate ligands.

[0178] In some embodiments, in Formula 1, L 2 It may be a ligand represented by one selected from Formula 7-1 to Formula 7-11, but the embodiments of the present disclosure are not limited thereto:

[0179]

[0180] In equations 7-1 to 7-11,

[0181] A71 and A 72 can be independently selected from C 5 -C 20 Carbocyclic and C 1 -C 20 Heterocyclic group,

[0182] X 71 and X 72 may be independently selected from C and N,

[0183] X 73 Can be N or C (Q 73 ), X 74 Can be N or C (Q 74 ), X 75 Can be N or C (Q 75 ), X 76 Can be N or C (Q 76 ), and X 77 Can be N or C (Q 77 ),

[0184] X 78 Can be O, S or N (Q 78 ), and X 79 Can be O, S or N (Q 79 ),

[0185] Y 71 and Y 72 can be independently selected from single bonds, double bonds, substituted or unsubstituted C 1 -C 5 Alkylene, substituted or unsubstituted C 2 -C 5 Alkenylene and substituted or unsubstituted C 6 -C 10 Arylene,

[0186] Z 71 and Z 72 can be independently selected from N, O, N(R 75 )、P(R 75 )(R 76 ) and As(R 75 )(R 76 ),

[0187] Z 73 Can be selected from P and As,

[0188] Z 74 can be selected from CO (e.g., carbonyl moiety, C(=O)) and C(R 75 )(R 76 ),

[0189] R 71 To R 73 , R 75 To R 80 and Q 73 To Q 79 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein R 71 and R 72 may optionally combine to form a ring, R 77 and R 78 may optionally combine to form a ring, R 78 and R 79 may optionally combine to form a ring, and R 79 and R 80 may optionally be combined to form a ring,

[0190] b71 and b72 can be independently selected from 1, 2 and 3, and

[0191] * and *' both indicate the binding sites with adjacent atoms.

[0192] In some embodiments, in Formula 7-11, A 71and A 72 Each of the groups may be independently selected from a phenyl group, a naphthyl group, an imidazolyl group, a benzimidazolyl group, a pyridyl group, a pyrimidinyl group, a triazine group, a quinolyl group, and an isoquinolyl group, but the embodiments of the present disclosure are not limited thereto.

[0193] In some embodiments, in Formula 7-11, X 72 and X 79 They may all be N, but the embodiments of the present disclosure are not limited thereto.

[0194] In some embodiments, in Formula 7-7, X 73 It can be C(Q 73 ), X 74 It can be C(Q 74 ), X 75 It can be C(Q 75 ), X 76 It can be C(Q 76 ), and X 77 It can be C(Q 77 ), but the embodiments of the present disclosure are not limited thereto.

[0195] In some embodiments, in Formulas 7-8, X 78 It can be N(Q 78 ), and X 79 It can be N(Q 79 ), but the embodiments of the present disclosure are not limited thereto.

[0196] In some embodiments, in Formula 7-2, Formula 7-3, and Formula 7-8, Y 71 and Y 72 The groups may each be independently selected from a substituted or unsubstituted methylene group and a substituted or unsubstituted phenylene group, but the embodiments of the present disclosure are not limited thereto.

[0197] In some embodiments, in Formula 7-1 and Formula 7-2, Z 71 and Z 72 They can all be 0, but the embodiments of the present disclosure are not limited thereto.

[0198] In some embodiments, in Formula 7-4, Z 73 It can be P, but the embodiments of the present disclosure are not limited thereto.

[0199] In some embodiments, in Formula 7-1 to Formula 7-8, R 71 To R 73 , R 75 To R 80 and Q 73 To Q 79can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0200] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, naphthyl, pyridyl and pyrimidyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0201] Phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, and imidazopyridinyl;

[0202] All are substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, at least one selected from the group consisting of phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranyl, benzo[9,10]phenanthryl, pyrenyl, pyrenyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl and imidazopyridinyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, The invention also includes but is not limited to benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, and imidazopyridyl, but the embodiments of the present disclosure are not limited thereto.

[0203] In some embodiments, in Formula 1, L 2 It may be a ligand represented by one selected from Formula 8-1 to Formula 8-11, but the embodiments of the present disclosure are not limited thereto:

[0204]

[0205] In Formulae 8-1 to 8-11, * represents a bonding site with an adjacent atom.

[0206] In formula 1, n1 represents L 1 , and n1 can be 1.

[0207] In formula 1, n2 represents L 2 , and n2 can be selected from 0, 1 and 2.

[0208] In some embodiments, in Formula 1, n1 may be 1, and n2 may be 0, but embodiments of the present disclosure are not limited thereto.

[0209] In some embodiments, in Formula 1, n1 may be 1, and n2 may be 1 or 2, but embodiments of the present disclosure are not limited thereto.

[0210] In some embodiments, in Formula 1, M 1may be selected from Pt and Pd, n1 may be 1, and n2 may be 0, but the embodiments of the present disclosure are not limited thereto.

[0211] In some embodiments, the organometallic compound represented by Formula 1 may be selected from Compound 1 to Compound 240, but the embodiments of the present disclosure are not limited thereto:

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224] In Compound 1 to Compound 240, "Ph" represents a phenyl group.

[0225] The organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength of about 450 nm or more and less than 490 nm.

[0226] The organic metal compound represented by Formula 1 includes an azahydrocarbyl boron moiety. When the organic metal compound represented by Formula 1 is included in the emission layer of the organic light-emitting device, the formation of excimers and exciplexes with the host can be suppressed. Therefore, the color purity and life of the organic light-emitting device including the organic metal compound can be improved.

[0227] In the organometallic compound represented by Formula 1, the metal atom may be combined with the α-position of the boron (B) atom or the nitrogen (N) atom. In this way, the metal ligand charge transfer in the complex may be improved. Therefore, the luminous efficiency and life of the organic light-emitting device including the organometallic compound may be improved.

[0228] In the organometallic compound represented by Formula 1, B and N may be directly connected to each other through a single bond, and the organometallic compound may have a polycyclic structure in which B atoms and N atoms are surrounded by a ring. Therefore, the organometallic compound may have improved structural durability. Therefore, an organic light-emitting device including the organometallic compound may have improved luminous efficiency.

[0229] The organometallic compound represented by Formula 1 may be synthesized using any suitable organic synthesis method. The method of synthesizing the organometallic compound may be understood by one of ordinary skill in the art by referring to the examples described herein.

[0230] At least one organic metal compound represented by Formula 1 may be included between a pair of electrodes in an organic light emitting device. In some embodiments, the organic metal compound may be included in at least one selected from a hole transport region, an electron transport region, and an emission layer.

[0231] In some embodiments, the organometallic compound represented by Formula 1 may be used as a material for forming a capping layer positioned on the outside of one or both sides of a pair of electrodes in an organic light-emitting device.

[0232] In some embodiments, the emission layer may include an organic metal compound, but embodiments of the present disclosure are not limited thereto.

[0233] In some embodiments, the emission layer may include a host and an organic metal compound, and an amount of the host in the emission layer may be greater than an amount of the organic metal compound in the emission layer, but embodiments of the present disclosure are not limited thereto.

[0234] As used herein, expressions such as “at least one organic metal compound represented by Formula 1” and “(layer) may include at least one organic metal compound” mean “(organic layer) may include one organic metal compound of Formula 1, or may include two or more different organic metal compounds of Formula 1”.

[0235] For example, a single organometallic compound referred to as Compound 1 may be included in an organic layer. In this embodiment, Compound 1 may be included in an emission layer of an organic light-emitting device. In some embodiments, two organometallic compounds referred to as Compound 1 and Compound 2 may both be included in an organic layer. In this embodiment, Compound 1 and Compound 2 may be present in the same layer (e.g., Compound 1 and Compound 2 may both (e.g., simultaneously) be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport layer).

[0236] The organic layer may include: i) a hole transport region located between the first electrode (anode) and the emission layer, the hole transport region may include at least one selected from a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer, and ii) an electron transport region located between the emission layer and the second electrode (cathode), the electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer. The emission layer may include at least one organic metal compound represented by Formula 1.

