Organic metal compound and organic light-emitting device comprising the same
By using organometallic compounds represented by Formula 1, especially their bimetallic complex structure and borane-based linkage, the problem of insufficient luminous efficiency and stability in the blue light emitting layer of organic light-emitting devices is solved, achieving high-efficiency and long-life luminous performance.
Patent Information
- Application Number
- CN202010738344.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-07-30
- Filing Date
- 2020-07-28
- Publication Date
- 2025-01-07
- Estimated Expiration
- 2040-07-28
AI Technical Summary
Existing organic light-emitting devices have shortcomings in terms of luminous efficiency and stability, especially in the performance of the blue light emitting layer, which has not reached the ideal level.
Organometallic compounds represented by Formula 1 are used. These compounds have a bimetallic complex structure and are linked by borane-based links of rings A3 and A4, as well as rings A6 and A7, to form internal dual-dopant charge transfer properties, which enhances the stability and luminescence efficiency of the compounds.
It improves the luminous efficiency and stability of organic light-emitting devices, especially exhibiting high efficiency and long lifespan phosphorescence characteristics in the blue light emitting layer.
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Figure CN112310296B_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0092659 filed on July 30, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more aspects of embodiments of the present disclosure relate to an organometallic compound and an organic light-emitting device including the same. Background Art
[0004] Organic light-emitting devices are self-emissive devices that produce full-color images, and may also have wide viewing angles, high contrast, short response times, and / or superior characteristics in terms of brightness, driving voltage, and / or response speed compared to devices in the related art.
[0005] The organic light-emitting device may include a first electrode arranged (positioned) on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially arranged on the first electrode. Holes provided by the first electrode may move to the emission layer through the hole transport region, and electrons provided by the second electrode may move to the emission layer through the electron transport region. Carriers (e.g., holes and electrons) may then recombine in the emission layer to generate excitons. These excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] One or more aspects of embodiments of the present disclosure relate to novel organometallic compounds and organic light-emitting devices including the same.
[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0008] Embodiments of the present disclosure provide an organometallic compound represented by Formula 1:
[0009] Formula 1
[0010]
[0011] In formula 1, M 1 and M 2 may be independently selected from the first row transition metals, the second row transition metals and the third row transition metals of the periodic table,
[0012] Y 1 To Y 8may be independently selected from carbon atoms (C) and nitrogen atoms (N),
[0013] T 1 To T 8 can each independently be a chemical bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R") or P(R')(R"), wherein when T 1 When Y is a chemical bond, 1 and M 1 Directly connected to each other, when T 2 When Y is a chemical bond, 2 and M 1 Directly connected to each other, when T 3 When Y is a chemical bond, 3 and M 1 Directly connected to each other, when T 4 When Y is a chemical bond, 4 and M 1 Directly connected to each other, when T 5 When Y is a chemical bond, 5 and M 2 Directly connected to each other, when T 6 When Y is a chemical bond, 6 and M 2 Directly connected to each other, when T 7 When Y is a chemical bond, 7 and M 2 directly connected to each other, and when T 8 When Y is a chemical bond, 8 and M 2 Directly connected to each other,
[0014] Selected from Y 1 or T 1 With M 1 The key between 2 or T 2 With M 1 The key between 3 or T 3 With M 1 The key between 4 or T 4 With M 1 Two of the bonds between may each be coordinate bonds, and the other two bonds may each be covalent bonds; and 5 or T 5 With M 2 The key between 6 or T 6 With M 2 The key between7 or T 7 With M 2 The key between 8 or T 8 With M 2 Two of the bonds between may each be coordinate bonds, and the other two bonds may each be covalent bonds,
[0015] Ring A 1 To Ring A 9 Can be independently selected from C 5 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups,
[0016] X 1 To X 4 can be independently O or S,
[0017] L 1 To L 5 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 10 )(R 11 )-*'、*-C(R 10 )=*'、*=C(R 10 )-*'、*-C(R 10 )=C(R 11 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 10 )-*'、*-N(R 10 )-*'、*-P(R 10 )-*'、*-Si(R 10 )(R 11 )-*'、*-P(R 10 )(R 11 )-*' and *-Ge(R 10 )(R 11 )-*',
[0018] a1 to a3 may be each independently selected from 0, 1, 2 and 3, wherein at least two of a1 to a3 may be each independently selected from 1, 2 and 3,
[0019] When a1 is 0, ring A 1 and Ring A 2 are not connected to each other. When a2 is 0, ring A 2 and Ring A 3 are not connected to each other, and when a3 is 0, ring A 1 and Ring A 4 Not connected to each other,
[0020] a4 and a5 can be each independently selected from 1, 2 and 3,
[0021] R', R" and R 1 To R 11 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, 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 )、-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 )(Q2 ),
[0022] b1 to b9 may each independently be an integer from 1 to 20,
[0023] Selected from R 1 To R 11 Any two substituents in may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0024] The substituted C 5 -C 60 The carbocyclic group, the substituted C 1 -C 60 Heterocyclic group, the substituted C 1 -C 60 The alkyl group, the substituted C 2 -C 60 The alkenyl group, the substituted C 2 -C 60 Alkynyl group, the substituted C 1 -C 60 Alkoxy groups, the substituted C 3 -C 10 Cycloalkyl group, the substituted C 1 -C 10 Heterocycloalkyl group, the substituted C 3 -C 10 Cycloalkenyl group, the substituted C 1 -C 10 Heterocycloalkenyl group, the substituted C 6 -C 60 The aryl group, the substituted C 6 -C 60 The aryloxy group, the substituted C 6 -C 60 Arylthio group, the 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 may be selected from:
[0025] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;
[0026] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl group, 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 ) at least one substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;
[0027] C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0028] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) at least one substituted C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and
[0029] -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 ),
[0030] Q 1 To Q 3 , 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, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups,
[0031] * and *' each represent a site of attachment to an adjacent atom, and
[0032] B represents a boron atom, and O represents an oxygen atom.
[0033] Another embodiment of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode, the organic layer including an emission layer; and at least one organic metal compound of the present embodiment.
[0034] Another embodiment of the present disclosure provides a display device comprising: a thin film transistor comprising a source electrode, a drain electrode and an active layer; and the organic light-emitting device, wherein the first electrode of the organic light-emitting device is electrically contacted with one of the source electrode and the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF THE DRAWINGS
[0035] These and / or other aspects will become apparent and more readily appreciated from the following description of embodiments of the present disclosure taken in conjunction with the accompanying drawings, in which:
[0036] Figures 1 to 4 is a schematic diagram of an organic light-emitting device according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION
[0037] Now will be referred to in more detail embodiment, the example of the embodiment is illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the text, and repetitive description may not be provided.In this respect, the current embodiment may have different forms and should not be construed as being limited to the description set forth herein.Therefore, by referring to the accompanying drawings, only the embodiment is described below to explain the aspect of the current description.As used herein, the term "and / or" includes one or more than one arbitrary combination and all combinations of the related listed items.Such as "at least one (kind) in ... ", "one (kind) in ... ", "selected from", "selected from at least one (kind) in ... " and "selected from one (kind) in ... " when before a column of elements, modify the elements of the entire column, and do not modify the single element of the column.
[0038] For clarity, the thickness of layers, films, plates, regions, etc. may be exaggerated in the accompanying drawings. It should be understood that when an element such as a layer, film, region, and / or substrate is referred to as being "on" another element, it may be directly on the other element or there may be intervening elements. Conversely, when an element is referred to as being "directly on" another element, there are no intervening elements. In addition, when describing embodiments of the present disclosure, the use of "may" may refer to "one or more than one embodiments of the present disclosure."
[0039] Embodiments of the present disclosure provide an organometallic compound represented by the following Formula 1:
[0040] Formula 1
[0041]
[0042] In formula 1, M 1 and M 2 Each may be independently selected from the first row transition metals, the second row transition metals and the third row transition metals of the periodic table.
[0043] In one or more than one embodiment, in Formula 1, M 1 and M 2 Each may be independently selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru and Os.
[0044] For example, M 1 and M 2 Each may be Pt, but the embodiments of the present disclosure are not limited thereto.
[0045] In formula 1, Y 1 To Y 8 may be independently selected from carbon atoms (C) and nitrogen atoms (N),
[0046] T 1 To T 8 can each independently be a chemical bond (e.g., a single bond), O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R"), or P(R')(R"), wherein when T 1 When Y is a chemical bond, 1 and M 1 can be directly connected to each other, when T 2 When Y is a chemical bond, 2 and M 1 can be directly connected to each other, when T 3 When Y is a chemical bond, 3 and M1 can be directly connected to each other, when T 4 When Y is a chemical bond, 4 and M 1 can be directly connected to each other, when T 5 When Y is a chemical bond, 5 and M 2 can be directly connected to each other, when T 6 When Y is a chemical bond, 6 and M 2 can be directly connected to each other, when T 7 When Y is a chemical bond, 7 and M 2 can be directly connected to each other, and when T 8 When Y is a chemical bond, 8 and M 2 can be connected directly to each other, and
[0047] Selected from Y 1 or T 1 With M 1 The key between 2 or T 2 With M 1 The key between 3 or T 3 With M 1 The key between 4 or T 4 With M 1 Two of the bonds between may each be coordinate bonds, and the other two bonds may each be covalent bonds; and 5 or T 5 With M 2 The key between 6 or T 6 With M 2 The key between 7 or T 7 With M 2 The key between 8 or T 8 With M 2 Two of the bonds between may each be coordinate bonds, and the other two bonds may each be covalent bonds.
