Organometallic Compound, Organic Light-Emitting Device, and Device Including the Same
By using specific organometallic compounds in organic light emitting devices, the problem of insufficient luminescence efficiency and stability in the prior art is solved, and more efficient exciton complex formation and charge transport are achieved, thereby improving the overall performance of electronic devices.
Patent Information
- Application Number
- CN202010111449.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-03-13
- Filing Date
- 2020-02-24
- Publication Date
- 2025-06-24
- Estimated Expiration
- 2040-02-24
AI Technical Summary
Existing organic light emitting devices have challenges in improving luminescence efficiency and stability, especially during the formation of exciton complexes and charge transport.
The organometallic compound M11(L11)n11(L12)n12 represented by Formula 1 is used as the emission layer material, which includes transition metal M11 and a variety of ligands L11 and L12. The performance of the electronic device is optimized by adjusting the selection of metal centers and ligands.
By using these organometallic compounds, the luminous efficiency and stability of the organic light emitting device can be improved, the formation and charge transport characteristics of exciton composites can be improved, and the overall performance of electronic devices can be improved.
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Figure CN111690012B_ABST
Abstract
Description
[0001] This application claims the benefit of Korean Patent Application No. 10-2019-0028854, filed on Mar. 13, 2019, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein by reference in its entirety. Technical Field
[0002] One or more embodiments relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and a device including the organic light-emitting device. Background Art
[0003] An organic light-emitting device is a self-emitting device that generates a full-color image and also has a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0004] In an example, an organic light-emitting device includes a first electrode disposed on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially disposed 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. Charge carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the Invention
[0005] One or more embodiments include an organometallic compound, an organic light-emitting device including the organometallic compound, and a device including the organic light-emitting device.
[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 aspect of the present disclosure provides an organometallic compound represented by Formula 1:
[0008] <Formula 1>
[0009] M 11 (L 11 ) n11 (L 12 ) n12 .
[0010] In Formula 1,
[0011] M 11 may be selected from the first-row transition metals, second-row transition metals, and third-row transition metals of the periodic table,
[0012] L 11 may be a ligand represented by Formula 1-1,
[0013] L 12 may be selected from monodentate ligands and bidentate ligands,
[0014] n11 may be 1, and
[0015] n12 may be selected from 0, 1, and 2:
[0016] <Formula 1-1>
[0017]
[0018] In Formula 1-1,
[0019] X 11 to X 13 may each independently be selected from a single bond, *-O-*', *-S-*', *-C(B 11 )(B 12 )-*', *-Si(B 11 )(B 12 )-*', *-B(B 11 )-*', *-N(B 11 )-*', and *-P(B 11 )-*',
[0020] Y 11 to Y 14 may each independently be N or C,
[0021] T 11 to T 14 may each independently be selected from a single bond, *-O-*', *-S-*', *-C(B 13 )(B 14 )-*', *-Si(B 13 )(B 14 )-*', *-B(B 13 )-*', *-N(B 13 )-*', and *-P(B 13 )-*',
[0022] Ring A 11 to Ring A 20 may each independently be selected from C5-C 60 carbocyclic groups and C1-C 60 heterocyclic groups,
[0023] B 11 to B 14 and R 11 to R 20may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),
[0024] b11 to b20 may each independently be an integer from 1 to 10,
[0025] Q1 to Q3 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, C1-C substituted with at least one selected from deuterium, -F, cyano, C1-C 60 alkyl, phenyl, and biphenyl, C1-C 60 alkyl, substituted with at least one selected from deuterium, -F, cyano, C1-C 10 alkyl, phenyl, and biphenyl, C6-C 60 aryl, and C1-C substituted with at least one selected from deuterium, -F, cyano, C1-C 10 alkyl, phenyl, and biphenyl, C1-C 60 heteroaryl,
[0026] *1 and *4 both represent the binding positions to M 11 and
[0027] * and *' both represent the binding positions to adjacent atoms.
[0028] Another aspect of the present disclosure provides an organic light-emitting device, which includes: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the above-mentioned organometallic compound.
[0029] Another aspect of the present disclosure provides a device, which includes: a thin-film transistor including a source electrode, a drain electrode, and an active layer; and the above-mentioned organic light-emitting device, wherein the first electrode of the organic light-emitting device is electrically connected to one of the source electrode and the drain electrode of the thin-film transistor. Description of the Drawings
[0030] Through the following description of the embodiments in conjunction with the drawings, these and / or other aspects will become apparent and easier to understand. In the drawings:
[0031] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;
[0032] Figure 2 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment;
[0033] Figure 3 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment; and
[0034] Figure 4 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment. Detailed Description of the Embodiments
[0035] Now, the present disclosure will be described more fully with reference to exemplary embodiments. However, the disclosure may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the disclosure to those skilled in the art. The features of the inventive concept and how to implement them will become apparent by referring to the embodiments and the drawings to be described in detail later. However, the present embodiments may be embodied in many different forms and should not be limited to the exemplary embodiments.
[0036] Hereinafter, embodiments will be described in detail with reference to the accompanying drawings, in which like reference numerals denote like elements, and redundant descriptions thereof will not be provided herein.
[0037] As used herein, unless the context clearly indicates otherwise, the singular forms "a", "an", and "the" are also intended to include the plural forms.
[0038] It will also be understood that the terms "comprises" and / or its variants used herein specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.
[0039] It will be understood that when a layer, region, or component is referred to as being "on" or "onto" another layer, region, or component, the layer, region, or component may be directly or indirectly formed on the other layer, region, or component. That is, for example, there may be an intermediate layer, intermediate region, or intermediate component.
[0040] For ease of explanation, the dimensions of elements in the drawings may be exaggerated. In other words, since the dimensions and thicknesses of the components in the drawings are arbitrarily shown for ease of explanation, the following embodiments of the present disclosure are not limited thereto.
[0041] As used herein, the term "organic layer" refers to a single layer and / or multiple layers provided between the first electrode and the second electrode of an organic light-emitting device. The materials included in the "organic layer" are not limited to organic materials.
[0042] The organometallic compound according to an embodiment is represented by the following Formula 1:
[0043] <Formula 1>
[0044] M 11 (L 11 ) n11 (L 12 ) n12 。
[0045] In Formula 1,
[0046] M 11It may be selected from the first-row transition metals, second-row transition metals, and third-row transition metals of the periodic table.
[0047] For example, M in Formula 1 11 may 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.
[0048] In one embodiment, M in Formula 1 11 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.
[0049] In one or more embodiments, M in Formula 1 11 may be selected from Pt, Pd, Cu, Ag, Au, Ru, and Os, but the embodiments of the present disclosure are not limited thereto.
[0050] In one or more embodiments, M in Formula 1 11 may be selected from Pt, Pd, Ru, and Os, but the embodiments of the present disclosure are not limited thereto.
[0051] L in Formula 1 11 may be a ligand represented by Formula 1-1:
[0052] <Formula 1-1>
[0053]
[0054] In Formula 1-1, X 11 to X 13 may each independently be selected from a single bond, *-O-*', *-S-*', *-C(B 11 )(B 12 )-*', *-Si(B 11 )(B 12 )-*', *-B(B 11 )-*', *-N(B 11 )-*', and *-P(B 11 )-*', and B 11 and B 12 can be understood by referring to its detailed description provided later.
[0055] For example, X in Formula 1-1 11 to X 13 may each independently be selected from a single bond, *-O-*', *-S-*', *-C(B 11 )(B12 )-*', and *-N(B 11 )-*', but the embodiments of the present disclosure are not limited thereto.
[0056] In one or more embodiments, at least one selected from X in Formula 1-1 11 to X 13 may be a single bond, but the embodiments of the present disclosure are not limited thereto.
[0057] In one embodiment, in Formula 1-1,
[0058] X 11 may be a single bond, and X 12 and X 13 may each independently be selected from a single bond, *-O-*, *-S-*, *-C(B 11 )(B 12 )-*, and *-N(B 11 )-*; or
[0059] X 12 may be a single bond, and X 11 and X 13 may each independently be selected from a single bond, *-O-*, *-S-*, *-C(B 11 )(B 12 )-*, and *-N(B 11 )-*.
[0060] In one embodiment, X in Formula 1-1 11 to X 13 may be a single bond, but the embodiments of the present disclosure are not limited thereto.
[0061] Y in Formula 1-1 11 to Y 14 may each independently be nitrogen (N) or carbon (C).
[0062] T in Formula 1-1 11 to T 14 may each independently be selected from a single bond, *-O-*, *-S-*, *-C(B 13 )(B 14 )-*, *-Si(B 13 )(B 14 )-*, *-B(B 13 )-*, *-N(B 13 )-*, and *-P(B 13 )-*, and B 13 and B 14 can be understood by referring to its detailed description provided later.
[0063] For example, T in Formula 1-1 11 to T 14 may each independently be selected from a single bond, *-O-*', and *-S-*', but is not limited thereto.
[0064] In one or more embodiments, T in Formula 1-1 11 to T 14 may be a single bond, but the embodiments of the present disclosure are not limited thereto.
[0065] Ring A in Formula 1-1 11 to Ring A 20 may each independently be selected from C5-C 60 carbocyclic groups and C1-C 60 heterocyclic groups.
[0066] For example, Ring A in Formula 1-1 11 to Ring A 20 may each independently be: i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused to each other, iv) a fused ring in which at least two second rings are fused to each other, or v) a fused ring in which at least one first ring and at least one second ring are fused to each other.
[0067] The first ring may be selected from cyclopentyl, cyclopentenyl, cyclopentadienyl, furyl, thienyl, pyrrolyl, borole group, phosphole group, silole group, germole group, selenophenyl, oxazolyl, dihydrooxazolyl, isoxazolyl, dihydroisoxazolyl, oxadiazolyl, dihydrooxadiazolyl, isoxadiazolyl, dihydroisoxadiazolyl, oxatriazolyl, dihydrooxatriazolyl, isoxatriazolyl, dihydroisoxatriazolyl, thiazolyl, dihydrothiazolyl, isothiazolyl, dihydroisothiazolyl, thiadiazolyl, dihydrothiadiazolyl, isothiadiazolyl, dihydroisothiadiazolyl, thiatriazolyl, dihydrothiatriazolyl, isothiatriazolyl, dihydroisothiatriazolyl, pyrazolyl, dihydropyrazolyl, imidazolyl, dihydroimidazolyl, triazolyl, dihydrotriazolyl, tetrazolyl, dihydrotetrazolyl, azasilole group, diazasilole group, and triazasilole group, but the embodiments of the present disclosure are not limited thereto.