[0237] The term "organic layer" as used herein may refer to a single layer and / or multiple layers between a first electrode and a second electrode in an organic light emitting device. Materials included in the "organic layer" are not limited to organic materials.

[0238] Figure 1 Description

[0239] Figure 1 is a schematic diagram of an organic light emitting device 10 according to an exemplary embodiment of the present disclosure. The organic light emitting device 10 may include a first electrode 110 , an organic layer 150 , and a second electrode 190 .

[0240] In the following, we will combine Figure 1 A structure of an organic light emitting device 10 according to an embodiment of the present disclosure and a method of manufacturing the organic light emitting device 10 according to an embodiment of the present disclosure are described.

[0241] First electrode 110

[0242] exist Figure 1 In the embodiment, a substrate may be disposed below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate and / or a plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or waterproofness.

[0243] The first electrode 110 may be formed by depositing and / or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.

[0244] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and combinations thereof, but the embodiments of the present disclosure are not limited thereto. In some embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, at least one selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and combinations thereof may be used as a material for forming the first electrode 110, but the embodiments of the present disclosure are not limited thereto.

[0245] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. In some embodiments, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto.

[0246] Organic layer 150

[0247] The organic layer 150 may be located on the first electrode 110. The organic layer 150 may include an emission layer.

[0248] In some embodiments, the organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and / or an electron transport region between the emission layer and the second electrode 190 .

[0249] Hole transport region in the organic layer 150

[0250] The hole transport region may have: i) a single layer structure including a single layer including a single material, ii) a single layer structure including a single layer including a plurality of different materials, or iii) a multilayer structure having a plurality of layers including a plurality of different materials.

[0251] The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.

[0252] For example, the hole transport region may have a single-layer structure or a multi-layer structure, wherein the single-layer structure includes a single layer comprising a plurality of different materials, and the multi-layer structure is, for example, a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein the layers of each structure are sequentially stacked on the first electrode 110 in each stated order, but the embodiments of the present disclosure are not limited thereto.

[0253] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

[0254]

[0255] Formula 201

[0256]

[0257] Formula 202

[0258]

[0259] In equation 201 and equation 202,

[0260] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0261] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2 -C 20 Alkenylene, substituted or unsubstituted C 3 -C10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0262] xa1 to xa4 may each independently be an integer from 0 to 3,

[0263] xa5 can be an integer from 1 to 10, and

[0264] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0265] In some embodiments, in Formula 202, R 201 and R 202 may be optionally linked via a single bond, a dimethyl-methylene or a diphenyl-methylene, R 203 and R 204 The attachment may alternatively be via a single bond, a dimethyl-methylene or a diphenyl-methylene.

[0266] In some embodiments, in Equation 201 and Equation 202, L 201To L 205 Can be independently selected from:

[0267] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridinylene; and

[0268] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one selected from phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene and pyridylene,

[0269] Among them, Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0270] In some embodiments, xa1 to xa4 may each independently be 0, 1 or 2.

[0271] In some embodiments, xa5 can be 1, 2, 3 or 4.

[0272] In some embodiments, R 201 To R 204 and Q 201 can be independently selected from phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and

[0273] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one selected from phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl,

[0274] Among them, Q 31 To Q 33 May all be the same as described herein.

[0275] In some embodiments, in Formula 201, from R 201 To R 203 At least one of the selected ones can be independently selected from:

[0276] fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and

[0277] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Phenyl of an alkyl group, phenyl substituted with -F, naphthyl, fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, but the embodiments of the present disclosure are not limited thereto, and at least one selected from the group consisting of fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0278] In some embodiments, in Formula 202, i) R 201 and R 202can be connected via a single bond, and / or ii) R 203 and R 204 Can connect via one-touch.

[0279] In some embodiments, in Formula 202, from R 201 To R 204 At least one of the selected ones may be selected from:

[0280] carbazolyl; and

[0281] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 A phenyl group of an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, but the embodiments of the present disclosure are not limited thereto.

[0282] In some embodiments, the compound represented by Formula 201 can be further represented by Formula 201A:

[0283] Formula 201A

[0284]

[0285] In some embodiments, the compound represented by Formula 201 may be further represented by Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:

[0286] Formula 201A(1)

[0287]

[0288] In some embodiments, the compound represented by Formula 201 may be further represented by Formula 201A-1, but embodiments of the present disclosure are not limited thereto:

[0289] Formula 201A-1

[0290]

[0291] In some embodiments, the compound represented by Formula 202 can be further represented by Formula 202A:

[0292] Formula 202A

[0293]

[0294] In some embodiments, the compound represented by Formula 202 can be further represented by Formula 202A-1:

[0295] Formula 202A-1

[0296]

[0297] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1, L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 may be the same as described herein,

[0298] R 211 and R 212 Can be combined with R 203 The same, and

[0299] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl.

[0300] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT39, but the embodiments of the present disclosure are not limited thereto:

[0301]

[0302]

[0303]

[0304]

[0305] The thickness of the hole transport region can be about 100 angstroms. to about For example, about to about When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to about For example, about to about At the same time, the thickness of the hole transport layer can be about to about For example, about to about When the thickness of the hole transport region, the hole injection layer, and / or the hole transport layer is within any of these ranges, excellent hole transport characteristics may be obtained without significantly increasing the driving voltage.

[0306] The emission-assisting layer can improve the luminous efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer (for example, by adjusting the optical resonance distance in the device to match the wavelength of the light emitted from the emission layer). The electron blocking layer can reduce or eliminate the flow of electrons from the electron transport region. The emission-assisting layer and the electron blocking layer can both include the aforementioned materials.

[0307] p-dopant

[0308] In addition to the aforementioned materials, the hole transport region may also include a charge generating material to improve the conductive properties of the hole transport region. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region.

[0309] The charge generating material may be, for example, a p-dopant.

[0310] In some embodiments, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.

[0311] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments of the present disclosure are not limited thereto.

[0312] In some embodiments, the p-dopant may be selected from quinone derivatives such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0313] Metal oxides (such as tungsten oxide and / or molybdenum oxide);

[0314] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and

[0315] A compound represented by Formula 221, but embodiments of the present disclosure are not limited thereto:

[0316]

[0317] Formula 221

[0318]

[0319] In formula 221,

[0320] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein R 221 To R 223 At least one selected from cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted with -Cl 1 -C 20 Alkyl, C substituted with -Br 1 -C 20 Alkyl and C substituted with -I 1 -C 20 At least one substituent selected from the group consisting of:

[0321] Emission layer in the organic layer 150

[0322] When the organic light emitting device 10 is a full-color organic light emitting device, the emission layer can be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure. The stacked structure may include two or more layers selected from a red emission layer, a green emission layer and a blue emission layer. In some embodiments, the two or more layers may be in direct contact with each other. In some embodiments, the two or more layers may be separated from each other. In one or more embodiments, the emission layer may include two or more materials. The two or more materials may include a red light emitting material, a green light emitting material and / or a blue light emitting material. In some embodiments, the two or more materials may be mixed with each other in a single layer. The two or more materials mixed with each other in a single layer may emit white light.

[0323] The emission layer may include a host and a dopant. The dopant may include an organic metal compound represented by Formula 1. In some embodiments, in addition to the organic metal compound represented by Formula 1, the dopant may further include at least one of a phosphorescent dopant and a fluorescent dopant.

[0324] The amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0325] The thickness of the emission layer can be about to about In some embodiments, about to about When the thickness of the emission layer is within these ranges, improved light emitting characteristics may be obtained without significantly increasing driving voltage.

[0326] Subject in the emission layer

[0327] The host may include a compound represented by Formula 301:

[0328] Formula 301

[0329] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0330] In formula 301,

[0331] Ar 301 Can be selected from substituted or unsubstituted C 5 -C 60 Carbocyclic group and substituted or unsubstituted C 1 -C60 Heterocyclic group,

[0332] xb11 can be 1, 2 or 3,

[0333] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0334] xb1 can be an integer from 0 to 5.