[0048] In one or more than one embodiment, in Formula 1, T 1 To T 4 Can each be a chemical bond, selected from Y 1 With M 1 The key between 2 With M 1 At least one of the bonds between Y 1 Can be C, Y 2Can be C or N, T 5 To T 8 Can each be a chemical bond, selected from Y 5 With M 2 The key between 8 With M 2 At least one of the bonds between Y 5 Can be C, and Y 8 Can be C or N.
[0049] For example, T 1 To T 8 Each may be a single bond.
[0050] For example, in Formula 1, Y 3 and Y 4 Can each be C, and Y 6 and Y 7 Each may be C, but the embodiments of the present disclosure are not limited thereto.
[0051] For example, in Formula 1, Y 1 To Y 8 Can be C, or
[0052] Y 1 and Y 3 To Y 7 Can each be C, and Y 2 and Y 8 Each may be N, but the embodiments of the present disclosure are not limited thereto.
[0053] In Formula 1, Ring A 1 To Ring A 9 Can be independently selected from C 5 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups,
[0054] X 1 To X 4 can be independently O or S,
[0055] L 1 To L 5 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 10 )(R 11 )-*'、*-C(R 10 )=*'、*=C(R 10 )-*'、*-C(R 10 )=C(R 11)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 10 )-*'、*-N(R 10 )-*'、*-P(R 10 )-*'、*-Si(R 10 )(R 11 )-*'、*-P(R 10 )(R 11 )-*' and *-Ge(R 10 )(R 11 )-*',
[0056] a1 to a3 may be each independently selected from 0, 1, 2 and 3, wherein at least two of a1 to a3 may be each independently selected from 1, 2 and 3,
[0057] When a1 is 0, ring A 1 and Ring A 2 They can be disconnected. When a2 is 0, ring A 2 and Ring A 3 may not be connected to each other, and when a3 is 0, ring A 1 and Ring A 4 Can be disconnected from each other,
[0058] a4 and a5 can be each independently selected from 1, 2 and 3,
[0059] R', R" and R 1 To R 11 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, 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 )、-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 ),
[0060] b1 to b9 may each independently be an integer from 1 to 20, and
[0061] Selected from R 1 To R 11 Any two substituents in may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic group.
[0062] In one or more than one embodiment, A in Formula 1 1 To A 9Each of the phenyl groups may be independently selected from a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a 1,2,4-triazole group, a tetrazole group, an azathiole group, a diazathiole group, a triazathiole group, a benzimidazole group, an imidazopyridine group, an imidazopyrazine group, a cyclohexane group, and a cyclohexene group.
[0063] In one or more than one embodiment, Ring A 2 and Ring A 8 One or more of the may each independently be a 5-membered ring containing two or more N atoms, or a condensed ring containing a 5-membered ring containing two or more N atoms.
[0064] For example, in Formula 1, Ring A 1 may be selected from a cyclopentadiene group, a furan group, a thiophene group and a pyrrole group,
[0065] Ring A 2 and Ring A 8 may be each independently selected from a pyrazole group, an imidazole group, a benzimidazole group, an imidazopyridine group and an imidazopyrazine group, and
[0066] Ring A 3 To Ring A 7 and Ring A 9 Each may be a phenyl group, but the embodiments of the present disclosure are not limited thereto.
[0067] In one or more than one embodiment, in Formula 1, Ring A 1 It may be a group represented by formula 2-1:
[0068] Formula 2-1
[0069]
[0070] In formula 2-1,
[0071] Y 21 It can be C(R 21 )(R 22 )、N(R 21 ), O or S,
[0072] R 21 and R 22 can be independently related to R', R" and R 1To R 11 Same as described, and
[0073] * indicates the same as T 1 The connection site of L 3 The connection site of T 5 The attachment site of L 4 connection site.
[0074] In one or more than one embodiment, in Formula 1, Ring A 2 and Ring A 8 Each may be independently a group represented by one of Formula 2-2(1) to Formula 2-2(4):
[0075]
[0076] In equations 2-2(1) to 2-2(4),
[0077] Y 21 Can be N or C (R 21 ), Y 22 Can be N or C (R 22 ), Y 23 Can be N or C (R 23 ), and Y 24 Can be N or C (R 24 ),
[0078] R 21 To R 25 can be independently related to R', R" and R 1 To R 11 Same as described, and
[0079] * indicates ring A 2 With T 2 The attachment site or loop A 8 With T 8 and *' indicates the attachment site of ring A 2 With L 2 The attachment site or loop A 8 With L 5 connection site.
[0080] In one or more than one embodiment, i) X 1 To X 4 Can be O, ii) X 1 To X 4 Each of them can be S, or iii) X 1 and X 2 can be O, and X 3 and X 4They can each be S.
[0081] In one or more than one embodiments, a1 may be 0, a2 to a5 may each be 1, and L 2 To L 5 Each may be a single bond.
[0082] In one or more than one embodiment, R', R" and R 1 To R 11 Can be independently selected from:
[0083] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;
[0084] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl groups and C 1 -C 20 At least one substituted C 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;
[0085] a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group; and
[0086] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, -Si(Q 31 )(Q 32 )(Q 33)、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group and triazinyl group; and
[0087] -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 ),as well as
[0088] Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 20 Aryl group, C 1 -C 20Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups.
[0089] For example, i) R 1 Can be C 1 -C 20 Alkyl group, b1 can be 1, and R 2 To R 9 may each independently be hydrogen; ii) R 2 and R 8 Can be independently C 1 -C 20 The alkyl group, b2 and b8 may each independently be 1 or 2, and R 1 , R 3 To R 7 and R 9 may each independently be hydrogen, or iii) R 1 To R 9 may each independently be hydrogen, but embodiments of the present disclosure are not limited thereto.
[0090] In one or more than one embodiments, the organometallic compound represented by Formula 1 may be represented by Formula 1-1:
[0091] Formula 1-1
[0092]
[0093] In formula 1-1,
[0094] M 1 、M 2 , Ring A 1 To Ring A 9 , Y 1 To Y 8 , L 2 To L 5 , X 1 To X 4 , R 1 To R 9 and b1 to b9 may each independently be the same as described above.
[0095] In one or more than one embodiment, the organometallic compound may be selected from Compound BD1 to Compound BD96, but the embodiments of the present disclosure are not limited thereto:
[0096]
[0097]
[0098]
[0099]
[0100] Since the organometallic compound represented by Formula 1 has a bimetallic complex structure, the organometallic compound may exhibit excellent luminescent characteristic effects having high luminescent efficiency compared to light absorption due to a heavy effect (eg, due to a relatively large weight).
[0101] In addition, since the organometallic compound represented by Formula 1 includes a connecting ring A 3 and Ring A 4 and Ring A 6 and Ring A 7 The borane-based part of the organometallic compound can therefore exhibit properties similar to those of thermally activated delayed fluorescence (TADF) materials due to the internal dual-dopant charge transfer (CT) emission effect.
[0102] In addition, since the organometallic compound represented by Formula 1 has a biligand structure, the bimetallic complex is not connected via a single bond but via ring A. 1 The ligands are connected to each other, so the structure of the compound becomes more rigid, thereby increasing its stability. Here, the formation of excimers can be suppressed (or reduced) by further tilting the angle between the ligands relative to the core metal, thereby realizing a phosphorescent organic light-emitting device with high efficiency and long service life.
[0103] An organic light-emitting device to which the organometallic compound represented by Formula 1 is applied may have high durability and a long service life.
[0104] The organometallic compound may emit blue light. For example, the organometallic compound may emit blue light having a maximum emission wavelength of about 440 nm or more and less than about 470 nm (e.g., about 445 nm or more and about 465 nm or less). x,y Color coordinates 0.15, 0.15 to 0.30), but the embodiments of the present disclosure are not limited thereto. Therefore, the organometallic compound represented by Formula 1 can be usefully (suitably) used to manufacture an organic light-emitting device that emits blue light.
[0105] The synthesis methods for the organometallic compound represented by Formula 1 should become apparent to one of ordinary skill in the art by referring to the following examples.
[0106] At least one organometallic compound of Formula 1 can be used (adopted) between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound can be included in the emission layer. The organometallic compound can act as a dopant in the emission layer. In one or more than one embodiments, the organometallic compound represented by Formula 1 can be used as a material for a covering layer positioned outside a pair of electrodes of an organic light-emitting device.
[0107] Therefore, another embodiment of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode, the organic layer including an emission layer; and at least one organic metal compound represented by Formula 1.
