Light-emitting devices
By adopting the emission layer structure and buffer layer energy level matching design of three or more main bodies in organic light emitting devices, the problems of high driving voltage and unstable electron transmission in the prior art are solved, and the device efficiency and life are improved.
Patent Information
- Application Number
- CN202011555504.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-04-06
- Filing Date
- 2020-12-24
- Publication Date
- 2025-09-02
- Estimated Expiration
- 2040-12-24
AI Technical Summary
The organic light emitting devices in the prior art have high emitting layer resistance, which leads to the device characteristics mainly determined by the emitting layer characteristics, making it difficult to improve efficiency and life at the same time. Especially in a single body or two body structures, there are problems such as high driving voltage and unstable electron transmission.
The emission layer structure including three or more bodies is adopted, combined with the hole transmission area and the electron transmission area, and the buffer layer is set so that the lowest unoccupied molecular orbital energy level of the electron transmission area is equal to the energy level of the buffer layer, eliminating the potential barrier between the body and the buffer layer, and improving electron transmission stability.
The performance improvement of the light emitting device is achieved, reducing the driving voltage and improving the smooth transmission of electrons, thereby improving the efficiency and life of the device.
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Figure CN113497193B_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0041614, filed on April 6, 2020, which is hereby incorporated by reference for all purposes as if fully set forth herein. Technical Field
[0002] Exemplary embodiments of the invention relate generally to a light emitting device, and more particularly, to an electronic device including the light emitting device. Background Art
[0003] Compared with devices in the field, light-emitting devices are self-emitting devices with wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed. In the light-emitting device, a first electrode is provided on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers (such as holes and electrons) recombine in the emission layer to generate light.
[0004] The above information disclosed in this Background section is only for understanding the background of the inventive concept and therefore it may contain information that does not constitute the prior art. Summary of the Invention
[0005] Light emitting devices and electronic devices including the same constructed according to the principles and exemplary embodiments of the invention have both improved efficiency and improved lifespan.
[0006] Additional features of the inventive concepts will be set forth in the description which follows, and in part will be apparent from the description, or may be learned by practice of the inventive concepts.
[0007] According to one aspect of the invention, a light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an intermediate layer arranged between the first electrode and the second electrode and having an emission layer, wherein the intermediate layer includes: i) a hole transport region arranged between the first electrode and the emission layer; and ii) an electron transport region arranged between the emission layer and the second electrode; wherein: the emission layer includes three or more hosts; the electron transport region includes a buffer layer; the three or more hosts include a hole transport host, a first electron transport host and a second electron transport host; the buffer layer includes a third electron transport host; and the lowest unoccupied molecular orbital energy level of the second electron transport host is substantially equal to the lowest unoccupied molecular orbital energy level of the third electron transport host.
[0008] The first electrode may include an anode, the second electrode may include a cathode, and the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
[0009] The first electrode may include an anode, the second electrode may include a cathode, and the electron transport region may further include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0010] A highest occupied molecular orbital energy level of the second electron transport host may be substantially equal to a highest occupied molecular orbital energy level of the third electron transport host.
[0011] The lowest unoccupied molecular orbital energy level of the hole transport host, the lowest unoccupied molecular orbital energy level of the first electron transport host, and the lowest unoccupied molecular orbital energy level of the second electron transport host may satisfy the following inequalities (1) and (2):
[0012] |E LUMO_HT |>|E LUMO_ET1 | (1); and
[0013] |E LUMO_HT |>|E LUMO_ET2 | (2),
[0014] Among them, E LUMO_HT represents the lowest unoccupied molecular orbital energy level of the hole transport host, E LUMO_ET1 represents the lowest unoccupied molecular orbital energy level of the first electron transport host, and E LUMO_ET2 represents the lowest unoccupied molecular orbital energy level of the second electron-transporting host.
[0015] The highest occupied molecular orbital energy level of the hole transport host, the highest occupied molecular orbital energy level of the first electron transport host, and the highest occupied molecular orbital energy level of the second electron transport host may satisfy the following inequality (3):
[0016] |E HOMO_ET2 |>|E HOMO_ET1 |>|E HOMO_HT | (3),
[0017] Among them, E HOMO_ET2 represents the highest occupied molecular orbital energy level of the second electron transport host, E HOMO_ET1 represents the highest occupied molecular orbital energy level of the first electron transport host, and E HOMO_HT Represents the highest occupied molecular orbital energy level of the hole-transporting host.
[0018] The lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the first electron transport host and the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the second electron transport host may satisfy the following inequalities (4) and (5):
[0019] |E LUMO_ET2 |>|E LUMO_ET1 | (4); and
[0020] |E HOMO_ET2 |>|E HOMO_ET1 | (5),
[0021] Among them, E LUMO_ET1 and E HOMO_ET1 represent the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the first electron transport host, respectively, and E LUMO_ET2 and E HOMO_ET2 represent the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the second electron transport host, respectively.
[0022] The lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the first electron transport host and the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the second electron transport host may satisfy the following inequalities (6) and (7):
[0023] |E LUMO_ET2 -E LUMO_ET1 |≤about 0.1eV (6); and
[0024] |E HOMO_ET2 -E HOMO_ET1 |≤about 0.1eV (7),
[0025] Among them, E LUMO_ET1 and E HOMO_ET1 represent the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the first electron transport host, respectively, and E LUMO_ET2 and E HOMO_ET2 represent the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the second electron transport host, respectively.
[0026] The second electron transport host and the third electron transport host may be the same compound.
[0027] The buffer layer may at least partially contact the emission layer.
[0028] The electron transport region may further include an electron transport layer, and the buffer layer may at least partially contact the electron transport layer.
[0029] The hole transport region may include an emission assisting layer, and the emission assisting layer may include a charge generating material.
[0030] The emission assisting layer may have a two-layer structure.
[0031] The hole transport region may include an emission assisting layer and a hole transport layer, and the emission assisting layer may at least partially contact the hole transport layer.
[0032] The hole transport layer may have a charge generating material.
[0033] The hole transport layer may have a two-layer structure.
[0034] The charge generating material may have a p-dopant.
[0035] The p-dopant may have a quinone derivative, a metal oxide, a cyano-containing compound, or any combination thereof, and may be HAT-CN or a compound represented by Formula 221:
[0036]
[0037] Formula 221
[0038]
[0039] Wherein, in formula 221,
[0040] R 221 to R 223 may be independently 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 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0041] The electronic device may include a thin film transistor and a light emitting device as defined above; wherein the thin film transistor may include a source electrode, a drain electrode, an active layer and a gate electrode, and the first electrode of the light emitting device may be electrically connected to one of the source electrode and the drain electrode of the thin film transistor.
[0042] It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the invention as claimed. BRIEF DESCRIPTION OF THE DRAWINGS
[0043] The accompanying drawings illustrate exemplary embodiments of the invention and together with the description serve to explain the inventive concept. The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification.
