Organic light emitting device and apparatus including the same
By using combinations of compounds with different HOMO and LUMO energy levels to form excitocomplexes in organic light-emitting devices, the problems of insufficient driving voltage and efficiency in existing technologies have been solved, realizing organic light-emitting devices with low driving voltage, high efficiency and long lifetime.
Patent Information
- Application Number
- CN202110201913.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-04-02
- Filing Date
- 2021-02-23
- Publication Date
- 2025-11-07
- Estimated Expiration
- 2041-02-23
AI Technical Summary
Existing organic light-emitting devices have shortcomings in terms of driving voltage, efficiency, and lifespan, making it difficult to meet the requirements of high-performance displays.
Two compounds containing different HOMO and LUMO energy levels are used to form an excitocomplex, which is then combined with a dopant to form an organic layer that improves carrier injection efficiency and exciton formation efficiency, reduces driving voltage, and increases efficiency.
This has enabled the development of organic light-emitting devices with low driving voltage, high efficiency, and long lifespan, thereby improving device performance.
Smart Images

Figure CN113497194B_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0040483, filed on April 2, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. TECHNICAL FIELD
[0002] One or more aspects of embodiments of the present disclosure relate to an organic light emitting device and an organic light emitting display apparatus including the same. BACKGROUND
[0003] An organic light emitting device is a self-emissive device that produces a full-color image and also has excellent characteristics of a wide viewing angle, high contrast, a short response time, and / or in luminance, driving voltage, and / or response speed, compared to prior art devices.
[0004] An example organic light emitting device can include a first electrode disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes provided from the first electrode can move toward the emission layer through the hole transport region, and electrons provided from the second electrode can move toward the emission layer through the electron transport region. Carriers such as holes and electrons can recombine in the emission layer to generate excitons. These excitons can transition from an excited state to a ground state, thereby generating light. SUMMARY
[0005] One or more aspects of embodiments of the present disclosure relate to a high-quality organic light emitting device having a low driving voltage, high efficiency, and / or long lifespan.
[0006] Additional aspects will be set forth in part in the description which follows, and in part will become apparent to those skilled in the art upon examination of the following disclosure or can be learned by practice of the disclosed embodiments.
[0007] One or more example embodiments of the present disclosure provide an organic light emitting device including:
[0008] a first electrode,
[0009] a second electrode facing the first electrode, and
[0010] an organic layer between the first electrode and the second electrode and including an emission layer,
[0011] wherein the emission layer includes a host and a dopant,
[0012] the host includes a first compound and a second compound,
[0013] the first compound, the second compound, and the dopant are different from each other,
[0014] The two compounds included in the host in the emission layer have different highest occupied molecular orbital (HOMO) energy levels and lowest unoccupied molecular orbital (LUMO) energy levels, form an exciplex, and
[0015] The difference (△E 激基复合物 ) between the HOMO energy level and the LUMO energy level of the exciplex is greater than the difference (△E 掺杂剂 ) between the HOMO energy level and the LUMO energy level of the dopant.
[0016] In one embodiment, the second compound can have a smaller electron transportability than the first compound.
[0017] In one embodiment, the first compound and the second compound can form an exciplex.
[0018] In one embodiment, the HOMO energy level (HOMO 激基复合物 ) (eV) of the exciplex can be the same as the HOMO energy level (eV) of the first compound or the HOMO energy level (eV) of the second compound, whichever has a smaller absolute value, and the LUMO energy level (LUMO 激基复合物 ) (eV) of the exciplex can be the same as the LUMO energy level (eV) of the first compound or the LUMO energy level (eV) of the second compound, whichever has a larger absolute value.
[0019] In one embodiment, the difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound can be about 0.1 eV or greater, and the difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound can be about 0.1 eV or greater.
[0020] In one embodiment, i) both the first compound and the second compound can include an electron transport moiety, ii) neither the first compound nor the second compound can include an electron transport moiety, or iii) the first compound can include an electron transport moiety, and the second compound can not include an electron transport moiety.
[0021] In one embodiment, i) both the first compound and the second compound can include an electron transport moiety, ii) neither the first compound nor the second compound can include an electron transport moiety, or iii) the first compound can include an electron transport moiety, and the second compound can not include an electron transport moiety, and in all cases, the first compound and the second compound can form an exciplex.
[0022] In one embodiment, the electron transport moiety can be a cyano group, a fluorine group, a π-electron poor nitrogen-containing cyclic group, or any combination thereof.
[0023] In one embodiment, the first compound can be an electron transport host, and the second compound can be a hole transport host.
[0024] In one embodiment, the first compound and the second compound can each have a higher triplet energy level (T1) than the dopant.
[0025] In one embodiment, the weight ratio of the first compound to the second compound can be about 90:10 to about 10:90.
[0026] In one embodiment, the host can further include a third compound; the first compound, the second compound, the third compound, and the dopant can be different from each other, two compounds selected from the host included in the emission layer can have different HOMO energy levels and LUMO energy levels, and can form an exciplex, and the difference (△E 激基复合物 ) between the HOMO energy level and the LUMO energy level of the exciplex can be greater than the difference (△E 掺杂剂 ) between the HOMO energy level and the LUMO energy level of the dopant.
[0027] In one embodiment, the third compound can be an electron transport host, a hole transport host, or a bipolar host.
[0028] In one embodiment, the weight ratio of the first compound and the second compound to the third compound can be about 1:99 to about 99:1.
[0029] In one embodiment, the emission layer can further include two or more hosts, the emission layer including a total of N hosts, where N can be an integer of 4 or more; the two or more hosts, the first compound, the second compound, and the dopant can be different from each other; two compounds selected from the N hosts included in the emission layer can have different HOMO energy levels and LUMO energy levels, and can form an exciplex, and the difference (△E 激基复合物 ) between the HOMO energy level and the LUMO energy level of the exciplex can be greater than the difference (△E 掺杂剂 ) between the HOMO energy level and the LUMO energy level of the dopant.
[0030] In one embodiment, the exciplex can have an energy band gap (△E 激基复合物 ) of about 2.5 eV to about 3.5 eV.
[0031] In one embodiment, the dopant in the emission layer can be a phosphorescent dopant or a fluorescent dopant.
[0032] In one embodiment, the organic layer can further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode; the hole transport region can include at least one selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer; and the electron transport region can 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.
[0033] In one embodiment, the hole transport region can include an arylamine compound.
[0034] In one embodiment, the electron transport region can include a compound including a π-electron poor nitrogen-containing ring.
[0035] One or more example embodiments of the present disclosure provide an organic light emitting device including:
[0036] a first pixel electrode, a second pixel electrode, and a third pixel electrode in a first emission region, a second emission region, and a third emission region, respectively,
[0037] a counter electrode facing the first pixel electrode, the second pixel electrode, and the third pixel electrode, and
[0038] an organic layer between the first pixel electrode, the second pixel electrode, and the third pixel electrode and the counter electrode, and including an emission layer,
[0039] wherein the emission layer includes:
[0040] a first emission layer corresponding to the first emission region and emitting a first color light,
[0041] a second emission layer corresponding to the second emission region and emitting a second color light, and
[0042] a third emission layer corresponding to the third emission region and emitting a third color light,
[0043] wherein a maximum emission wavelength of the first color light and a maximum emission wavelength of the second color light are each greater than a maximum emission wavelength of the third color light,
[0044] at least two emission layers selected from the first emission layer, the second emission layer, and the third emission layer include a host including a first compound and a second compound and a dopant,
[0045] the first compound, the second compound, and the dopant are different from each other,
[0046] the two compounds included in the host in the emission layer have different HOMO and LUMO energy levels, form an exciplex, and
[0047] a difference (ΔE 激基复合物 ) between the HOMO level and the LUMO level of the exciplex is greater than a difference (ΔE 掺杂剂 ) between the HOMO level and the LUMO level of the dopant.
[0048] In one embodiment, the at least one emission layer selected from the first emission layer, the second emission layer, and the third emission layer can further include a third compound different from the first compound and the second compound.
[0049] One or more example embodiments of the disclosure provide an apparatus including a thin film transistor and an organic light emitting device, the thin film transistor including a source electrode, a drain electrode, and an active layer, wherein a first electrode or a pixel electrode of the organic light emitting device is electrically connected to one selected from the source electrode and the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF DRAWINGS
[0050] The above and other aspects, features, and advantages of embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0051] Figure 1 is a schematic diagram of a structure of an organic light emitting device according to an embodiment;
[0052] Figure 2 is an energy level diagram of a first compound, a second compound, an exciplex, and a dopant; and
[0053] Figure 3 is a schematic diagram of a structure of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION
[0054] Reference will now be made in detail embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. It is to be understood that the embodiments can be implemented in various forms without being limited to the description set forth herein. Accordingly, the embodiments are not limited to the description set forth herein, and can include all modifications, equivalents, and substitutes for the described aspects. Therefore, the following description is merely illustrative and explanatory thereof, and it should be understood that the true scope of the embodiments is not limited to the description set forth herein. In this regard, the embodiments can have different forms and should not be construed as being limited to the description set forth herein. Accordingly, the embodiments will be described below by referring to the accompanying drawings, which will explain aspects of the present description. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression "at least one of a, b, and c" can mean only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
[0055] Since the present disclosure can be variously changed and can have various examples, selected examples will be shown in the drawings and described in detail in the detailed description. The effects and features of the present disclosure and methods of achieving them will be clarified by referring to the detailed examples with reference to the accompanying drawings. However, the present disclosure is not limited to the examples disclosed below and can be implemented in various forms.
[0056] As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of the term "may" when describing embodiments of the present disclosure means that one or more embodiments of the present disclosure "can" or "might" so.
[0057] It will also be understood that the terms "comprise" and / or "comprising," when used herein, specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.
[0058] It will be understood that when a layer, region, or component is referred to as being "on" or "to" another layer, region, or component, it can be directly or indirectly formed on the other layer, region, or component. That is, for example, there can be an intervening layer, region, or component.
[0059] The sizes of elements in the drawings can be exaggerated for the purpose of explanation. For example, since the sizes and thicknesses of components in the drawings are arbitrarily shown for the purpose of explanation, the following embodiments of the present disclosure are not limited thereto.
[0060] The term "organic layer" as used herein can refer to a single layer and / or multiple layers located between a first electrode and a second electrode of an organic light emitting device. Materials included in the "organic layer" are not limited to organic materials.
[0061] The expression "(organic layer) includes a compound represented by Formula 1" as used herein can include a case where "(organic layer) includes one compound of Formula 1" and a case where "(organic layer) includes two or more different compounds of Formula 1."
[0062] Figure 1 Description of Drawings
[0063] Figure 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present disclosure. The organic light emitting device 10 includes a first electrode 110, a second electrode 190 facing the first electrode 110, and an organic layer 150 located between the first electrode 110 and the second electrode 190 and including an emission layer.
[0064] Hereinafter, embodiments of the present disclosure will be described in detail with reference to Figure 1The structure of the organic light emitting device 10 according to an embodiment and a method of manufacturing the organic light emitting device 10 are described.
[0065] The first electrode 110
[0066] In Figure 1 In the embodiment, a substrate can be additionally disposed under the first electrode 110 and / or over the second electrode 190. The substrate can be a glass substrate and / or a plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, handleability, and / or water resistance.
[0067] The first electrode 110 can be formed by depositing and / or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be selected from materials having a high work function to facilitate hole injection.
[0068] The first electrode 110 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but embodiments of the disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 110 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 embodiments of the disclosure are not limited thereto.
[0069] The first electrode 110 can have a single layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.
[0070] The organic layer 150
[0071] The organic layer 150 is located on the first electrode 110. The organic layer 150 includes an emission layer.
[0072] The emission layer can include a host and a dopant, the host can include a first compound and a second compound (for example, the emission layer can include a first host compound and a second host compound), and the first compound, the second compound, and the dopant can be different from each other. Here, the term "different from" means that the compounds are different, and the compounds can have different structures, compositions, and properties.
[0073] In one embodiment, the second compound can be a host having a smaller electron transport ability than the first compound.
[0074] The two different host compounds (e.g., molecules) included in the emissive layer can form an exciplex, and the energy level difference (e.g., HOMO-LUMO gap or band gap) (ΔΕ 激基复合物 ) between the highest occupied molecular orbital (HOMO) level and the lowest unoccupied molecular orbital (LUMO) level of the exciplex can be greater than the energy level difference (e.g., HOMO-LUMO gap) (ΔΕ 掺杂剂 ) between the HOMO level and the LUMO level of the dopant.