[0108] For example, the organic layer may include at least one organic metal compound represented by Formula 1.
[0109] The expression “(the organic layer) contains at least one organic metal compound represented by Formula 1” used herein may include the case where “(the organic layer) contains one identical organic metal compound represented by Formula 1” and the case where “(the organic layer) contains two or more different organic metal compounds represented by Formula 1”.
[0110] In some embodiments, for example, the organic layer may include only compound BD1 as an organic metal compound. In this regard, compound BD1 may only be present (e.g., included) in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include compound BD1 and compound BD2 as organic metal compounds. In this regard, compound BD1 and compound BD2 may be present (e.g., included) in the same layer (e.g., compound BD1 and compound BD2 may both (e.g., simultaneously) be present in the emission layer), or in different layers (e.g., compound BD1 may be present in the emission layer, and compound BD2 may be present in the electron transport region).
[0111] In one or more than one embodiments,
[0112] The first electrode of the organic light-emitting device may be an anode,
[0113] The second electrode of the organic light emitting device may be a cathode, and
[0114] The organic layer may further include 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,
[0115] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
[0116] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0117] The term "organic layer" as used herein may refer to a single layer and / or a plurality of layers disposed between a first electrode and a second electrode of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.
[0118] In one or more than one embodiments, the emissive layer may comprise an organometallic compound.
[0119] For example, the emission layer may further include a host, and the organic metal compound may be a phosphorescent material or a delayed fluorescent material. The amount of the host in the emission layer may be greater than the amount of the organic metal compound in the emission layer.
[0120] In one or more than one embodiments, at least one of the emission layer, the hole transport region, and the electron transport region may include at least one selected from the group consisting of a carbazole-based compound, a silicon-based compound, a sulfur oxide, and a phosphorus oxide.
[0121] In one or more than one embodiments, at least one of the hole transporting region and the electron transporting region can comprise an organometallic compound.
[0122] Figure 1 Description
[0123] Figure 1 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment of the present disclosure. The organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .
[0124] 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 of the present disclosure are described.
[0125] First electrode 110
[0126] exist Figure 1 In the embodiment, a substrate may be additionally disposed under the first electrode 110 and / or over the second electrode 190. The substrate may be a glass substrate and / or a plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.
[0127] 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 forming the first electrode 110 may be selected from materials having a high work function, thereby facilitating hole injection.
[0128] 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 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 than one embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0129] 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.
[0130] Organic layer 150
[0131] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.
[0132] The organic layer 150 may further include 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 .
[0133] Hole transport region in the organic layer 150
[0134] The hole transport region may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers containing a plurality of different materials.
[0135] 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.
[0136] For example, the hole transport zone may have a single-layer structure including a single layer containing a plurality of different materials, or a multi-layer 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 in sequence from the first electrode 110 in this prescribed order, but the structure of the hole transport zone is not limited thereto.
[0137] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
[0138]
[0139] Formula 201
[0140]
[0141] Formula 202
[0142]
[0143] In equation 201 and equation 202,
[0144] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0145] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene group, substituted or unsubstituted C 2 -C 20 Alkenylene group, substituted or unsubstituted C3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0146] xa1 to xa4 can each independently be an integer from 0 to 3,
[0147] xa5 can be an integer from 1 to 10, and
[0148] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0149] For example, in Equation 202, R 201 and R 202 can optionally be linked to each other via single bonds, dimethyl-methylene groups or diphenyl-methylene groups, and / or R 203 and R 204They may optionally be linked to one another via single bonds, dimethyl-methylene groups or diphenyl-methylene groups.
[0150] In one or more than one embodiments, in Formula 201 and Formula 202,
[0151] L 201 To L 205 Can be independently selected from:
[0152] a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthenylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenylene group, a phenanthrenylene group, a py ... a phenylene group, a tetraphenylene group, a perylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a rubinylene group, a coronene group, an ovphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group; and
[0153] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a tetraphenyl group, a pyrenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, a pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one substituted phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthenylene group, fluorenylene group, spiro-difluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, phenanthrenylene group, py ... a phenylene group, a tetraphenylene group, a perylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a rubinylene group, a coronene group, an ovphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group, and
[0154] Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0155] In one or more than one embodiments, xa1 to xa4 can each independently be 0, 1 or 2.
[0156] In one or more than one embodiments, xa5 can be 1, 2, 3 or 4.
[0157] In one or more than one embodiment, R 201 To R 204 and Q 201 Can be independently selected from:
[0158] a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group; and
[0159] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a tetraphenyl group, a pyrenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, a pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32) is at least one substituted phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group, and
[0160] Q 31 To Q 33 Same as described above.
[0161] In one or more than one embodiment, R selected from Formula 201 201 To R 203 At least one of can be independently selected from:
[0162] fluorenyl groups, spiro-bifluorenyl groups, carbazolyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups; and
[0163] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group substituted with at least one of a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
[0164] However, embodiments of the present disclosure are not limited thereto.
[0165] In one or more than one embodiment, in Formula 202, i) R 201 and R 202may be linked 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.
[0166] In one or more than one embodiment, R selected from Formula 202 201 To R 204 At least one of can be independently selected from:
[0167] a carbazolyl group; and
[0168] is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a carbazolyl group substituted with at least one of a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothienyl group,
[0169] However, embodiments of the present disclosure are not limited thereto.
[0170] The compound represented by Formula 201 can be represented by Formula 201A:
[0171] Formula 201A
[0172]
[0173] In one or more than one embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:
[0174] Formula 201A(1)
[0175]
[0176] In one or more than one embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but the embodiments of the present disclosure are not limited thereto:
[0177] Formula 201A-1
[0178]
[0179] In one or more than one embodiments, the compound represented by Formula 202 can be represented by the following Formula 202A:
[0180] Formula 202A
[0181]
[0182] In one or more than one embodiments, the compound represented by Formula 202 can be represented by the following Formula 202A-1:
[0183] Formula 202A-1
[0184]
[0185] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,
[0186] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 may independently be the same as described above,
[0187] R 211 and R 212 You can refer to this article about R 203 Description provided to understand.
[0188] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, The invention also includes but is not limited to: a benzothiophenyl group, a tetraphenyl group, a peryl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group.
[0189] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT39, but embodiments of the present disclosure are not limited thereto:
[0190]
[0191]
[0192]
[0193] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to about And for example, about to about and the thickness of the hole transport layer may be about to about And for example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, satisfactory (or suitable) hole transport characteristics may be obtained without a significant increase in driving voltage.
[0194] The emission auxiliary layer can increase the light emission efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer (for example, by adjusting the optical resonance distance to match the wavelength of the light emitted from the emission layer), and the electron blocking layer can block or reduce the flow of electrons from the electron transport region (for example, further flow into the hole transport region). The emission auxiliary layer and the electron blocking layer can each independently contain any one of the materials described above, or be formed of any one of the materials described above.
[0195] p-dopant
[0196] In addition to the materials described above, the hole transport region may further include a charge generating material for improving the conductive property. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.
[0197] The charge generating material may be, for example, a p-dopant.
[0198] In one or more embodiments, the p-dopant can have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.
[0199] 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 embodiments of the present disclosure are not limited thereto.
[0200] In one or more than one embodiments, the p-dopant may include at least one selected from the group consisting of:
[0201] Quinone derivatives, for example tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0202] Metal oxides, such as tungsten oxide and / or molybdenum oxide;
[0203] 1,4,5,8,9,12-Hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
[0204] A compound represented by the following formula 221,
[0205] However, the embodiments of the present disclosure are not limited thereto:
[0206]
[0207]
[0208] Formula 221
[0209]
[0210] In formula 221,
[0211] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, wherein R is selected from 221 To R 223 At least one of the may have a cyano group, -F, -Cl, -Br, -I, C substituted by -F 1 -C 20 Alkyl groups, C substituted by -Cl 1 -C 20 Alkyl groups, C substituted with -Br 1 -C 20 Alkyl groups and C substituted by -I 1 -C 20 At least one substituent in the alkyl group.
[0212] Emission layer in the organic layer 150
[0213] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, 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 may be in contact with each other or may be spaced apart from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red-emitting material, a green-emitting material, and a blue-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0214] The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant. The phosphorescent dopant may include an organic metal compound represented by Formula 1.
[0215] In the emission layer, the amount of the dopant may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0216] 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 (or suitable) light emission characteristics may be obtained without a significant increase in driving voltage.
[0217] Subject in the emission layer
[0218] In one or more than one embodiments, the host may include a compound represented by the following formula 301:
[0219] Formula 301
[0220] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0221] In formula 301,
[0222] Ar 301 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0223] xb11 can be 1, 2 or 3,
[0224] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0225] xb1 can be an integer from 0 to 5.
[0226] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2-C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, 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 ),
[0227] xb21 can be an integer from 1 to 5,
[0228] Q 301 To Q 303 Can be independently selected from C 1 -C 10 Alkyl group, 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.
