Organic light emitting device
By using two host materials and two dopants with specific energy relationships in the design of organic light-emitting devices, the problem of short device lifetime caused by TADF materials was solved, and long life and stability of the device were achieved.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2020-03-31
- Publication Date
- 2026-03-17
AI Technical Summary
Existing organic light-emitting devices have a short lifespan, especially when using thermally activated delayed fluorescence (TADF) materials, due to device degradation caused by the instability of triplet excitons.
A fluorescent emission layer design incorporating two types of host materials, one TADF dopant, and one fluorescent dopant is employed. By satisfying specific singlet and triplet energy relationship equations, the quenching of triplet excitons is controlled, preventing device degradation.
It significantly extends the lifespan of organic light-emitting devices and improves their stability and durability.
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Figure CN112086582B_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2019-0070073, filed with the Korean Intellectual Property Office on June 13, 2019, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more embodiments of this disclosure relate to organic light-emitting devices. Background Technology
[0004] Organic light-emitting devices are self-emitting devices that produce full-color images. Compared with other light-emitting devices, they have wide viewing angles, high contrast, short response times, and superior characteristics in terms of brightness, driving voltage, and response speed.
[0005] An organic light-emitting device may include a first electrode on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes supplied by the first electrode can move through the hole transport region to the emitter layer, and electrons supplied by the second electrode can move through the electron transport region to the emitter layer. Charge carriers (e.g., holes and electrons) recombine in the emitter layer to generate excitons. The excitons then transition from an excited state to a ground state (e.g., transition or relaxation), thereby generating light. Summary of the Invention
[0006] One or more embodiments of this disclosure provide an organic light-emitting device with a long lifespan compared to other light-emitting devices in the art.
[0007] Other aspects of the implementation scheme will be set forth in part in the following description, and will become apparent in part from the description, or may be learned by practice of the presented implementation scheme.
[0008] The embodiments of this disclosure provide an organic light-emitting device, including:
[0009] First electrode;
[0010] The second electrode facing the first electrode; and
[0011] An organic layer comprising a fluorescence emitting layer is located between the first electrode and the second electrode.
[0012] The fluorescent emitting layer comprises a first host H1, a second host H2, a first dopant D1, and a second dopant D2, and
[0013] The singlet energy (S1(H1)) of the first host, the triplet energy (T1(H1)) of the first host, the singlet energy (S1(H2)) of the second host, the triplet energy (T1(H2)) of the second host, the singlet energy (S1(D1)) of the first dopant, the triplet energy (T1(D1)) of the first dopant, the singlet energy (S1(D2)) of the second dopant, and the triplet energy (T1(D2)) of the second dopant satisfy the following equations (1) to (7):
[0014] S1(H1)>S1(D1) (1)
[0015] S1(H2)>S1(D1) (2)
[0016] T1(H1)>T1(D1) (3)
[0017] T1(H2)>T1(D1) (4)
[0018] S1(D1)–T1(D1)≤0.3eV (5)
[0019] S1(D1)–S1(D2)≤0.2eV (6)
[0020] T1(D1)>T1(D2) (7).
[0021] Another aspect of the implementation of this disclosure provides an electronic device, including:
[0022] Thin-film transistors; and
[0023] The organic light-emitting device
[0024] The thin-film transistor includes a source electrode, a drain electrode, an active layer, and a gate electrode, and 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. Attached Figure Description
[0025] These and / or other aspects of the embodiments will become apparent and more readily understood from the following description of the embodiments in conjunction with the accompanying drawings, in which:
[0026] Figures 1 to 4 Each is a schematic diagram of the structure of an organic light-emitting device according to the implementation plan. Detailed Implementation
[0027] Reference will now be made to the embodiments in more detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this respect, the present embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, only embodiments are described below with reference to the accompanying drawings to explain aspects of the embodiments currently described. As used herein, the term “and / or” includes any combination and all combinations of one or more of the items in the relevant list. Expressions such as “at least one” modify the entire column of elements when preceding a column of elements, without modifying any individual element in that column.
[0028] The organic light-emitting device according to the embodiment includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, including a fluorescent emitting layer.
[0029] The fluorescent emitting layer comprises a first host H1, a second host H2, a first dopant D1, and a second dopant D2, and
[0030] The singlet state energies (S1(H1)) of the first host, the triplet state energies (T1(H1)) of the first host, the singlet state energies (S1(H2)) of the second host, the triplet state energies (T1(H2)) of the second host, the singlet state energies (S1(D1)) of the first dopant, the triplet state energies (T1(D1)) of the first dopant, the singlet state energies (S1(D2)) of the second dopant, and the triplet state energies (T1(D2)) of the second dopant satisfy the following equations (1) to (7):
[0031] S1(H1)>S1(D1) (1)
[0032] S1(H2)>S1(D1) (2)
[0033] T1(H1)>T1(D1) (3)
[0034] T1(H2)>T1(D1) (4)
[0035] S1(D1)–T1(D1)≤0.3eV (5)
[0036] S1(D1)–S1(D2)≤0.2eV (6)
[0037] T1(D1)>T1(D2) (7).
[0038] In one implementation, the first host H1, the second host H2, the first dopant D1, and the second dopant D2 can be different materials.
[0039] Since the first reported device with an external quantum efficiency of approximately 1% in 1989 (CWTang, SAVan Slyke, CH Chen, J. Appl. Phys. 1989, 65, 3610), numerous organic light-emitting diodes (OLEDs) have been researched and industrialized. Since 2010, OLEDs have replaced LCDs in small panels in the display market where liquid crystal displays (LCDs) were once dominant.
[0040] Regarding the light emission mechanism of OLEDs, luminescent materials are classified into fluorescent (e.g., phosphorescent) materials and phosphorescent (e.g., phosphorescent) materials based on their light emission mechanism. Phosphors (e.g., phosphorescent materials) with theoretical internal quantum efficiencies of up to 100% have attracted attention as high-efficiency OLED emitters. However, these phosphors have short lifespans and include expensive transition metals and lanthanides, leading to heavy atom effects. Many research teams in industry and academia are conducting studies to investigate these issues.
[0041] Recently, Adachi's team at Kyushu University in Japan realized an OLED device using thermally activated delayed fluorescence (TADF), and reportedly achieved an internal quantum efficiency of 96.5% and an external quantum efficiency of 19.3% using fluorescence. The TADF phenomenon is a method that enables 75% of triplet excitons to be used for fluorescence by minimizing or reducing the difference between the singlet and triplet energy levels of the emitter, thereby activating reverse system crossing (RISC) at room temperature without heavy atoms. Therefore, the TADF phenomenon is a mechanism that can achieve 100% internal quantum efficiency.
[0042] In cases where a TADF material (e.g., a first dopant D1) is used as a luminescent material according to one or more embodiments, when the RISC rate is slow or uneven, the triplet excitons of the TADF material (first dopant D1) are controlled by additionally including a second dopant D2 as a fluorescent material to prevent or reduce the reduction in lifetime caused by the formation or decay of triplet excitons, thereby improving lifetime characteristics.
[0043] In the TADF system, room-temperature energy is used in materials with a very small energy difference between the singlet and triplet states, causing RISC to occur from the triplet state to the singlet state with higher energy, and exhibiting delayed fluorescence when the singlet state transitions (e.g., transitions) to the ground state.
[0044] However, TADF materials with a relatively long exciton lifetime can maintain the triplet state for extended periods, for example, when RISC rates are slow or RISC occurs unevenly. Therefore, the device's lifespan can be shortened due to device degradation or material degradation.
[0045] According to an embodiment of this disclosure, the triplet state of the TADF material is quenched to the triplet state of another material with lower energy to prevent or reduce degradation, thereby increasing the lifespan of the device.
[0046] The inventors of this disclosure have discovered through numerous experiments that when a TADF system includes two types of host H1 and host H2 and includes one type of TADF material D1 as a dopant and one type of general fluorescent dopant D2 other than TADF material, and the relationship between the singlet energy and triplet energy of these materials satisfies equations (1) to (7), the lifetime is significantly improved compared to existing TADF systems.
[0047] In one embodiment, the organic light-emitting device may be a thermally activated delayed fluorescence (TADF) organic light-emitting device.
[0048] In one embodiment, the fluorescent emitting layer may comprise (or be substantially composed of, or consist of) a first host H1, a second host H2, a first dopant D1, and a second dopant D2. For example, the fluorescent emitting layer may be substantially composed of the first host H1, the second host H2, the first dopant D1, and the second dopant D2, such that other emitting materials, if present, are only incidental impurities in the fluorescent emitting layer.
