Organic metal compound and organic light-emitting device including the same
By using the optimized design organic metal compounds in the transmitting layer of the organic luminous device, the problem of insufficient efficiency and stability of the existing materials is solved, and a more efficient and lasting light emission effect is achieved.
Patent Information
- Application Number
- CN202011277435.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-11-28
- Filing Date
- 2020-11-16
- Publication Date
- 2025-01-28
- Estimated Expiration
- 2040-11-16
AI Technical Summary
The material efficiency and stability of the existing organic light emitting devices in the emitting layer are insufficient, resulting in poor luminous efficiency and lifetime.
The organic metal compound M (LA) N1 (LB) N2 represented by Formula 1 is used as the main material in the transmitted layer. M is the transition metal and LA and LB are different types of ligands. Design, improve the quantum yield and structural stability of the material.
The launch efficiency and life of the organic light -emitting device is improved, the quantum yield and structural stability of the material are enhanced, and the more efficient light launch is achieved.
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Figure CN112851713B_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0156111 filed in the Korean Intellectual Property Office on November 28, 2019, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more embodiments of the present disclosure are directed to an organometallic compound, an organic light-emitting device including the same, and an apparatus including the organic light-emitting device. Background Art
[0004] Organic light-emitting devices are self-emissive devices that produce full-color images and also have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] An example of an organic light-emitting device may include a first electrode located on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode located on the first electrode in sequence. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers (such as holes and electrons) recombine in the emission layer to generate excitons. These excitons transition from an excited state to (e.g., transition and relax) a ground state, thereby generating light. Summary of the invention
[0006] One or more embodiments include an organometallic compound, an organic light-emitting device including the same, and an apparatus including the organic light-emitting device.
[0007] Additional aspects of the embodiments 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 of the disclosure.
[0008] Aspects of embodiments of the present disclosure provide an organometallic compound represented by Formula 1.
[0009] Formula 1
[0010] M(L a ) n1 (L b ) n2
[0011] In formula 1,
[0012] M is selected from the group consisting of 1-period transition metals, 2-period transition metals and 3-period transition metals,
[0013] L a The ligand represented by the optional free form 2,
[0014] n1 can be 1 or 2,
[0015] L b can be selected from monodentate ligands, bidentate ligands and tridentate ligands,
[0016] n2 may be 0, 1, 2 or 3, and when n2 is 2 or greater, two or more L b may be the same or different from each other,
[0017] L a and L b Can be different from each other,
[0018] Formula 2
[0019]
[0020] Among them, in formula 2,
[0021] A 1 and A 2 Can be independently selected from C 5 -C 30 Carbocyclic and C 1 -C 30 Heterocyclic group,
[0022] X 1 , X 2 , X 3 and X 4 can be independently C or N,
[0023] Y 1 and Y 2 can be independently C or N,
[0024] T 1 、T 2 and T 3 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 4 )(B 5 )-*'、*-Si(R 4 )(R 5 )-*'、*-B(R 4 )-*'、*-N(R 4 )-*' and *-P(R 4 )-*',
[0025] b1 to b3 are each independently an integer of 1, 2 or 3,
[0026] R 1 To R 5can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0027] R 1 To R 3 Optionally, via a single bond, -C(Q 4 )(Q 5 )-、-Si(Q 4 )(Q 5 )-、-O-、-S-、-N(Q 4 )-、-B(Q 4 )-、-C(=O)-、-S(=O)2 -、-S(=O)(Q 4 )(Q 5 )-or-P(=O)(Q 4 )- is connected to an adjacent group to form an unsubstituted or substituted C 5 -C 30 Carbocyclic or unsubstituted or substituted C 1 -C 30 Heterocyclic group,
[0028] a1 and a2 may each independently be an integer selected from 0 to 10,
[0029] a3 can be 0, 1 or 2,
[0030] Substituted C 5 -C 30 Carbocyclic, substituted C 1 -C 30 Heterocyclic, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from:
[0031] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C60 Alkoxy,
[0032] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, 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 ),
[0033] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,
[0034] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl and terphenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl, terphenyl, -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 ),as well as
[0035] -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 ),
[0036] Where Q 1 To Q 5 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Alkyl substituted C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,
[0037] * 1 ,* 2and* 3 Each is a binding site with the central metal M of Formula 1, and
[0038] * and *' each indicate a binding site with an adjacent atom.
[0039] Another aspect of the embodiment provides an organic light-emitting device including a first electrode, a second electrode, and an organic layer including an emission layer between the first electrode and the second electrode, wherein the organic layer includes at least one organic metal compound. BRIEF DESCRIPTION OF THE DRAWINGS
[0040] The above and other aspects and features of certain embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0041] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;
[0042] Figure 2 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment;
[0043] Figure 3 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment; and
[0044] Figure 4 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment. DETAILED DESCRIPTION
[0045] Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the description set forth herein. Accordingly, the embodiments are described below simply by reference to the figures to explain aspects of the present description. As used herein, the term "and / or" includes any and all combinations of one or more associated enumerated items. Throughout this disclosure, the expression "at least one of a, b, and c" indicates only a, only b, only c, both a and b, both a and c, both b and c, all a, b, and c, or variations thereof.
[0046] Hereinafter, embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. The same or corresponding components will be represented by the same reference numerals, and thus, their redundant description will not be repeated here.
[0047] As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0048] It should be further understood that, as used herein, the terms “comprises” and / or “comprising” specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.
[0049] It should be understood that when a layer, region or component is referred to as being "on" or "onto" another layer, region or component, it can be formed directly or indirectly on the other layer, region or component. That is, for example, there may be intervening layers, regions or components.
[0050] For the convenience of explanation, the size of the elements in the drawings may be exaggerated. In other words, since the size and thickness of the components in the drawings may be arbitrarily explained for the convenience of explanation, the following embodiments of the present disclosure are not limited thereto.
[0051] As used herein, the term "organic layer" refers to a single layer and / or multiple layers between a first electrode and a second electrode of an organic light-emitting device. The materials included in the "organic layer" are not limited to organic materials. For example, the "organic layer" may include inorganic materials.
[0052] The organometallic compound in one embodiment is represented by the following Formula 1:
[0053] Formula 1
[0054] M(L a ) n1 (L b ) n2
[0055] M in Formula 1 may be selected from 1-period transition metals, 2-period transition metals, and 3-period transition metals.
[0056] In one embodiment, M may be selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), iridium (Ir), rhodium (Rh), cobalt (Co), (Mt), 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.
[0057] For example, M may be selected from iridium (Ir), cobalt (Co), rhodium (Rh), and (Mt).
[0058] n1 in Formula 1 can be 1 or 2.
[0059] L in Formula 1 a The ligand represented by the optional free form 2;
[0060] Formula 2
[0061]
[0062] Further details of Formula 2 are provided herein below.
[0063] In formula 1, L b can be selected from a monodentate ligand, a bidentate ligand and a tridentate ligand, and n2 can be 0, 1, 2 or 3, and when n2 is 2 or more, two or more L b They may be the same or different from each other. b for further details.
[0064] L in Formula 1 a and L b Can be different from each other.
[0065] In one embodiment, in Formula 1, M may be selected from iridium (Ir), cobalt (Co), rhodium (Rh) and (Mt), n1 can be 1, and n2 can be 1, 2 or 3.
[0066] For example, M may be iridium (Ir), n1 may be 1, and n2 may be 1.
[0067] A in Formula 2 1 and A 2 Can be independently selected from C 5 -C 30 Carbocyclic and C 1 -C 30 Heterocyclic group.
[0068] In one embodiment, A 1 and A 2 Can be independently selected from:
[0069] i) a first ring, ii) a second ring, iii) a fused cyclic group in which two or more first rings are fused to each other (e.g., combined together), iv) a fused cyclic group in which two or more second rings are fused to each other (e.g., combined together), or v) a fused cyclic group in which at least one first ring is fused to at least one second ring,
[0070] wherein the first ring can be selected from cyclopentyl, cyclopentenyl, cyclopentadienyl, furanyl, thienyl, pyrrolyl, borocyclopentadienyl, phospholyl, thiole, germanocyclopentadienyl, selenophenyl, oxazolyl, dihydrooxazolyl, isoxazolyl, dihydroisoxazolyl, oxadiazolyl, dihydrooxadiazolyl, isoxadiazolyl, dihydroisoxadiazolyl, oxatriazolyl, dihydrooxatriazolyl, isoxatriazolyl, dihydroisoxatriazolyl, oxazolyl, thiazolyl, dihydrothiazolyl, isothiazolyl, dihydroisothiazolyl, thiadiazolyl, dihydrothiadiazolyl, isothiadiazolyl, dihydroisothiadiazolyl, thiatriazolyl, dihydrothiatriazolyl, isothiatiazolyl, dihydroisothiatriazolyl, pyrazolyl, dihydropyrazolyl, imidazolyl, dihydroimidazolyl, triazolyl, dihydrotriazolyl, tetrazolyl, dihydrotetrazolyl, azathiarolyl, diazathiarolyl and triazathiarolyl, and
[0071] 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 embodiments of the present disclosure are not limited thereto.
[0072] In one or more embodiments, A 1 and A 2 The phenyl group may be independently selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, furanyl, thienyl, thirol, indenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, indolyl, carbazolyl, indenopyridinyl, indolopyridinyl, benzofuranopyridinyl, benzothienopyridinyl, benzothiarrolopyridinyl, indenopyrimidinyl, indolopyrimidinyl, benzofuranopyrimidinyl, benzothienopyrimidinyl, benzothiarrolopyridinyl, The invention also includes pyrimidinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phthalazinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, and benzothiadiazolyl, but the embodiments of the present disclosure are not limited thereto.
[0073] In one or more embodiments, A 1 and A 2The phenyl radicals may be independently selected from phenyl, naphthyl, indenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzothioyl, dibenzothioyl, indolyl, carbazolyl, indenopyridinyl, indolopyridinyl, benzofuranopyridinyl, benzothienopyridinyl, benzothioylpyridinyl, indenopyrimidinyl, indolopyrimidinyl, benzofuranopyrimidinyl, phenyl The invention also includes thienopyrimidinyl, benzothiazolyl, pyrimidinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzopyrazolyl, benzimidazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl and benzothiadiazolyl, but the embodiments of the present disclosure are not limited thereto.
[0074] X in Formula 2 1 , X 2 , X 3 and X 4 They may each independently be C or N.
[0075] In one embodiment, (i) X 1 Can be C, X 2 Can be C, X 3 Can be C, and X 4 Can be C; (ii) X 1 Can be N, X 2 Can be C, X 3 Can be C, and X 4 Can be C; (iii) X 1 Can be C, X 2 Can be N, X 3 Can be C, and X 4 Can be C; (iv) X 1 Can be C, X 2 Can be C, X 3 Can be N, and X 4 Can be C; (v) X 1 Can be C, X 2 Can be C, X 3 Can be C, and X 4 Can be N; (vi) X 1 Can be N, X 2 Can be N, X 3 Can be C, and X 4 Can be C; (vii) X 1 Can be N, X 2 Can be C, X 3 Can be N, and X 4 Can be C; (viii) X 1 Can be N, X 2 Can be C, X 3Can be C, and X 4 Can be N; (ix) X 1 Can be C, X 2 Can be N, X 3 Can be N, and X 4 Can be C; (x)X 1 Can be C, X 2 Can be N, X 3 Can be C, and X 4 Can be N; (xi) X 1 Can be C, X 2 Can be C, X 3 Can be N, and X 4 Can be N; (xii) X 1 Can be N, X 2 Can be N, X 3 Can be N, and X 4 Can be C; (xiii) X 1 Can be N, X 2 Can be N, X 3 Can be C, and X 4 Can be N; or (xiv) X 1 Can be N, X 2 Can be C, X 3 Can be N, and X 4 Can be N; (xv) X 1 Can be N, X 2 Can be N, X 3 Can be N, and X 4 Can be N.
