Organic compound and organic light-emitting device including the same
By using the organic compound represented by Formula 1 as the luminescent layer material in OLED, the problem of short life of OLED is solved, and the luminescent efficiency and life are improved.
Patent Information
- Application Number
- CN202211348368.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-12-30
- Filing Date
- 2022-10-31
- Publication Date
- 2025-08-08
- Estimated Expiration
- 2042-10-31
AI Technical Summary
The lifetime of existing organic light emitting diodes (OLEDs) still have limitations, affecting their application in flat panel display devices.
The luminescence efficiency and lifetime of OLED are improved by adopting organic compounds of a specific structure, including the compounds represented by Formula 1 as the organic light emitting layer material.
By using improved organic compound materials, the lifetime of OLEDs is extended and the luminous efficiency is improved.
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Figure CN116410187B_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0193029, filed in Korea on December 30, 2021, which is hereby incorporated by reference in its entirety. Technical Field
[0003] The present disclosure relates to an organic compound, and more particularly, to an organic compound having improved luminous efficiency and lifetime and an organic light-emitting device including the organic compound. Background Art
[0004] Recently, as demand for flat panel display devices having a smaller footprint increases, organic light emitting display devices including organic light emitting diodes (OLEDs) have become the subject of recent research and development.
[0005] OLED injects electrons from the cathode as the electron injection electrode and holes from the anode as the hole injection electrode into the light-emitting material layer (EML), combines the electrons with the holes, generates excitons, and converts the excitons from the excited state to the ground state to emit light. Flexible substrates, such as plastic substrates, can be used as base substrates for forming elements. In addition, organic light-emitting display devices can operate at a voltage lower than that of other display devices (for example, 10V or less). In addition, organic light-emitting display devices have advantages in power consumption and color perception.
[0006] The OLED includes a first electrode as an anode on a substrate, a second electrode as a cathode spaced apart from and facing the first electrode, and an organic light emitting layer between the first and second electrodes.
[0007] Although much research and development has been done on materials for organic light-emitting layers, the lifespan of OLEDs is still limited. Summary of the Invention
[0008] The present disclosure relates to an organic compound and an organic light-emitting device including the same that substantially obviate one or more problems associated with limitations and disadvantages of the related art.
[0009] The additional features and advantages of the present disclosure are set forth in the following description, which will become apparent from the description or may be clarified through the practice of the present disclosure. The purpose and other advantages of the present disclosure are realized and obtained through the features described herein and in the accompanying drawings.
[0010] To achieve these and other advantages for the purposes of embodiments according to the present disclosure, as described herein, one aspect of the present disclosure is an organic compound represented by Formula 1:
[0011] [Formula 1]
[0012]
[0013] wherein L1 is a substituted or unsubstituted C5 to C30 heteroaryl group, and L2 is selected from the group consisting of a single bond, and a substituted or unsubstituted C6 to C30 aryl group, wherein one of X1 and X2 is a nitrogen atom, and the other of X1 and X2 is O or S, wherein Ar1, Ar2 and Ar3 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C10 alkylthioxy group, a substituted or unsubstituted The present invention further comprises a group consisting of a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C10 alkylsulfoxide group, a substituted or unsubstituted C6 to C30 arylsulfoxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, wherein Ar4 and Ar5 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, and wherein a1 is an integer from 0 to 95, a2, a3, a4 and a5 are each independently an integer from 0 to 30, and at least one of a1 to a5 is a positive integer.
[0014] Another aspect of the present disclosure is an organic light-emitting device including: a substrate; and an organic light-emitting diode, the organic light-emitting diode being on the substrate and including a first electrode; a second electrode facing the first electrode; and a first light-emitting portion between the first electrode and the second electrode, the first light-emitting portion including a first green light-emitting material layer, wherein the first green light-emitting material layer includes a first compound, the first compound being an organic compound represented by Formula 1:
[0015] [Formula 1]
[0016]
[0017] wherein L1 is a substituted or unsubstituted C5 to C30 heteroaryl group, and L2 is selected from the group consisting of a single bond, and a substituted or unsubstituted C6 to C30 aryl group, wherein one of X1 and X2 is a nitrogen atom, and the other of X1 and X2 is O or S, wherein Ar1, Ar2 and Ar3 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C10 alkylthioxy group, a substituted or unsubstituted The present invention further comprises a group consisting of a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C10 alkylsulfoxide group, a substituted or unsubstituted C6 to C30 arylsulfoxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, wherein Ar4 and Ar5 are each independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, and wherein a1 is an integer from 0 to 95, a2, a3, a4 and a5 are each independently an integer from 0 to 30, and at least one of a1 to a5 is a positive integer.
[0018] 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 disclosure as claimed. BRIEF DESCRIPTION OF THE DRAWINGS
[0019] The accompanying drawings are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the disclosure and together with the description serve to explain the principles of the disclosure.
[0020] Figure 1 A schematic circuit diagram of an organic light emitting display device according to an exemplary embodiment of the present disclosure is shown.
[0021] Figure 2 A schematic cross-sectional view illustrating an organic light emitting display device according to a first embodiment of the present disclosure is shown.
[0022] Figure 3 A schematic cross-sectional view of an OLED according to a second embodiment of the present disclosure is shown.
[0023] Figure 4 A schematic cross-sectional view of an OLED according to a third embodiment of the present disclosure is shown.
[0024] Figure 5 A schematic cross-sectional view illustrating an organic light emitting display device according to a fourth embodiment of the present disclosure is shown.
[0025] Figure 6 A schematic cross-sectional view of an OLED according to a fifth embodiment of the present disclosure is shown.
[0026] Figure 7 A schematic cross-sectional view of an OLED according to a sixth embodiment of the present disclosure is shown. DETAILED DESCRIPTION
[0027] Reference will now be made in detail to some embodiments and implementations of the present disclosure, which are illustrated in the accompanying drawings. Wherever possible, the same reference numerals will be used throughout the drawings to refer to the same or like parts.
[0028] The advantages and features of the present disclosure and its implementation methods will be illustrated by the exemplary embodiments described below in conjunction with the accompanying drawings. However, the present disclosure can be embodied in different forms and should not be construed as being limited to the exemplary embodiments set forth herein. Rather, these exemplary embodiments are provided so that the present disclosure can be sufficiently thorough and complete to help those skilled in the art fully understand the scope of the present disclosure. In addition, the scope of protection of the present disclosure is defined by the claims and their equivalents.
[0029] The shapes, sizes, ratios, angles, quantities, etc. shown in the accompanying drawings to describe the various exemplary embodiments of the present disclosure are given by way of example only. Therefore, the present disclosure is not limited to the description in the accompanying drawings. Unless otherwise specified, the same or similar elements are represented by the same reference numerals throughout the specification.
[0030] In the following description, where a detailed description of related known functions or configurations may unnecessarily obscure the main points of the present disclosure, a detailed description of such known configuration functions may be omitted.
[0031] In this specification, when the terms "comprising," "having," "including," etc. are used, one or more other elements may be added unless a term such as "only" is used. Elements described in the singular are intended to include plural elements, and vice versa, unless the context clearly indicates otherwise.
[0032] When interpreting an element, the element is to be interpreted as including an error or tolerance range even in the case where an explicit description of such error or tolerance range is not provided.
[0033] In the description of various embodiments of the present disclosure, when describing a positional relationship, for example, when using “on,” “above,” “below,” “above,” “below,” “near,” “immediately adjacent,” etc. to describe the positional relationship between two parts, one or more other parts may be located between the two parts, unless more restrictive terms such as “immediately,” “directly,” or “immediately adjacent” are used. For example, when one element or layer is disposed “on” another element or layer, a third layer or element may be interposed therebetween.
[0034] When describing a temporal relationship, when the temporal order is described as, for example, "after," "subsequently," "next," or "before," discontinuities may be included unless more restrictive terms such as "just," "immediately," or "directly" are used.
[0035] Although the terms "first," "second," etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. For example, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element, without departing from the scope of this disclosure.
[0036] Although the terms "first," "second," A, B, (a), (b), etc. may be used herein to describe various elements, these elements should not be construed as limited by these terms, as they are not used to define a particular order, priority, or quantity of the corresponding elements. These terms are only used to distinguish one element from another.
[0037] When stating that an element or layer is “connected” to another element or layer, it means that the element or layer is not only directly connected to the other element or layer but also may be indirectly connected or adhered to the other element or layer with one or more intervening elements or layers “disposed” or “interposed” therebetween, unless otherwise specified.
[0038] The term "at least one" should be understood to include any and all combinations of one or more of the associated listed items. For example, the meaning of "at least one of a first element, a second element, and a third element" includes the combination of all three listed elements, the combination of any two of the three elements, and each individual element, the first element, the second element, and the third element.
[0039] The features of the various embodiments of the present disclosure may be coupled or combined with each other in part or in whole, and may interoperate with each other in various ways and be driven technically as will be fully understood by those skilled in the art. The embodiments of the present disclosure may be implemented independently of each other, or may be implemented together in an interdependent relationship.
[0040] Hereinafter, exemplary embodiments of the present disclosure will be described in detail with reference to the accompanying drawings. When reference numerals are added to the elements of each drawing, similar reference numerals may refer to similar elements even though the same elements are shown in other drawings. In addition, for ease of description, the scale of each element illustrated in the drawings may differ from the actual scale. Therefore, the illustrated elements are not limited to the specific scales they are illustrated in the drawings.
[0041] The OLED of the present disclosure may include an example of the organic compound of the present disclosure. The OLED may be included in an organic light-emitting display device or an organic light-emitting lighting device. The following explanation focuses on an example of an organic light-emitting display device including the OLED of the present disclosure.
[0042] Figure 1 A schematic circuit diagram of an organic light emitting display device according to an exemplary embodiment of the present disclosure is shown.
[0043] like Figure 1 As shown, gate lines GL and data lines DL, as well as power lines PL, which may intersect with each other to define pixels (pixel regions) P, may be formed in an organic light display device. A switching thin film transistor (TFT) Ts, a driving thin film transistor (TFT) Td, a storage capacitor Cst, and an OLED D may be formed in each pixel P. The pixel P may include a red pixel, a green pixel, and a blue pixel. In addition, the pixel P may further include a white pixel.
[0044] A switching thin film transistor Ts may be connected to the gate line GL and the data line DL, and a driving thin film transistor Td and a storage capacitor Cst may be connected between the switching thin film transistor Ts and the power line PL. An OLED D may be connected to the driving thin film transistor Td. When a gate signal applied via the gate line GL turns on the switching thin film transistor Ts, a data signal applied via the data line DL may be applied to the gate electrode of the driving thin film transistor Td and one electrode of the storage capacitor Cst via the switching thin film transistor Ts.
[0045] The driving thin-film transistor Td is turned on by a data signal applied to its gate electrode, allowing a current proportional to the data signal to be supplied from the power line PL to the OLED D through the driving thin-film transistor Td. The OLED D can emit light with a brightness proportional to the current flowing through the driving thin-film transistor Td. In this case, the storage capacitor Cst can be charged with a voltage proportional to the data signal, so that the voltage of the gate electrode of the driving thin-film transistor Td can remain constant or similar during a frame. As a result, the organic light-emitting display device can display a desired image.
[0046] Figure 2 A schematic cross-sectional view illustrating an organic light emitting display device according to a first embodiment of the present disclosure is shown.
[0047] like Figure 2 As shown, the organic light-emitting display device 100 may include a substrate 110, a TFT Tr, and an OLED D connected to the TFT Tr. For example, the organic light-emitting display device 100 may include a red pixel, a green pixel, and a blue pixel, and the OLED D may be formed in each of the red pixel, the green pixel, and the blue pixel. For example, an OLED D emitting red light, green light, and blue light may be provided in the red pixel, the green pixel, and the blue pixel, respectively.
[0048] The substrate 110 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.
[0049] The buffer layer 120 may be formed on the substrate, and the TFT Tr may be formed on the buffer layer 120. The buffer layer 120 may be omitted.
[0050] The semiconductor layer 122 may be formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polysilicon.
[0051] When the semiconductor layer 122 includes an oxide semiconductor material, a light-shielding pattern (not shown) may be formed below the semiconductor layer 122. Light reaching the semiconductor layer 122 may be shielded or blocked by the light-shielding pattern, thereby preventing or reducing thermal degradation of the semiconductor layer 122. On the other hand, when the semiconductor layer 122 includes polycrystalline silicon, impurities may be doped into both sides of the semiconductor layer 122.
[0052] A gate insulating layer 124 may be formed on the semiconductor layer 122. The gate insulating layer 124 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.
[0053] The gate electrode 130 , which may be formed of a conductive material such as metal, may be formed on the gate insulating layer 124 to correspond to the center of the semiconductor layer 122 .
[0054] exist Figure 2 In the embodiment, the gate insulating layer 124 may be formed on the entire surface of the substrate 110. Alternatively, the gate insulating layer 124 may be patterned to have the same shape as the gate electrode 130. However, embodiments of the present disclosure are not limited to these examples.
[0055] An interlayer insulating layer 132, which may be formed of an insulating material, may be formed on the gate electrode 130. The interlayer insulating layer 132 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo-acryl.
[0056] The interlayer insulating layer 132 may include a first contact hole 134 and a second contact hole 136 exposing both sides of the semiconductor layer 122. The first contact hole 134 and the second contact hole 136 may not cover a portion of the surface of the semiconductor layer 122 closer to opposite ends than the center of the semiconductor layer 122. The first contact hole 134 and the second contact hole 136 may be located on both sides of the gate electrode 130 to be spaced apart from the gate electrode 130.
[0057] The first contact hole 134 and the second contact hole 136 may be formed through the gate insulating layer 124. Alternatively, when the gate insulating layer 124 is patterned to have the same shape as the gate electrode 130, the first contact hole 134 and the second contact hole 136 may be formed through only the interlayer insulating layer 132. However, embodiments of the present disclosure are not limited to these examples.
