Organic compound, and organic light emitting diode and organic light emitting device including the same
Incorporating an organic compound with a triazine core and specific moieties into the light-emitting material layer of OLEDs addresses the issues of high driving voltage and low luminous efficiency, resulting in improved performance and reduced power consumption.
Patent Information
- Application Number
- JP2024189939
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-11-06
- Filing Date
- 2024-10-29
- Publication Date
- 2025-05-19
AI Technical Summary
Existing organic light emitting diodes (OLEDs) face limitations in driving voltage and luminous efficiency.
The use of a specific organic compound represented by Chemical Formula 1, which includes a triazine core bonded to benzoxazole, carbazole, and other moieties, is introduced as a key component in the light-emitting material layer of OLEDs.
This organic compound reduces the driving voltage of OLEDs and enhances light-emitting efficiency, enabling low-power driving and improved performance.
Smart Images

Figure 2025078034000001_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to an organic compound, and more particularly, to an organic compound having advantages in driving voltage and luminous efficiency, and an organic light emitting diode and an organic light emitting device including the same.
Background Art
[0002] Recently, with the increase in the size of display devices, the demand for flat panel display elements that occupy less space has been increasing. As one of such flat panel display elements, the technology of organic light emitting diodes (OLEDs) has been developing rapidly.
[0003] When electrons and holes are injected from a cathode and an anode into a light emitting material layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) in an organic light emitting diode, the organic light emitting diode is an element that emits light while the electrons and holes pair up and then disappear. The element can be formed not only on a flexible transparent substrate such as plastic, but also can be driven at a low voltage (10 V or less), and has advantages such as relatively low power consumption and excellent color rendering.
[0004] An organic light emitting diode is formed on the upper part of a substrate and includes a first electrode as an anode, a second electrode facing the first electrode with a separation therebetween, and an organic light emitting layer located between the first electrode and the second electrode.
[0005] Although there have been many studies and developments on the materials of the organic light emitting layer, to date, organic light emitting diodes have limitations in driving voltage and luminous efficiency.
Summary of the Invention
Problems to be Solved by the Invention
[0006] The present invention aims to solve the problems of high driving voltage and low luminous efficiency in organic light emitting diodes and organic light emitting devices.
Means for Solving the Problems
[0007] In order to solve the above problems, the present invention is represented by Chemical Formula 1, where a1 is an integer from 0 to 5, a2 is an integer from 0 to 3, and R 1 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, and R 2 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group. When a1 is 2 or more, a plurality of R 1 may be the same as or different from each other. When a2 is 2 or more, a plurality of R 2 may be the same as or different from each other. L 1 L 2 L 3 each is independently selected from the group consisting of a single bond (direct bond), a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group. Ar 1 is selected from Chemical Formulas 1a-1 to 1a-5. In Chemical Formula 1a-1, b1 is an integer from 0 to 5. In Chemical Formula 1a-2, b2 is an integer from 0 to 7. In each of Chemical Formulas 1a-3 to 1a-5, b3 is an integer from 0 to 4. In Chemical Formula 1a-4, V 1 is selected from O, S, C(R 3 ) 2 and in Chemical Formula 1a-5, V 2 is selected from O and S. In each of Chemical Formulas 1a-1 to 1a-5, R 3 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group. When b1, b2, or b3 is 2 or more, a plurality of R 3 may be the same as or different from each other. Ar 2 is selected from Chemical Formulas 1b-1 and 1b-2. In each of Chemical Formulas 1b-1 and 1b-2, b4 is an integer from 0 to 4, and R 4Each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group. When b4 is 2 or more, a plurality of R 4 may be the same as or different from each other. In Chemical Formula 1b-2, R 5 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C30 aryl group, and provides an organic compound.
[0008] [Chemical Formula 1] TIFF2025078034000002.tif79170
[0009] [Chemical Formula 1a-1] TIFF2025078034000003.tif24170
[0010] [Chemical Formula 1a-2] TIFF2025078034000004.tif51170
[0011] [Chemical Formula 1a-3] TIFF2025078034000005.tif60170
[0012] [Chemical Formula 1a-4] TIFF2025078034000006.tif41170
[0013] [Chemical Formula 1a-5] TIFF2025078034000007.tif46170
[0014] [Chemical Formula 1b-1] TIFF2025078034000008.tif32170
[0015] [Chemical Formula 1b-2] TIFF2025078034000009.tif39170
[0016] In the organic compound of the present invention, Ar 1 and Ar 2 may be different from each other.
[0017] In another aspect, the present invention provides an organic light-emitting diode including a substrate; a first electrode; a second electrode facing the first electrode; and a first light-emitting part including a first light-emitting material layer and located between the first electrode and the second electrode, the organic light-emitting diode being located above the substrate; wherein the first light-emitting material layer contains a first compound which is the organic compound described above.
[0018] In the organic light-emitting diode according to the present invention, the light-emitting material layer contains the organic compound (first host) of the present invention, and has the effect that the driving voltage of the organic light-emitting diode and the organic light-emitting device is reduced, the light-emitting efficiency is improved, and low-power driving is possible.
[0019] Also, in the organic light-emitting diode according to the present invention, the light-emitting material layer contains a first host, a second host and a dopant, and has the effect that the driving voltage of the organic light-emitting diode and the organic light-emitting device is further reduced, the light-emitting efficiency is further improved, and low-power driving is possible.
[0020] Also, in the organic light-emitting diode according to the present invention, by including at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a third electron transport material represented by Chemical Formula 8 in the electron transport layer adjacent to the light-emitting material layer, the driving voltage of the organic light-emitting diode and the organic light-emitting device is further reduced, the light-emitting efficiency is further improved, and low-power driving is possible.
[0021] Also, the organic light-emitting diode of the present invention has a multi-stack structure by including a first light-emitting part including a first green light-emitting material layer and a second green light-emitting part including a second green light-emitting material layer, and at least one of the first and second green light-emitting material layers contains the organic compound of the present invention having a specific structure (Chemical Formula 1). Therefore, in the organic light-emitting diode of the present invention and the organic light-emitting device including the same, the driving voltage is reduced and the light-emitting efficiency is increased.
[0022] In addition, the organic light-emitting diode of the present invention has a multi-stack structure by including a first light-emitting part including a first yellow-green light-emitting material layer and a second light-emitting part including a second green light-emitting material layer, and at least one of the first and second yellow-green light-emitting material layers contains the organic compound of the present invention having a specific structure (Chemical Formula 1). Therefore, in the organic light-emitting diode of the present invention and the organic light-emitting device including the same, the driving voltage decreases and the light-emitting efficiency increases.
[0023] In addition, the present invention provides a white organic light-emitting diode having a multi-stack structure including at least one of a green light-emitting material layer and a yellow-green light-emitting material layer, and at least one of the green light-emitting material layer and the yellow-green light-emitting material layer contains the organic compound of the present invention having a specific structure (Chemical Formula 1). Therefore, in the organic light-emitting diode of the present invention and the organic light-emitting device including the same, the driving voltage decreases and the light-emitting efficiency increases.
Brief Description of Drawings
[0024]
Figure 1
[0025]
Figure 2
[0026]
Figure 3
[0027]
Figure 4
[0028]
Figure 5
[0029]
Figure 6
[0030]
Figure 7
[0031]
Figure 8
[0032]
Figure 9
[0033]
Figure 10
Embodiments for Carrying Out the Invention
[0034] The advantages and features of the present invention, and the methods for achieving them, will become clear by referring to the embodiments described in detail below together with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below and can be embodied in various different forms. However, this embodiment is provided to make the disclosure of the present invention complete and to fully inform those with ordinary knowledge in the technical field to which the present invention belongs of the scope of the invention, and the present invention is only defined by the scope of the claims.
[0035] The shapes, sizes, ratios, angles, numbers, etc. disclosed in the drawings for explaining the embodiments of the present invention are exemplary, and thus the present invention is not limited to the illustrated matters. Throughout the specification, the same reference numerals denote the same components. Further, in the description of the present invention, when it is determined that a specific description of related known technologies may obscure the gist of the present invention unnecessarily, the detailed description thereof is omitted. When terms such as "including," "having," "becoming," etc. mentioned in this specification are used, other parts may be added as long as "only" is not used. When a component is expressed in the singular, it includes the case of including a plurality unless there is a specific base matter explicitly stated.
[0036] In interpreting a component, it is interpreted to include an error range even without a separate explicit description.
[0037] In the case of an explanation of a positional relationship, for example, when the positional relationship between both parts is explained by, for example, "on ~," "above ~," "below ~," "beside ~," etc., one or more other parts may be located between both parts as long as "immediately" or "directly" is not used.
[0038] In the case of an explanation of a time relationship, for example, when the temporal front-back relationship is explained by, for example, "after ~," "subsequent to ~," "next to ~," "before ~," etc., cases where it is not continuous can also be included as long as "immediately" or "directly" is not used.
[0039] First, second, etc. are used to describe various components, but these components are not limited by these terms. These terms are merely used to distinguish one component from another. Therefore, the first component mentioned below may be the second component within the technical idea of the present invention.
[0040] The respective features of the various embodiments of the present invention can be partially or wholly combined or combined with each other, enabling various technical linkages and drives, and each embodiment may be implemented independently of each other or may be implemented together in a correlation relationship.
[0041] Hereinafter, preferred embodiments according to the present invention will be described with reference to the drawings.
[0042] The organic light-emitting diode of the present invention contains the organic compound of the present invention. Such an organic light-emitting diode can be included in an organic light-emitting device such as an organic light-emitting display device or a lighting device. As an example, a display device applying the organic light-emitting diode according to the present invention will be described.
[0043] FIG. 1 is a schematic circuit diagram of an organic light-emitting display device.
[0044] As shown in FIG. 1, in the organic light-emitting display device, a gate wiring GL, a data wiring DL, and a power wiring PL that intersect each other to define a pixel region P are formed, and in the pixel region P, a switching thin-film transistor Ts, a driving thin-film transistor Td, a storage capacitor Cst, and an organic light-emitting diode D are formed. The pixel region P may include a red pixel region, a green pixel region, and a blue pixel region. Further, the pixel region P can further include a white pixel region.
[0045] The switching thin-film transistor Ts is connected to the gate wiring GL and the data wiring DL, and the driving thin-film transistor Td and the storage capacitor Cst are connected between the switching thin-film transistor Ts and the power wiring PL. The organic light-emitting diode D is connected to the driving thin-film transistor Td.
[0046] In such an organic light-emitting display device, when the switching thin-film transistor Ts is turned on by a gate signal applied to the gate wiring GL, the data signal applied to the data wiring DL is applied to the gate electrode of the driving thin-film transistor Td and one electrode of the storage capacitor Cst through the switching thin-film transistor Ts.
[0047] The driving thin film transistor Td is turned on by a data signal applied to the gate electrode. As a result, a current proportional to the data signal flows from the power wiring PL through the driving thin film transistor Td to the organic light emitting diode D. The organic light emitting diode D emits light with a luminance proportional to the current flowing through the driving thin film transistor Td.
[0048] At this time, the storage capacitor Cst is charged with a voltage proportional to the data signal, and the voltage of the gate electrode of the driving thin film transistor Td is maintained constant during one frame.
[0049] Therefore, the organic light emitting display device can display a desired video.
[0050] FIG. 2 is a schematic cross-sectional view of an organic light emitting display device according to the first embodiment of the present invention.
[0051] As shown in FIG. 2, the organic light emitting display device 100 includes a thin film transistor Tr located on the substrate 110 and an organic light emitting diode D connected to the thin film transistor Tr. For example, a red pixel region, a green pixel region, and a blue pixel region are defined on the substrate 110, and the organic light emitting diode D is located in each of the red pixel region, the green pixel region, and the blue pixel region. A yellow-green pixel region may be further defined on the substrate 110. In this case, the organic light emitting diode D is also located in the yellow-green pixel region. That is, organic light emitting diodes D that emit red, green, and blue light are provided in the red pixel region, the green pixel region, the blue pixel region, and the yellow-green pixel region, respectively.