[0335] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) and -P(=O)(Q 301 )(Q 302 ),and

[0336] xb21 can be an integer from 1 to 5,

[0337] Among them, Q 301 To Q 303 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0338] In some embodiments, in Formula 301, Ar 301 Can be selected from:

[0339] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, phenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and

[0340] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31)(Q 32 ) is at least one of naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, peryl, pentaphenyl, indenoanthryl, dibenzofuranyl and dibenzothiophenyl,

[0341] Among them, Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0342] When xb11 in Formula 301 is 2 or greater, at least two Ar 301 Can be connected (joined) via a single bond.

[0343] In one or more embodiments, the compound represented by Formula 301 may be further represented by Formula 301-1 or Formula 301-2:

[0344] Formula 301-1

[0345]

[0346] Formula 301-2

[0347]

[0348] In Formula 301-1 and Formula 301-2,

[0349] A 301 To A 304 can be independently selected from phenyl, naphthyl, phenanthrenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyridyl, pyrimidyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthothienyl, benzonaphthothienyl and dinaphthothienyl,

[0350] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0351] R 311 To R 314can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0352] xb22 and xb23 can each independently be 0, 1 or 2,

[0353] L 301 、xb1、R 301 and Q 31 To Q 33 may all be the same as described herein,

[0354] L 302 To L 304 can be independently 301 same,

[0355] xb2 to xb4 may each independently be the same as xb1, and

[0356] R 302 To R 304 can be independently related to R 301 same.

[0357] In some embodiments, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:

[0358] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and

[0359] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32) is at least one of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene, yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene , pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene,

[0360] Among them, Q 31 To Q 33 May all be the same as described herein.

[0361] In some embodiments, in Formula 301, Formula 301-1, and Formula 301-2, R 301 To R 304 Can be independently selected from:

[0362] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0363] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl,

[0364] Among them, Q 31 To Q 33 May all be the same as described herein.

[0365] In some embodiments, the host may include an alkaline earth metal complex. For example, the host may include a beryllium (Be) complex (e.g., compound H55) or a magnesium (Mg) complex. In some embodiments, the host may include a zinc (Zn) complex.

[0366] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), 4-((1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA), and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:

[0367]

[0368]

[0369]

[0370]

[0371] In some embodiments, the host may include at least one selected from a silicon-containing compound (eg, BCPDS, etc., as used in the example) and a phosphine oxide-containing compound (eg, POPCPA, etc., as used in the example).

[0372] The host may include one or a class of compounds, or in some embodiments, may include two or more different species or classes of compounds (eg, an example includes BCPDS and POPCPA as a host). As such, the embodiments of the present disclosure may be modified in various ways.

[0373] The phosphorescent dopant included in the emission layer of the organic layer 150

[0374] The phosphorescent dopant may include an organic metal compound represented by Formula 1.

[0375] In some embodiments, in addition to the organometallic compound represented by Formula 1, the phosphorescent dopant may further include an organometallic complex represented by Formula 401:

[0376] Formula 401

[0377] M(L 401 ) xc1(L 402 ) xc2 ,

[0378] Formula 402

[0379]

[0380] In equations 401 and 402,

[0381] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),

[0382] L 401 can be selected from the ligand represented by formula 402, and xc1 can be 1, 2 or 3; wherein, when xc1 is 2 or greater, at least two L 401 can be the same or different from each other,

[0383] L 402 may be an organic ligand, and xc2 may be an integer selected from 0 to 4; wherein, when xc2 is 2 or greater, at least two L 402 can be the same or different from each other,

[0384] X 401 To X 404 may each independently be a nitrogen atom (N) or a carbon atom (C),

[0385] X 401 and X 403 can be connected to each other via single bonds or double bonds, and X 402 and X 404 can be linked to each other via single or double bonds,

[0386] A 401 and A 402 can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0387] X 405 It can be selected from a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*' and *=C=*', where Q 411 and Q412 Can be selected from hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl,

[0388] X 406 Can be a single bond, O or S,

[0389] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 1 -C 20 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C10 Alkoxy, C 6 -C 20 Aryl and C 1 -C 20 Heteroaryl,

[0390] xc11 and xc12 may each independently be an integer from 0 to 10, and

[0391] The * and *' in formula 402 both represent the binding site with M in formula 401.

[0392] In some embodiments, in Formula 402, A 401 and A 402 They can all be independently selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiophenyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl.

[0393] In one or more embodiments, in Formula 402, i) X 401 may be nitrogen, and X 402 It can be carbon, or ii) X 401 and X 402 Both (eg, simultaneously) may be nitrogen.

[0394] In some embodiments, in Formula 402, R 401 and R 402 Can be independently selected from:

[0395] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0396] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0397] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;

[0398] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 at least one selected from the group consisting of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

[0399] -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ),

[0400] Among them, Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0401] In one or more embodiments, when xc1 in equation 401 is 2 or greater, at least two L 401 Two A's 401 It can be optionally connected via X as a linker 407 Connect, or two A 402 It can be optionally connected via X as a linker408 Connection (see, for example, Compound PD1 to Compound PD4 and Compound PD7). 407 and X 408 can be independently selected from a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*'、*-C(Q 413 )(Q 414 )-*' and *-C(Q 413 )=C(Q 414 )-*', where Q 413 and Q 414 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0402] L in Formula 401 402 It can be any suitable monovalent organic ligand, divalent organic ligand or trivalent organic ligand. 402 The moiety may be selected from halogen, diketone (eg, acetylacetone), carboxylic acid (eg, picolinic acid), -C(=O), isonitrile, -CN, and phosphorus-containing groups (eg, phosphine and phosphite), but the embodiments of the present disclosure are not limited thereto.

[0403] In some embodiments, the phosphorescent dopant may include, for example, at least one selected from Compound PD1 to Compound PD25, but the embodiments of the present disclosure are not limited thereto:

[0404]

[0405] Fluorescent dopants in the emitting layer

[0406] The fluorescent dopant may include an aromatic amine compound or a styrylamine compound.

[0407] In some embodiments, the fluorescent dopant may include a compound represented by Formula 501:

[0408] Formula 501

[0409]

[0410] In formula 501,

[0411] Ar 501 Can be selected from substituted or unsubstituted C 5 -C 60 Carbocyclic group and substituted or unsubstituted C 1 -C 60Heterocyclic group,

[0412] L 501 To L 503 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0413] xd1 to xd3 may each independently be an integer from 0 to 3,

[0414] R 501 and R 502 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

[0415] xd4 can be an integer from 1 to 6.

[0416] In some embodiments, in Formula 501, Ar 501 Can be selected from:

[0417] naphthyl, heptathenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and

[0418] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 at least one selected from the group consisting of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, naphthyl, heptalenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The following examples include 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 67, 68,

[0419] In one or more embodiments, in Formula 501, L 501 To L 503 Can be independently selected from:

[0420] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, ...

[0421] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, a phenylene group, a naphthylene group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracene group, an anthracene group, an fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a fluoranthrenyl group, a benzo[9,10]phenanthrenyl group, a py ... The compounds include phenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, and pyridylene.

[0422] In some embodiments, in Formula 501, R 501 and R 502 Can be independently selected from:

[0423] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and

[0424] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl and -Si(Q 31 )(Q 32 )(Q 33 ) is at least one selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, ...

[0425] Among them, Q 31 To Q 33 Can be selected from C 1 -C 10 Alkyl, C1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0426] In one or more embodiments, xd4 in equation 501 may be 2, but embodiments of the present disclosure are not limited thereto.

[0427] In some embodiments, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:

[0428]

[0429]

[0430]

[0431] In some embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments of the present disclosure are not limited thereto:

[0432]

[0433] Electron transport region in organic layer 150

[0434] The electron transport region may have: i) a single layer structure including a single layer including a single material, ii) a single layer structure including a single layer including a plurality of different materials, or iii) a multilayer structure having a plurality of layers each including a plurality of different materials.

[0435] 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 the embodiments of the present disclosure are not limited thereto.

[0436] In some embodiments, 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 the layers of each structure are sequentially stacked on the emission layer in the order stated respectively, but the embodiments of the present disclosure are not limited thereto.