[0058] A source electrode 140 and a drain electrode 142 , which may be formed of a conductive material such as metal, may be formed on the interlayer insulating layer 132 .
[0059] The source electrode 140 and the drain electrode 142 may be spaced apart from each other with respect to the gate electrode 130 and may contact both sides of the semiconductor layer 122 through the first contact hole 134 and the second contact hole 136 , respectively.
[0060] The semiconductor layer 122, the gate electrode 130, the source electrode 140, and the drain electrode 142 may constitute a TFT Tr. The TFT Tr may be used as a driving element. For example, the TFT Tr may correspond to a driving TFT Td ( Figure 1 ).
[0061] In the TFT Tr, the gate electrode 130, the source electrode 140, and the drain electrode 142 may be positioned on the semiconductor layer 122. For example, the TFT Tr may have a coplanar structure.
[0062] Alternatively, in the TFT Tr, the gate electrode may be located below the semiconductor layer, and the source electrode and the drain electrode may be located on the semiconductor layer, so that the TFT Tr may have an inverted staggered structure. In this case, the semiconductor layer may include amorphous silicon. However, the embodiments of the present disclosure are not limited to these examples.
[0063] Although not shown, the gate lines and the data lines may cross each other to define pixels, and a switching TFT may be formed to be connected to the gate lines and the data lines. The switching TFT may be connected to a TFT Tr as a driving element.
[0064] In addition, a power line and a storage capacitor for maintaining a voltage of a gate electrode of the TFT Tr in one frame may be further formed. The power line may be formed parallel to and spaced apart from one of the gate line and the data line.
[0065] A planarization layer (or passivation layer) 150 may be formed to cover the TFT Tr and may include a drain contact hole 152 exposing the drain electrode 142 of the TFT Tr. The drain contact hole 152 may not cover the drain electrode 142.
[0066] A first electrode 160 may be formed in each pixel and on the planarization layer 150, respectively. The first electrode 160 may be connected to the drain electrode 142 of the TFT Tr via the drain contact hole 152. The first electrode 160 may be an anode and may be formed of a conductive material having a relatively high work function. For example, the first electrode 160 may be formed of a transparent conductive material such as indium tin oxide (ITO) or indium zinc oxide (IZO).
[0067] When the organic light-emitting display device 100 operates as a bottom emission type, the first electrode 160 may have a single-layer structure of a transparent conductive material layer. Alternatively, when the organic light-emitting display device 100 operates as a top emission type, the first electrode 160 may further include a reflective layer. For example, the reflective layer may be formed of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In a top emission type organic light-emitting display device 100, the first electrode 160 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO. However, embodiments of the present disclosure are not limited to these examples.
[0068] The bank layer 166 may be formed on the planarization layer 150 to cover the edge of the first electrode 160. For example, the bank layer 166 may be located at the boundary of the pixel and expose the center of the first electrode 160 in the pixel. The bank layer 166 may not cover the center of the first electrode 160 in the pixel.
[0069] The organic light-emitting layer 162 may be formed on the first electrode 160. The organic light-emitting layer 162 may include a single light-emitting portion including a light-emitting material layer (EML). Alternatively, the organic light-emitting layer 162 may include a plurality of light-emitting portions, each of which may include an EML. In addition, the organic light-emitting layer 162 may further include a charge generation layer located between adjacent light-emitting portions. Embodiments of the present disclosure are not limited to these examples.
[0070] The light-emitting portion or each of the plurality of light-emitting portions may have a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL).
[0071] The organic light emitting layer 162 may be separated in each of the red pixel, the green pixel, and the blue pixel. As described herein, in the OLED D in the green pixel according to the exemplary embodiment of the present disclosure, the EML may include an example of the organic compound of the present disclosure, thereby extending the life of the OLED D and the organic light emitting display device 100 including the organic compound.
[0072] The second electrode 164 may be formed above the substrate 110 on which the organic light-emitting layer 162 is formed. The second electrode 164 may cover the entire surface of the display area and may be formed of a conductive material having a relatively low work function to serve as a cathode. For example, the second electrode 164 may be formed of aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or alloys thereof, or a combination thereof. In a top-emission organic light-emitting display device 100, the second electrode 164 may have a thin profile (small thickness) to provide light-transmitting properties (or semi-light-transmitting properties).
[0073] The first electrode 160 , the organic light emitting layer 162 , and the second electrode 164 may constitute an OLED D.
[0074] An encapsulation film (e.g., an encapsulation layer) 170 may be formed on the second electrode 164 to prevent moisture from penetrating into the OLED D. The encapsulation film 170 may include a first inorganic insulating layer 172, an organic insulating layer 174, and a second inorganic insulating layer 176 sequentially stacked. However, embodiments of the present disclosure are not limited to these examples. The encapsulation film 170 may be omitted.
[0075] The organic light-emitting display device 100 may further include a polarizing plate (not shown) for reducing ambient light reflection. For example, the polarizing plate may be a circular polarizing plate. In a bottom-emission organic light-emitting display device 100, the polarizing plate may be disposed below the substrate 110. In a top-emission organic light-emitting display device 100, the polarizing plate may be disposed on or above the encapsulation film 170.
[0076] In addition, in the top emission type organic light emitting display device 100, a cover window (not shown) may be attached to the packaging film 170 or the polarizing plate. In this case, the substrate 110 and the cover window may have flexible characteristics, thereby providing a flexible organic light emitting display device.
[0077] Figure 3 A schematic cross-sectional view of an OLED according to a second embodiment of the present disclosure is shown.
[0078] like Figure 3 As shown, the OLED D may include a first electrode 160 and a second electrode 164 that may face each other, and an organic light emitting layer 162 therebetween. The organic light emitting layer 162 may include a green EML 230 between the first electrode 160 and the second electrode 164.
[0079] ( Figure 2 The organic light-emitting display device 100 may include red pixels, green pixels, and blue pixels. The OLED D may be located in the green pixel. The OLED D in the red pixel may include a red EML, and the OLED D in the blue pixel may include a blue EML.
[0080] The first electrode 160 may be an anode that injects holes, and the second electrode 164 may be a cathode that injects electrons. In addition, one of the first electrode 160 and the second electrode 164 may be a reflective electrode, and the other may be a transparent (or semi-transparent) electrode.
[0081] For example, the first electrode 160 may include a transparent conductive material layer formed of ITO or IZO. The second electrode 164 may be formed of one of Al, Mg, Ag, AlMg, and MgAg.
[0082] The green EML 230 may include an example of an organic compound of the present disclosure as a first compound 232. The first compound 232 may be represented by Formula 1.
[0083] [Formula 1]
[0084]
[0085] In Formula 1, L1 may be a substituted or unsubstituted C5 to C30 heteroarylene group, and L2 may be selected from the group consisting of a single bond (direct bond) and a substituted or unsubstituted C6 to C30 arylene group. One of X1 and X2 may be a nitrogen atom (N), and the other of X1 and X2 may be O or S. Ar1, Ar2 and Ar3 can each be independently selected from the group consisting of hydrogen (H), deuterium (D), substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C1 to C10 alkylthioxy, substituted or unsubstituted C6 to C30 arylthioxy, substituted or unsubstituted C1 to C10 alkylsulfoxide, substituted or unsubstituted C6 to C30 arylsulfoxide, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl. Ar4 and Ar5 can each be independently selected from the group consisting of substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl. In addition, a1 may be an integer from 0 to 95, a2, a3, a4, and a5 may each independently be an integer from 0 to 30, and at least one of a1 to a5 may be a positive integer. In Formula 1, D represents a deuterium atom, and each of a1 to a5 represents the number of deuterium atoms.
[0086] In the present disclosure, unless otherwise specifically defined, the substituent of the alkyl group, cycloalkyl group, alkoxy group, aryloxy group, alkylthiooxy group, arylthiooxy group, alkylsulfoxide group, arylsulfoxide group, aryl group, heteroaryl group, arylene group, and heteroarylene group may be selected from the group consisting of deuterium, C1 to C10 alkyl group, and C6 to C30 aryl group.
[0087] In the present disclosure, unless otherwise specifically defined, the C6 to C30 aryl group may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pentanenyl, indenyl, indenoindenyl, heptalenyl, biphenylenyl, indacenyl, phenanthrenyl, benzophenanthrenyl, dibenzophenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, triphenylenyl, The C6 to C30 arylene group may be a divalent group derived from a carbon atom in a group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pentenyl, indenyl, indenoindenyl, heptenyl, biphenylenyl, indenylphenyl, phenanthrenyl, triphenylenyl, diphenylphenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, triphenylenyl, phenyl, tetraphenyl, naphthacene, dinaphthophenyl, pentaphenyl, pentacene, fluorenyl, indenofluorenyl, and spirofluorenyl.
[0088] In the present disclosure, unless otherwise specifically defined, the C3 to C30 heteroaryl group may be selected from the group consisting of pyrrolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, indolyl, isoindolyl, indazolyl, indolizinyl, pyrrolizinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, benzofurancarbazolyl, benzothiophenecarbazolyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, cinnamyl, quinazolinyl, quinolozolinyl, purinyl, benzoquinolyl, benzisoquinolyl, Quinolinyl, benzoquinazolinyl, benzoquinoxalinyl, acridinyl, phenanthrolinyl, piperidinyl, phenanthridinyl, pteridinyl, cinnolinyl, naphthylamino, furanyl, oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxinyl, benzofuranyl, dibenzofuranyl, thienyl, xanthenyl, benzopyranyl, isobenzopyranyl, thiazinyl, thienyl, benzothienyl, dibenzothienyl, difurylpyrazinyl, benzofuran-dibenzofuranyl, benzothiophene-benzothienyl, benzothiophene-dibenzothienyl, benzothiophene-benzofuranyl, and benzothiophene-dibenzofuranyl. Likewise, the C3 to C30 heteroarylene group may be a divalent group derived by removing a hydrogen atom from a carbon atom in a group selected from the group consisting of a pyrrolyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a tetrazinyl group, an imidazolyl group, a pyrazolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a pyrrolizinyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an indolocarbazolyl group, an indenocarbazolyl group, a benzofurancarbazolyl group, a benzothiophenecarbazolyl group, a quinolyl group, an isoquinolyl group, a phthalazinyl group, a quinoxalinyl group, a cinnamyl group, a quinazolinyl group, a quinolozolinyl group, a purinyl group, a benzoquinolyl group , benzoisoquinolinyl, benzoquinazolinyl, benzoquinoxalinyl, acridinyl, phenanthrolinyl, piperidinyl, phenanthridinyl, pteridinyl, cinnolinyl, naphthylamino, furanyl, oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxinyl, benzofuranyl, dibenzofuranyl, thienyl, xanthenyl, benzopyranyl, isobenzopyranyl, thiazinyl, thienyl, benzothienyl, dibenzothienyl, difurylpyrazinyl, benzofuran-dibenzofuranyl, benzothiophene-benzothienyl, benzothiophene-dibenzothienyl, benzothiophene-benzofuranyl, and benzothiophene-dibenzofuranyl.
[0089] In the example of the organic compound of Formula 1, at least one hydrogen atom is replaced by a deuterium atom, thereby increasing the luminescence lifetime of the organic compound. In other words, the deuterium substitution rate of the organic compound may be greater than 0 and less than 100.
[0090] For example, in Formula 1, all of a1 to a5 may be positive integers, allowing the organic compound to be fully deuterated. In an exemplary embodiment, a1 may be a positive integer, and a2 to a5 may be 0. In an exemplary embodiment, a1 and a2 may be positive integers, and a3, a4, and a5 may be 0. For example, the organic compound may be partially deuterated. When a1 is a positive integer and at least one of a2 to a5 is a positive integer or a non-positive integer, the luminescence lifetime may be improved with a minimum of deuterium atoms.
[0091] For example, Formula 1 may be represented by one of Formula 1-1, Formula 1-2, and Formula 1-3.
[0092] [Formula 1-1]
[0093]
[0094] [Formula 1-2]
[0095]
[0096] [Formula 1-3]
[0097]
[0098] In Formulas 1-1 to 1-3, the definitions of L1, L2, Ar1 to Ar5, and a1 to a5 may be the same as those in Formula 1.
[0099] For example, L1 may be one of carbazole, dibenzofuran, and dibenzothiophene. For example, L1 may be one of the structures of Formula 1a, Formula 1b, Formula 1c, and Formula 1d.
[0100] [Formula 1a]
[0101]
[0102] [Formula 1b]
[0103]
[0104] [Formula 1c]
[0105]
[0106] [Formula 1d]
[0107]
[0108] In Formula 1a, Formula 1b, Formula 1c and Formula 1d, R1, R2 and R3 can each be independently selected from deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C1 to C10 alkylthio, substituted or unsubstituted C6 to C30 arylthio, substituted or unsubstituted C1 to C wherein the group consisting of a substituted or unsubstituted C6 to C30 alkylsulfoxide group, a substituted or unsubstituted C6 to C30 arylsulfoxide group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, a substituted or unsubstituted C6 to C30 arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, b1 may be an integer from 0 to 3, and b2, b3, and b4 may each independently be an integer from 0 to 4. In Formulas 1a, 1b, 1c, and 1d, one of the wavy mark and the “*” mark is a bonding site to the fused fluorene moiety, and the other of the wavy mark and the “*” mark is a bonding site to L2.
[0109] For example, the nitrogen atom of the carbazole moiety in Formula 1a can be bonded to the fused fluorene moiety or L2 as a linking group.
[0110] For example, Formula 1a, Formula 1b, Formula 1c, and Formula 1d can be represented by Formula 1a-1, Formula 1b-1, Formula 1c-1, and Formula 1d-1, respectively.