[0229] In one or more than one embodiment, Ar in Formula 301 301 Can be selected from:
[0230] naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a naphthacene group, a phenanthrene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group; and
[0231] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, groups, naphthacene groups, phenanthracene groups, perylene groups, pentaphenyl groups, indenoanthracene groups, dibenzofuran groups and dibenzothiophene groups, and
[0232] Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, 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.
[0233] When xb11 in Formula 301 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.
[0234] In one or more than one embodiments, the compound represented by Formula 301 can be represented by the following Formula 301-1 or Formula 301-2:
[0235] Formula 301-1
[0236]
[0237] Formula 301-2
[0238]
[0239] In Formula 301-1 and Formula 301-2,
[0240] Ring A 301 To Ring A 304 can be independently a benzene ring, a naphthalene ring, a phenanthrene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, a pyridine ring, a pyrimidine ring, an indene ring, a fluorene ring, a spiro-bifluorene ring, a benzofluorene ring, a dibenzofluorene ring, an indole ring, a carbazole ring, a benzocarbazole ring, a dibenzocarbazole ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a naphthofuran ring, a benzonaphthofuran ring, a dinaphthofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, a benzonaphthothiophene ring or a dinaphthothiophene ring,
[0241] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0242] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -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 ),
[0243] xb22 and xb23 can each independently be 0, 1 or 2,
[0244] L 301 、xb1、R 301 and Q31 To Q 33 can be independently the same as described above,
[0245] L 302 To L 304 can be independently determined by referring to L 301 The description presented is to understand,
[0246] xb2 to xb4 can each be independently understood by referring to the description presented with respect to xb1, and
[0247] R 302 To R 304 can be independently determined by referring to R 301 Description presented to understand.
[0248] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:
[0249] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group , pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and
[0250] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenyl group, anthracenylene group, fluoranthenylene group, phenylphenanthrenyl group, pyrenylene ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group , a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolylene group, an isoquinolylene group, a benzoquinolylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, and
[0251] Q 31 To Q 33 may each independently be the same as described above.
[0252] In one or more than one embodiments, in Formula 301, Formula 301-1 and Formula 301-2, R 301 To R 304 Can be independently selected from:
[0253] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group , pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, benzoquinolyl groups, phthalazinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, benzimidazolyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, imidazopyridinyl groups, imidazopyrimidinyl groups, and azacarbazolyl groups; and
[0254] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group , a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, and
[0255] Q 31 To Q 33 may each independently be the same as described above.
[0256] In one or more embodiments, the host can include an alkaline earth metal complex. For example, the host can be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.
[0257] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
[0258]
[0259]
[0260]
[0261] In one or more embodiments, the host may include at least one selected from a silicon-containing compound (eg, BCPDS, etc., used in the following examples) and a phosphine oxide-containing compound (eg, POPCPA, etc., used in the following examples).
[0262] However, embodiments of the present disclosure are not limited thereto. In one or more than one embodiments, the host may include only one compound, or two or more than two different compounds (eg, the host used in the following examples includes BCPDS and POPCPA).
[0263] The phosphorescent dopant contained in the emission layer in the organic layer 150
[0264] The phosphorescent dopant may include an organic metal compound represented by Formula 1 above.
[0265] In addition, the phosphorescent dopant may include an organic metal complex represented by the following Formula 401:
[0266] Formula 401
[0267] M(L 401 ) xc1 (L 402 ) xc2
[0268] Formula 402
[0269]
[0270] In equations 401 and 402,
[0271] 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),
[0272] L 401 The ligand represented by the formula 402 may be selected, and xc1 may be 1, 2 or 3, wherein when xc1 is two or more than two, two or more L 401 can be the same or different from each other,
[0273] L 402It can be an organic ligand, and xc2 can be an integer from 0 to 4, wherein when xc2 is two or more than two, two or more L 402 can be the same or different from each other, X 401 To X 404 may each independently be nitrogen or carbon,
[0274] X 401 and X 403 can be connected via single or double bonds, and X 402 and X 404 Can be connected via single or double bonds,
[0275] A 401 and A 402 Can be independently selected from C 5 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups,
[0276] 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=*', where Q 411 and Q 412 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group,
[0277] X 406 Can be a single bond, O or S,
[0278] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 20 Alkyl groups, substituted or unsubstituted C 1 -C 20 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1-C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 Alkoxy group, C 6 -C 20 Aryl groups and C 1 -C 20 Heteroaryl groups,
[0279] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0280] * and *' in Formula 402 each represent a bonding site to M in Formula 401.
[0281] In one or more than one embodiments, A in Formula 402 401 and A 402Each of the phenyl groups may be independently selected from a phenyl group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group.
[0282] In one or more than one embodiment, in Formula 402, i) X 401 may be nitrogen, and X 402 It can be carbon, or ii) X 401 and X 402 Each may be nitrogen at the same time (simultaneously).
[0283] In one or more than one embodiments, R in Formula 402 401 and R 402 Can be independently selected from:
[0284] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;
[0285] each of which is substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, and a norbornenyl group; 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;
[0286] a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
[0287] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group substituted with at least one of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
[0288] -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 ),as well as
[0289] Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl group, 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.
[0290] In one or more embodiments, in Formula 401, when xc1 is 2 or greater than 2, two or more L 401 Two A's 401 Optionally, X may be linked to 407 connected to each other, or when xc1 is 2 or greater, two A 402Optionally, X may be linked to 408 are connected to each other (see, for example, Compound PD1 to Compound PD4 and Compound PD7). 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 group, C 1 -C 20 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group), but the embodiments of the present disclosure are not limited thereto.
[0291] L in Formula 401 402 It can be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand. 402 It may be selected from halogen, diketone (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), -C(=O), isonitrile, -CN, and phosphorus (e.g., phosphine and / or phosphite), but the embodiments of the present disclosure are not limited thereto.
[0292] In one or more than one embodiments, the phosphorescent dopant may be selected from, for example, Compound PD1 to Compound PD25, but the embodiments of the present disclosure are not limited thereto:
[0293]
[0294]
[0295] Fluorescent dopants in the emitting layer
[0296] The fluorescent dopant may include an arylamine compound and / or a styrylamine compound.
[0297] The fluorescent dopant may include a compound represented by the following Formula 501:
[0298] Formula 501
[0299]
[0300] In formula 501,
[0301] Ar 501It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0302] L 501 To L 503 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0303] xd1 to xd3 may each independently be an integer from 0 to 3,
[0304] R 501 and R 502 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, and
[0305] xd4 can be an integer from 1 to 6.
[0306] In one or more than one embodiment, Ar in Formula 501 501 Can be selected from:
[0307] naphthyl group, heptalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a naphthacene group, a phenanthrene group, a perylene group, a pentaphenyl group, an indenoanthracene group, and an indenophenanthrene group; and
[0308] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 a naphthyl group substituted with at least one of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, a heptalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, group, a naphthacene group, a phenanthrene group, a perylene group, a pentaphenyl group, an indenoanthracene group and an indenophenanthrene group.
[0309] In one or more than one embodiment, L in Formula 501 501 To L 503 Can be independently selected from:
[0310] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group; and
[0311] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, The invention also includes at least one substituted phenylene group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, anthracen ... The invention also includes but is not limited to: a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group.
[0312] In one or more than one embodiment, R in Formula 501 501 and R 502 Can be independently selected from:
[0313] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group; and
[0314] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, a pyridyl group, and -Si(Q) 31 )(Q 32 )(Q 33 ) is at least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group, and
[0315] Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0316] In one or more than one embodiments, xd4 in Formula 501 may be 2, but embodiments of the present disclosure are not limited thereto.
[0317] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:
[0318]
[0319]
[0320]
[0321] In one or more than one embodiment, the fluorescent dopant may be selected from the following compounds, but the embodiments of the present disclosure are not limited thereto:
[0322]
[0323] Electron transport region in the organic layer 150
[0324] 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.
[0325] 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.
[0326] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers of each structure are stacked sequentially from the emission layer. However, the embodiment of the structure of the electron transport region is not limited thereto.
[0327] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, and / or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π-electron-depleted nitrogen-containing ring.
[0328] As used herein, the term "π-electron-depleted nitrogen-containing ring" may refer to a C-type ring having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group.
[0329] 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 of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' moiety is fused to at least one C 5 -C 60 A carbocyclic group is a fused heteropolycyclic group.
[0330] Non-limiting examples of π-electron-depleted nitrogen-containing rings include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, but embodiments of the present disclosure are not limited thereto.
[0331] For example, the electron transport region may include a compound represented by the following Formula 601:
[0332] Formula 601
[0333] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0334] In formula 601,
[0335] Ar 601 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0336] xe11 can be 1, 2 or 3,
[0337] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group;
[0338] xe1 can be an integer from 0 to 5,
[0339] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, 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 ),as well as
[0340] Q 601 To Q 603 Can be independently C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, and
[0341] xe21 can be an integer from 1 to 5.
[0342] In one or more embodiments, the amount of Ar 601 and xe21 number of R 601 At least one of the may comprise a π-electron-depleted nitrogen-containing ring.