[0052] The substrate 110 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be any one of a polyimide (PI) substrate, a polyether sulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, and a polycarbonate (PC) substrate.
[0053] A buffer layer 120 is formed on a substrate 110, and a thin film transistor Tr is formed on the buffer layer 120. The buffer layer 120 may be made of an inorganic insulating material such as silicon oxide or silicon nitride. Further, the buffer layer 120 may have a multilayer structure by including a first layer made of silicon oxide and a second layer made of silicon nitride. The buffer layer 120 may be omitted, and in this case, the thin film transistor Tr may be formed on the substrate 110.
[0054] A semiconductor layer 122 is formed on the buffer layer 120. The semiconductor layer 122 may be made of an oxide semiconductor material or may be made of polycrystalline silicon.
[0055] When the semiconductor layer 122 is made of an oxide semiconductor material, a light shielding pattern (not shown) may be formed below the semiconductor layer 122. The light shielding pattern prevents light from entering the semiconductor layer 122 and prevents the semiconductor layer 122 from deteriorating due to light. Alternatively, the semiconductor layer 122 may be made of polycrystalline silicon, and in this case, impurities may be doped at both ends of the semiconductor layer 122.
[0056] A gate insulating film 124 made of an insulating material is formed on the upper part of the semiconductor layer 122. The gate insulating film 124 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.
[0057] A gate electrode 130 made of a conductive material such as metal is formed corresponding to the center of the semiconductor layer 122 on the upper part of the gate insulating film 124.
[0058] In FIG. 2, although the gate insulating film 124 is formed on the front surface of the substrate 110, the gate insulating film 124 may be patterned in the same shape as the gate electrode 130.
[0059] On top of the gate electrode 130, an interlayer insulating film 132 made of an insulating material is formed. The interlayer insulating film 132 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or may be formed of an organic insulating material such as benzocyclobutene or photo-acryl.
[0060] The interlayer insulating film 132 has first and second contact holes 134 and 136 that expose both sides of the semiconductor layer 122. The first and second contact holes 134 and 136 are positioned at a distance from the gate electrode 130 on both sides of the gate electrode 130.
[0061] Here, the first and second contact holes 134 and 136 are formed in the interlayer insulating film 132 and the gate insulating film 124. Alternatively, when the gate insulating film 124 is patterned in the same shape as the gate electrode 130, the first and second contact holes 134 and 136 may be formed only within the interlayer insulating film 132.
[0062] On the interlayer insulating film 132, a source electrode 140 and a drain electrode 142 made of a conductive material such as metal are formed.
[0063] The source electrode 140 and the drain electrode 142 are positioned at a distance from each other with the gate electrode 130 as the center, and are in contact with both sides of the semiconductor layer 122 via the first and second contact holes 134 and 136, respectively.
[0064] The semiconductor layer 122, the gate electrode 130, the source electrode 140, and the drain electrode 142 form a thin film transistor Tr, and the thin film transistor Tr functions as a driving element.
[0065] The thin film transistor Tr has a coplanar structure in which the gate electrode 130, the source electrode 140, and the drain electrode 142 are positioned on top of the semiconductor layer 122.
[0066] Alternatively, the thin film transistor Tr may have an inverted staggered structure in which the gate electrode is located below the semiconductor layer and the source and drain electrodes are located above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon.
[0067] Although not shown, a gate wiring and a data wiring intersect each other to define a pixel region, and a switching element connected to the gate wiring and the data wiring is further formed. The switching element is connected to the thin film transistor Tr as a driving element.
[0068] Also, a power wiring may be formed separated from or parallel to the data wiring, and a storage capacitor may be further configured to maintain the voltage of the gate electrode of the thin film transistor Tr as a driving element constant during one frame.
[0069] A planarization layer 150 having a drain contact hole 152 that exposes the drain electrode 142 of the thin film transistor Tr is formed to cover the thin film transistor Tr.
[0070] On the planarization layer 150, a first electrode 160 connected to the drain electrode 142 of the thin film transistor Tr through the drain contact hole 152 is separately formed for each pixel region.
[0071] The first electrode 160 may be an anode and may include a transparent conductive oxide layer made of a conductive material having a relatively large work function value, for example, a transparent conductive oxide (TCO). For example, the transparent conductive oxide layer of the first electrode 160 may include at least one of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO), and aluminum: zinc oxide (Al:ZnO; AZO).
[0072] When the organic light-emitting display device 100 of the present invention is of the bottom-emission type, the first electrode 160 may have a single-layer structure of a transparent conductive oxide layer.
[0073] Alternatively, when the organic light-emitting display device 100 of the present invention is of the top-emission type, the first electrode 160 may further include a reflective layer and may have a double-layer or triple-layer structure. For example, the reflective layer may be made of silver or an aluminum-palladium-copper (APC) alloy. In the organic light-emitting diode D of the top-emission type, the first electrode 160 may have a double-layer structure of Ag / ITO or APC / ITO, or a triple-layer structure of ITO / Ag / ITO or ITO / APC / ITO.
[0074] Also, a bank layer 166 covering the end portion of the first electrode 160 is formed on the planarization layer 150. The bank layer 166 corresponds to the pixel region and exposes the center of the first electrode 160.
[0075] An organic light-emitting layer 162 is formed on the first electrode 160. The organic light-emitting layer 162 may include one light-emitting portion including a light-emitting material layer. Alternatively, the organic light-emitting layer 162 may include a plurality of light-emitting portions each including a light-emitting material layer. Further, the organic light-emitting layer 162 may further include a charge generation layer (CGL) positioned between adjacent light-emitting portions.
[0076] Each of the light-emitting portions may further include at least one of a hole injection layer (HIL), a hole transporting layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transporting layer (ETL), and an electron injection layer (EIL), and may have a multilayer structure.
[0077] The organic light-emitting layer 162 is separately positioned in a red pixel region, a green pixel region, and a blue pixel region. As will be described later, in the organic light-emitting diode D in the green pixel region, the organic light-emitting layer 162 contains the organic compound of the present invention, and the driving voltage of the organic light-emitting diode D and the organic light-emitting display device 100 including the same decreases, and the light-emitting efficiency increases. For example, the light-emitting material layer of the organic light-emitting layer 162 may contain the organic compound of the present invention.
[0078] A second electrode 164 is formed on the upper portion of the substrate 110 on which the organic light-emitting layer 162 is formed. The second electrode 164 is positioned in front of the display region, is made of a conductive material having a relatively small work function value, and can be used as a cathode. For example, the second electrode 164 may be made of any one of aluminum (Al), magnesium (Mg), silver (Ag), or an alloy thereof, for example, an aluminum-magnesium alloy (AlMg) or a silver-magnesium alloy (MgAg). When the organic light-emitting display device 100 is an upper light-emitting type, the second electrode 164 has a thin thickness and has light transmission (semi-transmission) characteristics.
[0079] The first electrode 160, the organic light-emitting layer 162, and the second electrode 164 form an organic light-emitting diode D.
[0080] On the second electrode 164, a encapsulation layer (or encapsulation film) 170 is formed to prevent external moisture from penetrating into the organic light-emitting diode D. The encapsulation layer 170 may have a laminated structure of a first inorganic insulating layer 172, an organic insulating layer 174, and a second inorganic insulating layer 176, but is not limited thereto. Also, the encapsulation layer 170 may be omitted.
[0081] When the organic light-emitting display device 100 is a bottom-emission type, a metal plate (not shown) may be further provided on the encapsulation layer 170.
[0082] The organic light-emitting display device 100 may include a color filter (not shown) corresponding to red, green, and blue pixel regions. The color filter layer may include a red color filter pattern, a green color filter pattern, and a blue color filter pattern corresponding to the red pixel region, the green pixel region, and the blue pixel region, respectively. When the organic light-emitting display device 100 includes a color filter layer, the color purity of the organic light-emitting display device 100 can be improved.
[0083] When the organic light-emitting display device 100 is a bottom-emission type, a color filter may be located between the organic light-emitting diode D and the substrate 110, for example, between the interlayer insulating film 132 and the planarization layer 150. Alternatively, when the organic light-emitting display device 100 is a top-emission type, the color filter may be located above the organic light-emitting diode D, for example, above the second electrode 164 or above the encapsulation layer 170.
[0084] The organic light-emitting display device 100 may further include a polarizing plate (not shown) for reducing the reflection of external light. For example, the polarizing plate may be a circular polarizing plate. When the organic light-emitting display device 100 is a bottom-emitting type, the polarizing plate may be located below the substrate 110. In addition, when the organic light-emitting display device 100 of the present invention is a top-emitting type, the polarizing plate may be located above the encapsulation layer 170.
[0085] Moreover, in the top-emitting type organic light-emitting display device 100, a cover window (not shown) may be attached on the encapsulation layer 170 or the polarizing plate. At this time, the substrate 110 and the cover window have flexible characteristics, and a flexible organic light-emitting display device can be implemented.
[0086] In addition, the organic light-emitting display device 100 may further include a touch layer or a touch panel located between the organic light-emitting diode D and the cover window.
[0087] FIG. 3 is a schematic cross-sectional view of an organic light-emitting diode according to a second embodiment of the present invention.
[0088] As shown in FIG. 3, the organic light-emitting diode D includes first and second electrodes 160 and 164 facing each other, and an organic light-emitting layer 162 located between the first and second electrodes 160 and 164. The organic light-emitting layer 162 includes an emitting material layer 230 (EML). The emitting material layer 230 may be a green emitting material layer or a yellow-green emitting material layer.
[0089] The organic light-emitting display device (100 in FIG. 2) includes at least one of a red pixel region, a green pixel region, a blue pixel region, and a yellow-green pixel region, and the organic light-emitting diode D may be located in at least one of the green pixel region and the yellow-green pixel region. The organic light-emitting diode D includes a red emitting material layer in the red pixel region and a blue emitting material layer in the blue pixel region.
[0090] The first electrode 160 is a positive electrode that injects holes, and the second electrode 164 is a negative electrode that injects electrons. Also, one of the first electrode 160 and the second electrode 164 is a reflective electrode, and the other of the first electrode 160 and the second electrode 164 is a transmissive (semi-transmissive) electrode.
[0091] For example, the first electrode 160 may include a transparent conductive material layer made of ITO or IZO, and the second electrode 164 may be made of any one of aluminum (Al), magnesium (Mg), silver (Ag), aluminum-magnesium alloy (AlMg), and silver-magnesium alloy (MgAg).
[0092] The light-emitting material layer 230 includes a first compound 232 which is an organic compound of the present invention represented by Chemical Formula 1.