[0111] [Formula 1a-1]
[0112]
[0113] [Formula 1b-1]
[0114]
[0115] [Formula 1c-1]
[0116]
[0117] [Formula 1d-1]
[0118]
[0119] In Formulas 1a-1, 1b-1, 1c-1, and 1d-1, R1 to R3 and b1 to b4 may be defined the same as those in Formulas 1a, 1b, 1c, and 1d, respectively. In Formulas 1a-1, 1b-1, 1c-1, and 1d-1, one of the wavy mark and the “*” mark may be a bonding site to the fused fluorene moiety, and the other of the wavy mark and the “*” mark may be a bonding site to L2.
[0120] In Formula 1, L2 can be a single bond or a phenylene group. Ar1 can be selected from hydrogen, deuterium, and a substituted or unsubstituted C6 to C30 aryl group, such as a phenyl group. Ar2 and Ar3 can each independently be hydrogen or deuterium, and Ar4 and Ar5 can be a substituted or unsubstituted C6 to C30 aryl group, such as a phenyl group.
[0121] The first compound 232 , which is an example of an organic compound of the present disclosure, may be one of the compounds in Formula 2.
[0122] [Formula 2]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138]
[0139]
[0140]
[0141]
[0142]
[0143]
[0144]
[0145]
[0146] [synthesis]
[0147] 1. Synthesis of Intermediates (1) Intermediate 1A [Reaction Formula 1-1]
[0148]
[0149] In a round-bottom flask, 7-bromobenzoxazole (15 g, 0.061 mol), bis(pinacol)diboron (23.3 g, 0.092 mol), [1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II)] (0.90 g, 1.22 mmol), KOAc (potassium acetate, 12.01 g, 0.122 mol) and 225 ml of 1,4-dioxane were added. After increasing the temperature of the mixture, the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and filtered using celite. The residual solution was concentrated under reduced pressure and recrystallized using dichloromethane to obtain 12.5 g of Intermediate 1A.
[0150] (2) Intermediate 1B
[0151] [Reaction formula 1-2]
[0152]
[0153] In a round-bottom flask, methyl 5-bromo-iodobenzoate (15 g, 0.044 mol), intermediate 1A (11.9 g, 0.048 mol), tetrakis(triphenylphosphine)palladium(0) (1.02 g, 0.880 mmol), 225 ml of toluene, 30 ml of EtOH (ethanol), and 45 ml of 4M KCO (potassium carbonate) were added, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the reaction solution was filtered to obtain a crude product. The filtered crude product was separated by column chromatography with dichloromethane and hexane to obtain 12.4 g of intermediate 1B.
[0154] (3) Intermediate 1C
[0155] [Reaction formula 1-3]
[0156]
[0157] In a round-bottom flask, intermediate 1B (12.0 g, 0.030 mol) was added, and 150 ml of anhydrous THF (tetrahydrofuran) was added. The mixture was stirred under a nitrogen atmosphere. 61.9 ml of methylmagnesium bromide diluted in 60 ml of anhydrous THF was slowly added dropwise to the solution. The solution was stirred for 6 hours. After the reaction was complete, 180 ml of a 10% NH4Cl aqueous solution was added to the reaction solution and stirred for 1 hour. The mixture was extracted with EA (ethyl acetate), the organic layer was collected and concentrated under reduced pressure to obtain 20.2 g of intermediate 1C.
[0158] (4) Intermediate 1D
[0159] [Reaction formula 1-4]
[0160]
[0161] In a round-bottom flask, intermediate 1C (20.0 g, 0.045 mol), 300 ml of acetic acid and 30 ml of hydrochloric acid were added, and the mixture was heated to reflux and stirred for 2 hours. After the reaction was completed, the reaction solution was poured into distilled water, crystallized, and the precipitate was filtered. The filtered precipitate was dissolved in 100 ml of MC (dichloromethane) and dried with MgSO4. Then, the mixture was precipitated again using MC and ethanol to obtain 15.1 g of intermediate 1D.
[0162] (5) Intermediate 1D-D
[0163] [Reaction formula 1-5]
[0164]
[0165] In a round-bottom flask, intermediate 1D and benzene-D6 (50 times the amount of intermediate 1D) were added, and the mixture was refluxed and stirred. Trifluoromethanesulfonic acid (50 equivalents) was added at 70°C. After 5 hours, the mixture was cooled to room temperature. 40 ml of D2O was added and stirred for 10 minutes. The mixture was neutralized with aqueous K3PO4 solution, and the organic layer was extracted with ethyl acetate. After removing residual moisture with magnesium sulfate, the organic layer was distilled under reduced pressure and separated by column chromatography to obtain intermediate 1D-D in a yield of 72%.
[0166] (6) Intermediate 1D-DB
[0167] [Reaction formula 1-6]
[0168]
[0169] In the synthesis of intermediate 1A, 7-bromobenzoxazole was replaced with intermediate 1D-D to obtain intermediate 1D-DB in 83% yield.
[0170] (7) Intermediate 1D-Bc
[0171] [Reaction formula 1-7]
[0172]
[0173] In the synthesis of intermediate 1D-DB, intermediate 1D-D was replaced with intermediate 1D to obtain intermediate 1D-Bc in 85% yield.
[0174] (8) Intermediate 1AB
[0175] [Reaction formula 1-8]
[0176]
[0177] In the synthesis of Intermediate 1B, 5-bromo-iodobenzoic acid methyl ester was replaced with 4-bromo-2-iodobenzoic acid methyl ester to obtain 13.8 g of Intermediate 1AB.
[0178] (9) Intermediate 1AC
[0179] [Reaction formula 1-9]
[0180]
[0181] In the synthesis of Intermediate 1C, Intermediate 1B was replaced with Intermediate 1AB to obtain 20.4 g of Intermediate 1AC.
[0182] (10) Intermediate 1AD
[0183] [Reaction formula 1-10]
[0184]
[0185] In the synthesis of Intermediate 1D, Intermediate 1C was replaced with Intermediate 1AC to obtain 15 g of Intermediate 1AD.
[0186] (11) Intermediate 1AD-D
[0187] [Reaction formula 1-11]
[0188]
[0189] In the synthesis of intermediate 1D-D, intermediate 1D was replaced with intermediate 1AD to obtain intermediate 1AD-D in a yield of 73%.
[0190] (12) Intermediate 1AD-DB
[0191] [Reaction formula 1-12]
[0192]
[0193] In the synthesis of intermediate 1D-DB, intermediate 1D-D was replaced with intermediate 1AD-D to obtain intermediate 1AD-DB in 80% yield.
[0194] (13) Intermediate 1AD-B
[0195] [Reaction formula 1-13]
[0196]
[0197] In the synthesis of intermediate 1AD-DB, intermediate 1AD-D was replaced with intermediate 1AD-B to obtain intermediate 1AD-B in 83% yield.
[0198] 2. Synthesis of intermediates
[0199] (1) Intermediate 2A
[0200] [Reaction formula 2-1]
[0201]
[0202] Benzoic acid (10 g, 0.082 mol), 2-amino-6-bromophenol (33.9 g, 0.180 mol), diisopropylethylamine (37.1 ml, 0.213 mol), 82 ml of 4M K2CO3 aqueous solution and 300 ml of dichloromethane (MC) were added to a round-bottom flask, and the temperature of the mixture was lowered to 0°C under stirring. A deoxyfluorination reagent (50% in THF, 66 ml, 0.180 mol) diluted in 45 ml of MC was slowly added dropwise to the solution. After the addition was completed, the mixture was stirred at 0°C for 2 hours. After terminating the reaction by adding 100 ml of saturated sodium bicarbonate aqueous solution to the reaction solution, the mixture was warmed to room temperature. The reaction solution was separated, the organic layer was collected and dried over MgSO4 and concentrated under reduced pressure. The concentrated crude product was separated by column chromatography to obtain 18.4 g of intermediate 2A.
[0203] (2) Intermediate 2B
[0204] [Reaction formula 2-2]
[0205]
[0206] In the synthesis of Intermediate 1A, 7-bromobenzoxazole was replaced with Intermediate 2A to obtain 13.5 g of Intermediate 2B.
[0207] (3) Intermediate 2C
[0208] [Reaction formula 2-3]
[0209]
[0210] In the synthesis of Intermediate 1AB, Intermediate 1A was replaced with Intermediate 2B to obtain 14.2 g of Intermediate 2C.
[0211] (4) Intermediate 2D
[0212] [Reaction formula 2-4]
[0213]
[0214] In the synthesis of Intermediate 1C, Intermediate 1B was replaced with Intermediate 2C to obtain 17.3 g of Intermediate 2D.
[0215] (5) Intermediate 2E
[0216] [Reaction formula 2-5]
[0217]
[0218] In the synthesis of Intermediate 1D, Intermediate 1C was replaced with Intermediate 2D to obtain 11.5 g of Intermediate 2E.
[0219] (6) Intermediate 2E-D
[0220] [Reaction 2-6]
[0221]
[0222] In the synthesis of intermediate 1D-D, intermediate 1D was replaced with intermediate 2E to obtain intermediate 2E-D in 73% yield.
[0223] (7) Intermediate 2E-DB
[0224] [Reaction 2-7]
[0225]
[0226] In the synthesis of intermediate 1A, 7-bromobenzoxazole was replaced by intermediate 2E-D to obtain intermediate 2E-DB in 85% yield.
[0227] (8) Intermediate 2E-B
[0228] [Reaction formula 2-8]
[0229]
[0230] In the synthesis of intermediate 2E-DB, 2E-D was replaced with intermediate 2E to obtain intermediate 2E-B in 81% yield.
[0231] 3. Synthesis of intermediates
[0232] (1) Intermediate 3A
[0233] [Reaction formula 3-1]
[0234]
[0235] In the synthesis of Intermediate 1A, 7-bromobenzoxazole was replaced with 7-bromobenzothiazole to obtain 14.1 g of Intermediate 3A.
[0236] (2) Intermediate 3B
[0237] [Reaction formula 3-2]
[0238]
[0239] In the synthesis of Intermediate 1B, Intermediate 1A was replaced with Intermediate 3A to obtain 13.0 g of Intermediate 3B.
[0240] (3) Intermediate 3C
[0241] [Reaction formula 3-3]
[0242]
[0243] In the synthesis of Intermediate 1C, Intermediate 1B was replaced with Intermediate 3B to obtain 13.0 g of Intermediate 3C.
[0244] (4) Intermediate 3D
[0245] [Reaction formula 3-4]
[0246]
[0247] In the synthesis of Intermediate 1D, Intermediate 1C was replaced with Intermediate 3C to obtain 11 g of Intermediate 3D.
[0248] (5) Intermediate 3D-D
[0249] [Reaction formula 3-5]
[0250]
[0251] In the synthesis of intermediate 1D-D, intermediate 1D was replaced with intermediate 3D to obtain intermediate 3D-D in a yield of 75%.
[0252] (6) Intermediate 3D-DB
[0253] [Reaction formula 3-6]
[0254]
[0255] In the synthesis of intermediate 1A, 7-bromobenzoxazole was replaced with intermediate 3D-D to obtain intermediate 3D-DB in 82% yield.
[0256] (7) Intermediate 3D-B
[0257] [Reaction formula 3-7]
[0258]
[0259] In the synthesis of intermediate 3D-DB, intermediate 3D-D was replaced by intermediate 3D to obtain intermediate 3D-B in 81% yield.
[0260] 4. Synthesis of intermediates
[0261] (1) Intermediate TD
[0262] [Reaction formula 4-1]
[0263]
[0264] In a round-bottom flask, trichlorotriazine (30 g, 0.16 mol), phenylboron-D5 (41.3 g, 0.33 mol), tetrakis(triphenylphosphine)palladium(0) (7.5 g, 6.5 mmol), 600 ml of toluene, 60 ml of EtOH (ethanol), and 160 ml of 4M K2CO3 (potassium carbonate) were added, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the reaction solution was separated to remove water, and the organic layer was dried over MgSO4. The dried solution was concentrated under reduced pressure to remove all solvents and separated by column chromatography to obtain 31.6 g of intermediate TD with a yield of 70%.
[0265] (2) Intermediate CZD
[0266] [Reaction Formula 4-2]
[0267]
[0268] In the synthesis of intermediate 1D-D, intermediate 1D was replaced with 3-bromo-9H-carbazole to obtain intermediate CZD in a yield of 68%.
[0269] (3) Intermediate CZDB
[0270] [Reaction formula 4-3]
[0271]
[0272] In the synthesis of intermediate 1A, 7-bromobenzoxazole was replaced with intermediate CZD to obtain intermediate CZDB in 85% yield.
[0273] (4) Intermediate DBFD
[0274] [Reaction formula 4-4]
[0275]
[0276] In the synthesis of intermediate 1D-D, intermediate 1D was replaced with 4,6-dibromodibenzofuran to obtain intermediate DBFD in a yield of 66%.
[0277] (5) Intermediate TBD
[0278] [Reaction formula 4-5]
[0279]
[0280] In the synthesis of intermediate 1D-D, intermediate 1D was replaced with 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine to obtain intermediate TBD in a yield of 78%.
[0281] (6) Intermediate TBDB
[0282] [Reaction formula 4-6]
[0283]
[0284] In the synthesis of intermediate 1A, 7-bromobenzoxazole was replaced with intermediate TBD to obtain intermediate TBDB in 87% yield.
[0285] (7) Intermediate TBB
[0286] [Reaction formula 4-7]
[0287]
[0288] In the synthesis of intermediate 1A, 7-bromobenzoxazole was replaced with 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine to obtain intermediate TBB in 85% yield.