[0044] Figure 1 is a schematic cross-sectional view of an exemplary embodiment of a light emitting device constructed according to the principles of the invention. DETAILED DESCRIPTION
[0045] In the following description, for the purpose of explanation, many specific details are set forth to provide a thorough understanding of the various exemplary embodiments or implementations of the invention. As used herein, "embodiment" and "implementation" are interchangeable terms that are non-limiting examples of devices or methods that employ one or more of the inventive concepts disclosed herein. However, it is apparent that the various exemplary embodiments can be implemented without these specific details or with one or more equivalent arrangements. In other cases, in order to avoid making the various exemplary embodiments unnecessarily vague, well-known structures and devices are shown in block diagram form. In addition, the various exemplary embodiments may be different, but do not have to be exclusive. For example, without departing from the inventive concept, the specific shape, construction and characteristics of the exemplary embodiment may be used or implemented in another exemplary embodiment.
[0046] Unless otherwise indicated, the exemplary embodiments shown are to be understood as providing exemplary features of different details of some ways in which the inventive concept can be implemented in practice. Therefore, unless otherwise indicated, the features, components, modules, layers, films, panels, regions and / or aspects, etc. (hereinafter, individually or collectively referred to as "elements" or "elements") of the various embodiments may be further combined, separated, interchanged and / or rearranged without departing from the inventive concept.
[0047] The use of cross hatching and / or shading in the drawings is generally provided to make the boundaries between adjacent elements clear. As such, unless otherwise specified, the presence or absence of cross hatching or shading does not convey or indicate any preference or need for the specific materials, material properties, dimensions, proportions, commonalities between the elements shown, and / or any other characteristics, attributes, properties, etc. of the elements. In addition, in the drawings, the sizes and relative sizes of the elements may be exaggerated for clarity and / or descriptive purposes. When the exemplary embodiments can be implemented differently, a specific process sequence can be performed in a different order than described. For example, two continuously described processes can be performed substantially simultaneously or in an order opposite to the described order. In addition, the same reference numerals represent the same elements.
[0048] When an element or layer is referred to as being "on" another element or layer, "connected to" or "bound to" another element or layer, the element or layer may be directly on, directly connected to or directly bound to the other element or layer, or there may be intermediate elements or intermediate layers. However, when an element or layer is referred to as being "directly on" another element or layer, "directly connected to" or "directly bound to" another element or layer, there are no intermediate elements or intermediate layers. For this purpose, the term "connected" may refer to a physical connection, an electrical connection and / or a fluid connection with or without intermediate elements. In addition, the D1 axis, the D2 axis and the D3 axis are not limited to the three axes of a rectangular coordinate system (such as the x-axis, the y-axis and the z-axis) and may be interpreted in a broader sense. For example, the D1 axis, the D2 axis and the D3 axis may be perpendicular to each other, or may represent different directions that are not perpendicular to each other. For the purposes of this disclosure, “at least one of X, Y, and Z” and “at least one selected from the group consisting of X, Y, and Z” may be interpreted as only X, only Y, only Z, or any combination of two or more of X, Y, and Z, such as XYZ, XYY, YZ, and ZZ for example. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items.
[0049] Although the terms "first," "second," etc. may be used herein to describe various types of elements, these elements should not be limited by these terms. These terms are used to distinguish one element from another. Thus, a first element discussed below could be named a second element without departing from the teachings of the disclosure.
[0050] For descriptive purposes, spatially relative terms such as "under," "beneath," "beneath," "down," "over," "up," "above," "higher," "side" (e.g., as in "sidewall"), etc., may be used herein to describe the relationship of one element to another (other) element as shown in the accompanying drawings. Spatially relative terms are intended to encompass different orientations of the device in use, operation, and / or manufacture in addition to the orientation depicted in the accompanying drawings. For example, if the device in the drawings is turned over, an element described as "under" or "beneath" other elements or features would then be positioned "over" the other elements or features. Thus, the exemplary term "under" can include both above and below orientations. Furthermore, the device can be positioned otherwise (e.g., rotated 90 degrees or at other orientations), with the spatially relative descriptors used herein interpreted accordingly.
[0051] The terms used herein are for the purpose of describing specific embodiments and are not intended to be limiting. As used herein, unless the context clearly indicates otherwise, the singular "one", "one (kind / person)" and "said (the)" are also intended to include plural forms. In addition, when using the terms "comprise" and / or "include" and their variations in this manual, it is explained that there are stated features, integral bodies, steps, operations, elements, components and / or their groups, but it is not excluded that there are or add one or more other features, integral bodies, steps, operations, elements, components and / or their groups. It is also noted that, as used herein, the terms "substantially (substantially)", "about (approximately)" and other similar terms are used as approximate terms and not as degree terms, and are so used to explain the inherent deviation of measured values, calculated values and / or provided values that those of ordinary skill in the art will recognize.
[0052] Various exemplary embodiments are described herein with reference to cross-sectional views and / or exploded views that are schematic diagrams of idealized exemplary embodiments and / or intermediate structures. As such, variations in the shapes of the illustrations due to, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the exemplary embodiments disclosed herein should not be construed as being limited to the specific illustrated shapes of the regions, but rather are to include deviations in shapes due to, for example, manufacturing. In this manner, the regions illustrated in the accompanying drawings may be schematic in nature, and the shapes of these regions may not reflect the actual shapes of the regions of the device, and as such, are not necessarily intended to be limiting.
[0053] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure is a part. Terms (such as those defined in common dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and should not be interpreted in an idealized or overly formal sense unless clearly defined herein.
[0054] The applicant has found that the emission layer included in the related art organic light emitting device has high resistance compared to other layers included in the organic light emitting device, so that the characteristics of the organic light emitting device can be considered to be largely determined by the characteristics of the emission layer.
[0055] Considering the problem of controlling holes and electrons at an appropriate ratio in an emission layer and performing stable driving, it is difficult for a related art organic light emitting device including a single host or two hosts to simultaneously improve efficiency and lifespan.
[0056] According to one aspect of some exemplary embodiments of the invention, a light-emitting device includes a first electrode, a second electrode facing the first electrode, and an intermediate layer located between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer includes: i) a hole transport region arranged between the first electrode and the emission layer; and ii) an electron transport region arranged between the emission layer and the second electrode, the emission layer includes three or more hosts, the electron transport region includes a buffer layer, the three or more hosts include a hole transport host (HT), a first electron transport host (ET1) and a second electron transport host (ET2), the buffer layer includes a third electron transport host (ET2'), and the lowest unoccupied molecular orbital (LUMO) energy level of ET2 is equal to the LUMO energy level of ET2'.
[0057] Applicants have discovered that in prior art devices, a potential barrier exists between the host and the buffer layer, increasing the driving voltage and hindering smooth electron transport. In light-emitting devices constructed according to the principles of the present invention and certain exemplary embodiments, by making the LUMO energy level of ET2 equal to the LUMO energy level of ET2', the potential barrier between the host and the buffer layer is removed, thereby inducing smooth electron transport from the buffer layer to the emissive layer, thereby improving the performance of the light-emitting device.
[0058] In one exemplary embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof. In one exemplary embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0059] In an exemplary embodiment, the highest occupied molecular orbital (HOMO) energy level of ET2 may be equal to the HOMO energy level of ET2'. In an exemplary embodiment, the LUMO energy levels of HT, ET1, and ET2 may satisfy the following inequality (1) and inequality (2):
[0060] |E LUMO_HT |>|E LUMO_ET1 | (1)
[0061] |E LUMO_HT |>|E LUMO_ET2 | (2).
[0062] In an exemplary embodiment, the HOMO energy levels of HT, ET1, and ET2 may satisfy the following inequality (3):
[0063] |E HOMO_ET2 |>|E HOMO_ET1 |>|E HOMO_HT| (3).