[0343] In one or more than one embodiment, Ar in Formula 601 601 Can be selected from:
[0344] phenyl group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthrenes group, anthracene group, fluoranthene group, triphenylene group, pyrene group, a tetraphenyl group, a phenanthracene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and
[0345] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted phenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthrenyl group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group, and
[0346] Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, C1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0347] When xe11 in formula 601 is 2 or greater, two or more Ar 601 Can connect via one-touch.
[0348] In one or more than one embodiment, Ar in Formula 601 601 It may be an anthracene group.
[0349] In one or more than one embodiments, the compound represented by Formula 601 can be represented by the following Formula 601-1:
[0350] Formula 601-1
[0351]
[0352] In formula 601-1,
[0353] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and selected from X 614 To X 616 At least one of may be N,
[0354] L 611 To L 613 can be independently determined by referring to L 601 The description presented is to understand,
[0355] xe611 to xe613 can each be independently understood by referring to the description presented about xe1,
[0356] R 611 To R 613 can be independently determined by referring to R 601 Present the description to understand, and
[0357] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0358] In one or more than one embodiments, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Can be independently selected from:
[0359] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group , pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and
[0360] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a The invention also includes a phenylene group substituted by at least one of a phthalazinyl group, a naphthyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracene group, a fluoranthenyl group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolylene group, an isoquinolylene group, a benzoquinolylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridylene group, an imidazopyrimidinylene group, and an azacarbazolylene group,
[0361] However, embodiments of the present disclosure are not limited thereto.
[0362] In one or more than one embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each independently be 0, 1 or 2.
[0363] In one or more than one embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Can be independently selected from:
[0364] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group a benzoxazolyl group, a benzoxazolyl group, a benzoxazolyl group, a triazine group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;
[0365] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a a phenyl group substituted by at least one of a benzoimidazole group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group , pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, benzoquinolyl groups, phthalazinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, benzimidazolyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, imidazopyridinyl groups, imidazopyrimidinyl groups, and azacarbazolyl groups; and
[0366] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),as well as
[0367] Q 601 and Q 602 may each independently be the same as described above.
[0368] 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:
[0369]
[0370]
[0371]
[0372]
[0373] In one or more than one embodiment, the electron transport region may include a 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) and NTAZ:
[0374]
[0375] In one or more than one embodiment, the electron transport region may include a phosphine oxide-containing compound (e.g., TSPO1, etc., used in the following examples), but the embodiments of the present disclosure are not limited thereto. In one or more than one embodiment, a phosphine oxide-containing compound may be used in a hole blocking layer in the electron transport region, but the embodiments of the present disclosure are not limited thereto.
[0376] The thickness of the buffer layer, the hole blocking layer, and the electron control layer may each independently 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 each independently within any of these ranges, the electron transport region can have excellent (or suitable) hole blocking characteristics and / or electron control characteristics without a significant increase in driving voltage.
[0377] 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 above-described range, the electron transport layer may have satisfactory (or suitable) electron transport characteristics without a significant increase in driving voltage.
[0378] 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.
[0379] 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 the embodiments of the present disclosure are not limited thereto.
[0380] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium hydroxyquinoline, LiQ) and / or compound ET-D2:
[0381]
[0382] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.
[0383] 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.
[0384] 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.
[0385] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one or more embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.
[0386] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.
[0387] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0388] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound can each independently be selected from the oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of alkali metals, alkaline earth metals, and rare earth metals, respectively.
[0389] The alkali metal compound can be selected from alkali metal oxides (e.g., Li 2 O, Cs 2 O, and / or K 2 O) and alkali metal halides (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI). In one or more embodiments, the alkali metal compound can be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.
[0390] The alkaline earth metal compound can be selected from alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1) and / or Ba x Ca 1-x O (0 < x < 1). In one or more embodiments, the alkaline earth metal compound can be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.
[0391] The rare earth metal compound can 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 or more embodiments, the rare earth metal compound can 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.
[0392] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may contain ions of alkali metal, alkaline earth metal and rare earth metal as described above, respectively, and the ligand coordinated to the metal ion of the alkali metal complex, alkaline earth metal complex or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0393] The electron injection layer may include (e.g., be composed of) the following: 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 than one 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 a combination thereof may be uniformly or non-uniformly dispersed in a matrix comprising an organic material.
[0394] 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 above-described range, the electron injection layer may have satisfactory (or suitable) electron injection characteristics without a significant increase in driving voltage.
[0395] The second electrode 190
[0396] The second electrode 190 may be disposed on the organic layer 150 having the structure according to the embodiment of the present disclosure. 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.
[0397] 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.
[0398] The second electrode 190 may have a single-layer structure, or a multi-layer structure including two or more layers.
[0399] Figures 2 to 4 Description
[0400] Figure 2 is a schematic diagram of an organic light-emitting device 20 according to an embodiment of the present disclosure. The organic light-emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked in this prescribed order. Figure 3 is a schematic diagram of an organic light-emitting device 30 according to an embodiment of the present disclosure. 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, which are sequentially stacked in this prescribed order. Figure 4 is a schematic diagram of an organic light-emitting device 40 according to an embodiment of the present disclosure. The organic light-emitting device 40 includes a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked in this prescribed order.
[0401] about Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can be described by referring to Figure 1 Their descriptions are presented to understand.
[0402] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emission layer may pass through the first electrode 110 and the first cover layer 210 toward the outside, wherein the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the emission layer may pass through the second electrode 190 and the second cover layer 220 toward the outside, wherein the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.
[0403] The first cover layer 210 and the second cover layer 220 may increase external light emitting efficiency according to the principle of constructive interference.
[0404] 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.
[0405] At least one selected from the first cover layer 210 and the second cover layer 220 may each independently contain at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compound, heterocyclic compound, and / or amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I.
[0406] In one or more than one embodiments, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include an amine-based compound.
[0407] In one or more than one embodiments, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.
[0408] In one or more than one embodiments, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but the embodiments of the present disclosure are not limited thereto:
[0409]
[0410] In the above, it has been combined Figures 1 to 4 The organic light-emitting device according to one or more than one embodiments of the present disclosure is described, but the embodiments of the present disclosure are not limited thereto.
[0411] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be formed in a certain (set or predetermined) area using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and laser induced thermal imaging.
[0412] 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. / second to about The deposition was carried out at a deposition rate of 1.33 W / s.
[0413] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by spin coating, the spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80° C. to about 200° C. by considering the material to be included in the layer to be formed and the structure of the layer to be formed.
[0414] Display Devices
[0415] The organic light emitting device according to the present embodiment may be included in a display device including a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, and one of the source electrode and the drain electrode may be in electrical contact with a first electrode of the organic light emitting device.
[0416] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc., but embodiments of the present disclosure are not limited thereto.
[0417] General Definition of Substituents
[0418] As used herein, the term "C 1 -C 60 The term "alkyl group" may refer to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, and a hexyl group. In some embodiments, C 1 -C 60 The alkyl group may be C 1 -C 30 Alkyl group, C 1 -C 20 Alkyl group or C 1 -C 10 As used herein, the term "C 1 -C 60 "Alkylene group" may refer to a 1 -C 60 Alkyl groups are divalent groups of substantially the same structure.
[0419] As used herein, the term "C 2 -C 60 The term "alkenyl group" may refer to an 2 -C 60 At one or more than one position of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 In some embodiments, C2 -C 60 The alkenyl group may be C 2 -C 30 Alkenyl group, C 2 -C 20 Alkenyl group or C 2 -C 10 As used herein, the term "C 2 -C 60 "Alkenylene group" may refer to a 2 -C 60 Alkenyl groups are divalent groups of substantially the same structure.
[0420] As used herein, the term "C 2 -C 60 "Alkynyl group" may refer to 2 -C 60 At one or more than one position of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 The alkyl group has at least one hydrocarbon group having a carbon-carbon triple bond in the middle and / or at the terminal, and non-limiting examples thereof include an ethynyl group and a propynyl group. 2 -C 60 The alkynyl group may be C 2 -C 30 Alkynyl group, C 2 -C 20 Alkynyl group or C 2 -C 10 As used herein, the term "C 2 -C 60 "Alkyne group" may refer to a 2 -C 60 Alkynyl groups are divalent radicals of substantially the same structure.
[0421] As used herein, the term "C 1 -C 60 The term "alkoxy group" may refer to 101 (A 101 C 1 -C 60 The term "alkyl group" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.
[0422] As used herein, the term "C 3 -C 10The term "cycloalkyl group" as used herein may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. 3 -C 10 The "cycloalkylene group" may refer to a group having 3 -C 10 Cycloalkyl groups are divalent groups of substantially the same structure.
[0423] As used herein, the term "C 1 -C 10 The term “heterocycloalkyl group” may refer to a monovalent monocyclic group having at least one heteroatom (e.g., 1 to 5 or 1 to 3 atoms, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group and a tetrahydrothienyl group. As used herein, the term “C 1 -C 10 The term "heterocycloalkylene group" may refer to a 1 -C 10 Heterocycloalkyl groups are divalent groups of substantially the same structure.