[0289] 5. Synthesis of Compound H1-D1
[0290] (1) Intermediate BB
[0291] [Reaction Formula 5-1]
[0292]
[0293] In a round-bottom flask, 3-bromocarbazole (5 g, 0.020 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.5 g, 0.024 mol), palladium acetate (Pd(OAc)2, 0.09 g, 0.406 mmol), sodium tert-butoxide (Na + t-BuO-, 3.91 g, 0.041 mol), tri-tert-butylphosphine (0.41 g, 2.03 mmol), and 75 ml of toluene were added and the mixture was refluxed and stirred for 10 hours. After cooling to room temperature, the mixture was extracted with EA and water. The mixture was dried over MgSO4 and concentrated under reduced pressure. The resulting crude product was separated by column chromatography to obtain 9.1 g of intermediate BB.
[0294] (2) Compound H1-D1
[0295] [Reaction Formula 5-2]
[0296]
[0297] In a round-bottom flask, intermediate BB (5.0 g, 0.010 mol), intermediate 1D-DB (4.3 g, 0.012 mol), tetrakis(triphenylphosphine)palladium(0) (0.24 g, 0.209 mmol), 75 ml of toluene, 10 ml of EtOH (ethanol), and 11 ml of 4M KCO (potassium carbonate) were added, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the reaction solution was filtered to obtain a crude product. The filtered crude product was separated by column chromatography using CHCl (chloroform) as the eluent to obtain 5.2 g of compound H1-D1.
[0298] 6. Synthesis of Compound H1-D2
[0299] (1) Intermediate BC
[0300] [Reaction formula 6-1]
[0301]
[0302] In the synthesis of intermediate BB, 3-bromocarbazole was replaced with intermediate CZD to obtain intermediate TBB, yielding 9.3 g of intermediate BC.
[0303] (2) Compound H1-D2
[0304] [Reaction formula 6-2]
[0305]
[0306] In the synthesis of compound H1-D1, intermediates BB and 1D-DB were replaced with intermediates BC and 1D-B, respectively, to obtain 5.1 g of compound H1-D2.
[0307] 7. Synthesis of Compound H1-D3
[0308] (1) Intermediate BD
[0309] [Reaction Formula 7-1]
[0310]
[0311] In the synthesis of intermediate BB, 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced by intermediate TD to obtain 9.5 g of intermediate BD.
[0312] (2) Compound H1-D3
[0313] [Reaction Formula 7-2]
[0314]
[0315] In the synthesis of compound H1-D2, intermediate BC was replaced with intermediate BD to obtain 5.2 g of compound H1-D3.
[0316] 8. Synthesis of Compound H1-D4
[0317] [Reaction formula 8]
[0318]
[0319] In the synthesis of compound H1-D2, intermediate 1D-B was replaced with intermediate 1D-DB to obtain 5.0 g of compound H1-D4.
[0320] 9. Synthesis of Compound H1-D5
[0321] (1) Intermediate BE
[0322] [Reaction formula 9-1]
[0323]
[0324] In the synthesis of intermediate BD, 3-bromocarbazole was replaced with intermediate CZD to obtain 9.3 g of intermediate BE.
[0325] (2) Compound H1-D5
[0326] [Reaction formula 9-2]
[0327]
[0328] In the synthesis of compound H1-D3, intermediate BD was replaced with intermediate BE to obtain 5.2 g of compound H1-D5.
[0329] 10. Synthesis of Compound H1-D6
[0330] [Reaction formula 10]
[0331]
[0332] In the synthesis of compound H1-D5, intermediate 1D-B was replaced with intermediate 1D-DB to obtain 6.5 g of compound H1-D6.
[0333] 11. Synthesis of Compound H6-D1
[0334] (1) Intermediate TDBFBr
[0335] [Reaction formula 11-1]
[0336]
[0337] In a round-bottom flask, 4,6-dibromodibenzofuran (5 g, 0.015 mol), intermediate TBB (7.3 g, 0.017 mol), tetrakis(triphenylphosphine)palladium(0) (0.33 g, 0.307 mmol), 100 ml of toluene, 10 ml of EtOH (ethanol), and 15 ml of 4M KCO (potassium carbonate) were added, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the reaction solution was filtered to obtain a crude product. The filtered crude product was recrystallized to obtain 7.2 g of intermediate TDBFBr.
[0338] (2) Compound H6-D1
[0339] [Reaction formula 11-2]
[0340]
[0341] In a round-bottom flask, the intermediate TDBFBr (7.2 g, 0.013 mol), the intermediate 1D-DB (5.3 g, 0.014 mol), tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.260 mmol), 100 ml of toluene, 10 ml of EtOH (ethanol), and 13 ml of 4M K2CO3 (potassium carbonate) were added, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the reaction solution was filtered to obtain a crude product. The filtered crude product was separated by column chromatography using CHCl3 (chloroform) as the eluent to obtain 7.8 g of compound H6-D1.
[0342] 12. Synthesis of Compound H6-D2
[0343] (1) Intermediate TDBFDBr
[0344] [Reaction formula 12-1]
[0345]
[0346] In the synthesis of intermediate TDBFBr, intermediate 4,6-dibromodibenzofuran was replaced with intermediate DBFD to obtain 7.0 g of intermediate TDBFDBr.
[0347] (2) Compound H6-D2
[0348] [Reaction formula 12-2]
[0349]
[0350] In the synthesis of compound H6-D1, the intermediate TDBFBr was replaced with the intermediate TDBFDBr to obtain 7.2 g of compound H6-D2.
[0351] 13. Synthesis of Compound H6-D3
[0352] (1) Intermediate DTDBFBr
[0353] [Reaction formula 13-1]
[0354]
[0355] In the synthesis of intermediate TDBFBr, intermediate TBB was replaced with intermediate TBDB to obtain 7.3 g of intermediate DTDBFBr.
[0356] (2) Compound H6-D3
[0357] [Reaction formula 13-2]
[0358]
[0359] In the synthesis of compound H6-D2, the intermediate TDBFDBr was replaced with the intermediate DTDBFBr to obtain 7.2 g of compound H6-D3.
[0360] 14. Synthesis of Compound H6-D4
[0361] [Reaction formula 14]
[0362]
[0363] In the synthesis of compound H6-D2, intermediate 1D-B was replaced with intermediate 1D-DB to obtain 6.9 g of compound H6-D4.
[0364] 15. Synthesis of Compound H6-D5
[0365] (1) Intermediate DTDBFDBr
[0366] [Reaction formula 15-1]
[0367]
[0368] In the synthesis of intermediate TDBFDBr, intermediate TBB was replaced with intermediate TBDB to obtain 7.0 g of intermediate DTDBFDBr.
[0369] (2) Compound H6-D5
[0370] [Reaction formula 15-2]
[0371]
[0372] In the synthesis of compound H6-D2, the intermediate TDBFDBr was replaced with the intermediate DTDBFDBr to obtain 7.1 g of compound H6-D5.
[0373] 16. Synthesis of Compound H6-D6
[0374] [Reaction formula 16]
[0375]
[0376] In the synthesis of compound H6-D5, intermediate 1D-B was replaced with intermediate 1D-DB to obtain 7.5 g of compound H6-D6.
[0377] 17. Synthesis of Compound H9-D1
[0378] [Reaction 17]
[0379]
[0380] In the synthesis of compound H1-D1, intermediate 1D-DB was replaced with intermediate 1AD-DB to obtain 5.3 g of compound H9-D1.
[0381] 18. Synthesis of Compound H9-D2
[0382] [Reaction formula 18]
[0383]
[0384] In the synthesis of compound H1-D2, intermediate 1D-B was replaced with intermediate 1AD-B to obtain 5.3 g of compound H9-D2.
[0385] 19. Synthesis of Compound H9-D3
[0386] [Reaction formula 19]
[0387]
[0388] In the synthesis of compound H1-D3, intermediate 1D-B was replaced with intermediate 1AD-B to obtain 5.2 g of compound H9-D3.
[0389] 20. Synthesis of Compound H9-D4
[0390] [Reaction formula 20]
[0391]
[0392] In the synthesis of compound H1-D4, intermediate 1D-DB was replaced with intermediate 1AD-DB to obtain 5.1 g of compound H9-D4.
[0393] 21. Synthesis of Compound H9-D5
[0394] [Reaction formula 21]
[0395]
[0396] In the synthesis of compound H1-D5, intermediate 1D-B was replaced with intermediate 1AD-B to obtain 5.2 g of compound H9-D5.
[0397] 22. Synthesis of Compound H9-D6
[0398] [Reaction formula 22]
[0399]
[0400] In the synthesis of compound H1-D6, intermediate 1D-DB was replaced with intermediate 1AD-DB to obtain 5.3 g of compound H9-D6.
[0401] 23. Synthesis of Compound H21-D1
[0402] [Reaction formula 23]
[0403]
[0404] In the synthesis of compound H1-D1, intermediate 1D-DB was replaced with intermediate 2E-DB to obtain 5.5 g of compound H21-D1.
[0405] 24. Synthesis of Compound H21-D2
[0406] [Reaction 24]
[0407]
[0408] In the synthesis of compound H1-D2, intermediate 1D-B was replaced with intermediate 2E-B to obtain 5.4 g of compound H21-D2.
[0409] 25. Synthesis of Compound H21-D3
[0410] [Reaction 25]
[0411]
[0412] In the synthesis of compound H1-D3, intermediate 1D-B was replaced with intermediate 2E-B to obtain 5.2 g of compound H21-D3.
[0413] 26. Synthesis of Compound H21-D4
[0414] [Reaction 26]
[0415]
[0416] In the synthesis of compound H1-D4, intermediate 1D-DB was replaced with intermediate 2E-DB to obtain 5.2 g of compound H21-D4.
[0417] 27. Synthesis of Compound H21-D5
[0418] [Reaction 27]
[0419]
[0420] In the synthesis of compound H1-D5, intermediate 1D-B was replaced with intermediate 2E-B to obtain 5.3 g of compound H21-D5.
[0421] 28. Synthesis of Compound H21-D6
[0422] [Reaction 28]
[0423]
[0424] In the synthesis of compound H1-D6, intermediate 1D-DB was replaced with intermediate 2E-DB to obtain 5.2 g of compound H21-D6.
[0425] 29. Synthesis of Compound H31-D1
[0426] [Reaction 29]
[0427]
[0428] In the synthesis of compound H6-D1, intermediate 1D-DB was replaced with intermediate 3D-DB to obtain 7.5 g of compound H31-D1.
[0429] 30. Synthesis of Compound H31-D2
[0430] [Reaction formula 30]
[0431]
[0432] In the synthesis of compound H6-D2, intermediate 1D-B was replaced with intermediate 3D-B to obtain 7.2 g of compound H31-D2.
[0433] 31. Synthesis of Compound H31-D3
[0434] [Reaction formula 31]
[0435]
[0436] In the synthesis of compound H6-D3, intermediate 1D-B was replaced with intermediate 3D-B to obtain 7.3 g of compound H31-D3.
[0437] 32. Synthesis of Compound H31-D4
[0438] [Reaction formula 32]
[0439]
[0440] In the synthesis of compound H6-D4, intermediate 1D-DB was replaced with intermediate 3D-DB to obtain 7.1 g of compound H31-D4.
[0441] 33. Synthesis of Compound H31-D5
[0442] [Reaction formula 33]
[0443]
[0444] In the synthesis of compound H6-D5, intermediate 1D-B was replaced with intermediate 3D-B to obtain 7.1 g of compound H31-D5.
[0445] 34. Synthesis of Compound H31-D6
[0446] [Reaction formula 34]
[0447]
[0448] In the synthesis of compound H6-D6, intermediate 1D-DB was replaced with intermediate 3D-DB to obtain 7.4 g of compound H31-D6.
[0449] The green EML 230 may further include a second compound 234 represented by Formula 3.
[0450] [Formula 3]
[0451]
[0452] In Formula 3, R11, R12, R13 and R14 are each independently selected from the group consisting of deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C10 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C10 alkylsulfoxide group, a substituted or unsubstituted C6 to C30 arylsulfoxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, C1 and C4 are each independently an integer from 0 to 4, and C2 and C3 are each independently an integer from 0 to 3. L11 and L12 are each independently selected from the group consisting of a single bond (or a direct bond), a substituted or unsubstituted C6 to C30 arylene group, and a substituted or unsubstituted C3 to C30 heteroarylene group, and Ar11 and Ar12 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group.
[0453] For example, a substituent may include a deuterium atom.
[0454] In Formula 3, L11 and L12 may be single bonds. Ar11 and Ar12 may each be independently selected from substituted or unsubstituted phenyl groups. For example, Formula 3 may be represented by Formula 3a.
[0455] [Formula 3a]
[0456]
[0457] In Formula 3a, R11, R12, R13, R14, c1, c2, c3, and c4 may be defined the same as in Formula 3. R13 and R14 may each be independently selected from a substituted or unsubstituted C6 to C30 aryl group. C5 and C6 may each independently be an integer from 0 to 5.
[0458] For example, in Formula 3a, R13 and R14 can each be independently selected from phenyl and biphenyl. C5 and C6 can each be independently 0 or 1.
[0459] The second compound 234 may be one of the compounds in Formula 4.
[0460] [Formula 4]
[0461]
[0462]
[0463]
[0464]
[0465]
[0466] The green EML 230 may further include a third compound 236 represented by Formula 5.
[0467] [Formula 5]
[0468]
[0469] In Formula 5, R21, R22, R23, and R24 may each be independently selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group. d1, d2, d3, and d4 may each independently be an integer from 0 to 4, and n may be an integer from 1 to 3.
[0470] The third compound 236 may be one of the compounds in Formula 6.
[0471] [Formula 6]
[0472]
[0473] In the green EML 230, the first compound 232 may be an n-type host (eg, a first host). The second compound 234 may be a p-type host (eg, a second host). The third compound 236 may be an illuminant (eg, a dopant). The green EML 230 may have The thickness, for example,
[0474] In the green EML 230, the weight percentage of the first compound 232 and the second compound 234 may be greater than the weight percentage of the third compound 236. The weight percentage of the first compound 232 and the weight percentage of the second compound 234 may be the same or different. In the green EML 230, the weight percentage ratio of the first compound 232 to the second compound 234 may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight percentage of the first compound 232 and the weight percentage of the second compound 234 may be the same. For example, the first compound 232 and the second compound 234 may be present in the same weight percentage. The third compound 236 may be present in the green EML 230 in an amount of 5 to 25 weight percent based on the total weight of the components in the green EML 230.