[0437] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, and / 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.

[0438] As used herein, the term "π-electron-poor nitrogen-containing ring" refers to a C-type ring having at least one *-N=*' moiety as a ring-forming part.1 -C 60 Heterocyclic group.

[0439] For example, the "π-electron-poor nitrogen-containing ring" may be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which at least two 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' moiety are condensed, or iii) at least one 5- to 7-membered heteromonocyclic group each having at least one *-N=*' moiety is condensed with at least one C 5 -C 60 A carbocyclic condensed heteropolycyclic group.

[0440] Non-limiting examples of π-electron-poor nitrogen-containing rings include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine and azacarbazole, but embodiments of the present disclosure are not limited thereto.

[0441] In some embodiments, the electron transport region may include a compound represented by Formula 601:

[0442] Formula 601

[0443] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0444] In formula 601,

[0445] Ar 601 Can be selected from substituted or unsubstituted C 5 -C 60 Carbocyclic group and substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0446] xe11 can be 1, 2 or 3,

[0447] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0448] xe1 can be an integer from 0 to 5,

[0449] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),

[0450] Among them, Q 601 To Q 603 can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and

[0451] xe21 can be an integer from 1 to 5.

[0452] In some embodiments, the xe11 Ar in Formula 601 601 and xe21 R601 At least one of the may include a π-electron-poor nitrogen-containing ring.

[0453] In some embodiments, in Formula 601, Ar 601 Can be selected from:

[0454] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthrenyl, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazinyl, phenanthryl ...

[0455] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthracene, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazine, phenanthryl ...

[0456] Among them, Q 31To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0457] When xe11 in Formula 601 is 2 or greater, at least two Ar 601 Can connect via one-touch.

[0458] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.

[0459] In one or more embodiments, the compound represented by Formula 601 can be further represented by Formula 601-1:

[0460] Formula 601-1

[0461]

[0462] In formula 601-1,

[0463] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and from X 614 To X 616 At least one of the selected ones may be N,

[0464] L 611 To L 613 can be independently 601 same,

[0465] xe611 to xe613 can all be independently identical to xe1,

[0466] R 611 To R 613 can be independently related to R 601 The same, and

[0467] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0468] In some embodiments, in equation 601 and equation 601-1, L 601 and L 611 To L 613 Can be independently selected from:

[0469] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and

[0470] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazine at least one selected from the group consisting of phenylene, naphthylene, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthrylenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazin ... The invention also includes pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, but the embodiments of the present disclosure are not limited thereto.

[0471] In one or more embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 may each independently be 0, 1, or 2.

[0472] In some embodiments, in equation 601 and equation 601-1, R 601 and R 611 To R 613 Can be independently selected from:

[0473] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0474] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalide a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0475] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),

[0476] Among them, Q 601 and Q 602 may all independently be the same as described herein.

[0477] The electron transport region may include at least one compound selected from compound ET1 to compound ET36, but the embodiments of the present disclosure are not limited thereto:

[0478]

[0479]

[0480]

[0481]

[0482] In some embodiments, the electron transport region may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 At least one compound selected from the group consisting of 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, and diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1):

[0483]

[0484] The thickness of the buffer layer, the hole blocking layer and / or the electron control layer may each independently be about to about and in some embodiments about to about When the thickness of the buffer layer, the hole blocking layer, and / or the electron control layer is within these ranges, excellent hole blocking characteristics and / or excellent electron control characteristics may be obtained without significantly increasing driving voltage.

[0485] The thickness of the electron transport layer can be about to about In some embodiments, about to about When the thickness of the electron transport layer is within these ranges, excellent electron transport characteristics may be obtained without significantly increasing driving voltage.

[0486] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a material including a metal in addition to the materials described above.

[0487] The material containing the metal 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 lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions, and cesium (Cs) ions. The alkaline earth metal complex may include a metal ion selected from beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions, and barium (Ba) ions. Each ligand coordinated with the metal ion of the alkali metal complex and / or coordinated with the metal ion of the alkaline earth metal complex may be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0488] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) and / or compound ET-D2:

[0489]

[0490] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0491] The electron injection layer may have: i) a single layer structure including a single layer including a single material, ii) a single layer structure including a single layer including a plurality of different materials, or iii) a multilayer structure having a plurality of layers each including a plurality of different materials.

[0492] 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 a combination thereof.

[0493] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In some embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.

[0494] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0495] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

[0496] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may each independently be selected from oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of alkali metals, oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of alkaline earth metals, and oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of rare earth metals.

[0497] The alkali metal compound may be selected from alkali metal oxides (such as Li 2 O, Cs 2 O, and / or K 2 O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and / or RbI). In some embodiments, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0498] The alkaline earth metal compound may be selected from alkaline earth metal oxides (such as BaO, SrO, CaO, Ba x Sr 1-x O (where 0 < x < 1) and / or Ba x Ca 1-x O (where 0 < x < 1)). In some embodiments, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0499] The rare earth metal compound may be selected from YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2O 3 , GdF 3 and TbF 3 In some embodiments, the rare earth metal compound may be selected from YbF 3 ScF 3 , TbF 3 ,YbI 3 ScI 3 and TbI 3 , but the embodiments of the present disclosure are not limited thereto.

[0500] Alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes can include ions of alkali metal, alkaline earth metal and rare earth metal described above, respectively. Each ligand coordinated with the metal ion of alkali metal complexes, alkaline earth metal complexes and / or rare earth metal complexes can be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

[0501] The electron injection layer may include an alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or a combination thereof as described above (e.g., may be composed of an alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or a combination thereof as described above). In some embodiments, the electron injection layer may also include an organic material. When the electron injection layer also includes an organic material, an alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or a combination thereof may be uniformly or non-uniformly dispersed in a matrix including an organic material.

[0502] The thickness of the electron injection layer can be about to about And in some embodiments, about to about When the thickness of the electron injection layer is within these ranges, excellent electron injection characteristics may be obtained without significantly increasing driving voltage.

[0503] The second electrode 190

[0504] The second electrode 190 may be located on the organic layer 150. In some embodiments, the second electrode 190 may be a cathode as an electron injection electrode. In this embodiment, the material used to form the second electrode 190 may be a material having a low work function (such as a metal, an alloy, a conductive compound, and / or a combination thereof).

[0505] The second electrode 190 may 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 the embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0506] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0507] Figures 2 to 4 Description

[0508] Reference Figure 2 , the organic light emitting device 20 includes a first cladding layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, wherein the layers are sequentially stacked in the order stated. Figure 3 , the organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cladding layer 220, wherein the layers are sequentially stacked in the order stated. Figure 4 , the organic light emitting device 40 includes a first cladding layer 210 , a first electrode 110 , an organic layer 150 , a second electrode 190 , and a second cladding layer 220 , wherein the layers are sequentially stacked in the stated order.

[0509] Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 shown in FIG. Figure 1 The first electrode 110, the organic layer 150, and the second electrode 190 shown in FIG. 1 are substantially the same.

[0510] In the organic light-emitting devices 20 and 40, light emitted from the emission layer in the organic layer 150 may pass through the first electrode 110 (which may be a semi-transmissive electrode or a transmissive electrode) and the first cladding layer 210 toward the outside. In the organic light-emitting devices 30 and 40, light emitted from the emission layer in the organic layer 150 may pass through the second electrode 190 (which may be a semi-transmissive electrode or a transmissive electrode) and the second cladding layer 220 toward the outside.

[0511] The first cladding layer 210 and the second cladding layer 220 may improve external light emitting efficiency based on the principle of constructive interference.

[0512] The first capping layer 210 and the second capping layer 220 may 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.

[0513] At least one of the first coating 210 and the second coating 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds 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 some embodiments, at least one of the first coating 210 and the second coating 220 may each independently include an amine compound.

[0514] In one or more embodiments, at least one of the first cladding layer 210 and the second cladding layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

[0515] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but the embodiments of the present disclosure are not limited thereto:

[0516]

[0517] In the above, reference has been made to Figures 1 to 4 An organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.