[0049] In one embodiment, the fluorescent emitting layer may not contain transition metals. For example, the fluorescent emitting layer may be substantially free of transition metals, so that if any, the transition metals present in the fluorescent emitting layer are only as incidental impurities. In some embodiments, the fluorescent emitting layer is completely free of transition metals.
[0050] In one implementation, the first dopant D1 may be a TADF material.
[0051] In one embodiment, the second dopant D2 can be a general fluorescent dopant other than the TADF material. A general fluorescent dopant is a fluorescent dopant in which the energy difference between the singlet and triplet states is greater than 0.3 eV.
[0052] The singlet energy (S1(D2)) of the second dopant and the triplet energy (T1(D2)) of the second dopant can satisfy equation (8):
[0053] S1(D2)–T1(D2)>0.3eV (8).
[0054] When the difference between the singlet energy (S1(D2)) and the triplet energy (T1(D2)) of the second dopant is 0.3 eV or less, the triplet energy (T1(D2)) of the second dopant is high, and therefore, the triplet energy (T1(D1)) of the first dopant cannot be quenched smoothly.
[0055] In one implementation, the second dopant D2 in the triplet energy (T1) state quenches the first dopant D1 in the triplet energy (T1) state.
[0056] Quenching refers to the transition (e.g., a jump) from the high triplet energy (T1) of the first dopant D1 to the low triplet energy (T1) of the second dopant D2, thus escaping the unstable state and transitioning to a relatively more stable state. The energy transferred to the triplet energy (T1) of the second dopant D2 disappears and is not involved in light emission. This disappearance can occur through the rotational and / or vibrational energies of the individual molecules.
[0057] In one embodiment, the weight ratio of the first body H1 to the second body H2 can be from about 6:4 to about 4:6. When the weight ratio of the first body H1 to the second body H2 is less than 6:4 or greater than 4:6, the service life of the device is not significantly improved.
[0058] In one embodiment, based on 100 parts by weight of the first body H1 and the second body H2, the amount of the first dopant D1 can be from about 1 part by weight to about 50 parts by weight, and based on 100 parts by weight of the first dopant D1, the amount of the second dopant D2 can be from about 0.1 parts by weight to about 50 parts by weight.
[0059] When the amount of the first dopant D1 is less than or equal to 1 part by weight or greater than 50 parts by weight based on 100 parts by weight of the first host H1 and the second host H2, the lifespan of the device is not significantly improved. When the amount of the second dopant D2 is less than or equal to 0.1 parts by weight or greater than 50 parts by weight based on 100 parts by weight of the first dopant D1, the lifespan of the device is not significantly improved.
[0060] In one embodiment, based on 100 parts by weight of the first body H1 and the second body H2, the amount of the first dopant D1 can be from about 1 part by weight to about 6 parts by weight, and based on 100 parts by weight of the first dopant D1, the amount of the second dopant D2 can be from about 5 parts by weight to about 15 parts by weight. For example, based on 100 parts by weight of the first body H1 and the second body H2, the amount of the first dopant D1 can be from about 2 parts by weight to about 4 parts by weight, and based on 100 parts by weight of the first dopant D1, the amount of the second dopant D2 can be from about 8 parts by weight to about 12 parts by weight.
[0061] In one embodiment, the first subject H1 and the second subject H2 may each be independently selected from the following compounds (e.g., compounds 1 to 13), but the embodiments of this disclosure are not limited thereto. The selected first subject H1 and the selected second subject H2 may be different compounds.
[0062]
[0063]
[0064] In one embodiment, the first dopant D1 may include any of the following:
[0065]
[0066]
[0067] As used herein, the expression "the first dopant D1 includes any of the portions" can include cases where "the first dopant D1 includes the portion itself as is", cases where a particular first dopant D1 compound may include substituents defined herein in the portion that simultaneously include portions 1 to 38, and cases where a particular first dopant D1 compound may include multiple portions.
[0068] In one embodiment, the first dopant D1 may be selected from the following compounds:
[0069]
[0070]
[0071] In one embodiment, the second dopant D2 can be a compound represented by Formula 1 or Formula 2:
[0072] Formula 1
[0073]
[0074] Formula 2
[0075]
[0076] In Equations 1 and 2,
[0077] Ar1 and Ar2 can be independently selected from substituted or unsubstituted C6-C. 60 aryl groups and substituted or unsubstituted C1-C 60 heteroaryl groups,
[0078] R1 to R8 and R 11 To R14 Each can be independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 60 Alkyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0079] L1 and L2 can be independently selected from substituted or unsubstituted C6-C. 60 arylene groups and substituted or unsubstituted C1-C 60 heteroaryl groups,
[0080] i and j can each be 0 or 1 independently.
[0081] The substituted C1-C 60 alkyl groups, the substituted C6-C 60 aryl group, the substituted C1-C 60 Heteroaryl groups, the substituted monovalent non-aromatic fused polycyclic groups, the substituted monovalent non-aromatic fused heterocyclic groups, the substituted C6-C 60 arylene groups and the substituted C1-C 60 At least one substituent of the heteroaryl group may be selected from:
[0082] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine 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 group;
[0083] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 group;
[0084] C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;
[0085] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; and
[0086] -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
[0087] Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl groups, and terphenyl groups.
[0088] In one implementation, X in Equation 2 can be selected from Equations 2a to 2e:
[0089]
[0090] In equations 2a to 2e,
[0091] R 21 To R 28 Each can be independently selected from hydrogen, deuterium, and C1-C. 60 Alkyl groups, C6-C 60 aryl group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups.
[0092] R 22 and R 23 They can be connected to each other to form a ring.
[0093] Y1 and Y2 can each be O or S independently.
[0094] a21 and a24 through a28 can each be an integer from 1 to 4 independently, and
[0095] * indicates a connection site with an adjacent atom.
[0096] In one embodiment, the second dopant D2 may be selected from the following compounds:
[0097]
[0098]
[0099]
[0100]
[0101]
[0102]
[0103]
[0104]
[0105]
[0106]
[0107] As used herein, the statement “(organic layer) contains at least one compound represented by Formula 1” can include cases where “(organic layer) contains the same compound represented by Formula 1” and cases where “(organic layer) contains two or more different compounds represented by Formula 1”.
[0108] For example, the organic layer may contain only compound 1 as a compound. In this respect, compound 1 may be present only in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may contain both compound 1 and compound 2 as compounds. In one or more embodiments, compound 1 and compound 2 may both be present in the same layer (e.g., compound 1 and compound 2 may both be present in the emitting layer), or they may be present in different layers (e.g., compound 1 may be present in the emitting layer, and compound 2 may be present in the electron transport region).
[0109] In one implementation scheme
[0110] The first electrode of an organic light-emitting device can be the anode.
[0111] The second electrode of an organic light-emitting device can be a cathode, and
[0112] The organic layer may further include a hole transport region between the first electrode and the emitter layer and an electron transport region between the emitter layer and the second electrode.
[0113] As used herein, the term "organic layer" refers to a single layer and / or multiple layers between the first and second electrodes of an organic light-emitting device. The materials contained in the "organic layer" are not limited to organic materials. For example, the organic layer may contain inorganic materials.
[0114] Figure 1 Description
[0115] Figure 1 This is a cross-sectional schematic diagram of the organic light-emitting device 10 according to the embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0116] In the following text, we will combine Figure 1 Describes the structure of an organic light-emitting device according to an embodiment and the method of manufacturing an organic light-emitting device according to an embodiment.
[0117] First electrode 110
[0118] exist Figure 1In this configuration, the substrate may additionally be located below the first electrode 110 or above the second electrode 190. For use as a substrate, the substrate may be a glass substrate or a plastic substrate, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0119] The first electrode 110 can 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 used to form the first electrode 110 can be selected from materials with high work function to facilitate hole injection.
[0120] The first electrode 110 can be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-reflective electrode or a reflective electrode, the material used to form the first electrode can 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 this disclosure are not limited thereto.
[0121] 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 to this.
[0122] Organic layer 150
[0123] The organic layer 150 is on the first electrode 110. The organic layer 150 may include an emitter layer.
[0124] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 190.
[0125] Hole transport region in organic layer 150
[0126] The hole transport region may have i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.