[0475] The organic light emitting layer 162 may further include an ETL 240 between the green EML 230 and the second electrode 164. For example, the ETL 240 may contact the green EML 230. The thickness of the ETL 240 may be substantially the same as that of the green EML 230. For example, the ETL 240 may have a thickness of The thickness, for example,
[0476] The ETL 240 may include a compound represented by Formula 7 (eg, an electron transport material).
[0477] [Formula 7]
[0478]
[0479] In Formula 7, L31 may be selected from the group consisting of a single bond, a substituted or unsubstituted C6 to C30 arylene group, and a substituted or unsubstituted C3 to C30 heteroarylene group. Ar31 may be represented by Formula 7a or Formula 7b. Ar32 and Ar33 may each independently be selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C10 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C10 alkyl sulfoxide group, a substituted or unsubstituted C6 to C30 aryl sulfoxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group.
[0480] [Formula 7a]
[0481]
[0482] [Formula 7b]
[0483]
[0484] In Formula 7a, R31 may be selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C10 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C10 alkylsulfoxide group, a substituted or unsubstituted C6 to C30 arylsulfoxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group. R32 may be selected from the group consisting of deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C10 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C10 alkylsulfoxide group, a substituted or unsubstituted C6 to C30 arylsulfoxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, and e1 may be an integer from 0 to 4. In Formula 7a and Formula 7b, the wavy mark is a bonding (connection) site to L31 in Formula 7.
[0485] In Formula 7b, R33 may be selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C10 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C10 alkylsulfoxide group, a substituted or unsubstituted C6 to C30 arylsulfoxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group. R34 may be selected from the group consisting of deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C10 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C1 to C10 alkylsulfoxide group, a substituted or unsubstituted C6 to C30 arylsulfoxide group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, and e2 may be an integer from 0 to 4.
[0486] For example, Formula 7 can be expressed by Formula 7c.
[0487] [Formula 7c]
[0488]
[0489] In Formula 7c, L31, Ar31, Ar32 and Ar33 are defined the same as in Formula 7.
[0490] Alternatively, Formula 7 may be represented by Formula 7d. However, embodiments of the present disclosure are not limited to these examples.
[0491] [Formula 7d]
[0492]
[0493] In Formula 7d, L31, Ar31, Ar32 and Ar33 are defined the same as in Formula 7.
[0494] For example, the electron transport material in the ETL 240 may be one of the compounds in Formula 8.
[0495] [Formula 8]
[0496]
[0497]
[0498]
[0499]
[0500] The organic light emitting layer 162 may further include an HTL 220 between the first electrode 160 and the green EML 230. The thickness of the HTL 220 may be greater than the thickness of each of the green EML 230 and the ETL 240. For example, the HTL may have The thickness, for example,
[0501] In addition, the organic light emitting layer 162 may further include at least one of a HIL 210 located between the first electrode 160 and the HTL 220 , and an EIL 250 located between the second electrode 164 and the ETL 240 .
[0502] Although not shown, the organic light emitting layer 162 may further include at least one of an EBL positioned between the HTL 220 and the green EML 230 and an HBL positioned between the EML 230 and the ETL 240 .
[0503] The HIL 210 may include at least one compound selected from the group consisting of: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalen-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalen-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazol-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis( 1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPB or NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine. The HIL 210 may have The thickness, for example,
[0504] The HTL 220 may include at least one compound selected from the group consisting of: N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (or NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-bis(4-tert-butyl)-N,N'-bis(phenyl)-biphenyl diamine] (poly-TPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-( 4-secondary butylphenyl) diphenylamine))] (TFB), bis-[4-(N,N'-di-p-tolylamino) phenyl] cyclohexane (TAPC), 3,5-bis(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine. Alternatively, the HTL 220 may include a compound of Formula 10 below. However, embodiments of the present disclosure are not limited to these examples.
[0505] The EIL 250 may include at least one of an alkali metal such as Li, an alkali metal halide compound such as LiF, CsF, NaF, or BaF2, and an organometallic compound such as Liq, lithium benzoate, or sodium stearate. The thickness, for example,
[0506] The EBL may include at least one compound selected from the group consisting of tris(4-carbazol-9-yl-phenyl)amine (TCTA), tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, di-[4-(N,N'-di-p-tolylamino)phenyl]cyclohexane (TAPC), 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 1,3-bis(carbazol-9-yl)benzene (m CP), 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), copper phthalocyanine (CuPc), N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), 3,5-bis(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), and 2,8-bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene.
[0507] The HBL may include at least one compound selected from the group consisting of: 2,9-dimethyl-4,7-diphenyl-1,10-phenaloline (BCP), bis(2-methyl-8-quinolinolato-N1,08)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), tris-(8-hydroxyquinolinolato)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, Liq, bis-4,6-(3,5-di-3-pyridylphenyl)-2-methylpyrimidine (B3PYMPM), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 9-(6-9H-carbazol-9-yl)pyridin-3-yl)-9H-3,9'-biscarbazole, and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1).
[0508] As shown above, in a green pixel in an OLED, the green EML 230 may include a first compound 232, which may be an example of an organic compound of the present disclosure and represented by Formula 1. Therefore, in the OLED D, driving voltage may be reduced, and luminous efficiency and luminous lifetime may be improved.
[0509] When the first compound 232 in which the fused fluorene moiety in Formula 1 is deuterated is included in the green EML 230 , the OLED D can provide a sufficient increase in luminescence lifetime while minimizing an increase in production cost.
[0510] In addition, the green EML 230 may further include the second compound 234 represented by Formula 3 as a second host while having the first compound 232 as the first host, so that the OLED D may have further advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0511] The green EML 230 may further include a third compound 236 represented by Formula 5 as a light emitting body while having the first compound 232 as a first host and the second compound 234 as a second host, so that the OLED D may have more desirable advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0512] In addition, the OLED in the green pixel may further include an ETL 240 between the green EML 230 and the second electrode 164 as a cathode, which may include an electron transport material represented by Formula 7, so that the OLED D can have further advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0513] [OLED]
[0514] Sequentially deposit the anode (ITO), the HIL (e.g., the compound in Formula 9, ), HTL (e.g., the compound in Formula 10, ), a green EML (eg, a first host, a second host, and a dopant (compound GD1 in Formula 6, 15 wt%), ), ETL EIL (e.g., LiF, ) and cathode (e.g., Al, ) to form an OLED.
[0515] [Formula 9]
[0516]
[0517] [Equation 10]
[0518] 1. Comparative Example
[0519] (1) Comparative Example 1 (Ref 1)
[0520] A green EML was formed using the compound TPBi in Formula 11 as a first host and the compound BCz-1 in Formula 4 as a second host (weight ratio of (first host):(second host)=1:1). An ETL was formed using the compound ZADN2 in Formula 8.
[0521] (2) Comparative Example 2 (Ref2)
[0522] Compound TPBi in Formula 11 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio=1:1) Compound ET2 in Formula 8 was used to form an ETL.
[0523] (3) Comparative Example 3 (Ref3)
[0524] Compound H1 in Formula 12 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0525] (4) Comparative Example 4 (Ref4)
[0526] Compound H6 in Formula 12 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0527] (5) Comparative Example 5 (Ref5)
[0528] Compound H9 in Formula 12 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0529] (6) Comparative Example 6 (Ref6)
[0530] Compound H21 in Formula 12 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0531] (7) Comparative Example 7 (Ref7)
[0532] Compound H31 in Formula 12 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0533] (8) Comparative Examples 8 to 12 (Ref8 to Ref12)
[0534] Ref8 to Ref12 are similar to Ref3 to Ref7, respectively, except that ET2 of Formula 8 is used in Ref8 to Ref12 instead of the compound ZADN2 of Formula 8 used in Ref3 to Ref7.
[0535] [Equation 11]
[0536]
[0537] [Equation 12]
[0538]
[0539]
[0540] 2. Examples
[0541] (1) Example 1 (Ex1)
[0542] Compound H1-D1 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0543] (2) Example 2 (Ex2)
[0544] Compound H1-D2 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0545] (3) Example 3 (Ex3)
[0546] Compound H1-D3 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0547] (4) Example 4 (Ex4)
[0548] Compound H1-D4 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0549] (5) Example 5 (Ex5)
[0550] Compound H1-D5 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0551] (6) Example 6 (Ex6)
[0552] Compound H1-D6 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0553] (7) Examples 7 to 12 (Ex7 to Ex12)
[0554] Ex7 to Ex12 are similar to Ex1 to Ex6, respectively, except that the compound ET2 of Formula 8 is used instead of the compound ZADN2 of Formula 8 used in Ex1 to Ex6.
[0555] (8) Example 13 (Ex13)
[0556] Compound H6-D1 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0557] (9) Example 14 (Ex14)
[0558] Compound H6-D2 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0559] (10) Example 15 (Ex15)
[0560] Compound H6-D3 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0561] (11) Example 16 (Ex16)
[0562] Compound H6-D4 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0563] (12) Example 17 (Ex17)
[0564] Compound H6-D5 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0565] (13) Example 18 (Ex18)
[0566] Compound H6-D6 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0567] (14) Examples 19 to 24 (Ex19 to Ex24)
[0568] Ex19 to Ex24 are similar to Ex13 to Ex18, respectively, except that compound ET2 of Formula 8 is used in Ex19 to Ex24 instead of compound ZADN2 of Formula 8 used in Ex13 to Ex18.
[0569] (15) Example 25 (Ex25)
[0570] Compound H9-D1 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0571] (16) Example 26 (Ex26)
[0572] Compound H9-D2 in Formula 2 was used as the first host and compound BCz-1 in Formula 4 was used as the second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0573] (17) Example 27 (Ex27)
[0574] Compound H9-D3 in Formula 2 was used as the first host and compound BCz-1 in Formula 4 was used as the second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0575] (18) Example 28 (Ex28)
[0576] Compound H9-D4 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0577] (19) Example 29 (Ex29)
[0578] Compound H9-D5 in Formula 2 was used as the first host and compound BCz-1 in Formula 4 was used as the second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0579] (20) Example 30 (Ex30)
[0580] Compound H9-D6 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0581] (21) Examples 31 to 36 (Ex31 to Ex36)
[0582] Ex31 to Ex36 are similar to Ex25 to Ex30, respectively, except that compound ET2 of Formula 8 is used in Ex31 to Ex36 instead of compound ZADN2 of Formula 8 used in Ex25 to Ex30.
[0583] (22) Example 37 (Ex37)
[0584] Compound H21-D1 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0585] (23) Example 38 (Ex38)
[0586] Compound H21-D2 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0587] (24) Example 39 (Ex39)
[0588] Compound H21-D3 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0589] (25) Example 40 (Ex40)
[0590] Compound H21-D4 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1). Compound ZADN2 in Formula 8 was used to form an ETL.
[0591] (26) Example 41 (Ex41)
[0592] Compound H21-D5 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0593] (27) Example 42 (Ex42)
[0594] Compound H21-D6 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1). Compound ZADN2 in Formula 8 was used to form an ETL.
[0595] (28) Examples 43 to 48 (Ex43 to Ex48)
[0596] Ex43 to Ex48 are similar to Ex37 to Ex42, respectively, except that compound ET2 of Formula 8 is used in Ex43 to Ex48 instead of compound ZADN2 of Formula 8 used in Ex37 to Ex42.
[0597] (29) Example 49 (Ex49)
[0598] Compound H31-D1 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0599] (30) Example 50 (Ex50)
[0600] Compound H31-D2 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0601] (31) Example 51 (Ex51)
[0602] Compound H31-D3 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0603] (32) Example 52 (Ex52)
[0604] Compound H31-D4 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0605] (33) Example 53 (Ex53)
[0606] Compound H31-D5 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML (weight ratio of (first host):(second host)=1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0607] (34) Example 54 (Ex54)
[0608] Compound H31-D6 in Formula 2 was used as a first host and compound BCz-1 in Formula 4 was used as a second host to form a green EML. ((first host):(second host) weight ratio = 1:1) Compound ZADN2 in Formula 8 was used to form an ETL.
[0609] (35) Examples 55 to 60 (Ex55 to Ex60)
[0610] Ex55 to Ex60 are similar to Ex49 to Ex54, respectively, except that compound ET2 of Formula 8 is used in Ex55 to Ex60 instead of compound ZADN2 of Formula 8 used in Ex49 to Ex54.
[0611] The characteristics of the OLEDs in Comparative Examples 1 to 12 and Examples 1 to 60, such as driving voltage (ΔV), luminous efficiency, and lifespan (T95), were measured and are listed in Tables 1 to 6.
[0612] Table 1
[0613]
[0614] Table 2
[0615]
[0616] Table 3
[0617]
[0618] Table 4
[0619]
[0620] Table 5
[0621]
[0622] Table 6
[0623]
[0624] As shown in Tables 1 to 6, the OLEDs in Ex1 to Ex60 of the examples in which the green EML included the organic compound of the present disclosure exhibited excellent driving voltage, luminous efficiency, and lifespan compared to the OLEDs in Ref1 to Ref12.
[0625] As shown in Examples 1, 4, 6, 7, 10, 12, 13, 16, 18, 19, 22, 24, 25, 28, 30, 31, 34, 36, 37, 40, 42, 43, 46, 48, 49, 52, 54, 55, 58 and 60, when an organic compound in which the fused fluorene moiety in Formula 1 is deuterated is included in the green EML, the lifespan of the OLED is significantly increased.