[0076] Y in Formula 2 1 and Y 2 They may each independently be C or N.
[0077] For example, (i) Y 1 Can be C and Y 2 Can be C; (ii) Y 1 Can be C and Y 2 Can be N; (iii) Y 1 Can be N and Y 2 Can be C; or (iv) Y 1 Can be N and Y 2 Can be N.
[0078] T in Formula 2 1 , T 2 and T 3 can be independently a single bond, *-O-*', *-S-*', *-C(R 4 )(R 5 )-*'、*-Si(R 4 )(R5 )-*'、*-B(R 4 )-*'、*-N(R 4 )-*' and *-P(R 4 )-*'.
[0079] In one embodiment, T 1 , T 2 and T 3 Can be a single bond.
[0080] In one embodiment, T 1 , T 2 and T 3 At least one of the following can be selected from *-O-*', *-S-*', *-C(R 4 )(R 5 )-*'、*-Si(R 4 )(R 5 )-*'、*-B(R 4 )-*'、*-N(R 4 )-*' and *-P(R 4 )-*'.
[0081] In one or more embodiments, T 1 and T 2 At least one of the following can be selected from *-O-*', *-S-*', *-C(R 4 )(B 5 )-*'、*-Si(R 4 )(R 5 )-*'、*-B(R 4 )-*'、*-N(R 4 )-*' and *-P(R 4 )-*',and
[0082] T 3 Can be a single bond.
[0083] For example, T 1 and T 3 can each be a single bond, and T 2 Can be selected from *-O-*', *-S-*', *-C(R 4 )(B 5 )-*'、*-Si(R 4 )(R 5 )-*'、*-B(R 4 )-*'、*-N(R 4 )-*' and *-P(R 4 )-*'.
[0084] In one or more embodiments, T 1and T 3 Can be a single bond and T 2 Can be *-O-*'.
[0085] b1 to b3 in Formula 2 may each independently be an integer of 1, 2 or 3.
[0086] In one embodiment, b1 to b3 may each be 1.
[0087] R in Formula 2 1 To R 5 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ).
[0088] In one embodiment, R 1 To R 5 Can be independently selected from:
[0089] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0090] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, and terphenyl;
[0091] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, silolyl , imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzothioxyl, 1-dibenzo-1-pyrrolyl, ...
[0092] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl , benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, dinaphthofuranyl , dinaphthothienyl, dinaphthothioyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl: deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiophene oxazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, naphthobenzothioxyl, naphthobenzothioxyl, dibenzocarbazolyl oxazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolepyrrolyl, indenocarbazolyl, indolecarbazolyl, -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 );as well as
[0093] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),
[0094] Where Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 Alkyl, selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C6 -C 60 Aryl, and a group selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 However, the embodiments of the present disclosure are not limited thereto.
[0095] In one embodiment, R 1 To R 5 Can be independently selected from:
[0096] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0097] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, and terphenyl.
[0098] For example, R 1 To R 5 Can be independently selected from:
[0099] hydrogen, deuterium, -F, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl; and
[0100] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, each of which is substituted with at least one selected from the group consisting of deuterium, -F and cyano, but the embodiments of the present disclosure are not limited thereto.
[0101] R in Formula 2 1 To R 3 Optionally, via a single bond, -C(Q 4 )(Q 5 )-、-Si(Q 4 )(Q 5 )-、-O-、-S-、-N(Q 4 )-、-B(Q 4 )-、-C(=O)-、-S(=O) 2 -、-S(=O)(Q 4 )(Q 5 )-or-P(=O)(Q 4 )- is connected to an adjacent group to form an unsubstituted or substituted C5 -C 30 Carbocyclic or unsubstituted or substituted C 1 -C 30 Heterocyclic group.
[0102] a1 and a2 in Formula 2 may each independently be an integer selected from 0 to 10.
[0103] a3 in Formula 2 can be 0, 1 or 2.
[0104] In one embodiment, Formula 2 may be represented by Formula 2-1 or Formula 2-2:
[0105]
[0106] In formula 2-1 and formula 2-2,
[0107] A 1 , A 2 , R 1 , R 2 , a1, a2, X 3 , X 4 , Y 1 , Y 2 , T 1 , T 2 , T 3 , b1, b2, b3, * 1 ,* 2 and* 3 Same as described above, and R 31 , R 32 , R 33 , R 34 , R 35 and R 36 Each combined with R 3 Same as described.
[0108] In one embodiment, L in Formula 1 b It can be a tridentate ligand, and n2 can be 1.
[0109] In one embodiment, L b Optional free form 3 represents the ligand:
[0110] Formula 3
[0111]
[0112] In formula 3,
[0113] A 11 Can be selected from C 5 -C 30 Carbocyclic and C 1 -C 30Heterocyclic group,
[0114] L 1 and L 2 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 14 )(R 15 )-*'、*-Si(R 14 )(R 15 )-*'、*-B(R 14 )-*'、*-N(R 14 )-*' and *-P(R 14 )-*',
[0115] c1 and c2 can each independently be 1, 2 or 3,
[0116] X 11 , X 12 , X 13 and X 14 can be independently C or N,
[0117] Y 11 Can be C or N,
[0118] T 11 , T 12 and T 13 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*'、*-Si(R 16 )(R 17 )-*'、*-B(R 16 )-*'、*-N(R 16 )-*' and *-P(R 16 )-*',
[0119] b11, b12 and b13 can each independently be 1, 2 or 3,
[0120] R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0121] R 11 To R 13 Optionally, via a single bond, -C(Q 4 )(Q 5 )-、-Si(Q 4 )(Q 5 )-、-O-、-S-、-N(Q 4 )-、-B(Q 4 )-、-C(=O)-、-S(=O) 2 -、-S(=O)(Q 4 )(Q 5 )-or-P(=O)(Q 4 )- is connected to an adjacent group to form an unsubstituted or substituted C 5 -C 30 Carbocyclic or unsubstituted or substituted C 1 -C30 Heterocyclic group,
[0122] a11 may be an integer selected from 0 to 10,
[0123] a12 and a13 can each independently be 0, 1, 2 or 3,
[0124] Substituted C 5 -C 30 Carbocyclic, substituted C 1 -C 30 Heterocyclic, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from:
[0125] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0126] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, 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 );
[0127] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group and terphenyl group;
[0128] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl and terphenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl, terphenyl, -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 );as well as
[0129] -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 ),
[0130] Where Q 1 To Q 5 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Alkyl substituted C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,
[0131] * 1 ,* 2 and* 3 Each is a binding site with the central metal M of Formula 1, and
[0132] * and *' each indicate a binding site with an adjacent atom.
[0133] In one embodiment, A in Formula 3 11It can be selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, furanyl, thienyl, thirol, indenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzothirol, dibenzothirol, indolyl, carbazolyl, indenopyridinyl, indolopyridinyl, benzofuranopyridinyl, benzothienopyridinyl, benzothiarrolopyridinyl, indenopyrimidinyl, indolopyrimidinyl, benzofuranopyrimidinyl, benzothienopyrimidinyl yl, benzothiazolyl, benzopyrazolyl, benzoimidazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazopyrimidinyl, imidazopyrazinyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, and benzothiadiazolyl.
[0134] In one or more embodiments, A 11 The group may be selected from a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a 1,2-triphenylenyl group, an indenyl group, and a fluorenyl group, but the embodiments of the present disclosure are not limited thereto.
[0135] In one embodiment, each L in Formula 3 1 and L 2 It may be a single bond, but the embodiments of the present disclosure are not limited thereto.
[0136] In one embodiment, (i) X 11 Can be C, X 12 Can be C, X 13 Can be C, and X 14 Can be C; (ii) X 11 Can be N, X 12 Can be C, X 13 Can be C, and X 14 Can be C; (iii) X 11 Can be C, X 12 Can be N, X 13 Can be C, and X 14 Can be C; (iv) X 11 Can be C, X 12 Can be C, X 13 Can be N, and X 14 Can be C; (v) X 11 Can be C, X 12 Can be C, X 13 Can be C, and X 14 Can be N; (vi) X 11 Can be N, X 12 Can be N, X13 Can be C, and X 14 Can be C; (vii) X 11 Can be N, X 12 Can be C, X 13 Can be N, and X 14 Can be C; (viii) X 11 Can be N, X 12 Can be C, X 13 Can be C, and X 14 Can be N; (ix) X 11 Can be C, X 12 Can be N, X 13 Can be N, and X 14 Can be C; (x)X 11 Can be C, X 12 Can be N, X 13 Can be C, and X 14 Can be N; (xi) X 11 Can be C, X 12 Can be C, X 13 Can be N, and X 14 Can be N; (xii) X 11 Can be N, X 12 Can be N, X 13 Can be N, and X 14 Can be C; (xiii) X 11 Can be N, X 12 Can be N, X 13 Can be C, and X 14 Can be N; (xiv) X 11 Can be N, X 12 Can be C, X 13 Can be N, and X 14 Can be N; or (xv) X 11 Can be N, X 12 Can be N, X 13 Can be N, and X 14 Can be N.
[0137] In one embodiment, Y in Formula 3 11 Can be C.
[0138] In one embodiment, T 11 , T 12 and T 13 may each independently be a single bond.
[0139] In one embodiment, R 11 , R 12 , R 13 , R 14 , R 15, R 16 and R 17 Can be independently selected from:
[0140] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0141] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, and terphenyl;
[0142] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, silolyl , imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzothioxyl, 1-dibenzo-1-pyrrolyl, ...
[0143] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl , benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, dinaphthofuranyl , dinaphthothienyl, dinaphthothioyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl: deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiophene oxazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, naphthobenzothioxyl, naphthobenzothioxyl, dibenzocarbazolyl oxazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolepyrrolyl, indenocarbazolyl, indolecarbazolyl, -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 );as well as
[0144] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),
[0145] Where Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 Alkyl, selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C6 -C 60 Aryl, and a group selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 However, the embodiments of the present disclosure are not limited thereto.
[0146] In one embodiment, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 Can be independently selected from:
[0147] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and
[0148] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, and terphenyl.
[0149] In one embodiment, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 Can be independently selected from:
[0150] hydrogen, deuterium, -F, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl; and
[0151] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, each of which is substituted with at least one selected from the group consisting of deuterium, -F and cyano, but the embodiments of the present disclosure are not limited thereto.
[0152] In one embodiment, selected from R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17At least one of -F, cyano, and C substituted by at least one selected from -F and cyano 1 -C 20 alkyl.
[0153] For example, R 11 , R 12 and R 13 At least one of -F, cyano, and C substituted by at least one selected from -F and cyano 1 -C 20 alkyl.
[0154] For example, R 13 can be selected from -F, cyano, and C substituted by at least one of -F and cyano 1 -C 20 alkyl.