[0127] The hole transport region may include at least one layer selected from the hole injection layer, hole transport layer, emission assist layer and electron blocking layer.
[0128] For example, the hole transport region may have a single-layer structure comprising a single layer containing multiple different materials, or a multi-layer structure, wherein the multi-layer structure has a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein for each structure, the constituent layers are stacked sequentially from the first electrode 110 in this prescribed order, but the structure of the hole transport region is not limited to this.
[0129] The hole transport region may contain at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by formula 201, and compounds represented by formula 202.
[0130]
[0131]
[0132] Formula 201
[0133]
[0134] Formula 202
[0135]
[0136] In equations 201 and 202,
[0137] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0138] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 alkylene groups, substituted or unsubstituted C2-C 20 alkenyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0139] xa1 to xa4 can each be an integer from 0 to 3 independently.
[0140] xa5 can be an integer from 1 to 10, and
[0141] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0142] For example, in equation 202, R 201 and R 202 They can optionally be linked to each other via single bonds, dimethyl-methylene groups, or diphenyl-methylene groups, and R 203 and R 204 They can be optionally linked together via single bonds, dimethyl-methylene groups, or diphenyl-methylene groups.
[0143] In one implementation, in formulas 201 and 202,
[0144] L 201 To L 205 Each can be selected independently from:
[0145] Phenylidene group, pentylene group, indenyl group, naphthyl group, chamomile cycloyl group, heptylene group, adamantyl group, acenaphthene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthroline group, anthracene group, fluorenyl group, benzo[a]phenanthrene group, pyrene group, etc. Benzyl group, tetraphenyl group, puryl group, peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rubidyl group, styrenyl group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophenyl group and pyridylyl group; and
[0146] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, pyridyl group, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31(Q) 32 At least one substituted phenylene group, pentylene group, indenyl group, naphthyl group, chamomile cycloyl group, heptylene group, adamantyl group, acenaphthene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenenthene group, anthracene group, fluorenyl group, benzo[a]phenanthrene group, pyrene group, etc. The following groups are listed: alkyl group, tetraphenylene group, purylene group, perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, rubidium benzoate group, styrenyl group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophenyl group, and pyridylene group.
[0147] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.
[0148] In one or more implementations, xa1 to xa4 can each be 0, 1 or 2 independently.
[0149] In one or more implementations, xa5 can be 1, 2, 3 or 4.
[0150] In one or more implementations, R 201 To R 204 and Q 201 Each can be selected independently from:
[0151] Phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, heptenyl group, indoleyl group, acenaphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthreneyl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthreneyl group, pyrene group, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group and pyridyl group; and
[0152] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, pyridyl group, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 At least one substituted phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, heptenyl group, indoleyl group, acenaphthenic group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthreneyl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthreneyl group, pyreneyl group, The following groups are listed: alkyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, thiophenyl group, furanyl group, carbazoleyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, dibenzothiophenyl group, and pyridyl group.
[0153] Q 31 To Q 33 Same as described above.
[0154] In one or more embodiments, R selected from Formula 201 201 To R 203 At least one of them can be independently selected from:
[0155] Fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group; and
[0156] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 At least one substituted fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group, and dibenzothiophene group selected from the following groups: alkyl-substituted phenyl group, -F-substituted phenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, carbazole group, dibenzofuranyl group, and dibenzothiophene group.
[0157] However, the implementation of this disclosure is not limited to this.
[0158] In one or more implementations, in formula 202, i)R 201 and R 202 They can be connected to each other via a single key, and / or ii)R 203 and R 204 They can be connected to each other via a single key.
[0159] In one or more embodiments, R selected from Formula 202 201 To R 204 At least one of them can be selected from:
[0160] Carbazolium group; and
[0161] Selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 At least one substituted carbazoyl group selected from the following groups: alkyl-substituted phenyl group, -F-substituted phenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, carbazoyl group, dibenzofuranyl group, and dibenzothiophenyl group.
[0162] However, the implementation of this disclosure is not limited to this.
[0163] The compound represented by formula 201 can be represented by the following formula 201A:
[0164] Formula 201A
[0165]
[0166] In one embodiment, the compound represented by formula 201 may be represented by the following formula 201A(1), but the embodiments of this disclosure are not limited thereto:
[0167] Formula 201A(1)
[0168]
[0169] In one or more embodiments, the compound represented by formula 201 may be represented by the following formula 201A-1, but the embodiments of this disclosure are not limited thereto:
[0170] Formula 201A-1
[0171]
[0172] In one embodiment, the compound represented by formula 202 may be represented by the following formula 202A, but the embodiments of this disclosure are not limited thereto:
[0173] Formula 202A
[0174]
[0175] In one or more embodiments, the compound represented by formula 202 may be represented by the following formula 202A-1, but the embodiments of this disclosure are not limited thereto:
[0176] Formula 202A-1
[0177]
[0178] In Equations 201A, 201A(1), 201A-1, 202A, and 202A-1,
[0179] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 As described above,
[0180] R 211 and R 212 You can refer to this article about R 203 To understand, and
[0181] R 213 To R 217 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Alkyl-substituted phenyl groups, -F-substituted phenyl groups, pentanenyl groups, indole groups, naphthyl groups, chamomile cycloyl groups, heptenyl groups, indoleyl groups, acenaphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthrenyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, The group includes benzo[a], tetraphenyl[b], furan[b], peryl[b], pentaphenyl[a], hexaphenyl[b], pentaphenyl[a], rutin[b], koj[b], ovoid[b], thiophen[b], furan[b], carbazo[b], indole[b], isoindole[b], benzofuran[b], benzothiophen[b], dibenzofuran[b], dibenzothiophen[b], benzocarbazo[b], dibenzocarbazo[b], dibenzothiophen[b], dibenzothiophen[b], and pyridyl[b]
[0182] The hole transport region may contain at least one compound selected from compounds HT1 to HT39, but embodiments of this disclosure are not limited thereto:
[0183]
[0184]
[0185]
[0186] The thickness of the hole transport region can be approximately to approximately For example, about to approximately When the hole transport region includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer can be approximately to approximately For example, about to approximately And the thickness of the hole transport layer can be approximately to approximately For example, about to approximately
[0187] The emission assist layer can increase light emission efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assist layer and the electron blocking layer can contain materials as described above.
[0188] p-dopants
[0189] In addition to these materials, the hole transport region may further contain charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.
[0190] The charge-generating material can be, for example, a p-doped agent.
[0191] In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of about -3.5 eV or less than -3.5 eV.
[0192] p-dopers may include at least one selected from quinone derivatives, metal oxides, and compounds containing cyano groups, but embodiments of this disclosure are not limited thereto.
[0193] In one embodiment, the p-doper may include at least one selected from the following:
[0194] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);
[0195] Metal oxides, such as tungsten oxide or molybdenum oxide;
[0196] 1,4,5,8,9,12-hexaazatriphenylene-hexacarbamate (HAT-CN); and
[0197] The compound represented by formula 221,
[0198] However, the implementation of this disclosure is not limited to this:
[0199]
[0200] Equation 221
[0201]
[0202] In Equation 221,
[0203] R 221 To R 223 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, and substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, wherein the group selected from R 221 To R 223 At least one of them may have a C1-C group selected from cyano group, -F, -Cl, -Br, -I, or a C1-C group substituted with -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and C1-C substituted with -I 20 At least one substituent in an alkyl group.
[0204] Emission layer in organic layer 150
[0205] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, or a blue emitting layer, depending on the sub-pixel. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers are in contact with or spaced apart from each other. In one or more embodiments, the emitting layer may contain two or more materials selected from red-emitting, green-emitting, and blue-emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0206] The emitter layer may include a first body H1, a second body H2, a first dopant D1, and a second dopant D2, according to the implementation scheme.
[0207] In addition to the first body H1, the second body H2, the first dopant D1, and the second dopant D2 according to the embodiment, the emitter layer may further comprise a body and dopants. The dopants may include at least one selected from phosphorescent dopants and fluorescent dopants.
[0208] In the emitter layer, based on 100 parts by weight of the host, the amount of dopant can typically be from about 0.01 parts by weight to about 15 parts by weight, but the embodiments of this disclosure are not limited thereto.
[0209] The thickness of the emission layer can be approximately to approximately For example, about to approximately When the thickness of the emitter layer is within this range, excellent emission characteristics can be obtained without a significant increase in the driving voltage.