[0064] In an exemplary embodiment, the LUMO energy level and the HOMO energy level of ET1 and ET2 may satisfy the following inequality (4) and inequality (5):
[0065] |E LUMO_ET2 |>|E LUMO_ET1 | (4)
[0066] |E HOMO_ET2 |>|E HOMO_ET1 | (5).
[0067] In an exemplary embodiment, the LUMO energy level and the HOMO energy level of ET1 and ET2 may satisfy the following inequality (6) and inequality (7):
[0068] |E LUMO_ET2 -E LUMO_ET1 |≤0.1eV (6)
[0069] |E HOMO_ET2 -E HOMO_ET1 |≤0.1eV (7).
[0070] In one exemplary embodiment, ET2 and ET2' may be the same compound as each other.
[0071] In one exemplary embodiment, a buffer layer included in the light emitting device may contact the emission layer. In one exemplary embodiment, the electron transport region of the light emitting device may include an electron transport layer, and the buffer layer of the light emitting device may contact the electron transport layer.
[0072] In one exemplary embodiment, the hole transport region of the light-emitting device may include an emission-assisting layer, and the emission-assisting layer may include a charge-generating material. In one exemplary embodiment, the emission-assisting layer may have a two-layer structure. For example, the emission-assisting layer may include a layer including a charge-generating material and a layer not including a charge-generating material. The layer not including a charge-generating material refers to a layer consisting only of a compound that may be included in the hole transport region, wherein such a compound will be described below.
[0073] In an exemplary embodiment, the hole transport region of the light-emitting device may include an emission-assisting layer and a hole transport layer, and the emission-assisting layer may be in contact with the hole transport layer. The emission-assisting layer may be the same as described above. For example, the emission-assisting layer may have a two-layer structure and be composed of a layer including a charge-generating material and a layer not including a charge-generating material. In an exemplary embodiment, the layer not including a charge-generating material in the emission-assisting layer may be in contact with the emission layer. In an exemplary embodiment, the layer including a charge-generating material in the emission-assisting layer may be in contact with the hole transport layer. In an exemplary embodiment, the hole transport layer may include a charge-generating material. For example, the hole transport layer may have a two-layer structure and be composed of a layer including a charge-generating material and a layer not including a charge-generating material.
[0074] In an exemplary embodiment, the layer that does not include a charge generating material in the hole transport layer may be in contact with the layer that includes a charge generating material in the emission-assisting layer. In an exemplary embodiment, the layer that includes a charge generating material in the hole transport layer may be in contact with the first electrode. In an exemplary embodiment, the charge generating material may be a p-dopant. The p-dopant will be described below. In an exemplary embodiment, the emission layer may be a green emission layer. In an exemplary embodiment, the light-emitting device may be a phosphorescent device. In an exemplary embodiment, the emission layer may include three types of hosts.
[0075] According to another aspect of some exemplary embodiments of the invention, an electronic device includes a thin film transistor and a light emitting device, wherein the thin film transistor includes a source electrode, a drain electrode, an active layer and a gate electrode, and a first electrode of the light emitting device is electrically connected to one of the source electrode and the drain electrode of the thin film transistor.
[0076] Figure 1 Description
[0077] Figure 1 is a schematic cross-sectional view of an exemplary embodiment of a light emitting device constructed according to the principles of the invention. The light emitting device 10 includes a first electrode 110, an intermediate layer 150, and a second electrode 190.
[0078] In the following, we will combine Figure 1 The structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to the embodiment are described.
[0079] First electrode 110
[0080] exist Figure 1In the embodiment of the present invention, a substrate may be further provided below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate. The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a high work function material that easily injects holes may be used as the material for forming the first electrode 110.
[0081] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but exemplary embodiments are not limited thereto. In one or more exemplary embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but exemplary embodiments are not limited thereto.
[0082] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.
[0083] Middle layer 150
[0084] The intermediate layer 150 is disposed on the first electrode 110. The intermediate layer 150 includes an emission layer. The intermediate layer 150 may further include a hole transport region disposed between the first electrode 110 and the emission layer and an electron transport region disposed between the emission layer and the second electrode 190.
[0085] In addition to various organic materials, the intermediate layer 150 may further include a metal-containing compound such as an organometallic compound, an inorganic material such as a quantum dot, and the like.
[0086] Hole transport region in the intermediate layer 150
[0087] The hole transport region may have: i) a single-layer structure consisting of a single layer composed of a single material; ii) a single-layer structure consisting of a single layer composed of a plurality of different materials; or iii) a multi-layer structure including a plurality of layers containing different materials.
[0088] The hole transport region may include a hole injection layer, a hole transport layer, an emission-assisting layer, an electron blocking layer, or any combination thereof. As described above, the hole transport layer may include a charge generating material. For example, the hole transport layer may have a two-layer structure and be composed of a layer including a charge generating material and a layer not including a charge generating material.
[0089] For example, the hole transport region may have a multilayer structure, comprising a layer containing a charge generating material / hole transport layer structure, a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the first electrode 110 in the order stated, but exemplary embodiments are not limited thereto.
[0090] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0091] Formula 201
[0092]
[0093] Formula 202
[0094]
[0095] In Equations 201 and 202,
[0096] L 201 To L 204 may be independently 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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0097] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 Alkenylene, substituted or unsubstituted C3-C 10Cycloalkylene, 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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0098] xa1 to xa4 may each independently be 0, 1, 2 or 3 (e.g., 0, 1 or 2),
[0099] xa5 can be an integer from 1 to 10 (e.g., 1, 2, 3, or 4), and
[0100] R 201 to R 204 and Q 201 may be independently 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 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0101] For example, in Equation 202, R 201 and R 202 may optionally be linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R 203 and R 204 They may optionally be linked to one another via single bonds, dimethyl-methylene or diphenyl-methylene groups.
[0102] In one exemplary embodiment, i) R in Formula 201 201 to R 203 At least one of ii) R in Formula 202 201 to R 204 At least one of them may be independently unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted C1-C 10 Alkyl phenyl, phenyl substituted with -F, naphthyl, phenanthryl, indenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzofluorenyl, dimethylbenzofluorenyl, diphenylbenzofluorenyl, indenophenanthryl, dimethylindenophenanthryl, diphenylindenophenanthryl, pyridyl, pyrrolyl, thienyl, furyl, indolyl, phenylindolyl, benzindolyl, phenylbenzindolyl, isoindolyl, phenylisoindolyl, benzisoindolyl, phenylbenzisodolyl, benzothiols, dimethylbenzothiols, diphenylbenzothiols, benzothiols The present invention also includes a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenophenanthryl group, a pyridyl group, a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, an isoindolyl group, a benzisoindolyl group, a benzothiorol group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorol group, a dimethyldibenzothiorol group, a diphenyldibenzothiorol group, a dibenzothiophenyl group, and a dibenzofuranyl group, but exemplary embodiments are not limited thereto.
[0103] In one or more exemplary embodiments, the compound represented by Formula 201 or Formula 202 may include at least one carbazole group. In one or more exemplary embodiments, the compound represented by Formula 201 may not include a carbazole group.