[0075] The HOMO level (eV) and the LUMO level (eV) of the host, the HOMO level (eV) and the LUMO level (eV) of the exciplex, and the HOMO level (eV) and the LUMO level (eV) of the dopant can each be measured by cyclic voltammetry (CV).
[0076] In one embodiment, the first compound and the second compound can form an exciplex. In this case, the HOMO level (HOMO 激基复合物 ) (eV) of the exciplex can be the same as the HOMO level (eV) of the first compound or the HOMO level (eV) of the second compound, whichever has the smaller (lower) absolute value. For example, the HOMO level of the exciplex can be the same as the shallower of the HOMO level of the first compound and the HOMO level of the second compound.
[0077] In one or more embodiments, the LUMO level (LUMO 激基复合物 ) (eV) of the exciplex can be the same as the LUMO level (eV) of the first compound or the LUMO level (eV) of the second compound, whichever has the greater (higher) absolute value. For example, the LUMO level of the exciplex can be the same as the deeper of the LUMO level of the first compound and the LUMO level of the second compound.
[0078] Figure 2 is an energy level diagram of the first compound, the second compound, the exciplex, and the dopant according to an embodiment.
[0079] Referring to Figure 2 , for example, when the first compound and the second compound form an exciplex, the HOMO level of the exciplex is the same as the HOMO level of the second compound, which has a smaller absolute value than the HOMO level of the first compound; and the LUMO level of the exciplex is the same as the LUMO level of the first compound, which has a greater absolute value than the LUMO level of the second compound.
[0080] Thus, in Figure 2 the example, the difference (e.g., HOMO-LUMO gap) (△E 激基复合物 ) between the HOMO level and the LUMO level of the exciplex formed by the first compound and the second compound can be the same as the difference between the HOMO level of the second compound and the LUMO level of the first compound.
[0081] The energy band gap (△E 掺杂剂 ) of the dopant is smaller than the energy band gap (△E 激基复合物 ) of the exciplex. Figure 2 To facilitate understanding, it is shown that the LUMO level of the dopant is smaller than the LUMO level of the exciplex, and the HOMO level of the dopant is greater than the HOMO level of the exciplex (e.g., such that the HOMO-LUMO gap of the dopant is entirely contained within the HOMO-LUMO gap of the exciplex). However, the HOMO level and the LUMO level of the dopant are not limited thereto, and can each be independently selected as long as these values satisfy the condition of △E 激基复合物 >△E 掺杂剂 .
[0082] When the exciplex in the emission layer and the dopant satisfy the condition of △E 激基复合物 >△E 掺杂剂 , the exciton formed in the exciplex can be effectively transferred to the dopant. In addition, when the emission layer includes at least two hosts, energy can be effectively transferred from the host to the dopant, as compared with the emission layer including a single host. Thus, the organic light emitting device can have high efficiency and / or long lifespan.
[0083] When the emission layer includes two or more hosts, the hole-electron charge balance in the emission layer can be improved as compared with the case of the emission layer including one host. When the first compound has a greater electron mobility than the second compound, the first compound can be an electron transport host having a relatively strong electron transport property in the emission layer, and the second compound can be a hole transport host having a relatively strong hole transport property in the emission layer, but embodiments of the present disclosure are not limited thereto.
[0084] When the emission layer includes at least two hosts, holes provided from the first electrode 110 can flow to the emission layer via the HOMO of the hole transport host, and electrons provided from the second electrode 190 can flow to the emission layer via the LUMO of the electron transport host.
[0085] Even though a hole transport host including holes and an electron transport host including electrons can be in contact with each other in the emission layer, since holes and electrons exist (e.g., are concentrated) in different compounds, excitons are not easily formed. In this case, when the electron transport host transports an electron to the hole transport host, excitons are formed in the hole transport host, or when the hole transport host transports a hole to the electron transport host, excitons are formed in the electron transport host. When the electron transport host and the hole transport host transport an electron and a hole, respectively, to the dopant, excitons are formed in the dopant. In this way, excitons are formed to emit light only when carriers are transferred across the energy barrier therebetween. Thus, the driving voltage of the organic light emitting device can be increased.
[0086] In contrast, in the organic light emitting device according to the embodiments, the two host compounds (e.g., the first compound and the second compound) in the emission layer can have different HOMO energy levels and LUMO energy levels, and can form an exciplex, and thus, excitons can be formed without transferring holes or electrons across the energy barrier therebetween (e.g., the energy barrier for transferring holes and / or electrons can be reduced, and in some embodiments, is substantially zero).
[0087] In this way, when the HOMO energy level and the LUMO energy level of the compounds or materials in the emission layer are aligned to induce efficient carrier injection, the injection of holes and electrons can be improved, and excitons can be formed in the emission layer without an energy barrier due to the exciplex formed by the first compound and the second compound, so that the organic light emitting device 10 can have a low driving voltage and / or high efficiency.
[0088] The first compound and the second compound as the host compounds in the emission layer are not limited to specific compounds, as long as the exciplex formed in the emission layer can satisfy ΔE 激基复合物 >△E 掺杂剂 That is.
[0089] In one or more embodiments, when the first compound and the second compound in the emission layer form an exciplex, in order to efficiently form the exciplex, the difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound can be, for example, about 0.1 eV or more, and the difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound can be, for example, about 0.1 eV or more, but embodiments of the present disclosure are not limited thereto.
[0090] In one embodiment, the HOMO energy level of the second compound can be at least about 0.1 eV higher than the HOMO energy level of the first compound, and the LUMO energy level of the second compound can be at least about 0.1 eV higher than the LUMO energy level of the first compound, although embodiments of the present disclosure are not limited thereto. The first and second compounds satisfying the above energy conditions can effectively form an exciplex.
[0091] In various embodiments, i) both the first and second compounds can include an electron transport moiety, ii) neither the first nor the second compound can include an electron transport moiety, or iii) the first compound can include an electron transport moiety and the second compound can not include an electron transport moiety, or vice versa, in each of which embodiments the first and second compounds can form an exciplex.
[0092] In one embodiment, the electron transport moiety can be a cyano group, a fluoro group, a π-electron-deficient nitrogen-containing cyclic group, or any combination thereof.
[0093] As used herein, the term "π-electron-deficient nitrogen-containing cyclic group" refers to a heterocyclic group having at least one *-N=* moiety as a ring-forming portion.
[0094] In one embodiment, the first compound can be an electron transport host and the second compound can be a hole transport host.
[0095] In one embodiment, both the first and second compounds can include (each) an electron transport moiety, the first compound can be an electron transport host, and the second compound can be a hole transport host. In this case, the relative magnitude of the electron mobility of the first and second compounds is consistent, the first compound can be or function as an electron transport host having electron injection and transport properties, and the second compound can be or function as a hole transport host having hole injection and transport properties.
[0096] In one embodiment, neither the first nor the second compound can include an electron transport moiety, the first compound can be an electron transport host, and the second compound can be a hole transport host. For example, due to the relative magnitude of the electron mobility of the first and second compounds, even the host or the first compound that does not include an electron transport moiety can be or function as an electron transport host having electron injection and transport properties, and the second compound can be or function as a hole transport host having hole injection and transport properties.
[0097] In one or more embodiments, the first compound can be an electron transport host including an electron transport moiety, and the second compound can be a hole transport host including a hole transport moiety.
[0098] The first compound can have high electron transport properties and can stably and efficiently transport electrons, thereby reducing a driving voltage, improving current efficiency, and supporting long lifespan characteristics of a device.
[0099] The second compound can have hole transport properties and can relatively stably and efficiently transport holes, thereby helping to improve device characteristics.
[0100] In one embodiment, the first compound can be a bipolar compound including both an electron transport moiety and a hole transport moiety (e.g., simultaneously). The hole transport moiety can include carbazole, dibenzofuran, dibenzothiophene, amine group (or amino group), etc.
[0101] In one embodiment, both the first compound and the second compound can be bipolar compounds. However, the electron transport capability of the first compound can be greater than the electron transport capability of the second compound.
[0102] In one embodiment, the electron mobility μ(C1) of the first compound can be greater than the electron mobility μ(C2) of the second compound.
[0103] μ(C1) and μ(C2) can each be evaluated using a DFT method, for example, using a Gaussian program for a structure optimized using a B3LYP / 6-31G(d,p) function and basis set.
[0104] In one embodiment, the first compound and the second compound can each have a triplet energy level (T1) higher than that of a dopant.
[0105] When the first compound and the second compound each have a triplet energy level (T1) satisfying the above condition, an exciton recombined in a host or an excimer can be effectively transferred to a dopant.
[0106] In one embodiment, the first compound and the second compound can each be independently selected from the compounds represented by Formulae 1 to 3 and Formula 301.
[0107] Formula 1
[0108]
[0109] In Formula 1,
[0110] X 11 may be O, S, N[(L 11 ) a11 -(R 11 )b11 ], C(R 11a )(R 11b ) or Si(R 11a )(R 11b ),
[0111] Y1to Y8may each independently be N or C(R 14 ), wherein, when C(R 14 ) is two or more, two or more R 14 may be the same or different from each other,
[0112] L 11 to L 13 may each independently be a substituted or unsubstituted C5-C 60 carbocyclyl or a substituted or unsubstituted C1-C 60 heterocyclyl,
[0113] a11to a13may each independently be an integer of 0 to 5,
[0114] R 11 to R 14 and R 11a and R 11b may each independently be selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2),
[0115] from R 11 to R 14R 11a and R 11b The two adjacent groups selected can optionally be located via a single bond, *-O-*', *-S-*', or *-B(R) 15 )-*'、*-N(R 15 )-*'、*-C(R 15 (R) 16 )-*'、*-C(R 15 )=C(R 16 )-*'、C5-C 30 Carbocyclic groups and C1-C 30 The linking groups of the heterocyclic groups are connected together.
[0116] R 15 and R 16 Each can be independently selected from: hydrogen, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl; and all substituted with deuterium, C1-C 20 The phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl groups selected from at least one of the following: alkyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl.
[0117] b11 to b13 can each be an independent integer from 1 to 5, and
[0118] n1 and n2 can both be independent integers from 1 to 4.
[0119] Formula 2
[0120]
[0121] In Equation 2,
[0122] X 21 It can be O, S, N[(L 21 ) a21 -(R 21 ) b21 ]、C(R 21a (R) 21b ) or Si(R 21a (R) 21b ),
[0123] Y 11 To Y 18 They can all be independently N or C(R) 24 ), where, when C(R) 24 When there are two or more R, two or more R 24 They can be the same or different from each other.
[0124] CY1may be a group represented by Formula 2A, and CY2may be a group represented by Formula 2B,
[0125]
[0126] In Formula 2A, C*and C**may each be a carbon condensed with a 5-membered ring containing X 21 ,
[0127] In Formula 2A, Y 19 to Y 22 may each independently be N, C, or C(R 25 ), where, when C(R 25 ) is two or more, two or more R 25 may be the same as or different from each other, and two adjacent groups among Y 19 to Y 22 may each be a carbon condensed with a 5-membered ring containing X 22 ,
[0128] In Formula 2B, X 22 may be O, S, N[(L 24 ) a24 -(R 26 ) b26 ], C(R 26a )(R 26b ), or Si(R 26a )(R 26b ),
[0129] L 21 to L 24 may each independently be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,
[0130] a21to a24may each independently be an integer of 0 to 5,
[0131] R 21 to R 26 , R 21a , R 21b , R 26a , and R 26b may each independently be selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2),
[0132] From R 21 To R 26 R 21a R 21b R 26a and R 26b The two adjacent groups selected can optionally be located via a single bond, *-O-*', *-S-*', or *-B(R) 27 )-*'、*-N(R 27 )-*'、*-C(R 27 (R) 28 )-*'、*-C(R 27 )=C(R 28 )-*'、C5-C 30 Carbocyclic groups and C1-C 30 The linking groups of the heterocyclic groups are connected together.
[0133] R 27 and R 28 Each can be independently selected from: hydrogen, C1-C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl; and all substituted with deuterium, C1-C 20 The phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazole, dibenzofuranyl, and dibenzothiopheneyl groups selected from at least one of the following: alkyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl.