[0518] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be each formed in a set or predetermined region using one or more suitable methods available in the art (such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging).

[0519] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are each independently formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 To about 10 -3 Torr vacuum and about 0.01 angstroms per second to about The vacuum deposition was performed at a deposition rate of 2000 Å / s.

[0520] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are each independently formed by spin coating, the spin coating may be performed at a coating rate of about 2000 revolutions per minute (rpm) to about 5000 rpm and at a heat treatment temperature of about 80°C to about 200°C, depending on the material to be included in each layer and the structure of each layer to be formed.

[0521] General Definition of Substituents

[0522] As used herein, the term "first row transition metal" refers to any metal element belonging to the first row of the d-block and period 4 of the periodic table. Examples of "first row transition metals" include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn).

[0523] As used herein, the term "second row transition metal" refers to any metal element belonging to the second row of the 5th period and d-block of the periodic table. Examples of "second row transition metals" include yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and cadmium (Cd).

[0524] As used herein, the term "third row transition metal" refers to any metal element belonging to the 6th period of the periodic table and the third row of the d-block / the first row of the f-block. Examples of "third row transition metals" include lanthanum (La), samarium (Sm), europium (Eu), terbium (Tb), thulium (Tm), ytterbium (Yb), lutetium (Lu), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and mercury (Hg).

[0525] As used herein, the term "C 1 -C 60 "Alkyl" refers to a straight or branched aliphatic saturated hydrocarbon monovalent group containing 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of "alkyl" include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 The structure of the alkyl group is basically the same as the divalent group of the structure.

[0526] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60A hydrocarbon group including at least one carbon-carbon double bond in the middle or at the end of the alkyl group. 2 -C 60 Non-limiting examples of "alkenyl" include ethenyl, propenyl, and butenyl. As used herein, the term "C 2 -C 60 "Alkenylene" refers to a 2 -C 60 The structure of the alkenyl group is a divalent group of substantially the same structure.

[0527] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 A hydrocarbon group including at least one carbon-carbon triple bond in the middle or at the end of the alkyl group. 2 -C 60 Non-limiting examples of "alkynyl" include ethynyl and propynyl. As used herein, the term "C 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 The structure of the alkynyl group is a divalent group of substantially the same structure.

[0528] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101 C 1 -C 60 A monovalent group represented by an alkyl group. 1 -C 60 Non-limiting examples of "alkoxy" include methoxy, ethoxy and isopropoxy.

[0529] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group containing 3 to 10 carbon atoms. 3 -C 10 Non-limiting examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C 3 -C 10 "Cycloalkylene" refers to a cycloalkylene group having a 3 -C 10 The structure of the cycloalkyl group is substantially the same as that of a divalent group.

[0530] As used herein, the term "C 1 -C 10The term "heterocycloalkyl" refers to a monovalent saturated monocyclic group including at least one heteroatom selected from N, O, Si, P and S as ring atoms and 1 to 10 carbon atoms. 1 -C 10 Non-limiting examples of "heterocycloalkyl" include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 The structure of the heterocycloalkyl group is substantially the same as that of a divalent group.

[0531] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group which includes 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and is not aromatic. 3 -C 10 Non-limiting examples of "cycloalkenyl" include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 The structure of the cycloalkenyl group is a divalent group of substantially the same structure.

[0532] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P and S as ring atoms, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 The structure of the heterocycloalkenyl group is a divalent group of substantially the same structure.

[0533] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. As used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each independently include two or more rings, the respective rings may be fused (eg, combined).

[0534] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system including 1 to 60 carbon atoms and at least one heteroatom selected from N, O, Si, P and S as a ring atom. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system including 1 to 60 carbon atoms and at least one heteroatom selected from N, O, Si, P and S as a ring atom. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each independently include two or more rings, the respective rings may be fused.

[0535] As used herein, the term "C 6 -C 60 Aryloxy" is represented by -OA 102 (Among them, A 102 C 6 -C 60 As used herein, the term "C 6 -C 60 Arylthio" is represented by -SA 103 (Among them, A 103 C 6 -C 60 A monovalent group represented by an aryl group.

[0536] As used herein, the term "C 1 -C 60 "Heteroaryloxy" refers to a 104 (Among them, A 104 C 1 -C 60 As used herein, the term "C 1 -C 60 "Heteroarylthio" refers to -SA105 (Among them, A 105 C 1 -C 60 A monovalent group represented by a heteroaryl group.

[0537] The term "monovalent non-aromatic condensed polycyclic group" as used herein refers to a monovalent group having two or more condensed rings and including only carbon atoms (e.g., 8 to 60 carbon atoms) as ring-forming atoms, wherein the entire molecular structure is non-aromatic. Non-limiting examples of monovalent non-aromatic condensed polycyclic groups include fluorenyl. The term "divalent non-aromatic condensed polycyclic group" as used herein refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic condensed polycyclic group.

[0538] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein refers to a monovalent group having two or more condensed rings and including at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), wherein the entire molecular structure is non-aromatic. A non-limiting example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic condensed heteropolycyclic group.

[0539] As used herein, the term "C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having only 5 to 60 carbon atoms as ring atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 A "carbocyclic group" may refer to a ring (e.g., benzene), a monovalent group (e.g., phenyl), or a divalent group (e.g., phenylene). In addition, depending on the group attached to C 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.

[0540] As used herein, the term "C 1 -C 60 The term "heterocyclic group" refers to a group having the same carbon atoms as C except that at least one hetero atom selected from N, O, Si, P and S other than carbon atoms (for example, 1 to 60 carbon atoms) is used as a ring-forming atom. 5 -C 60 The structure of the carbocyclic group is substantially the same as that of the group.

[0541] In this specification, substituted C 5 -C60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 5 Alkylene, substituted C 2 -C 5 Alkenylene, substituted C 6 -C 10 Arylene, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

[0542] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0543] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0544] C 3 -C 10Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;

[0545] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22)、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0546] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0547] Among them, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C substituted with at least one selected from deuterium, -F and cyano 1 -C 60 alkyl, C substituted with at least one selected from deuterium, -F and cyano 6 -C 60 Aryl, biphenyl and terphenyl.

[0548] As used herein, the term "Ph" refers to a phenyl group. As used herein, the term "Me" refers to a methyl group. As used herein, the term "Et" refers to an ethyl group. As used herein, the term "ter-Bu" or "Bu t " refers to tert-butyl. The term "OMe" as used herein refers to methoxy.

[0549] As used herein, the term "biphenyl" refers to a phenyl group substituted with a phenyl group. For example, a "biphenyl" group may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0550] As used herein, the term "terphenyl" refers to a phenyl group substituted with a biphenyl group. For example, a "terphenyl" may be a phenyl group substituted with a C 6 -C 60 Aryl C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0551] Unless otherwise defined, the symbols * and *' as used herein refer to the bonding site to the adjacent atoms in the corresponding formula.

[0552] Hereinafter, compounds and organic light-emitting devices according to embodiments of the present disclosure will be described in more detail with reference to Synthesis Examples and Examples. The expression "using B instead of A" used in describing Synthesis Examples means using the same molar equivalent of B instead of the same molar equivalent of A.

[0553] Example

[0554] Synthesis Example 1: Synthesis of Compound 1

[0555]

[0556] 1) Synthesis of intermediate 1-A

[0557] 11.8 grams (g) (50 millimoles (mmol)) of 1,4-dibromobenzene, 3.4 g (50 mmol) of pyrazole, 23 g (100 mmol) of tripotassium phosphate, 1.83 g (10 mmol) of cuprous iodide and 1.17 g (10 mmol) of picolinic acid were added to a reaction vessel. The mixture was suspended in 100 milliliters (mL) of dimethyl sulfoxide. The mixture was stirred at 160° C. for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 300 mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 8.9 g (40 mmol) of intermediate product 1-A.