[0424] The term "C 3 -C 10 The term "cycloalkenyl group" as used herein may refer 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, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 3 -C 10 The "cycloalkenylene group" may refer to a 3 -C 10 Cycloalkenyl groups are divalent groups of substantially the same structure.
[0425] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" may refer to a monovalent monocyclic group having at least one heteroatom (e.g., 1 to 5 or 1 to 3 atoms, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as a ring-forming atom, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups, and 2,3-dihydrothienyl groups. As used herein, the term “C 1 -C10 The term "heterocycloalkenylene group" may refer to a 1 -C 10 Heterocycloalkenyl groups are divalent groups of substantially the same structure.
[0426] As used herein, the term "C 6 -C 60 The term "aryl group" may refer to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups and As used herein, the term "C 6 -C 60 The term "arylene group" may refer to a 6 -C 60 In some embodiments, C 6 -C 60 The aryl group may be C 6 -C 30 Aryl group, C 6 -C 24 Aryl group or C 6 -C 18 Aryl group. When C 6 -C 60 Aryl groups and C 6 -C 60 When the arylene groups each independently include 2 or more rings, the respective rings may be fused to each other.
[0427] As used herein, the term "C 1 -C 60 The term "heteroaryl group" may refer to a monovalent group having a carbocyclic aromatic system containing at least one heteroatom (e.g., 1 to 5 or 1 to 3 atoms, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as a ring atom in addition to 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, and isoquinolyl groups. 1 -C 60 The term "heteroarylene group" may refer to a 1 -C 60In some embodiments, C 1 -C 60 The heteroaryl group may be C 1 -C 30 Heteroaryl groups, C 1 -C 24 Heteroaryl groups or C 1 -C 18 Heteroaryl group. 1 -C 60 Heteroaryl groups and C 1 -C 60 When the heteroarylene groups each independently contain two or more rings, the respective rings may be fused to each other.
[0428] As used herein, the term "C 6 -C 60 The term "aryloxy group" may refer to 102 (A 102 C 6 -C 60 aryl group), and as used herein, the term "C 6 -C 60 The "arylthio group" may refer to 103 (A 103 C 6 -C 60 A monovalent group represented by an aryl group.
[0429] As used herein, the term "monovalent non-aromatic fused polycyclic group" may refer to a monovalent group having two or more rings fused to each other, having only carbon atoms as ring atoms (e.g., having 8 to 60 carbon atoms, such as 8 to 30 or 8 to 24 carbon atoms), and having no aromaticity in its entire molecular structure. A non-limiting example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic fused polycyclic group" may refer to a divalent group having a structure substantially the same as a monovalent non-aromatic fused polycyclic group.
[0430] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" may refer to a monovalent group having two or more rings fused to each other, at least one heteroatom (e.g., 1 to 5 or 1 to 3 atoms, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as a ring-forming atom, carbon atoms (e.g., 1 to 60 carbon atoms, such as 1 to 30 or 1 to 24 carbon atoms) as the remaining ring-forming atoms, and having no aromaticity in its entire molecular structure. A non-limiting example of a monovalent non-aromatic fused heteropolycyclic group is a carbazolyl group. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" may refer to a divalent group having a structure substantially the same as a monovalent non-aromatic fused heteropolycyclic group.
[0431] As used herein, the term "C 5 -C 60 A "carbocyclic group" may refer to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. As used herein, the term "C 5 -C 60 The term "carbocyclic group" may refer to an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (e.g., benzene); a monovalent group (e.g., a phenyl group); or a divalent group (e.g., a phenylene group). In one or more than one embodiments, the carbonyl group is connected to the carbonyl group. 5 -C 60 The number of substituents in a carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group. 5 -C 60 The carbocyclic group may be C 5 -C 30 Carbocyclic group, C 5 -C 24 Carbocyclic group or C 5 -C 18 Carbocyclic group.
[0432] As used herein, the term "C 1 -C 60 A "heterocyclic group" may refer to a 5 -C 60 The carbocyclic group is a group having substantially the same structure as the carbocyclic group, but in addition to carbon atoms (the number of carbon atoms can be 1 to 60, such as 1 to 30 or 1 to 24 carbon atoms), at least one heteroatom (e.g., 1 to 5 or 1 to 3 atoms, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S is used as a ring-forming atom.
[0433] In this specification, substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 3 -C 10 Cycloalkylene groups, substituted C 1 -C 10 Heterocycloalkylene groups, substituted C 3 -C 10 Cycloalkenylene groups, substituted C 1 -C 10 Heterocycloalkenylene groups, substituted C 6 -C 60 Arylene groups, substituted C 1 -C 60 Heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 1 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C 1 -C 10 Heterocycloalkenyl groups, substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, 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 may be selected from:
[0434] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2-C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;
[0435] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl group, 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 ) at least one substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;
[0436] C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0437] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) at least one substituted C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0438] -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 ),as well as
[0439] 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heteropolycyclic groups, C substituted by at least one selected from deuterium, -F and cyano groups 1 -C 60 An alkyl group, a C substituted by at least one selected from deuterium, -F and a cyano group 6 -C 60 Aryl groups, biphenyl groups and terphenyl groups.
[0440] The term "Ph" as used herein may refer to a phenyl group, the term "Me" as used herein may refer to a methyl group, the term "Et" as used herein may refer to an ethyl group, and the terms "ter-Bu" and "Bu" as used herein may refer to a phenyl group. t " may refer to a tert-butyl group, the term "OMe" as used herein may refer to a methoxy group, and "D" may refer to deuterium.
[0441] As used herein, the term "biphenyl group" may refer to a "phenyl group substituted by a phenyl group". For example, a "biphenyl group" is a group having C 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0442] The term "terphenyl group" as used herein may refer to a "phenyl group substituted by a biphenyl group". For example, a "terphenyl group" is a phenyl group substituted by a C 6 -C 60 Aryl-substituted C 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0443] Unless otherwise defined, * and *' as used herein each refer to a site of attachment to an adjacent atom in the corresponding formula.
[0444] Hereinafter, the compound according to the embodiment of the present disclosure and the organic light-emitting device according to the embodiment of the present disclosure will be described in more detail with reference to the synthesis examples and examples. The phrase "using B to replace A" used in describing the synthesis examples may refer to using an equimolar equivalent of B to replace A.
[0445] Synthesis example
[0446] Synthesis example 1
[0447]
[0448] Synthesis of intermediate 1-1
[0449] The intermediate 1 was reacted with 1-bromo-4-fluorobenzene, CuI, K 2 CO 3and L-proline were mixed in a dimethyl sulfoxide (DMSO) solvent at a temperature of 160° C. to synthesize Intermediate 1-1. Intermediate 1-1 was identified by liquid chromatography-mass spectrometry (LC-MS).
[0450] C 12 H 9 B O 2 :M+1 263.98.
[0451] Synthesis of intermediate 1-2
[0452] The intermediate 1-1 was reacted with 1-bromo-4-fluorobenzene, CuI, K 2 CO 3 and L-proline were mixed in a DMSO solvent at a temperature of 160° C. to synthesize Intermediate 1-2. Intermediate 1-2 was identified by LC-MS.
[0453] C 18 H 12 BrF 2 :M+1 358.00.
[0454] Synthesis of intermediate 1-3
[0455] The intermediate 1-2 was reacted with furan-2,4-diyldiboronic acid, Pd 2 (dba) 3 and K 3 PO 4 In THF / H 2 O solvent at 120° C. to synthesize Intermediate 1-3. Intermediate 1-3 was identified by LC-MS.
[0456] C 40 H 28 F 2 O 5 :M+1 626.19.
[0457] Synthesis of intermediates 1-4
[0458] The intermediate 1-3 and nBuLi are reacted with each other. The mixture is heated in BBr 3 The intermediate 1-4 was activated by 4% ethyl acetate and reacted with diisopropylethylamine at 120° C. to synthesize the intermediate 1-4. The intermediate 1-4 was identified by LC-MS.
[0459] C 40 H 20 B 2 F 2 O 5 :M+1 640.23.
[0460]
[0461] Synthesis of intermediates 1-5
[0462] Intermediate 1-4 was added to pyrazole (cas: 288-13-1) and potassium carbonate and reacted with pyrazole and potassium carbonate to synthesize Intermediate 1-5. Intermediate 1-5 was identified by LC-MS.
[0463] C 46 H 26 B 2 N 4 O 5 :M+1 736.36.
[0464] Synthesis of compound BD1
[0465] Intermediate 1-5 was mixed with dichloro(1,5-cyclooctadiene)palladium(II) and sodium acetate in a dioxane solvent at a temperature of 160° C. to synthesize Compound BD1. Compound BD1 was identified by LC-MS.
[0466] C 46 H 20 B 2 N 4 O 5 Pt 2 :M+1 1120.49.
[0467] Synthesis example 2
[0468]
[0469] Synthesis of intermediate 5-5
[0470] Intermediate 1-4 was reacted with 3,5-dimethylpyrazole (cas: 67-51-6) and potassium carbonate to synthesize intermediate 5-5. Intermediate 5-5 was identified by LC-MS.