[0134] b21 to b23 and b26 can each be an independent integer from 1 to 5, and
[0135] n21 and n22 can both be independent integers from 1 to 4.
[0136] Formula 3
[0137]
[0138] In Formula 3,
[0139] L 31 may be substituted or unsubstituted C5-C 60 carbocyclyl, or substituted or unsubstituted C1-C 60 heterocyclyl,
[0140] a31may be an integer of 0 to 5,
[0141] R 31 and R 32 may each be independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclyl, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclyl, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2),
[0142] b31and b32may each be independently an integer of 1 to 5, and
[0143] n31may be an integer of 1 to 3.
[0144] In Formulae 1 to 3, L 11 to L 13 , L 21 to L 24 , and L 31 may each be independently selected from the group consisting of:
[0145] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and
[0146] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinoline Linolyl, benzoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl (benzoisothiazolyl, e.g., benzo[d]isothiazolyl), benzoxazolyl, isobenzoxazolyl (benzoisoxazolyl, e.g., benzo[d]isoxazolyl), triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q)31 ) and -P(=O)(Q 31 ) (Q 32 ) selected at least one of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthrylene, benzophenanthrylene, pyrenylene, perylenylene, pentaphenylene, hexaphenylene, pentacenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, diphenzocarbazolylene, diphenzothianolylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phtalazinylene, naphthridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenoxazinylene, phenothiazinylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene and azacarbazolylene,
[0147] wherein Q 31 to Q 33 may each independently be the same as described below.
[0148] In Formulae 1 to 3, R 11 to R 14 , R 11a , R 11b , R 21 to R 26 , R 21a , R 21b , R 26a , R 26b , R 31 and R 32 may each independently be selected from:
[0149] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl and C1-C 20 alkoxy;
[0150] each substituted with at least one of deuterium, -F, -Cl, -Br, -I, cyano, phenyl and biphenyl, C1-C 20 alkyl and C1-C 20 alkoxy;
[0151] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, benzo pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, cyclopenta-benzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiazolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthridinyl, azaf luorenyl, azaspirobi fluorenyl, azacarbazolyl, diazacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, and azadibenzothiazolyl; and
[0152] each independently substituted with deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, naphthyl, fluorenyl, spirobifluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, benzo selected at least one of cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenalene, phenanthryl, fluoranthenyl, benzo[9,10]phenanthryl, benzo selected at least one of cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, spiro-fluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenalene, phenanthryl, fluoranthenyl, benzo[9,10]phenanthryl,
[0153] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), and -B(Q1)(Q2),
[0154] wherein Q1to Q3may each independently be selected from the group consisting of hydrogen, deuterium, C1-C20alkyl, C1-C20alkoxy, phenyl, biphenyl, terphenyl, and naphthyl. 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0155] In one embodiment, the compound represented by Formula 2 can be represented by any one of Formula 2-1 to Formula 2-6:
[0156]
[0157]
[0158] In Formula 2-1 to Formula 2-6, X 21 , X 22 , Y 11 to Y 22 , L 22 , L 23 , a22, a23, R 22 , R 23 , b22, b23, n21 and n22 can each independently be the same as described in the present specification.
[0159] In one embodiment, the compound represented by Formula 3 can be represented by Formula 3-1:
[0160] Formula 3-1
[0161]
[0162] In Formula 3-1, L 31 , a31, R 31 , R 32 , b31 and b32 can each independently be the same as described in the present specification,
[0163] L 32 and R 33 may each independently be the same as described in connection with L 31 and R 31 , respectively,
[0164] a32 can be an integer of 0 to 5, and
[0165] b33 can be an integer of 1 to 5.
[0166] Formula 301
[0167] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0168] In Formula 301,
[0169] Ar 301 may be selected from the group consisting of substituted or unsubstituted C5-C 60 carbocyclyl, and substituted or unsubstituted C1-C60 heterocyclyl,
[0170] xb11may be an integer from 1 to 3,
[0171] L 301 may be selected from substituted or unsubstituted C3-C 10 cycloalkylene, substituted or unsubstituted C1-C 10 heterocycloalkylene, substituted or unsubstituted C3-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted bivalent non-aromatic condensed polycyclic group and substituted or unsubstituted bivalent non-aromatic condensed heteropolycyclic group,
[0172] xb1may be an integer from 0 to 5,
[0173] R 301 may be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ) and -P(=O)(Q 301 )(Q302 ), and
[0174] xb21 can be an integer from 1 to 5,
[0175] wherein Q 301 to Q 303 may each independently be selected from a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto. Each of * and * represents a bonding site to an adjacent atom.
[0176] In one embodiment, Ar 301 in formula 301 can be selected from:
[0177] a naphthyl group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthen group, a benzo[9,10]phenanthrene group, a pyrene group, a chrysene group, a naphthacene group, a triphenylene group, a pyranthrene group, a pentaphene group, an indanthracene group, a dibenzofuran group, and a dibenzothiophene group; and
[0178] each of which is substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a -Si(Q 31 )(Q 32 )(Q 33 ), a -N(Q 31 )(Q 32 ), a -B(Q 31 )(Q 32 ), a -C(=O)(Q 31 ), a -S(=O)2(Q 31 ), and a -P(=O)(Q 31 )(Q 32 alkyl group, a C1-C 31 alkyl group, a C1-C 33 a naphthyl group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthen group, a benzo[9,10]phenanthrene group, a pyrene group, a chrysene group, a naphthacene group, a triphenylene group, a pyranthrene group, a pentaphene group, an indanthracene group, a dibenzofuran group, and a dibenzothiophene group,
[0179] wherein Q 31 to Q 33 may each independently be selected from a C1-C 10 alkyl group, a C1-C 10Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.
[0180] When xb11 in equation 301 is 2 or greater, two or more Ar 301 It can be connected via a single key.
[0181] In one embodiment, the compound represented by formula 301 may be represented by formula 301-1 or formula 301-2:
[0182] Formula 301-1
[0183]
[0184] Formula 301-2
[0185]
[0186] In Equations 301-1 and 301-2,
[0187] A 301 To A 304 They can all be independently selected from benzene rings, naphthalene rings, phenanthrene rings, fluoranthene rings, benzo[9,10]phenanthrene rings, pyrene rings, Rings, pyridine rings, pyrimidine rings, indene rings, fluorene rings, spirobisfluorene 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.
[0188] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0189] R 311 To R 314 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q)31 ) and -P(=O)(Q 31 (Q) 32 ),
[0190] xb22 and xb23 can each be independently 0, 1, or 2.
[0191] L 301 xb1, R 301 and Q 31 To Q 33 Each can be independently identical to the one described above.
[0192] L 302 To L 304 They can all independently bind with L 301 The descriptions are the same.
[0193] xb2 to xb4 can all be independently identical to those described in conjunction with xb1, and
[0194] R 302 To R 304 They can all independently bind with R 301 The descriptions are the same.
[0195] For example, L in Equations 301, 301-1, and 301-2 301 To L 304 Each can be independently selected from:
[0196] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and
[0197] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, pyryl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ) selected from at least one of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, pyrylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilolylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenoxazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene,
[0198] wherein Q 31 to Q 33Each can be independently identical to the one described above.
[0199] In one embodiment, R in Equations 301, 301-1, and 301-2 301 To R 304 Each can be independently selected from:
[0200] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0201] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q)32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ) selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthridinyl, quinoxalyl, quinazolyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenoxazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl,
[0202] wherein Q 31 to Q 33 may each independently be the same as described above.
[0203] In one or more embodiments, the first compound and the second compound can each independently be selected from the group consisting of Compound C1 to Compound C12 and Compound H1 to Compound H55, but embodiments of the present disclosure are not limited thereto:
[0204]
[0205]
[0206]
[0207] In one or more embodiments, the first compound and the second compound can each independently be selected from the group consisting of Compound C1 to Compound C12 and Compound H1 to Compound H55, but the first compound and the second compound are different from each other. In addition, the electron transportability of the second compound can be less than the electron transportability of the first compound.
[0208] When the host includes the first compound and the second compound, the weight ratio of the first compound to the second compound can be about 90:10 to about 10:90. In one or more embodiments, the weight ratio of the first compound to the second compound can be about 20:80 to about 80:20 or about 30:70 to about 70:30. When the weight ratio of the first compound to the second compound is within the range, charge balance in the emission layer can be maintained, and thus efficiency and lifetime can be improved.
[0209] In one embodiment, the host can include a third compound in addition to the first compound and the second compound. The first compound, the second compound, the third compound, and the dopant are different from each other.
[0210] When the carrier transport property of the first host compound and / or the second host compound is insufficient, charge balance in the emission layer can be achieved by introducing a third compound different from the first compound and the second compound. Thus, efficiency and lifetime of the organic light emitting device can be further improved.
[0211] In one or more embodiments, the third compound can be an electron transport host, a hole transport host, or a bipolar host.
[0212] Two (e.g., any two) of the host compounds in the emission layer can have different HOMO energy levels and LUMO energy levels and form an exciplex, and the difference (ΔE 激基复合物 ) between the HOMO energy level and the LUMO energy level of the exciplex can be greater than the difference (ΔE 掺杂剂 ) between the HOMO energy level and the LUMO energy level of the dopant.
[0213] In various embodiments, the first compound and the second compound can form an exciplex, the second compound and the third compound can form an exciplex, or the first compound and the third compound can form an exciplex, but embodiments of the disclosure are not limited thereto.
[0214] In one embodiment, the first compound, the second compound, and the third compound can each have a triplet energy level (T1) higher than that of the dopant.
[0215] When the first compound, the second compound, and the third compound each have a triplet energy level (T1) satisfying the condition, the exciton formed by binding in any host or exciplex can be effectively transferred to the dopant.
[0216] In one embodiment, the third compound can have electron transport properties or hole transport properties.
[0217] In one or more embodiments, the first compound can be an electron transport host, and the second and third compounds can each be a hole transport host. In one or more embodiments, the first and second compounds can each be an electron transport host, and the third compound can be a hole transport host. In one or more embodiments, the first and third compounds can each be an electron transport host, and the second compound can be a hole transport host. The third compound can supplement the relatively deficient carrier transport properties in the emissive layer of the composition including the first and second compounds.
[0218] In one or more embodiments, the third compound can include an electron transport moiety.
[0219] In one or more embodiments, the third compound can not include an electron transport moiety.
[0220] In one embodiment, the third compound can be selected from the compounds represented by Formulae 1 to 3 above.
[0221] In one or more embodiments, the third compound can be selected from the compounds C1 to C12 and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
[0222]
[0223]
[0224]
[0225]
[0226] In one or more embodiments, the first to third compounds can each be independently selected from the compounds C1 to C12 and compounds H1 to H55, but the first, second, and third compounds are different from each other. At the same time (e.g., synchronously), the electron transport capability of the second compound can be less than the electron transport capability of the first compound.
[0227] When the host includes the first compound, the second compound, and the third compound, the weight ratio of the first compound and the second compound to the third compound can be about 1:99 to about 99:1. In this case, the weight ratio of the first compound to the second compound can be about 10:90 to about 90:10. When these ranges are satisfied, the electron transportability of the first compound and the hole transportability of the second compound can be balanced so that the ambipolar property can be achieved, and the third compound can complement the relatively insufficient carrier transport property in the emission layer. Accordingly, the efficiency and / or the lifespan of the organic light emitting device can be improved. In one or more embodiments, the weight ratio of the first compound and the second compound to the third compound can be about 10:90 to about 90:10, about 20:80 to about 80:20, about 30:70 to about 70:30, about 40:60 to about 70:30, or about 50:50 to about 70:30.
[0228] In one or more embodiments, the emission layer can further include two or more hosts (e.g., at least four or more host compounds in total), and the two or more hosts, the first compound, the second compound, and the dopant can be different from each other.
[0229] In this case, two of the compounds having different HOMO and LUMO energy levels among the N hosts included in the emission layer (where N is an integer of 4 or more) can form an excimer, and the difference (ΔE 激基复合物 ) between the HOMO and LUMO energy levels of the excimer can be greater than the difference (ΔE 掺杂剂 ) between the HOMO and LUMO energy levels of the dopant.
[0230] When N different hosts are included in the emission layer, the emission layer can include the first compound to the Nth compound.