[0558] 2) Synthesis of intermediate 1-B

[0559] 8.9g (40mmol) intermediate product 1-A is suspended in 100mL tetrahydrofuran. Then, the suspension is cooled to a temperature of -78°C. 19mL of n-BuLi (2.5M in normal hexane) solution is slowly dripped therein, and then stirred at the same temperature for 1 hour. Next, 5.0g (48mmol) trimethyl borate is slowly dripped therein, and the temperature of the mixture is raised to room temperature. Then, the mixture is stirred for another 12 hours. Once the reaction is complete, the acidity of the reaction solution is adjusted to pH 5 with 2N HCl solution, then stirred for 30 minutes, and the organic layer is extracted with ethyl acetate. The organic layer extracted is washed with saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate. 6.4g (34mmol) intermediate product 1-B having removed solvent therefrom is obtained. Intermediate product 1-B is used for the following reaction without further purification.

[0560] 3) Synthesis of intermediate 1-C

[0561] 6.4g (34mmol) of intermediate product 1-B, 5.5g (17mmol) of 2,2'-dibromodiphenylamine, 4.7g (34mmol) of potassium carbonate and 390mg (0.34mmol) of tetrakis (phenylphosphine) palladium were added to the reaction vessel. The mixture was suspended in a mixed solution of 25mL of tetrahydrofuran and 25mL of water. The mixture was stirred at 120°C for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 100mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 5.0g (11mmol) of intermediate product 1-C.

[0562] 4) Synthesis of intermediate 1-D

[0563] 5.0g (11mmol) of intermediate product 1-C is suspended in toluene. The suspension is cooled to a temperature of -78°C. 4.4mL of n-BuLi (2.5M in n-hexane) solution is slowly added dropwise thereto, and then stirred at 0°C for 1 hour. Next, 11.0mL of boron trichloride (1.0M in n-hexane) solution is slowly added dropwise thereto, and then stirred at room temperature for 8 hours. Subsequently, the solvent is removed therefrom, and a suspension of 5.9g (44mmol) of aluminum chloride, 3.1g (22mmol) of 2,2,6,6-tetramethylpiperidine and 70mL of o-dichlorobenzene is added dropwise thereto. Then, the mixture is stirred at a temperature of 160°C for 12 hours, and 4.9g (44mmol) of 1,4-diazabicyclo [2.2.2] octane is added dropwise thereto. A filter is used to remove solid precipitates therefrom. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 2.6 g (5.5 mmol) of Intermediate Product 1-D.

[0564] 5) Synthesis of Compound 1

[0565] 2.6g (5.5mmol) of intermediate product 1-D, 2.3g (5.5mmol) of potassium tetrachloroplatinate and 180mg (0.6mmol) of ammonium tetrabromide were suspended in 110mL of acetic acid and then stirred at a temperature of 120°C for 72 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 100mL of distilled water was added thereto, and the solid compound was filtered. The filtered solid compound was separated by column chromatography to obtain 1.1g (1.7mmol) of compound 1.

[0566] Synthesis Example 2: Synthesis of Compound 6

[0567]

[0568] Compound 6 was synthesized in substantially the same manner as in Synthesis Example 1, except that 3,5-dimethylpyrazole was used instead of pyrazole.

[0569] Synthesis Example 3: Synthesis of Compound 11

[0570]

[0571] 1) Synthesis of intermediate 11-C

[0572] 11.8g (50mmol) of 1,4-dibromobenzene, 6.1g (50mmol) of 2-pyridine boronic acid, 13.8g (100mmol) of potassium carbonate and 1.1g (1.0mmol) of tetrakis (phenylphosphine) palladium were added to the reaction vessel. The mixture was suspended in a mixed solution of 100mL of tetrahydrofuran and 100mL of water. The mixture was stirred at 120°C for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 300mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 9.8g (42mmol) of intermediate product 11-C.

[0573] 2) Synthesis of intermediate product 11-D

[0574] 9.8g (42mmol) of intermediate product 11-C is suspended in 100mL of tetrahydrofuran. Then, the suspension is cooled to a temperature of -78°C. 20mL of n-BuLi (2.5M in normal hexane) solution is slowly added dropwise thereto, and then stirred at the same temperature for 1 hour. Next, 5.2g (50mmol) of trimethyl borate is slowly added dropwise thereto, and the temperature of the mixture is raised to room temperature. Then, the mixture is stirred for another 12 hours. Once the reaction is complete, the acidity of the reaction solution is adjusted to pH 5 with 2N HCl solution, and then stirred for 30 minutes. Once the reaction is complete, the organic layer is extracted with ethyl acetate. The organic layer extracted is washed with saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. 6.8g (34mmol) of the intermediate product 11-D from which the solvent is removed are obtained. Intermediate product 11-D is used for the following reaction without further purification.

[0575] 3) Synthesis of intermediate 11-E

[0576] 6.4g (34mmol) of intermediate product 1-B, 11.0g (34mmol) of 2,2'-dibromodiphenylamine, 9.4g (68mmol) of potassium carbonate and 780mg (0.68mmol) of tetrakis (phenylphosphine) palladium were added to the reaction vessel. The mixture was suspended in a mixed solution of 50mL of tetrahydrofuran and 50mL of water. The mixture was stirred at 20°C for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 100mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 6.6g (17mmol) of intermediate product 11-E.

[0577] 4) Synthesis of intermediate product 11-F

[0578] 6.6g (17mmol) of intermediate product 11-E, 4.1g (20.4mmol) of intermediate product 11-D, 4.7g (34mmol) of potassium carbonate and 390mg (0.34mmol) of tetrakis (phenylphosphine) palladium are added to the reaction vessel. The mixture is suspended in a mixed solution of 25mL of tetrahydrofuran and 25mL of water. The mixture is stirred at 120 ℃ for 24 hours. Once the reaction is complete, the mixture is cooled to room temperature. Then, 100mL of distilled water is added thereto, and the organic layer is extracted with ethyl acetate. The organic layer extracted is washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography, thus obtaining 5.5g (11.9mmol) of intermediate product 11-F.

[0579] 5) Synthesis of intermediate 11-G

[0580] 5.5g (11.9mmol) of intermediate product 11-F was suspended in toluene. The suspension was cooled to a temperature of -78°C. 4.8mL of n-BuLi (2.5M in n-hexane) solution was slowly added dropwise thereto, and then stirred at 0°C for 1 hour. Next, 12.0mL of boron trichloride (1.0M in n-hexane) solution was slowly added dropwise thereto, and then stirred at room temperature for 8 hours. Subsequently, the solvent was removed therefrom under vacuum, and a suspension of 6.4g (48mmol) of aluminum chloride, 3.4g (24mmol) of 2,2,6,6-tetramethylpiperidine and 80mL of o-dichlorobenzene was added dropwise thereto. Then, the mixture was stirred at a temperature of 160°C for 12 hours, and 5.3g (48mmol) of 1,4-diazabicyclo [2.2.2] octane was added dropwise thereto. A filter was used to remove solid precipitates therefrom. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 2.4 g (5.1 mmol) of an intermediate product 11-G.

[0581] 6) Synthesis of Compound 11

[0582] 2.4 g (5.1 mmol) of intermediate product 11-G, 2.1 g (5.1 mmol) of potassium tetrachloroplatinate and 160 mg (0.5 mmol) of ammonium tetrabromide were suspended in 100 mL of acetic acid and then stirred at a temperature of 120 ° C for 72 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 100 mL of distilled water was added thereto, and the solid compound was filtered. The filtered solid compound was separated by column chromatography to obtain 850 mg (1.3 mmol) of compound 11.

[0583] Synthesis Example 4: Synthesis of Compound 16

[0584]

[0585] 780 mg (1.1 mmol) of Compound 16 was obtained in substantially the same manner as in Synthesis Example 3, except that Intermediate 6-B was used instead of Intermediate 1-B and 4-methylpyridine-2-boronic acid was used instead of 2-pyridineboronic acid.

[0586] Synthesis Example 5: Synthesis of Compound 21

[0587]

[0588] 1) Synthesis of intermediate 21-C

[0589] 11.8 g (50 mmol) of 1,4-dibromobenzene, 5.9 g (50 mmol) of benzimidazole, 23 g (100 mmol) of tripotassium phosphate, 1.83 g (10 mmol) of cuprous iodide and 1.17 g (10 mmol) of picolinic acid were added to a reaction vessel. The mixture was suspended in 100 mL of dimethyl sulfoxide. The mixture was stirred at 160° C. for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 300 mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 9.6 g (35 mmol) of intermediate product 21-C.