[0104] The hole transport region may include compounds such as m-4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (MTDATA), 1-N,1-N-bis[4-(diphenylamino)phenyl]-4-N,4-N-diphenylbenzene-1,4-diamine (TDATA), 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenyl-(1, 1'-biphenyl)-4,4'-diamine (NPB or NPD), N4,N4'-di(naphthalene-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (β-NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine (TPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-9,9-spirobifluorene-2,7-diamine (spiro-TPD), N2,N7-di- 1-naphthyl-N2,N7-diphenyl-9,9'-spirobi[9H-fluorene]-2,7-diamine (spiro-NPB), N,N'-di(1-naphthyl)-N,N'-2,2'-dimethyldiphenyl-(1,1'-biphenyl)-4,4'-diamine (methylated-NPB), 4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC), N,N,N',N'-tetrakis(3-methylphenyl)-3,3'-dimethyl Benzidine (HMTPD), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or a combination thereof. However, exemplary embodiments are not limited thereto:
[0105]
[0106] The thickness of the hole transport region can be about to about within the range of, for example, about to about When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to about within the range of, for example, about to about and the thickness of the hole transport layer can be in the range of about to about within the range of, for example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0107] The emission-assisting layer can improve the luminous efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission-assisting layer and the electron blocking layer can include the materials described above. The emission-assisting layer can be the same as described above. The electron blocking layer can serve as a layer to prevent electron injection from the electron transport region. The electron blocking layer can include the materials described above.
[0108] p-dopant
[0109] In addition to the above-mentioned materials, the hole transport region may include a charge generating material for improving the conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region. The charge generating material may be, for example, a p-dopant. In one exemplary embodiment, the LUMO energy level of the p-dopant may be approximately -3.5 eV or less. The p-dopant may include a quinone derivative, a metal oxide, a cyano compound, or any combination thereof, but exemplary embodiments are not limited thereto.
[0110] In one exemplary embodiment, the p-dopant may include at least one selected from the following compounds: a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), etc.; a metal oxide, such as tungsten oxide or molybdenum oxide; a cyano-containing compound, such as 1,4,5,8,9,12-hexaazatriphenylene-hexanitrile (HAT-CN), etc.; a compound represented by Formula 221; or any combination thereof.
[0111] However, exemplary embodiments are not limited thereto:
[0112]
[0113] Formula 221
[0114]
[0115] In formula 221,
[0116] R 221 to R 223 may be independently 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 10Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group or substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein R 221 to R 223 At least one of them can be independently unsubstituted or substituted with a substituent C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group, wherein the substituent is cyano, -F, -Cl, -Br, -I, C1-C1 substituted with at least one cyano group 20 Alkyl, C1-C substituted with at least one -F 20 Alkyl, C1-C substituted with at least one -Cl 20 Alkyl, C1-C substituted with at least one -Br 20 Alkyl, C1-C substituted with at least one -I 20 For example, the p-dopant may be included in the hole transport layer and / or the emission assist layer.
[0117] Emission layer in the middle layer 150
[0118] When the light-emitting device 10 is a full-color light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to the sub-pixel. In one exemplary embodiment, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In one or more exemplary embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0119] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof. The amount of the dopant in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host. However, exemplary embodiments are not limited thereto.
[0120] In one or more exemplary embodiments, the emission layer may include quantum dots. The thickness of the emission layer may be about to about within the range of, for example, about to about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0121] Subjects in the emission layer
[0122] In one exemplary embodiment, the emission layer included in the light emitting device 10 according to the exemplary embodiment may include three or more hosts, which may include HT, ET1 and ET2, wherein the LUMO energy level of ET2 may be equal to the LUMO energy level of ET2' of the buffer layer.
[0123] In one or more exemplary embodiments, the emission layer included in the light-emitting device 10 may include three or more hosts, and the three or more hosts may include HT, ET1 and ET2, wherein the LUMO energy level of ET2 may be equal to the LUMO energy level of ET2' of the buffer layer to be described below, and the HOMO energy level of ET2 may be equal to the HOMO energy level of ET2'.
[0124] To serve as a host, a compound satisfying the aforementioned energy level relationship can be used among HT, ET1, and ET2 included in the emissive layer, and ET2' included in the buffer layer. For example, HT can be a fluorene compound, a carbazole compound, a diarylamine compound, a triarylamine compound, a dibenzofuran compound, a dibenzothiophene compound, or a dibenzosilole compound. For example, ET1, ET2, and ET2' can each independently be a triazine compound, a triazole compound, an imidazole compound, or an oxazine compound.
[0125] For example, the host may include a compound represented by Formula 301:
[0126] Formula 301
[0127] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0128] In formula 301,
[0129] Ar 301 It can be substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group,
[0130] xb11 can be 1, 2 or 3,
[0131] L 301 It can be 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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0132] xb1 can be 0, 1, 2, 3, 4 or 5,
[0133] R 301 It can be deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 ) or -P(=O)(Q 301 )(Q 302 ),
[0134] xb21 can be 1, 2, 3, 4, or 5, and
[0135] Q 301 To Q 303 Can be combined with Q as described here 11 Same as described.
[0136] In one or more exemplary embodiments, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 In one exemplary embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0137] Formula 301-1
[0138]
[0139] Formula 301-2
[0140]
[0141] In Formula 301-1 and Formula 301-2,
[0142] Ring A 301 To Ring A 304 Can be independently C5-C 60 Carbocyclic or C1-C 60 heterocyclic group,
[0143] X 301 Can be O, S, N-[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0144] xb22 and xb23 can each independently be 0, 1 or 2,
[0145] L 301 , xb1 and R 301 Can be the same as above,
[0146] L 302 To L 304 Can be independently combined with L 301 Same as described,
[0147] xb2 to xb4 may each independently be the same as described in conjunction with xb1, and
[0148] R 302 to R 305 and R 311 to R314 Can be combined with R 301 Same as described.
[0149] In one or more exemplary embodiments, the host may include an alkaline earth metal complex. For example, the host may be a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0150] In one exemplary embodiment, the host may include one of Compounds H1 to H120 or 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), or any combination thereof, but exemplary embodiments are not limited thereto.
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158] Phosphorescent dopants in the emission layer included in the intermediate layer 150
[0159] The phosphorescent dopant may include at least one transition metal as a central metal. The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a quadridentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof. The phosphorescent dopant may be electrically neutral.
[0160] For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0161] Formula 401
[0162] M(L 401 ) xc1 (L 402 ) xc2
[0163] Formula 402
[0164]
[0165] In Equations 401 and 402,
[0166] M can be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0167] L 401 The ligand may be a ligand represented by formula 402, and xc1 may be 1, 2 or 3. When xc1 is 2 or greater, two or more L 401 can be the same as or different from each other,
[0168] L 402 can be an organic ligand, xc2 can be 0, 1, 2, 3 or 4, and when xc2 is 2 or greater, two or more L 402 can be the same as or different from each other,
[0169] X 401 and X 402 may each independently be nitrogen or carbon,
[0170] Ring A 401 and Ring A 402 Can be independently C5-C 60 Carbocyclic or C1-C 60 heterocyclic group,
[0171] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*' or *=C=*',
[0172] X 403 and X 404 can be independently a chemical bond (eg, a covalent bond or a coordinate bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),and
[0173] Q411 To Q 414 can be combined with Q as described here 11 Same as described.