[0210] The main body in the emission layer
[0211] The main body may contain compounds according to the implementation scheme.
[0212] In addition to the compounds according to the embodiments, the body may include compounds represented by the following formula 301:
[0213] Formula 301
[0214] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0215] In Equation 301,
[0216] Ar 301 C5-C can be substituted or unsubstituted. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0217] xb11 can be 0, 1, 2, or 3.
[0218] L 301 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.
[0219] xb1 can be an integer from 0 to 5.
[0220] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C. 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -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 ),
[0221] xb21 can be an integer from 1 to 5, and
[0222] Q 301 To Q 303 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but embodiments of this disclosure are not limited thereto.
[0223] In one implementation, Ar in Formula 301 301 You can choose from:
[0224] Naphthalene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl groups, furan groups, perylene groups, pentaphenyl groups, indene-anthracene groups, dibenzofuran groups, and dibenzothiophene groups; and
[0225] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-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 At least one substituted naphthyl group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenatene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl groups, furan groups, perylene groups, pentaphenyl groups, indene-anthracene groups, dibenzofuran groups, and dibenzothiophene groups, and
[0226] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups,
[0227] However, the implementation of this disclosure is not limited to this.
[0228] In Equation 301, when xb11 is 2 or greater than 2, there are two or more Ar... 301 It can be connected via a single key.
[0229] In one or more embodiments, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:
[0230] Formula 301-1
[0231]
[0232] Formula 301-2
[0233]
[0234] In Equations 301-1 and 301-2,
[0235] Ring A 301 To Ring A 304 Each ring can be independently selected from benzene ring, naphthalene ring, phenanthrene ring, fluoranthene ring, benzo[a]phenanthrene ring, pyrene ring, etc. Rings, pyridine rings, pyrimidine rings, indene rings, fluorene rings, spiro-difluorene rings, benzo[a]fluorene rings, dibenzo[a]fluorene rings, indole rings, carbazole rings, benzo[a]carbazole rings, dibenzo[a]carbazole rings, furan rings, benzo[a]furan rings, dibenzo[a]furan rings, naphtho[a]furan rings, benzo[a]naphtho[a]furan rings, dinaphtho[a]furan rings, thiophene rings, benzo[a]thiophene rings, dibenzo[a]thiophene rings, naphtho[a]thiophene rings, benzo[a]naphtho[a]thiophene rings, and dinaphtho[a]thiophene rings.
[0236] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0237] R 311 To R 314 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-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 ),
[0238] xb22 and xb23 can each be 0, 1, or 2 independently.
[0239] L 301 xb1, R 301 and Q 31 To Q 33 As described above,
[0240] L 302 To L 304 They can be independently related to L 301 The same definition
[0241] xb2 to xb4 can each be independently identical to the definition of xb1, and
[0242] R 302 To R 304 They can be independently related to R. 301 The definitions are the same.
[0243] For example, in Equations 301, 301-1, and 301-2, L 301 To L 304 Each can be selected independently from:
[0244] Phenylidene group, naphthyl group, fluorenelidene group, spiro-difluorenelidene group, benzo[a]fluorenelidene group, dibenzo[a]fluorenelidene group, phenanthrenelidene group, anthracenelidene group, fluorenethracene group, benzo[a]phenanthrenelidene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group , pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzoquinolineyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group; and
[0245] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl 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 At least one substituted phenylene group, naphthylene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluorenyl anthracene group, benzo[a]phenanthrene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group The following groups are listed: pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzo[a]quinolineyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group.
[0246] Q 31 To Q 33 Same as described above.
[0247] In one implementation, R in Formulas 301, 301-1, and 301-2 301 To R 304 Each can be selected independently from:
[0248] Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthryl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group; and
[0249] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl 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 At least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthryl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group, and
[0250] Q 31 To Q 33 Same as described above.
[0251] In one embodiment, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55), Mg complexes, and Zn complexes.
[0252] In one or more embodiments, the main body may include at least one selected from 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP) and compounds H1 to H55, but embodiments of this disclosure are not limited thereto:
[0253]
[0254]
[0255]
[0256] Phosphorescent dopants contained in the emission layer of organic layer 150
[0257] Phosphorescent dopants may include organometallic complexes represented by the following formula 401:
[0258] Formula 401
[0259] M(L 401 ) xc1 (L 402 ) xc2
[0260] Formula 402
[0261]
[0262] In Equations 401 and 402,
[0263] M can 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).
[0264] L 401 The ligand can be represented by the free formula 402, and xc1 can be 1, 2, or 3. When xc1 is two or more, there are two or more L... 401 They can be the same or different from each other.
[0265] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, wherein when xc2 is two or greater than two, there are two or more L... 402 They can be the same or different from each other.
[0266] X 401 To X 404 They can be nitrogen or carbon independently.
[0267] X 401 and X 403 It can be connected via a single or double key, and X 402 and X 404 It can be connected via a single key or a double key.
[0268] A 401 and A 402 Each can be independently selected from C5-C. 60 Carbocyclic groups and C1-C60 Heterocyclic groups,
[0269] 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 They can each be independently hydrogen, deuterium, or C1-C. 20 Alkyl groups, C1-C 20 alkoxy group, phenyl group, biphenyl group, triphenyl group or naphthyl group,
[0270] X 406 It can be a single bond, O, or S.
[0271] R 401 and R 402 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C groups. 20 Alkyl groups, substituted or unsubstituted C1-C 20 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic 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 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 alkoxy group, C6-C 20 aryl groups and C1-C 20 heteroaryl groups,
[0272] xc11 and xc12 can each be an integer from 0 to 10 independently, and
[0273] In Equation 402, * and *' each represent the connection site with M in Equation 401.
[0274] In one implementation, A in Formula 402 401 and A 402 Each group can be independently selected from phenyl groups, naphthyl groups, fluorene groups, spiro-difluorene groups, indene groups, pyrrole groups, thiophene groups, furan groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, quinoxaloline groups, quinazoline groups, carbazole groups, benzimidazole groups, benzofuran groups, benzothiophene groups, isobenzothiophene groups, benzooxazole groups, isobenzooxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, dibenzofuran groups, and dibenzothiophene groups.
[0275] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 Each can be nitrogen at the same time.
[0276] In one or more embodiments, R in Formula 402 401 and R 402 Each can be selected independently from:
[0277] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 alkyl groups and C1-C 20 alkoxy group;
[0278] Each of the C1-C groups is substituted with at least one of the following groups: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidoyl group, hydrazine group, hydrazone group, phenyl group, naphthyl group, cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, and norbornylene group. 20 alkyl groups and C1-C 20 alkoxy group;
[0279] Cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, norbornyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group, dibenzofuranyl group and dibenzothiophenyl group;
[0280] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 At least one substituted cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group, dibenzofuranyl group, and dibenzothiophenyl group; and
[0281] -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
[0282] Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, and naphthyl groups, but embodiments of the present disclosure are not limited thereto.
[0283] In one or more embodiments, in formula 401, when xc1 is 2 or greater than 2, two or more L 401 The two A's in 401 It can be optionally via X as a linking group 407 Two A's are connected to each other, or when xc1 is 2 or greater than 2. 402 It can be optionally via X as a linking group 408 They are interconnected (see compounds PD1 through PD4 and PD7). X 407 and X 408 Each can be independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q)-*', or *-N(Q)-*'. 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 They can each be independently hydrogen, deuterium, or C1-C. 20 Alkyl groups, C1-C 20 (Alkoxy group, phenyl group, biphenyl group, terphenyl group or naphthyl group), but the embodiments of this disclosure are not limited thereto.
[0284] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The compounds may be selected from halogens, diketones (e.g., acetylacetonates), carboxylic acids (e.g., pyridine carboxylates), -C (=O), isonitriles, -CN, and phosphorus compounds (e.g., phosphine or phosphite esters), but embodiments of this disclosure are not limited thereto.
[0285] In one or more embodiments, the phosphorescent dopant may be selected, for example, from compound PD1 to compound PD25, but the embodiments of this disclosure are not limited thereto:
[0286]
[0287]
[0288] Fluorescent dopants in the emission layer
[0289] Fluorescent dopants can include styrene-based amine compounds, etc.
[0290] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments disclosed herein are not limited to these:
[0291]
[0292] Electron transport region in organic layer 150
[0293] The electron transport region may have i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.
[0294] 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 this disclosure are not limited thereto.