[0068] The second ring may be selected from cyclohexyl, cyclohexenyl, cyclohexadienyl, adamantyl, norbornyl, norbornenyl, phenyl, pyridyl, dihydropyridyl, tetrahydropyridyl, pyrimidinyl, dihydropyrimidinyl, tetrahydropyrimidinyl, pyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, pyridazinyl, dihydropyridazinyl, tetrahydropyridazinyl, and triazinyl, but the embodiments of the present disclosure are not limited thereto.
[0069] In one embodiment, Ring A in Formula 1-111 to Ring A 20 may each independently be selected from phenyl, naphthyl, anthryl, phenanthryl, benzo[9,10]phenanthryl, pyrenyl, -yl, furyl, thienyl, silolyl, indenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, indolyl, carbazolyl, indolopyridyl, indolopyridinyl, benzofuranopyridyl, benzothienopyridyl, benzosilolopyridyl, indolopyrimidinyl, indolopyrimidinyl, benzofuranopyrimidinyl, benzothienopyrimidinyl, benzosilolopyrimidinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, dihydroimidazolyl, triazolyl, dihydrotriazolyl, oxazolyl, dihydrooxazolyl, isoxazolyl, thiazolyl, dihydrothiazolyl, isothiazolyl, oxadiazolyl, dihydrooxadiazolyl, thiadiazolyl, dihydrothiadiazolyl, benzopyrazolyl, benzimidazolyl, dihydrobenzimidazolyl, imidazopyridyl, imidazopyrimidinyl, imidazopyrazinyl, benzoxazolyl, dihydrobenzoxazolyl, benzothiazolyl, dihydrobenzothiazolyl, benzoxadiazolyl, dihydrobenzoxadiazolyl, benzothiadiazolyl and dihydrobenzothiadiazolyl, but the embodiments of the present disclosure are not limited thereto.
[0070] In one or more embodiments, in Formula 1-1, Ring A 11 to Ring A 14 may each independently be selected from phenyl, naphthyl, indenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, indolyl, carbazolyl, indolopyridyl, indolopyridinyl, benzofuranopyridyl, benzothienopyridyl, indolopyrimidinyl, indolopyrimidinyl, benzofuranopyrimidinyl, benzothienopyrimidinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, dihydroimidazolyl, triazolyl, dihydrotriazolyl, oxazolyl, dihydrooxazolyl, isoxazolyl, thiazolyl, dihydrothiazolyl, isothiazolyl, oxadiazolyl, dihydrooxadiazolyl, thiadiazolyl, dihydrothiadiazolyl, benzopyrazolyl, benzimidazolyl, dihydrobenzimidazolyl, imidazopyridyl, imidazopyrimidinyl, imidazopyrazinyl, benzoxazolyl, dihydrobenzoxazolyl, benzothiazolyl, dihydrobenzothiazolyl, benzoxadiazolyl, dihydrobenzoxadiazolyl, benzothiadiazolyl and dihydrobenzothiadiazolyl, and
[0071] Ring A 15 to Ring A 20may each independently be selected from phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl, but the embodiments of the present disclosure are not limited thereto.
[0072] In one or more embodiments, ring A in Formula 1-1 11 to ring A 14 may each independently be represented by one of Formulas 2-1 to 2-43, but the embodiments are not limited thereto:
[0073]
[0074] In Formulas 2-1 to 2-43,
[0075] X 21 to X 23 may each independently be selected from C(R 24 ) and C-*, where at least two selected from X 21 to X 23 may be C-*,
[0076] X 24 may be N-*, and X 25 and X 26 may each independently be selected from C(R 24 ) and C-*, where at least one selected from X 25 and X 26 may be C-*,
[0077] X 27 and X 28 may each independently be selected from O, S, C(R 24 ), N, N(R 24 ), and N-*, and X 29 may be selected from O, S, C(R 24 ), and C-*, where i) at least one selected from X 27 and X 28 may be N-*, and X 29 may be C-*, or ii) X 27 and X 28 may each independently be N-*, and X 29 may be selected from O, S, and C(R 24 ),
[0078] R 21 to R 24 may each independently be the same as defined for R in Formula 1-1 11 ,
[0079] b21 may be selected from 1, 2, and 3,
[0080] b22 can be selected from 1, 2, 3, 4, and 5,
[0081] b23 can be selected from 1, 2, 3, and 4,
[0082] b24 can be selected from 1 and 2, and
[0083] * represents a binding site to an adjacent atom.
[0084] In one embodiment, in Formula 1-1, the group represented by can be a group represented by Formula 3-11, the group represented by can be a group represented by Formula 3-21, the group represented by can be a group represented by Formula 3-31, and the group represented by can be a group represented by Formula 3-41, but the embodiments of the present disclosure are not limited thereto:
[0085]
[0086] In Formulas 3-11, 3-21, 3-31, and 3-41,
[0087] *, *', and *" all represent binding sites to adjacent atoms,
[0088] R 11a , R 11b and R 11c can each independently be the same as defined for R 11 in Formula 1-1,
[0089] R 12a , R 12b and R 12c can each independently be the same as defined for R 12 in Formula 1-1,
[0090] R 13a , R 13b and R 13c can each independently be the same as defined for R 13 in Formula 1-1, and
[0091] R 14a , R 14b , R 14c and R 14d can each independently be the same as defined for R 14 in Formula 1-1.
[0092] In one embodiment, in Formula 1-1, the group represented by The represented group may be a group represented by one selected from Formula 10-1 to Formula 10-15, and by The represented group may be a group represented by one selected from Formula 11-1 to Formula 11-15, and by The represented group may be a group represented by one selected from Formula 12-1 to Formula 12-15:
[0093]
[0094]
[0095]
[0096]
[0097] In Formula 10-1 to Formula 10-15, Formula 11-1 to Formula 11-15, and Formula 12-1 to Formula 12-15,
[0098] * and *' both represent bonding positions to adjacent atoms, and
[0099] R 15 to R 20 and b15 to b20 may all independently be the same as defined in Formula 1-1.
[0100] For example, in Formula 10-1 to Formula 10-15, Formula 11-1 to Formula 11-15, and Formula 12-1 to Formula 12-15, R 15 to R 20 may all independently be selected from:
[0101] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and groups represented by Formula 9-1 to Formula 9-16; and
[0102] groups represented by Formula 9-1 to Formula 9-16 that are all substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and cyano, but the embodiments of the present disclosure are not limited thereto:
[0103]
[0104] In Formula 1-1, B 11 to B 14 and R 11 to R 20 may all independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkylaryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2), and
[0105] Q1 to Q3 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, substituted with at least one selected from deuterium, -F, cyano, C1-C 60 Alkyl, phenyl and biphenyl of C1-C 60 Alkyl, substituted with at least one selected from deuterium, -F, cyano, C1-C 10 Alkyl, phenyl and biphenyl of C6-C 60 Aryl and substituted with at least one selected from deuterium, -F, cyano, C1-C 10At least one selected from alkyl, phenyl and biphenyl, C1-C 60 heteroaryl.
[0106] For example, in Formula 1-1, B 11 to B 14 and R 11 to R 20 can each independently be selected from:
[0107] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl and C1-C 20 alkoxy;
[0108] C1-C 20 alkyl and C1-C 20 alkoxy, each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl and terphenyl;
[0109] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, bicyclopentadienyl, indenyl, naphthyl, azulene, indacenyl, acenaphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, anthracenyl, perylenyl, pentacenyl, pyrrolyl, thienyl, furyl, silolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, 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, triazinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthosilolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafuranyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzosilolyl, indolopyrrolyl, indolopyrrolyl, indolocarbazolyl and indolocarbazolyl;
[0110] each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, bicyclopentadienyl, indenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, perylenyl, pentacenyl, pyrrolyl, thienyl, furyl, silolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthosilolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafuranyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzosilolyl, indolopyrrolyl, indolopyrrolyl, indolocarbazolyl, indolocarbazolyl, -C(Q 31 )(Q 32 )(Q 33 ), -Si(Q 31 )(Q 32 )(Q 33 ), -B(Q 31 )(Q 32 ), -N(Q 31 )(Q 32 ), -P(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 32At least one selected from cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, bicyclopentadienyl, indenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, anthracenyl, perylenyl, pentacenyl, pyrrolyl, thienyl, furyl, silolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthosilolyl, imidazopyridyl, imidazopyrimidinyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafuranyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzosilolyl, indolopyrrolyl, indolopyrrolyl, indolocarbazolyl and indolocarbazolyl; and
[0111] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2), and
[0112] Q1 to Q3 and Q 31 to Q 33 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, C1-C substituted with at least one selected from deuterium, -F, cyano, C1-C 60 Alkyl, phenyl, and biphenyl, C1-C 60 Alkyl, substituted with at least one selected from deuterium, -F, cyano, C1-C 10 Alkyl, phenyl, and biphenyl, C6-C 60 Aryl and C1-C substituted with at least one selected from deuterium, -F, cyano, C1-C 10 Alkyl, phenyl, and biphenyl, C1-C 60 Heteroaryl, but the embodiments of the present disclosure are not limited thereto.