[0231] For example, the emission layer of the organic light emitting device 10 can include one of the following combinations:
[0232] i) the first compound, the second compound, and the dopant;
[0233] ii) the first compound, the second compound, the third compound, and the dopant; and
[0234] iii) the first compound, the second compound, the third compound, …, the N-1th compound, the Nth compound, and the dopant.
[0235] The excimer can have, for example, an energy band gap (ΔE 激基复合物 ) of about 2.5 eV to about 3.5 eV.
[0236] When the dopant is a red dopant, the dopant can have an energy band gap (△E 掺杂剂 ) of about 1.7 eV to about 3.2 eV. When the dopant is a green dopant, the dopant can have an energy band gap (△E 掺杂剂 ) of about 1.9 eV to about 3.2 eV. When the dopant is a blue dopant, the dopant can have an energy band gap (△E 掺杂剂 ).
[0237] The dopant can be, for example, a phosphorescent dopant or a fluorescent dopant. The phosphorescent dopant or the fluorescent dopant can each be a red dopant, a green dopant, or a blue dopant. In one or more embodiments, the phosphorescent dopant can be a red phosphorescent dopant or a green phosphorescent dopant, and / or the fluorescent dopant can be a blue fluorescent dopant.
[0238] In one or more embodiments, the amount of the dopant in the emission layer can be about 0.01 parts by weight to about 30 parts by weight, based on about 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0239] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, or a blue emission layer according to a sub-pixel. In one or more embodiments, the emission layer can have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers can be in contact with each other or can be separated from each other. In one or more embodiments, the emission layer can include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0240] When the emission layer is patterned into a red emission layer, a green emission layer, or a blue emission layer according to a sub-pixel, at least one of the red emission layer, the green emission layer, and the blue emission layer can include a first compound, a second compound, and a dopant, or in some embodiments, at least one of the red emission layer, the green emission layer, and the blue emission layer can include a first compound, a second compound, a third compound, and a dopant.
[0241] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is in this range, excellent light-emitting properties can be obtained without significantly increasing the driving voltage.
[0242] The organic layer 150 can further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 190.
[0243] The hole transport region in the organic layer 150
[0244] The hole transport region can have i) a single layer structure including (e.g., consisting of) a single material, ii) a single layer structure including (e.g., consisting of) a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including (e.g., consisting of) a plurality of different materials.
[0245] The hole transport region can include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
[0246] For example, the hole transport region can have a single layer structure including (e.g., consisting of) a plurality of different materials, or a multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, in which the constituent layers of each structure are sequentially stacked from the first electrode 110 in the order of each statement, but the structure of the hole transport region is not limited thereto.
[0247] The hole transport region can include an arylamine compound or a hole transport polymer.
[0248] In one or more embodiments, the hole transport region can include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
[0249]
[0250]
[0251] Formula 201
[0252]
[0253] Formula 202
[0254]
[0255] In Formula 201 and Formula 202,
[0256] L 201 to L 204 may each independently be selected from substituted or unsubstituted C3-C 10 cycloalkylene, substituted or unsubstituted C1-C 10 heterocycloalkylene, substituted or unsubstituted C3-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0257] L 205 may be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C1-C 20 alkylene, substituted or unsubstituted C2-C 20 alkenylene, substituted or unsubstituted C3-C 10 cycloalkylene, substituted or unsubstituted C1-C 10 heterocycloalkylene, substituted or unsubstituted C3-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0258] xa1to xa4may each independently be an integer of 0 to 3,
[0259] xa5may be an integer of 1 to 10, and
[0260] R 201 to R 204 and Q 201 may each independently be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0261] In one or more embodiments, in Formula 202, R 201 and R 202 may be optionally connected to each other via a single bond, dimethyl-methylene or diphenyl-methylene, and R 203 and R 204 may be optionally connected to each other via a single bond, dimethyl-methylene or diphenyl-methylene.
[0262] In one embodiment, in Formula 201 and Formula 202,
[0263] L 201 to L 205 may each independently be selected from:
[0264] Phenylene, indenylene, indenyl, naphthylene, azulenyl, heptaienyl, indacene, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, Phenylene, indenylene, indenyl, naphthylene, azulenyl, heptaienyl, indacene, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl,
[0265] each substituted with from one to three of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, azulenyl, indenyl, naphthyl, azulenyl, heptaienyl, indacene, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, phenylene, naphthylene, azulenylene, perylenylene, pentaphenylene, hexaphenylene, pentacenylene, coronenylene, ovalenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, diphenzocarbazolylene, dithianthreneylene, and pyridinylene, 31 (Q 32 (Q 33 ) and -N(Q 31 )(Q 32 ) selected from at least one of phenylene, naphthylene, azulenylene, perylenylene, pentaphenylene, hexaphenylene, pentacenylene, coronenylene, ovalenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, diphenzocarbazolylene, dithianthreneylene, and pyridinylene, (Q (Q
[0266] wherein Q 31 to Q 33 may each independently be selected from C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0267] In one embodiment, xa1to xa4may each independently be 0, 1, or 2.
[0268] In one embodiment, xa5may be 1, 2, 3, or 4.
[0269] In one embodiment, R 201 to R 204 and Q 201 may each independently be selected from phenyl, biphenyl, terphenyl, cyclopentacene, indene, naphthalene, azulene, heptalene, indacene, acenaphthene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, benzo[9,10]phenanthrene, pyrene, phenylene, naphthylene, azulenylene, perylenylene, pentaphenylene, hexaphenylene, pentacenylene, coronenylene, ovalenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, diphenzocarbazolylene, dithianthreneylene, and pyridinylene,
[0270] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, cyclopentadienyl, indole, naphthyl, chamomilecycloyl, heptalenyl, indoleyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.
[0271] Among them, Q 31 To Q 33 Each can be independently identical to the one described above.
[0272] In one embodiment, R in equation 201 201 To R 203 At least one of them can be independently selected from:
[0273] Fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl; and
[0274] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20alkyl, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C6alkyl, C1-C6alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C6alkyl, phenyl substituted with -F, naphthyl, fluorenyl, spirobifluorenyl, carbazolyl, diphenylene fluorenyl, diphenylene spirobifluorenyl, diphenylene carbazolyl, diphenylene dibenzofuranyl, and diphenylene dibenzothiophenyl, 10 fluorenyl, spirobifluorenyl, carbazolyl, diphenylene fluorenyl, diphenylene spirobifluorenyl, diphenylene carbazolyl, diphenylene dibenzofuranyl, and diphenylene dibenzothiophenyl,
[0275] Embodiments of the present disclosure are not limited thereto, however.
[0276] In one embodiment, in Formula 202, i) R 201 and R 202 may be connected to each other via a single bond, and / or ii) R 203 and R 204 may be connected to each other via a single bond.
[0277] In one embodiment, R 201 to at least one of R 204 may be selected from:
[0278] carbazolyl; and
[0279] substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C6alkyl, C1-C6alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C6alkyl, phenyl substituted with -F, naphthyl, fluorenyl, spirobifluorenyl, carbazolyl, diphenylene fluorenyl, diphenylene spirobifluorenyl, diphenylene carbazolyl, diphenylene dibenzofuranyl, and diphenylene dibenzothiophenyl, 20 C1-C6alkyl, C1-C6alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C6alkyl, phenyl substituted with -F, naphthyl, fluorenyl, spirobifluorenyl, carbazolyl, diphenylene fluorenyl, diphenylene spirobifluorenyl, diphenylene carbazolyl, diphenylene dibenzofuranyl, and diphenylene dibenzothiophenyl, 20 C1-C6alkyl, C1-C6alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C6alkyl, phenyl substituted with -F, naphthyl, fluorenyl, spirobifluorenyl, carbazolyl, diphenylene fluorenyl, diphenylene spirobifluorenyl, diphenylene carbazolyl, diphenylene dibenzofuranyl, and diphenylene dibenzothiophenyl, 10 carbazolyl, diphenylene fluorenyl, diphenylene spirobifluorenyl, diphenylene carbazolyl, diphenylene dibenzofuranyl, and diphenylene dibenzothiophenyl,
[0280] Embodiments of the present disclosure are not limited thereto, however.
[0281] The compound represented by Formula 201 can be represented by Formula 201-1:
[0282] Formula 201-1
[0283]
[0284] In one embodiment, the compound represented by Formula 201 can be represented by Formula 201-2, but embodiments of the present disclosure are not limited thereto:
[0285] Formula 201-2
[0286]
[0287] In one or more embodiments, the compound represented by formula 201 can be represented by formula 201-2(1), but embodiments of the present disclosure are not limited thereto:
[0288] Formula 201-2(1)
[0289]
[0290] In one or more embodiments, the compound represented by formula 201 can be represented by formula 201A:
[0291] Formula 201A
[0292]
[0293] In one or more embodiments, the compound represented by formula 201 can be represented by formula 201A(1), but embodiments of the present disclosure are not limited thereto:
[0294] Formula 201A(1)
[0295]
[0296] In one or more embodiments, the compound represented by formula 201 can be represented by formula 201A-1, but embodiments of the present disclosure are not limited thereto:
[0297] Formula 201A-1
[0298]
[0299] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202-1:
[0300] Formula 202-1
[0301]
[0302] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202-1(1):
[0303] Formula 202-1(1)
[0304]
[0305] In one embodiment, the compound represented by formula 202 can be represented by formula 202A:
[0306] Formula 202A
[0307]
[0308] In one or more embodiments, the compound represented by Formula 202 can be represented by Formula 202A-1:
[0309] Formula 202A-1
[0310]
[0311] In Formula 201-1, Formula 201-2, Formula 201-2(1), Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202-1, Formula 202-1(1), Formula 202A, and Formula 202A-1,
[0312] L 201 to L 203 , xa1to xa3, xa5, and R 202 to R 204 may each independently be the same as described above,
[0313] L 205 may be selected from the group consisting of phenylene and fluorenylene,
[0314] X 211 may be selected from the group consisting of O, S, and N(R 211 ),
[0315] X 212 may be selected from the group consisting of O, S, and N(R 212 ),
[0316] R 211 and R 212 may each independently be the same as described in connection with R 203 , and
[0317] R 213 to R 217 may each independently be selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, and indenyl, naphthyl, azulenyl, heptalynyl, indacenyl, acenaphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, anthracenyl, chrysenyl, pyrenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, coronenyl, coroniendyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothianthrenyl, and pyridyl.
[0318] The hole transport region can include at least one compound selected from the group consisting of compounds HT1 to HT72, but the compound to be included in the hole transport region is not limited thereto:
[0319]
[0320]
[0321]
[0322]
[0323]
[0324]
[0325] The thickness of the hole transport region can be about 1 nm to about 1000 nm. for example, about 10 nm to about 500 nm. for example, about 10 nm to about 500 nm. for example, about 10 nm to about 500 nm. When the thickness of the hole transport region is within the above range, satisfactory hole transport properties can be obtained without significantly increasing the driving voltage.
[0326] The emission auxiliary layer can improve the light emission efficiency by compensating for the optical resonance distance of the wavelength of light emitted by the emission layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer can each include the materials as described above.
[0327] p-dopant
[0328] In addition to these materials, the hole transport region can further include a charge generating material for improving the electrical conductivity. The charge generating material can be uniformly or non-uniformly dispersed in the hole transport region.
[0329] The charge generating material can be, for example, a p-dopant.
[0330] In one embodiment, the LUMO level of the p-dopant can be -3.5 eV or less.
[0331] The p-dopant can include at least one selected from the group consisting of a quinone derivative, a metal oxide, and a cyano-containing compound, but embodiments of the present disclosure are not limited thereto.
[0332] In one embodiment, the p-dopant can include at least one selected from the following compounds:
[0333] a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0334] a metal oxide such as tungsten oxide or molybdenum oxide;
[0335] 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile (HAT-CN); and
[0336] a compound represented by Formula 221,
[0337] However, embodiments of the present disclosure are not limited thereto:
[0338]
[0339] Formula 221
[0340]
[0341] In Formula 221,
[0342] R 221 to R 223 may each be independently selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and R 221 to R 223 at least one of R 20 may have at least one substituent selected from cyano, -F, -Cl, -Br, -I, C1-C 20 alkyl substituted with -Cl, C1-C 20 alkyl substituted with -Br, and C1-C 20 alkyl substituted with -I.