[0626] On the other hand, the OLEDs in Examples 1, 4, 7, 10, 13, 16, 19, 22, 25, 28, 31, 34, 37, 40, 43, 46, 49, 52, 55, and 58, in which the first host (e.g., an example of the organic compound of the present disclosure) included in the green EML was partially deuterated, had slightly shorter lifetimes than the OLEDs in Examples 6, 12, 18, 24, 30, 36, 42, 48, 54, and 60, in which the first host (e.g., an example of the organic compound of the present disclosure) included in the green EML was fully deuterated. However, in the OLEDs in Examples 1, 4, 7, 10, 13, 16, 19, 22, 25, 28, 31, 34, 37, 40, 43, 46, 49, 52, 55, and 58, the use of relatively inexpensive deuterium atoms provided sufficient lifetime.
[0627] Figure 4 A schematic cross-sectional view of an OLED according to a third embodiment of the present disclosure is shown.
[0628] like Figure 4 As shown, the OLED D may include a first electrode 160 and a second electrode 164 that may face each other, and an organic light-emitting layer 162 therebetween. The organic light-emitting layer 162 may include a first light-emitting portion 310 including a first green EML 320 and a second light-emitting portion 330 including a second green EML 340. The organic light-emitting layer 162 may further include a CGL 350 between the first light-emitting portion 310 and the second light-emitting portion 330.
[0629] The first electrode 160 may serve as an anode for injecting holes and may be formed of a conductive material having a relatively high work function (e.g., ITO or IZO). The second electrode 164 may serve as a cathode for injecting electrons and may be formed of a conductive material having a relatively low work function (e.g., Al, Mg, or AlMg).
[0630] In a top-emission OLED D, the first electrode 160 may further include a reflective layer serving as a reflective electrode. The second electrode 164 may have a thin profile to serve as a transparent (semi-transparent) electrode. Alternatively, in a bottom-emission OLED D, the first electrode 160 may serve as a transparent electrode. The second electrode 164 may serve as a reflective electrode. However, embodiments of the present disclosure are not limited to these examples.
[0631] The CGL 350 may be located between the first light emitting portion 310 and the second light emitting portion 330. The first light emitting portion 310, the CGL 350, and the second light emitting portion 330 may be sequentially stacked on the first electrode 160. For example, the first light emitting portion 310 may be located between the first electrode 160 and the CGL 350. The second light emitting portion 330 may be located between the second electrode 164 and the CGL 350.
[0632] The first light emitting portion 310 may further include a first ETL 316 between the first green EML 320 and the CGL 350. For example, the first ETL 316 may be located between the first green EML 320 and the CGL 350.
[0633] In addition, the first light emitting portion 310 may further include at least one of a HIL 312 between the first green EML 320 and the first electrode 160 and a HTL 314 between the first green EML 320 and the HIL 312 .
[0634] In addition, the first light emitting portion 310 may further include at least one of a first EBL (not shown) between the first green EML 320 and the first HTL 314 and a first HBL (not shown) between the first green EML 320 and the first ETL 316 .
[0635] The second light emitting portion 330 may further include a second ETL 334 between the second green EML 340 and the second electrode 164 .
[0636] In addition, the second light emitting portion 330 may further include at least one of a second HTL 332 under the second green EML 340 and an EIL 336 between the second ETL 334 and the second electrode 164 .
[0637] In addition, the second light emitting portion 330 may further include at least one of a second EBL (not shown) between the second green EML 340 and the second HTL 332 and a second HBL (not shown) between the second green EML 340 and the second ETL 334 .
[0638] The CGL 350 may be located between the first light emitting portion 310 and the second light emitting portion 330. For example, the first light emitting portion 310 and the second light emitting portion 330 may be connected through the CGL 350. The CGL 350 may be a PN junction CGL including an N-type CGL 352 and a P-type CGL 354.
[0639] The N-type CGL 352 may be located between the first ETL 316 and the second HTL 332. The P-type CGL 354 may be located between the N-type CGL 352 and the second HTL 332.
[0640] The first green EML 320 may include a first compound 322 , a second compound 324 , and a third compound 326 . The second green EML 340 may include a fourth compound 342 , a fifth compound 344 , and a sixth compound 346 .
[0641] At least one of the first compound 322 and the fourth compound 342 is an example of an organic compound of the present disclosure represented by Formula 1, and at least one of the second compound 324 and the fifth compound 344 is a compound represented by Formula 3. In addition, at least one of the third compound 326 and the sixth compound 346 is a compound represented by Formula 5.
[0642] For example, at least one of the first green EML 320 and the second green EML 340 may include examples of the compound represented by Formula 1, the compound represented by Formula 3, and the compound represented by Formula 5.
[0643] In the first green EML 320, the first compound 322 may serve as an n-type host, for example, a first host, the second compound 324 may serve as a p-type host, for example, a second host, and the third compound 326 may serve as an emitter, for example, a dopant. In the second green EML 340, the fourth compound 342 may serve as an n-type host, for example, a first host, the fifth compound 344 may serve as a p-type host, for example, a second host, and the sixth compound 34 may serve as an emitter, for example, a dopant. Each of the first green EML 320 and the second green EML 340 may have thickness.
[0644] When the first compound 322 and the fourth compound 342 are examples of organic compounds represented by Formula 1, the first compound 322 and the fourth compound 342 may be the same or different. When the second compound 324 and the fifth compound 344 are examples of organic compounds represented by Formula 3, the second compound 324 and the fifth compound 344 may be the same or different. When the third compound 326 and the sixth compound 346 are examples of organic compounds represented by Formula 5, the third compound 326 and the sixth compound 346 may be the same or different.
[0645] In the first green EML 320, the weight percentage of each of the first compound 322 and the second compound 324 may be greater than the weight percentage of the third compound 326. The weight percentage of the first compound 322 and the weight percentage of the second compound 324 may be the same or different. In the first green EML 320, the weight percentage ratio of the first compound 322 to the second compound 324 may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight percentage of the first compound 322 and the weight percentage of the second compound 324 may be the same. For example, the first compound 322 and the second compound 324 may be present in the same weight percentage. The third compound 326 may be present in the first green EML 320 in an amount of 5 to 25 weight percent based on the total weight of the components in the first green EML 320.
[0646] In the second green EML 340, the weight percentage of each of the fourth compound 342 and the fifth compound 344 may be greater than the weight percentage of the sixth compound 346. The weight percentage of the fourth compound 342 and the weight percentage of the fifth compound 344 may be the same or different. In the second green EML 340, the weight percentage ratio of the fourth compound 342 to the fifth compound 344 may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight percentage of the fourth compound 342 and the weight percentage of the fifth compound 344 may be the same. For example, the fourth compound 342 and the fifth compound 344 may be present in the same weight percentage. Based on the total weight of the components in the second green EML 340, the sixth compound 346 may be present in the second green EML 340 in an amount of 5 weight % to 25 weight %.
[0647] Each of the first ETL 316 and the second ETL 334 may include an example of a compound represented by Formula 7 (eg, an electron transport material).
[0648] In the OLED D in the green pixel, at least one of the first green EML 320 and the second green EML 340 may include the example of the organic compound of the present disclosure represented by Formula 1. Therefore, in the OLED D, driving voltage may be reduced, and luminous efficiency and lifespan may be improved.
[0649] When the organic compound in which the fused fluorene moiety in Formula 1 is deuterated is included in at least one of the first green EML 320 and the second green EML 340 , the OLED D may provide a sufficient increase in luminescence lifetime while minimizing an increase in production cost.
[0650] In addition, at least one of the first green EML 320 and the second green EML 340 may further include an example of the compound represented by Formula 3 as a second host when the first host is an example of the organic compound of the present disclosure, so that the OLED D can have advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0651] In addition, at least one of the first green EML 320 and the second green EML 340 may further include an example of a compound represented by Formula 5 as a light emitting body while having a first host represented by Formula 1 and a second host represented by Formula 3, so that the OLED D can have further advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0652] Furthermore, in the OLED D in the green pixel, at least one of the first ETL 316 and the second ETL 334 may include an example of the electron transport material represented by Formula 7, so that the OLED D may have further advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0653] Figure 5 A schematic cross-sectional view illustrating an organic light emitting display device according to a fourth embodiment of the present disclosure is shown. Figure 6 A schematic cross-sectional view of an OLED according to a fifth embodiment of the present disclosure is shown. Figure 7 A schematic cross-sectional view of an OLED according to a sixth embodiment of the present disclosure is shown.
[0654] like Figure 5 As shown, the organic light-emitting display device 400 may include: a first substrate 410, in which red pixels RP, green pixels GP, and blue pixels BP may be defined; a second substrate 470 facing the first substrate 410; an OLED D, which may be located between the first substrate 410 and the second substrate 470 and provide white light emission; and a color filter layer 480, which is located between the OLED D and the second substrate 470.
[0655] Each of the first substrate 410 and the second substrate 470 may be a glass substrate or a flexible substrate. For example, each of the first substrate 410 and the second substrate 470 may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.
[0656] The buffer layer 420 may be formed on the substrate. The TFT Tr corresponding to each of the red pixel RP, the green pixel GP, and the blue pixel BP may be formed on the buffer layer 420. The buffer layer 420 may be omitted.
[0657] The semiconductor layer 422 may be formed on the buffer layer 420. The semiconductor layer 422 may include an oxide semiconductor material or polysilicon.
[0658] A gate insulating layer 424 may be formed on the semiconductor layer 422. The gate insulating layer 424 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.
[0659] The gate electrode 430 , which may be formed of a conductive material such as metal, may be formed on the gate insulating layer 424 to correspond to the center of the semiconductor layer 422 .
[0660] An interlayer insulating layer 432, which may be formed of an insulating material, may be formed on the gate electrode 430. The interlayer insulating layer 432 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo acryl.
[0661] The interlayer insulating layer 432 may include a first contact hole 434 and a second contact hole 436 that expose both sides of the semiconductor layer 422. The first contact hole 434 and the second contact hole 436 may not cover a portion of the surface of the semiconductor layer 422 closer to opposite ends than the center of the semiconductor layer 422. The first contact hole 434 and the second contact hole 436 may be located on both sides of the gate electrode 430 to be spaced apart from the gate electrode 430.
[0662] A source electrode 440 and a drain electrode 442 , which may be formed of a conductive material such as metal, may be formed on the interlayer insulating layer 432 .
[0663] The source electrode 440 and the drain electrode 442 may be spaced apart from each other with respect to the gate electrode 430 and contact both sides of the semiconductor layer 422 through the first contact hole 434 and the second contact hole 436 , respectively.
[0664] The semiconductor layer 422, the gate electrode 430, the source electrode 440, and the drain electrode 442 may constitute a TFT Tr. The TFT Tr may be used as a driving element. For example, the TFT Tr may correspond to a driving TFT Td ( Figure 1 ).
[0665] Although not shown, the gate lines and the data lines may cross each other to define pixels. The switching TFT may be formed to be connected to the gate lines and the data lines. The switching TFT may be connected to the TFT Tr as a driving element.
[0666] In addition, a power line and a storage capacitor for maintaining a voltage of a gate electrode of the TFT Tr in one frame may be further formed. The power line may be formed parallel to and spaced apart from one of the gate line and the data line.
[0667] The planarization layer 450 may be formed to cover the TFT Tr, and the planarization layer 450 may include a drain contact hole 452 exposing the drain electrode 442 of the TFT Tr. The drain contact hole 452 may not cover the drain electrode 442.
[0668] A first electrode 460 may be formed in each pixel and on the planarization layer 450, respectively, and the first electrode 460 may be connected to the drain electrode 442 of the TFT Tr via the drain contact hole 452. The first electrode 460 may be an anode and may be formed of a conductive material having a relatively high work function, such as a transparent conductive oxide (TCO). The first electrode 460 may further include a reflective electrode or a reflective layer. For example, the reflective electrode or the reflective layer may be formed of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In the top-emission organic light-emitting display device 400, the first electrode 460 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.
[0669] A bank layer 466 may be formed on the planarization layer 450 to cover the edge of the first electrode 460. For example, the bank layer 466 may be located at the boundary of the pixel and may expose the center of the first electrode 460 in the pixel. The bank layer 466 may not cover the center of the first electrode 460 in the pixel. Since the OLED D can emit white light in the red pixel RP, the green pixel GP, and the blue pixel BP, the organic light-emitting layer 462 may be formed as a common layer in the red pixel RP, the green pixel GP, and the blue pixel BP without separation. The bank layer 466 may be formed to prevent current leakage at the edge of the first electrode 460 and may be omitted.
[0670] An organic light emitting layer 462 may be formed on the first electrode 460 .
[0671] like Figure 5 As shown, the second electrode 464 may be formed over the substrate 410 where the organic light emitting layer 462 may be formed.
[0672] In the organic light-emitting display device 400 , since light emitted from the organic light-emitting layer 462 may be incident on the color filter layer 480 through the second electrode 464 , the second electrode 464 may have a thin profile for transmitting light.
[0673] The first electrode 460 , the organic light emitting layer 462 , and the second electrode 464 may constitute an OLED D.
[0674] The color filter layer 480 may be located above the OLED D and may include a red color filter 482, a green color filter 484, and a blue color filter 486 corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. The red color filter 482 may include at least one of a red dye and a red pigment. The green color filter 484 may include at least one of a green dye and a green pigment. The blue color filter 486 may include at least one of a blue dye and a blue pigment.
[0675] Although not shown, the color filter layer 480 may be attached to the OLED D through an adhesive layer. Alternatively, the color filter layer 480 may be directly formed on the OLED D. However, embodiments of the present disclosure are not limited to these examples.
[0676] An encapsulation film (not shown) may be formed to prevent moisture from penetrating into the OLED D. For example, the encapsulation film may include a first inorganic insulating layer, an organic insulating layer, and a second inorganic insulating layer sequentially stacked, but is not limited thereto. The encapsulation film may be omitted.