[0113] In one embodiment, in Formula 1-1, B 11 to B 14 and R 11 to R 20 may each independently be selected from:
[0114] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and C1-C 20 Alkyl;
[0115] C1-C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and cyano 20 Alkyl;
[0116] Groups represented by Formula 5-1 to Formula 5-138; and
[0117] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), but the embodiments of the present disclosure are not limited thereto:
[0118]
[0119]
[0120]
[0121]
[0122]
[0123]
[0124] In Formulas 5-1 to 5-138,
[0125] X 51 may be selected from O, S, N(R 51 ), and C(R 51 )(R 60 ),
[0126] X 52 may be N or C(R 52 ), X 53 may be N or C(R 53 ), X 54 may be N or C(R 54 ), X 55 may be N or C(R 55 ), X 56 may be N or C(R 56 ), X 57 may be N or C(R 57 ), X 58 may be N or C(R 58 ), X 59 may be N or C(R 59 ),
[0127] R 51 to R 60 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, perylenyl, thienyl, furyl, silolyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, benzosilolyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, -C(Q 31 )(Q 32 )(Q 33 ), -Si(Q 31 )(Q 32 )(Q 33 ), -B(Q 31 )(Q 32 ), -N(Q 31 )(Q 32 ), -P(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 ),
[0128] Q1 to Q3 and Q 31 To Q 33 Can be independently selected from:
[0129] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl and naphthyl; and
[0130] substituted with at least one selected from deuterium and phenyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl and naphthyl,
[0131] b51 can be selected from 1, 2, 3, 4 and 5,
[0132] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,
[0133] b53 can be selected from 1, 2, 3, 4, 5, 6, 7, 8 and 9,
[0134] b54 can be selected from 1, 2, 3 and 4,
[0135] b55 can be selected from 1, 2 and 3,
[0136] b56 can be selected from 1 and 2,
[0137] b57 may be selected from 1, 2, 3, 4, 5 and 6, and
[0138] *Indicates the binding site with the adjacent atom.
[0139] In one embodiment, in Formula 1-1, B 11 To B 14 and R 11 To R 20 may be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and a group represented by one of Formulae 9-1 to 9-16;
[0140] is replaced with a group represented by one of Formula 9-1 to Formula 9-16, which is selected from at least one of deuterium, -F, -Cl, -Br, -I, and cyano; and
[0141] a group represented by one of Formula 6-1 to Formula 6-257, but the embodiments of the present disclosure are not limited thereto:
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152] In Formula 6-1 to Formula 6-257,
[0153] i-Pr represents isopropyl,
[0154] t-Bu represents tert-butyl,
[0155] Ph represents phenyl,
[0156] 1-Naph represents 1-naphthyl,
[0157] 2-Naph represents 2-naphthyl, and
[0158] * represents the bonding position to an adjacent atom.
[0159] In one embodiment, in Formula 1-1, R 11 to R 14 can each independently be selected from:
[0160] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and a group represented by Formula 9-1 to Formula 9-16;
[0161] a group represented by Formula 9-1 to Formula 9-16, which is all substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and cyano; and
[0162] Groups represented by Formula 6-1 to Formula 6-24, but the embodiments of the present disclosure are not limited thereto.
[0163] In one embodiment, in Formula 1-1, R 15 to R 20 may each independently be selected from:
[0164] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and groups represented by Formula 9-1 to Formula 9-16; and
[0165] groups represented by Formula 9-1 to Formula 9-16 each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and cyano, but the embodiments of the present disclosure are not limited thereto.
[0166] In Formula 1-1, b11 to b20 may each independently be an integer from 1 to 10.
[0167] In Formula 1-1, *1 to *4 each represent a binding site to M 11 .
[0168] In Formula 1-1, * and *' each represent a binding site to an adjacent atom.
[0169] In one embodiment, in Formula 1, L 11 may be a ligand represented by Formula 1-11, but the embodiments of the present disclosure are not limited thereto:
[0170] <Formula 1-11>
[0171]
[0172] In Formula 1-11,
[0173] X 11 to X 13 、Y 11 to Y 14 、T 11 to T 14 、ring A 11 to ring A 20 、R 11 to R 20 、b11 to b20 and *1 to *4 may each independently be the same as defined in Binding Formula 1-1, and
[0174] Y 11 and Z 11 、Y 12 and Z 12 、Y 12 and Z 13 、Y 13 and Z14 The bond between and Y 13 and Z 15 The bond between and Y 14 and Z 16 The bonds between can each independently be a single bond or a double bond.
[0175] For example, in Formula 1-11, Ring A 11 to Ring A 14 can each independently be selected from benzene, naphthalene, indene, fluorene, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, indole, carbazole, indeno[1,2-b]pyridine, indolo[1,2-b]pyridine, benzofuro[2,3-b]pyridine, benzothieno[2,3-b]pyridine, indeno[1,2-d]pyrimidine, indolo[1,2-d]pyrimidine, benzofuro[2,3-d]pyrimidine, benzothieno[2,3-d]pyrimidine, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, phenanthroline, pyrrole, pyrazole, imidazole, dihydroimidazole, triazole, dihydrotriazole, oxazole, dihydrooxazole, isoxazole, thiazole, dihydrothiazole, isothiazole, oxadiazole, dihydrooxadiazole, thiadiazole, dihydrothiadiazole, benzopyrazole, benzimidazole, dihydrobenzimidazole, imidazopyridine, imidazopyrimidine, imidazopyrazine, benzoxazole, dihydrobenzoxazole, benzothiazole, dihydrobenzothiazole, benzoxadiazole, dihydrobenzoxadiazole, benzothiadiazole, and dihydrobenzothiadiazole, and
[0176] Ring A 15 to Ring A 20 can each independently be selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, and isoquinoline, but the embodiments of the present disclosure are not limited thereto.
[0177] In one or more embodiments, L in Formula 1 11 can be a ligand represented by Formula 1-21, but the embodiments of the present disclosure are not limited thereto:
[0178] <Formula 1-21>
[0179]
[0180] In Formula 1-21,
[0181] Y 11 to Y 14 , Ring A 11 to Ring A 20 , R 11 to R 20 , b11 to b20, and *1 to *4 can each independently be the same as defined in Binding Formula 1-1,
[0182] Z 11 to Z 16 can each independently be N or C, and
[0183] Y11 The bond between and Z 11 and Y 12 The bond between and Z 12 and Y 12 The bond between and Z 13 and Y 13 The bond between and Z 14 and Y 13 The bond between and Z 15 and the bond between and Z, and Y 14 The bond between and Z 16 and can each independently be a single bond or a double bond.
[0184] For example, in Formulas 1-21, Ring A 11 to Ring A 14 can each independently be selected from benzene, naphthalene, indene, fluorene, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, indole, carbazole, indeno pyridine, indole pyridine, benzofuran pyridine, benzothiophene pyridine, indeno pyrimidine, indole pyrimidine, benzofuran pyrimidine, benzothiophene pyrimidine, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, phenanthroline, pyrrole, pyrazole, imidazole, dihydroimidazole, triazole, dihydrotriazole, oxazole, dihydrooxazole, isoxazole, thiazole, dihydrothiazole, isothiazole, oxadiazole, dihydrooxadiazole, thiadiazole, dihydrothiadiazole, benzopyrazole, benzimidazole, dihydrobenzimidazole, imidazopyridine, imidazopyrimidine, imidazopyrazine, benzoxazole, dihydrobenzoxazole, benzothiazole, dihydrobenzothiazole, benzoxadiazole, dihydrobenzoxadiazole, benzothiadiazole and dihydrobenzothiadiazole,
[0185] Ring A 15 to Ring A 20 can each independently be selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline and isoquinoline, but the embodiments of the present disclosure are not limited thereto.
[0186] L in Formula 1 12 can be selected from monodentate ligands and bidentate ligands.
[0187] For example, L in Formula 1 12 can be a ligand represented by one of Formulas 7-1 to 7-11, but the embodiments of the present disclosure are not limited thereto:
[0188]
[0189] In Formulas 7-1 to 7-11,
[0190] Ring A 71 and Ring A 72 can each independently be selected from C5-C 20 carbocyclic groups and C1-C20 heterocyclic group
[0191] X 71 and X 72 can each independently be selected from C and N
[0192] 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 ), X 77 can be N or C(Q 77 ),
[0193] X 78 can be O, S or N(Q 78 ), X 79 can be O, S or N(Q 79 ),
[0194] Y 71 and Y 72 can each independently be selected from a single bond, a double bond, a substituted or unsubstituted C1-C5 alkylene group, a substituted or unsubstituted C2-C5 alkenylene group, and a substituted or unsubstituted C6-C 10 arylene group
[0195] Z 71 and Z 72 can each independently be selected from N, O, N(R 75 ), P(R 75 )(R 76 ), and As(R 75 )(R 76 ),
[0196] Z 73 can be selected from P and As
[0197] Z 74 can be selected from CO and CH2
[0198] R 71 to R 73 、R 75 to R 80 and Q 73 to Q 79 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein, R 71 and R 72 may optionally be linked to form a ring, R 77 and R 78 may optionally be linked to form a ring, R 78 and R 79 may optionally be linked to form a ring, R 79 and R 80 may optionally be linked to form a ring,
[0199] b71 and b72 may each independently be selected from 1, 2, and 3, and
[0200] * and *' each independently represent a binding site to an adjacent atom.
[0201] For example, ring A in Formula 7-1, Formula 7-9, and Formula 7-11 71 and ring A 72 may each independently be selected from phenyl, naphthyl, imidazolyl, benzimidazolyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, and isoquinolinyl, but the embodiments of the present disclosure are not limited thereto.
[0202] For example, in Formula 7-1, Formula 7-9, and Formula 7-11, X 72 and X 79 may be N, but the embodiments of the present disclosure are not limited thereto.
[0203] For example, in Formula 7-7, X 73 may be C(Q 73 ), X 74 may be C(Q 74 ), X 75 may be C(Q 75 ), X 76 may be C(Q76 ),X 77 may be C(Q 77 ), but the embodiments of the present disclosure are not limited thereto.
[0204] For example, in Formulas 7-8, X 78 may be N(Q 78 ), X 79 may be N(Q 79 ), but the embodiments of the present disclosure are not limited thereto.
[0205] For example, in Formulas 7-2, 7-3, and 7-8, Y 71 and Y 72 may each independently be selected from substituted or unsubstituted methylene and substituted or unsubstituted phenylene, but the embodiments of the present disclosure are not limited thereto.
[0206] For example, in Formulas 7-1 and 7-2, Z 71 and Z 72 may each independently be O, but the embodiments of the present disclosure are not limited thereto.
[0207] For example, in Formula 7-4, Z 73 may be P, but the embodiments of the present disclosure are not limited thereto.