[0093] [Chemical Formula 1] TIFF2025078034000010.tif79170
[0094] In Chemical Formula 1, a1 is an integer from 0 to 5, and a2 is an integer from 0 to 3. R 1 Each is independently selected from the group consisting of deuterium, substituted or unsubstituted C1-C10 alkyl groups. R 2 Each is independently selected from the group consisting of deuterium, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups. When a1 is 2 or more, the plurality of R 1 may be the same as or different from each other. When a2 is 2 or more, the plurality of R 2 may be the same as or different from each other. L 1 L 2 L 3 Each is independently selected from the group consisting of a single bond (direct bond), substituted or unsubstituted C6-C60 arylene groups, and substituted or unsubstituted C3-C60 heteroarylene groups. Ar 1 is selected from Chemical Formula 1a-1 to Chemical Formula 1a-5, [Chemical Formula 1a-1] TIFF2025078034000011.tif24170
[0095] [Chemical Formula 1a-2] TIFF2025078034000012.tif51170
[0096] [Chemical Formula 1a-3] TIFF2025078034000013.tif60170
[0097] [Chemical Formula 1a-4] TIFF2025078034000014.tif41170
[0098] [Chemical Formula 1a-5] TIFF2025078034000015.tif46170
[0099] In Chemical Formula 1a-1, b1 is an integer from 0 to 5, In Chemical Formula 1a-2, b2 is an integer from 0 to 7, In each of Chemical Formulas 1a-3 to 1a-5, b3 is an integer from 0 to 4, In Chemical Formula 1a-4, V 1 is selected from O, S, C(R 3 ) 2 and is selected from, In Chemical Formula 1a-5, V 2 is selected from O and S, In each of Chemical Formulas 1a-1 to 1a-5, each R 3 is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group, When each of b1, b2, and b3 is 2 or more, the plurality of R 3 may be the same as or different from each other, Ar 2is selected from Chemical Formula 1b-1 and Chemical Formula 1b-2, [Chemical Formula 1b-1] TIFF2025078034000016.tif32170
[0100] [Chemical Formula 1b-2] TIFF2025078034000017.tif39170
[0101] In each of Chemical Formula 1b-1 and Chemical Formula 1b-2, b4 is an integer from 0 to 4, R 4 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group, When b4 is 2 or more, a plurality of R 4 may be the same as or different from each other, In Chemical Formula 1b-2, R 5 each is independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C30 aryl group.
[0102] In each of Chemical Formula 1a-1 to Chemical Formula 1a-5, Chemical Formula 1b-1, and Chemical Formula 1b-2, the "*" indicates a bonding site.
[0103] In the present invention, "unsubstituted" means that a hydrogen atom is present only to satisfy the valency of the compound.
[0104] In the present invention, unless otherwise specified, the substituents of an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an arylene group, or a heteroarylene group may include at least one of deuterium (D), a halogen, a cyano group, a hydroxy group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C3-C30 cycloalkyl group, a C1-C10 alkylsilyl group, a C1-C10 alkylamino group, a C6-C30 arylsilyl group, a C6-C30 amino group, a C6-C30 aryl group, and a C3-C30 heteroaryl group. For example, the substituents may be selected from the group consisting of D, F, Br, CN, hydroxyl, methyl, ethyl, propyl, butyl (e.g., tert-butyl), methoxy, ethoxy, propoxy, butoxy (e.g., tert-butoxy), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trimethylsilyl, trimethylamino, triphenylsilyl, triphenylamino, phenyl, biphenyl, naphthyl, anthracenyl, pyridyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.
[0105] In the present invention, unless otherwise specified, "alkyl" means a substituted or unsubstituted linear or branched hydrocarbon chain radical. For example, the C1-C10 alkyl group may be selected from the group consisting of methyl, ethyl, propyl, and butyl (e.g., t-butyl).
[0106] In the present invention, unless otherwise stated, "aryl" means a monovalent monocyclic or polycyclic conjugated ring structure. For example, the aryl group of C6 to C60 can be selected from the group consisting of phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, pentalenyl group, indenyl group, indenoindenyl group, heptalenyl group, biphenylene group, indacenyl group, phenalenyl group, phenanthrenyl group, benzophenanthrenyl group, dibenzophenanthrenyl group, azulenyl group, pyrenyl group, fluoranthenyl group, triphenylene group, chrysenyl group, tetraphenyl group, tetracenyl group, periadylenyl group, picenyl group, pentaphenyl group, pentacenyl group, fluorenyl group, indenofluorenyl group, spirofluorenyl group.
[0107] In the present invention, unless otherwise stated, "arylene" means a divalent monocyclic or polycyclic conjugated ring structure. For example, the arylene group of C6 to C60 can be selected from the group consisting of phenylene group, biphenylene group, terphenylene group, naphthylene group, anthracenylene group, pentalenylene group, indenylene group, indenoindenylene group, heptalenylene group, biphenylenylene group, indacenylene group, phenalenylene group, phenanthrenylene group, benzophenanthrenylene group, dibenzophenanthrenylene group, azulenylene group, pyrenylene group, fluoranthenylene group, triphenylene group, chrysenylene group, tetraphenylene group, tetracenylene group, periadylenyl group, picenylene group, pentaphenylene group, pentacenylene group, fluorenylene group, indenofluorenylene group, spirofluorenylene group.
[0108] In the present invention, unless otherwise described, the C3-C60 heteroaryl group can be selected from the group consisting of a pyrrolyl group, a pyridinyl group, a pyrimidinyl 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, an indolizinyl group, a pyrrolidinyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an indolocarbazolyl group, an indenocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a quinazolinyl group, a quinolidinyl group, a purinyl group, a phthalazinyl group, a quinoxalinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a benzobenzazolinyl group, a benzobenzoxalinyl group, an acridinyl group, a phenanthrolinyl group, a perimidinyl group, a phenanthridinyl group, a pteridinyl group, a cinnolinyl group, a naphthyridinyl group, a furanyl group, a pyranyl group, an oxazinyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a dioxinyl group, a benzofuranyl group, a dibenzofuranyl group, a thiopyranyl group, a xanthenyl group, a chromenyl group, an isochromenyl group, a thiazinyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a difuropyrazinyl group, a benzofurodibenzofuranyl group, a benzothienobenzothiophenyl group, a benzothienodibenzothiophenyl group, a benzothienobenzofuranyl group, a benzothienodibenzofuranyl group.
[0109] In the present invention, unless otherwise stated, the C3-C60 heteroarylene group can be selected from the group consisting of a pyrrolylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a tetrazinylene group, an imidazoylene group, a pyrazoylene group, an indolylene group, an isoindolylene group, an indazoylene group, an indolizinylene group, a pyrrolidinylene group, a carbazoylene group, a benzocarbazoylene group, a dibenzocarbazoylene group, an indolocarbazoylene group, an indenocarbazoylene group, a benzofurocarbazoylene group, a benzothienocarbazoylene group, a quinolinylene group, an isoquinolinylene group, a phthalazinylene group, a quinoxalinylene group, a cinnolinylene group, a quinazolinylene group, a quinoxazolinylene group, a quinolidinylene group, a phrenylene group, a phthalazinylene group, a quinoxalinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a benzquinazolinylene group, a benzquinoxalinylene group, an acridinylene group, a phenanthrolinylene group, a perimidinylene group, a phenanthridinylene group, a pteridinylene group, a synnolinylene group, a naphthyridinylene group, a furanylene group, a pyranylene group, an oxazinylene group, an oxazoylene group, an oxadiazolylene group, a triazolylene group, a deoxynylene group, a benzofuranylene group, a dibenzofuranylene group, a thiopyranylene group, a xanthenylen group, a chromenylene group, an isochromenylene group, a thioazinylene group, a thiophenylene group, a benzothiophenylene group, a dibenzothiophenylene group, a difuropyrazinylene group, a benzofurodibenzofuranylene group, a benzothieno-benzothiophenylene group, a benzothienodibenzothiophenylene group, a benzothienobenzofuranylene group, a benzothienodibenzofuranylene group.
[0110] In one embodiment of the present invention, R 1 may be an unsubstituted or C1-C10 alkyl group (e.g., methyl) substituted C6-C60 aryl group (e.g., phenyl).
[0111] In one embodiment of the present invention, a may be 0.
[0112] In one embodiment of the present invention, L1 and L 2 and L 3 Each may be an arylene group of C6 to C60 (for example, phenylene).
[0113] In one embodiment of the present invention, each of b1 to b3 may be an integer of 0 to 2.
[0114] In one embodiment of the present invention, R 3 Each may independently be a substituted or unsubstituted C1 - C10 alkyl group (for example, methyl, t - butyl) or a substituted or unsubstituted C6 - C60 aryl group (for example, phenyl).
[0115] In one embodiment of the present invention, b4 may be 0 or 1.
[0116] In one embodiment of the present invention, R 4 and R 5 Each may be a substituted or unsubstituted C6 - C60 aryl group (for example, phenyl).
[0117] As shown in Chemical Formula 1, the organic compound of the present invention has a structure in which a first moiety that is benzoxazole, a second moiety that is carbazole, and a third moiety selected from Chemical Formulas 1a - 1 to 1a - 5 are bonded to a triazine core directly or via a linker. That is, the organic compound of the present invention includes a triazine core, a first moiety that is benzoxazole, a second moiety that is carbazole, and a third moiety different from the first and second moieties. Thereby, an organic light - emitting diode and an organic light - emitting display device using the organic compound have advantages in at least one of driving voltage and luminous efficiency.
[0118] In Chemical Formula 1, the bonding position of L 3 to the benzoxazole moiety is specified. For example, the organic compound of the present invention can be represented by one of Chemical Formulas 1 - 1 to 1 - 4.
[0119] [Chemical Formula 1-1] TIFF2025078034000018.tif60170
[0120] [Chemical Formula 1-2] TIFF2025078034000019.tif98170
[0121] [Chemical Formula 1-3] TIFF2025078034000020.tif98170
[0122] [Chemical Formula 1-4] TIFF2025078034000021.tif62170
[0123] In each of Chemical Formulas 1-1 to 1-4, a1, a2, R 1 , R 2 , L 1 , L 2 , L 3 , Ar 1 , Ar 2 are the same as those defined in Chemical Formula 1.
[0124] In one embodiment of the present invention, Ar 2 is represented by Chemical Formula 1b-1, L 2 is phenylene, and the bonding position of Ar 2 can be specified. For example, the organic compound of the present invention can be represented by Chemical Formula 1-5.
[0125] [Chemical Formula 1-5] TIFF2025078034000022.tif78170
[0126] In Chemical Formula 1-5, a1, a2, R 1 , R 2 , L 1 , L 3 , Ar 1 are the same as those defined in Chemical Formula 1, and R 4 , b4 are the same as those defined in Chemical Formula 1b-1.
[0127] In one embodiment of the present invention, Ar 2 is represented by Chemical Formula 1b-2, and L 2 may be a single bond. For example, the organic compound of the present invention may be represented by Chemical Formula 1-6.
[0128] [Chemical Formula 1-6] TIFF2025078034000023.tif106170
[0129] In Chemical Formula 1-6, a1, a2, R 1 , R 2 , L 1 , L 3 , Ar 1 are the same as those defined in Chemical Formula 1, and R 4 , R 5 , b4 are the same as those defined in Chemical Formula 1b-2.
[0130] The first compound 232, which is an organic compound of the present invention, may be one of the compounds of Chemical Formula 2.