[0677] A polarizing plate (not shown) for reducing ambient light reflection may be disposed above the top emission type OLED D. For example, the polarizing plate may be a circular polarizing plate.
[0678] exist Figure 5 In the OLED D, the first electrode 460 and the second electrode 464 may be a reflective electrode and a transparent (or semi-transparent) electrode, respectively. A color filter layer 480 may be provided above the OLED D. Alternatively, when the first electrode 460 and the second electrode 464 are a transparent (or semi-transparent) electrode and a reflective electrode, respectively, the color filter layer 480 may be provided between the OLED D and the first substrate 410. However, embodiments of the present disclosure are not limited to these examples.
[0679] A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 480. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. White light emitted from the OLED D may be converted into red light, green light, and blue light by the red conversion layer, the green conversion layer, and the blue conversion layer, respectively. For example, the color conversion layer may include quantum dots. Thus, the color purity of the organic light-emitting display device 400 may be further improved.
[0680] A color conversion layer may be included instead of the color filter layer 480 .
[0681] As described above, in the organic light-emitting display device 400, the OLED D in the red pixel RP, the green pixel GP, and the blue pixel BP can emit white light. The white light from the organic light-emitting diode D can pass through the red color filter 482, the green color filter 484, and the blue color filter 486. As a result, red light, green light, and blue light can be provided from the red pixel RP, the green pixel GP, and the blue pixel BP, respectively.
[0682] exist Figure 5 In the example of an OLED D that emits white light, it can be used in a display device. Alternatively, the OLED D can be formed on the entire surface of a substrate without at least one of a driving element or a color filter layer used in an illumination device. A display device and an illumination device each including an OLED D of the present disclosure can be referred to as an organic light-emitting device. However, embodiments of the present disclosure are not limited to these examples.
[0683] like Figure 6 As shown, the organic light-emitting layer 462 may include a first light-emitting portion 530 including a green EML 510, a second light-emitting portion 540 including a first blue EML 550, and a third light-emitting portion 560 including a second blue EML 570. In addition, the organic light-emitting layer 462 may further include a first CGL 580 located between the first light-emitting portion 530 and the second light-emitting portion 540, and a second CGL 590 located between the first light-emitting portion 530 and the third light-emitting portion 560. In addition, the first light-emitting portion 530 may further include a red EML 520.
[0684] The second light-emitting portion 540 may be located between the first electrode 460 and the first light-emitting portion 530. The third light-emitting portion 560 may be located between the first light-emitting portion 530 and the second electrode 464. The second light-emitting portion 540 may be located between the first electrode 460 and the first CGL 580. The third light-emitting portion 560 may be located between the second CGL 590 and the second electrode 464. For example, the second light-emitting portion 540, the first CGL 580, the first light-emitting portion 530, the second CGL 590, and the third light-emitting portion 560 may be sequentially stacked on the first electrode 460.
[0685] In the first light emitting portion 530 , the red EML 520 may be disposed under the green EML 510 .
[0686] The first light emitting portion 530 may further include a first ETL 534 disposed on the green EML 510. In addition, the first light emitting portion 530 may further include a first HTL 532 disposed under the red EML 520.
[0687] For example, in the first light emitting portion 530, the red EML 520 may be located between the first HTL 532 and the green EML 510. The green EML 510 may be located between the red EML 520 and the first ETL 534.
[0688] The second light emitting portion 540 may further include at least one of a second HTL 544 disposed under the first blue EML 550 and a second ETL 546 disposed on the first blue EML 550. In addition, the second light emitting portion 540 may further include a HIL 542 between the first electrode 460 and the second HTL 544.
[0689] In addition, the second light emitting portion 540 may further include a first EBL (not shown) between the second HTL 544 and the first blue EML 550 , and a first HBL (not shown) between the second ETL 546 and the first blue EML 550 .
[0690] The third light emitting portion 560 may further include at least one of a third HTL 562 disposed under the second blue EML 570 and a third ETL 564 disposed on the second blue EML 570. In addition, the third light emitting portion 560 may further include an EIL 566 between the second electrode 464 and the third ETL 564.
[0691] In addition, the third light emitting portion 560 may further include a second EBL (not shown) between the third HTL 562 and the second blue EML 570 , and a second HBL (not shown) between the third ETL 564 and the second blue EML 570 .
[0692] The green EML 510 may include a first compound 512, which may be an example of an organic compound of the present disclosure represented by Formula 1. In addition, the green EML 510 may further include a second compound 514, which may be an example of a compound represented by Formula 3. In addition, the green EML 510 may further include a third compound 516, which may be an example of a compound represented by Formula 5.
[0693] In the green EML 510, the first compound 512 may be an n-type host (eg, a first host), the second compound 514 may be a p-type host (eg, a second host), and the third compound 516 may be an emitting body (eg, a dopant). The green EML 510 may have thickness.
[0694] In green EML 510, the weight percentage of each of first compound 512 and second compound 514 may be greater than the weight percentage of third compound 516. The weight percentage of first compound 512 and the weight percentage of second compound 514 may be the same or different. In green EML 510, the weight percentage ratio of first compound 512 to second compound 514 may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight percentage of first compound 512 and the weight percentage of second compound 514 may be the same. For example, first compound 512 and second compound 514 may be present in the same weight percentage. Third compound 516 may be present in green EML 510 in an amount of 5 to 25 weight percent based on the total weight of the components in green EML 510.
[0695] Each of the first to third ETLs 534 , 546 , and 564 may include an example of the compound represented by Formula 7 as an electron transport material.
[0696] The red EML 520 may include a red host and a red dopant. The red dopant may include at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. In the red EML 520, the red host may be present in a greater weight percentage than the red dopant. In the red EML 520, the red dopant may be present in an amount of 1 to 10 weight percent, or 1 to 5 weight percent, based on the total weight of the components in the red EML 520.
[0697] For example, the red host may be at least one selected from the group consisting of 9,9'-diphenyl-9H,9'H-3,3'-dicarbazole (BCzPh), CBP, 1,3,5-tris(carbazol-9-yl)benzene (TCP), TCTA, 4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl (CDBP), 2,7-bis(carbazol-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(carbazol-9-yl)-9,9-spirofluorene (Spiro-CB P), DPEPO, 4'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (PCzB-2CN), 3'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (mCzB-2CN), 3,6-bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCzl), bis(2-hydroxyphenyl)-pyridine)beryllium (Bepp2), bis(10-hydroxybenzo[h]quinoline)beryllium (Bebq2), and 1,3,5-tri(1-pyrene)benzene (TPB3), but are not limited thereto.
[0698] The red dopant may be at least one selected from the group consisting of bis(2-(4,6-dimethyl)phenylquinolinate)](2,2,6,6-tetramethylheptane-3,5-dioate)iridium(III), bis[2-(4-n-hexylphenyl)quinolinate](acetylacetonate)iridium(III) (Hex-Ir(phq)2(acac)), tris[2-(4-n-hexylphenyl)quinolinate]iridium(III) (Hex-Ir(phq)3), tris[2-phenyl-4-methylquinolinate]iridium(III) (Ir(Mphq)3), bis(2-phenylquinolinate)(2,2,6,6-tetramethylheptane-3,5-dioate)iridium(III) (Ir(dpm)PQ2), bis(phenylisoquinolinate)(2,2,6,6-tetramethylheptane-3,5-dioate)iridium(III) (Ir(dpm)PQ2), olefin-3,5-dicarboxylate)iridium(III) (Ir(dpm)(piq)2), bis[(4-n-hexylphenyl)isoquinolinato](acetylacetonate)iridium(III) (Hex-Ir(piq)2(acac)), tris[2-(4-n-hexylphenyl)quinolinato]iridium(III) (Hex-Ir(piq)3), tris(2-(3-methylphenyl)-7-methyl-quinolinato)iridium (Ir(dmpq)3), bis[2-(2-methylphenyl)-7-methyl-quinolinato](acetylacetonate)iridium(III) (Ir(dmpq)2(acac)), and bis[2-(3,5-dimethylphenyl)-4-methyl-quinolinato](acetylacetonate)iridium(III) (Ir(mphmq)2(acac)), but are not limited thereto.
[0699] The first blue EML 550 in the second light emitting portion 540 may include a first blue host and a first blue dopant. The second blue EML 570 in the third light emitting portion 560 may include a second blue host and a second blue dopant.
[0700] Each of the first and second blue dopants may include at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In the first blue EML 550, the first blue host may be present in a greater weight percent than the first blue dopant. In the second blue EML 570, the second blue host may be present in a greater weight percent than the second blue dopant. In each of the first and second blue EMLs 550 and 570, the first and second blue dopants may be present in an amount of 1 to 10 weight percent, or 1 to 5 weight percent, based on the total weight of the components in each of the first and second blue EMLs 550 and 570.
[0701] For example, each of the first blue host and the second blue host can independently be at least one selected from the group consisting of: mCP, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-carbazole-3-carbonitrile (mCP-CN), mCBP, CBP-CN, 9-(3-(9H-carbazole-9-yl)phenyl)-3-(diphenylphosphoryl)-9H-carbazole (mCPPO1), 3,5-di(9H-carbazole-9-yl)biphenyl (Ph-mCP), TSPO1, 9-(3'-(9H-carbazole)phenyl)-3-(diphenylphosphoryl)-9H-carbazole (mCPPO1), -9-yl)-[1,1'-biphenyl]-3-yl)-9H-pyridyl[2,3-b]indole (CzBPCb), bis(2-methylphenyl)diphenylsilane (UGH-1), 1,4-bis(triphenylsilyl)benzene (UGH-2), 1,3-bis(triphenylsilyl)benzene (UGH-3), 9,9-spirobisfluoro-2-yl-diphenyl-phosphine oxide (SPPO1), and 9,9'-(5-(triphenylsilyl)-1,3-phenylene)bis(9H-carbazole) (SimCP), but are not limited thereto.
[0702] Each of the first blue dopant and the second blue dopant may be independently at least one selected from the group consisting of 4,4′-bis[4-(di-p-tolylamino)phenyl]biphenyl (DPAVBi), 4-(di-p-tolylamino)-4-4′-[(di-p-tolylamino)phenyl]styrene (DPAVB), 4,4′-bis[4-(diphenylamino)phenyl]biphenyl (BDAVBi), 2,7-bis(4-diphenylamino)phenyl)-9,9-spirofluorene (spiro-DPVBi), [1,4-bis[2-[4-[N,N-di(p-tolyl)amino]phenyl]vinyl]benzene (DSB), 1-4-bis-[4-(N,N-diphenyl)amino]phenyl-benzene (DSA), 2,5,8,11-tetra-tetrabutylperylene (TBPe), , bis(2-hydroxyphenyl)-pyridinium) beryllium (Bepp2), 9-(9-phenylcarbazol-3-yl)-10-(naphthalene-1-yl) anthracene (PCAN), mer-tris(1-phenyl-3-methylimidazolin-2-ylidene-C,C(2)'iridium(Ⅲ))(mer-Ir(pmi)3), fac-tris(1,3-diphenyl-benzimidazolin-2-ylidene-C,C(2)'iridium(Ⅲ))(fac- Ir(dpbic)3), bis(3,4,5-trifluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III) (Ir(tfpd)2pic), tris(2-(4,6-difluorophenyl)pyridine))iridium(III) (Ir(Fppy)3), and bis[2-(4,6-difluorophenyl)pyridine-C2,N](picolinate)iridium(III) (FIrpic), but are not limited thereto.
[0703] For example, each of the first blue EML 550 and the second blue EML 570 may include an anthracene derivative as a blue host and a boron derivative as a blue dopant.
[0704] The first CGL 580 may be located between the first light-emitting portion 530 and the second light-emitting portion 540, and the second CGL 590 may be located between the first light-emitting portion 530 and the third light-emitting portion 560. For example, the first light-emitting portion 530 and the second light-emitting portion 540 may be connected via the first CGL 580. The first light-emitting portion 530 and the third light-emitting portion 560 may be connected via the second CGL 590. The first CGL 580 may be a PN junction CGL including a first N-type CGL 582 and a first P-type CGL 584. The second CGL 590 may be a PN junction CGL including a second N-type CGL 592 and a second P-type CGL 594.
[0705] In the first CGL 580, a first N-type CGL 582 may be located between the first HTL 532 and the second ETL 546. A first P-type CGL 584 may be located between the first N-type CGL 582 and the first HTL 532.
[0706] In the second CGL 590, a second N-type CGL 592 may be located between the first ETL 534 and the third HTL 562. A second P-type CGL 594 may be located between the second N-type CGL 592 and the third HTL 562.
[0707] As described above, the OLED D of the present disclosure may include the first light emitting portion 530 including the green EML 510 and the red EML 520 , the second light emitting portion 540 including the first blue EML 550 , and the third light emitting portion 560 including the second blue EML 570 , so that white light may be provided from the OLED D.
[0708] The green EML 510 includes an example of the organic compound of the present disclosure represented by Formula 1. As a result, in the OLED D, driving voltage may be reduced, and luminous efficiency and lifespan may be improved.
[0709] When the organic compound in which the fused fluorene moiety in Formula 1 is deuterated is included in the green EML 510, the OLEDD can provide a sufficient increase in luminescence lifetime while minimizing an increase in production cost.
[0710] In addition, the green EML 510 may further include an example of the compound represented by Formula 3 as a second host when the first host is an example of the organic compound of the present disclosure, so that the OLED D may have advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0711] In addition, the green EML 510 may further include an example of a compound represented by Formula 5 as a light emitting body while having a first host represented by Formula 1 and a second host represented by Formula 3, so that the OLED D may have further advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0712] Furthermore, in the OLED D in the green pixel, at least one of the first ETL 534, the second ETL 546, and the third ETL 564 may include an example of the electron transport material represented by Formula 7, so that the OLED D may have advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0713] like Figure 7 As shown, the organic light-emitting layer 462 may include a first light-emitting portion 630 including a green EML 610, a red EML 620, and a yellow-green EML 625, a second light-emitting portion 640 including a first blue EML 650, and a third light-emitting portion 660 including a second blue EML 670. In addition, the organic light-emitting layer 462 may further include a first CGL 680 located between the first light-emitting portion 630 and the second light-emitting portion 640, and a second CGL 690 located between the first light-emitting portion 630 and the third light-emitting portion 660.