[0208] For example, in Formulas 7-1 to 7-8, R 71 to R 73 , R 75 to R 80 and Q 73 to Q 79 may each independently be selected from:
[0209] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 alkyl and C1-C 20 alkoxy;
[0210] C1-C 20 alkyl and C1-C 20 alkoxy each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, phenyl, naphthyl, pyridyl, and pyrimidinyl;
[0211] phenyl, naphthyl, fluorene, phenanthrene, anthracene, fluoranthene, benzo[9,10]phenanthrene, pyrene, a base, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, and imidazopyridinyl; and
[0212] are each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxyl or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, a phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl substituted with at least one selected from pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, and imidazopyridinyl, provided that the embodiments of the present disclosure are not limited thereto. a pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, and imidazopyridinyl, provided that the embodiments of the present disclosure are not limited thereto.
[0213] In one embodiment, L in Formula 1 12 can be represented by one of Formula 8-1 to Formula 8-11, in which Ph-d5 represents a phenyl group in which all hydrogen atoms are replaced by deuterium, provided that the embodiments of the present disclosure are not limited thereto:
[0214]
[0215] * indicates the binding site to adjacent atoms.
[0216] In Formula 1, n11 represents the number of L 11 , where n11 can be 1.
[0217] In Formula 1, n12 represents the number of L 12 , where n12 can be selected from 0, 1, and 2. When n12 is two, multiple L 12 can be the same as or different from each other.
[0218] In one embodiment, in Formula 1, n11 can be 1 and n12 can be 0.
[0219] In one or more embodiments, in Formula 1, n11 can be 1 and n12 can be 2.
[0220] In one or more embodiments, in Formula 1, M 11 can be selected from Pt and Pd, n11 can be 1, and n12 can be 0.
[0221] In one embodiment, the organometallic compound represented by Formula 1 can be selected from compounds BD1 to BD80 in Group I below, but the embodiments of the present disclosure are not limited thereto:
[0222] <Group I>
[0223]
[0224]
[0225]
[0226] Since the organometallic compound substantially includes a ring containing Ring A 15 , X 11 and Ring A 16 rings, rings containing Ring A 17 , X 12 and Ring A 18 rings, and rings containing Ring A 19 , X 13 and Ring A 20 rings (i.e., including three fused rings as a linking group), the formation of an exciplex (or "excited state complex") with the host is hindered compared to a compound including two fused rings as a linking group. Therefore, the efficiency of an electronic device (e.g., an organic light-emitting device) including the organometallic compound can be improved.
[0227] The organometallic compound can emit blue light having a maximum emission wavelength in the range of about 430 nm or greater and about 470 nm or less.
[0228] The method for synthesizing the organometallic compound represented by Formula 1 will be apparent to those of ordinary skill in the art by referring to the following examples.
[0229] At least one of the organometallic compounds of Formula 1 can be used between a pair of electrodes of an organic light-emitting device. Accordingly, there is provided an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode. The organic layer includes an emission layer, and the organic layer includes at least one organometallic compound represented by Formula 1.
[0230] As used herein, the expression “(the organic layer) includes at least one organometallic compound” can include the case where “(the organic layer) includes the same organometallic compound represented by Formula 1” and the case where “(the organic layer) includes two or more different organometallic compounds represented by Formula 1”.
[0231] For example, the organic layer can include only Compound 1 as the organometallic compound. In this regard, Compound 1 can be present only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer can include Compound 1 and Compound 2 as the organometallic compounds. In one or more embodiments, both Compound 1 and Compound 2 can be present in the same layer (e.g., both Compound 1 and Compound 2 can be present in the emission layer), or can be present in different layers (e.g., Compound 1 can be present in the emission layer and Compound 2 can be present in the electron transport layer).
[0232] The organic layer includes: i) a hole transport region disposed between the first electrode (anode) and the emission layer and including at least one of a hole injection layer, a hole transport layer, a buffer layer (hereinafter, may also be referred to as an “emission assist layer”), and an electron blocking layer; and / or ii) an electron transport region disposed between the emission layer and the second electrode (cathode) and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. The emission layer can include at least one organometallic compound represented by Formula 1.
[0233] In one or more embodiments, at least one of the hole transport region and the emission layer can include at least one selected from an arylamine compound-containing compound, an acridine compound-containing compound, and a carbazole compound-containing compound, and / or
[0234] At least one of the emission layer and the electron transport region may include at least one selected from a silicon-containing compound, a phosphine oxide-containing compound, a sulfur oxide-containing compound, a phosphorus oxide-containing compound, a triazine-containing compound, a pyrimidine-containing compound, a pyridine-containing compound, a dibenzofuran-containing compound, and a dibenzothiophene-containing compound.
[0235] Figure 1 's description]
[0236] Figure 1 is a schematic view of the organic light emitting device 10 according to an embodiment. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0237] Hereinafter, the structure of the organic light emitting device 10 according to an embodiment and a method of manufacturing the organic light emitting device 10 will be described in conjunction with Figure 1 to describe the structure of the organic light emitting device 10 according to an embodiment and a method of manufacturing the organic light emitting device 10.
[0238] [First electrode 110]
[0239] In Figure 1 , a substrate may be additionally provided under the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate that both have excellent mechanical strength, thermal stability, transparency, surface flatness, handleability, and waterproofness.
[0240] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the 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.
[0241] 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, the material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0242] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.
[0243] [Organic layer 150]
[0244] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.
[0245] 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.
[0246] [Hole transport region in the organic layer 150]
[0247] The hole transport region may have: i) a single-layer structure including a single layer containing a single material; ii) a single-layer structure including a single layer containing a plurality of different materials; or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0248] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.
[0249] For example, the hole transport region may have a single-layer structure or a multi-layer structure. The single-layer structure includes a single layer containing a plurality of different materials. The multi-layer structure has 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 / electron blocking layer structure. For each structure, the constituent layers are sequentially stacked in the stated order from the first electrode 110, but the structure of the hole transport region is not limited thereto.
[0250] 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''-tris(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), the compound represented by Formula 201, and the compound represented by Formula 202:
[0251]
[0252] <Formula 201>
[0253]
[0254] <Formula 202>
[0255]
[0256] In Formulas 201 and 202,
[0257] L 201 to L 204 can each independently be selected from substituted or unsubstituted C3-C 10 cycloalkanediyl, substituted or unsubstituted C1-C 10 heterocycloalkanediyl, substituted or unsubstituted C3-C 10 cycloalkenediyl, substituted or unsubstituted C1-C 10 heterocycloalkenediyl, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic fused polycyclic group, and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
[0258] L 205 can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C1-C 20 alkanediyl, substituted or unsubstituted C2-C 20 alkenediyl, substituted or unsubstituted C3-C 10 cycloalkanediyl, substituted or unsubstituted C1-C 10 heterocycloalkanediyl, substituted or unsubstituted C3-C 10 cycloalkenediyl, substituted or unsubstituted C1-C 10 heterocycloalkenediyl, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic fused polycyclic group, and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
[0259] xa1 to xa4 can each independently be an integer from 0 to 3,
[0260] xa5 can be an integer from 1 to 10, and
[0261] R 201 to R 204 and Q 201 can each independently be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.
[0262] For example, in Formula 202, R 201 and R 202 can optionally be connected via a single bond, dimethyl-methylene or diphenyl-methylene, and R 203 and R 204 can optionally be connected via a single bond, dimethyl-methylene or diphenyl-methylene.
[0263] In one embodiment, in Formula 201 and Formula 202,
[0264] L 201 to L 205 can each independently be selected from:
[0265] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulylene, heptalenylene, indacenylene, acenaphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, yl, tetracenylene, picenylene, pentaphenylene, hexacenylene, pentaphenylenyl, rubicenyl, coronenyl, ovalenyl, thienylene, furylene, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridinyl; and
[0266] each substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, cyclopentadienyl, indenyl, naphthyl, azulyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, A base, a tetracenyl, a picenyl, a perylenyl, a pentaphenylenyl, a hexacenyl, a pentacenyl, a rubicenyl, a coronenyl, an ovalenyl, a thienyl, a furyl, a carbazolyl, an indolyl, an isoindolyl, a benzofuranyl, a benzothienyl, a dibenzofuranyl, a dibenzothienyl, a benzocarbazolyl, a dibenzocarbazolyl, a dibenzosilolyl, a pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ), at least one selected from a phenylene, a s-indacenylene, an indanylene, a naphthylene, a azulylene, a heptaleneylene, an indenacenylene, an acenaphthylene, a fluoreneylene, a spirobifluoreneylene, a benzofluoreneylene, a dibenzofluoreneylene, an acenaphthylene, a phenanthrylene, an anthrylene, a fluoranthenylene, a benzo[9,10]phenanthrylene, a pyrenylene, a yl, a tetracenylene, a picenylene, a perylenylene, a pentaphenylenylene, a hexacenylene, a pentacenylene, a rubicenylene, a coronenylene, an ovalenylene, a thienylene, a furylene, a carbazolylene, an indolylene, an isoindolylene, a benzofuranylene, a benzothienylene, a dibenzofuranylene, a dibenzothienylene, a benzocarbazolylene, a dibenzocarbazolylene, a dibenzosilolylene and a pyridinylene, and
[0267] Q 31 to Q 33 can each independently be selected from C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0268] In one or more embodiments, xa1 to xa4 can each independently be 0, 1 or 2.
[0269] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0270] In one or more embodiments, R 201 to R 204 and Q 201 can each independently be selected from phenyl, biphenyl, terphenyl, s-indacenylene, indanylene, naphthylene, azulylene, heptaleneylene, indenacenylene, acenaphthylene, fluoreneylene, spirobifluoreneylene, benzofluoreneylene, dibenzofluoreneylene, acenaphthylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, yl, tetracenylene, picenylene, perylenylene, pentaphenylenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene, thienylene, furylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilolylene and pyridinylene; and
[0271] each is substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, bicyclopentadienyl, indenyl, naphthyl, azulyl, heptalene, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, base, tetraphenyl, picene, perylene, pentaphene, hexaphenyl, pentacene, rubicene, coronene, ovalene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ), and phenyl, biphenyl, terphenyl, bicyclopentadienyl, indenyl, naphthyl, azulyl, heptalene, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, base, tetraphenyl, picene, perylene, pentaphene, hexaphenyl, pentacene, rubicene, coronene, ovalene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridyl, and
[0272] Q 31 to Q 33 is the same as described above.