[0131] [Chemical Formula 2] TIFF2025078034000024.tif233170TIFF2025078034000025.tif195170TIFF2025078034000026.tif237170TIFF2025078034000027.tif240170TIFF2025078034000028.tif222170TIFF2025078034000029.tif224170TIFF2025078034000030.tif226170TIFF2025078034000031.tif234170TIFF2025078034000032.tif236170TIFF2025078034000033.tif214170TIFF2025078034000034.tif194170TIFF2025078034000035.tif211170TIFF2025078034000036.tif225170TIFF2025078034000037.tif213170TIFF2025078034000038.tif208170TIFF2025078034000039.tif224170TIFF2025078034000040.tif246170TIFF2025078034000041.tif239170TIFF2025078034000042.tif174170
[0132] [Synthesis Example] 1. Synthesis of Compound A1 (1) Compound A [Reaction Scheme 1-1] TIFF2025078034000043.tif49170
[0133] In a one-neck round-bottom flask, 2,4,6-trichloro-1,3,5-triazine (10 g, 0.054 mol) was dissolved in 100 ml of THF, and then cooled to -78 °C under nitrogen conditions. Subsequently, 2.5 M n-BuLi solution (19 ml, 0.048 mol) was slowly added. After 30 minutes, carbazole (8.1 g, 0.048 mol) was further added. After warming to room temperature, the mixture was reacted for 3 hours. When the reaction was completed, the substance was completely precipitated using methanol, filtered, and then dissolved in MC. The column was advanced with hexane and methylene chloride (MC), and the obtained substance was concentrated. Then, impurities were removed using an acetone slurry and filtered to obtain Compound A. (12.7 g, 83%) (2) Compound C-1 [Reaction formula 1-2] TIFF2025078034000044.tif44170
[0134] In a one-neck round-bottom flask, 7-bromo-2-phenyl-1,3-benzothiazole (20 g, 0.072 mol), bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl 2 , 2.6 g, 0.0004 mol), potassium acetate (14.3 g, 0.14 mol), bis(pinacolato)diboron (B 2 (pin) 2 , 27.7 g, 0.11 mol) were dissolved in 250 ml of 1,4-dioxane and then refluxed for 3 hours. After the reaction solution was sufficiently cooled to room temperature, it was filtered, washed with MC, and concentrated. The concentrated substance was dissolved in MC and then filtered using MC and silica gel. After the filtered solution was concentrated, impurities were removed using a MeOH slurry and filtered to obtain Compound C-1. (21 g, 90%) (3) Compound A1-i [Reaction formula 1-3] TIFF2025078034000045.tif47170
[0135] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.032 mol), phenylboronic acid (3.5 g, 0.029 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0018 mol), and K2CO3 (8.77 g, 0.063 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture, and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, and the substance was completely precipitated and filtered. The precipitated substance was completely dissolved by heating with DCB (1,2-dichlorobenzene), and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain Compound A1-i. (6.2 g, 54%) (4) Compound A1 [Reaction Scheme 1-4] TIFF2025078034000046.tif44170
[0136] In a one-neck round-bottom flask, Compound A1-i (6.2 g, 0.017 mol), Compound C-1 (6.04 g, 0.018 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1 g, 0.0009 mol), and K2CO3 (4.7 g, 0.034 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB, and then filtered using chloroform and silica gel. The obtained solution was concentrated, impurities were removed using an acetone slurry, and filtration was performed to obtain Compound A1. (9.2 g, 80.6%) 2. Synthesis of Compound A5 (1) Compound A5-i [Reaction Scheme 2-1] TIFF2025078034000047.tif47170
[0137] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.032 mol), [1,1'-biphenyl]-4-ylboronic acid (5.6 g, 0.029 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0018 mol), and K2CO3 (8.77 g, 0.063 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture, and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, and the substance was completely precipitated and filtered. The precipitated substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain compound A5-i. (8.1 g, 59%) (2) Compound A5 [Reaction Formula 2-2] TIFF2025078034000048.tif43170
[0138] In a one-neck round-bottom flask, compound A5-i (8.1 g, 0.019 mol), compound C-1 (6.6 g, 0.021 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.1 g, 0.0010 mol), and K2CO3 (5.17 g, 0.037 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted while refluxing at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The obtained solution was concentrated, impurities were removed using an acetone slurry, and filtration was performed to obtain compound A5. (8.5 g, 76.8%) 3. Synthesis of Compound A6 (1) Compound A6-i [Reaction formula 3-1] TIFF2025078034000049.tif46170
[0139] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.032 mol), triphenylene-2-ylboronic acid (7.7 g, 0.029 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0018 mol), and K2CO3 (8.77 g, 0.063 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture, and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, and the substance was completely precipitated and filtered. The precipitated substance was completely dissolved by heating with DCB, and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain Compound A6-i. (9.2 g, 57%) (2) Compound A6 [Reaction formula 3-2] TIFF2025078034000050.tif43170
[0140] In a one-neck round-bottom flask, Compound A6-i (9.2 g, 0.018 mol), Compound C-1 (6.4 g, 0.020 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.0 g, 0.0009 mol), and K2CO3 (5.00 g, 0.036 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted with reflux at 110 °C for 2 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB, and then filtered using chloroform and silica gel. The obtained solution was concentrated, impurities were removed using an acetone slurry, and filtration was performed to obtain Compound A6. (10.2 g, 83.8%) 4. Synthesis of Compound A7 (1) Compound A7-i [Reaction Scheme 4-1] TIFF2025078034000051.tif47170
[0141] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.032 mol), (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (6.8 g, 0.029 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0018 mol), and K2CO3 (8.77 g, 0.063 mol) were dissolved in a mixture of tetrahydrofuran (100 mL) / water (20 mL), and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, and the substance was completely precipitated and filtered. The precipitated substance was completely dissolved by heating with DCB, and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was carried out to obtain Compound A7-i. (8.9 g, 59%) (2) Compound A7 [Reaction Scheme 4-2] TIFF2025078034000052.tif43170
[0142] In a one-neck round-bottom flask, compound A7-i (8.9 g, 0.019 mol), compound C-1 (6.6 g, 0.021 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.1 g, 0.0010 mol), and K2CO3 (5.17 g, 0.037 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The obtained solution was concentrated, impurities were removed using an acetone slurry, and filtration was performed to obtain compound A7. (7.5 g, 63.1%) Synthesis of Compound A8 (1) Compound A8-i [Reaction Scheme 5-1] TIFF2025078034000053.tif46170
[0143] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.032 mol), (9,9-diphenyl-fluoren-2-yl)boronic acid (10.3, 0.029 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0018 mol), and K2CO3 (8.77 g, 0.063 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture, and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, the substance was completely precipitated, and filtered. The precipitated substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain compound A8-i. (12.7 g, 67%) (2) Compound A8 [Reaction Scheme 5-2] TIFF2025078034000054.tif48170
[0144] In a one-neck round-bottom flask, compound A8-i (12.7, 0.021 mol), compound C-1 (7.5 g, 0.023 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.2 g, 0.0011 mol), and K2CO3 (5.9 g, 0.043 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The obtained solution was concentrated, impurities were removed using an acetone slurry, and filtration was performed to obtain compound A8. (13.0 g, 81.0%) 6. Synthesis of Compound A9 (1) Compound A9-i [Reaction Scheme 6-1] TIFF2025078034000055.tif48170
[0145] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10.1 g, 0.032 mol), naphthalene-2-ylboronic acid (5.0 g, 0.029 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0018 mol), and K2CO3 (8.76 g, 0.063 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture, and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, the substance was completely precipitated, and filtered. The precipitated substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain compound A9-i. (7.8 g, 66%) (2) Compound A9 [Reaction formula 6-2] TIFF2025078034000056.tif41170
[0146] In a one-neck round-bottom flask, compound A9-i (7.8 g, 0.021 mol), compound C-1 (7.5 g, 0.023 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.2 g, 0.0011 mol), and K2CO3 (6.0 g, 0.044 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The obtained solution was concentrated, impurities were removed using an acetone slurry, and compound A9 was obtained by filtration. (9.7 g, 81.0%) 7. Synthesis of compound A19 (1) Compound A19-i [Reaction formula 7-1] TIFF2025078034000057.tif46170
[0147] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.032 mol), dibenzofuran-4-ylboronic acid (6.0 g, 0.029 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0018 mol), and K2CO3 (8.77 g, 0.063 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture, and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, and the substance was completely precipitated and filtered. The precipitated substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain compound A19-i. (8.5 g, 60%) (2) Compound A19 [Reaction formula 7-2] TIFF2025078034000058.tif46170
[0148] In a one-neck round-bottom flask, compound A19-i (8.5 g, 0.019 mol), compound C-1 (6.7 g, 0.021 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.1 g, 0.0010 mol), and K2CO3 (5.26 g, 0.038 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted with reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The obtained solution was concentrated, impurities were removed using an acetone slurry, and filtration was performed to obtain compound A19. (8.8 g, 76.4%) 8. Synthesis of compound A29 (1) Compound C-2 [Reaction formula 8-1] TIFF2025078034000059.tif48170
[0149] In a one-neck round-bottom flask, 7-bromo-2-phenyl-1,3-benzothiazole (20 g, 0.072 mol), Pd(dppf)Cl 2 (2.6 g, 0.0004 mol), potassium acetate (14.3 g, 0.14 mol), B 2 (pin) 2 (27.7 g, 0.11 mol) was dissolved in 250 ml of 1,4-dioxane and then refluxed for 3 hours. After the reaction solution was sufficiently cooled to room temperature, it was filtered, washed with MC, and concentrated. The concentrated substance was dissolved in MC and then filtered using MC and silica gel. After the filtered solution was concentrated, impurities were removed using a MeOH slurry and filtered to obtain Compound C-2. (21 g, 90%) (2) Compound A29-i [Reaction Scheme 8-2] TIFF2025078034000060.tif52170
[0150] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.032 mol), [1,1'-biphenyl]-3-ylboronic acid (5.6 g, 0.029 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0018 mol), K2CO3 (8.77 g, 0.063 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, the substance was completely precipitated, and filtered. The precipitated substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtered to obtain Compound A29-i. (8.1 g, 65%) (3) Compound A29 [Reaction Scheme 8-3] TIFF2025078034000061.tif47170
[0151] In a one-neck round-bottom flask, compound A29-i (8.1 g, 0.019 mol), compound C-2 (6.29 g, 0.018 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1 g, 0.0009 mol), and K2CO3 (4.7 g, 0.034 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and washed thoroughly with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The resulting solution was concentrated, impurities were removed using an acetone slurry, and filtration was performed to obtain compound A29. (8.6 g, 80.6%) 9. Synthesis of Compound A30 [Reaction Scheme 9] TIFF2025078034000062.tif44170
[0152] In a one-neck round-bottom flask, compound A30-i (8.6 g, 0.017 mol), compound C-2 (6.29 g, 0.018 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1 g, 0.0009 mol), and K2CO3 (4.7 g, 0.034 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and washed thoroughly with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The resulting solution was concentrated, impurities were removed using an acetone slurry, and filtration was performed to obtain compound A30. (8.9 g, 79.0%) 10. Synthesis of Compound A105 (1) Compound C-3 [Reaction Scheme 10-1] TIFF2025078034000063.tif36170
[0153] In a one-neck round-bottom flask, 6-bromo-2-phenyl-1,3-benzoxazole (20 g, 0.072 mol), Pd(dppf)Cl 2 (2.6 g, 0.0004 mol), potassium acetate (14.3 g, 0.14 mol), B 2 (pin) 2 (27.7 g, 0.11 mol) was dissolved in 250 ml of 1,4-dioxane and then refluxed for 3 hours. After the reaction solution was sufficiently cooled to room temperature, it was filtered, washed with MC, and concentrated. The concentrated substance was dissolved in MC and then filtered using MC and silica gel. After the filtered solution was concentrated, impurities were removed using a MeOH slurry and then filtered to obtain compound C-3. (22 g, 94%) (2) Compound A105 [Reaction Scheme 10-2] TIFF2025078034000064.tif38170
[0154] In a one-neck round-bottom flask, compound A1-i (10.0 g, 0.028 mol), compound C-3 (9.9 g, 0.031 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.6 g, 0.0014 mol), and K2CO3 (7.8 g, 0.056 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and washed thoroughly with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The resulting solution was concentrated, impurities were removed using an acetone slurry, and then filtered to obtain compound A105. (11.1 g, 76.8%) 11. Synthesis of Compound A115 (1) Compound C-4 [Reaction Scheme 11-1] TIFF2025078034000065.tif37170