[0155] In one embodiment, Formula 3 is represented by one of Formula 3-1 and Formula 3-2:
[0156]
[0157] In formula 3-1 and formula 3-2,
[0158] A 11 , L 1 , L 2 , c1, c2, Y 11 , T 11 , T 12 , T 13 , b11, b12, b13, R 11 , R 14 , R 15 , R 16 , R 17 and a11 is the same as described above,
[0159] R 12a , R 12b , R 12c , R 12d , R 12e , R 12f and R 12g Combined with R 12 Same as described, and
[0160] R 13a , R 13b , R 13c , R 13d , R 13e , R 13f and R 13g Combined with R 13 Same as described.
[0161] In one embodiment, the organometallic compound represented by Formula 1 may be selected from compounds BD1 to BD48:
[0162]
[0163]
[0164] In the organometallic compound, since Ir or the like is included as M, the ligand L having a wide energy difference in the organometallic compound can be a and L b Provides relatively high metal to ligand charge transfer (MLCT) and concurrently (e.g., simultaneously) provides high spin-orbit coupling (SOC) effects (up to 5000 cm -1 ), so the intersystem crossing rate between singlet and triplet states (for example, in an organometallic compound) can be increased. Accordingly, the organometallic compound can have a maximum emission wavelength (λ) of about 390 nm to about 500 nm. max ) emits phosphorescence with high efficiency.
[0165] In organometallic compounds, because the tridentate ligand L a The central ring in the structure is directly connected to the adjacent ring, so the vibration in the excited state is suppressed (for example, the vibration of the organic metal compound in the excited state can be reduced), and thus, a high quantum yield (QY) can be obtained.
[0166] The organometallic compound includes a 5-membered heterocyclic ring (containing two or more nitrogen atoms) as a tridentate ligand L a Accordingly, compared with a ligand having a 6-membered heterocyclic ring (e.g., pyridine), due to the strong bonding force between the metal and the carbene, the center-metal triplet state (3MC state) is improved (e.g., the 3MC state of the organometallic compound is more positively favorable), and thus, the structural stability of the organometallic compound can be obtained.
[0167] The organometallic compound includes a tridentate ligand L a Accordingly, the bonding force between the ligand and the metal is increased compared to the case where a bidentate ligand is included, and thus, high structural stability of the organometallic compound is obtained.
[0168] A person of ordinary skill in the art may recognize a method for synthesizing the organometallic compound represented by Formula 1 by referring to the examples provided below.
[0169] As used herein, the expression “(the organic layer) includes at least one organic metal compound” may include the case where “(the organic layer) includes the same organic metal compound represented by Formula 1” and the case where “(the organic layer) includes two or more different organic metal compounds represented by Formula 1”.
[0170] For example, the organic layer may be an organometallic compound and may include only Compound 1. In this regard, Compound 1 may be present in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include Compound 1 and Compound 2 as organometallic compounds. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may both be present in the emission layer), or in different layers (for example, Compound 1 may be present in the emission layer and Compound 2 may be present in the electron transport layer).
[0171] The organic layer may include at least one of: i) a hole transport region located 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, and an electron blocking layer, and ii) an electron transport region located 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 may include at least one organic metal compound represented by Formula 1.
[0172] In one embodiment, the emitting layer is a first color light emitting layer,
[0173] The organic light emitting device further includes between the first electrode and the second electrode i) at least one second emission layer emitting second color light or ii) at least one second emission layer emitting second color light and at least one third emission layer emitting third color light,
[0174] The maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light may be the same as or different from each other, and
[0175] The first color light and the second color light may be emitted in the form of mixed light, or the first color light, the second color light, and the third color light may be emitted in the form of mixed light.
[0176] The emission layer may further include a host compound, and the organic metal compound included in the emission layer is a dopant, and an amount of the host compound included in the emission layer is greater than an amount of the organic metal compound included in the emission layer.
[0177] In this regard, the host compound may include a second compound and a third compound, wherein the organic metal compound, the second compound and the third compound are different from each other, the second compound and the third compound form an excited complex, and the organic metal compound may not form an excited complex with at least one of the second compound and the third compound.
[0178] An excited complex is effectively formed between the second compound and the third compound, but an excited complex is not formed between the organometallic compound and at least one of the second compound and the third compound. For example, the organometallic compound and at least one of the second compound and the third compound may be selected so that the organometallic compound does not form an excited complex with at least one of the second compound and the third compound. Accordingly, the stable host energy (the energy of at least one of the second compound and the third compound) may be effectively transferred to the dopant (organometallic compound), thereby improving the efficiency of the organic light-emitting device. When an excited complex is formed between the organometallic compound and at least one of the second compound and the third compound, the excited complex formation causes the emission wavelength of the organometallic compound to shift to a longer wavelength. Therefore, the target emission wavelength may not be obtained from the organometallic compound, and thus, the efficiency of the organic light-emitting device within the target wavelength range may be reduced.
[0179] In one embodiment, the second compound may be represented by Formula 4-1; and
[0180] The third compound can be represented by Formula 4-2:
[0181] Formula 4-1
[0182]
[0183] Formula 4-2
[0184]
[0185] In formula 4-1 and formula 4-2,
[0186] X 21 Can be selected from C(R 21 ) and N;X 22 Can be selected from C(R 22 ) and N;X 23 Can be selected from C(R 23 ) and N;X 24 Can be selected from C(R 24 ) and N;X 25 Can be selected from C(R 25 ) and N;X 26 Can be selected from C(R 26 ) and N; and X 21 To X 26At least one of may be N,
[0187] R 21 To R 26 Can be independently selected from *-(L 21 ) a21 -(R 27 ) b27 groups, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2)、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), and R 21 To R 26 At least one of them may be composed of *-(L 21 ) a21 -(R 27 ) b27 The group represented;
[0188] L 21 Can be selected from unsubstituted or substituted C 5 -C 60 Carbocyclic and unsubstituted or substituted C 1 -C 60 Heterocyclic group,
[0189] a21 may be an integer selected from 0 to 6,
[0190] R 27 Can be selected from substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 );
[0191] b27 may be an integer selected from 1 to 10,
[0192] X 31 Can be selected from single bond, O, S, B(R 33 )、N(R 33 )、C(R 33 )(R 34 ) and Si(R 33 )(R 34 );X 32 Can be selected from single bond, O, S, B(R 35 )、N(R 35 )、C(R 35 )(R 36 ) and Si(R 35 )(R 36 ); and X 31 and X 32 Not single key at the same time,
[0193] Ring A 31 and Ring A 32 Can be independently selected from C 5 -C 60 Carbocyclic and C 1 -C 60 Heterocyclic group,
[0194] R 31To R 36 Can be independently selected from *-(L 31 ) a31 -(R 37 ) b37 groups, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1)、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), and R 31 To R 36 At least one of them may be composed of *-(L 31 ) a31 -(R 37 ) b37 The group represented;
[0195] b31 and b32 may each independently be an integer selected from 1 to 10;
[0196] L 31 Can be selected from unsubstituted or substituted C 5 -C 60 Carbocyclic and unsubstituted or substituted C 1 -C 60 Heterocyclic group,
[0197] a31 may be an integer selected from 0 to 6,
[0198] R 37 Can be selected from substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 );
[0199] b37 may be an integer selected from 1 to 10,
[0200] Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 Alkyl, selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 6 -C 60 Aryl, and a group selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 heteroaryl; and
[0201] *Indicates the binding site with the neighboring atoms.
[0202] For example, X in Formula 4-1 21 To X 26 At least one of them may be N, and at least another one may be C[(L 21 ) a21 -(R 27 ) b27 ], but the embodiments of the present disclosure are not limited to this.
[0203] For example, in formula 4-1, X 21 Can be N, X 22 Can be C(R 22 );X 23 Can be C(R 23 ), X 24 Can be C(R 24 );X 25 Can be C(R 25 ), and X 26 Can be C(R 26 );
[0204] X 21 Can be N, X 22 Can be C(R 22 ), X 23 Can be N, X 24 Can be C(R 24 ), X 25 Can be C(R 25 ), and X 26 Can be C(R 26 );
[0205] X 21 Can be N, X 22 Can be C(R22 ), X 23 Can be C(R 23 ), X 24 Can be N, X 25 Can be C(R 25 ), and X 26 Can be C(R 26 );or
[0206] X 21 Can be N, X 22 Can be C(R 22 ), X 23 Can be N, X 24 Can be C(R 24 ), X 25 Can be N, and X 26 Can be C(R 26 ), but the embodiments of the present disclosure are not limited thereto.
[0207] For example, R in Formula 4-1 21 To R 26 Can be independently selected from: *-(L 21 ) a21 -(R 27 ) b27 The groups represented by hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0208] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, and terphenyl;
[0209] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, silolyl , imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzothioxyl, 1-dibenzo-1-pyrrolyl, ...
[0210] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl , benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, dinaphthofuranyl , dinaphthothienyl, dinaphthothioyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl: deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiophene oxazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, naphthobenzothioxyl, naphthobenzothioxyl, dibenzocarbazolyl oxazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolepyrrolyl, indenocarbazolyl, indolecarbazolyl, -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 );as well as
[0211] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),
[0212] Where Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 Alkyl, selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C6 -C 60 Aryl, and a group selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 However, the embodiments of the present disclosure are not limited thereto.
[0213] In one or more embodiments, R in Formula 4-1 21 To R 26 Can be independently selected from: *-(L 21 ) a21 -(R 27 ) b27 The groups represented by hydrogen, deuterium, -F, -Cl, -Br, -I, cyano and C 1 -C 20 alkyl;
[0214] C substituted by at least one selected from deuterium, -F, -Cl, -Br, -I and cyano 1 -C 20 alkyl;
[0215] A group represented by Formula 5-1 to Formula 5-139; and
[0216] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), but the embodiments of the present disclosure are not limited thereto:
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223] In equations 5-1 to 5-139,
[0224] X 51 Can be selected from O, S, N (R 51 ) and C(R 51 )(R 60 ),
[0225] X 52 Can be N or C(R 52 ), X 53 Can be N or C(R 53 ), X 54 Can be N or C(R 54 ), X 55 Can be N or C(R 55 ), X 56 Can be N or C(R 56 ), X 57 Can be N or C(R 57 ), X 58 Can be N or C(R 58 ), X 59 Can be N or C(R 59 ),
[0226] R 51 To R 60 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, thienyl, furanyl, thiole, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, benzothiole, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzothiole, -C(Q 31 )(Q 32 )(Q 33 )、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q32 )、-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 ),
[0227] Q 1 To Q 3 and Q 31 To Q 33 Can be independently selected from C 1 -C 60 Alkyl, phenyl, biphenyl and terphenyl,
[0228] b51 can be selected from 1, 2, 3, 4 and 5,
[0229] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,
[0230] b53 can be selected from 1, 2, 3, 4, 5, 6, 7, 8 and 9,
[0231] b54 can be selected from 1, 2, 3 and 4,
[0232] b55 can be selected from 1, 2 and 3,
[0233] b56 can be selected from 1 and 2,
[0234] b57 can be selected from 1, 2, 3, 4, 5 and 6, and
[0235] *Indicates the binding site with the neighboring atoms.
[0236] For example, L in formula 4-1 21 can be selected from phenyl, naphthyl, phenaltenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, 1,2-triphenylenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and
[0237] phenyl, naphthyl, phenaltenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, 1,2-triphenylphenanthrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1,2-benzophenanthryl, fluoranthenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl, but the embodiments of the present disclosure are not limited thereto.