[0174] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 ) or -P(=O)(Q 401 )(Q 402 ),
[0175] Q 401 To Q 403 can be combined with Q as described here 11 Same as described,
[0176] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0177] * and *' in Formula 402 both represent the binding sites with M in Formula 401.
[0178] In one or more exemplary embodiments, in equation 402, i) X 401 Can be nitrogen, X 402 Can be carbon, or ii) X 401 and X 402 Each of can be nitrogen.
[0179] In one or more exemplary embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two rings A 401 It can optionally be connected via T as a linker 402 connected to each other, or two or more L 401 The two rings A 402 It can optionally be connected via T as a linker 403 Connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 can be combined with T as described here 401 Same as described.
[0180] L in Formula 401 402 It can be an organic ligand. For example, L 402 It may be a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group or a phosphite group), or any combination thereof, but exemplary embodiments are not limited thereto.
[0181] The phosphorescent dopant may include, for example, one or any combination of the following compounds PD1 to PD25, but exemplary embodiments are not limited thereto:
[0182]
[0183]
[0184] Fluorescent dopants in the emission layer
[0185] The fluorescent dopant may include an arylamine compound or a styrylamine compound. For example, the fluorescent dopant may include a compound represented by Formula 501:
[0186] Formula 501
[0187]
[0188] In formula 501,
[0189] Ar 501 It can be substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group,
[0190] L 501 To L 503may be independently 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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0191] xd1 to xd3 can each independently be 0, 1, 2 or 3,
[0192] R 501 and R 502 may be independently 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 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
[0193] xd4 can be 1, 2, 3, 4, 5 or 6.
[0194] For example, Ar in Formula 501 501 It may be a condensed ring in which three or more monocyclic groups are condensed with each other (e.g., anthracene, In one exemplary embodiment, xd4 in Formula 501 may be 2, but exemplary embodiments are not limited thereto.
[0195] For example, the fluorescent dopant may include one of the following compounds FD1 to FD36 or 4,4′-bis(2,2-diphenylvinyl)-1,1′-biphenyl (DPVBi), 4,4′-bis[4-(di-p-tolylamino)phenylvinyl]biphenyl (DPAVBi), or any combination thereof:
[0196]
[0197]
[0198]
[0199]
[0200] Electron transport region in the intermediate layer 150
[0201] The electron transport region may have: i) a single-layer structure consisting of a single layer composed of a single material; ii) a single-layer structure consisting of a single layer composed of a plurality of different materials; or iii) a multi-layer structure including a plurality of layers containing different materials.
[0202] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof, but exemplary embodiments are not limited thereto. For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein for each structure, the constituent layers are stacked sequentially from the emission layer in the order stated. However, exemplary embodiments of the structure of the electron transport region are not limited thereto.
[0203] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π-electron deficient nitrogen-containing cyclic group (or a π-electron-depleted nitrogen-containing cyclic group) that can readily accept electrons.
[0204] Examples of π-electron-poor nitrogen-containing ring groups are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, azacarbazolyl, azafluorenyl, azadibenzothiopheneyl, azadibenzofuran ... Examples of the present invention include thiazolyl, oxazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, and imidazopyridazinyl, but exemplary embodiments are not limited thereto.
[0205] The buffer layer may include ET2'. To function as ET2', a compound satisfying the above-described energy level relationship among HT, ET1, and ET2 included in the emission layer and ET2' included in the buffer layer may be used in the buffer layer.
[0206] For example, the electron transport region may include a compound represented by Formula 601 and including at least one π-electron-poor nitrogen-containing ring group:
[0207] Formula 601
[0208] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0209] In Equation 601,
[0210] Ar 601 It can be substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 heterocyclic group,
[0211] xe11 can be 1, 2 or 3,
[0212] L 601 It can be 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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0213] xe1 can be 0, 1, 2, 3, 4 or 5,
[0214] R 601 It can be 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 60Arylthio, 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 ) or -P(=O)(Q 601 )(Q 602 ),
[0215] Q 601 To Q 603 can be combined with Q as described here 11 Same as described, and
[0216] xe21 can be 1, 2, 3, 4 or 5.
[0217] For example, Ar in Formula 601 601 , L 601 and R 601 At least one of the may independently include at least one π-electron-poor nitrogen-containing ring group. In one or more exemplary embodiments, when xe11 in Formula 601 is 2 or greater, two or more Ar 601 Can be connected to each other via a single bond. In one exemplary embodiment, Ar in Formula 601 601 The anthracenyl group may be substituted or unsubstituted.
[0218] In one exemplary embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0219] Formula 601-1
[0220]
[0221] In formula 601-1,
[0222] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R 616 ), and X 614 To X 616 At least one of can be N,
[0223] L 611 To L 613 Can be independently combined with L 601 Same as described,
[0224] xe611 to xe613 can each independently be the same as described in conjunction with xe1,
[0225] R 611 to R 613 Can independently bind to R 601 Same as described, and
[0226] R 614 to R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl.
[0227] For example, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can each independently be 0, 1, or 2.
[0228] The electron transport region may include one of the following compounds ET1 to ET36 or 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinolinolato)aluminum (Alq3), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or any combination thereof, but exemplary embodiments are not limited thereto:
[0229]
[0230]
[0231]
[0232] The thickness of the buffer layer, hole blocking layer and electron control layer can each be independently about to about within the range of, for example, about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within the above ranges, excellent hole blocking characteristics or excellent electron control characteristics can be obtained without significantly increasing the driving voltage.
[0233] The thickness of the electron transport layer can be about to about within the range of, for example, about to about When the thickness of the electron transport layer is within the above range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage. In addition to the above materials, the electron transport region (for example, the electron transport layer in the electron transport region) may further include a metal-containing material.
[0234] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof, but exemplary embodiments are not limited thereto.
[0235] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate (LiQ)) or compound ET-D2:
[0236]
[0237] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0238] The electron injection layer may have: i) a single-layer structure consisting of a single layer composed of a single material; ii) a single-layer structure consisting of a single layer composed of a plurality of different materials; or iii) a multi-layer structure including a plurality of layers containing different materials.
[0239] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0240] Alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0241] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound can be oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals, or any combination thereof.
[0242] The alkali metal compound can be an alkali metal oxide (such as Li2O, Cs2O, or K2O), an alkali metal halide (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI), or any combination thereof. The alkaline earth metal compound can include an alkaline earth metal oxide (such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) or Ba x Ca 1-x O(0 < x < 1)). The rare earth metal compound can include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof.
[0243] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex can include: i) one of the metal ions of alkali metals, alkaline earth metals, and rare earth metals; and ii) ligands (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof) attached to the metal ion, but the exemplary embodiments are not limited thereto.
[0244] The electron injection layer is composed of (or includes) an alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof, or may further include an organic material (e.g., a compound represented by Formula 601). When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof can be uniformly or non-uniformly dispersed in the matrix including the organic material.
[0245] The thickness of the electron injection layer can be in the range of about to about For example, in the range of about to about 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 the driving voltage.
[0246] Second electrode 190
[0247] The second electrode 190 may be located on the intermediate layer 150 having such a structure. The second electrode 190 may be a cathode as an electron injection electrode, and a metal, an alloy, a conductive compound, or any combination thereof, each having a low work function, may be used as a material for the second electrode 190.