[0471] C 50 H 34 B 2 N 4 O 5 :M+1 792.47.
[0472] Synthesis of compound BD5
[0473] Intermediate 5-5 was mixed with dichloro(5,5-cyclooctadiene)palladium(II) and sodium acetate in a dioxane solvent at a temperature of 160° C. to synthesize compound BD5. Compound BD5 was identified by LC-MS.
[0474] C 50 H 28 B 2 N4 O 5 Pt 2 :M+1 1176.59.
[0475] Synthesis example 3
[0476]
[0477] Synthesis of intermediate 6-5
[0478] Intermediate 1-4 was reacted with imidazole (cas: 288-32-4) and potassium carbonate to synthesize intermediate 6-5. Intermediate 6-5 was identified by LC-MS.
[0479] C 46 H 26 B 2 N 4 O 5 :M+1 736.36.
[0480] Synthesis of intermediate 6-6
[0481] Intermediate 6-5 was reacted with iodomethane (cas: 74-88-4) and acetone as a solvent to synthesize intermediate 6-6. Intermediate 6-6 was identified by LC-MS.
[0482] C 48 H 32 B 2 N 4 O 5 :M+1 766.43
[0483] Synthesis of compound BD6
[0484] Intermediate 6-6 was mixed with dichloro(1,5-cyclooctadiene)palladium(II) and sodium acetate in a dioxane solvent at a temperature of 160° C. to synthesize compound BD6. Compound BD6 was identified by LC-MS.
[0485] C 48 H 24 B 2 N 4 O 5 Pt 2 :M+1 1148.53.
[0486] Synthesis example 4
[0487]
[0488] Synthesis of intermediate 7-5
[0489] Intermediate 1-4 was reacted with benzimidazole (cas: 51-17-2) and potassium carbonate to synthesize intermediate 7-5. Intermediate 7-5 was identified by LC-MS.
[0490] C 54 H 30 B 2 N 4 O 5 :M+1 836.48.
[0491] Synthesis of intermediate 7-6
[0492] Intermediate 7-5 was reacted with iodomethane (cas: 74-88-4) and acetone as a solvent to synthesize Intermediate 7-6. Intermediate 7-6 was identified by LC-MS.
[0493] C 56 H 36 B 2 N 4 O 5 :M+1 866.55.
[0494] Synthesis of compound BD7
[0495] Intermediate 7-6 was mixed with dichloro(1,5-cyclooctadiene)palladium(II) and sodium acetate in a dioxane solvent at a temperature of 160° C. to synthesize compound BD7. Compound BD7 was identified by LC-MS.
[0496] C 56 H 28 B 2 N 4 O 5 Pt 2 :M+1 1248.65.
[0497] Synthesis example 5
[0498]
[0499] Synthesis of intermediate 8-5
[0500] Intermediate 1-4 was reacted with N-methylimidazole (cas: 616-47-7) and potassium carbonate to synthesize intermediate 8-5. Intermediate 8-5 was identified by LC-MS.
[0501] C 48 H 30 B 2 N 4 O 5 :M+1 764.41.
[0502] Synthesis of compound BD8
[0503] Intermediate 8-5 was mixed with dichloro(1,5-cyclooctadiene)palladium(II) and sodium acetate in a dioxane solvent at a temperature of 160° C. to synthesize compound BD8. Compound BD8 was identified by LC-MS.
[0504] C 48 H 24 B 2 N 4 O 5 Pt 2 :M+1 1148.53.
[0505] The intermediate synthesis methods of compound BD1 and compound BD5 to compound BD8 can be basically applied to other compounds to synthesize other compounds of the present embodiment.
[0506] Example
[0507] Example 1
[0508] As substrate and anode, 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes.Then, the ITO glass substrate was provided to a vacuum deposition apparatus.
[0509] 2-TNATA was vacuum deposited on an ITO anode formed on an ITO glass substrate to form a A hole injection layer having a thickness of , and NPB is vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .
[0510] The co-host bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS) and (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA) (the weight ratio of BCPDS to POPCPA is 1:1) and the dopant compound BD1 are co-deposited on the hole transport layer so that the weight ratio of the co-host to the dopant is 90:10 to form a The thickness of the emission layer.
[0511] Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) is deposited on the emissive layer to form a The thickness of the hole blocking layer is Alq 3 deposited on the hole blocking layer to form a An electron transport layer having a thickness of , LiF is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form a A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[0512]
[0513] Examples 2 to 5 and Comparative Examples 1 to 3
[0514] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Example 1, except that the compounds shown in Table 1 were respectively used instead of Compound BD1 as a dopant in forming an emission layer.
[0515] Evaluation Example 1
[0516] The driving voltage, current density, brightness, luminous efficiency, emission color and maximum emission wavelength of the organic light-emitting devices manufactured according to Examples 1 to 5 and Comparative Examples 1 to 3 were measured by using Keithley SMU 236 and luminance meter PR650, and the results are shown in Table 1.
[0517] Table 1
[0518]
[0519]
[0520]
[0521] Referring to Table 1, it is confirmed that each of the organic light-emitting devices of Examples 1 to 5 has low driving voltage, high brightness, high light-emitting efficiency, and a long lifespan compared to those of the organic light-emitting devices of Comparative Examples 1 to 3.
[0522] An organic light-emitting device including an organometallic compound may have low driving voltage, high brightness, high efficiency, and a long lifetime.
[0523] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.
[0524] Furthermore, the terms "substantially," "about," and similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent variations in measurements or calculations that would be recognized by those of ordinary skill in the art.
[0525] In addition, any numerical range listed herein is intended to include all sub-ranges of the same numerical precision within the scope of the listing. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical value listed herein is intended to include all lower numerical limits included therein, and any minimum numerical value listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly list any sub-ranges included in the scope explicitly listed herein.
[0526] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
[0527] Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the claims and their equivalents.
Claims
1. An organic light-emitting device, comprising: a first electrode; a second electrode; an organic layer between the first electrode and the second electrode and including an emission layer; as well as At least one organometallic compound represented by Formula 1: Formula 1 Wherein, in Formula 1, M1 and M2 are each independently selected from the first row transition metal, the second row transition metal and the third row transition metal of the periodic table, Y1 to Y8 are each independently selected from carbon atoms and nitrogen atoms, T1 to T8 are each independently selected from a chemical bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R") and P(R')(R"), wherein when T1 is a chemical bond, Y1 and M1 are directly connected to each other, when T2 is a chemical bond, Y2 and M1 are directly connected to each other, when T3 is a chemical bond, Y3 and M1 are directly connected to each other, when T4 is a chemical bond, Y4 and M1 are directly connected to each other, when T5 is a chemical bond, Y5 and M2 are directly connected to each other, when T6 is a chemical bond, Y6 and M2 are directly connected to each other, when T7 is a chemical bond, Y7 and M2 are directly connected to each other, and when T8 is a chemical bond, Y8 and M2 are directly connected to each other, two bonds selected from the bond between Y1 or T1 and M1, the bond between Y2 or T2 and M1, the bond between Y3 or T3 and M1, and the bond between Y4 or T4 and M1 are each coordinate bonds, and the other two bonds are each covalent bonds; and two bonds selected from the bond between Y5 or T5 and M2, the bond between Y6 or T6 and M2, the bond between Y7 or T7 and M2, and the bond between Y8 or T8 and M2 are each coordinate bonds, and the other two bonds are each covalent bonds, Ring A1 is selected from a cyclopentadiene group, a furan group, a thiophene group and a pyrrole group, Ring A2 to Ring A9 are each independently selected from C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups, X1 to X4 are each independently O or S, L1 to L5 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R 10 )(R 11 )-*'、*-C(R 10 )=*'、*=C(R 10 )-*'、*-C(R 10 )=C(R 11 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 10 )-*'、*-N(R 10 )-*'、*-P(R 10 )-*'、*-Si(R 10 )(R 11 )-*'、*-P(R 10 )(R 11 )-*' and *-Ge(R 10 )(R 11 )-*', a1 to a3 are each independently selected from 0, 1, 2 and 3, wherein at least two of a1 to a3 are each independently selected from 1, 2 and 3, When a1 is 0, ring A1 and ring A2 are not connected to each other, when a2 is 0, ring A2 and ring A3 are not connected to each other, and when a3 is 0, ring A1 and ring A4 are not connected to each other, a4 and a5 are each independently selected from 1, 2 and 3, R', R" and R1 to R 11 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C1-C 60 Alkyl group, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2), b1 to b9 are each independently an integer from 1 to 20, Selected from R1 to R 11 Any two substituents in are optionally linked to each other to form a substituted or unsubstituted C5-C 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic groups, The substituted C5-C 60 Carbocyclic group, the substituted C1-C 60 Heterocyclic group, the substituted C1-C 60 Alkyl group, the substituted C2-C 60 Alkenyl group, the substituted C2-C 60 Alkynyl group, the substituted C1-C 60 Alkoxy group, the substituted C3-C 10 Cycloalkyl group, the substituted C1-C 10 Heterocycloalkyl group, the substituted C3-C 10 Cycloalkenyl group, the substituted C1-C 10 Heterocycloalkenyl group, the substituted C6-C 60 Aryl group, the substituted C6-C 60 Aryloxy group, the substituted C6-C 60 Arylthio group, the substituted C1-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: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, 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 ) at least one substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) at least one substituted C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and -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 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups, * and *' each represent a site of attachment to an adjacent atom, and B represents a boron atom, and O represents an oxygen atom.