[0343] Phosphorescent dopant in an emission layer
[0344] The phosphorescent dopant can include an organometallic complex represented by Formula 401:
[0345] Formula 401
[0346] M(L 401 ) xc1 (L 402 ) xc2
[0347] Formula 402
[0348]
[0349] In Formula 401 and Formula 402,
[0350] 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),
[0351] L 401 may be selected from the ligand represented by Formula 402, and xc1may be 1, 2, or 3, wherein, when xc1is 2 or more, two or more L 401 may be the same as or different from each other,
[0352] L 402 may be an organic ligand, and xc2may be an integer of 0 to 4, wherein, when xc2may be 2 or more, two or more L 402 may be the same as or different from each other,
[0353] X 401 to X 404 may each independently be nitrogen or carbon,
[0354] X 401 and X 403 may be connected via a single bond or a double bond, X 402 and X 404 may be connected via a single bond or a double bond,
[0355] A 401 and A 402 may each independently be C5-C 60 carbocyclyl or C1-C 60 heterocyclyl,
[0356] X 405 may 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 = *, wherein Q 411 and Q 412 may each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,
[0357] X 406 may be a single bond, O, or S,
[0358] R 401 and R 402 may each independently be selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 20 alkyl, substituted or unsubstituted C1-C 20 alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ), and -P(=O)(Q 401 )(Q 402 ), and Q 401 through Q 403 may each independently be selected from the group consisting of C1-C 10 alkyl, C1-C 10 alkoxy, C6-C 20 aryl, and C1-C 20 heteroaryl,
[0359] xc11and xc12may each independently be an integer from 0 to 10, and
[0360] * and *' in formula 402 each represent a binding site to M in formula 401.
[0361] In one embodiment, A in formula 402 401 and A 402 may each independently be selected from the group consisting of phenyl, naphthyl, fluorenyl, spirobifluorenyl, indenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiophenyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl.
[0362] In one or more embodiments, in formula 402, i) X 401 may be nitrogen, X 402 may be carbon, or ii) X 401 and X 402 may each be nitrogen.
[0363] In one or more embodiments, R 401 and R 402 may each independently be selected from the group consisting of:
[0364] hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, and C1-C 20 alkoxy;
[0365] each substituted with at least one selected from the group consisting of deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, and C1-C 20 alkoxy;
[0366] cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0367] each substituted with at least one selected from the group consisting of deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, and C1-C 20The cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups selected from at least one of the following: cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups; and
[0368] -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 ),
[0369] Among them, Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, and naphthyl groups are used, but the embodiments disclosed herein are not limited thereto.
[0370] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two A's in 401 Optionally via X 407 (X 407 As connecting bases, the two A's are connected to each other. 402 Optionally via X 408 (X 408 (As linking groups) they are connected to each other (see compounds PD1 to PD4 and PD7). X 407 and X 408 They can all be independent single bonds, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q414 They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments disclosed herein are not limited thereto.
[0371] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The ligands may be selected from halogens, diketones (e.g., acetylacetone (compound)), carboxylic acids (e.g., pyridinecarboxylic acid (salt)), -C (=O), isonitriles, -CN and phosphorus ligands (e.g., phosphine or phosphorous acid (salt)), but the embodiments of this disclosure are not limited thereto.
[0372] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25, but the embodiments of this disclosure are not limited thereto:
[0373]
[0374]
[0375] Fluorescent dopants in the emission layer
[0376] Fluorescent dopants may include arylamine compounds or styreneamine compounds.
[0377] Fluorescent dopants may include compounds represented by Formula 501:
[0378] Formula 501
[0379]
[0380] In Equation 501,
[0381] Ar 501 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,
[0382] L 501 To L 503 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60heteroarylene, substituted or unsubstituted bivalent non-aromatic condensed polycyclic group and substituted or unsubstituted bivalent non-aromatic condensed heteropolycyclic group,
[0383] xd1 to xd3 can each independently be an integer of 0 to 3,
[0384] R 501 and R 502 may each independently be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
[0385] xd4 can be an integer of 1 to 6.
[0386] In one embodiment, Ar 501 may be selected from:
[0387] naphthyl group, heptacenyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzo[9,10]phenanthryl group, pyrenyl group, group, naphthacenyl group, chrysenyl group, perylenyl group, pentaphenyl group, indanthryl group, and indenophenanthryl group; and
[0388] each of which is substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl group, heptacenyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzo[9,10]phenanthryl group, pyrenyl group, group, naphthacenyl group, chrysenyl group, perylenyl group, pentaphenyl group, indanthryl group, and indenophenanthryl group.
[0389] In one embodiment, L 501 to L 503 may each independently be selected from:
[0390] phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, perylenylene, pentaphenylene, hexa- phenylene, pentacenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dithianthrylene, and pyridinylene; and
[0391] each independently substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C20alkyl, C1-C20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, perylenylene, pentaphenylene, hexa- phenylene, pentacenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dithianthrylene, and pyridinylene; and phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, perylenylene, pentaphenylene, hexa- phenylene, pentacenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dithianthrylene, and pyridinylene; and
[0392] In one or more embodiments, R 501 and R 502 may each independently be selected from:
[0393] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, perylenylene, pentaphenylene, hexa- phenylene, pentacenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dithianthrylene, and pyridinylene; and
[0394] each independently substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C20alkyl, C1-C20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl,20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, 31 (Q 32 (Q 33 phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl,
[0395] wherein Q 31 to Q 33 may each independently be selected from C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0396] In one or more embodiments, xd4in Formula 501 can be 2, but embodiments of the present disclosure are not limited thereto.
[0397] For example, the fluorescent dopant can be selected from the following compounds FD1 to FD22:
[0398]
[0399]
[0400]
[0401] In one or more embodiments, the fluorescent dopant can be selected from the following compounds, but embodiments of the present disclosure are not limited thereto:
[0402]
[0403] Electron transport region in organic layer 150
[0404] The electron transport region can have: i) a single layer structure including a single material (e.g., consisting of a single material), ii) a single layer structure including a plurality of different materials (e.g., consisting of a plurality of different materials), or iii) a multi-layer structure having a plurality of layers including a plurality of different materials (e.g., consisting of a plurality of different materials).
[0405] The electron transport region can include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.
[0406] 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, in which the constituent layers of each structure are sequentially stacked from the emission layer in the order stated. However, embodiments of the structure of the electron transport region are not limited thereto.
[0407] The electron transport region (e.g., the buffer layer, the hole blocking layer, the electron control layer, and / or the electron transport layer in the electron transport region) can include a metal-free compound including at least one π-electron-poor nitrogen-containing ring.
[0408] The "π-electron-poor nitrogen-containing ring" refers to a C1-C 60 heterocyclyl.
[0409] For example, the "π-electron-poor nitrogen-containing ring" can be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=* portion; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=* portion are condensed with each other; or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups each having at least one *-N=* portion is condensed with at least one C5-C 60 heterocyclyl.
[0410] Non-limiting examples of the π-electron-poor nitrogen-containing ring include an imidazole ring, a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an indazole ring, a purine ring, a quinoline ring, an isoquinoline ring, a benzoquinoline ring, a phthalazine ring, a naphthylidine ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, a phenanthridine ring, an acridine ring, a phenanthroline ring, a phenoxazine ring, a benzimidazole ring, an isobenzothiazole ring, a benzoxazole ring, an isobenzoxazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a triazine ring, a thiadiazole ring, an imidazopyridine ring, an imidazopyrimidine ring, and an azacarbazole ring.
[0411] For example, the electron transport region can include a compound represented by Formula 601:
[0412] Formula 601
[0413] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0414] In Formula 601,
[0415] Ar 601 may be a substituted or unsubstituted C5-C 60 carbocyclyl or a substituted or unsubstituted C1-C 60 heterocyclyl,
[0416] xe11may be 1, 2, or 3,
[0417] L 601 may be selected from substituted or unsubstituted C3-C 10 cycloalkylene, substituted or unsubstituted C1-C 10 heterocycloalkylene, substituted or unsubstituted C3-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted bivalent non-aromatic condensed polycyclic group, and substituted or unsubstituted bivalent non-aromatic condensed heteropolycyclic group,
[0418] xe1may be an integer of 0 to 5,
[0419] R 601 may be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601, -S(=O)2(Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0420] Q 601 to Q 603 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0421] xe21may be an integer from 1 to 5.
[0422] In one embodiment, at least one of xe11Ar 601 and xe21R 601 may include a nitrogen-containing ring that is poor in π-electrons.
[0423] In one embodiment, Ar 601 in formula 601 can be selected from:
[0424] a phenyl group, a naphthyl group, a fluorene group, a spirobifluorene group, a benzo fluorene group, a dibenzo fluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthen group, a benzo[9,10]phenanthrene group, a pyrene group, a tetracene group, a chrysene group, a naphthacene group, an indenanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indolizine group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthylidine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenoxazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, a oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and
[0425] each of which is substituted with from one to three groups independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 , -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32The phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, selected from at least one of the following: Groups, tetraphenyl group, styrene group, perylene group, pentylenetetrazol group, indoxanthracene 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, benzooxazole group, isobenzooxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group,
[0426] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0427] When xe11 in equation 601 is 2 or greater, two or more Ar 601 They can be connected to each other via a single key.
[0428] In one embodiment, Ar in Formula 601 601 It can be an anthracene group.
[0429] In one or more embodiments, the compound represented by formula 601 can be represented by formula 601-1:
[0430] Formula 601-1
[0431]
[0432] In Equation 601-1,
[0433] 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 X 614 To X 616 At least one of them can be N,
[0434] L 611 To L613 They can all independently bind with L 601 The descriptions are the same.
[0435] xe611 to xe613 can all be independently identical to those described in conjunction with xe1.
[0436] R 611 To R 613 They can all independently bind with R 601 The descriptions are the same, and
[0437] R 614 To R 616 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0438] In one embodiment, L in Equation 601 601 L in Equation 601-1 611 To L 613 Each can be independently selected from:
[0439] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and
[0440] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyryl, phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrylene, phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrylene,
[0441] However, embodiments of the present disclosure are not limited thereto.
[0442] In one embodiment, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can each independently be 0, 1, or 2.
[0443] In one or more embodiments, R 601 and R 611 to R 613 may each independently be selected from:
[0444] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyryl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyryl,
[0445] each of which is substituted with at least one selected from deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 20 alkyl, C1-C 20 phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyryl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyryl, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0446] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0447] Among them, Q 601 and Q 602 Each can be independently identical to the one described above.
[0448] The electron transport region may include at least one compound selected from compounds ET1 to ET96, but the compounds to be included in the electron transport region are not limited to these:
[0449]
[0450]
[0451]
[0452]
[0453]
[0454]
[0455]
[0456] In one or more embodiments, the electron transport region may include at least one compound 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.
[0457]
[0458] The thickness of the buffer layer, the hole blocking layer, and the electron control layer can each independently be about 1 nm to about 100 nm. for example, about 1 nm to about 10 nm. for example, about 1 nm to about 10 nm. for example, about 1 nm to about 10 nm. When the thickness of the buffer layer, the hole blocking layer, and the electron control layer is within these ranges, excellent hole blocking characteristics or excellent electron control characteristics can be obtained without significantly increasing the driving voltage.
[0459] The thickness of the electron transport layer can be about 1 nm to about 100 nm. for example, about 1 nm to about 10 nm. for example, about 1 nm to about 10 nm. for example, about 1 nm to about 10 nm. When the thickness of the electron transport layer is within the above range, the electron transport layer can have satisfactory electron transport characteristics without significantly increasing the driving voltage.
[0460] In addition to the above-described materials, the electron transport region (e.g., the electron transport layer in the electron transport region) can further include a metal-containing material.
[0461] The metal-containing material can include at least one selected from an alkali metal complex and an alkaline earth metal complex. The metal ion of the alkali metal complex can be selected from a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and a cesium (Cs) ion, and the metal ion of the alkaline earth metal complex can be selected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, and a barium (Ba) ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex can be selected from a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl-oxazole, a hydroxyphenyl-thiazole, a hydroxyphenyl-oxadiazole, a hydroxyphenyl-thiadiazole, a hydroxyphenyl-pyridine, a hydroxyphenyl-benzimidazole, a hydroxyphenyl-benzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
[0462] For example, the metal-containing material can include a Li complex. The Li complex can include, for example, a compound ET-D1 (lithium hydroxyquinoline, LiQ) or a compound ET-D2:
[0463]
[0464] The electron transport region can include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer can be in direct contact with the second electrode 190.