[0273] In one or more embodiments, at least one selected from R 201 to R 203 in Formula 201 may each independently be selected from:
[0274] fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl; and
[0275] each is substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20An alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C 10 alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and at least one selected from the group consisting of a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group of a dibenzothiophenyl group,
[0276] However, the embodiments of the present disclosure are not limited thereto.
[0277] In one or more embodiments, in Formula 202, i) R 201 and R 202 may be connected via a single bond, and / or ii) R 203 and R 204 may be connected via a single bond.
[0278] In one or more embodiments, in Formula 202, at least one selected from R 201 to R 204 may each independently be selected from:
[0279] a carbazolyl group; and
[0280] substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C 10 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 of a dibenzothiophenyl group,
[0281] However, the embodiments of the present disclosure are not limited thereto.
[0282] The compound represented by Formula 201 may be represented by Formula 201A:
[0283] <Formula 201A>
[0284]
[0285] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:
[0286] <Formula 201A(1)>
[0287]
[0288] In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A-1 below, but the embodiments of the present disclosure are not limited thereto:
[0289] <Formula 201A-1>
[0290]
[0291] In one embodiment, the compound represented by Formula 202 may be represented by Formula 202A:
[0292] <Formula 202A>
[0293]
[0294] In one embodiment, the compound represented by Formula 202 may be represented by Formula 202A-1:
[0295] <Formula 202A-1>
[0296]
[0297] In Formulas 201A, 201A(1), 201A-1, 202A, and 202A-1,
[0298] L 201 to L 203 , xa1 to xa3, xa5, and R 202 to R 204 are the same as described above,
[0299] R 211 and R 212 may each independently be the same as defined for binding R 203 and
[0300] R 213 to R 217 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, bicyclopentadienyl, indenyl, naphthyl, azulyl, heptaleneyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, Groups, tetracenyl, picenyl, perylenyl, pentaphenylenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridyl.
[0301] The hole transport region may include at least one compound selected from compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto:
[0302]
[0303]
[0304]
[0305] The thickness of the hole transport region may be about 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 in the range of about to about (e.g., about to about ), and the thickness of the hole transport layer may be in the range of about to about (e.g., about to about ). When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0306] The emission assisting layer can improve the light emission efficiency by compensating for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer may include the materials described above.
[0307] [p-dopant]
[0308] In addition to these materials, the hole transport region may further include a charge generation material for improving the conductive property. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.
[0309] The charge generation material may be, for example, a p-dopant.
[0310] In one embodiment, 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 cyanide-containing compounds, but the embodiments of the present disclosure are not limited thereto.
[0312] For example, the p-dopant may include at least one selected from the following compounds:
[0313] Quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0314] Metal oxides such as tungsten oxide or molybdenum oxide;
[0315] 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
[0316] The compound represented by Formula 221,
[0317] but the embodiments of the present disclosure are not limited thereto:
[0318]
[0319] <Formula 221>
[0320]
[0321] In Formula 221,
[0322] R 221 to R 223 may each independently be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one selected from R 221 to R 223 may include at least one substituent selected from cyano, -F, -Cl, -Br, -I, C1-C 20 alkyl substituted with -F, C1-C 20 alkyl substituted with -Cl, C1-C 20 alkyl substituted with -Br, and C1-C 20 alkyl substituted with -I.
[0323] [Emission layer in the organic layer 150]
[0324] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer according to sub-pixels. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0325] The emission layer may include a host and a dopant. The dopant may include an organometallic compound represented by Formula 1. In one or more embodiments, in addition to the organometallic compound represented by Formula 1, the dopant may further include at least one of a phosphorescent dopant and a fluorescent dopant.
[0326] Based on 100 parts by weight of the host, the amount of the dopant in the emission layer may be in the range of about 0.01 part by weight to about 15 parts by weight, but the embodiments of the present disclosure are not limited thereto.
[0327] The thickness of the emission layer may be about to about (e.g., about to about ) In this range. When the thickness of the emission layer is in this range, excellent light-emitting characteristics can be obtained without significantly increasing the driving voltage.
[0328] [Host in the emission layer]
[0329] In one or more embodiments, the host may include a compound represented by the following Formula 301.
[0330] <Formula 301>
[0331] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21
[0332] In Formula 301,
[0333] Ar 301 may be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,
[0334] xb11 can be 1, 2 or 3,
[0335] L 301 can be selected from substituted or unsubstituted C3-C 10 subcycloalkyl, substituted or unsubstituted C1-C 10 subheterocycloalkyl, substituted or unsubstituted C3-C 10 subcycloalkenyl, substituted or unsubstituted C1-C 10 subheterocycloalkenyl, substituted or unsubstituted C6-C 60 subaryl, substituted or unsubstituted C1-C 60 subheteroaryl, substituted or unsubstituted divalent non-aromatic fused polycyclic group and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
[0336] xb1 can be an integer from 0 to 5,
[0337] R 301 can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused 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 ),
[0338] xb21 can be an integer from 1 to 5, and
[0339] Q 301 to Q 303 can each independently be selected from C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments of the present disclosure are not limited thereto.
[0340] In one embodiment, Ar in Formula 301 301 can be selected from:
[0341] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, -yl, tetracenyl, picenyl, perylenyl, pentaphenyl, indenoanthracenyl, dibenzofuranyl, and dibenzothiophenyl; and
[0342] each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-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 ) of naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, -yl, tetracenyl, picenyl, perylenyl, pentaphenyl, indenoanthracenyl, dibenzofuranyl, and dibenzothiophenyl, and
[0343] Q 31 to Q 33 can each independently be selected from C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments of the present disclosure are not limited thereto.
[0344] When xb11 in Formula 301 is two or greater, two or more Ar 301 can be connected via a single bond.
[0345] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:
[0346] <Formula 301-1>
[0347]
[0348] <Formula 301-2>
[0349]
[0350] In Formula 301-1 and Formula 301-2,
[0351] Ring A 301 to Ring A 304 may each independently be selected from benzene, naphthalene, phenanthrene, fluoranthene, benzo[9,10]phenanthrene, pyrene, pyridine, pyrimidine, indene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthothiophene, benzonaphthothiophene, and dinaphthothiophene,
[0352] X 301 may be O, S, or N-[(L 304 ) xb4 -R 304 ,
[0353] R 311 to R 314 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-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 ),
[0354] xb22 and xb23 may each independently be 0, 1, or 2,
[0355] L301 , xb1, R 301 and Q 31 to Q 33 is the same as described above,
[0356] L 302 to L 304 can each independently be the same as combined with L 301 defined,
[0357] xb2 to xb4 can each independently be the same as combined with xb1 defined, and
[0358] R 302 to R 304 can each independently be the same as combined with R 301 defined.
[0359] For example, L in Formula 301, Formula 301-1 and Formula 301-2 301 to L 304 can each independently be selected from:
[0360] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzo[9,10]phenanthrylene, dibenzo[9,10]phenanthrylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, ylene, perylenylene, pentaphenylene, hexaphenylenylene, quaterphenylenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilolylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene and azacarbazolylene; and
[0361] each substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, 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, and
[0362] Q 31 To Q 33 Same as described above.
[0363] In one embodiment, R in Formula 301, Formula 301-1, and Formula 301-2 301 To R 304 Can be independently selected from:
[0364] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, perylenyl, pentaphenylenyl, hexaphenyl, quaterphenyl, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0365] all are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, perylenyl, pentaphenylenyl, hexaphenyl, quaterphenyl, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, 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 32phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, selected from at least one of group, perylenyl, pentaphenyl, hexaphenyl, pentacenyl, thiophenyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, and
[0366] Q 31 to Q 33 is the same as described above.
[0367] In one embodiment, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55), Mg complexes, and Zn complexes.
[0368] The host may be selected from 9,10 - bis(2 - naphthyl)anthracene (ADN), 2 - methyl - 9,10 - bis(naphthalen - 2 - yl)anthracene (MADN), 9,10 - bis(2 - naphthyl)-2 - tert - butyl - anthracene (TBADN), 4,4′ - bis(N - carbazolyl)-1,1′ - biphenyl (CBP), 1,3 - bis - 9 - carbazolylbenzene (mCP), 1,3,5 - tris(carbazol - 9 - yl)benzene (TCP), bis(4-(9H - carbazol - 9 - yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl - phosphine oxide (POPCPA), and compounds H1 to compound H55, but the embodiments of the present disclosure are not limited thereto:
[0369]
[0370]
[0371]
[0372]
[0373] In one or more embodiments, the host may include at least one selected from a silicon-containing compound (e.g., BCPDS used in the examples, etc.) and a phosphine oxide-containing compound (e.g., POPCPA used in the examples, etc.).
[0374] The host may include only one type of compound, or may include two or more different types of compounds (e.g., the host composition in the examples is BCPDS and POPCPA). Thus, the embodiments can be modified in various ways.
[0375] In one or more embodiments, the amount of the host in the emission layer may be greater than the amount of the organometallic compound represented by Formula 1 as a dopant.
[0376] [Electron transport region in organic layer 150]
[0377] The electron transport region may have: i) a single-layer structure including a single layer containing a single material; ii) a single-layer structure including a single layer containing multiple different materials; or iii) a multi-layer structure having multiple layers including multiple different materials.
[0378] 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.
[0379] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, where for each structure, the constituent layers are sequentially stacked in the stated order from the emission layer. However, the embodiments of the structure of the electron transport region are not limited thereto.
[0380] The electron transport region (e.g., the buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one π-electron-depleted nitrogen-containing ring (or π-electron-depleted nitrogen-containing ring).
[0381] "π-electron-depleted nitrogen-containing ring" means a C1-C 60 heterocyclic group having at least one *-N=*' moiety as a ring-forming moiety.
[0382] For example, a "π - electron - poor nitrogen - containing ring" can be: i) a 5 - to 7 - membered hetero - monocyclic group having at least one *-N=*' moiety; ii) a hetero - polycyclic group in which two or more 5 - to 7 - membered hetero - monocyclic groups each having at least one *-N=*' moiety are condensed with each other; or iii) a hetero - polycyclic group in which at least one of the 5 - to 7 - membered hetero - monocyclic groups each having at least one *-N=*' moiety is condensed with at least one C5 - C 60 carbocyclic group.