[0295] For example, the electron transport region can have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein for each structure, the constituent layers are stacked sequentially from the emitter layer. However, the implementation scheme of the electron transport region structure is not limited to this.
[0296] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may contain a metal-free compound with a nitrogen-containing ring that has at least one π electron depleted.
[0297] As used herein, the term "π-electron depleted nitrogen-containing ring" refers to a C1-C ring having at least one *-N=*' moiety as a cyclic component. 60 Heterocyclic groups.
[0298] For example, a "π-electron depleted nitrogen-containing ring" can be i) a 5- to 7-membered heterocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group wherein two or more 5- to 7-membered heterocyclic groups each having at least one *-N=*' moiety are fused together, or iii) at least one of the 5- to 7-membered heterocyclic groups each having at least one *-N=*' moiety is combined with at least one C5-C 60 A heterocyclic group with fused carbocyclic groups.
[0299] Examples of nitrogen-containing rings that are depleted of π electrons include, but are not limited to, imidazoles, pyrazoles, thiazoles, isothiazoles, oxazoles, isoxazoles, pyridines, pyrazines, pyrimidines, pyridazines, indazoles, purines, quinoline, isoquinoline, benzoquinoline, phthalazines, naphthidine, quinoxaline, quinazoline, cyclophosphine, phenanthridine, acridine, phenanthridine, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazoles, tetraazoles, oxadiazoles, triazines, thiadiazoles, imidazopyridines, imidazopyrimidines, and azacarbazoles.
[0300] For example, the electron transport region may contain a compound represented by the following formula 601:
[0301] Formula 601
[0302] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0303] In Equation 601,
[0304] Ar 601 C5-C can be substituted or unsubstituted. 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0305] xe11 can be 1, 2, or 3.
[0306] L 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups and substituted or unsubstituted divalent nonaromatic fused heterocyclic groups;
[0307] xe1 can be an integer from 0 to 5.
[0308] R 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0309] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, or naphthyl groups, and
[0310] xe21 can be an integer from 1 to 5.
[0311] In one implementation, xe11 quantity of Ar 601 and the number of R in xe21 601 At least one of them may contain a nitrogen-containing ring that has depleted π electrons.
[0312] In one implementation, Ar in Formula 601 601 You can choose from:
[0313] Phenyl group, naphthyl group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl group, styrene group, perylene group, pentaphenyl group, indene-anthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazolinoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacarbazole group; and
[0314] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-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 At least one substituted phenyl group, naphthyl group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Groups, tetraphenyl, styrene, perylene, pentaphenyl, indene-anthracene, dibenzofuran, dibenzothiophene, carbazole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthidine, quinoxaline, quinazolin, cinnamic acid, phenanthridine, acridine, phenanthrene-rhein, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetraazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, and
[0315] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.
[0316] When xe11 in equation 601 is 2 or greater than 2, there are two or more Ar... 601 They can be connected to each other via a single key.
[0317] In one or more embodiments, Ar in Formula 601 601 It can be an anthracene group.
[0318] In one or more embodiments, the compound represented by formula 601 can be represented by the following formula 601-1:
[0319] Formula 601-1
[0320]
[0321] In Equation 601-1,
[0322] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and selected from X 614 To X 616 At least one of them can be N,
[0323] L 611 To L 613 They can be independently related to L 601 The same definition
[0324] xe611 to xe613 can each be independently identical to the definition regarding xe1.
[0325] R 611 To R 613 They can be independently related to R. 601 The same definition, and
[0326] R 614 To R 616 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.
[0327] In one implementation, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Each can be selected independently from:
[0328] Phenylidene group, naphthyl group, fluorenelidene group, spiro-difluorenelidene group, benzo[a]fluorenelidene group, dibenzo[a]fluorenelidene group, phenanthrenelidene group, anthracenelidene group, fluorenethracene group, benzo[a]phenanthrenelidene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group , pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzoquinolineyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group; and
[0329] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinoline At least one substituted phenylene group, naphthidyl group, quinoxalinyl group, quinazolinyl group, phenanthrynyl group, acridineyl group, phenanthrolineyl group, phenazinyl group, benzimidazole group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazole group, tetrazolyl group, imidazopyridyl group, imidazopyrimidyl group, and azacarbazolyl group, naphthylene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthrene group, anthracene group, fluorenyl anthracene group, benzo[a]phenanthrene group, pyrene group, etc., selected from the following groups: phenylene group, naphthylene group, naphthylene group, benzo[a]phenanthrene group, pyrene group, etc. Perylene group, pentaphenylene group, hexaphenylene group, pentaphenylene group, thiophene group, furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzothiophene group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiazolyl diazolyl group, oxadiazolyl group The following groups are listed: pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolineyl group, isoquinolineyl group, benzo[a]quinolineyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinoxalinyl group, phenanthrene-pyridinyl group, acridineyl group, phenanthrene-pyridinyl group, benzimidazoleyl group, isobenzothiazolyl group, benzimidazoleyl group, isobenzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and zazacarbazolyl group.
[0330] However, the implementation of this disclosure is not limited to this.
[0331] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each be 0, 1 or 2 independently.
[0332] In one or more embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Each can be selected independently from:
[0333] Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthryl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridinyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Groups, including pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group;
[0334] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, benzo[a]phenanthrene group, pyrene group, Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinoline The following groups are substituted with at least one of the following groups: phthalazinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, phenanthrynyl group, acridineyl group, phenanthrolineyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridyl group, imidazopyrimidyl group, and azacarbazolyl group; a substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[fluorenyl]fluorenyl group, dibenzo[fluorenyl]fluorenyl group, phenanthrene group, anthraceneyl group, fluoranthraceneyl group, benzo[phenanthreneyl]pyrene group. Peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, thiophene group, furanyl group, carbazole group, indole group, isoindole group, benzofuranyl group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzothiophene group, pyridyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group Pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphridinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, phenanthridineyl group, acridineyl group, phenanthroxolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group; and
[0335] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),as well as
[0336] Q 601 and Q 602 Same as described above.
[0337] The electron transport region may contain at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:
[0338]
[0339]
[0340]
[0341] In one or more embodiments, the electron transport region may comprise at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ.
[0342]
[0343] In one embodiment, the electron transport region may contain a phosphine oxide-containing compound (e.g., TSPO1, etc.), but embodiments of this disclosure are not limited thereto. In one embodiment, the phosphine oxide-containing compound may be used in a hole-blocking layer within the electron transport region, but embodiments of this disclosure are not limited thereto.
[0344] The thicknesses of the buffer layer, hole blocking layer, and electronic control layer can each be approximately [missing information]. to approximately For example, about to approximately When the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are within these ranges, the hole blocking layer or electronic control layer can have excellent hole blocking or electronic control characteristics without a significant increase in driving voltage.
[0345] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately When the thickness of the electron transport layer is within the range described above, the electron transport layer can have suitable or satisfactory electron transport characteristics without a significant increase in driving voltage.
[0346] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further contain metallic materials.
[0347] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may contain metal ions selected from Li, Na, K, Rb, and Cs ions, while alkaline earth metal complexes may contain metal ions selected from Be, Mg, Ca, Sr, and Ba ions. The ligand coordinating with the metal ion of the alkali metal or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but embodiments of this disclosure are not limited thereto.
[0348] For example, metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium hydroxyquinoline, LiQ) or ET-D2:
[0349]
[0350] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0351] The electron injection layer can have i) a single-layer structure comprising a single layer containing a single material, ii) a single-layer structure comprising a single layer containing multiple different materials, or iii) a multi-layer structure comprising multiple layers containing multiple different materials.
[0352] The electron injection layer may contain alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.
[0353] The alkali metal can be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal can be Li, Na, or Cs. In one or more embodiments, the alkali metal can be Li or Cs, but the embodiments of this disclosure are not limited thereto.
[0354] Alkaline earth metals can be selected from Mg, Ca, Sr and Ba.
[0355] Rare earth metals can be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0356] Alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides of alkali metals, alkaline earth metals, and rare earth metals (e.g., fluorides, chlorides, bromides, or iodides).
[0357] The alkali metal compound can be selected from alkali metal oxides (such as Li2O, Cs2O or K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI or KI). In one embodiment, the alkali metal compound can be selected from LiF, Li2O, NaF, LiI, NaI, CsI and KI, but the embodiments of the present disclosure are not limited thereto.