2. The organic light emitting device according to claim 1, wherein The first electrode is an anode, The second electrode is a cathode, said organic layer comprising said at least one organometallic compound, 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 at least one layer selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer and an electron blocking layer, and The electron transport region includes at least one layer selected from the group consisting of a hole blocking layer, an electron transport layer, and an electron injection layer.
3. The organic light emitting device according to claim 2, wherein The emissive layer comprises the at least one organometallic compound.
4. The organic light emitting device according to claim 3, wherein The emission layer further comprises a host, and the at least one organometallic compound is a phosphorescent material or a delayed fluorescent material.
5. The organic light emitting device according to claim 2, wherein At least one selected from the emission layer, the hole transport region, and the electron transport region includes at least one selected from a carbazole-based compound, a silicon-based compound, a sulfur oxide, and a phosphorus oxide.
6. The organic light emitting device according to claim 2, wherein At least one selected from the hole transport region and the electron transport region comprises the at least one organometallic compound.
7. Display equipment, including: A thin film transistor including a source electrode, a drain electrode and an active layer; as well as The organic light-emitting device according to claim 1, The first electrode of the organic light-emitting device is in electrical contact with one of the source electrode and the drain electrode of the thin film transistor.
8. An organometallic compound represented by Formula 1: Formula 1 in, In Formula 1, M1 and M2 are each independently selected from the first row transition metal, the second row transition metal and the third row transition metal of the periodic table, Y1 to Y8 are each independently selected from carbon atoms and nitrogen atoms, T1 to T8 are each independently selected from a chemical bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R") and P(R')(R"), wherein when T1 is a chemical bond, Y1 and M1 are directly connected to each other, when T2 is a chemical bond, Y2 and M1 are directly connected to each other, when T3 is a chemical bond, Y3 and M1 are directly connected to each other, when T4 is a chemical bond, Y4 and M1 are directly connected to each other, when T5 is a chemical bond, Y5 and M2 are directly connected to each other, when T6 is a chemical bond, Y6 and M2 are directly connected to each other, when T7 is a chemical bond, Y7 and M2 are directly connected to each other, and when T8 is a chemical bond, Y8 and M2 are directly connected to each other, two bonds selected from the bond between Y1 or T1 and M1, the bond between Y2 or T2 and M1, the bond between Y3 or T3 and M1, and the bond between Y4 or T4 and M1 are each coordinate bonds, and the other two bonds are each covalent bonds; and two bonds selected from the bond between Y5 or T5 and M2, the bond between Y6 or T6 and M2, the bond between Y7 or T7 and M2, and the bond between Y8 or T8 and M2 are each coordinate bonds, and the other two bonds are each covalent bonds, Ring A1 is selected from a cyclopentadiene group, a furan group, a thiophene group and a pyrrole group, Ring A2 to Ring A9 are each independently selected from C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups, X1 to X4 are each independently O or S, L1 to L5 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R 10 )(R 11 )-*'、*-C(R 10 )=*'、*=C(R 10 )-*'、*-C(R 10 )=C(R 11 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 10 )-*'、*-N(R 10 )-*'、*-P(R 10 )-*'、*-Si(R 10 )(R 11 )-*'、*-P(R 10 )(R 11 )-*' and *-Ge(R 10 )(R 11 )-*', a1 to a3 are each independently selected from 0, 1, 2 and 3, wherein at least two of a1 to a3 are each independently selected from 1, 2 and 3, When a1 is 0, ring A1 and ring A2 are not connected to each other, when a2 is 0, ring A2 and ring A3 are not connected to each other, and when a3 is 0, ring A1 and ring A4 are not connected to each other, a4 and a5 are each independently selected from 1, 2 and 3, R', R" and R1 to R 11 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C1-C 60 Alkyl group, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2), b1 to b9 are each independently an integer from 1 to 20, Selected from R1 to R 11 Any two substituents in are optionally linked to each other to form a substituted or unsubstituted C5-C 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic groups, The substituted C5-C 60 Carbocyclic group, the substituted C1-C 60 Heterocyclic group, the substituted C1-C 60 Alkyl group, the substituted C2-C 60 Alkenyl group, the substituted C2-C 60 Alkynyl group, the substituted C1-C 60 Alkoxy group, the substituted C3-C 10 Cycloalkyl group, the substituted C1-C 10 Heterocycloalkyl group, the substituted C3-C 10 Cycloalkenyl group, the substituted C1-C 10 Heterocycloalkenyl group, the substituted C6-C 60 Aryl group, the substituted C6-C 60 Aryloxy group, the substituted C6-C 60 Arylthio group, the substituted C1-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: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, 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 ) at least one substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) at least one substituted C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and -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 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups, * and *' each represent a site of attachment to an adjacent atom, and B represents a boron atom, and O represents an oxygen atom.
9. The organometallic compound according to claim 8, wherein M1 and M2 in Formula 1 are each independently selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru and Os.
10. The organometallic compound according to claim 8, wherein In formula 1, T1 to T4 are each chemical bonds, At least one bond selected from the bond between Y1 and M1 and the bond between Y2 and M1 is a coordination bond, Y1 is C, and Y2 is C or N, T5 to T8 are each chemical bonds, At least one bond selected from the bond between Y5 and M2 and the bond between Y8 and M2 is a coordination bond, Y5 is C, and Y8 is C or N.
11. The organometallic compound according to claim 8, wherein In Formula 1, Y3 and Y4 are each C, and Y6 and Y7 are each C.
12. The organometallic compound according to claim 8, wherein Ring A2 to Ring A9 in Formula 1 are each independently selected from a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a 1,2,4-triazole group, a tetrazole group, an azathiole group, a diazathiole group, a triazathiole group, a benzimidazole group, an imidazopyridine group, an imidazopyrazine group, a cyclohexane group and a cyclohexene group.
13. The organometallic compound according to claim 8, wherein Ring A2 and Ring A8 are each independently selected from a pyrazole group, an imidazole group, a benzimidazole group, an imidazopyridine group and an imidazopyrazine group, and Ring A3 to Ring A7 and Ring A9 are each independently a benzene group.
14. The organometallic compound according to claim 8, wherein Ring A1 in Formula 1 is a group represented by Formula 2-1: Formula 2-1 in, In formula 2-1, Y 21 C(R 21 )(R 22 )、N(R 21 ), O or S, R 21 and R 22 Each independently relates to R', R" and R1 to R in Formula 1 11 Same as described, and * indicates a bonding site with T1, *' indicates a bonding site with L3, *" indicates a bonding site with T5, and *"' indicates a bonding site with L4.
15. The organometallic compound according to claim 8, wherein Ring A2 and Ring A8 in Formula 1 are each independently a group represented by one of Formulas 2-2(1) to 2-2(4): in, In equations 2-2(1) to 2-2(4), Y 21 N or C (R 21 ), Y 22 N or C (R 22 ), Y 23 N or C (R 23 ), and Y 24 N or C (R 24 ), R 21 To R 25 Each independently relates to R', R" and R1 to R in Formula 1 11 Same as described, and * indicates the connection site between loop A2 and T2 or the connection site between loop A8 and T8, and *' indicates the connection site between loop A2 and L2 or the connection site between loop A8 and L5.
16. The organometallic compound according to claim 8, wherein i) X1 to X4 are each O, ii) X1 to X4 are each S, or iii) X1 and X2 are each O, and X3 and X4 are each S.
17. The organometallic compound according to claim 8, wherein a1 is 0, a2 to a5 are each 1, and L2 to L5 are each a single bond.
18. The organometallic compound according to claim 8, wherein R', R" and R1 to R 11 Each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups and C1-C 20 Alkoxy groups; Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 20 Alkyl groups and C1-C 20 At least one of the alkoxy groups is substituted with a C1-C 20 Alkyl groups and C1-C 20 Alkoxy groups; a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group; and Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 20 Alkyl groups, C1-C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group and triazinyl group; and -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), and Q1 to Q3 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a C1-C 20 Alkyl groups, C2-C 20 Alkenyl groups, C2-C 20 Alkynyl group, C1-C 20 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 20 Aryl group, C1-C 20 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups.
19. The organometallic compound according to claim 8, wherein The organic metal compound represented by Formula 1 is represented by Formula 1-1: Formula 1-1 in, In formula 1-1, M1, M2, Ring A1 to Ring A9, Y1 to Y8, L2 to L5, X1 to X4, R1 to R9 and b1 to b9 are each independently the same as described about Formula 1.
20. The organometallic compound according to claim 8, wherein The organometallic compound represented by Formula 1 is selected from Compound BD1 to Compound BD96:
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