[0383] Examples of the π - electron - poor nitrogen - containing ring include, but are not limited to, 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.
[0384] For example, the electron - transporting region can include a compound represented by Formula 601:
[0385] <Formula 601>
[0386] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21 .
[0387] In Formula 601,
[0388] Ar 601 can be a substituted or unsubstituted C5 - C 60 carbocyclic group or a substituted or unsubstituted C1 - C 60 heterocyclic group,
[0389] xe11 can be 1, 2, or 3,
[0390] L 601 can be selected from substituted or unsubstituted C3 - C 10 subcycloalkyl, substituted or unsubstituted C1 - C 10 subheterocycloalkyl, substituted or unsubstituted C3 - C 10 subcycloalkenyl, substituted or unsubstituted C1 - C 10 subheterocycloalkenyl, substituted or unsubstituted C6 - C 60 subaryl, substituted or unsubstituted C1 - C 60 subheteroaryl, substituted or unsubstituted divalent non - aromatic condensed polycyclic group, and substituted or unsubstituted divalent non - aromatic condensed heteropolycyclic group,
[0391] xe1 can be an integer from 0 to 5,
[0392] R 601 may be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused 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 ),
[0393] Q 601 to Q 603 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and
[0394] xe21 can be an integer from 1 to 5.
[0395] In one embodiment, at least one selected from xe1 numbers of Ar 601 and xe21 numbers of R 601 may include a nitrogen-containing ring with electron-deficient π electrons.
[0396] In one embodiment, Ar in Formula 601 601 may be selected from:
[0397] phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, Groups, tetracenyl, picenyl, perylenyl, pentaphenylenyl, indenoanthracenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0398] are each independently substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-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 ), phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, groups, tetracenyl, picenyl, perylenyl, pentaphenylenyl, indenoanthracenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl, and
[0399] Q 31 to Q 33 can each independently be selected from C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0400] When xe11 in Formula 601 is two or greater, two or more Ar 601 can be connected via a single bond.
[0401] In one or more embodiments, Ar in Formula 601 601 can be anthracenyl.
[0402] In one or more embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:
[0403] <Formula 601-1>
[0404]
[0405] In Formula 601-1,
[0406] 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 ), wherein at least one selected from X 614 to X 616 can be N,
[0407] L 611 to L 613 can each independently be the same as defined for binding L 601 ,
[0408] xe611 to xe613 can each independently be the same as defined for binding xe1,
[0409] R 611 to R 613 can each independently be the same as defined for binding R 601 , and
[0410] R 614 to R 616 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0411] In one embodiment, L in Formula 601 601 and L in Formula 601-1 611 to L 613 can each independently be selected from:
[0412] phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzo[9,10]phenanthrylene, dibenzo[9,10]phenanthrylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, Groups, perylene diimide groups, pentacenequinone groups, hexacene groups, pentacene groups, thiophene diimide groups, furan diimide groups, carbazole diimide groups, indole diimide groups, isoindole diimide groups, benzofuran diimide groups, benzothiophene diimide groups, dibenzofuran diimide groups, dibenzothiophene diimide groups, benzocarbazole diimide groups, dibenzocarbazole diimide groups, dibenzosilole diimide groups, pyridine diimide groups, imidazole diimide groups, pyrazole diimide groups, thiazole diimide groups, isothiazole diimide groups, oxazole diimide groups, isoxazole diimide groups, thiadiazole diimide groups, oxadiazole diimide groups, pyrazine diimide groups, pyrimidine diimide groups, pyridazine diimide groups, s-triazine diimide groups, quinoline diimide groups, isoquinoline diimide groups, benzoquinoline diimide groups, phthalazine diimide groups, naphthyridine diimide groups, quinoxaline diimide groups, quinazoline diimide groups, cinnoline diimide groups, phenanthridine diimide groups, acridine diimide groups, phenanthroline diimide groups, phenazine diimide groups, benzimidazole diimide groups, isobenzothiazole diimide groups, benzoxazole diimide groups, isobenzoxazole diimide groups, triazole diimide groups, tetrazole diimide groups, imidazopyridine diimide groups, imidazopyrimidine diimide groups, and azacarbazole diimide groups; and
[0413] All are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, Groups, perylene groups, pentacenequinone groups, hexacene groups, pentacene groups, thiophene groups, furan groups, carbazole groups, indole groups, isoindole groups, benzofuran groups, benzothiophene groups, dibenzofuran groups, dibenzothiophene groups, benzocarbazole groups, dibenzocarbazole groups, dibenzosilole groups, pyridine groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, thiadiazole groups, oxadiazole groups, pyrazine groups, pyrimidine groups, pyridazine groups, s-triazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, phthalazine groups, naphthyridine groups, quinoxaline groups, quinazoline groups, cinnoline groups, phenanthridine groups, acridine groups, phenanthroline groups, phenazine groups, benzimidazole groups, isobenzothiazole groups, benzoxazole groups, isobenzoxazole groups, triazole groups, tetrazole groups, imidazopyridine groups, imidazopyrimidine groups, and azacarbazole groups of at least one selected from phenyl, naphthyl, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, sub- Groups such as a base, a perylene diimide group, a pentacenequinone group, a hexacenequinone group, a pentacene group, a thiophene group, a furan group, a carbazole group, an indole group, an isoindole group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzosilole group, a pyridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a thiadiazole group, an oxadiazole group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group,
[0414] However, the embodiments of the present disclosure are not limited thereto.
[0415] 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.
[0416] In one or more embodiments, R in Formula 601 601 and R in Formula 601-1 611 to R 613 may each independently be selected from:
[0417] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, a perylene diimide group, a pentacenequinone group, a hexacenequinone group, a pentacene group, a thiophene group, a furan group, a carbazole group, an indole group, an isoindole group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzosilole group, a pyridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a thiadiazole group, an oxadiazole group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group;
[0418] each substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20An alkoxy group, 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, 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, a perylenyl group, a pentaphenyl group, a hexaphenyl group, a quaterphenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, selected from at least one of
[0419] -S(=O)2(Q 601 ), and -P(=O)(Q 601 )(Q 602 ), and
[0420] Q 601 and Q 602 are the same as those described above.
[0421] The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but the embodiments of the present disclosure are not limited thereto:
[0422]
[0423]
[0424]
[0425]
[0426] In one or more embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 3P-T2T:
[0427]
[0428] The thickness of the buffer layer, hole blocking layer, or electron control layer may be from about to about (e.g., from about to about ). When the thicknesses of the buffer layer, hole blocking layer, and electron control layer are within these ranges, the electron transport region may have excellent hole blocking characteristics or electron control characteristics without significantly increasing the driving voltage.
[0429] The thickness of the electron transport layer may be from about to about For example, from about to about When the thickness of the electron transport layer is within the above range, satisfactory electron transport characteristics may be obtained without significantly increasing the driving voltage.
[0430] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metal-containing material.
[0431] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The alkali metal complex may include metal ions selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and the alkaline earth metal complex may include metal ions selected from Be ions, Mg ions, Ca ions, Sr ions, and Ba ions. Ligands coordinated to the metal ions of the alkali metal complex or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0432] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium 8-hydroxyquinoline, LiQ) or compound ET-D2:
[0433]
[0434] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0435] The electron injection layer may have: i) a single-layer structure including a single layer containing a single material; ii) a single-layer structure including a single layer containing a plurality of different materials; or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0436] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0437] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.
[0438] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
[0439] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
[0440] The alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.
[0441] The alkali metal compound may be selected from alkali metal oxides such as Li2O, Cs2O, or K2O and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or RbI. In one embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.
[0442] The alkaline earth metal compound may be selected from, such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) or Ba x Ca 1-xAlkaline earth metal oxides of O(0 < x < 1). In one embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.
[0443] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.
[0444] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex, or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0445] The electron injection layer may be composed of (or include) the 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 any combination thereof as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metal, 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 any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0446] The thickness of the electron injection layer may be about to about (e.g., about to about ). When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0447] [Second Electrode 190]
[0448] The second electrode 190 may be disposed on the organic layer 150 having such a structure. The second electrode 190 may be a cathode as an electron injection electrode, and in this regard, the material used to form the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.
[0449] 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.
[0450] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0451] Figures 2 to 4 description]
[0452] Figure 2 is a schematic diagram of an organic light emitting device 20 according to an embodiment. The organic light emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 sequentially stacked in the stated order. Figure 3 is a schematic diagram of an organic light emitting device 30 according to an embodiment. The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220 sequentially stacked in the stated order. Figure 4 is a schematic diagram of an organic light emitting device 40 according to an embodiment. The organic light emitting device 40 includes a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220 sequentially stacked in the stated order.
[0453] Regarding Figures 2 to 4 it, the first electrode 110, the organic layer 150, and the second electrode 190 can be understood by referring to the description given in conjunction with Figure 1 it.
[0454] In the organic layer 150 of each of the organic light emitting device 20 and the organic light emitting device 40, the light generated in the emission layer may pass through the first electrode 110 and the first cover layer 210 toward the outside, where the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light emitting device 30 and the organic light emitting device 40, the light generated in the emission layer may pass through the second electrode 190 and the second cover layer 220 toward the outside, where the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.
[0455] The first capping layer 210 and the second capping layer 220 can improve the external light-emitting efficiency according to the principle of constructive interference.
[0456] The first capping layer 210 and the second capping layer 220 can 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.
[0457] At least one selected from the first capping layer 210 and the second capping layer 220 can 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 can optionally be substituted with substituents containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 can each independently include an amine compound.
[0458] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 can each independently include a compound represented by Formula 201 or a compound represented by Formula 202.
[0459] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 can 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:
[0460]
[0461] Above, an organic light-emitting device according to an embodiment has been described, but the embodiments of the present disclosure are not limited thereto. Figures 1 to 4
[0462] Layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region can be formed in a certain region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0463] When forming layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region by vacuum deposition, considering the materials to be included in the layers to be formed and the structure of the layers to be formed, the deposition temperature can be from about 100 °C to about 500 °C, the vacuum degree can be from about 10 -8 Torr to about 10 -3 Torr, and about / second to about Perform vacuum deposition at a deposition rate of / second.