[0358] The alkaline earth metal compound can be selected from alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (where 0 < x < 1) or Ba x Ca 1-x O (where 0 < x < 1). In one embodiment, the alkaline earth metal compound can be selected from BaO, SrO and CaO, but the embodiments of the present disclosure are not limited thereto.
[0359] The rare earth metal compound can be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3 and TbF3. In one embodiment, the rare earth metal compound can be selected from YbF3, ScF3, TbF3, YbI3, ScI3 and TbI3, but the embodiments of the present disclosure are not limited thereto.
[0360] The alkali metal complex, alkaline earth metal complex and rare earth metal complex can contain ions of alkali metal, alkaline earth metal and rare earth metal as described above herein, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex or rare earth metal complex can be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0361] The electron injection layer can be composed of: alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof as described above herein. In one or more embodiments, the electron injection layer can further contain an organic material. When the electron injection layer further contains an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in the matrix containing the organic material.
[0362] The thickness of the electron injection layer can be about to about For example, about to approximately When the thickness of the electron injection layer is within the range described above, the electron injection layer can have suitable or satisfactory electron injection characteristics without a significant increase in driving voltage.
[0363] Second electrode 190
[0364] The second electrode 190 may be on the organic layer 150 having such a structure. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this respect, the material used to form the second electrode 190 may be selected from metals, alloys, conductive compounds and combinations thereof having relatively low work function.
[0365] The second electrode 190 may contain at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but embodiments of this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0366] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0367] Figures 2 to 4 Description
[0368] Figure 2 This is a schematic diagram of an organic light-emitting device 20 according to an embodiment. The organic light-emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are stacked sequentially in this prescribed order. Figure 3 This is a schematic diagram of an organic light-emitting device 30 according to an embodiment. The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are stacked sequentially in this prescribed order. Figure 4 This is a schematic diagram of an organic light-emitting device 40 according to an embodiment. The organic light-emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are stacked sequentially in this prescribed order.
[0369] about Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can be referenced from the relevant information. Figure 1 Use the presented description to understand.
[0370] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emitting layer can pass outward through the first electrode 110 and the first capping layer 210, wherein the first electrode 110 can be a semi-transparent 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 emitting layer can pass outward through the second electrode 190 and the second capping layer 220, wherein the second electrode 190 can be a semi-transparent electrode or a transmissive electrode.
[0371] The first capping layer 210 and the second capping layer 220 can increase the external luminescence efficiency according to the principle of constructive interference.
[0372] The first capping layer 210 and the second capping layer 220 can each independently be an organic capping layer containing organic materials, an inorganic capping layer containing inorganic materials, or a composite capping layer containing both organic and inorganic materials. The organic capping layer can contain polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acryloyl-based resins (e.g., polymethyl methacrylate, polyacrylic acid, etc.), or any combination thereof.
[0373] At least one of the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthylphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine-based compounds may optionally be substituted with substituents containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine-based compound.
[0374] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently contain a compound represented by formula 201 or a compound represented by formula 202.
[0375] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently comprise a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but the embodiments of this disclosure are not limited thereto:
[0376]
[0377] In the above text, it has already been combined Figures 1 to 4An organic light-emitting device according to an embodiment is described, but the embodiments of this disclosure are not limited thereto.
[0378] The layers constituting the hole transport region, the emission layer, and the electron transport region can be formed in a region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0379] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are formed by vacuum deposition, by considering the materials to be included in the layers to be formed and the structure of the layers to be formed, deposition temperatures of approximately 100°C to approximately 500°C and approximately 10 -8 To about 10 -3 The vacuum degree and about / seconds to approximately Deposition was carried out at a deposition rate of / second.
[0380] When the layer constituting the hole transport region, the emitter layer, and the layer constituting the electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C, taking into account the material to be included in the layer to be formed and the structure of the layer to be formed.
[0381] equipment
[0382] Organic light-emitting devices can be included in a variety of suitable devices. For example, light-emitting devices, verification devices, and / or electronic devices that include organic light-emitting devices can be provided.
[0383] In addition to organic light-emitting devices, the light-emitting device may further include a thin-film transistor (TFT), which includes a source electrode and a drain electrode. One of the source and drain electrodes of the TFT may be in electrical contact with one of the first and second electrodes of the organic light-emitting device. The light-emitting device can be used as a variety of suitable displays, light sources, etc.
[0384] Verification devices can be, for example, biometric verification devices used to verify an individual by using biometric information from a biometric body (e.g., fingertip, pupil, etc.).
[0385] In addition to organic light-emitting devices, verification equipment may further include biometric information collectors.
[0386] Electronic devices can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasound diagnostic devices, or endoscopic displays), fish finders, various suitable measuring instruments, meters (e.g., instruments for vehicles, aircraft, and ships), projectors, etc., but embodiments of this disclosure are not limited thereto.
[0387] General definition of at least some of the substituents
[0388] As used in this article, the term "C1-C" 60 "alkyl group" refers to a straight-chain or branched monovalent group of an aliphatic saturated hydrocarbon having 1 to 60 carbon atoms, and examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl groups. In some embodiments, C1-C 60 The alkyl group can be C1-C 30 Alkyl groups, C1-C 20 alkyl groups or C1-C 10 Alkyl groups. As used herein, the term "C1-C" refers to... 60 "alkylene group" refers to a group that has a C1-C2 bond structure. 60 Alkyl groups are divalent groups with essentially the same structure.
[0389] As used in this article, the term "C2-C" 60 "Alkenyl group" refers to the group located at C2-C. 60 The alkyl group has at least one carbon-carbon double bond in the main chain (e.g., in the middle) or at the terminal end (e.g., at the end), and examples include vinyl groups, propenyl groups, and butenyl groups. In some embodiments, C2-C 60 The alkenyl group can be C2-C 30 alkenyl groups, C2-C 20 alkenyl groups or C2-C 10 Alkenyl group. As used herein, the term "C2-C" refers to an alkenyl group. 60 "Ideinyl group" refers to a group that has a C2-C... 60 Alkenyl groups are divalent groups with essentially the same structure.
[0390] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group located at C2-C. 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond in the main chain (e.g., in the middle) or at the terminal end (e.g., at the end), and examples include ethynyl and propynyl groups. In some embodiments, C2-C60 The alkynyl group can be C2-C 30 alkynyl group, C2-C 20 alkynyl group or C2-C 10 Alkynyl group. As used herein, the term "C2-C" refers to an alkynyl group. 60 "Imyynyl group" refers to a group that has a C2-C... 60 The alkynyl group is a divalent group with essentially the same structure as the alkynyl group.
[0391] As used in this article, the term "C1-C" 60 "Alkoxy group" refers to the group consisting of -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and examples of them include methoxy groups, ethoxy groups and isopropoxy groups.
[0392] As used in this article, the term "C3-C" 10 "Cycloalkyl group" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups. As used herein, the term "C3-C" is used in conjunction with "cycloalkyl group". 10 "Cycloalkylene group" refers to a group that has a C3-C6 bond structure. 10 Cycloalkyl groups are divalent groups with essentially the same structure.
[0393] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom (e.g., 1 to 6 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) and 1 to 10 carbon atoms, and examples include 1,2,3,4-oxatriazole alkyl groups, tetrahydrofuranyl groups, and tetrahydrothiophenyl groups. As used herein, the term "C1-C" is used in conjunction with other terms. 10 "Heterocyclic alkyl groups" refers to groups with C1-C2 groups. 10 Heterocyclic alkyl groups are divalent groups with essentially the same structure.
[0394] As used in this article, the term "C3-C" 10 "Cycloalenyl group" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and lacking aromaticity (e.g., the group is not aromatic), and examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. As used herein, the term "C3-C" is used in conjunction with other terms. 10 "Iridyl group" refers to a group that has a C3-C6 bond structure. 10 Cycloalkenyl groups are divalent groups with essentially the same structure.
[0395] As used in this article, the term "C1-C" 10 A "heterocyclic alkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as cyclic atoms (e.g., 1 to 6 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms), 1 to 10 carbon atoms, and at least one carbon double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl groups. As used herein, the term "C1-C" is used in conjunction with other terms. 10 "Heterocyclic alkenyl group" refers to a group that has a C1-C2 bond structure. 10 Heterocyclic alkenyl groups are divalent groups with essentially the same structure.