[0238] For example, a21 in Formula 4-1 may be an integer selected from 0 to 2, but the embodiments of the present disclosure are not limited thereto.
[0239] For example, R in Formula 4-1 27 Can be selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0240] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, and terphenyl;
[0241] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, silolyl , imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzothioxyl, 1-dibenzo-1-pyrrolyl, ...
[0242] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl , benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, dinaphthofuranyl , dinaphthothienyl, dinaphthothioyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl: deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiophene oxazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, naphthobenzothioxyl, naphthobenzothioxyl, dibenzocarbazolyl oxazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolepyrrolyl, indenocarbazolyl, indolecarbazolyl, -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 );as well as
[0243] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),
[0244] Where Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 Alkyl, selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C6 -C 60 Aryl, and a group selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 However, the embodiments of the present disclosure are not limited thereto.
[0245] In one or more embodiments, R in Formula 4-1 27 Can be selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano and C 1 -C 20 alkyl;
[0246] C substituted by at least one selected from deuterium, -F, -Cl, -Br, -I and cyano 1 -C 20 alkyl;
[0247] A group represented by Formula 5-1 to Formula 5-139; and
[0248] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),
[0249] Where Q 1 To Q 3 Can be independently selected from C 1 -C 60 An alkyl group, a phenyl group, a biphenyl group, and a terphenyl group, but the embodiments of the present disclosure are not limited thereto.
[0250] In one embodiment, R in Formula 4-1 27 Can be selected from: -C(Q 1 )(Q 2 )(Q3 ) and -Si(Q 1 )(Q 2 )(Q 3 );as well as
[0251] A group represented by Formula 7-1 and a group represented by Formula 7-2, but the embodiments of the present disclosure are not limited thereto:
[0252]
[0253] In equation 7-1 and equation 7-2,
[0254] Y 71 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 31 )(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ),
[0255] Ring A 71 Can be selected from C 5 -C 60 Carbocyclic and C 1 -C 60 Heterocyclic group,
[0256] X 71 Can be selected from C(R 71 ) and N,
[0257] R 71 and R 72can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -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)(Q31 )(Q 32 ),
[0258] R 71 and R 72 may be optionally linked to form unsubstituted or substituted C 5 -C 30 Carbocyclic or unsubstituted or substituted C 1 -C 30 Heterocyclic group,
[0259] b72 may be an integer selected from 1 to 10,
[0260] Q 1 To Q 3 and Q 31 To Q 33 Can be independently selected from C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 6 -C 60 Aryl, and a group selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 heteroaryl, and
[0261] *Indicates the binding site with the neighboring atoms.
[0262] For example, ring A in formula 7-1 and formula 7-2 71 Combined with A 11 Same as described.
[0263] For example, X in Formula 4-2 31 Can be selected from single bond, O, S, B(R 33 )、N(R 33 )、C(R 33 )(R 34 ) and Si(R 33 )(R 34),and
[0264] X 32 Can be selected from O, S, B (R 35 )、N(R 35 )、C(R 35 )(R 36 ) and Si(R 35 )(R 36 ), but the embodiments of the present disclosure are not limited thereto.
[0265] In one or more embodiments, X in Formula 4-2 31 Can be selected from single bond, O, S, N(R 33 )、C(R 33 )(R 34 ) and Si(R 33 )(R 34 ),and
[0266] X 32 Can be selected from O, S, N (R 35 )、C(R 35 )(R 36 ) and Si(R 35 )(R 36 ), but the embodiments of the present disclosure are not limited thereto.
[0267] For example, ring A in formula 4-2 31 and Ring A 32 The cyclohexyl, cyclohexenyl, cyclohexadienyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, silyl, oxasilyl, thiasilyl, azasilyl, dihydrodisilyl, dioxinyl, oxathiinyl, oxazinyl, dithiine, thiazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, indolofluorenyl, indolocarbazolyl, indolodibenzofuranyl, indolodibenzothiophene In some embodiments, the present invention comprises a benzofuranyl group, a benzofuranyl group, a benzofuranyl group, a benzofuranyl group, a benzofuranyl group, a benzofuranyl group, a benzofuranyl group, a benzofuranyl group, a benzothiophene group, a benzothiophenefluorenyl group, a benzofuranyl group, a benzofuranyl group, a benzothiophenecarbazolyl group, a benzothiophenedibenzofuranyl group, a benzothiophenedibenzothiophene group, a dibenzosilyl group, a dibenzooxasilyl group, a dibenzothiasilyl group, a dibenzoazasilyl group, a dibenzodihydrodisilazyl group, a dibenzodioxinyl group, a dibenzoxathiacinyl group, a dibenzodithiacinyl group, and a dibenzothiazinyl group, but the embodiments of the present disclosure are not limited thereto.
[0268] For example, R in Formula 4-231 To R 36 Can be independently selected from: *-(L 31 ) a31 -(R 37 ) b37 The groups represented by hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0269] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl and terphenyl,
[0270] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, silolyl , imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzothioxyl, 1-dibenzo-1-pyrrolyl, ...
[0271] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl , benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, dinaphthofuranyl , dinaphthothienyl, dinaphthothioyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl: deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiophene oxazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, naphthobenzothioxyl, naphthobenzothioxyl, dibenzocarbazolyl oxazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolepyrrolyl, indenocarbazolyl, indolecarbazolyl, -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 );
[0272] Groups represented by Formula 8-1 and Formula 8-2; and
[0273] -C(Q 1 )(Q 2)(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), but the embodiments of the present disclosure are not limited thereto:
[0274]
[0275] In equation 8-1 and equation 8-2,
[0276] X 81 Selected from N, C (R 83 ) and Si(R 83 ),
[0277] X 82 Selected from single bond, O, S, B(R 84 )、N(R 84 )、C(R 84 )(R 85 ) and Si(R 84 )(R 85 ),
[0278] X 83 Selected from single bond, O, S, B(R 86 )、N(R 86 )、C(R 86 )(R 87 ) and Si(R 86 )(R 87 ),
[0279] X 82 and X 83 Not single key at the same time,
[0280] Ring A 81 and Ring A 82 Can be independently selected from C 5 -C 60 Carbocyclic and C 1 -C60 Heterocyclic group,
[0281] R 81 To R 87 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thiophene oxazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenanthrolinyl, oxazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothioxyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioxyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioxyl, dibenzocarbazolyl, naphthobenzothioxyl, naphthobenzothioxyl, dibenzocarbazolyl oxazolyl, dinaphthofuranyl, dinaphthothienyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothioyl, indenopyrrolyl, indolepyrrolyl, indenocarbazolyl, indolecarbazolyl, -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 ),
[0282] b81 and b82 may each independently be an integer selected from 1 to 10,
[0283] * indicates the binding site with the neighboring atoms, and
[0284] Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 Alkyl, selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 6 -C 60 Aryl, and a group selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 Heteroaryl.
[0285] In one or more embodiments, R in Formula 4-2 31 To R 36 Can be independently selected from: *-(L 31 ) a31 -(R 37 ) b37 The groups represented by hydrogen, deuterium, -F, -Cl, -Br, -I, cyano and C 1 -C 20 alkyl;
[0286] C substituted by at least one selected from the following 1 -C 20 Alkyl: deuterium, -F, -Cl, -Br, -I and cyano;
[0287] A group represented by Formula 5-1 to Formula 5-139;
[0288] Groups represented by Formula 8-1 and Formula 8-2; and
[0289] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),
[0290] Where Q 1 To Q 3 and Q 31 To Q 33 Can be independently selected from C 1 -C 60 An alkyl group, a phenyl group, a biphenyl group, and a terphenyl group, but the embodiments of the present disclosure are not limited thereto.
[0291] For example, L in Formula 4-2 31can be selected from: phenyl, naphthyl, phenaltenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, 1,2-triphenylenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and
[0292] phenyl, naphthyl, phenaltenyl, anthracenyl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, 1,2-triphenylphenanthrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 1,2-benzophenanthryl, fluoranthenyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl, quinazolinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, diazafluorenyl, diazacarbazolyl, diazadibenzofuranyl and diazadibenzothiophenyl, but the embodiments of the present disclosure are not limited thereto.
[0293] For example, a31 in Formula 4-2 may be an integer selected from 0 to 2.
[0294] For example, R in Formula 4-2 37 The group represented by Formula 8-1 and the group represented by Formula 8-2 can be selected.
[0295] For example, ring A in formula 8-1 and formula 8-2 81 and Ring A 82The cyclohexyl, cyclohexenyl, cyclohexadienyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, silyl, oxasilyl, thiasilyl, azasilyl, dihydrodisilyl, dioxinyl, oxathiazinyl, oxazinyl, dithiazinyl, thiazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, indolofluorenyl, indolocarbazolyl, indolodibenzofuranyl, indolodiphenyl The compounds include benzothiophene, benzofuranyl, benzothiophene-based ...
[0296] In one embodiment, the second compound may be represented by one of Formula 4-1-1 and Formula 4-1-2, but embodiments of the present disclosure are not limited thereto:
[0297]
[0298] In formula 4-1-1 and formula 4-1-2,
[0299] X 21 Can be selected from C(R 21 ) and N;X 23 Can be selected from C(R 23 ) and N;X 24 Can be selected from C(R 24 ) and N;X 25 Can be selected from C(R 25 ) and N; and X 26 Can be selected from C(R 26 ) and N,
[0300] X in formula 4-1-1 21 and X 23 To X 26 At least one of may be N,
[0301] X in formula 4-1-2 21 and X 23 To X 25 At least one of may be N,
[0302] R 21 and R 23 To R26 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2) and -P(=S)(Q 1 )(Q 2 ),
[0303] L 21a and L 21b can be independently selected from unsubstituted or substituted C 5 -C 60 Carbocyclic and unsubstituted or substituted C 1 -C 60 Heterocyclic group,
[0304] a21a and a21b may each independently be an integer selected from 0 to 6,
[0305] R 27a and R 27b Can be independently selected from -C(Q 1 )(Q 2 )(Q 3 ) and -Si(Q 1 )(Q 2 )(Q 3 );as well as
[0306] The group represented by formula 7-1 and the group represented by formula 7-2:
[0307]
[0308]
[0309] In equation 7-1 and equation 7-2,
[0310] Y 71 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 31)(Q 32 )(Q 33 ) and -Si(Q 31 )(Q 32 )(Q 33 ),
[0311] Ring A 71 Can be selected from C 5 -C 60 Carbocyclic and C 1 -C 60 Heterocyclic group,
[0312] X 71 Can be selected from C(R 71 ) and N,
[0313] R 71 and R 72 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 alkylheteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 31 )(Q32 )(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 ),
[0314] R 71 and R 72 may be optionally linked to form unsubstituted or substituted C 5 -C 30 Carbocyclic or unsubstituted or substituted C 1 -C 30 Heterocyclic group,
[0315] b72 may be an integer selected from 1 to 10,
[0316] b27a and b27b may each independently be an integer selected from 1 to 10,
[0317] Q 1 To Q 3 and Q 31 To Q 33 Can be independently selected from C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 6 -C 60Aryl, and a group selected from deuterium, -F, cyano, C 1 -C 10 At least one of alkyl, phenyl and biphenyl substituted C 1 -C 60 heteroaryl, and
[0318] *Indicates the binding site with the neighboring atoms.