[0464] When forming the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region by spin coating, spin coating can be performed at a coating speed of about 2000 rpm to about 5000 rpm and at a heat treatment temperature of about 80 °C to about 200 °C by considering the materials included in the layer to be formed and the structure of the layer to be formed.
[0465] [Device]
[0466] The organic light emitting device can be included in various devices. For example, the device can include a thin film transistor and an organic light emitting device, and the thin film transistor includes a source electrode, a drain electrode, and an active layer.
[0467] One of the source electrode and the drain electrode can be electrically connected to the first electrode of the organic light emitting device.
[0468] The thin film transistor can further include a gate electrode, a gate insulating layer, etc.
[0469] The active layer can include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc., but the embodiments of the present disclosure are not limited thereto.
[0470] The device can further include a sealing portion for sealing the organic light emitting device. The sealing portion can display an image from the organic light emitting device and prevent external air and moisture from penetrating into the organic light emitting device. The sealing portion can be a sealing substrate including a transparent glass or plastic substrate. The sealing portion can be a thin film encapsulation layer including a plurality of organic layers and / or a plurality of inorganic layers. When the sealing portion is a thin film encapsulation layer, the entire flat device can be made flexible.
[0471] For example, the device can be used as a light emitting device, an authentication device, or an electronic device.
[0472] The light emitting device can be used as various displays, light sources, etc.
[0473] The authentication device can be, for example, a biometric authentication device for authenticating an individual by using biometric information of a living body (e.g., a fingertip, a pupil, etc.). In addition to the organic light emitting device, the authentication device can further include a biometric information collector.
[0474] The electronic device can be applied to a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic notepad, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a sphygmomanometer, a blood glucose meter, a pulse measuring device, a pulse wave measuring device, an electrocardiogram (ECG) monitor, an ultrasonic diagnostic device, or an endoscope monitor), a fish finder, various measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), a projector, etc., but the embodiments of the present disclosure are not limited thereto.
[0475] [General definition of substituents]
[0476] As used herein, the term "first row transition metal of the periodic table" refers to the elements in the fourth row of the periodic table and belonging to the d-block, examples of which include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn).
[0477] As used herein, the term "second row transition metal of the periodic table" refers to the elements in the fifth row of the periodic table and belonging to the d-block, examples of which include yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and cadmium (Cd).
[0478] As used herein, the term "third row transition metal of the periodic table" refers to the elements in the sixth row of the periodic table and belonging to the d-block and f-block, examples of which 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).
[0479] As used herein, the term "C1-C 60 alkyl" refers to a straight-chain or branched-chain aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C 60 alkylene" refers to a divalent group having the same structure as C1-C 60 alkyl.
[0480] As used herein, the term "C2-C 60 alkenyl" refers to a hydrocarbon group having at least one carbon-carbon double bond at the middle or end of C2-C 60 alkyl, examples of which include vinyl, propenyl, and butenyl. As used herein, the term "C2-C 60 alkenylene" refers to a divalent group having the same structure as C2-C 60 alkenyl.
[0481] As used herein, the term "C2-C 60 alkynyl" refers to a hydrocarbon group having at least one carbon-carbon triple bond at the middle or end of C2-C 60 alkyl, examples of which include ethynyl and propynyl. As used herein, the term "C2-C 60 alkynylene" refers to a divalent group having the same structure as C2-C 60An alkynyl group is a divalent group having the same structure.
[0482] As used herein, the term "C1-C 60 alkoxy" refers to a monovalent group represented by -OA 101 (wherein A 101 is a C1-C 60 alkyl group), and examples thereof include methoxy, ethoxy, and isopropoxy.
[0483] As used herein, the term "C3-C 10 cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C 10 cycloalkylidene" refers to a divalent group having the same structure as C3-C 10 cycloalkyl.
[0484] As used herein, the term "C1-C 10 heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms and 1 to 10 carbon atoms, and examples thereof include 1,2,3,4-oxadiazolyl, tetrahydrofuryl, and tetrahydrothienyl. As used herein, the term "C1-C 10 heterocycloalkylidene" refers to a divalent group having the same structure as C1-C 10 heterocycloalkyl.
[0485] As used herein, the term "C3-C 10 cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 cycloalkenylidene" refers to a divalent group having the same structure as C3-C 10 cycloalkenyl.
[0486] As used herein, the term "C1-C 10 heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms, 1 to 10 carbon atoms, and at least one double bond in its ring. Non-limiting examples of C1-C 10 heterocycloalkenyl include 4,5-dihydro-1,2,3,4-oxadiazolyl, 2,3-dihydrofuryl, and 2,3-dihydrothienyl. As used herein, the term "C1-C 10 heterocycloalkenylidene" refers to a divalent group having the same structure as C1-C 10 heterocycloalkenyl.
[0487] As used herein, the term "C6-C 60 aryl" refers to a monovalent group having a carbocyclic aromatic system comprising from 6 to 60 carbon atoms. As used herein, C6-C 60 arylene refers to a divalent group having a carbocyclic aromatic system comprising from 6 to 60 carbon atoms. Non-limiting examples of C6-C 60 aryl include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and yl. When both C6-C 60 aryl and C6-C 60 arylene include two or more rings, the rings may be fused to each other. As used herein, the term "C7-C 60 alkylaryl" refers to a C6-C 60 aryl substituted with at least one C1-C 60 alkyl.
[0488] As used herein, the term "C1-C 60 heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms in addition to 1 to 60 carbon atoms. As used herein, the term "C1-C 60 heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms in addition to 1 to 60 carbon atoms. Non-limiting examples of C1-C 60 heteroaryl include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When both C1-C 60 heteroaryl and C1-C 60 heteroarylene include two or more rings, the rings may be condensed to each other. As used herein, the term "C2-C 60 alkylheteroaryl" refers to a C1-C 60 heteroaryl substituted with at least one C1-C 60 alkyl.
[0489] As used herein, the term "C6-C 60 aryloxy" refers to -OA 102 (wherein A 102 is C6-C 60 aryl), and the term "C6-C 60 arylthio" as used herein denotes -SA 103 (wherein A 103 is C6-C 60 aryl).
[0490] As used herein, the term "C1-C 60 heteroaryloxy" denotes -OA104 (wherein, A 104 is C1-C 60 heteroaryl), as used herein the term "C1-C 60 heteroarylthio" means -SA 105 (wherein, A 105 is C1-C 60 heteroaryl).
[0491] As used herein the term "monovalent non-aromatic condensed polycyclic group" refers to a monovalent group having two or more rings fused to each other, only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring-forming atoms and not having aromaticity in its entire molecular structure. A detailed example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein the term "divalent non-aromatic condensed polycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
[0492] As used herein the term "monovalent non-aromatic condensed heteropolycyclic group" refers to a monovalent group having two or more rings fused to each other, at least one heteroatom selected from N, O, Si, P, and S in addition to carbon atoms (e.g., having 1 to 60 carbon atoms) as ring-forming atoms and not having aromaticity in its entire molecular structure. An example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. As used herein the term "divalent non-aromatic condensed heteropolycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0493] As used herein the term "C5-C 60 carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring-forming atoms are only carbon atoms. As used herein the term "C5-C 60 carbocyclic group" refers to an aromatic carbocyclic group or a non-aromatic carbocyclic group. A C5-C 60 carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl), or a divalent group (such as phenylene). In one or more embodiments, depending on the number of substituents attached to the C5-C 60 carbocyclic group, the C5-C 60 carbocyclic group can be a trivalent group or a tetravalent group.
[0494] As used herein the term "C1-C 60 heterocyclic group" refers to a group having the same structure as a C5-C 60 carbocyclic group except that at least one heteroatom selected from N, O, Si, P, and S in addition to carbon (the number of carbon atoms can range from 1 to 60) is used as a ring-forming atom.
[0495] In this specification, substituted C5-C 60 carbocyclic group, substituted C1-C60 Heterocyclic group, substituted C1-C 20 Alkylene, substituted C2-C 20 Alkenylene, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocycloalkylene, substituted C3-C 10 Cycloalkenylene, substituted C1-C 10 Heterocycloalkenylene, substituted C6-C 60 Arylene, substituted C1-C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkylaryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkylheteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, at least one substituent in the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0496] Deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy;
[0497] All substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkylheteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused 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 ) of at least one selected from C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 alkoxy;
[0498] C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group;
[0499] All are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C60 Aryl, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkylheteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused 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 ), at least one selected from C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkylheteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group; and
[0500] -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 ), and
[0501] Q 11 to Q 13 、Q 21 to Q23 and Q 31 to Q 33 may each independently be selected from hydrogen, deuterium, -F, -Cl,
[0502] -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, C1-C alkyl substituted with at least one selected from deuterium, -F and cyano, C6-C 60 aryl substituted with at least one selected from deuterium, -F and cyano, biphenyl and terphenyl. 60 As used herein, the term "Ph" refers to phenyl, the term "Me" refers to methyl, the term "Et" refers to ethyl, the term "ter-Bu (t-Bu)" or "Bu
[0503] " refers to tert-butyl, and the term "OMe" refers to methoxy. t As used herein, the term "biphenyl" refers to "phenyl substituted with phenyl". In other words, "biphenyl" is a substituted phenyl having a C6-C
[0504] aryl as a substituent. 60 As used herein, the term "terphenyl" refers to "phenyl substituted with biphenyl". In other words, "terphenyl" is a substituted phenyl having a C6-C
[0505] aryl substituted with a C6-C 60 aryl as a substituent. 60 Unless otherwise defined, *,' and " as used herein each refer to the binding position to an adjacent atom in the corresponding formula.
[0506] Unless otherwise defined, *,' and " as used herein each refer to the binding position to an adjacent atom in the corresponding formula.
[0507] Hereinafter, the compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in detail with reference to synthesis examples and examples. The expression "using B instead of A" used in the description of the synthesis examples means using the same molar equivalent of B instead of the same molar equivalent of A.
[0508] [Examples]
[0509] Synthesis Example 1: Synthesis of Compound BD1
[0510] Compound BD1 was synthesized with reference to Scheme I.