[0155] In a one-neck round-bottom flask, 5-bromo-2-phenyl-1,3-benzooxazole (20 g, 0.072 mol), Pd(dppf)Cl 2 (2.6 g, 0.0004 mol), potassium acetate (14.3 g, 0.14 mol), B 2 (pin) 2 (27.7 g, 0.11 mol) were dissolved in 250 ml of 1,4-dioxane and then refluxed for 3 hours. After the reaction solution was sufficiently cooled to room temperature, it was filtered, washed with MC, and concentrated. The concentrated substance was dissolved in MC and then filtered using MC, chloroform, and silica gel. After the filtered solution was concentrated, impurities were removed using a MeOH slurry and the compound C-4 was obtained by filtration. (22.2 g, 95%) (2) Compound A115 [Reaction Formula 11-2] TIFF2025078034000066.tif48170
[0156] In a one-neck round-bottom flask, compound A5-i (8.7 g, 0.019 mol), compound C-4 (7.45 g, 0.023 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.0 g, 0.0010 mol), K2CO3 (5.3 g, 0.038 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture and then reacted under reflux at 110 °C for 2 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and washed thoroughly with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The resulting solution was concentrated, impurities were removed using an acetone slurry, and compound A115 was obtained by filtration. (9.2 g, 72.6%) 12. Synthesis of Compound A128 (1) Compound C-5 [Reaction Formula 12-1] TIFF2025078034000067.tif50170
[0157] In a one-neck round-bottom flask, 6-bromo-2-phenyl-1,3-benzothiazole (20 g, 0.072 mol), Pd(dppf)Cl 2 (2.6 g, 0.0004 mol), potassium acetate (14.3 g, 0.14 mol), B 2 (pin) 2 (27.7 g, 0.11 mol) were dissolved in 250 ml of 1,4-dioxane, and then refluxed for 3 hours. After the reaction solution was sufficiently cooled to room temperature, it was filtered, washed with MC, and concentrated. The concentrated substance was dissolved in MC, and then filtered using MC, chloroform, and silica gel. After the filtered solution was concentrated, impurities were removed using a MeOH slurry, and the compound C-5 was obtained by filtration. (21 g, 92%) (2) Compound A128 [Reaction formula 12-2] TIFF2025078034000068.tif41170
[0158] In a one-neck round-bottom flask, compound A5-i (8.7 g, 0.019 mol), compound C-5 (7.45 g, 0.023 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.0 g, 0.0010 mol), K2CO3 (5.3 g, 0.038 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 5 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and washed thoroughly with water and methanol. The filtered substance was completely dissolved by heating with DCB, and then filtered using chloroform and silica gel. The resulting solution was concentrated, impurities were removed using an acetone slurry, and the compound A128 was obtained by filtration. (9.2 g, 72.6%) 13. Synthesis of compound A132 (1) Compound A132-i [Reaction Formula 13-1] TIFF2025078034000069.tif46170
[0159] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.032 mol), dibenzofuran-3-ylboronic acid (5.4 g, 0.025 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.8 g, 0.0016 mol), and K2CO3 (8.8 g, 0.064 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture, and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, and the substance was completely precipitated and filtered. The precipitated substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The filtered solution was concentrated, the impurities were removed using a methanol slurry, and the compound A132-i was obtained by filtration. (9.9 g, 70%) (2) Compound A132 [Reaction Formula 13-2] TIFF2025078034000070.tif45170
[0160] In a one-neck round-bottom flask, compound A132-i (9.9 g, 0.022 mol), compound C-5 (7.8 g, 0.024 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.3 g, 0.0011 mol), and K2CO3 (6.1 g, 0.044 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and washed thoroughly with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The obtained solution was concentrated, the impurities were removed using an acetone slurry, and the compound A132 was obtained by filtration. (9.2 g, 83.1%) 14. Synthesis of Compound A83 (1) Compound D-i [Reaction Formula 14-1] TIFF2025078034000071.tif50170
[0161] In a one-neck round-bottom flask, 1-bromo carbazole (25 g, 0.1 mol), phenylboronic acid (19 g, 0.153 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 5.9 g, 0.0050 mol), and K2CO3 (28.1 g, 0.044 mol) were dissolved in a 1,4-dioxane (300 mL) / water (1000 mL) mixture, and then reacted under reflux at 110 °C for 12 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved in MC and then filtered using silica gel. The obtained solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain Compound D-i. (21.4 g, 86.6%) (2) Compound D [Reaction Formula 14-2] TIFF2025078034000072.tif58170
[0162] In a one-neck round-bottom flask, 2,4,6-trichloro-1,3,5-triazine (20 g, 0.11 mol) was dissolved in 200 ml of THF and then cooled to -78 °C under a nitrogen atmosphere. Then, a 2.5 M n-BuLi solution (38 ml, 0.096 mol) was slowly added. After 30 minutes, 1-phenylcarbazole (21.4 g, 0.096 mol) was further added. After raising the temperature to room temperature, the mixture was reacted for 3 hours. When the reaction was completed, the substance was completely precipitated using methanol, filtered, and then dissolved in MC. The column was advanced using hexane and methylene chloride (MC), and the obtained substance was concentrated. Then, impurities were removed using an acetone slurry, and filtration was performed to obtain Compound D. (17.9 g, 54%) (3) Compound A83-i [Reaction Formula 14-3] TIFF2025078034000073.tif41170
[0163] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)-4-phenyl-carbazole (10 g, 0.026 mol), dibenzofuran-3-ylboronic acid (4.8 g, 0.022 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.5 g, 0.0013 mol), and K2CO3 (7.1 g, 0.051 mol) were dissolved in a mixture of tetrahydrofuran (100 mL) / water (20 mL), and then refluxed at 70 °C for 2 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, and the substance was completely precipitated and filtered. The precipitated substance was completely dissolved by heating with DCB, and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain Compound A83-i. (9.9 g, 70%) (4) Compound A83 [Reaction Formula 14-4] TIFF2025078034000074.tif42170
[0164] In a one-neck round-bottom flask, compound A83-i (10.0 g, 0.017 mol), compound C-1 (6.04 g, 0.018 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1 g, 0.0009 mol), and K2CO3 (4.7 g, 0.034 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The resulting solution was concentrated, impurities were removed using an acetone slurry, and compound A83 was obtained by filtration. (10.8 g, 82.9%) Synthesis of Compound A102 (1) Compound 102-ii [Reaction Scheme 15-1] TIFF2025078034000075.tif40170
[0165] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.026 mol), dibenzothiophen-3-ylboronic acid (4.4 g, 0.020 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.5 g, 0.0013 mol), and K2CO3 (7.07 g, 0.051 mol) were dissolved in a tetrahydrofuran (100 mL) / water (20 mL) mixture, and then refluxed at 70 °C for 3 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, the substance was completely precipitated, and then filtered. The precipitated substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and compound A102-ii was obtained by filtration. (8.8 g, 64%) (2) Compound 102-i [Reaction Scheme 15-2] TIFF2025078034000076.tif47170
[0166] In a one-neck round-bottom flask, compound A102-ii (8.8 g, 0.016 mol), 3-chlorophenylboronic acid (3.1 g, 0.020 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 0.9 g, 0.0008 mol), and K2CO3 (4.5 g, 0.032 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The obtained solution was concentrated, the impurities were removed using an acetone slurry, and filtration was performed to obtain compound A102-i. (8.1 g, 80.7%) (3) Compound 102 [Reaction Formula 15-3] TIFF2025078034000077.tif52170
[0167] In a one-neck round-bottom flask, compound A102-i (8.1 g, 0.013 mol), compound C-1 (4.7 g, 0.015 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 0.8 g, 0.0007 mol), and K2CO3 (3.6 g, 0.026 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 8 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered substance was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The obtained solution was concentrated, the impurities were removed using an acetone slurry, and filtration was performed to obtain compound A102. (8.5 g, 83.4%) 16. Synthesis of Compound 141 (1) Compound 141-ii [Reaction Formula 16-1] TIFF2025078034000078.tif39170
[0168] In a one-neck round-bottom flask, 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (10 g, 0.026 mol), [1,1'-biphenyl]-4-ylboronic acid (3.96 g, 0.020 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 1.5 g, 0.0013 mol), and K2CO3 (7.07 g, 0.051 mol) were dissolved in a mixture of tetrahydrofuran (100 mL) / water (20 mL), and then refluxed at 70 °C for 3 hours. After the reaction solution was cooled to room temperature, an excess amount of methanol was dispensed, and the substance was completely precipitated and filtered. The precipitated substance was completely dissolved by heating with DCB, and then filtered using chloroform and silica gel. The filtered solution was concentrated, impurities were removed using a methanol slurry, and filtration was performed to obtain compound A141-ii. (6.75 g, 67%) (2) Compound 141-i [Reaction Formula 16-2] TIFF2025078034000079.tif46170
[0169] In a one-neck round-bottom flask, compound A141-ii (6.75 g, 0.013 mol), 3-chlorophenylboronic acid (2.5 g, 0.016 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 0.9 g, 0.0008 mol), and K2CO3 (4.5 g, 0.032 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 4 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered material was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The resulting solution was concentrated, impurities were removed using an acetone slurry, and filtration was carried out to obtain compound A141-i. (6.2 g, 82.1%) (3) Compound 141 [Reaction Formula 16-3] TIFF2025078034000080.tif52170
[0170] In a one-neck round-bottom flask, compound A141-i (6.2 g, 0.0107 mol), compound C-5 (4.7 g, 0.015 mol), palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4, 0.8 g, 0.0007 mol), and K2CO3 (3.6 g, 0.026 mol) were dissolved in a 1,4-dioxane (100 mL) / water (20 mL) mixture, and then reacted under reflux at 110 °C for 8 hours. After the reaction solution was sufficiently cooled to room temperature, the precipitated solid was filtered and thoroughly washed with water and methanol. The filtered material was completely dissolved by heating with DCB and then filtered using chloroform and silica gel. The resulting solution was concentrated, impurities were removed using an acetone slurry, and filtration was carried out to obtain compound A141. (6.56 g, 82.9%) The light-emitting layer 230 may further contain a second compound 234 represented by Chemical Formula 3.
[0171] [Chemical Formula 3] TIFF2025078034000081.tif78170
[0172] In Chemical Formula 3, each of c1 and c4 is an integer from 0 to 4, and c2 and c3 are integers from 0 to 3. R 11 、R 12 、R 13 、R 14 Each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1 - C10 alkyl group, a substituted or unsubstituted C3 - C30 cycloalkyl group, a substituted or unsubstituted C1 - C10 alkoxy group, a substituted or unsubstituted C6 - C60 aryl group, and a substituted or unsubstituted C3 - C60 heteroaryl group. L 11 、L 12 Each is independently selected from the group consisting of a single bond, a substituted or unsubstituted C6 - C60 arylene group, and a substituted or unsubstituted C3 - C60 heteroarylene group. Ar 11 、Ar 12 Each is independently selected from the group consisting of a substituted or unsubstituted C6 - C30 aryl group and a substituted or unsubstituted C3 - C30 heteroaryl group.
[0173] In Chemical Formula 3, L 11 and L 12 are a single bond, and Ar 11 、Ar 12 Each may be a substituted or unsubstituted phenyl group. That is, Chemical Formula 3 may be represented by Chemical Formula 3a.
[0174] [Chemical Formula 3a] TIFF2025078034000082.tif94170
[0175] In Chemical Formula 3a, R 11 、R 12 、R 13 、R 14 、the definitions of c1, c2, c3, and c4 are the same as those defined in Chemical Formula 3. Ar 13 、Ar14 Each is a substituted or unsubstituted C6-C30 aryl group, c5 and c6 are each independently an integer from 0 to 5.
[0176] For example, in Chemical Formula 3a, Ar 13 and Ar 14 may each independently be phenyl, and c5 and c6 may each independently be 0 or 1.
[0177] The second compound 234 may be one of the compounds of Chemical Formula 4.
[0178] [Chemical Formula 4] TIFF2025078034000083.tif200170TIFF2025078034000084.tif130170
[0179] In the green pixel region, the light-emitting material layer 230 may further contain a third compound 236 selected from the compounds represented by Chemical Formula 5.
[0180] [Chemical Formula 5] TIFF2025078034000085.tif92170
[0181] In the yellow-green pixel region, the light-emitting material layer 230 may further contain a third compound 236 selected from the compounds represented by Chemical Formula 6.
[0182] [Chemical Formula 6] TIFF2025078034000086.tif93170
[0183] In the light-emitting material layer 230, the first compound 232 may be an n-type host (first host), the second compound 234 may be a p-type host (second host), and the third compound 236 may be a light emitter (dopant). The light-emitting material layer 230 may have a thickness of 50-600 Å, for example, 200-400 Å.