[0248] The second electrode 190 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ITO, IZO, or any combination thereof, but exemplary embodiments are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0249] cap layer
[0250] The first capping layer may be located outside the first electrode 110, and / or the second capping layer may be located outside the second electrode 190. In detail, the light emitting device 10 may have: a structure in which the first capping layer, the first electrode 110, the intermediate layer 150, and the second electrode 190 are sequentially stacked in the stated order; a structure in which the first electrode 110, the intermediate layer 150, the second electrode 190, and the second capping layer are sequentially stacked in the stated order; or a structure in which the first capping layer, the first electrode 110, the intermediate layer 150, the second electrode 190, and the second capping layer are sequentially stacked in the stated order.
[0251] The light generated by the emission layer of the intermediate layer 150 of the light-emitting device 10 can be extracted toward the outside through the first electrode 110 and the first cover layer (each first electrode 110 can be a semi-transmissive electrode or a transmissive electrode), or the light generated by the emission layer of the intermediate layer 150 of the light-emitting device 10 can be extracted toward the outside through the second electrode 190 and the second cover layer (each second electrode 190 can be a semi-transmissive electrode or a transmissive electrode).
[0252] The first cap layer and the second cap layer can improve external luminous efficiency according to the principle of constructive interference.The first cap layer and the second cap layer can each independently be an organic cap layer comprising an organic material, an inorganic cap layer comprising an inorganic material, or a composite cap layer comprising an organic material and an inorganic material.
[0253] At least one of the first cap layer and the second cap layer may independently include a carbocyclic compound, a heterocyclic compound, an amine (or amino) compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may be optionally substituted with a substituent comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In some exemplary embodiments, at least one of the first cap layer and the second cap layer may independently include an amine-containing compound.
[0254] For example, at least one of the first capping layer and the second capping layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
[0255] In one or more exemplary embodiments, at least one of the first cap layer and the second cap layer may each independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, or any combination thereof, but exemplary embodiments are not limited thereto:
[0256]
[0257] equipment
[0258] The light emitting device may be included in various devices. For example, a lighting device, an authentication device, or an electronic device including the light emitting device may be provided.
[0259] In addition to the light-emitting device described above, the light-emitting device may further include a color filter. The color filter may be provided in at least one direction of travel of the light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light, but exemplary embodiments are not limited thereto. The light-emitting device may be the same as described above. The light-emitting device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, and the color filter may include a plurality of color filter regions corresponding to the plurality of sub-pixel regions, respectively. A pixel-defining film may be located between the plurality of sub-pixel regions to define each sub-pixel region.
[0260] The color filter may further include a light-blocking pattern located between the plurality of color filter regions. The plurality of color filter regions may include a first color filter region emitting a first color light, a second color filter region emitting a second color light, and / or a third color filter region emitting a third color light, and the first color light, the second color light, and the third color light may have different maximum emission wavelengths from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light, but exemplary embodiments are not limited thereto. For example, the plurality of color filter regions may each include quantum dots, but exemplary embodiments are not limited thereto. In detail, the first color filter region may include red quantum dots, the second color filter region may include green quantum dots, and the third color filter region may not include quantum dots. Quantum dots can be understood by referring to the description thereof provided herein. The first color filter region, the second color filter region, and / or the third color filter region may each include a scatterer, but exemplary embodiments are not limited thereto.
[0261] For example, the light emitting device may emit a first light, the first color filter region may absorb the first light to emit a first first color light, the second color filter region may absorb the first light to emit a second first color light, and the third color filter region may absorb the first light to emit a third first color light. In this regard, the first first color light, the second first color light, and the third first color light may have different maximum emission wavelengths. Specifically, the first light may be blue light, the first first color light may be red light, the second first color light may be green light, and the third first color light may be blue light, but exemplary embodiments are not limited thereto.
[0262] In addition to the light emitting device described above, the light emitting device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light emitting device.
[0263] The thin film transistor may further include a gate electrode, a gate insulating layer, etc. The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc., but exemplary embodiments are not limited thereto.
[0264] The light-emitting device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside while concurrently preventing external air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including multiple organic layers and / or multiple inorganic layers. When the sealing portion is a thin-film encapsulation layer, the light-emitting device may be flexible.
[0265] The light emitting device may be used as various displays, light sources, etc. The authentication device may be, for example, a biometric authentication device for authenticating an individual by utilizing biometric information of a biometric body (eg, fingertip, pupil, etc.).
[0266] In addition to the light-emitting device, the authentication device may also include a biometric information collector. The electronic device may be applied to a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic notepad, an electronic dictionary, an electronic game console, a medical instrument (e.g., an electronic thermometer, a blood pressure meter, a blood glucose 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, meters (e.g., meters for vehicles, aircraft, and ships), a projector, etc., but exemplary embodiments are not limited thereto.
[0267] Preparation method
[0268] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be formed in a specific region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.
[0269] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature can be set at about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and about to about Vacuum deposition was performed at a deposition rate of 100 Å.
[0270] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80°C to about 200°C, taking into account the materials to be included in the layer to be formed and the structure of the layer to be formed.
[0271] General definitions including substituents
[0272] As used herein, the term "intermediate layer" refers to a single layer and / or all layers located between the first electrode and the second electrode of the light emitting device. The material included in the "intermediate layer" may include an organic material, an inorganic material, or any combination thereof.
[0273] The "π-electron-poor nitrogen-containing ring group" may be a C1-C1-C2-N1-N2 ...60 Heterocyclic group. For example, the "π-electron-poor nitrogen-containing cyclic group" can be: i) a first ring; ii) a condensed cyclic group in which two or more first rings are fused to each other; or iii) a condensed cyclic group in which at least one first ring and at least one second ring are fused, wherein the first ring is a heteromonocyclic group including at least one *-N=*' moiety as a ring component (e.g., imidazolyl, pyridyl, triazinyl, etc.), and the second ring is a cyclic group not including a *-N=*' moiety as a ring component (e.g., phenyl, dibenzofuranyl, carbazolyl, etc.).
[0274] As used herein, the term "C1-C 60 The term “alkyl” refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, exemplified by methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl. As used herein, the term “C1-C 60 "Alkylene" refers to a group having a C1-C 60 Alkyl corresponds to a divalent group of the structure.
[0275] As used herein, the term "C2-C 60 "Alkenyl" refers to a C2-C 60 A monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the alkyl group, examples of which include ethenyl, propenyl, and butenyl. As used herein, the term "C2-C 60 "Alkenylene" refers to a group having a C2-C 60 Alkenyl corresponds to a divalent group of the structure.
[0276] As used herein, the term "C2-C 60 "Alkynyl" refers to a C2-C 60 A monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of the alkyl group, examples of which include ethynyl and propynyl. As used herein, the term "C2-C 60 "Alkyne" refers to a group having a C2-C 60 Alkynyl corresponds to a divalent group of the structure.
[0277] As used herein, the term "C1-C 60 "Alkoxy" refers to 101 (Among them, A 101 C1-C 60 The monovalent group represented by an alkyl group is exemplified by a methoxy group, an ethoxy group, and an isopropoxy group.
[0278] As used herein, the term "C3-C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring radical having 3 to 10 carbon atoms, exemplified by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, and bicyclo[2.2.2]octyl. As used herein, the term "C3-C 10 "Cycloalkylene" refers to a group having a C3-C 10 The cycloalkyl group corresponds to a divalent group of the structure.