[0511] [Scheme I]
[0512]
[0513] (1) Synthesis of Intermediate 1-1
[0514] Compound A was reacted with nBuLi and then with 3-bromobenzaldehyde to synthesize Intermediate 1-1. Intermediate 1-1 was identified by LC-MS.
[0515] C 19 H 15 BrO: M+1 340.15.
[0516] (2) Synthesis of Intermediate 1-2
[0517] At room temperature, in dichloromethane (MC) solvent, Intermediate 1-1 was reacted with pyridinium chlorochromate (PCC) (cas: 26299-14-9) to synthesize Intermediate 1-2. Intermediate 1-2 was identified by LC-MS.
[0518] C 19 H 13 BrO: M+1 337.13.
[0519] (3) Synthesis of Intermediate 1-3
[0520] In the presence of an iodine catalyst, 2-bromopyridine (cas: 109-04-6) was activated with magnesium and reacted with Intermediate 1-2 to synthesize Intermediate 1-3. Intermediate 1-3 was identified by LC-MS.
[0521] C 24 H 18 BrNO: M+1 417.57.
[0522] (4) Synthesis of Intermediate 1-4
[0523] In AcOH solvent, Intermediate 1-3 was reacted with hydrochloric acid (cas: 7647-01-0) to obtain Intermediate 1-4. Intermediate 1-4 was identified by LC-MS.
[0524] C 24 H 16 BrN: M+1 399.92.
[0525] (5) Synthesis of Intermediate 1-5
[0526] React compound A with nBuLi, and then react with isophthalaldehyde to synthesize Intermediate 1-5. Intermediate 1-5 is identified by LC-MS.
[0527] C 32 H 26 O2: M+1 443.18.
[0528] (6) Synthesis of Intermediate 1-6
[0529] At room temperature, in dichloromethane solvent, react Intermediate 1-5 with pyridinium chlorochromate (cas: 26299-14-9) to synthesize Intermediate 1-6. Intermediate 1-6 is identified by LC-MS.
[0530] C 32 H 22 O2: M+1 438.53.
[0531] (7) Synthesis of Intermediate 1-7
[0532] React Intermediate 1-4 with nBuLi, and then react with Intermediate 1-6 to synthesize Intermediate 1-7. Intermediate 1-7 is identified by LC-MS.
[0533] C 56 H 39 NO2: M+1 757.95.
[0534] (8) Synthesis of Intermediate 1-8
[0535] In dichloromethane solvent, react Intermediate 1-7 with pyridinium chlorochromate (cas: 26299-14-9) to synthesize Intermediate 1-8. Intermediate 1-8 is identified by LC-MS.
[0536] C 56 H 37 NO: M+1 739.90.
[0537] (9) Synthesis of Intermediate 1-9
[0538] React Intermediate 1-8 with imidazole (cas: 288-32-4) and potassium carbonate to synthesize Intermediate 1-9. Intermediate 1-9 is identified by LC-MS.
[0539] C 59H 41 N3O: M+1 808.22.
[0540] (10) Synthesis of Intermediate 1-10
[0541] At room temperature, in dichloromethane solvent, Intermediate 1-9 was reacted with pyridinium chlorochromate (cas: 26299-14-9) to synthesize Intermediate 1-10. Intermediate 1-10 was identified by LC-MS.
[0542] C 59 H 39 N3: M+1 789.99.
[0543] (11) Synthesis of Intermediate 1-11
[0544] In acetone solvent, Intermediate 1-10 was reacted with methyl iodide (cas: 74-88-4) to synthesize Intermediate 1-11. Intermediate 1-11 was identified by LC-MS.
[0545] C 60 H 42 N3: M+1 805.22.
[0546] (12) Synthesis of Compound BD1
[0547] At a temperature of 160 °C, in 1,4-dioxane solvent, Intermediate 1-11, dichloro(1,5-cyclooctadiene)platinum(II), and sodium acetate were reacted with each other to synthesize Compound BD1. Compound BD1 was identified by LC-MS.
[0548] C 60 H 39 N3Pt: M+1 997.08.
[0549] Synthesis Example 2: Synthesis of Compound BD2
[0550] Compound BD2 was synthesized with reference to Scheme II and Synthesis Example 1.
[0551] <Scheme II>
[0552]
[0553] Compound BD2 was identified by LC-MS.
[0554] C 61 H 41 N3Pt: M+1 1011.12.
[0555] Synthesis Example 3: Synthesis of Compound BD3
[0556] Compound BD3 was synthesized with reference to Protocol III and Synthesis Example 1.
[0557] <Protocol III>
[0558]
[0559] Compound BD3 was identified by LC-MS.
[0560] C 63 H 45 N3Pt: M+1 1039.25.
[0561] Synthesis Example 4: Synthesis of Compound BD4
[0562] Compound BD4 was synthesized with reference to Protocol IV and Synthesis Example 1.
[0563] <Protocol IV>
[0564]
[0565] Compound BD4 was identified by LC-MS.
[0566] C 64 H 47 N3Pt: M+1 1053.24.
[0567] Synthesis Example 5: Synthesis of Compound BD5
[0568] Compound BD5 was synthesized with reference to Protocol V and Synthesis Example 1.
[0569] <Protocol V>
[0570]
[0571] Compound BD5 was identified by LC-MS.
[0572] C 68 H 47 N3Pt: M+1 1101.22.
[0573] Example 1
[0574] The ITO substrate with ITO / Ag / ITO deposited thereon as the anode was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The ITO substrate was provided to a vacuum deposition apparatus.
[0575] Compound 2-TNATA was vacuum deposited on an ITO substrate to form a hole injection layer with a thickness of 60 nm, and NPB was vacuum deposited on the hole injection layer to form a hole transport layer with a thickness of 30 nm.
[0576] Compound H56 (host) and Compound BD1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 10:1 to form an emission layer with a thickness of 25 nm.
[0577] BAlq was deposited on the emission layer to form a hole blocking layer with a thickness of 5 nm, Alq3 was deposited on the hole blocking layer to form an electron transport layer with a thickness of 25 nm, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.5 nm, and Al was deposited on the electron injection layer to form a cathode with a thickness of 150 nm, thus completing the fabrication of the organic light-emitting device.
[0578] Comparative Examples 1 to 4
[0579] An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compounds shown in Table 1 were used respectively when forming the emission layer.
[0580] Evaluation Example
[0581] The driving voltage (V), current density (mA / cm 2 ), luminous efficiency (cd / A), maximum emission wavelength (nm), and lifetime (T 2 ) of the organic light-emitting devices fabricated according to Example 1 and Comparative Examples 1 to 4 were measured at 1000 cd / m 90 using a Keithley SMU 236 and a luminance meter PR650, and the results are shown in Table 1. In Table 1, the lifetime (T 90 ) represents the amount of time elapsed when the luminance is 90% of the initial luminance (100%).
[0582] [Table 1]
[0583]
[0584]
[0585]
[0586] Referring to Table 1, it was confirmed that the luminous efficiency and lifetime of the organic light-emitting device of Example 1 were superior to those of the organic light-emitting devices of Comparative Examples 1 to 4.
[0587] The organic light-emitting device can have high efficiency and long lifetime.
[0588] It should be understood that the embodiments described herein should be considered only in a descriptive sense and not for purposes of limitation. The description of features or aspects within each embodiment should generally be considered applicable to other similar features or aspects in other embodiments.
[0589] Although one or more embodiments have been described with reference to the accompanying drawings, those of ordinary skill in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the claims.
Claims
1. An organometallic compound represented by Formula 1: <Formula 1> M 11 (L 11 ) n11 , Among them, In Formula 1, M 11 selected from platinum and palladium, L 11 is a ligand represented by Formula 1-1, n11 is 1: <Formula 1-1> Wherein, in Formula 1-1, T 11 to T 14 are all single bonds, R 11 to R 20 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, phenyl which is unsubstituted or substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, methyl, ethyl, propyl, isobutyl, sec-butyl and tert-butyl, b15 to b20 are each independently an integer from 1 to 4, *1 to *4 all represent binding sites to M 11 and Among them, the group represented by is the group represented by Formula 3-11, the group represented by is the group represented by Formula 3-21, the group represented by is the group represented by Formula 3-31, and the group represented by is represented by Formula 3-41: Wherein, in Formula 3-11, Formula 3-21, Formula 3-31 and Formula 3-41, *, *' and *" each represent a bonding site to an adjacent atom, R 11a , R 11b and R 11c are independently combined with R in formula 1-1 11 The same definition, R 12a 、R 12b and R 12c are each independently the same as defined by R 12 in Formula 1-1, R 13a , R 13b and R 13c are independently combined with R in formula 1-1 13 are defined identically, and R 14a 、R 14b 、R 14c and R 14d are each independently the same as the R 14 defined in Formula 1-1, Among them, the group represented by is the group represented by Formula 10-1, the group represented by is the group represented by Formula 11-1, and the group represented by is the group represented by Formula 12-1: Wherein, in Formula 10-1, Formula 11-1 and Formula 12-1, * and *' each represent a bonding site to an adjacent atom, and R 15 to R 20 and b15 to b20 are each independently the same as defined in Binding Formula 1-1.
2. The organometallic compound according to claim 1, wherein, M 11 Selected from Pt.
3. The organometallic compound according to claim 1, wherein, The organometallic compound represented by Formula 1 is selected from Compound BD1 to Compound BD5 and Compound BD51 to Compound BD80 of Group I: <Group I> 4. An organic light-emitting device, comprising: A first electrode; A second electrode; And An organic layer located between the first electrode and the second electrode and including an emission layer, Wherein, the organic layer includes the organometallic compound according to claim 1.
5. The organic light-emitting device according to claim 4, wherein, The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region located between the first electrode and the emission layer and / or an electron transport region located between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof.
6. The organic light-emitting device according to claim 4, wherein, The emission layer includes the organometallic compound.
7. A device, comprising: A thin-film transistor including a source electrode, a drain electrode and an active layer; And The organic light-emitting device according to claim 4, Wherein, the first electrode of the organic light-emitting device is electrically connected to one of the source electrode and the drain electrode of the thin-film transistor.
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