[0184] In the light-emitting material layer 230, the weight ratio of each of the first and second compounds 232 and 234 may be greater than the weight ratio of the third compound 236, and the first compound 232 and the second compound 234 may have the same or different weight ratios. In the light-emitting material layer 230, the weight ratio of the first compound 232 and the second compound 234 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the first compound 232 and the weight ratio of the second compound 234 may be the same. For example, the first compound 232 and the second compound 234 may have the same weight ratio, and the third compound 236 may have 5 to 25 wt% in the light-emitting material layer 230.
[0185] Further, the organic light-emitting layer 162 may further include an electron transport layer 240 (electron transporting layer, ETL) located between the light-emitting material layer 230 and the second electrode 164. For example, the electron transport layer 240 may be in contact with the light-emitting material layer 230. The electron transport layer 240 may have substantially the same thickness as the light-emitting material layer 230. For example, the electron transport layer 240 may have a thickness of 50 to 600 Å, for example, 200 to 400 Å.
[0186] The electron transport layer 240 may include at least one of the compound (first electron transport material) represented by Chemical Formula 7, the compound (second electron transport material) represented by Chemical Formula 8, and the compound (third electron transport material) represented by Chemical Formula 9.
[0187] [Chemical Formula 7] TIFF2025078034000087.tif59170
[0188] In Chemical Formula 7, L 21 is selected from the group consisting of a single bond, a substituted or unsubstituted C6 - C60 arylene group, and a substituted or unsubstituted C3 - C60 heteroarylene group, Ar 21 is represented by Chemical Formula 7a or Chemical Formula 7b, Ar 22 , Ar 23Each is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.
[0189] [Chemical formula 7a] TIFF2025078034000088.tif28170
[0190] [Chemical formula 7b] TIFF2025078034000089.tif36170
[0191] In Chemical formula 7a, d1 is an integer from 0 to 4, R 21 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group, R 22 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group, In Chemical formula 7b, d2 is an integer from 0 to 4, R 23 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group, R 24Each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.
[0192] In Chemical Formulas 7a and 7b, the "*" marked part is the bonding site.
[0193] In one embodiment of the present invention, Ar 22 , Ar 23 Each may independently be an unsubstituted or C1-C10 alkyl group (e.g., t-butyl) substituted C6-C60 aryl group (e.g., phenyl or naphthyl).
[0194] [Chemical Formula 8] TIFF2025078034000090.tif79170
[0195] In Chemical Formula 8, each of e1, e2, e3, and e4 is independently an integer from 0 to 4, and e5 is 0 or 1, R 31 , R 32 , R 33 , R 34 Each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group, X 1 , X 2 , X 3 Each is independently N or CR 35 , and at least two of X 1 , X 2 , X 3 are N, R 35Each is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group. Ar 31 , Ar 32 Each is independently selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group. L 31 is selected from the group consisting of a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group.
[0196] In one embodiment of the present invention, each of e1, e2, e3, and e4 may independently be 0 or 1.
[0197] In one embodiment of the present invention, R 31 , R 32 , R 33 , R 34 Each may independently be a substituted or unsubstituted C6-C30 aryl group (e.g., phenyl).
[0198] In one embodiment of the present invention, two of X 1 , X 2 , X 3 are N, and one of X 1 , X 2 , X 3 is CR 35 , and R 35 may be hydrogen.
[0199] In one embodiment of the present invention, Ar 31 , Ar 32 Each may independently be a substituted or unsubstituted C6-C30 aryl group (e.g., phenyl, biphenyl).
[0200] In one embodiment of the present invention, L 31may be a substituted or unsubstituted C6-C30 arylene group (e.g., phenylene).
[0201] [Chemical Formula 9] TIFF2025078034000091.tif68170
[0202] In Chemical Formula 9, each of f1, f2, and f3 is an integer from 0 to 4, and f4 is an integer from 0 to 3, R 41 、R 42 、R 43 、R 44 each is independently selected from the group consisting of a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group, X 11 is O, S, or NR 45 and R 45 is a substituted or unsubstituted C6-C30 aryl group, which is linked to an adjacent benzene ring to form a ring, X 12 、X 13 、X 14 each is independently N or CR 46 and at least two of X 12 、X 13 、X 14 are N, Ar 41 、Ar 42 、R 46 each is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group, L 41 is selected from the group consisting of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group.
[0203] In one embodiment of the present invention, each of f1, f2, f3, and f4 may be 0.
[0204] In one embodiment of the present invention, R 45 is a phenyl group and can form a carbazole structure by bonding to a nitrogen atom and an adjacent benzene ring.
[0205] In one embodiment of the present invention, L 41 may be a single bond or a substituted or unsubstituted C6-C30 arylene group (e.g., phenylene).
[0206] In one embodiment of the present invention, Ar 41 , Ar 42 each may be a substituted or unsubstituted C6-C30 aryl group (e.g., phenyl, naphthyl or naphthylphenyl).
[0207] In one embodiment of the present invention, R 46 may be hydrogen.
[0208] The first electron transport material of Chemical Formula 7 used in the electron transport material 282 may be one of the compounds represented by Chemical Formula 10.
[0209] [Chemical Formula 10] TIFF2025078034000092.tif213170
[0210] The second electron transport material of Chemical Formula 8 used in the electron transport material 282 may be one of the compounds represented by Chemical Formula 11.
[0211] [Chemical Formula 11] TIFF2025078034000093.tif115170
[0212] The third electron transport material of Chemical Formula 9 used in the electron transport material 282 may be one of the compounds represented by Chemical Formula 12.
[0213] [Chemical Formula 12] TIFF2025078034000094.tif226170TIFF2025078034000095.tif55170
[0214] The organic light-emitting layer 162 may further include a hole transporting layer (HTL) 220 located between the first electrode 160 and the light-emitting material layer 230. The thickness of the hole transporting layer 220 may be greater than the thicknesses of the light-emitting material layer 230 and the electron transporting layer 240, respectively. The hole transporting layer 220 may have a thickness of 800 to 1200 Å, for example, 900 to 1100 Å.
[0215] Further, the organic light-emitting layer 162 may further include at least one of a hole injection layer (HIL) 210 located between the first electrode 160 and the hole transporting layer 220 and an electron injection layer (EIL) 250 located between the second electrode 164 and the electron transporting layer 240.
[0216] Although not shown, the organic light-emitting layer 162 may further include at least one of an electron blocking layer (EBL) located between the hole transporting layer 220 and the light-emitting material layer 230 and a hole blocking layer (HBL) located between the light-emitting material layer 230 and the electron transporting layer 240.
[0217] The positive hole injection layer 210 may contain at least one compound among 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; NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2’3’-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile; HATCN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT / PSS), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine. The positive hole injection layer 210 may have a thickness of 10 to 100 Å, for example, 30 to 70 Å.
[0218] The positive hole transport layer 220 may contain at least one compound among N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine] (poly-TPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), 3,5-di(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-fluorene-2-amine, and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine.
[0219] The electron injection layer 250 may contain at least one among alkali metals such as Li, alkali halide substances such as LiF, CsF, NaF, BaF 2 and / or organometallic substances such as Liq, lithium benzoate, and sodium stearate. The electron injection layer 250 may have a thickness of 10 to 100 Å, for example, 30 to 70 Å.
[0220] The electron blocking layer may contain at least one of tris(4-carbazolyl-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-fluorene-2-amine, di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), 4,4’,4’’-tris(3-methylphenylamino)triphenylamine (MTDATA), 1,3-bis(carbazol-9-yl)benzene (mCP), 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-di(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), 2,8-bis(9-phenyl-9H-carbazol-3-yl)dibenzothiophene).
[0221] The hole blocking layer may contain at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1’-biphenyl-4-olato)aluminum (BAlq), tris-(8-hydroxyquinolinealuminum (Alq 3 ), 2-biphenyl-4-yl-5-(4-t-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’-bicarbazole, diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1).
[0222] As described above, in the organic light-emitting diode D located in at least one of the green pixel region and the yellow-green pixel region, the light-emitting material layer 230 contains a first compound 232 which is an organic compound of the present invention represented by Chemical Formula 1. Thereby, in the organic light-emitting diode D, the driving voltage is decreased and the light-emitting efficiency is increased.
[0223] Further, in the organic light-emitting diode D located in at least one of the green pixel region and the yellow-green pixel region, the light-emitting material layer 230 further contains a second compound 234 as a second host represented by Chemical Formula 3 together with the first compound 232 as the first host, and has great advantages in driving voltage and light-emitting efficiency.
[0224] Further, in the organic light-emitting diode D in the green pixel region, the light-emitting material layer 230 further contains, as a dopant, a third compound 236 which is one of the compounds represented by Chemical Formula 5 together with the first compound 232 as the first host and the second compound 234 as the second host, and has great advantages in driving voltage and light-emitting efficiency.
[0225] Further, in the organic light-emitting diode D in the yellow-green pixel region, the light-emitting material layer 230 further contains, as a dopant, a third compound 236 which is one of the compounds represented by Chemical Formula 6 together with the first compound 232 as the first host and the second compound 234 as the second host, and has great advantages in driving voltage and light-emitting efficiency.
[0226] Further, the organic light-emitting diode D located in at least one of the green pixel region and the yellow-green pixel region is located between the light-emitting material layer 230 and the second electrode 164 as a negative electrode, and further includes an electron transport layer 240 containing at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a third electron transport material represented by Chemical Formula 9, thereby having great advantages in driving voltage and light-emitting efficiency.
[0227] [Organic Light-Emitting Diode] On the positive electrode (ITO), a hole injection layer (compound of Chemical Formula 13, 50 Å), a hole transport layer (compound of Chemical Formula 14, 1000 Å), a green light-emitting material layer (first host, second host, dopant (compound GD1 of Chemical Formula 5), 15 wt%), 300 Å), an electron transport layer (compound ET2 of Chemical Formula 10, 300 Å), an electron injection layer (LiF, 50 Å), and a negative electrode (Al, 1000 Å) were sequentially laminated to fabricate an organic light-emitting diode.
[0228] [Chemical Formula 13] TIFF2025078034000096.tif39170
[0229] [Chemical Formula 14] TIFF2025078034000097.tif38170
[0230] 1. Comparative Example (1) Comparative Example 1 (Ref1) Using the compound CF1 of Chemical Formula 15 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (2) Comparative Example 2 (Ref2) Using the compound CF2 of Chemical Formula 15 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (3) Comparative Example 3 (Ref3) Using the compound CF3 of Chemical Formula 15 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (4) Comparative Example 4 (Ref4) Using the compound CF4 of Chemical Formula 15 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (5) Comparative Example 5 (Ref5) Using the compound CF5 of Chemical Formula 15 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (6) Comparative Example 6 (Ref6) Using the compound of Chemical Formula 15, CF6, as the first host and the compound of Chemical Formula 4, BCZ1, as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (7) Comparative Example 7 (Ref7) Using the compound of Chemical Formula 15, CF7, as the first host and the compound of Chemical Formula 4, BCZ1, as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) [Chemical Formula 15] TIFF2025078034000098.tif186170
[0231] 2. Experimental Examples (1) Experimental Example 1 (Ex1) Using the compound of Chemical Formula 2, A1, as the first host and the compound of Chemical Formula 4, BCZ1, as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (2) Experimental Example 2 (Ex2) Using the compound of Chemical Formula 2, A5, as the first host and the compound of Chemical Formula 4, BCZ1, as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (3) Experimental Example 3 (Ex3) Using the compound of Chemical Formula 2, A6, as the first host and the compound of Chemical Formula 4, BCZ1, as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (4) Experimental Example 4 (Ex4) Using the compound of Chemical Formula 2, A7, as the first host and the compound of Chemical Formula 4, BCZ1, as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (5) Experimental Example 5 (Ex5) Using the compound of Chemical Formula 2, A8, as the first host and the compound of Chemical Formula 4, BCZ1, as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (6) Experimental Example 6 (Ex6) Using the compound of Chemical Formula 2, A9, as the first host and the compound of Chemical Formula 4, BCZ1, as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (7) Experimental Example 7 (Ex7) Using the compound A19 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) (8) Experimental Example 8 (Ex8) Using the compound A29 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) (9) Experimental Example 9 (Ex9) Using the compound A30 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) (10) Experimental Example 10 (Ex10) Using the compound A49 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) (11) Experimental Example 11 (Ex11) Using the compound A63 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) (12) Experimental Example 12 (Ex12) Using the compound A83 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) (13) Experimental Example 13 (Ex13) Using the compound A102 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) (14) Experimental Example 14 (Ex14) Using the compound A105 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) (15) Experimental Example 15 (Ex15) Using the compound A115 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (16) Experimental Example 16 (Ex16) Using the compound A128 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (17) Experimental Example 17 (Ex17) Using the compound A132 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (18) Experimental Example 18 (Ex18) Using the compound A141 of Chemical Formula 2 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) (19) Experimental Examples 19 to 36 (Ex19 to Ex36) In Experimental Examples 1 to 18, the compound BCZ2 of Chemical Formula 4 was used instead of the compound BCZ1 of Chemical Formula 4 used as the second host.