[0319] In one embodiment, the second compound may be selected from compounds of Group II, and
[0320] The third compound may be selected from compounds of Group III, but embodiments of the present disclosure are not limited thereto.
[0321] Group II
[0322]
[0323]
[0324]
[0325] Group III
[0326]
[0327] The decay time of delayed fluorescence in the time-resolved electroluminescence (TREL) spectrum of the organic light-emitting device may be 50 nanoseconds (ns) or more, for example, greater than or equal to 50 ns and less than or equal to 10 microseconds (μs). In one embodiment, the decay time of delayed fluorescence in the TREL spectrum of the organic light-emitting device may be greater than or equal to 1.4 μs and less than or equal to 4 μs or greater than or equal to 1.5 μs and less than or equal to 3 μs. When the decay time of delayed fluorescence of the organic light-emitting device is within these ranges, the time that the organic metal compound remains in an excited state is relatively reduced, so that the organic light-emitting device can have high luminous efficiency and a long life.
[0328] In one embodiment, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound and the LUMO energy level of the second compound may be greater than or equal to about 0.1 eV and less than or equal to about 1.0 eV, the absolute value of the difference between the LUMO energy level of the organometallic compound and the LUMO energy level of the third compound may be greater than or equal to about 0.1 eV and less than or equal to about 1.0 eV, the absolute value of the difference between the highest occupied molecular orbital (HOMO) energy level of the organometallic compound and the HOMO energy level of the second compound may be 1.25 eV or less (e.g., less than or equal to about 1.25 eV and greater than or equal to about 0.2 eV), or the absolute value of the difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the third compound may be 1.25 eV or less (e.g., less than or equal to about 1.25 eV and greater than or equal to about 0.2 eV).
[0329] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions as described above, holes and electrons injected into the emission layer may be balanced (eg, may be suitable for the operation of the organic light-emitting device).
[0330] As used herein, the term "organic layer" refers to a single layer and / or multiple layers located between a first electrode and a second electrode of an organic light-emitting device. The materials included in the "organic layer" are not limited to organic materials. For example, the organic layer may include an inorganic material.
[0331] Figure 1 Description
[0332] Figure 1 2 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment of the present invention. The organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .
[0333] In the following, we will combine Figure 1 A structure of an organic light-emitting device 10 and a method of manufacturing the organic light-emitting device 10 according to an embodiment are described.
[0334] First electrode 110
[0335] exist Figure 1 In the embodiment, the substrate may be additionally located below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate, each of which has excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.
[0336] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.
[0337] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and 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 used to form 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.
[0338] 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.
[0339] Organic layer 150
[0340] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emission layer.
[0341] The organic layer 150 may further include at least one of a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .
[0342] Hole transport region in the organic layer 150
[0343] The hole transport region may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including a plurality of different materials.
[0344] The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.
[0345] For example, the hole transport zone may have a single-layer structure including a single layer containing a plurality of different materials, or a multilayer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein for each structure, the constituent layers are stacked sequentially in the order described starting from the first electrode 110, but the structure of the hole transport zone is not limited thereto.
[0346] The hole transport region may include at least one selected from the following: m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
[0347]
[0348]
[0349] Formula 201
[0350]
[0351] Formula 202
[0352]
[0353] In equation 201 and equation 202,
[0354] L 201 To L 204 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0355] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2-C 20 Alkenylene, substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0356] xa1 to xa4 may each independently be an integer selected from 0 to 3,
[0357] xa5 may be an integer selected from 1 to 10,
[0358] R 201 To R 204 and Q 201 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0359] In one embodiment, in Formula 202, R 201 and R 202 may be optionally linked via a single bond, a dimethyl-methylene or a diphenyl-methylene, and R 203 and R 204The attachment may optionally be via a single bond, a dimethyl-methylene or a diphenyl-methylene.
[0360] In one embodiment, in Formulas 201 and 202,
[0361] L 201 To L 205 Can be independently selected from:
[0362] Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, tetraphenylene, pyrenylene, perylene, pyren ... pentaphenylene, hexaphenylene, pentaphenylene, rubidinylene, coronenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridylene; and
[0363] each substituted with at least one selected from the following: phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, tetraphenylene, pyrenylene, perylene, pentaphenanylene, hexaphenylene , pentaphenylene, rubidinyl, coronene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene and pyridylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10Alkyl substituted phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, tetraphenyl, pyrenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, rubenyl, coronenyl, ovophene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridinyl, -Si(Q) 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),
[0364] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0365] In one or more embodiments, xa1 to xa4 may each independently be 0, 1 or 2.
[0366] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0367] In one or more embodiments, R 201 To R 204 and Q 201 each independently selected from the group consisting of phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, naphthacene, pyrenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, rubinyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl; and
[0368] phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, naphthacene, pyrenyl, peryl, pentaphenanthrenyl, hexacene phenyl, pentacene, rubinyl, coryl, ovale, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl substituted phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, tetraphenyl, pyrenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, rubenyl, coronenyl, ovophene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridinyl, -Si(Q) 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),
[0369] Where Q 31 To Q 33 Same as described above.
[0370] In one or more embodiments, R selected from Formula 201 201 To R 203 At least one of can be independently selected from:
[0371] fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and
[0372] Fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,
[0373] However, the embodiments of the present disclosure are not limited thereto.
[0374] In one or more embodiments, in Formula 202, i) R 201 and R 202 can be connected to each other via a single bond, and / or ii) R 203 and R 204 Can be connected to each other via a single bond.
[0375] In one or more embodiments, R in Formula 202 201 To R 204 Can be independently selected from:
[0376] carbazolyl; and
[0377] A carbazolyl group substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,
[0378] However, the embodiments of the present disclosure are not limited thereto.
[0379] The compound represented by Formula 201 can be represented by the following Formula 201-1:
[0380] Formula 201-1
[0381]
[0382] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201-2, but embodiments of the present disclosure are not limited thereto:
[0383] Formula 201-2
[0384]
[0385] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201-2(1), but the embodiments of the present disclosure are not limited thereto:
[0386] Formula 201-2(1)
[0387]
[0388] The compound represented by Formula 201 can be represented by Formula 201A:
[0389] Formula 201A
[0390]
[0391] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but embodiments of the present disclosure are not limited thereto:
[0392] Formula 201A(1)
[0393]
[0394] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but embodiments of the present disclosure are not limited thereto:
[0395] Formula 201A-1
[0396]
[0397] In one embodiment, the compound represented by Formula 202 may be represented by the following Formula 202-1:
[0398] Formula 202-1
[0399]
[0400] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202-1(1):
[0401] Formula 202-1(1)
[0402]
[0403] The compound represented by Formula 202 can be represented by Formula 202A:
[0404] Formula 202A
[0405]
[0406] In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:
[0407] Formula 202A-1
[0408]
[0409] In equation 201-1, equation 201-2, equation 201-2(1), equation 201A, equation 201A(1), equation 201A-1, equation 202-1, equation 202-1(1), equation 202A, and equation 202A-1,
[0410] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 Same as described above,
[0411] L 205 may be selected from phenylene and fluorene,
[0412] X 211 Can be selected from O, S and N (R 211 ),
[0413] X 212 Can be selected from O, S and N (R 212 ),
[0414] R 211 and R 212 Can be combined with R 203 The same as defined, and
[0415] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, tetracenyl, pyrenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridinyl.
[0416] The hole transport region may include at least one compound selected from the following Compound HT1 to Compound HT48, but the embodiments of the present disclosure are not limited thereto:
[0417]
[0418]
[0419]
[0420]
[0421]
[0422] 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 of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about 1000 Å. to about For example, about to about and the thickness of the hole transport layer may be in the range of about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, appropriate or satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.
[0423] The emission assisting layer may increase light emission efficiency by compensating for the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer may block or reduce the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer may include materials as described above.
[0424] p-dopant
[0425] In addition to the materials described above, the hole transport region may further include a charge generation material for improving conduction properties (eg, conductive properties). The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.
[0426] The charge generating material may be, for example, a p-dopant.
[0427] In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.
[0428] The p-dopant may include at least one selected from the group consisting of a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiments of the present disclosure are not limited thereto.
[0429] For example, the p-dopant may include at least one selected from the following: a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0430] Metal oxides, such as tungsten oxide and molybdenum oxide;
[0431] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and
[0432] The compound represented by formula 221,
[0433] However, the embodiments of the present disclosure are not limited thereto:
[0434]
[0435] Formula 221
[0436]
[0437] In formula 221,
[0438] R 221 To R 223 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and is selected from R 221 To R 223 At least one of the following may have at least one substituent selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted by -Cl 1 -C 20 Alkyl, C substituted by -Br 1 -C 20 Alkyl and C substituted by -I 1 -C 20 alkyl.
[0439] Emission layer in the organic layer 150
[0440] 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 the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, 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.
[0441] The emission layer may include a host and a dopant. The host may be understood by referring to the description of the second compound and the third compound, and the dopant may be understood by referring to the description of the organic metal compound represented by Formula 1 for the description of the dopant.
[0442] The amount of the dopant in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on about 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0443] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within this range, excellent light emission characteristics can be obtained without significantly increasing the driving voltage.
[0444] Subject in the emission layer
[0445] In one or more embodiments, the host may include a compound represented by Formula 301 below.
[0446] Formula 301
[0447] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0448] In formula 301,
[0449] Ar 301 Can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0450] xb11 can be 1, 2 or 3,
[0451] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0452] xb1 may be an integer selected from 0 to 5,
[0453] R 301 can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic 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 ),
[0454] xb21 may be an integer selected from 1 to 5, and
[0455] Q 301 To Q 303 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0456] In one embodiment, Ar in Formula 301 301 You can choose from:
[0457] naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and
[0458] naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, naphthacene, pyrenyl, peryl, pentaphenanthracene, indenoanthryl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0459] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0460] When xb11 in Formula 301 is 2 or greater, two or more Ar 301 Can be connected via one-touch.
[0461] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:
[0462] Formula 301-1
[0463]
[0464] Formula 301-2
[0465]
[0466] In Formula 301-1 and Formula 301-2,
[0467] A 301 To A 304The phenyl group may be independently selected from phenyl, naphthyl, phenanthryl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, pyridyl, pyrimidinyl, indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthothienyl, benzonaphthothienyl and dinaphthothienyl,
[0468] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0469] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ),
[0470] xb22 and xb23 can each independently be 0, 1 or 2,
[0471] L 301 、xb1、R 301 and Q 31 To Q 33 Same as described above,
[0472] L 302 To L 304 Can be combined with L independently 301 Same as described,
[0473] xb2 to xb4 may each independently be the same as described in conjunction with xb1, and
[0474] R 302 To R 304Can be combined with R 301 Same as described.
[0475] For example, L in Formula 301, Formula 301-1, and Formula 301-2 301 To L 304 Can be independently selected from:
[0476] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene oxazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0477] each substituted with at least one selected from the following: phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, 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, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene and azacarbazolylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazinyl, hydrazone, C 1 -C 20 Alkyl, C 1 -C20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyridine oxazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, 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 ),
[0478] Where Q 31 To Q 33 Same as described above.
[0479] In one embodiment, R in Formula 301, Formula 301-1, and Formula 301-2 301 To R 304 Can be independently selected from:
[0480] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazole yl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0481] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl oxazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyridine oxazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, 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 ),and
[0482] Q 31 To Q 33 Same as described above.