[0465] The electron injection layer can have: i) a single layer structure comprising a single material (e.g., consisting of a single material), ii) a single layer structure comprising a plurality of different materials (e.g., consisting of a plurality of different materials), or iii) a multi-layer structure having a plurality of layers comprising a plurality of different materials (e.g., consisting of a plurality of different materials).
[0466] The electron injection layer can comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0467] 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 embodiment, the alkali metal can be Li or Cs, although embodiments of the present disclosure are not limited thereto.
[0468] The alkaline earth metal can be selected from Mg, Ca, Sr, and Ba.
[0469] The rare earth metal can be selected from scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).
[0470] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound can be selected from oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal.
[0471] The alkali metal compound can be selected from alkali metal oxides (such as Li2O, Cs2O, and / or K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI). In one embodiment, the alkali metal compound can be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, although embodiments of the present disclosure are not limited thereto.
[0472] The alkaline earth metal compound can be selected from alkaline earth metal oxides (such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1) and / or Ba x Ca 1-x O (0 < x < 1)). In one embodiment, the alkaline earth metal compound can be selected from BaO, SrO, and CaO, although embodiments of the present disclosure are not limited thereto.
[0473] 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 embodiments of the present disclosure are not limited thereto.
[0474] The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex can include ions of the alkali metal, the alkaline earth metal, and the rare earth metal as described above, and the ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth metal complex, or the 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 embodiments of the present disclosure are not limited thereto.
[0475] The electron injection layer can include (e.g., consist of) the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof as described above. In one or more embodiments, the electron injection layer can further include an organic material. When the electron injection layer further includes the organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or the combination thereof can be uniformly or non-uniformly dispersed in a matrix including (e.g., formed of) the organic material.
[0476] The thickness of the electron injection layer can be about 0.1 nm to about 10 nm. to about 5 nm. For example, about 0.5 nm to about 2 nm. to about 5 nm. When the thickness of the electron injection layer is within the above range, the electron injection layer can have satisfactory electron injection characteristics without significantly increasing a driving voltage.
[0477] The second electrode 190
[0478] The second electrode 190 is located on the organic layer 150. The second electrode 190 can be a cathode (as an electron injection electrode), in which case the material used to form the second electrode 190 can be selected from metals, alloys, conductive compounds, and any combination thereof all having a relatively low work function.
[0479] The second electrode 190 can include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but embodiments of the present disclosure are not limited thereto. The second electrode 190 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0480] The second electrode 190 can have a single layer structure or a multi-layer structure including two or more layers.
[0481] The organic light emitting device 10 can further include a capping layer positioned in a direction in which light is emitted.
[0482] According to a principle of constructive interference, the capping layer can improve external light emitting efficiency of the device.
[0483] The capping layer can have a refractive index of about 1.6 or more with respect to a wavelength of about 589 nm.
[0484] The capping layer can be an organic capping layer composed of an organic material, an inorganic capping layer composed of an inorganic material, or a composite capping layer including an organic material and an inorganic material.
[0485] The capping layer can include at least one material selected from a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, and an alkaline earth metal complex. The carbocyclic compound, the heterocyclic compound, and the amine-based compound can each be optionally substituted with a substituent including at least one element selected from oxygen (O), nitrogen (N), sulfur (S), selenium (Se), silicon (Si), fluorine (F), chlorine (Cl), bromine (Br), and iodine (I). In one embodiment, the capping layer can include an amine-based compound.
[0486] In one embodiment, the capping layer can include a compound represented by Formula 201 or a compound represented by Formula 202.
[0487] In one or more embodiments, the capping layer can include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but embodiments of the present disclosure are not limited thereto:
[0488] In the above, an organic light emitting device has been described with reference to Figure 1 but embodiments of the present disclosure are not limited thereto.
[0489] Each of the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region can be formed in a set or predetermined region 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 (LITI).
[0490] When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are formed by vacuum deposition, vacuum deposition can be performed at a deposition temperature of about 100°C to about 500°C, a vacuum degree of about 10 -8 -3 tor to about 10 tor, and a deposition rate of about / second to about
[0491] When the layers constituting the hole transport region, the emission layer, and the layers 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 at a heat treatment temperature of about 80°C to about 200°C, according to the materials to be included and the structure of the layers to be formed.
[0492] Full-color organic light-emitting device
[0493] Figure 3 is a schematic cross-sectional view of an organic light-emitting device 20 according to an embodiment.
[0494] Although the substrate 201 is described, other substrates or variations thereof can be used. In some embodiments, for example, a thin film transistor including a source electrode, a drain electrode, an active layer, a buffer layer, and an organic insulating layer can be further located between the substrate 201 and the first pixel electrode 211, the second pixel electrode 212, and the third pixel electrode 213.
[0495] Figure 3 The organic light-emitting device 20 of FIG. 1 includes a first emission region, a second emission region, and a third emission region.
[0496] The organic light-emitting device 20 includes a first pixel electrode 211, a second pixel electrode 212, and a third pixel electrode 213 located in the first emission region, the second emission region, and the third emission region, respectively.
[0497] The first pixel electrode 211, the second pixel electrode 212, and the third pixel electrode 213 are the same as described in the present specification in connection with the first electrode 110.
[0498] The first pixel electrode 211, the second pixel electrode 212, and the third pixel electrode 213 can each be electrically connected with any one of the source electrode and the drain electrode of the thin film transistor.
[0499] The organic light emitting device 20 includes a counter electrode 290 facing the first pixel electrode 211, the second pixel electrode 212, and the third pixel electrode 213.
[0500] An organic layer is located between the counter electrode 290 and the first pixel electrode 211, the second pixel electrode 212, and the third pixel electrode 213. The organic layer includes a hole injection layer 220, a hole transport layer 230, emission layers 251, 252, and 253, an electron transport layer 260, and an electron injection layer 270. Although not shown in FIG. 2, an emission auxiliary layer can be located between the hole transport layer 230 and the first emission layer 251, between the hole transport layer 230 and the second emission layer 252, and / or between the hole transport layer 230 and the third emission layer 253. Figure 3
[0501] A pixel defining film 205 is formed on edge portions of the first pixel electrode 211, the second pixel electrode 212, and the third pixel electrode 213. The pixel defining film 205 defines each pixel area, and can include or can be formed of any suitable organic insulating material (e.g., a silicon-based material), inorganic insulating material, or organic / inorganic composite insulating material.
[0502] The hole injection layer 220 and the hole transport layer 230 can be sequentially formed as a common layer on the first pixel electrode 211, the second pixel electrode 212, and the third pixel electrode 213.
[0503] The hole injection layer 220 and the hole transport layer 230 can be the same as described in this specification in connection with the organic light emitting device 10.
[0504] The first emission layer 251 can be positioned to correspond to a first emission area to emit first color light, the second emission layer 252 can be positioned to correspond to a second emission area to emit second color light, and the third emission layer 253 can be positioned to correspond to a third emission area to emit third color light, the first emission layer 251, the second emission layer 252, and the third emission layer 253 each being formed on the hole transport layer 230.
[0505] The electron transport layer 260, the electron injection layer 270, and the counter electrode 290 can be sequentially formed as a common layer with respect to the first emission area, the second emission area, and the third emission area.
[0506] The electron transport layer 260 and the electron injection layer 270 can be the same as described in this specification in connection with the organic light emitting device 10. The counter electrode 290 can be the same as described in this specification in connection with the second electrode 190.
[0507] A capping layer 300 is positioned on the counter electrode 290. The capping layer 300 can include or be formed of the organic material and / or the inorganic material described above. In one or more embodiments, the capping layer 300 can include a compound selected from the group consisting of Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but embodiments of the present disclosure are not limited thereto.
[0508] The capping layer 300 can contribute to efficient emission of light generated from the organic light-emitting device 20, and can protect the organic light-emitting device 20.
[0509] The maximum emission wavelength of the first color light and the maximum emission wavelength of the second color light can each be greater than the maximum emission wavelength of the third color light.
[0510] The first color light can be red light, the second color light can be green light, and the third color light can be blue light, but embodiments of the present disclosure are not limited thereto. Thus, the organic light-emitting device 20 can emit full-color light. However, the first color light, the second color light, and the third color light are not limited to the above, as long as the mixed color light can be white light.
[0511] In one or more embodiments, the maximum emission wavelength of the first color light can be about 620 nm to about 750 nm, the maximum emission wavelength of the second color light can be about 495 nm to about 570 nm, and the maximum emission wavelength of the third color light can be about 430 nm to about 495 nm, but embodiments of the present disclosure are not limited thereto.
[0512] At least two of the first emission layer 251, the second emission layer 252, and the third emission layer 253 can include a host including a first compound and a second compound, and a dopant, wherein the first compound, the second compound, and the dopant are different from each other.
[0513] The two host compounds having different HOMO and LUMO energy levels in the emission layer form an excimer, and a difference (△E 激基复合物 ) between the HOMO and LUMO energy levels of the excimer can be greater than a difference (△E 掺杂剂 ) between the HOMO and LUMO energy levels of the dopant.
[0514] The first compound, the second compound, and the dopant can each be the same as described in connection with the organic light-emitting device 10.
[0515] In one embodiment, the second compound can be a host having an electron transport ability smaller than that of the first compound.
[0516] In one embodiment, two of the first emission layer 251, the second emission layer 252, and the third emission layer 253 can each include two hosts (i.e., the first compound and the second compound) and a dopant, and in some embodiments, the first emission layer 251, the second emission layer 252, and the third emission layer 253 can each include two hosts (the first compound and the second compound) and a dopant.
[0517] In one embodiment, at least one of the first emission layer 251, the second emission layer 252, and the third emission layer 253 can further include a third compound different from the first compound and the second compound.
[0518] In one embodiment, at least one of the first emission layer 251, the second emission layer 252, and the third emission layer 253 can further include two or more hosts each different from the first compound and the second compound.
[0519] When N different hosts are included in the emission layer, the emission layer can include the first compound to the Nth compound.
[0520] For example, at least one of the first emission layer 251, the second emission layer 252, and the third emission layer 253 of the organic light emitting device 20 can include one of the following combinations:
[0521] i) the first compound, the second compound, and the dopant;
[0522] ii) the first compound, the second compound, the third compound, and the dopant; and
[0523] iii) the first compound, the second compound, the third compound, …, the N-1th compound, the Nth compound, and the dopant.
[0524] In Figure 3 In the above-described embodiment, the organic light emitting device 20 including the pixel defining film 205, the hole injection layer 220, the hole transport layer 230, the electron transport layer 260, and the electron injection layer 270 is illustrated, but various suitable modifications are possible, for example, at least one of the described layers can be omitted.
[0525] The device
[0526] The organic light emitting device can be included in various suitable devices.
[0527] One or more example embodiments of the present disclosure provide a device including an organic light emitting device.
[0528] The device can be, for example, a light emitting device, an authentication device, or an electronic device, but embodiments of the present disclosure are not limited thereto.
[0529] The light emitting apparatus can be used as any suitable display, light source, etc.
[0530] The authentication apparatus can be, for example, a biometric authentication apparatus for authenticating an individual using biometric information of a biometric object (e.g., a fingertip, a pupil, etc.).
[0531] The authentication apparatus can include a biometric information collector in addition to the organic light emitting device.
[0532] The electronic apparatus can be applied to a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic notebook, an electronic dictionary, an electronic game machine, a medical instrument (e.g., an electronic thermometer, a blood pressure meter, a blood sugar meter, a pulse measurement device, a pulse wave measurement device, an electrocardiogram (ECG) display, an ultrasonic diagnostic device, or an endoscope display), a fish finder, various measuring instruments, a meter (e.g., a meter for a vehicle, an airplane, and a ship), a projector, etc., but embodiments of the present disclosure are not limited thereto.
[0533] In one embodiment, the apparatus can include a thin film transistor in addition to the organic light emitting device. Here, the thin film transistor includes a source electrode, an active layer, and a drain electrode, and the first electrode or the pixel electrode of the organic light emitting device can be in electrical contact (e.g., electrically connected) with one of the source electrode and the drain electrode of the thin film transistor.
[0534] General definitions of substituents
[0535] The term "C1-C 60 alkyl" as used herein refers to a straight-chain or branched-chain aliphatic saturated hydrocarbon monovalent radical having from 1 to 60 carbon atoms, non-limiting examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, and hexyl. The term "C1-C 60 alkylene" as used herein refers to a divalent radical having essentially the same structure as a C1-C 60 alkyl group.