[0232] The characteristics (driving voltage ΔV, luminous efficiency) of the organic light-emitting diodes of Comparative Example 1 and Comparative Example 7, and Experimental Examples 1 to 36 were measured and are shown in Tables 1 to 3.
[0233]
Table 1
[0234]
Table 2
[0235]
Table 3
[0236] As can be seen from Tables 1 to 3, compared with the organic light-emitting diodes of Comparative Examples 1 to 7, the organic light-emitting diodes of Experimental Examples 1 to 36 in which the green light-emitting material layer contains the organic compound of the present invention have advantages in driving voltage and luminous efficiency.
[0237] Also, as in Experimental Examples 15, 16, 18, 33, 34, and 36, when the organic compound of the present invention is represented by Chemical Formula 1-3 or Chemical Formula 1-4, and Ar 2 is Chemical Formula 1b-1, and L 1 is phenylene, and Ar 1 is phenyl, the driving voltage of the organic light-emitting diode decreases significantly, and the luminous efficiency increases significantly.
[0238] 3. Comparative Examples 8 to 19 (Ref8 to Ref19) Using each of the compounds CF8 to CF19 of Chemical Formula 16 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host: Second host = 1:1) [Chemical Formula 16] TIFF2025078034000102.tif208170TIFF2025078034000103.tif203170
[0239] The characteristics (driving voltage ΔV, luminous efficiency, lifespan) of the organic light-emitting diodes of Comparative Example 1, Comparative Example 8, Comparative Example 19, and Experimental Example 1 were measured and listed in Table 4.
[0240]
Table 4
[0241] As can be seen from Table 4, compared with the organic light-emitting diodes of Comparative Example 1 and Comparative Examples 8 to 19, the organic light-emitting diode of Experimental Example 1 in which the green light-emitting material layer contains the organic compound of the present invention has advantages in driving voltage, luminous efficiency, and lifespan.
[0242] For example, each of Compounds CF8 to CF19 used in Comparative Examples 8 to 19 and Compound A1 of the present invention has a difference only in the substituent at the benzoxazole terminal, but the light emission characteristics are greatly improved in the organic light emitting diode of Example 1 using Compound A1 of the present invention in which a phenyl group is bonded to the benzoxazole terminal.
[0243] 4. Comparative Examples 20 to 31 (Ref20 to Ref31) Using each of Compounds CF20 to CF31 of Chemical Formula 17 as the first host and Compound BCZ1 of Chemical Formula 4 as the second host, a green light emitting material layer was formed. (First host: Second host = 1:1) [Chemical Formula 17] TIFF2025078034000105.tif221170TIFF2025078034000106.tif195170TIFF2025078034000107.tif81170
[0244] The characteristics (driving voltage ΔV, luminous efficiency, lifetime) of the organic light emitting diodes of Comparative Example 1, Comparative Examples 20 and 31, and Experimental Example 11 were measured and are shown in Table 5.
[0245]
Table 5
[0246] As can be seen from Table 5, compared with the organic light emitting diodes of Comparative Example 1 and Comparative Examples 20 to 31, the organic light emitting diode of Experimental Example 11 in which the green light emitting material layer contains the organic compound of the present invention has advantages in driving voltage, luminous efficiency, and lifetime.
[0247] For example, each of Compounds CF20 to CF31 used in Comparative Examples 20 to 31 and Compound A63 of the present invention has a difference only in the substituent at the benzoxazole terminal, but the light emission characteristics are greatly improved in the organic light emitting diode of Experimental Example 11 using Compound A63 of the present invention in which a phenyl group is bonded to the benzoxazole terminal.
[0248] 5. Comparative Examples 32 to 37 (Ref32 to Ref37) Using each of the compounds CF32 to CF37 of Chemical Formula 18 as the first host and the compound BCZ1 of Chemical Formula 4 as the second host, a green light-emitting material layer was formed. (First host:Second host = 1:1) [Chemical Formula 18] TIFF2025078034000109.tif179170
[0249] The characteristics (driving voltage ΔV, luminous efficiency, lifespan) of the organic light-emitting diodes of Comparative Example 1, Comparative Examples 32 and 37, and Experimental Example 11 were measured and are shown in Table 6.
[0250]
Table 6
[0251] As can be seen from Table 6, compared with the organic light-emitting diodes of Comparative Example 1 and Comparative Examples 32 to 37, the organic light-emitting diode of Experimental Example 11 in which the green light-emitting material layer contains the organic compound of the present invention has advantages in terms of driving voltage, luminous efficiency, and lifespan.
[0252] For example, the compound CF32 used in Comparative Example 32 and the compound A63 of the present invention have differences only in the bonding position of the carbazole moiety and the triazine moiety. However, in the organic light-emitting diode of Experimental Example 11 using the compound A63 of the present invention having a structure in which the triazine moiety is bonded to the 3-position of the carbazole moiety, the driving voltage is greatly reduced and the luminous efficiency is greatly improved.
[0253] Also, compared with Comparative Examples 33 to 37 using the compounds CF33 to CF37 in which the triazine moiety is bonded to the 2-position of the carbazole moiety and an aryl group having 10 or more carbon atoms is bonded to the benzoxazole terminal, in the organic light-emitting diode of Experimental Example 11 using the compound A63 of the present invention having a structure in which the triazine moiety is bonded to the 3-position of the carbazole moiety and a phenyl group is bonded to the benzoxazole terminal, the luminous efficiency and lifespan are greatly improved.
[0254] FIG. 4 is a schematic cross-sectional view of an organic light-emitting diode according to a third embodiment of the present invention.
[0255] As shown in FIG. 4, the organic light-emitting diode D includes first and second electrodes 160 and 164 facing each other, and an organic light-emitting layer 162 positioned between the first and second electrodes 160 and 164. The organic light-emitting layer 162 includes a first light-emitting portion 310 including a first light-emitting material layer 320 and a second light-emitting portion 330 including a second light-emitting material layer 340. The organic light-emitting layer 162 may further include a charge generation layer 350 positioned between the first light-emitting portion 310 and the second light-emitting portion 330.
[0256] The first electrode 160 is an anode for injecting holes and may be made of a conductive material having a high work function, such as ITO or IZO. The second electrode 164 is a cathode for injecting electrons and may be made of any one of conductive materials having a small work function, such as aluminum (Al), magnesium (Mg), or an aluminum-magnesium alloy (AlMg).
[0257] When the organic light-emitting diode D is a top emission type, the first electrode 160 further includes a reflective layer and serves as a reflective electrode. The second electrode 164 has a thin thickness and can serve as a transmissive electrode (semi-transmissive electrode). Alternatively, when the organic light-emitting diode D is a bottom emission type, the first electrode 160 can serve as a transmissive electrode, and the second electrode 164 can serve as a reflective electrode.
[0258] The charge generation layer 350 is positioned between the first and second light-emitting portions 310 and 330, and the first light-emitting portion 310, the charge generation layer 350, and the second light-emitting portion 330 are sequentially stacked on the first electrode 160. That is, the first light-emitting portion 310 is positioned between the first electrode 160 and the charge generation layer 350, and the second light-emitting portion 330 is positioned between the second electrode 164 and the charge generation layer 350.
[0259] The first light-emitting unit 310 may further include a first electron transport layer 316 positioned between the first light-emitting material layer 320 and the second light-emitting unit 330. For example, the first electron transport layer 316 may be positioned between the first light-emitting material layer 320 and the charge generation layer 350.
[0260] In addition, the first light-emitting unit 310 may further include at least one of an electron injection layer 312 positioned between the first light-emitting material layer 320 and the first electrode 160 and a first hole transport layer 314 positioned between the first light-emitting material layer 320 and the electron injection layer 312.
[0261] In addition, the first light-emitting unit 310 may include at least one of a first electron blocking layer (not shown) positioned between the first hole transport layer 314 and the first light-emitting material layer 320 and a first hole blocking layer (not shown) positioned between the first light-emitting material layer 320 and the first electron transport layer 316.
[0262] The second light-emitting unit 330 may further include a second electron transport layer 334 positioned between the second light-emitting material layer 340 and the second electrode 164.
[0263] In addition, the second light-emitting unit 330 may further include at least one of a second hole transport layer 332 positioned below the second light-emitting material layer 340 and an electron injection layer 336 positioned between the second electron transport layer 334 and the second electrode 164.
[0264] In addition, the second light-emitting unit 330 may include at least one of a second electron blocking layer (not shown) positioned between the second hole transport layer 332 and the second light-emitting material layer 340 and a second hole blocking layer (not shown) positioned between the second light-emitting material layer 340 and the second electron transport layer 334.
[0265] The charge generation layer 350 is positioned between the first light-emitting unit 310 and the second light-emitting unit 330. That is, the first light-emitting unit 310 and the second light-emitting unit 330 are connected by the charge generation layer 350. The charge generation layer 350 may be a PN junction charge generation layer in which an N-type charge generation layer 352 and a P-type charge generation layer 354 are joined.
[0266] The N-type charge generation layer 352 is located between the first electron blocking layer 318 and the second hole transport layer 332, and the P-type charge generation layer 354 is located between the N-type charge generation layer 352 and the second hole transport layer 332.
[0267] The N-type charge generation layer 352 may be an organic layer doped with an alkali metal such as Li, Na, K, Cs and / or an alkaline earth metal such as Mg, Sr, Ba, Ra. For example, the N-type charge generation layer 382 is composed of an N-type charge generating material containing a host which is an organic substance such as 4,7-diphenyl-1,10-phenanthroline (4,7-dipheny-1,10-phenanthroline; Bphen), MTDATA and a dopant which is an alkali metal or an alkaline earth metal, and the dopant can be doped at 0.01 to 30% by weight.
[0268] The P-type charge generation layer 354 may be composed of a P-type charge generating material containing an inorganic substance selected from the group consisting of tungsten oxide (WOx), molybdenum oxide (MoOx), beryllium oxide (Be2O3), vanadium oxide (V2O5) and combinations thereof, and an organic substance selected from the group consisting of NPD, HAT-CN, F4TCNQ, TPD, TNB, TCTA, N,N'-dioctyl-3,4,9,10-perylenedicarboximide (N,N'-dioctyl-3,4,9,10-perylenedicarboximide; PTCDI-C8) and combinations thereof.
[0269] The first light-emitting material layer 320 includes a first compound 322, a second compound 324, and a third compound 326, and the second green light-emitting material layer 340 includes a fourth compound 342, a fifth compound 344, and a sixth compound 346.