[0483] In one embodiment, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.
[0484] In one or more embodiments, the host may include at least one selected from the group consisting of 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), and compounds H1 to H124, but embodiments of the present disclosure are not limited thereto:
[0485]
[0486]
[0487]
[0488]
[0489]
[0490]
[0491]
[0492] In one embodiment, the host may include at least one of a silicon-containing compound (eg, BCPDS, etc.) and a phosphine oxide-containing compound (eg, POPCPA, etc.).
[0493] The host may include only one compound or may include two or more compounds that are different from each other (eg, the host includes BCPDS and POPCPA). In one or more embodiments, the host may instead have various other suitable variations.
[0494] The phosphorescent dopant included in the emission layer in the organic layer 150
[0495] The phosphorescent dopant may include an organic metal complex represented by the following Formula 401:
[0496] Formula 401
[0497] M(L 401 ) xc1 (L 402 ) xc2 .
[0498] In formula 401,
[0499] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),
[0500] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 may be the same or different from each other,
[0501] L 402 may be an organic ligand, and xc2 may be an integer selected from 0 to 4, wherein when xc2 may be 2 or greater, two or more L 402may be the same or different from each other,
[0502] Formula 402
[0503]
[0504] In formula 402, X 401 To X 404 may each independently be nitrogen or carbon,
[0505] X 401 and X 403 can be connected via a single bond or a double bond, and X 402 and X 404 Can be connected via single or double bonds,
[0506] A 401 and A 402 Can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0507] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C(Q 411 )-*', where Q 411 and Q 412 Can be hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,
[0508] X 406 Can be a single bond, O or S,
[0509] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 1 -C 20 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ) and Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 6 -C 20 Aryl and C 1 -C 20 Heteroaryl,
[0510] xc11 and xc12 may each independently be an integer selected from 0 to 3,
[0511] * and *' in Formula 402 each indicate a binding site with M in Formula 401.
[0512] In one embodiment, A in Formula 402 401 and A 402The benzofuranyl, benzothiophenyl, benzo[c]thiophenyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, and dibenzothiophenyl may be independently selected from the group consisting of phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzo[c]thiophenyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, and dibenzothiophenyl.
[0513] In one or more embodiments, in Formula 402, i) X 401 may be nitrogen and X 402 Can be carbon, or ii) X 401 and X 402 They may each be nitrogen at the same time.
[0514] In one or more embodiments, R in Formula 402 401 and R 402 Can be independently selected from:
[0515] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0516] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl;
[0517] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;
[0518] cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1-C 20 Alkyl, C 1 -C 20 alkoxy, cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and -Si(Q) 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ),
[0519] Where Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0520] In one or more embodiments, when xc1 in Formula 401 is 2 or greater, two or more L 401 Two A's 401 Optionally, the 407 Connected to each other, two A 402 Optionally, the 408 are connected to each other (see compounds PD1 to PD4 and PD7 below). 407 and X 408 can be each independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*'、*-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments of the present disclosure are not limited thereto.
[0521] L in Formula 401 402 It can be a monovalent, divalent or trivalent organic ligand. For example, L 402 It may be selected from halogen, diketone (eg, acetylacetonate), carboxylic acid (eg, picolinate), -C(=O), isonitrile, -CN, and phosphorus-containing ligand (eg, phosphine or phosphite), but the embodiments of the present disclosure are not limited thereto.
[0522] In one or more embodiments, the phosphorescent dopant may be selected from, for example, Compound PD1 to Compound PD25, but embodiments of the present disclosure are not limited thereto:
[0523]
[0524] The fluorescent dopant included in the emission layer in the organic layer 150
[0525] The fluorescent dopant may further include an aromatic amine compound or a styrylamine compound.
[0526] The fluorescent dopant may include a compound represented by Formula 501 below.
[0527] Formula 501
[0528]
[0529] In formula 501,
[0530] Ar 501 Can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0531] L 501 To L 503 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0532] xd1 to xd3 may each independently be an integer selected from 0 to 3,
[0533] R 501 and R 502 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
[0534] xd4 may be an integer selected from 1-6.
[0535] In one embodiment, Ar in Formula 501 501 You can choose from:
[0536] naphthyl, heptalenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and
[0537] naphthyl, heptalenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl and indenophenanthrenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0538] In one or more embodiments, L in Formula 501 501 To L 503 Can be independently selected from:
[0539] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenanthrenylene, perylene, pentaphenylene, hexaphenylene, pentacenylenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridylene; and
[0540] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, and pyridylene, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridinyl.
[0541] In one or more embodiments, R in Formula 501 501 and R 502 Can be independently selected from:
[0542] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and
[0543] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, and pyridyl, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl and -Si(Q) 31 )(Q 32 )(Q 33 ),
[0544] Where Q 31 To Q 33 Can be selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0545] In one or more embodiments, xd4 in Formula 501 may be 2, but embodiments of the present disclosure are not limited thereto.
[0546] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:
[0547]
[0548]
[0549]
[0550] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but embodiments of the present disclosure are not limited thereto.
[0551]
[0552] Electron transport region in the organic layer 150
[0553] The electron transport region may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including a plurality of different materials.
[0554] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.
[0555] For example, the electron transport region may have a structure of an electron transport layer / electron injection layer, a structure of a hole blocking layer / electron transport layer / electron injection layer, a structure of an electron control layer / electron transport layer / electron injection layer, or a structure of a buffer layer / electron transport layer / electron injection layer, wherein for each structure, the constituent layers are stacked in sequence from the emission layer. However, the embodiment of the structure of the electron transport region is not limited thereto.
[0556] The electron transport region may include the second compound as described above.
[0557] In an embodiment, the electron transport region may include a buffer layer, the buffer layer directly contacts the emission layer, and the buffer layer may include the second compound as described above.
[0558] In one or more embodiments, the electron transport region may include a buffer layer, an electron transport layer, and an electron injection layer stacked in this order from the emission layer, and the buffer layer may include the second compound as described above.
[0559] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one ring containing π-electron-depleted nitrogen.
[0560] As used herein, the term "π-electron-depleted nitrogen-containing ring" refers to a C-type ring having at least one *-N=*' moiety as a ring-forming portion. 1 -C 60 Heterocyclic group.
[0561] For example, the "π-electron-depleted nitrogen-containing ring" may be i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups (each having at least one *-N=*' moiety) are fused to each other, or iii) a heteropolycyclic group in which at least one 5- to 7-membered heteromonocyclic group (each having at least one *-N=*' moiety) is fused to at least one C 5 -C 60 A carbocyclyl-fused heteropolycyclic group.
[0562] Examples of rings containing π-electron-depleted nitrogen 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, benzisothiazole, benzoxazole, benzisoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.
[0563] For example, the electron transport region may include a compound represented by Formula 601:
[0564] Formula 601
[0565] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0566] In formula 601,
[0567] Ar 601 Can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0568] xe11 can be 1, 2 or 3,
[0569] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0570] xe1 may be an integer selected from 0 to 5,
[0571] R 601 Can be selected from substituted or unsubstituted C 3 -C10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic 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 ),
[0572] Q 601 To Q 603 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and
[0573] xe21 may be an integer selected from 1-5.
[0574] In one embodiment, the amount of Ar is xe11 601 and the number of R is xe21 601 At least one of may include a ring containing π-electron-depleted nitrogen.
[0575] In one embodiment, Ar in Formula 601 601 You can choose from:
[0576] Phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl oxazolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0577] phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, naphthacene, pyrenyl, peryl, pentaphenanthracenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purine quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0578] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0579] When xe11 in Formula 601 is 2 or greater, two or more Ar 601 Can be connected via one-touch.
[0580] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.
[0581] In one or more embodiments, the compound represented by Formula 601 may be represented by the following Formula 601-1:
[0582] Formula 601-1
[0583]
[0584] In formula 601-1,
[0585] 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 ), selected from X 614 To X 616 At least one of may be N,
[0586] L 611 To L 613 Can be combined with L independently 601 Same as described,
[0587] xe611 to xe613 can each independently be the same as described in conjunction with xe1,
[0588] R 611 To R 613 Can be combined with R 601 Same as described, and
[0589] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0590] In one embodiment, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Can be independently selected from:
[0591] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene oxazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0592] each substituted with at least one selected from the following: phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, 1,2-triphenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, 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, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene and azacarbazolylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazinyl, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl , pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl,
[0593] However, the embodiments of the present disclosure are not limited thereto.
[0594] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.
[0595] In one or more embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Can be independently selected from:
[0596] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyridine oxazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl;
[0597] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl oxazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0598] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0599] Where Q 601 and Q 602 Same as described above.
[0600] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36, but embodiments of the present disclosure are not limited thereto:
[0601]
[0602]
[0603]
[0604]
[0605] In one or more embodiments, the electron transport region may include at least one compound selected from the group consisting of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , 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:
[0606]
[0607]
[0608] The thickness of the buffer layer, the hole blocking layer, and the electron control layer may each be about to about For example, about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the buffer layer, the hole blocking layer, and the electron control layer may have excellent hole blocking properties or electron control properties without significantly increasing the driving voltage.
[0609] The thickness of the electron transport layer can be about to about For example, about to about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have appropriate or satisfactory electron transport characteristics without significantly increasing the driving voltage.
[0610] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the materials described above.
[0611] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from Li ions, Na ions, K ions, Rb ions and Cs ions, and the alkaline earth metal complex may include a metal ion selected from Be ions, Mg ions, Ca ions, Sr ions and Ba ions. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
[0612] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) or ET-D2.
[0613]
[0614] The electron transport region may include an electron injection layer that allows electrons to be easily provided from the second electrode 190. The electron injection layer may directly contact the second electrode 190.
[0615] The electron injection layer may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including a plurality of different materials.
[0616] 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.
[0617] 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.
[0618] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.
[0619] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0620] The alkali metal compound, alkaline earth metal compound and rare earth metal compound may be selected from oxides and halides (eg, fluorides, chlorides, bromides or iodides) of alkali metals, alkaline earth metals and rare earth metals.
[0621] The alkali metal compound can be selected from alkali metal oxides (such as Li2 O, Cs 2 O or K 2 O) 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, Li 2 O, NaF, LiI, NaI, CsI and KI, but the embodiments of the present disclosure are not limited thereto.
[0622] Alkaline earth metal compounds may be selected from BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1) and Ba x Ca 1-x O (0 < x < 1). In one embodiment, the alkaline earth metal compounds may be selected from BaO, SrO and CaO, but the embodiments of the present disclosure are not limited thereto.
[0623] Rare earth metal compounds may be selected from YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 and TbF 3 . In one embodiment, the rare earth metal compounds may be selected from YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 and TbI 3 , but the embodiments of the present disclosure are not limited thereto.
[0624] Alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes may include ions of alkali metals, alkaline earth metals and rare earth metals as described above, and ligands coordinated with metal ions of alkali metal complexes, alkaline earth metal complexes or rare earth metal complexes 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.
[0625] The electron injection layer may be composed of 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, 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 an organic material.
[0626] The thickness of the electron injection layer can be about to about For example, about to about When the thickness of the electron injection layer is within the range described above, the electron injection layer may have appropriate or satisfactory electron injection characteristics without significantly increasing the driving voltage.