[0714] The second light-emitting portion 640 may be located between the first electrode 460 and the first light-emitting portion 630. The third light-emitting portion 660 may be located between the first light-emitting portion 630 and the second electrode 464. The second light-emitting portion 640 may be located between the first electrode 460 and the first CGL 680. The third light-emitting portion 660 may be located between the second CGL 690 and the second electrode 464. For example, the second light-emitting portion 640, the first CGL 680, the first light-emitting portion 630, the second CGL 690, and the third light-emitting portion 660 may be sequentially stacked on the first electrode 460.
[0715] In the first light emitting portion 630, the red EML 620 may be disposed below the yellow-green EML 625. The green EML 610 may be disposed on the yellow-green EML 625. For example, Figure 6 The first light emitting portion 530 of the OLED D may include an EML having a double-layer structure, which may include EMLs 510 and 520, and Figure 7 The first light emitting portion 630 of the OLED D in FIG. 4 may include an EML having a three-layer structure, which may include EMLs 610 , 620 , and 625 .
[0716] The first light emitting portion 630 may further include a first ETL 634 disposed on the green EML 610. In addition, the first light emitting portion 630 may further include a first HTL 632 disposed under the red EML 620.
[0717] For example, in the first light emitting portion 630, the red EML 620 may be located between the first HTL 632 and the yellow-green EML 625. The green EML 610 may be located between the yellow-green EML 625 and the first ETL 634.
[0718] The second light emitting portion 640 may further include at least one of a second HTL 644 disposed under the first blue EML 650 and a second ETL 646 disposed on the first blue EML 650. In addition, the second light emitting portion 640 may further include a HIL 642 between the first electrode 460 and the second HTL 644.
[0719] In addition, the second light emitting portion 640 may further include a first EBL (not shown) between the second HTL 644 and the first blue EML 650 , and a first HBL (not shown) between the second ETL 646 and the first blue EML 650 .
[0720] The third light emitting portion 660 may further include at least one of a third HTL 662 disposed under the second blue EML 670 and a third ETL 664 disposed on the second blue EML 670. In addition, the third light emitting portion 660 may further include an EIL 666 between the second electrode 464 and the third ETL 664.
[0721] In addition, the third light emitting portion 660 may further include a second EBL (not shown) between the third HTL 662 and the second blue EML 670 , and a second HBL (not shown) between the third ETL 664 and the second blue EML 670 .
[0722] The green EML 610 may include a first compound 612, which may be an example of an organic compound of the present disclosure represented by Formula 1. In addition, the green EML 610 may further include a second compound 614, which may be an example of a compound represented by Formula 3. In addition, the green EML 610 may further include a third compound 616, which may be an example of a compound represented by Formula 5.
[0723] In the green EML 610, the first compound 612 may be an n-type host (eg, a first host). The second compound 614 may be a p-type host (eg, a second host). The third compound 616 may be an illuminant (eg, a dopant). The green EML 610 may have thickness.
[0724] In green EML 610, the weight percentage of each of first compound 612 and second compound 614 may be greater than the weight percentage of third compound 616, and the weight percentage of first compound 612 and second compound 614 may be the same or different. In green EML 610, the weight percentage ratio of first compound 612 to second compound 614 may be 1:9 to 9:1, 2:8 to 8:2, or 7:3 to 3:7. In some embodiments, the weight percentage of first compound 612 and second compound 614 may be the same. For example, in green EML 610, first compound 612 and second compound 614 may be present at the same weight percentage, and third compound 616 may have a weight percentage of 5 to 25%.
[0725] Each of the first to third ETLs 634 , 646 , and 664 may include an example of the compound represented by Formula 7 as an electron transport material.
[0726] The red EML 620 may include a red host and a red dopant. The red dopant may include at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. In the red EML 620, the red host may be present in a greater weight percentage than the red dopant. In the red EML 620, the red dopant may be present in an amount of 1 to 10 weight percent, or 1 to 5 weight percent, based on the total weight of the components in the red EML 620.
[0727] The yellow-green EML 625 may include a yellow-green host and a yellow-green dopant. The yellow-green dopant may include at least one of a yellow-green phosphorescent compound, a yellow-green fluorescent compound, and a yellow-green delayed fluorescent compound. In the yellow-green EML 625, the yellow-green host may be present in an amount greater than the weight percentage of the yellow-green dopant. In the yellow-green EML 625, the yellow-green dopant may be present in an amount of 1 wt % to 10 wt %, or 1 wt % to 5 wt %, based on the total weight of the components in the yellow-green EML 625.
[0728] The first blue EML 650 in the second light emitting portion 640 may include a first blue host and a first blue dopant. The second blue EML 670 in the third light emitting portion 660 may include a second blue host and a second blue dopant.
[0729] Each of the first and second blue dopants may include at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In the first blue EML 650, the first blue host may be present in a greater weight percent than the first blue dopant. In the second blue EML 670, the second blue host may be present in a greater weight percent than the second blue dopant. In each of the first and second blue EMLs 650 and 670, the first and second blue dopants may be present in an amount of 1 to 10 weight percent, or 1 to 5 weight percent, based on the total weight of the components in each of the first and second blue EMLs 650 and 670.
[0730] The first CGL 680 may be located between the first light-emitting portion 630 and the second light-emitting portion 640. The second CGL 690 may be located between the first light-emitting portion 630 and the third light-emitting portion 660. For example, the first light-emitting portion 630 and the second light-emitting portion 640 may be connected via the first CGL 680. The first light-emitting portion 630 and the third light-emitting portion 660 may be connected via the second CGL 690. The first CGL 680 may be a PN junction CGL including a first N-type CGL 682 and a first P-type CGL 684. The second CGL 690 may be a PN junction CGL including a second N-type CGL 692 and a second P-type CGL 694.
[0731] In the first CGL 680, a first N-type CGL 682 may be located between the first HTL 632 and the second ETL 646. A first P-type CGL 684 may be located between the first N-type CGL 682 and the first HTL 632.
[0732] In the second CGL 690, the second N-type CGL 692 may be located between the first ETL 634 and the third HTL 662. The second P-type CGL 694 may be located between the second N-type CGL 692 and the third HTL 662.
[0733] As described above, the OLED D according to the exemplary embodiment of the present disclosure may include the first light emitting portion 630 including the green EML 610, the red EML 620, and the yellow-green EML 625, the second light emitting portion 640 including the first blue EML 650, and the third light emitting portion 660 including the second blue EML 670, so that white light can be provided from the OLED D.
[0734] The green EML 610 may include an example of the organic compound of the present disclosure represented by Formula 1. As a result, in an OLEDD, driving voltage may be reduced, and luminous efficiency and lifespan may be improved.
[0735] When the example of the organic compound in which the fused fluorene moiety in Formula 1 is deuterated is included in the green EML 610 , the OLED D can provide a sufficient increase in luminescence lifetime while minimizing an increase in production cost.
[0736] In addition, the green EML 610 may further include an example of the compound represented by Formula 3 as a second host when the first host is an example of the organic compound of the present disclosure, so that the OLED D may have advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0737] In addition, the green EML 610 may further include an example of a compound represented by Formula 5 as a light emitting body while having a first host represented by Formula 1 and a second host represented by Formula 3, so that the OLED D may have further advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0738] In addition, in the OLED D in the green pixel according to the exemplary embodiment of the present disclosure, at least one of the first ETL 634, the second ETL 646, and the third ETL 664 may include an example of the electron transport material represented by Formula 7, so that the OLED D can have advantages in aspects such as driving voltage, luminous efficiency, and luminous lifetime.
[0739] It will be apparent to those skilled in the art that various modifications and variations may be made to the embodiments of the present disclosure without departing from the spirit or scope of the present disclosure. Therefore, these modifications and variations are intended to encompass the present disclosure as long as they fall within the scope of the appended claims and their equivalents.
Claims
1. An organic compound represented by Formula 1: [Formula 1] Wherein L1 is represented by one of Formula 1a, Formula 1b, Formula 1c and Formula 1d: [Formula 1a] [Formula 1b] [Formula 1c] and [Formula 1d] wherein R1 and R2 are each independently selected from the group consisting of deuterium, cyano, halogen, and deuterium-substituted or unsubstituted C1 to C10 alkyl, and R3 is selected from the group consisting of deuterium, cyano, halogen, deuterium-substituted or unsubstituted C1 to C10 alkyl, and deuterium-substituted or unsubstituted C6 to C30 aryl, and wherein b1 is an integer from 0 to 3, and b2, b3 and b4 are each independently an integer from 0 to 4, and L2 is selected from the group consisting of a single bond and a deuterium-substituted or unsubstituted C6 to C30 arylene group, wherein one of X1 and X2 is a nitrogen atom, the other of X1 and X2 is O or S, wherein Ar1 is selected from the group consisting of hydrogen, deuterium, and deuterium-substituted or unsubstituted C6 to C30 aryl groups, and Ar2 and Ar3 are each a deuterium-substituted or unsubstituted C1 to C10 alkyl group, wherein Ar4 and Ar5 are each independently a deuterium-substituted or unsubstituted C6 to C30 aryl group, and in, a1 is an integer from 0 to 95, a2, a3, a4 and a5 are each independently an integer from 0 to 30, and at least one of a1 to a5 is a positive integer. 2 . The organic compound according to claim 1 , wherein a1, a2, a3, a4 and a5 are each a positive integer. 3 . The organic compound according to claim 1 , wherein in Formula 1, a1 is a positive integer, and a2, a3, a4, and a5 are each 0. The organic compound according to claim 1 , wherein in Formula 1, a1 and a2 are each a positive integer, and a3, a4, and a5 are each 0.
5. The organic compound according to claim 1, wherein the organic compound is one of the compounds of Formula 2: [Formula 2] 6. An organic light-emitting device, comprising: substrate; and an organic light emitting diode, the organic light emitting diode being located on the substrate and comprising a first electrode; a second electrode facing the first electrode; and a first light-emitting portion located between the first electrode and the second electrode, wherein the first light-emitting portion includes a first green light-emitting material layer, The first green light emitting material layer includes a first compound, which is an organic compound represented by Formula 1: [Formula 1] Wherein L1 is represented by one of Formula 1a, Formula 1b, Formula 1c and Formula 1d: [Formula 1a] [Formula 1b] [Formula 1c] and [Formula 1d] wherein R1 and R2 are each independently selected from the group consisting of deuterium, cyano, halogen, and deuterium-substituted or unsubstituted C1 to C10 alkyl, and R3 is selected from the group consisting of deuterium, cyano, halogen, deuterium-substituted or unsubstituted C1 to C10 alkyl, and deuterium-substituted or unsubstituted C6 to C30 aryl, and wherein b1 is an integer from 0 to 3, and b2, b3 and b4 are each independently an integer from 0 to 4, and L2 is selected from the group consisting of a single bond and a deuterium-substituted or unsubstituted C6 to C30 arylene group, wherein one of X1 and X2 is a nitrogen atom, and the other of X1 and X2 is O or S, wherein Ar1 is selected from the group consisting of hydrogen, deuterium, and deuterium-substituted or unsubstituted C6 to C30 aryl groups, Ar2 and Ar3 are each deuterium-substituted or unsubstituted C1 to C10 alkyl groups, wherein Ar4 and Ar5 are each independently a deuterium-substituted or unsubstituted C6 to C30 aryl group, and wherein a1 is an integer from 0 to 95, a2, a3, a4, and a5 are each independently an integer from 0 to 30, and at least one of a1 to a5 is a positive integer.
7. The organic light-emitting device according to claim 6, wherein the first green light-emitting material layer further comprises a second compound, wherein the second compound is one of the compounds of formula 4: [Formula 4] 8. The organic light-emitting device according to claim 6, wherein the first green light-emitting material layer further comprises a third compound, wherein the third compound is one of the compounds of Formula 6: [Formula 6] 9. The organic light-emitting device according to claim 6, wherein the first light-emitting portion further comprises a first electron transport layer located between the first green light-emitting material layer and the second electrode, wherein the first electron transport layer comprises an electron transport material, wherein the electron transport material is one of the compounds of formula 8: [Formula 8] 10. The organic light-emitting device according to claim 6, further comprising: a second light-emitting portion, the second light-emitting portion including a second green light-emitting material layer and located between the first light-emitting portion and the second electrode; The second green light-emitting material layer includes the first compound.
11. The organic light-emitting device according to claim 6, further comprising: a second light-emitting portion, the second light-emitting portion including a first blue light-emitting material layer and located between the first electrode and the first light-emitting portion; and The third light-emitting portion includes a second blue light-emitting material layer and is located between the first light-emitting portion and the second electrode. 12 . The organic light-emitting device according to claim 11 , wherein the first light-emitting portion further comprises a red light-emitting material layer between the second light-emitting portion and the first green light-emitting material layer. 13 . The organic light-emitting device according to claim 12 , wherein the first light-emitting portion further comprises a yellow-green light-emitting material layer located between the first green light-emitting material layer and the red light-emitting material layer. 14 . The organic light-emitting device according to claim 6 , wherein in Formula 1, a1 is a positive integer, and a2, a3, a4, and a5 are each 0. 15 . The organic light-emitting device according to claim 6 , wherein in Formula 1, a1 and a2 are each a positive integer, and a3, a4, and a5 are each 0.
16. The organic light-emitting device according to claim 6, wherein the organic compound is one of the compounds of Formula 2: [Formula 2]
Citation Information
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