[0590] 2) Synthesis of intermediate product 21-D

[0591] 9.6g (35mmol) of intermediate product 21-C is suspended in 100mL of tetrahydrofuran. Then, the suspension is cooled to a temperature of -78°C. 19mL of n-BuLi (2.5M in normal hexane) solution is slowly added dropwise thereto, and then stirred at the same temperature for 1 hour. Next, 4.3g (42mmol) of trimethyl borate is slowly added dropwise thereto, and the temperature of the mixture is raised to room temperature. Then, the mixture is stirred for another 12 hours. Once the reaction is complete, the acidity of the reaction solution is adjusted to pH 5 with 2N HCl solution, and then stirred for 30 minutes. Once the reaction is complete, the organic layer is extracted with ethyl acetate. The extracted organic layer is washed with saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Remove the solvent, and obtain 7.2g (30mmol) of intermediate product 21-D. Intermediate product 21-D is used for the following reaction without any further purification.

[0592] 3) Synthesis of intermediate product 21-F

[0593] 6.6g (17mmol) of intermediate product 11-E, 4.9g (20.4mmol) of intermediate product 21-D, 4.7g (34mmol) of potassium carbonate and 390mg (0.34mmol) of tetrakis (phenylphosphine) palladium are added to the reaction vessel. The mixture is suspended in a mixed solution of 25mL of tetrahydrofuran and 25mL of water. The mixture is stirred at 120 ℃ for 24 hours. Once the reaction is complete, the mixture is cooled to room temperature. Then, 100mL of distilled water is added thereto, and the organic layer is extracted with ethyl acetate. The organic layer extracted is washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography, thus obtaining 5.6g (11.1mmol) of intermediate product 21-F.

[0594] 4) Synthesis of intermediate product 21-G

[0595] 5.6g (11.1mmol) of intermediate product 21-F was suspended in toluene. The suspension was cooled to a temperature of -78°C. 5mL of n-BuLi (2.5M in n-hexane) solution was slowly added dropwise thereto, and then stirred at 0°C for 1 hour. Next, 11.2mL of boron trichloride (1.0M in n-hexane) solution was slowly added dropwise thereto, and then stirred at room temperature for 8 hours. Subsequently, the solvent was removed therefrom under vacuum, and a suspension of 6.0g (45mmol) of aluminum chloride, 3.2g (22mmol) of 2,2,6,6-tetramethylpiperidine and 75mL of o-dichlorobenzene was added dropwise thereto. Then, the mixture was stirred at a temperature of 160°C for 12 hours, and 4.9g (45mmol) of 1,4-diazabicyclo [2.2.2] octane was added dropwise thereto. A filter was used to remove solid precipitates therefrom. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 2.6 g (5.0 mmol) of Intermediate Product 21-G.

[0596] 5) Synthesis of intermediate product 21-H

[0597] 5.6 g (11.1 mmol) of intermediate product 21-G and 3.2 g (22.2 mmol) of methyl iodide were suspended in 110 mL of toluene and then stirred at a temperature of 110 ° C for 12 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, the solid compound was filtered and washed with ether. The resulting product was then dried to obtain 6.9 g (10.5 mmol) of intermediate product 21-H.

[0598] 6) Synthesis of intermediate product 21-I

[0599] 6.9g (10.5mmol) of intermediate product 21-H is suspended in a mixed solution of 55mL methanol and 55mL water. Subsequently, 2.6g (15.8mmol) of ammonium hexafluorophosphate is added dropwise thereto, and then stirred at room temperature for 12 hours. Once the reaction is complete, the solid compound is filtered and washed with ether. Then the resulting product is dried to obtain 6.3g (9.5mmol) of intermediate product 21-I.

[0600] 7) Synthesis of Compound 21

[0601] 6.3g (9.5mmol) of intermediate product 21-I, 3.9g (10.5mmol) of dichloro (1,5-cyclooctadiene) platinum and 1.6g (19.0mmol) of sodium acetate were suspended in 100mL of dioxane. The mixture was stirred at 110°C for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 200mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 2.2g (3.1mmol) of compound 21.

[0602] Synthesis Example 6: Synthesis of Compound 26

[0603]

[0604] 1.9 g (2.5 mmol) of Compound 26 was obtained in substantially the same manner as in Synthesis Example 5, except that Intermediate Product 16-E was used instead of Intermediate Product 11-E.

[0605] Synthesis Example 7: Synthesis of Compound 31

[0606]

[0607] 1) Synthesis of intermediate 31-C

[0608] 11.8 g (50 mmol) of 1,4-dibromobenzene, 3.5 g (50 mmol) of 1H-1,2,3-triazole, 23 g (100 mmol) of tripotassium phosphate, 1.83 g (10 mmol) of cuprous iodide and 1.17 g (10 mmol) of picolinic acid were added to a reaction vessel. The mixture was suspended in 100 mL of dimethyl sulfoxide. The mixture was stirred at 160° C. for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 300 mL of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 8.7 g (39 mmol) of intermediate product 31-C.

[0609] 2) Synthesis of intermediate product 31-D

[0610] 8.7g (39mmol) intermediate product 31-C is suspended in 100mL tetrahydrofuran. Then, the suspension is cooled to a temperature of -78°C. 19mL of n-BuLi (2.5M in normal hexane) solution is slowly added dropwise thereto, and then stirred at the same temperature for 1 hour. Next, 4.8g (48mmol) trimethyl borate is slowly added dropwise thereto, and the temperature of the mixture is raised to room temperature. Then, the mixture is stirred for another 12 hours. Once the reaction is complete, the acidity of the reaction solution is adjusted to pH 5 with 2N HCl solution, and then stirred for 30 minutes. Once the reaction is complete, the organic layer is extracted with ethyl acetate. The extracted organic layer is washed with saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Remove the solvent to obtain 6.2g (33mmol) intermediate product 31-D. Intermediate product 31-D is used for the following reaction without further purification.

[0611] 3) Synthesis of intermediate product 31-F

[0612] 6.6g (17mmol) of intermediate product 11-E, 3.9g (20.4mmol) of intermediate product 31-D, 4.7g (34mmol) of potassium carbonate and 390mg (0.34mmol) of tetrakis (phenylphosphine) palladium are added to the reaction vessel. The mixture is suspended in a mixed solution of 25mL of tetrahydrofuran and 25mL of water. The mixture is stirred at 120 ℃ for 24 hours. Once the reaction is complete, the mixture is cooled to room temperature. Then, 100mL of distilled water is added thereto, and the organic layer is extracted with ethyl acetate. The organic layer extracted is washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography, thus obtaining 5.3g (11.6mmol) of intermediate product 31-F.

[0613] 4) Synthesis of intermediate product 31-G

[0614] 5.3g (11.6mmol) of intermediate product 31-F was suspended in toluene. The suspension was cooled to a temperature of -78°C. 4.7mL of n-BuLi (2.5M in n-hexane) solution was slowly added dropwise thereto, and then stirred at 0°C for 1 hour. Next, 11.7mL of boron trichloride (1.0M in n-hexane) solution was slowly added dropwise thereto, and then stirred at room temperature for 8 hours. Subsequently, the solvent was removed therefrom under vacuum, and a suspension of 6.3g (48mmol) of aluminum chloride, 3.5g (24mmol) of 2,2,6,6-tetramethylpiperidine and 80mL of o-dichlorobenzene was added dropwise thereto. Then, the mixture was stirred at a temperature of 160°C for 12 hours, and 5.3g (48mmol) of 1,4-diazabicyclo [2.2.2] octane was added dropwise thereto. A filter was used to remove solid precipitates therefrom. The residue from which the solvent was removed was separated by column chromatography, thereby obtaining 2.1 g (4.6 mmol) of Intermediate Product 31-G.