[0627] Second electrode (190)
[0628] The second electrode 190 is located on the organic layer 150 having the above structure. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.
[0629] 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.
[0630] The second electrode 190 may have a single-layer structure, or a multi-layer structure including two or more layers.
[0631] Figures 2 to 4 Description
[0632] Figure 2 The organic light-emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150 and a second electrode 190 which are sequentially stacked in the following order; Figure 3 The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 sequentially stacked in the order described below; and Figure 4The organic light-emitting device 40 includes a first capping layer 210 , a first electrode 110 , an organic layer 150 , a second electrode 190 , and a second capping layer 220 .
[0633] for Figures 2 to 4 , can be combined by reference Figure 1 The description is presented to understand the first electrode 110 , the organic layer 150 , and the second electrode 190 .
[0634] In the organic layer 150 of each of the organic light-emitting devices 20 and the organic light-emitting devices 40, light generated in the emission layer can pass through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210 toward the outside, and in the organic layer 150 of each of the organic light-emitting devices 30 and the organic light-emitting devices 40, light generated in the emission layer can pass through the second electrode 190 as a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220 toward the outside.
[0635] The first capping layer 210 and the second capping layer 220 may increase external light emitting efficiency according to the principle of constructive interference.
[0636] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
[0637] At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. Carbocyclic compounds, heterocyclic compounds, and amine compounds may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine compound.
[0638] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.
[0639] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but embodiments of the present disclosure are not limited thereto:
[0640]
[0641]
[0642] The above has been combined Figures 1 to 4 The organic light emitting device according to the embodiment is described. However, the embodiments of the present disclosure are not limited thereto.
[0643] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region may be formed in a certain region by using one or more appropriate methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and / or laser induced thermal imaging.
[0644] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and approx. to about Deposition is carried out at a deposition rate of .
[0645] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to 200°C by considering the composition of the material to be included in the layer to be formed and the structure of the layer to be formed.
[0646] equipment
[0647] The organic light emitting device may be included in a variety of suitable devices.
[0648] In more detail, an example of such an apparatus may include: a thin film transistor including a source electrode, a drain electrode and an active layer; and an organic light emitting device. Here, a first electrode of the organic light emitting device may be in electrical contact with one of the source electrode and the drain electrode of the thin film transistor.
[0649] The thin film transistor may further include a gate electrode or a gate insulating layer, etc.
[0650] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like, but the embodiments of the present disclosure are not limited thereto.
[0651] The device may further include a sealing member for sealing the organic light-emitting device. The sealing member may allow an image from the organic light-emitting device to be implemented and may block external air and moisture from penetrating into the organic light-emitting device. The sealing member may be a sealing substrate including a transparent glass or plastic substrate. The sealing member may be a thin film encapsulation layer including a plurality of organic layers and / or a plurality of inorganic layers. When the sealing member is a thin film encapsulation layer, the entire device may be flexible.
[0652] For example, the device may be a lighting device, an authentication device, or an electronic device.
[0653] The light emitting device can be used as various appropriate displays, light sources, and the like.
[0654] The authentication device may be, for example, a biometric authentication device for authenticating an individual by using biometric information of a biometric body (eg, a fingertip or a pupil, etc.) The authentication device may further include a biometric information collector in addition to the organic light emitting device.
[0655] The electronic device can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various appropriate measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), projectors, etc., but the embodiments of the present disclosure are not limited thereto.
[0656] General definition of at least some substituents
[0657] As used herein, the term "C 1 -C 60 "Alkyl" refers to a straight or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, preferably "C 1 -C 20 As used herein, the term "C alkyl" is substituted with "C alkyl", and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 The structure of the alkyl group is basically a divalent group of the same structure.
[0658] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60The alkyl group is a hydrocarbon group having at least one carbon-carbon double bond at the main chain (e.g., in the middle) or at the end (e.g., terminal), and examples thereof include ethenyl, propenyl, and butenyl. As used herein, the term “C 2 -C 60 "Alkenylene" refers to a 2 -C 60 The structure of the alkenyl group is basically a divalent group of the same structure.
[0659] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., in the middle) or at the end (e.g., terminal), and examples thereof include ethynyl and propynyl. As used herein, the term “C 2 -C 60 "Alkyne" refers to a 2 -C 60 The structure of the alkynyl group is basically a divalent group of the same structure.
[0660] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (A 101 C 1 -C 60 A monovalent group represented by an alkyl group, preferably a "C 1 -C 20 "alkoxy group", and examples thereof include methoxy, ethoxy and isopropoxy.
[0661] As used herein, the term "C 3 -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 "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. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene group having a 3 -C 10 The structure of the cycloalkyl group is basically a divalent group of the same structure.
[0662] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10"Heterocycloalkylene" refers to a group having a C 1 -C 10 The structure of the heterocycloalkyl group is basically a divalent group of the same structure.
[0663] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity (eg, it is not aromatic), and examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 The structure of the cycloalkenyl group is basically a divalent group of the same structure.
[0664] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 The structure of the heterocycloalkenyl group is basically a divalent group of the same structure.
[0665] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), and the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms). 6 -C 60 Examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and 1,2-triphenylenyl. 6 -C 60 Aryl and C 6 -C 60 When each arylene group includes two or more rings, these rings may be fused to each other (eg, combined together). As used herein, the term "C 7 -C 60 "Alkylaryl" refers to a 1 -C 60Alkyl substituted C 6 -C 60 Aryl.
[0666] As used herein, the term "C 1 -C 60 The term "heteroaryl" as used herein refers to a monovalent group having a heterocyclic aromatic system (having at least one heteroatom selected from N, O, Si, P and S as a ring atom in addition to 1 to 60 carbon atoms). 1 -C 60 The term "heteroarylene group" refers to a divalent group having a heterocyclic aromatic system (having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms). 1 -C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, and isoquinolyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other (eg, combined together).
[0667] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" refers to -SA 103 (A 103 C 6 -C 60 aryl).
[0668] As used herein, the term "C 1 -C 60 "Heteroaryloxy" refers to -OA 104 (A 104 C 1 -C 60 Heteroaryl), as used herein, 1 -C 60 "Heteroarylthio" refers to -SA 105 (A 105 C 1 -C 60 Heteroaryl), as used herein, 2 -C 60 "Alkylheteroaryl" refers to -R 101 A106 (where R 101 C 1 -C 60 Alkylene, and A 106 C 1 -C 60 heteroaryl).
[0669] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other (e.g., combined together), having only carbon atoms as ring-forming atoms, and having no aromaticity (e.g., not aromatic) in its entire molecular structure. An example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic fused polycyclic group.
[0670] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused to each other (e.g., combined together), at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to carbon atoms, and having no aromaticity (e.g., not aromatic) in its entire molecular structure. An example of a monovalent non-aromatic fused heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic fused heteropolycyclic group.
[0671] As used herein, the term "C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group that includes only carbon as a ring atom and consists of 5 to 60 carbon atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The 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 group attached to C 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0672] As used herein, the term "C 1 -C 60 "Heterocyclic group" refers to a 5 -C 60The structure of the carbocyclic group is substantially the same as that of the group except that in addition to carbon (the number of carbon atoms may range from 1 to 60), at least one heteroatom selected from N, O, Si, P and S is used as a ring-forming atom.
[0673] Substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0674] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0675] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12)、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 );
[0676] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0677] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60Heteroarylthio group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 );as well as
[0678] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0679] Where Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, C substituted by at least one selected from deuterium, -F and cyano 1 -C 60 Alkyl, C substituted by at least one selected from deuterium, -F and cyano 6 -C 60 Aryl, biphenyl and terphenyl.
[0680] As used herein, the term "Ph" refers to phenyl, as used herein, the term "Me" refers to methyl, as used herein, the term "Et" refers to ethyl, as used herein, the term "tert-Bu" or "Bu t ” refers to tert-butyl, and the term “OMe” as used herein refers to methoxy.
[0681] As used herein, the term "biphenyl" refers to a "phenyl group substituted by a phenyl group". In other words, a "biphenyl group" is a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0682] As used herein, the term "terphenyl" refers to a "phenyl group substituted by a biphenyl group". In other words, a "terphenyl group" is a group having a C 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0683] Unless otherwise defined, * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula.
[0684] Hereinafter, the compound according to the embodiment and the organic light-emitting device according to the embodiment will be described in more detail with reference to Synthesis Examples and Examples. The phrase "using B instead of A" used in describing Synthesis Examples indicates that B is substituted for A with the same molar equivalent.
[0685] Example
[0686] Synthesis Example 1: Synthesis of Compound BD1
[0687] Compound BD1 was synthesized by referring to Scheme 1 described below.
[0688] Scheme I
[0689]
[0690] (1) Synthesis of intermediate compound [L1-1]
[0691] Iodobenzene (1.0 eq), imidazole (1.2 eq), CuI (0.01 eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethyl sulfonate (0.1M), and then stirred at a temperature of 130°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L1-1] (yield: 72%).
[0692] (2) Synthesis of intermediate compound [L1]
[0693] The intermediate compound [L1-1] (1.0 eq), diphenyliodotrifluoromethanesulfonate (OTf) (1.3 eq) and Cu(OAc) were reacted. 2(5mol%) was dissolved in dimethyl sulfonate (0.1M), and then, stirred at a temperature of 100°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L1] (yield: 60%).
[0694] (3) Synthesis of intermediate compound [L2-1]
[0695] 1,3-Dibromobenzene (1.0 eq), imidazole (3.0 eq), CuI (0.01 eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethyl sulfonate (0.1M), and then stirred at a temperature of 130°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L2-1] (yield: 50%).
[0696] (4) Synthesis of intermediate compound [L2]
[0697] Intermediate compound [L2-1] (1.0 eq) and iodomethane (5.0 eq) were dissolved in THF (1.0 M), and then stirred at a temperature of 70° C. for 12 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated using magnesium sulfate, and column chromatography was used to obtain intermediate compound [L2] (yield: 66%).
[0698] (5) Synthesis of compound BD1
[0699] The intermediate compound [L1] (1.0 eq), the intermediate compound [L2] (1.0 eq), IrCl 3 ·xH 2 O (1.2 eq) and KOAc (0.5 eq) were dissolved in propionic acid (0.1 M), and stirred at a temperature of 120° C. for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain compound BD1 (yield: 20%).
[0700] Synthesis Example 2: Synthesis of Compound BD7
[0701] Compound BD7 was synthesized by referring to Scheme II described below.
[0702] Solution II
[0703]
[0704] (1) Synthesis of intermediate compound [L1-1]
[0705] Iodobenzene (1.0 eq), imidazole (1.2 eq), CuI (0.01 eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethyl sulfonate (0.1M), and then stirred at a temperature of 130°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L1-1] (yield: 72%).
[0706] (2) Synthesis of intermediate compound [L1]
[0707] The intermediate compound [L1-1] (1.0 eq), diphenyliodonium trifluoromethanesulfonate (1.3 eq) and Cu(OAc) were mixed. 2 (5mol%) was dissolved in dimethyl sulfonate (0.1M), and then, stirred at a temperature of 100°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L1] (yield: 60%).
[0708] (3) Synthesis of intermediate compound [L3-1]
[0709] 1,3-Dibromo-5-(trifluoromethyl)benzene (1.0 eq), imidazole (3.0 eq), CuI (0.01 eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethyl sulfonate (0.1M), and then stirred at a temperature of 130°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L3-1] (yield: 50%).