[0396] As used in this article, the term "C6-C" 60 "Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the C6-C group used in this article... 60 A aryl group is a divalent group that has a carbocyclic aromatic system containing 6 to 60 carbon atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, pyrene groups, and... Base group. In some embodiments, C6-C 60 The aryl group can be C6-C 30 aryl group, C6-C 24 aryl group or C6-C 18 Aryl group. When C6-C 60 aryl groups and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together (e.g., joined together).
[0397] As used in this article, the term "C1-C" 60 "Heteroaryl group" refers to a monovalent group having a carbocyclic aromatic system containing at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom other than 1 to 60 carbon atoms (e.g., 1 to 6 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms). As used herein, the term "C1-C" is used in conjunction with "C1-C". 60 "Hypo-aryl group" refers to a divalent group in a carbocyclic aromatic system containing at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom, excluding 1 to 60 carbon atoms. C1-C 60Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. In some embodiments, C1-C 60 The heteroaryl group can be C1-C 30 heteroaryl groups, C1-C 24 heteroaryl groups or C1-C 18 heteroaryl groups. When C1-C 60 heteroaryl groups and C1-C 60 When each of the heteroaryl groups comprises two or more rings, the rings may be fused together (e.g., joined together).
[0398] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl groups), and the C6-C used in this article 60 Aryl thio group represents -SA 103 (where A) 103 For C6-C 60 (aryl group).
[0399] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms, such as 8 to 30 or 8 to 20 carbon atoms) having two or more rings fused together (e.g., bonded together), having only carbon atoms as cyclic atoms, and lacking aromaticity throughout its molecular structure (e.g., the entire molecular structure is not aromatic). An example of a monovalent nonaromatic fused polycyclic group is a fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused polycyclic group.
[0400] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms, such as 1 to 30 or 1 to 20 carbon atoms) having two or more rings fused together (e.g., bonded together), having at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 6 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) as cyclic atoms, and not being aromatic throughout its molecular structure (e.g., the entire molecular structure is not aromatic). An example of a monovalent nonaromatic fused heterocyclic group is a carbazolyl group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.
[0401] As used in this article, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the cyclic atom is only a carbon atom. As used herein, the term "C5-C" is used in conjunction with other terms. 60 "Carbocyclic group" refers to either an aromatic carbocyclic group or a non-aromatic carbocyclic group. C5-C 60 The carbocyclic group can be a ring, such as benzene; a monovalent group, such as a phenyl group; or a divalent group, such as a phenylene group. In some embodiments, C5-C 60 The carbocyclic group can be C5-C 30 Carbocyclic groups, C5-C 20 Carbocyclic groups or C5-C 12 Carbocyclic group. In one or more embodiments, according to the linkage to C5-C 60 The number of substituents in the carbocyclic group, C5-C 60 The carbon ring group can be a trivalent group or a tetravalent group.
[0402] As used in this article, the term "C1-C" 60 "Heterocyclic group" refers to a group that has a cyclic structure similar to C5-C6. 60 A group with a substantially similar structure to a carbocyclic group, but in addition to carbon (the number of carbon atoms can be 1 to 60, for example 1 to 30, 1 to 20 or 1 to 12), it uses at least one heteroatom selected from N, O, Si, P and S (e.g., 1 to 6 or 1 to 3 heteroatoms, such as 1, 2, 3, 4 or 5 heteroatoms) as the cyclic atom.
[0403] In this specification, C5-C is replaced. 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkylene groups, substituted C1-C 10 Heterocyclic alkenyl groups, substituted C6-C 60 arylene groups, substituted C1-C 60 Heteroaryl groups, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl groups, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocyclic alkenyl groups, substituted C6-C 60 aryl group, substituted C6-C 60 aryloxy groups, substituted C6-C 60 aryl thiols, substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent nonaromatic fused polycyclic group, and the substituted monovalent nonaromatic fused heterocyclic group may be selected from:
[0404] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine 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 group;
[0405] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 group;
[0406] C3-C10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups;
[0407] Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups; and
[0408] -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
[0409] Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 Aryl group, C1-C 60 A heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heterocyclic group, a C1-C group substituted with at least one of deuterium, -F and cyano groups. 60 The alkyl group is a C6-C group substituted with at least one of a deuterium, -F, or cyano group. 60 Aryl groups, biphenyl groups, and terphenyl groups.
[0410] As used herein, the term "Ph" refers to a phenyl group; as used herein, the term "Me" refers to a methyl group; as used herein, the term "Et" refers to an ethyl group; and as used herein, the terms "ter-Bu" or "Bu" refer to... t "" refers to the tert-butyl group, and as used herein, the term "OMe" refers to the methyl methacrylate group.
[0411] As used herein, the term "biphenyl group" refers to "a phenyl group substituted with a phenyl group." In other words, "biphenyl group" is a group having a C6-C bond. 60 The aryl group is a substituted phenyl group.
[0412] As used herein, the term "terphenyl group" refers to "a phenyl group substituted with a biphenyl group." In other words, "terphenyl group" is a phenyl group having a C6-C substituted structure. 60 C6-C substituted with aryl group 60 The aryl group is a substituted phenyl group.
[0413] As used herein, * and *', unless otherwise defined, each refer to the connection site with the adjacent atom in the corresponding formula.
[0414] In the following description, the compounds and organic light-emitting devices according to the embodiments will be described in more detail with reference to the embodiments. The phrase "using B instead of A" as used in the description of the embodiments means using an equimolar amount of B instead of A.
[0415] Example
[0416] Energy level measurement of compounds
[0417] The energy levels in Table 1 were obtained through simulation, under the following conditions.
[0418] Time-dependent density functional theory (TD DFT); B3LYP / 6-31G* (calculated using B3LYP mixed functionals and 6-31G* basis sets) TD = (50-50, Nstates = 3)
[0419] The singlet and triplet energies of compounds 3 and 4 as the main components, compounds 203, 205, 207 and 218 as the first dopant D1, and compound 407 as the second dopant D2 were measured, and the results are shown in Table 1.
[0420] Table 1
[0421]
[0422]
[0423] As can be seen from Table 1, the relationship between the singlet and triplet energies of the compounds satisfies equations (1) to (8).
[0424] Manufacturing of organic light-emitting devices
[0425] Example 1
[0426] As the anode, Corning 15Ω / cm 2 ( The ITO glass substrate was cut to a size of 50mm × 50mm × 0.7mm, ultrasonically treated with isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The ITO glass substrate was then fed into a vacuum deposition apparatus.
[0427] HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarboxynitrile) was vacuum-deposited on an ITO glass substrate to form a hole injection layer with a thickness of 10 nm. A hole transport compound, NPB (N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)benzidine), was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 40 nm. TrisPCz (9,9′,9″-triphenyl-9H,9′H,9″H-3,3′:6′3″-tetracarbazole) was deposited on the hole transport layer to form an electron blocking layer with a thickness of 10 nm.
[0428] Compounds 3, 4, 203 and 407 were co-deposited on an electron blocking layer to form an emission layer with a thickness of 25 nm (the ratio of compound 3 to compound 4 was 5:5, compound 203 was 3% by weight of compound 3 and compound 4, and compound 407 was 10% by weight of compound 203).
[0429] Next, mCBT (9,9′-(2,8-dibenzothiophenediyl)bis-9H-carbazole) was deposited to form a hole-blocking layer with a thickness of 10 nm, and BByTP (2,7-bis(2,2′-bipyridin-5-yl)benzophenanthrene) was deposited on the hole-blocking layer to form an electron transport layer with a thickness of 40 nm. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm, and Al was deposited on the electron injection layer to form a cathode with a thickness of 100 nm, thus completing the fabrication of the organic light-emitting device. A Suicel plus 200 (manufactured by Sunic System Co., Ltd.) was used as the deposition equipment.
[0430]
[0431] Example 2
[0432] The organic light-emitting device was manufactured in essentially the same manner as in Example 1, but compound 205 was used instead of compound 203 to form the emission layer.
[0433] Example 3
[0434] The organic light-emitting device was manufactured in essentially the same manner as in Example 1, but compound 207 was used instead of compound 203 to form the emission layer.
[0435] Example 4
[0436] The organic light-emitting device was manufactured in essentially the same manner as in Example 1, but compound 218 was used instead of compound 203 to form the emission layer.
[0437] Comparative Example 1
[0438] The organic light-emitting device was manufactured in essentially the same manner as in Example 1, but without using compound 407 to form the emission layer.