[0536] The term "C2-C 60 alkenyl" as used herein refers to a hydrocarbyl group having at least one carbon-carbon double bond in the middle or at the end of a C2-C 60 alkyl group. The term "C2-C 60 alkenylene" as used herein refers to a divalent radical having essentially the same structure as a C2-C 60 alkenyl group.
[0537] The term "C2-C 60 alkynyl" as used herein refers to a hydrocarbyl group having at least one carbon-carbon triple bond in the middle or at the end of a C2-C 60A hydrocarbon group having at least one carbon-carbon triple bond at the middle or end of an alkyl group, non-limiting examples of which include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in conjunction with this. 60 "Immyneyl" refers to a group with a C2-C group. 60 The alkynyl group is a divalent group with a basically the same structure.
[0538] As used herein, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and non-limiting examples include methoxy, ethoxy, and isopropoxy.
[0539] As used herein, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also used. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with essentially the same structure as cycloalkyl groups.
[0540] As used herein, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom and 1 to 10 carbon atoms, with non-limiting examples including 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with essentially the same structure as heterocyclic alkyl groups.
[0541] As used herein, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms in its ring, at least one carbon-carbon double bond, and not being aromatic; non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also used. 10 "Biopylidene alkenyl" refers to a group that has a similar structure to C3-C4. 10 A divalent group with a structure that is essentially the same as a cycloalkenyl group.
[0542] As used herein, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom, one to ten carbon atoms, and at least one double bond in its ring. C1-C 10Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-l,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. The term "C1-C 10 heterocycloalkenyl" refers to a divalent group having essentially the same structure as a C1-C 10 heterocycloalkenyl group.
[0543] The term "C6-C 60 aryl" refers to a monovalent radical having a carbocyclic aromatic ring system including 6 to 60 carbon atoms, and the term "C6-C 60 arylene" refers to a divalent radical having a carbocyclic aromatic ring system including 6 to 60 carbon atoms. C6-C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluorenyl, and group. When C6-C 60 aryl and C6-C 60 When both the aryl and C6-C
[0544] The term "C1-C 60 heteroaryl" refers to a monovalent radical having a heterocyclic aromatic ring system having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to 1 to 60 carbon atoms. The term "C1-C 60 heteroarylene" refers to a divalent radical having a heterocyclic aromatic ring system having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to 1 to 60 carbon atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, and isoquinolinyl. When C1-C 60 heteroaryl and C1-C 60 When both the heteroaryl and C1-C
[0545] The term "C6-C 60 aryloxy" refers to -OA 102 (wherein A 102 is C6-C 60 aryl), the term "C6-C 60 arylthio" refers to -SA 103 (wherein A 103 is C6-C 60 aryl).
[0546] The term "monovalent non-aromatic condensed polycyclic group" as used herein refers to a monovalent group having two or more rings condensed with each other, only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring-forming atoms, and no aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic condensed polycyclic group include adamantyl group. The term "divalent non-aromatic condensed polycyclic group" as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
[0547] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein refers to a monovalent group having two or more rings condensed with each other, at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and no aromaticity in its entire molecular structure. Non-limiting examples of monovalent non-aromatic condensed heteropolycyclic group include azepanyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0548] The term "C5-C 60 Cycloalkyl" refers to a monocyclic or polycyclic group including only carbon as ring-forming atoms and consisting of 5 to 60 carbon atoms. C5-C 60 Cycloalkyl group can be aromatic cycloalkyl group or non-aromatic cycloalkyl group. C5-C 60 Cycloalkyl group can be a ring (such as benzene), a monovalent group (such as phenyl), or a divalent group (such as phenylene). In one or more embodiments, depending on the number of substituents attached to C5-C 60 Cycloalkyl group can be a trivalent group or a tetravalent group. 60 Cycloalkyl group can be a trivalent group or a tetravalent group.
[0549] The term "C1-C 60 Heterocyclyl" refers to a group having substantially the same structure as C5-C 60 Cycloalkyl group except that at least one heteroatom selected from N, O, Si, P, and S is used as ring-forming atoms in addition to carbon (the number of carbon atoms can be 1 to 60).
[0550] In this specification, substituted C5-C 60 Cycloalkyl group, substituted C1-C 60 Heterocyclyl group, substituted C1-C 20 Alkylene group, substituted C2-C 20 Alkenylene group, substituted C3-C 10 Cycloalkylene group, substituted C1-C 10 Heterocycloalkylene group, substituted C3-C 10 Cycloalkenylene group, substituted C1-C 10heterocycloalkenyl, substituted C6-C 60 arylene, substituted C1-C 60 heteroarylene, substituted bivalent non-aromatic condensed polycyclic group, substituted bivalent non-aromatic condensed heteropolycyclic group, substituted C1-C 60 alkyl, substituted C2-C 60 alkenyl, substituted C2-C 60 alkynyl, substituted C1-C 60 alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 heterocycloalkyl, substituted C3-C 10 cycloalkenyl, substituted C1-C 10 heterocycloalkenyl, substituted C6-C 60 aryl, substituted C6-C 60 aryloxy, substituted C6-C 60 aralkylthio, substituted C1-C 60 heteroaryl, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group can be selected from:
[0551] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 alkoxy;
[0552] all of which are substituted with from one to five substituents selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 aralkylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ) and -P(=O)(Q 11(Q) 12 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;
[0553] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;
[0554] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 ) and -P(=O)(Q 21 (Q) 22 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic; and
[0555] -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 ),
[0556] Among them, 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, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl.
[0557] As used herein, the term "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, and "tert-Bu" or "Bu" refers to tert-Bu. t "Refers to tert-butyl, as the term "OMe" used herein refers to methyl methacrylate (MMA).
[0558] As used herein, the term "biphenyl" refers to a phenyl group that has a substituted phenyl group. For example, "biphenyl" is a phenyl group with a C6-C substituted phenyl group. 60 Aryl groups are substituted phenyl groups.
[0559] The term "triphenyl" as used herein refers to "a phenyl substituted with a biphenyl group". For example, "triphenyl" is a phenyl group having a C6-C12biphenyl group substituted at the 4-position. 60 C6-C12aryl group substituted at the 4-position. 60 C6-C12aryl group substituted at the 4-position.
[0560] Unless otherwise defined, and as used herein, and and' each refer to the bond to the adjacent atom in the corresponding formula.
[0561] Hereinafter, an organic light emitting device according to an embodiment will be described in more detail with reference to examples.
[0562] Examples
[0563] Evaluation Example 1: Evaluation of HOMO and LUMO Energy Levels
[0564] The HOMO and LUMO energy levels of the compounds C1 to C12 used in Examples 1-1 to 1-11, Examples 2-1 to 2-10, and Examples 3-1 to 3-4, the compounds HA1 to HA6 used in Comparative Examples 1-1 to 1-4, Comparative Examples 2-1 to 2-3, and Comparative Examples 3-1 to 3-4, and the compounds PRD, PGD, and FBD were measured by cyclic voltammetry, the results of which are shown in Table 1.
[0565] Table 1
[0566]
[0567]
[0568] Red Device Preparation Example
[0569] Example 1-1
[0570] 15 Ω / cm2hole transport layer (HTL) material available from Corning, was deposited on the ITO glass substrate to a thickness of 110 nm to form a hole injection layer (HIL). The hole injection layer was then coated with a 10 nm thick layer of NPB to form a hole transport layer (HTL). 2 An ITO glass substrate (anode) was cut to a size of 50 mm x 50 mm x 0.5 mm, cleaned with acetone, isopropanol, and ultrapure water each for 15 minutes, and then cleaned by ultraviolet irradiation and exposure to ozone for 30 minutes. Then, the ITO glass substrate was provided to a vacuum deposition apparatus.
[0571] On the ITO glass substrate, m-MTDATA was deposited to form a hole injection layer having a thickness of 110 nm, and NPB was deposited on the hole injection layer to form a hole transport layer having a thickness of 10 nm, thereby completing the formation of a hole transport region.
[0572] The host and the dopant were co-deposited on the hole transport region so that the concentration of the dopant in the host was 2 wt%, thereby forming an emission layer having a thickness of 45 nm. As the host, the first compound (C1) and the second compound (C2) were co-deposited at deposition rates of 25 nm / min and 20 nm / min, respectively, using compound PRD as the dopant.
[0573] On the emission layer, BAlq was deposited to form a hole blocking layer having a thickness of 10 nm, and then, Alq3 and LiQ were co-deposited thereon to form an electron transport layer having a thickness of 30 nm.
[0574] On the electron transport layer, LiF was deposited to form an electron injection layer having a thickness of 1.3 nm, and then, Al was deposited thereon to form a cathode having a thickness of 200 nm. On the cathode, HT28 was deposited to form a cap layer having a thickness of 60 nm, thereby completing the manufacture of the organic light emitting device.
[0575]
[0576] Examples 1-2 to 1-11 and Comparative Examples 1-1 to 1-4
[0577] An additional organic light emitting device was manufactured in substantially the same manner as Example 1-1, except that the host compound and the dopant compound shown in Table 2 were used in forming the emission layer.
[0578] Evaluation Example 2: Red Device Evaluation Example
[0579] For each of the organic light emitting devices manufactured according to Examples 1-1 to 1-11 and Comparative Examples 1-1 to 1-4, the driving voltage (V), the efficiency (cd / A), and the lifespan (LT 2 ) at a current density of 10 mA / cm 97 were measured, and the results are shown in Table 2. The driving voltage and the current density of the organic light emitting device were measured using a source meter (manufactured by Keithley Instruments, Inc., 2400 series).
[0580] Table 2
[0581]
[0582]
[0583]
[0584]
[0585] It is confirmed from Table 2 that the organic light-emitting devices according to Examples 1-1 to 1-11 have low driving voltage, high efficiency, and long lifespan compared to the organic light-emitting devices according to Comparative Examples 1-1 to 1-4.
[0586] Green device preparation examples
[0587] Examples 2-1 to 2-10 and Comparative Examples 2-1 to 2-3
[0588] Another organic light-emitting device was manufactured in substantially the same manner as Example 1-1, except that the host compound and dopant compound shown in Table 3 were used in forming the emission layer.
[0589] Evaluation Example 3: Green device evaluation example
[0590] For each of the organic light-emitting devices according to Examples 2-1 to 2-10 and Comparative Examples 2-1 to 2-3, the driving voltage (V), efficiency (cd / A), and lifespan (LT 2 ) at a current density of 10 mA / cm 97 were measured, and the results are shown in Table 3. The driving voltage and current density of the organic light-emitting device were measured using a source meter (manufactured by Keithley Instruments, Inc., 2400 series).
[0591] Table 3
[0592]
[0593]
[0594]
[0595]
[0596] It is confirmed from Table 3 that the organic light-emitting devices according to Examples 2-1 to 2-10 have low driving voltage, high efficiency, and long lifespan compared to the organic light-emitting devices according to Comparative Examples 2-1 to 2-3.
[0597] Blue device preparation examples
[0598] Examples 3-1 to 3-4 and Comparative Examples 3-1 to 3-4
[0599] Another organic light-emitting device was manufactured in substantially the same manner as Example 1-1, except that the host compound and dopant compound shown in Table 4 were used in forming the emission layer.
[0600] Evaluation Example 4: Blue device evaluation example
[0601] For each of the organic light emitting devices manufactured according to Examples 3-1 to 3-4 and Comparative Examples 3-1 to 3-4, the driving voltage (V), efficiency (cd / A), and lifespan (LT 2 ) at a current density of 10 mA / cm 97 were measured, and the results are shown in Table 4. The driving voltage and current density of the organic light emitting device were measured using a source meter (manufactured by Keithley Instruments, Inc., 2400 series).
[0602] Table 4
[0603]
[0604]
[0605]
[0606] From Table 4, it is confirmed that the organic light emitting devices manufactured according to Examples 3-1 to 3-4 have a low driving voltage, high efficiency, and long lifespan compared to the organic light emitting devices manufactured according to Comparative Examples 3-1 to 3-4.
[0607] The organic light emitting device according to an embodiment of the disclosure can have a low driving voltage, high efficiency, and long lifespan.
[0608] As used herein, the terms "substantially," "approximately," and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art.