[0710] (4) Synthesis of intermediate compound [L3]
[0711] Intermediate compound [L3-1] (1.0 eq) and iodomethane (5.0 eq) were dissolved in THF (1.0 M), and then stirred at a temperature of 70° C. for 12 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated using magnesium sulfate, and column chromatography was used to obtain intermediate compound [L3] (yield: 66%).
[0712] (5) Synthesis of compound BD7
[0713] The intermediate compound [L1] (1.0 eq), the intermediate compound [L3] (1.0 eq), IrCl 3 ·xH 2 O (1.2 eq) and KOAc (0.5 eq) were dissolved in propionic acid (0.1 M), and stirred at a temperature of 120° C. for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain compound BD7 (yield: 20%).
[0714] Synthesis Example 3: Synthesis of Compound BD33
[0715] Compound BD33 was synthesized by referring to the following Scheme III.
[0716] Scheme III
[0717]
[0718] (1) Synthesis of intermediate compound [L4-1]
[0719] 2-iodophenol (1.0 eq), imidazole (1.2 eq), CuI (0.01 eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethyl sulfonate (0.1M), and then stirred at a temperature of 130°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L4-1] (yield: 72%).
[0720] (2) Synthesis of intermediate compound [L4]
[0721] The intermediate compound [L4-1] (1.0 eq), diphenyliodonium trifluoromethanesulfonate (1.3 eq) and Cu(OAc) were mixed. 2(5mol%) was dissolved in dimethyl sulfonate (0.1M), and then, stirred at a temperature of 100°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L4] (yield: 60%).
[0722] (3) Synthesis of intermediate compound [L5-1]
[0723] 1,3-Dibromo-5-(trifluoromethyl)benzene (1.0 eq), benzimidazole (3.0 eq), CuI (0.01 eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethyl sulfonate (0.1M), and then stirred at a temperature of 130°C for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain an intermediate compound [L5-1] (yield: 50%).
[0724] (4) Synthesis of intermediate compound [L5]
[0725] Intermediate compound [L5-1] (1.0 eq) and iodomethane (5.0 eq) were dissolved in THF (1.0 M), and then stirred at a temperature of 70° C. for 12 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated using magnesium sulfate, and column chromatography was used to obtain intermediate compound [L5] (yield: 66%).
[0726] (5) Synthesis of compound BD33
[0727] The intermediate compound [L4] (1.0 eq), the intermediate compound [L5] (1.0 eq), IrCl 3 ·xH 2 O (1.2 eq) and KOAc (0.5 eq) were dissolved in propionic acid (0.1 M), and stirred at a temperature of 120° C. for 24 hours. The reaction mixture was cooled to room temperature, and then an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried and concentrated by using magnesium sulfate, and column chromatography was used to obtain compound BD33 (yield: 20%).
[0728] The compounds synthesized according to Synthesis Examples 1 to 3 1 H NMR and MS / FAB are shown in Table 1 below.
[0729] Those skilled in the art may readily recognize embodiments of compounds other than those shown in Table 1 by referring to the synthetic routes and starting materials described above.
[0730] Table 1
[0731]
[0732] Example 1
[0733] As an anode, an ITO / Ag / ITO substrate was cut into a size of 50 mm x 50 mm x 0.7 mm, ultrasonicated with acetone, isopropyl alcohol, and pure water for 15 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO substrate was provided to a vacuum deposition apparatus.
[0734] The compound 2-TNATA was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 60 nm, and then, NPB was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm.
[0735] Compound H56 as a host, and compound BD1 as a dopant were co-deposited on the hole transport layer to a weight ratio of 10:1 to form an emission layer having a thickness of 25 nm.
[0736] BAlq was deposited on the emission layer to form a hole blocking layer having a thickness of 5 nm, and then, Alq 3 Deposited on the hole blocking layer to form an electron transport layer having a thickness of 25 nm, and then, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 0.5 nm, and Al was deposited on the electron injection layer to form a cathode having a thickness of 150 nm, thereby completing the manufacture of the organic light-emitting device.
[0737] Example 2 and Example 3 and Comparative Examples 1 to 3
[0738] Organic light-emitting devices of Examples 2 and 3 and Comparative Examples 1 to 3 were manufactured in substantially the same manner as in Example 1, except that the emission layer was formed by using the compound shown in Table 2.
[0739] Evaluation Example
[0740] The organic light-emitting devices manufactured according to Examples 1 to 3 and Comparative Examples 1 to 3 were measured using Keithley MU 236 and a luminance meter PR650 at 1000 cd / m 2 The driving voltage (V), current density (mA / cm2 ), luminous efficiency (cd / A), maximum emission wavelength (nm) and lifetime (T 90 ), and the results are shown in Table 2. In Table 2, the lifespan (T 90 ) is a measure of the time it takes for the brightness to reach 90% of the initial brightness.
[0741] Table 2
[0742]
[0743]
[0744] As can be seen from Table 2, the organic light-emitting devices of Examples 1 to 3 have higher luminous efficiency and longer lifespan than the organic light-emitting devices of Comparative Examples 1 to 3.
[0745] The organic light emitting device according to an embodiment of the present disclosure has high efficiency and a long lifespan.
[0746] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects within each embodiment should generally be considered as other similar features or aspects that can be used in other embodiments. Although one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the appended claims and their equivalents.
Claims
1. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an organic layer between the first electrode and the second electrode and including an emission layer; and The organic light-emitting device includes at least one organic metal compound represented by Formula 1: Formula 1 M(L a ) n1 (L b ) n2 Among them, in formula 1, M is iridium; L a A ligand selected from the group consisting of the ligands represented by Formula 2-1 or Formula 2-2, n1 is 1, L b A ligand selected from the group consisting of Formula 3-1 and Formula 3-2, n2 is 1, L a and L b Different from each other, Wherein, in Formula 2-1 or Formula 2-2, A1 and A2 are each independently phenyl, X3 and X4 are each independently C, Y1 and Y2 are each independently C, T1, T2 and T3 are each independently a single bond, *-O-*' and *-S-*', wherein at least one of T1 and T2 is selected from *-O-*' and *-S-*', and T3 is a single bond, b1 to b3 are each independently an integer of 1, 2 or 3, R1, R2, R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, and substituted or unsubstituted C1-C 60 alkyl, a1 and a2 are each independently an integer selected from 0 to 10, Wherein, in Formula 3-1 or Formula 3-2, A 11 is phenyl, L1 and L2 are each independently selected from a single bond, c1 and c2 are each independently 1, 2 or 3, Y 11 For C, T 11 , T 12 and T 13 are each independently selected from a single bond, b11, b12 and b13 are each independently 1, 2 or 3, R 11 , R 12a , R 12b , R 12c , R 12d , R 12e , R 12f , R 12g , R 13a , R 13b , R 13c , R 13d , R 13e , R 13f and R 13g are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, and substituted or unsubstituted C1-C 60 alkyl, a11 is an integer selected from 0 to 10, and The substituted C1-C 60 At least one substituent of the alkyl group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl and C1-C 60 Alkoxy; Each of the following C1-C 60 Alkyl and C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, -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 ); -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 )和-P(=O)(Q 31 )(Q 32 ), Where Q 11 To Q 13 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl and C1-C 60 Alkoxy, * 1 ,* 2 and* 3 Each is a binding site with the central metal M of Formula 1, and * and *' each indicate a binding site with an adjacent atom.
2. The organic light emitting device according to claim 1, wherein: The first electrode is an anode, The second electrode is a cathode, and The organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer or any combination thereof. The organic light-emitting device according to claim 1 , wherein the emission layer comprises at least one of the organic metal compounds.
4. The organic light emitting device according to claim 3, wherein: The emission layer further comprises a host compound, The at least one organometallic compound included in the emission layer is a dopant, and The host compound is included in the emission layer in an amount greater than an amount of the at least one organic metal compound included in the emission layer.
5. The organic light emitting device according to claim 4, wherein: The main compound includes a second compound and a third compound, the at least one organometallic compound, the second compound and the third compound are different from one another, The second compound and the third compound form an exciplex, and The at least one organometallic compound does not form an exciplex with at least one of the second compound and the third compound.
6. The organic light emitting device according to claim 4, wherein: The absolute value of the difference between the lowest unoccupied molecular orbital energy level of the at least one organometallic compound and the lowest unoccupied molecular orbital energy level of the host compound is 0.1 eV to 1.0 eV, and An absolute value of a difference between a highest occupied molecular orbital energy level of the at least one organometallic compound and the highest occupied molecular orbital energy level of the host compound is 1.25 eV or less.
7. The organic light emitting device according to claim 1, wherein: The emission layer is a first emission layer that emits light of a first color, The organic light emitting device further includes, between the first electrode and the second electrode, i) at least one second emission layer emitting second color light or ii) at least one second emission layer emitting second color light and at least one third emission layer emitting third color light, The maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light are the same as or different from each other, and The first color light and the second color light are emitted in the form of mixed light, or the first color light, the second color light, and the third color light are emitted in the form of mixed light.
8. An organometallic compound represented by Formula 1: Formula 1 M(L a ) n1 (L b ) n2 in, In formula 1, M is iridium, L a A ligand selected from the group consisting of the ligands represented by Formula 2-1 or Formula 2-2, n1 is 1, L b A ligand selected from the group consisting of Formula 3-1 and Formula 3-2, n2 is 1, L a and L b Different from each other, Wherein, in Formula 2-1 or Formula 2-2, A1 and A2 are each independently phenyl, X3 and X4 are each independently C, Y1 and Y2 are each independently C, T1, T2 and T3 are each independently a single bond, *-O-*' and *-S-*', wherein at least one of T1 and T2 is selected from *-O-*' and *-S-*', and T3 is a single bond, b1 to b3 are each independently an integer of 1, 2 or 3, R1, R2, R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, and substituted or unsubstituted C1-C 60 alkyl, a1 and a2 are each independently an integer selected from 0 to 10, Wherein, in Formula 3-1 or Formula 3-2, A 11 is phenyl, L1 and L2 are each independently selected from a single bond, c1 and c2 are each independently 1, 2 or 3, Y 11 For C, T 11 , T 12 and T 13 are each independently selected from a single bond, b11, b12 and b13 are each independently 1, 2 or 3, R 11 , R 12a , R 12b , R 12c , R 12d , R 12e , R 12f , R 12g , R 13a , R 13b , R 13c , R 13d , R 13e , R 13f and R 13g are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, and substituted or unsubstituted C1-C 60 alkyl, a11 is an integer selected from 0 to 10, and The substituted C1-C 60 At least one substituent of the alkyl group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl and C1-C 60 Alkoxy; Each of the following C1-C 60 Alkyl and C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, -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 ); -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 ), Where Q 11 To Q 13 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl and C1-C 60 Alkoxy, * 1 ,* 2 and* 3 Each is a binding site with the central metal M of Formula 1, and * and *' each indicate a binding site with an adjacent atom.
9. The organometallic compound according to claim 8, wherein R1, R2, R 31 , R 32 , R 33 , R 34 , R 35 and R 36 Each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, and C1-C 20 alkyl; Each of the following C1-C 20 Alkyl: deuterium, -F, -Cl, -Br, -I and cyano.
10. The organometallic compound according to claim 8, wherein the organometallic compound is selected from compound BD1 to compound BD48:
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