[0279] As used herein, the term "C1-C 10 "Heterocycloalkyl" refers to a monovalent saturated cyclic group having 1 to 10 carbon atoms containing a heteroatom (e.g., N, O, Si, P, S, or any combination thereof) as a ring atom, and examples thereof are 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, and tetrahydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkylene" refers to a group having a C1-C 10 The heterocycloalkyl group corresponds to a divalent group of the structure.
[0280] As used herein, the term "C3-C 10 "Cycloalkenyl" refers to a monovalent hydrocarbon ring group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, non-limiting examples of which include cyclopentenyl, cyclohexenyl and cycloheptenyl. As used herein, the term "C3-C 10 "Cycloalkenylene" refers to a group having a C3-C 10 The cycloalkenyl group corresponds to a divalent group of the structure.
[0281] As used herein, the term "C1-C 10 "Heterocycloalkenyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms containing a heteroatom (e.g., N, O, Si, P, S, or any combination thereof) as a ring atom, wherein the ring has at least one double bond. 10 Examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkenylene" refers to a group having a C1-C 10 The heterocycloalkenyl group corresponds to a divalent group of the structure.
[0282] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system comprising 6 to 60 carbon atoms, and the term "C6-C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms.60 Examples of aryl groups are phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubenyl, coryl and oxadiphenyl. 60 Aryl and C6-C 60 When the arylene groups each include two or more rings, the two or more rings may be fused to each other.
[0283] As used herein, the term "C1-C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having a heteroatom (e.g., N, O, Si, P, S, or any combination thereof) as a ring atom and 1 to 60 carbon atoms, such as the term "C1-C 60 "Heteroarylene" refers to a divalent group having a heterocyclic aromatic system having a heteroatom (e.g., N, O, Si, P, S, or any combination thereof) as a ring atom and 1 to 60 carbon atoms. 60 Examples of heteroaryl groups are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl and naphthyridinyl. 60 Heteroaryl and C1-C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other.
[0284] As used herein, the term "C6-C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 C6-C 60 Aryl), as used herein, the term "C6-C 60 "Arylthio" refers to -SA 103 (Among them, A 103 C6-C 60 aryl).
[0285] As used herein, the term "monovalent non-aromatic condensed polycyclic radical" refers to a monovalent group having two or more rings fused to each other, only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms and not having aromaticity in its entire molecular structure. Examples of monovalent non-aromatic condensed polycyclic radicals include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, and indenoanthryl. As used herein, the term "divalent non-aromatic condensed polycyclic radical" refers to a divalent group having a structure corresponding to a monovalent non-aromatic condensed or condensed polycyclic radical.
[0286] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein refers to a monovalent group in which two or more rings are fused to each other, includes heteroatoms (e.g., N, O, Si, P, and S, or any combination thereof) other than carbon (e.g., having 1 to 60 carbon atoms) as ring-constituting atoms, and does not have aromaticity in its overall molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group are pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having a structure corresponding to a monovalent non-aromatic condensed heteropolycyclic group.
[0287] As used herein, the term "C5-C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group that includes only carbon as a ring atom and consists of 5 to 60 carbon atoms. 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 60 The carbocyclic group can be a compound (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). In one or more exemplary embodiments, the carbonyl group is connected to a C5-C 60 The number of substituents of the carbocyclic group, C5-C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0288] C5-C 60 Examples of carbocyclic groups are cyclopentadienyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzophenanthrenyl ...
[0289] As used herein, the term "C1-C 60 The term "heterocyclic group" refers to a monocyclic or polycyclic group including 1 to 60 carbon atoms and heteroatoms (e.g., N, O, Si, P, S, or any combination thereof) other than carbon (the carbon number can be 1 to 60) as ring atoms. 60 The heterocyclic group may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. 60 The heterocyclic group can be a compound (such as pyridine), a monovalent group (such as pyridyl) or a divalent group (such as pyridylene). In one or more exemplary embodiments, the heterocyclic group is connected to C1-C 60 The number of substituents of the heterocyclic group, C1-C 60 The heterocyclic group may be a trivalent group or a tetravalent group.
[0290] C1-C 60 Examples of heterocyclic groups are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl , triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzothiorrolocarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzonaphthothiophenyl, benzofurandibenzofuranyl, benzofurandibenzothiophenyl and benzothienodibenzothiophenyl.
[0291] Substituted C5-C 60 Carbocyclic, substituted C1-C 60 Heterocyclic, substituted C1-C 60 Alkylene, substituted C2-C 60 Alkenylene, substituted C3-C10 Cycloalkylene, substituted C1-C 10 Heterocycloalkylene, substituted C3-C 10 Cycloalkenylene, substituted C1-C 10 Heterocycloalkenylene, substituted C6-C 60 Arylene, substituted C1-C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 The substituents in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
[0292] Deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;
[0293] are unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic 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 )(Q12 ) of at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 alkoxy;
[0294] are unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) of at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group;
[0295] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ); or any combination thereof.
[0296] As used herein, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, or a terphenyl group.
[0297] As used herein, the term "Ph" refers to a phenyl group, as used herein, the term "Me" refers to a methyl group, as used herein, the term "Et" refers to an ethyl group, as used herein, the term "tert-Bu" or "Bu" refers to an ethyl group. t ” refers to tert-butyl, and the term “OMe” as used herein refers to methoxy.
[0298] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". In other words, a "biphenyl group" is a group having C6-C 60 A phenyl group substituted with an aryl group as a substituent.
[0299] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". In other words, a "terphenyl group" is a group having a C6-C 60 C6-C 60 A phenyl group substituted with an aryl group as a substituent.
[0300] As used herein, a substituent of a monovalent group (eg, alkyl) may also independently be a substituent of the corresponding divalent group (eg, alkylene).
[0301] The terms "hydrogen" and "deuterium" refer to their respective atoms and corresponding radicals, and the terms "-F, -Cl, -Br, and -I" refer to fluorine, chlorine, bromine, and iodine radicals, respectively.
[0302] Unless otherwise defined, * and *' as used herein refer to the binding sites to adjacent atoms in the corresponding formula.
[0303] Hereinafter, compounds according to some exemplary embodiments and light-emitting devices according to some exemplary embodiments will be described in detail with reference to examples. The expression "using B instead of A" used in describing the examples means using the same molar equivalent of B instead of the same molar equivalent of A.
[0304] Example
[0305] Manufacturing of light-emitting devices
[0306] Comparative Example 1
[0307] Will The glass substrate (anode) was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonicated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposing to ultraviolet rays and ozone for 30 minutes. The ITO glass substrate was then provided to a vacuum deposition apparatus.
[0308] On an ITO glass substrate, compound 400 and p-dopant (HAT-CN) were vacuum deposited at a weight ratio of 1:0.1 to form a Then, a p-doped hole transport layer having a thickness of 1000 nm is formed, and a compound 400 as a hole transport compound is vacuum-deposited thereon to form a hole transport layer having a thickness of 1000 nm. The hole transport layer has a thickness of .
[0309] On the hole transport layer, compound G100 and p-dopant (HAT-CN) were formed at a weight ratio of 1:0.1. Then, compound G100 is vacuum deposited thereon to form a The emission auxiliary layer has a thickness of .