[0615] 5) Synthesis of compound 31

[0616] 2.1 g (4.6 mmol) of intermediate product 31-G, 1.9 g (4.6 mmol) of potassium tetrachloroplatinate and 160 mg (0.5 mmol) of ammonium tetrabromide were suspended in 100 mL of acetic acid and then stirred at 120 ° C for 72 hours. Once the reaction was complete, the mixture was cooled to room temperature. Then, 100 mL of distilled water was added thereto, and the solid compound was filtered. The filtered solid compound was separated by column chromatography to obtain 740 mg (1.1 mmol) of compound 31.

[0617] Synthesis Example 8: Synthesis of Compound 36

[0618]

[0619] 1.0 g (1.6 mmol) of Compound 36 was obtained in substantially the same manner as in Synthesis Example 7, except that 2H-1,2,3-triazole was used instead of 1H-1,2,3-triazole.

[0620] pass 1 H nuclear magnetic resonance (NMR) and mass spectrometry / fast atom bombardment (MS / FAB) were used to identify the compounds synthesized in Synthesis Examples 1 to 8. The results are shown in Table 1.

[0621] Those skilled in the art can easily understand methods of synthesizing compounds other than the compounds shown in Table 1 by referring to the above-mentioned synthetic routes and raw materials.

[0622] Table 1

[0623]

[0624] Example 1

[0625] As the anode, an ITO glass substrate (thickness Available from Corning Incorporated) was cut into a size of 50 millimeters (mm) × 50 mm × 0.7 mm, sonicated in each of isopropyl alcohol and pure water for 5 minutes, cleaned with ultraviolet light for 30 minutes, then cleaned with ozone, and mounted on a vacuum deposition apparatus.

[0626] 2-TNATA was vacuum deposited on an ITO substrate to form NPB is vacuum deposited on the hole injection layer to form a hole injection layer having a thickness of The hole transport layer has a thickness of .

[0627] BCPDS, POPCPA and compound 1 were co-deposited in a ratio of 45:45:10 on the hole transport layer to form a The thickness of the emission layer.

[0628] Subsequently, TSPO1 is vacuum deposited on the emission layer to form a A hole blocking layer with a thickness of 1000 nm was formed. Alq was vacuum deposited on the hole blocking layer. 3 To form a LiF is deposited on the electron transport layer to form an electron transport layer having a thickness of Al is vacuum deposited on the electron injection layer to form an electron injection layer having a thickness of A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.

[0629]

[0630] Examples 2 to 8 and Comparative Examples 1 to 3

[0631] Another organic light emitting device was manufactured in substantially the same manner as in Example 1, except that the compound shown in Table 2 was used instead of Compound 1 in the formation of the emission layer.

[0632] Evaluation example

[0633] The driving voltage, luminance, luminous efficiency, emission color and emission wavelength of the organic light emitting devices manufactured in Examples 1 to 8 and Comparative Examples 1 to 3 were measured using a source measurement unit (Keithley SMU 236) and a luminance meter PR650 at the current density shown in Table 2. The results are shown in Table 2.

[0634] Table 2

[0635]

[0636]

[0637] Referring to the results of Table 2, it was found that the organic light emitting devices manufactured in Examples 1 to 8 had improved driving voltage, improved brightness, and improved light emitting efficiency compared to the organic light emitting devices manufactured in Comparative Examples 1 to 3.

[0638] As apparent from the foregoing description, an organic light emitting device including an organic metal compound may have a low driving voltage, excellent brightness, and high light emitting efficiency.

[0639] As used herein, the term "using" and variations thereof may be considered synonymous with the term "utilizing" and variations thereof, respectively. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure."

[0640] As used herein, the terms "substantially," "approximately," and similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent variations in measurements or calculations that would be recognized by those having ordinary skill in the art.

[0641] In addition, any numerical range stated herein is intended to include all subranges of the same numerical precision contained in the stated range. For example, the range "1.0 to 10.0" is intended to include all subranges between the stated minimum value 1.0 and the stated maximum value 10.0 (and including the stated minimum value 1.0 and the stated maximum value 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 2.4 to 7.6. Any maximum numerical limit stated herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly state any subrange contained in the scope explicitly stated here.

[0642] It should be understood that the 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.

[0643] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the disclosure as defined by the claims and their equivalents.

Claims

1. An organometallic compound, the organometallic compound is represented by Formula 1: Formula 1 <h2 style=";text-align:left;direction:ltr">M1(L1)<h2 style=";text-align:left;direction:ltr"> n1 <h2 style=";text-align:left;direction:ltr"> (L2)<h2 style=";text-align:left;direction:ltr"> n2 <h2 style=";text-align:left;direction:ltr"> , Formula 1-1 in, In Formula 1 and Formula 1-1, M1 is selected from platinum, L1 is a ligand represented by formula 1-1, L2 is selected from monodentate ligands and bidentate ligands, n1 is 1, n2 is selected from 0, A 11 and A 12 are independently selected from indolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, pyrazolyl, imidazolyl, triazolyl, benzopyrazolyl and benzimidazolyl, A 13 To A 16 are independently selected from phenyl, X 11 To X 18 All are C, Y 11 To Y 14 are independently selected from N and C, i) Z 11 is B, and Z 12 is N; or ii) Z 11 is N, and Z 12 For B, T 11 To T 14 All are single bonds, L 11 To L 13 are independently selected from single bonds, a11 and a12 are both selected from 1, and a13 is 0, When a13 is 0, A 11 and A 12 Not connected to each other, R 11 To R 16 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano and C1-C 20 alkyl; C1-C1-C1-substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and cyano 20 Alkyl; and The group represented by formula 5-1: In formula 5-1, R 51 Selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, thienyl, furyl, thiols, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, benzothiols, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiols, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32 ), Q 31 To Q 33 are independently selected from C1-C 60 Alkyl, phenyl, biphenyl and terphenyl, b51 is selected from 1, 2, 3, 4 and 5, b11 to b16 are independently selected from 1, 2, 3, 4, 5, 6, 7 and 8, *1 to *4 independently represent the binding site to M1, and *Indicates the binding site with the adjacent atom.

2. The organometallic compound according to claim 1, wherein L1 is expressed by formula 1-11: Formula 1-11 Among them, in formula 1-11, *1 to *4, A 11 To A 16 , Y 11 To Y 14 , L 11 , L 12 、a11、a12、R 11 To R 16 And b11 to b16 are the same as those in Formula 1-1.

3. The organometallic compound according to claim 1, wherein L1 is expressed by formula 1-12: Formula 1-12 Among them, in formula 1-12, *1 to *4, A 11 To A 16 , Y 11 To Y 14 , L 11 , L 12 、a11、a12、R 11 To R 16 And b11 to b16 are the same as those in Formula 1-1.

4. The organometallic compound according to claim 1, wherein L1 is expressed by one selected from Equation 1-31 and Equation 1-32: Formula 1-31 Formula 1-32 Among them, in Formula 1-31 and Formula 1-32, *1 to *4, A 11 , A 12 , Y 13 , Y 14 , L 11 , L 12 , a11, a12, b11 and b12 are the same as those in Formula 1-1, R 13a , R 13b , R 14a , R 14b , R 15a To R 15d and R 16a To R 16d Both are the same as R in formula 1-1 13 The same, and R 11 and R 12 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano and C1-C 20 alkyl.

5. The organometallic compound according to claim 1, wherein The organometallic compound represented by Formula 1 is selected from Compound 1 to Compound 9, Compound 11 to Compound 45, Compound 121 to Compound 129, and Compound 131 to Compound 165: Here, "Ph" represents a phenyl group.

6. The organometallic compound according to claim 1, wherein The organometallic compound is used to emit blue light having a maximum emission wavelength of 450 nm or more and less than 490 nm.

7. An organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer located between the first electrode and the second electrode and including an emission layer, Wherein, the organic layer comprises the organic metal compound according to claim 1.

8. The organic light emitting device according to claim 7, wherein: The first electrode is an anode, The second electrode is a cathode, The organic layer includes a hole transport region between the first electrode and the emission layer and / or an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

9. The organic light emitting device according to claim 7, wherein: The emission layer includes the organic metal compound.

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