[0609] Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed in the recited range. For example, a range of "1.0 to 10.0" is intended to include all sub-ranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, the applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed in the ranges expressly recited in this specification.
[0610] It is to be understood that the embodiments described herein are to be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as being applicable to other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the attached drawings, it will be apparent to those of ordinary skill in the art that changes in form and details can be made therein without departing from the spirit and scope as defined by the following 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 including an emission layer, wherein the emission layer includes a host and a dopant, the host includes a first compound and a second compound, the first compound, the second compound, and the dopant are different from each other, two compounds included in the host in the emission layer have different highest occupied molecular orbital energy levels and lowest unoccupied molecular orbital energy levels, form an exciplex, and a difference between a highest occupied molecular orbital energy level and a lowest unoccupied molecular orbital energy level of the exciplex is larger than a difference between a highest occupied molecular orbital energy level and a lowest unoccupied molecular orbital energy level of the dopant, the first compound and the second compound are each independently selected from compounds represented by Formulae 1 to 3-1: Formula 1 Formula 2 Formula 3-1 wherein, in Formulae 1 to 3-1, CY1 is a group represented by Formula 2A, and CY2 is a group represented by Formula 2B, X 11 N[(L 11 ) a11 -(R 11 ) b11 ], X 21 is O, S, N[(L 21 ) a21 -(R 21 ) b21 ], Y1to Y8are each independently N or C(R 14 ), wherein, when C(R 14 ) is two or more, two or more R 14 are the same as or different from each other, Y 11 to Y 18 each independently C(R 24 ), wherein, when C(R 24 ) is two or more, two or more R 24 are the same or different from each other, a11 to a13, a21 to a24, a31, and a32 are each independently an integer of 0 to 2, In Formula 2A, C* and C** are each a carbon condensed with a 5-membered ring containing X 21 , and C is a carbon not condensed with a 5-membered ring containing X In Equation 2A, Y 19 To Y 22 Each is independently C(R) 25 ), where, when C(R) 25 When there are two or more R, two or more R 25 They are the same or different from each other, and Y 19 To Y 22 Both adjacent groups are related to X. 22 The carbon condensation of a 5-membered ring, In formula 2B, X 22 is O, S, N[(L 24 ) a24 -(R 26 ) b26 ], L 11 to L 13 , L 21 to L 24 , L 31 and L 32 are each independently phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, diphenzocarbazolylene, dibenzosilolylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, and isoquinolinylene, b11 to b13, b21 to b23, b26, b31, b32, and b33 are each independently an integer of 1 to 5, R 11 to R 14 , R 11a , R 11b , R 21 to R 26 , R 21a , R 21b , R 26a , R 26b , R 31 , R 32 and R 33 are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, unsubstituted C1-C 60 alkyl, unsubstituted C2-C 60 alkenyl, unsubstituted C2-C 60 alkynyl, unsubstituted C1-C 60 alkoxy, unsubstituted C3-C 10 cycloalkyl, unsubstituted C1-C 10 heterocycloalkyl, unsubstituted C3-C 10 cycloalkenyl, unsubstituted C1-C 10 heterocycloalkenyl, unsubstituted C6-C 60 aryl, unsubstituted C6-C 60 aryloxy, unsubstituted C6-C 60 arylthio, unsubstituted C1-C 60 heteroaryl, unsubstituted monovalent non-aromatic condensed polycyclic group, unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), Q1to Q3are each independently selected from the group consisting of hydrogen, deuterium, C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, R 11 to R 14 , R 11a and R 11b two adjacent groups among them are optionally linked together by a linker selected from a single bond, *-O-*', *-S-*', *-B(R 15 )-*', *-N(R 15 )-*', *-C(R 15 )(R 16 )-*', *-C(R 15 )=C(R 16 )-*', C5-C 30 carbocyclyl and C1-C 30 heterocyclyl, R 21 to R 26 , R 21a , R 21b , R 26a and R 26b two adjacent groups among them are optionally linked together by a linker selected from a single bond, *-O-*', *-S-*', *-B(R 27 )-*', *-N(R 27 )-*', *-C(R 27 )(R 28 )-*', *-C(R 27 )=C(R 28 )-*', C5-C 30 carbocyclyl and C1-C 30 heterocyclyl, R 15 , R 16 , R 27 and R 28 are each independently selected from the group consisting of hydrogen, C1-C 20 alkyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and substituted with at least one member selected from the group consisting of deuterium, C1-C 20 phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, n1, n2, n21, and n22 are each independently an integer of 1 to 4, and * and *' each represent a binding site to an adjacent atom. the second compound has a smaller electron-transporting ability than the first compound.
2. The organic light-emitting device according to claim 1, wherein the first compound and the second compound form the exciplex.
3. The organic light emitting device according to claim 1, wherein, 4. The organic light-emitting device according to claim 1, wherein: the first compound and the second compound form the exciplex, and i) the first compound and the second compound each include an electron-transporting moiety, ii) the first compound and the second compound each do not include an electron-transporting moiety, or iii) the first compound includes an electron-transporting moiety, and the second compound does not include an electron-transporting moiety. the first compound is an electron-transporting host, and 5. The organic light emitting device according to claim 1, wherein, the second compound is a hole-transporting host. the first compound and the second compound are each independently selected from Compounds C1 to C12:
6. The organic light emitting device according to claim 1, wherein, the first compound and the second compound each have a higher triplet energy level than the dopant.
7. The organic light emitting device according to claim 1, wherein, a weight ratio of the first compound to the second compound is 90:10 to 10:
90.
8. The organic light emitting device according to claim 1, wherein, the host further includes a third compound, and 9. The organic light emitting device of claim 1, wherein, the first compound, the second compound, the third compound, and the dopant are different from each other. the third compound is an electron-transporting host, a hole-transporting host, or a bipolar host.
10. The organic light emitting device according to claim 9, wherein, the emission layer further includes two or more hosts, the emission layer includes a total of N hosts, where N is an integer of 4 or more, and 11. The organic light emitting device according to claim 1, wherein, the two or more hosts, the first compound, the second compound, and the dopant are different from each other. the exciplex has an energy band gap of 2.5 eV to 3.5 eV.
12. The organic light emitting device according to claim 1, wherein, the dopant is a phosphorescent dopant or a fluorescent dopant.
13. The organic light emitting device according to claim 1, wherein, 14. The organic light emitting device according to claim 1, wherein, The organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, The hole transport region includes at least one selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer, and The electron transport region includes 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.
15. The organic light emitting device of claim 14, wherein, The hole transport region includes an arylamine compound.
16. The organic light emitting device of claim 14, wherein, The electron transport region includes a metal-free compound including at least one nitrogen-containing ring having a poor π electron. 17.An organic light emitting device, the organic light emitting device comprising: a first pixel electrode, a second pixel electrode, and a third pixel electrode in a first emission region, a second emission region, and a third emission region, respectively; a counter electrode facing the first pixel electrode, the second pixel electrode, and the third pixel electrode; and an organic layer between the first pixel electrode, the second pixel electrode, and the third pixel electrode and the counter electrode, and including an emission layer, wherein the emission layer includes: a first emission layer corresponding to the first emission region and emitting a first color light; a second emission layer corresponding to the second emission region and emitting a second color light; and a third emission layer corresponding to the third emission region and emitting a third color light, wherein a maximum emission wavelength of the first color light and a maximum emission wavelength of the second color light are both greater than a maximum emission wavelength of the third color light, at least two emission layers selected from the first emission layer, the second emission layer, and the third emission layer include a host including a first compound and a second compound and a dopant, the first compound, the second compound, and the dopant are different from each other, two compounds included in the host in the emission layer have different highest occupied molecular orbital energy levels and lowest unoccupied molecular orbital energy levels, form an exciplex, and a difference between a highest occupied molecular orbital energy level and a lowest unoccupied molecular orbital energy level of the exciplex is greater than a difference between a highest occupied molecular orbital energy level and a lowest unoccupied molecular orbital energy level of the dopant, the first compound and the second compound are each independently selected from compounds represented by Formulae 1 to 3-1: Formula 1 Formula 2 Formula 3-1 wherein, in Formulae 1 to 3-1, CY1 is a group represented by Formula 2A, and CY2 is a group represented by Formula 2B, X 11 N[(L 11 ) a11 -(R 11 ) b11 ], X 21 is O, S, N[(L 21 ) a21 -(R 21 ) b21 ], Y1to Y8are each independently N or C(R 14 ), wherein, when C(R 14 ) is two or more, two or more R 14 are the same as or different from each other, Y 11 to Y 18 are each independently C(R 24 ), wherein, when C(R 24 ) is two or more, two or more R 24 are the same or different from each other, a11 to a13, a21 to a24, a31, and a32 are each independently an integer of 0 to 2, In Formula 2A, C* and C** are each a carbon condensed with a 5-membered ring containing X 21 , and C is a carbon not condensed with a 5-membered ring containing X In Equation 2A, Y 19 To Y 22 Each is independently C(R) 25 ), where, when C(R) 25 When there are two or more R, two or more R 25 They are the same or different from each other, and Y 19 To Y 22 Both adjacent groups are related to X. 22 The carbon condensation of a 5-membered ring, In formula 2B, X 22 is O, S, N[(L 24 ) a24 -(R 26 ) b26 ], L 11 to L 13 , L 21 to L 24 , L 31 and L 32 are each independently phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthrylene, fluoranthrylene, phenanthro[9,10]phenanthrylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, diphenzocarbazolylene, dibenzosilolylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolinylene, and isoquinolinylene, b11 to b13, b21 to b23, b26, b31, b32, and b33 are each independently an integer of 1 to 5, R 11 to R 14 , R 11a , R 11b , R 21 to R 26 , R 21a , R 21b , R 26a , R 26b , R 31 , R 32 and R 33 are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, unsubstituted C1-C 60 alkyl, unsubstituted C2-C 60 alkenyl, unsubstituted C2-C 60 alkynyl, unsubstituted C1-C 60 alkoxy, unsubstituted C3-C 10 cycloalkyl, unsubstituted C1-C 10 heterocycloalkyl, unsubstituted C3-C 10 cycloalkenyl, unsubstituted C1-C 10 heterocycloalkenyl, unsubstituted C6-C 60 aryl, unsubstituted C6-C 60 aryloxy, unsubstituted C6-C 60 arysthio, unsubstituted C1-C 60 heteroaryl, unsubstituted monovalent non-aromatic condensed polycyclic group, unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2), Q1to Q3are each independently selected from the group consisting of hydrogen, deuterium, C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, R 11 To R 14 R 11a and R 11b Two adjacent groups may optionally be connected via a single bond, *-O-*', *-S-*', or *-B(R) 15 )-*'、*-N(R 15 )-*'、*-C(R 15 (R) 16 )-*'、*-C(R 15 )=C(R 16 )-*'、C5-C 30 Carbocyclic groups and C1-C 30 The linking groups of the heterocyclic groups are connected together. R 21 To R 26 R 21a R 21b R 26a and R 26b Two adjacent groups may optionally be connected via a single bond, *-O-*', *-S-*', or *-B(R) 27 )-*'、*-N(R 27 )-*'、*-C(R 27 (R) 28 )-*'、*-C(R 27 )=C(R 28 )-*'、C5-C 30 Carbocyclic groups and C1-C 30 The linking groups of the heterocyclic groups are connected together. R 15 , R 16 , R 27 , and R 28 are each independently selected from the group consisting of hydrogen, C1-C 20 alkyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and substituted with at least one member selected from the group consisting of deuterium, C1-C 20 phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, n1, n2, n21, and n22 are each independently an integer of 1 to 4, and * and *' each represent a bonding site to an adjacent atom. The second compound has a smaller electron transport ability than the first compound.
18. The organic light emitting device of claim 17, wherein, 19. The organic light emitting device of claim 17, wherein, The at least one emission layer selected from the first emission layer, the second emission layer and the third emission layer further comprises a third compound different from the first compound and the second compound.
20. A device comprising a thin film transistor and an organic light emitting device according to any one of claims 1 to 19, the thin film transistor comprising a source electrode, a drain electrode and an active layer, wherein, The first electrode of the organic light emitting device is electrically connected with one selected from the source electrode and the drain electrode of the thin film transistor.
Citation Information
Patent Citations
Short circuit protection device to prevent short circuit due to growth of lead plate
KR1020200040483A