[0310] On the emission auxiliary layer, compounds HT100 and ET100 (weight ratio of 70:30) as hosts and compound D100 (based on the total weight of the host and the dopant, 10 wt%) as a dopant were co-deposited to form a The thickness of the emission layer.
[0311] Next, compound ET400 is formed into to form a buffer layer, on which a compound 500 as an electron transport compound is deposited to form a The thickness of the electron transport layer is .
[0312] An alloy AgMg (Mg is 10 wt% based on the total AgMg weight) is vacuum deposited on the electron transport layer to form a A cathode with a thickness of is formed, thereby completing the manufacture of the light-emitting device.
[0313]
[0314]
[0315] Comparative Example 2
[0316] A light-emitting device was prepared in the same manner as in Comparative Example 1, except that compound HT100, compound ET100 and compound ET200 were used as the main body in a weight ratio of 70:20:10, and compound D100 was used as the dopant (10 wt % based on the total weight of the composition) when forming the emission layer, wherein the above-mentioned main body and dopant were co-deposited.
[0317] Comparative Example 3
[0318] A light-emitting device was prepared in the same manner as in Comparative Example 1, except that compound HT100 and compound ET200 were used as the main body in a weight ratio of 70:30 when forming the emission layer, and compound D100 was used as the dopant (10 wt % based on the total weight of the composition), wherein the above-mentioned main body and dopant were co-deposited, and compound ET200 was used when forming the buffer layer.
[0319] Example 1
[0320] A light-emitting device was prepared in the same manner as in Comparative Example 1, except that compound HT100, compound ET100 and compound ET200 were used as the main body in a weight ratio of 70:20:10 when forming the emission layer, and compound D100 was used as the dopant (10 wt % based on the total weight of the composition), wherein the above-mentioned main body and dopant were co-deposited, and compound ET200 was used when forming the buffer layer.
[0321] The HOMO energy level value and the LUMO energy level value were measured using a surface analyzer sold under the trade name AC3 by RIKEN KEIKI Co., Ltd. in Tokyo, Japan, and the HOMO energy level value and the LUMO energy level value of each of Compound HT100, Compound ET100, Compound ET200, and Compound ET400 are as follows:
[0322] Table 1
[0323] Compound HOMO(eV) LUMO(eV) HT100 -5.51 -1.81 ET100 5.61 2.13 ET200 5.70 2.03 ET400 -5.82 -1.95
[0324] In order to evaluate the characteristics of the light emitting devices manufactured according to Comparative Examples 1 to 3 and Example 1, the current at 10 mA / cm 2Driving voltage, efficiency, life, etc. at current density.
[0325] The driving voltage and current density of the light emitting device were measured by using a source meter (Keithley Instruments, Tektronix, Beaverton, OR, 2400 Series), and the efficiency of the light emitting device was measured by using a measuring instrument manufactured by Hamamatsu Photonics Co., Ltd., Hamamatsu, Japan.
[0326] Table 2
[0327]
[0328] Referring to Table 2, it was confirmed that the light-emitting device of Example 1 showed significantly and unexpectedly excellent results in terms of efficiency and long life compared to the efficiency and life of the light-emitting devices manufactured according to Comparative Examples 1 to 3. According to the principles of the invention and one or more exemplary embodiments, a light-emitting device can have both significantly and unexpectedly excellent efficiency and life.
[0329] Although certain exemplary embodiments and implementations have been described herein, other embodiments and modifications will be apparent from this description. Therefore, the inventive concept is not limited to such embodiments, but rather to the broader scope of the claims and various obvious modifications and equivalent arrangements as will be apparent to those skilled in the art.
Claims
1. A light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an intermediate layer disposed between the first electrode and the second electrode and comprising an emission layer, wherein the intermediate layer further comprises: i) a hole transport region disposed between the first electrode and the emission layer; and ii) an electron transport region disposed between the emission layer and the second electrode; wherein: The emissive layer includes three or more hosts; The electron transport region includes a buffer layer; The three or more hosts include a hole transport host, a first electron transport host, and a second electron transport host; The buffer layer is composed of a third electron transport host; The lowest unoccupied molecular orbital energy level of the second electron transport host is equal to the lowest unoccupied molecular orbital energy level of the third electron transport host; and The second electron transport host and the third electron transport host are the same compound.
2. The light emitting device according to claim 1, wherein The highest occupied molecular orbital energy level of the second electron transport host is equal to the highest occupied molecular orbital energy level of the third electron transport host.
3. The light emitting device according to claim 1, wherein The lowest unoccupied molecular orbital energy level of the hole transport host, the lowest unoccupied molecular orbital energy level of the first electron transport host, and the lowest unoccupied molecular orbital energy level of the second electron transport host satisfy the following inequalities (1) and (2): |E LUMO_HT |>|E LUMO_ET1 |(1);sum |And LUMO_HT |>|And LUMO_ET2 |(2), Among them, E LUMO_HT represents the lowest unoccupied molecular orbital energy level of the hole transport host, E LUMO_ET1 represents the lowest unoccupied molecular orbital energy level of the first electron transport host, and E LUMO_ET2 represents the lowest unoccupied molecular orbital energy level of the second electron transport host. The light emitting device according to claim 1 , wherein: The highest occupied molecular orbital energy level of the hole transport host, the highest occupied molecular orbital energy level of the first electron transport host, and the highest occupied molecular orbital energy level of the second electron transport host satisfy the following inequality (3): |And HOMO_ET2 |>|And HOMO_ET1 |>|And HOMO_HT |(3), Among them, E HOMO_ET2 represents the highest occupied molecular orbital energy level of the second electron transport host, E HOMO_ET1 represents the highest occupied molecular orbital energy level of the first electron transport host, and E HOMO_HT represents the highest occupied molecular orbital energy level of the hole transport host. The light emitting device according to claim 1 , wherein: The lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the first electron transport host and the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the second electron transport host satisfy the following inequalities (4) and (5): |E LUMO_ET2 |>|E LUMO_ET1 |(4);sum |And HOMO_ET2 |>|And HOMO_ET1 |(5), Among them, E LUMO_ET1 and E HOMO_ET1 represent the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the first electron transport host, respectively, and E LUMO_ET2 and E HOMO_ET2 represent the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the second electron transport host, respectively. The light emitting device according to claim 1 , wherein: The lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the first electron transport host and the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the second electron transport host satisfy the following inequalities (6) and (7): |E LUMO_ET2 -E LUMO_ET1 |≤0.1eV(6); and |E HOMO_ET2 -E HOMO_ET1 |≤0.1eV(7), Among them, E LUMO_ET1 and E HOMO_ET1 represent the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the first electron transport host, respectively, and E LUMO_ET2 and E HOMO_ET2 represent the lowest unoccupied molecular orbital energy level and the highest occupied molecular orbital energy level of the second electron transport host, respectively.
7. The light emitting device according to claim 1, wherein The buffer layer at least partially contacts the emission layer. The light emitting device according to claim 1 , wherein: The electron transport region further includes an electron transport layer, and the buffer layer at least partially contacts the electron transport layer.
9. The light emitting device according to claim 1, wherein The hole transport region includes an emission assisting layer, and the emission assisting layer includes a charge generating material.
Citation Information
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