[0439] Comparative Example 2
[0440] The organic light-emitting device was manufactured in essentially the same manner as in Example 2, but compound 407 was not used to form the emission layer.
[0441] Comparative Example 3
[0442] The organic light-emitting device was manufactured in essentially the same manner as in Example 3, but without using compound 407 to form the emission layer.
[0443] Comparative Example 4
[0444] The organic light-emitting device was manufactured in essentially the same manner as in Example 4, but compound 407 was not used to form the emission layer.
[0445] Comparative Example 5
[0446] The organic light-emitting device was manufactured in essentially the same manner as in Example 1, but without using compound 4 to form the emission layer (compound 203 was 3% by weight of compound 3).
[0447] Comparative Example 6
[0448] The organic light-emitting device was manufactured in essentially the same manner as in Example 1, but without using compound 3 to form the emission layer (compound 203 was 3% by weight of compound 4).
[0449] The driving voltage, external quantum efficiency, color coordinates, and lifetime of the organic light-emitting devices manufactured according to Examples 1 to 4 and Comparative Examples 1 to 6 were measured, and the results are shown in Table 2.
[0450] [Table 2]
[0451]
[0452]
[0453] As can be seen from Table 2, compared with the organic light-emitting devices of Comparative Examples 1 to 4, which did not use fluorescent dopants, and the organic light-emitting devices of Comparative Examples 5 and 6, which used only one type of host, the organic light-emitting devices of Examples 1 to 4 exhibited excellent lifespan characteristics.
[0454] Compared with existing organic light-emitting devices, organic light-emitting devices according to one or more embodiments can achieve the effect of increasing lifespan.
[0455] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The descriptions of features or aspects within each embodiment should be considered applicable to other similar features or aspects in other embodiments.
[0456] It should be understood that although the terms “first,” “second,” “third,” etc., may be used herein to describe various elements, components, areas, layers, and / or parts, these elements, components, areas, layers, and / or parts should not be limited by these terms. These terms are used to distinguish one element, component, area, layer, or part from another element, component, area, layer, or part. Therefore, without departing from the spirit and scope of this disclosure, the first element, component, area, layer, or part described above may be referred to as the second element, component, area, layer, or part.
[0457] For ease of explanation, spatial relative terms such as “below,” “under,” “below,” “below,” “above,” and “upper” may be used herein to describe the relationship of one element or feature to another, as illustrated in the accompanying drawings. It should be understood that, in addition to the directions described in the drawings, spatial relative terms are intended to cover different orientations of the device in use or operation. For example, if the device in the drawings is flipped, an element described as “below,” “below,” or “below” other elements or features would be positioned “above” other elements or features. Thus, the exemplary terms “below” and “below” can cover both the upper and lower orientations. The device may be positioned in other ways (e.g., rotated 90 degrees or in other orientations), and the spatial relative descriptors used herein should be interpreted accordingly.
[0458] It should be understood that when a component or layer is referred to as being "on," "connected to," or "attached to" another component or layer, it may be directly on, directly connected to, or directly attached to another component or layer, or there may be one or more intermediate components or layers. Furthermore, it should be understood that when a component or layer is referred to as being "between" two components or layers, it may be the only component or layer between the two components or layers, or there may be one or more intermediate components or layers.
[0459] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of this disclosure. As used herein, the singular forms “a(a)” and “an(an)” are intended to also include the plural forms unless the context clearly indicates otherwise. It should also be understood that the terms “comprise,” “comprising,” “include,” and “including,” when used in this specification, specify the presence of a defined feature, integer, behavior, operation, element, and / or component, but do not exclude the presence or addition of one or more other features, integers, behaviors, operations, elements, components, and / or groups thereof.
[0460] As used herein, the terms “substantially,” “about,” and similar terms are used as terms of approximation rather than terms of degree, and are intended to explain inherent biases in measured or calculated values that would be recognized by those skilled in the art. Furthermore, the use of “may” when describing embodiments of this disclosure means “one or more embodiments of this disclosure.” As used herein, the terms “use,” “using,” and “used” are to be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively. Additionally, the term “exemplary” is intended to refer to an instance or illustration.
[0461] Furthermore, any numerical ranges listed herein are intended to include all subranges of the same numerical precision falling within the listed range. For example, the range “1.0 to 10.0” is intended to include all subranges between the listed minimum value of 1.0 and the listed maximum value of 10.0 (and inclusive), i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit listed in this specification is intended to include all higher numerical limits falling within it. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly list any subranges falling within the scope expressly listed herein.
[0462] Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made herein without departing from the spirit and scope of the disclosure as defined by the claims and their equivalents.
Claims
1.An organic light emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and comprising a fluorescent emission layer, wherein the fluorescent emission layer comprises a first host H1, a second host H2, a first dopant D1, and a second dopant D2, and a singlet energy of the first host S1(H1), a triplet energy of the first host T1(H1), a singlet energy of the second host S1(H2), a triplet energy of the second host T1(H2), a singlet energy of the first dopant S1(D1), a triplet energy of the first dopant T1(D1), a singlet energy of the second dopant S1(D2), and a triplet energy of the second dopant T1(D2) satisfy equations (1) to (8): S1(H1) > S1(D1) (1) S1(H2) > S1(D1) (2) T1(H1) > T1(D1) (3) T1(H2) > T1(D1) (4) S1(D1) - T1(D1) ≤ 0.3 eV (5) S1(D1) - S1(D2) ≤ 0.2 eV (6) T1(D1) > T1(D2) (7) S1(D2) - T1(D2) > 0.3 eV (8), wherein the first dopant D1 is a thermally activated delayed fluorescence (TADF) material, and the second dopant D2 is a general fluorescent dopant other than the thermally activated delayed fluorescence (TADF) material, wherein the second dopant D2 in a triplet energy T1 state quenches the first dopant D1 in a triplet energy T1 state, wherein the first host H1 and the second host H2 are each independently selected from the following compounds: wherein the first dopant D1 is a compound comprising any one of the following moieties: , wherein the second dopant D2 is a compound represented by formula 1 or formula 2: , <Formula 1> <Formula 2> wherein, in formula 1 and formula 2, , i and j are each independently 0 or 1, Ar1and Ar2are each independently selected from the group consisting of substituted or unsubstituted C6-Ci0aryl groups, 60 substituted or unsubstituted C1-C6alkyl groups, and 60 substituted or unsubstituted C1-C6alkyl groups, and R1to R8and R 11 to R 14 each independently is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, L1 and L2 are each independently selected from substituted or unsubstituted C6-C. 60 arylene groups and substituted or unsubstituted C1-C 60 heteroaryl groups, 2.The organic light emitting device of claim 1, wherein, said substituted C1-C 60 alkyl group, said substituted C6-C 60 aryl group, said substituted C1-C 60 heteroaryl group, said substituted monovalent non-aromatic fused polycyclic group, said substituted monovalent non-aromatic fused heteropolycyclic group, said substituted C6-C 60 arylene group, and said substituted C1-C 60 heteroarylene group are selected from the group consisting of: deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a guanyl group, a hydrazine group, a hydrazone group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group and a C1-C 60 alkoxy group; Each group is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 group; C3-C 10 cycloalkyl groups, C1-C 10 heterocycloalkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 heterocycloalkenyl groups, C6-C 60 aryl groups, C6-C 60 aryloxy groups, C6-C 60 arylthio groups, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups; each is selected from the group consisting of deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a guanyl group, a hydrazine group, a hydrazone group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=0)(Q 21 ), -S(=0)2(Q 21 ), and -P(=0)(Q 21 )(Q 22 ) substituted C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=0)(Q 31 ), -S(=0)2(Q 31 ), and -P(=0)(Q 31 )(Q 32 ), and Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl groups, and terphenyl groups. the first dopant D1 is selected from the following compounds: 3.The organic light emitting device of claim 1, wherein, 。 X in formula 2 is selected from formula 2a to formula 2e: wherein, in formula 2a to formula 2e, , Y1 and Y2 are each independently O or S, R 21 to R 28 each independently is selected from the group consisting of hydrogen, deuterium, C1-C 60 alkyl group, C6-C 60 aryl group, C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, R 22 and R 23 are optionally connected to each other to form a ring, a21 and a24 to a28 are each independently an integer of 1 to 4, and 4.The organic light emitting device of claim 1, wherein, represents the point of attachment to the adjacent atom. the second dopant D2 is selected from the following compounds: 。
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