[0270] At least one of the first compound 322 and the fourth compound 342 is the organic compound of the present invention represented by Chemical Formula 1, and at least one of the second compound 324 and the fifth compound 344 is the compound represented by Chemical Formula 3.
[0271] The first light-emitting material layer 320 and the second light-emitting material layer 340 are a green light-emitting material layer or a yellow-green light-emitting material layer. That is, the organic light-emitting diode D is located in a green pixel region or a yellow-green pixel region.
[0272] In the green pixel region, each of the third compound 326 and the sixth compound 346 is selected from the compounds represented by Chemical Formula 5. In the yellow-green pixel region, each of the third compound 326 and the sixth compound 346 is selected from the compounds represented by Chemical Formula 5.
[0273] In the yellow-green pixel region, each of the third compound 326 and the sixth compound 346 is selected from the compounds represented by Chemical Formula 5. In the yellow-green pixel region, each of the third compound 326 and the sixth compound 346 is selected from the compounds represented by Chemical Formula 6.
[0274] In the first light-emitting material layer 320, the first compound 322 may be an n-type host (the first host), the second compound 324 may be a p-type host (the second host), and the third compound 326 may be a light emitter (a dopant). In the second light-emitting material layer 340, the fifth compound 352 may be an n-type host (the first host), the fifth compound 344 may be a p-type host (the second host), and the sixth compound 346 may be a light emitter (a dopant). Each of the first and second light-emitting material layers 320 and 340 may have a thickness of 50 to 600 Å.
[0275] When the first compound 322 and the fourth compound 342 are the organic compounds of the present invention represented by Chemical Formula 1, the first compound 322 and the fourth compound 342 may be the same as or different from each other. When the second compound 324 and the fifth compound 344 are the compounds represented by Chemical Formula 3, the second compound 324 and the fifth compound 344 may be the same as or different from each other. When the third compound 326 and the sixth compound 346 are the compounds of Chemical Formula 5, the third compound 326 and the sixth compound 346 may be the same as or different from each other. When the third compound 326 and the sixth compound 346 are the compounds of Chemical Formula 6, the third compound 326 and the sixth compound 346 may be the same as or different from each other.
[0276] In the first light-emitting material layer 320, the weight ratio of each of the first and second compounds 322 and 324 may be greater than the weight ratio of the third compound 326, and the first compound 322 and the second compound 324 may have the same or different weight ratios. In the first light-emitting material layer 320, the weight ratio of the first compound 322 to the second compound 324 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the first compound 322 and the weight ratio of the second compound 324 may be the same. For example, the first compound 322 and the second compound 324 may have the same weight ratio, and the third compound 326 may have 5 to 25 wt% in the first light-emitting material layer 320.
[0277] In the second light-emitting material layer 340, the weight ratio of each of the fourth and fifth compounds 342 and 344 may be greater than the weight ratio of the sixth compound 346, and the fourth compound 342 and the fifth compound 344 may have the same or different weight ratios. In the second light-emitting material layer 340, the weight ratio of the fourth compound 342 to the fifth compound 344 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the fourth compound 342 and the weight ratio of the fifth compound 344 may be the same. For example, the fourth compound 342 and the fifth compound 344 may have the same weight ratio, and the sixth compound 346 may have 5 to 25 wt% in the second light-emitting material layer 340.
[0278] Each of the first and second electron transport layers 316 and 324 may contain at least one of the first electron transport material represented by Chemical Formula 7, the second electron transport material represented by Chemical Formula 8, and the third electron transport material represented by Chemical Formula 9.
[0279] In the organic light-emitting diode D located in at least one of the green pixel region and the yellow-green pixel region, each of the first light-emitting material layer 320 and the second light-emitting material layer 340 contains the organic compound of the present invention represented by Chemical Formula 1. Thereby, in the organic light-emitting diode D, the driving voltage is decreased and the light-emitting efficiency is increased.
[0280] Further, each of the first light-emitting material layer 320 and the second light-emitting material layer 340 further includes a compound represented by Chemical Formula 3 as a second host together with a first host which is an organic compound of the present invention, and has great advantages in driving voltage and luminous efficiency.
[0281] Further, each of the first light-emitting material layer 320 and the second light-emitting material layer 340 further includes a light-emitting body (dopant) which is a compound represented by Chemical Formula 5 or Chemical Formula 6 together with a first host which is a compound of Chemical Formula 1 and a second host which is a compound of Chemical Formula 3, and has great advantages in driving voltage and luminous efficiency.
[0282] Further, in the organic light-emitting diode D located in at least one of the green pixel region and the yellow-green pixel region, at least one of the first electron transport layer 316 and the second electron transport layer 334 includes at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a third electron transport material represented by Chemical Formula 9, thereby having great advantages in driving voltage and luminous efficiency.
[0283] FIG. 5 is a schematic cross-sectional view of an organic light-emitting display device according to a fourth embodiment of the present invention.
[0284] As shown in FIG. 5, the organic light-emitting display device 400 includes a first substrate 410 in which a red pixel region RP, a green pixel region GP, and a blue pixel region BP are defined, a second substrate 470 facing the first substrate 410, an organic light-emitting diode D located between the first substrate 410 and the second substrate 470 and emitting white light, and a color filter layer 480 located between the organic light-emitting diode D and the second substrate 470.
[0285] Each of the first substrate 410 and the second substrate 470 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be any one of a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, and a polycarbonate (PC) substrate.
[0286] On the first substrate 410, a buffer layer 420 is formed, and on the buffer layer 420, thin film transistors Tr are formed corresponding to a red pixel region RP, a green pixel region GP, and a blue pixel region BP, respectively. The buffer layer 420 may be made of an inorganic insulating material such as silicon oxide or silicon nitride. Further, the buffer layer 420 may have a multilayer structure by including a first layer made of silicon oxide and a second layer made of silicon nitride. The buffer layer 420 may be omitted.
[0287] On the buffer layer 420, a semiconductor layer 422 is formed. The semiconductor layer 422 may be made of an oxide semiconductor material or may be made of polycrystalline silicon.
[0288] On top of the semiconductor layer 422, a gate insulating film 424 made of an insulating material is formed. The gate insulating film 424 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.
[0289] On top of the gate insulating film 424, a gate electrode 430 made of a conductive material such as metal is formed corresponding to the center of the semiconductor layer 422.
[0290] On top of the gate electrode 430, an interlayer insulating film 432 made of an insulating material is formed. The interlayer insulating film 432 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or may be formed of an organic insulating material such as benzocyclobutene or photo-acryl.
[0291] The interlayer insulating film 432 has first and second contact holes 434 and 436 that expose both sides of the semiconductor layer 422. The first and second contact holes 434 and 436 are located at a distance from the gate electrode 430 on both sides of the gate electrode 430.
[0292] On the interlayer insulating film 432, a source electrode 440 and a drain electrode 442 made of a conductive material such as metal are formed.
[0293] The source electrode 440 and the drain electrode 442 are spaced apart with the gate electrode 430 as the center, and are in contact with both sides of the semiconductor layer 422 through the first and second contact holes 434 and 436, respectively.
[0294] The semiconductor layer 422, the gate electrode 430, the source electrode 440, and the drain electrode 442 form the thin film transistor Tr, and the thin film transistor Tr functions as a driving element.
[0295] Although not shown in the figure, a gate wiring and a data wiring intersect each other to define a pixel region, and a switching element connected to the gate wiring and the data wiring is further formed. The switching element is connected to the thin film transistor Tr as a driving element.
[0296] Also, a power wiring is formed separated from or parallel to the data wiring, and a storage capacitor for maintaining the voltage of the gate electrode of the thin film transistor Tr as a driving element constant during one frame may be further configured.
[0297] A planarization layer 450 having a drain contact hole 452 exposing the drain electrode 442 of the thin film transistor Tr is formed to cover the thin film transistor Tr.
[0298] On the planarization layer 450, a first electrode 460 connected to the drain electrode 442 of the thin film transistor Tr through the drain contact hole 452 is separately formed for each pixel region. The first electrode 460 may be an anode, and may include a transparent conductive oxide layer made of a conductive material having a relatively large work function value, for example, a transparent conductive oxide (TCO).
[0299] For example, the transparent conductive oxide layer of the first electrode 460 may include at least one of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO), and aluminum:zinc oxide (Al:ZnO; AZO).
[0300] The first electrode 460 may further include a reflective layer. For example, the reflective layer may be made of silver (Ag) or an aluminum-palladium-copper (aluminum-palladium-copper: APC) alloy. In the top-emission type organic light-emitting display device 400, the first electrode 460 may have a triple-layer structure of ITO / Ag / ITO or ITO / APC / ITO.
[0301] On the planarization layer 450, a bank layer 466 covering the end portion of the first electrode 460 is formed. The bank layer 466 exposes the center of the first electrode 460 corresponding to the red pixel region RP, the green pixel region GP, and the blue pixel region BP. Since the organic light-emitting diode D emits white light in the red pixel region RP, the green pixel region GP, and the blue pixel region BP, the light-emitting layer 462 may be formed as a common layer without the need to be separated from the red pixel region RP, the green pixel region GP, and the blue pixel region BP. The bank layer 466 is formed to prevent current leakage at the end portion of the first electrode 460, and the bank layer 466 may be omitted.
[0302] An organic light-emitting layer 462 is formed on the first electrode 460.
[0303] In one embodiment of the present invention, the organic light-emitting layer 462 may have a three-stack structure by including a first light-emitting portion including a green light-emitting material layer and a yellow-green light-emitting material layer, and second and third light-emitting portions each including a blue light-emitting material layer.
[0304] In one embodiment of the present invention, the organic light-emitting layer 462 may have a two-stack structure by including a second light-emitting portion including a green light-emitting material layer or a yellow-green light-emitting material layer, and a second light-emitting portion including a blue light-emitting material layer.
[0305] At this time, at least one of the green light-emitting material layer and the yellow-green light-emitting material layer contains the organic compound of the present invention.
[0306] A second electrode 464 is formed on the upper portion of the first substrate 410 on which the organic light-emitting layer 462 is formed.
[0307] In the organic light-emitting display device 400 of the present invention, since the light emitted from the organic light-emitting layer 462 enters the color filter layer 480 through the second electrode 464, the second electrode 464 has a thin thickness so that light can pass through.
[0308] The first electrode 460, the organic light-emitting layer 462, and the second electrode 464 form an organic light-emitting diode D.
[0309] The color filter layer 480 is located above the organic light-emitting diode D and includes a red color filter pattern 482, a green color filter pattern 484, and a blue color filter pattern 486 corresponding to a red pixel region RP, a green pixel region GP, and a blue pixel region BP, respectively. The red color filter pattern 482 includes at least one of a red dye and a red pigment, the green color filter pattern 484 includes at least one of a green dye and a green pigment, and the blue color filter pattern 485 may include at least one of a blue dye and a blue pigment.
[0310] Although not shown, the color filter layer 480 may be attached to the organic light-emitting diode D by an adhesive layer. Alternatively, the color filter layer 480 may be formed directly above the organic light-emitting diode D.
[0311] Although not shown, an encapsulation film may be formed to prevent external moisture from penetrating into the organic light-emitting diode D. For example, the encapsulation film may have a laminated structure of a first inorganic insulating layer, an organic insulating layer, and a second inorganic insulating layer, but is not limited thereto.
[0312] Also, a polarizing plate for reducing external light reflection may be attached to the outer surface of the second substrate 470. For example, the polarizing plate may be a circular polarizing plate.
[0313] In the organic light-emitting display device 400 of FIG. 5, the first electrode 460 is a reflective electrode, the second electrode 464 is a transmissive (semi-transmissive) electrode, and the color filter layer 480 is disposed above the organic light-emitting diode D. Alternatively, the first electrode 460 may be a transmissive (semi-transmissive) electrode, and the second electrode 464 may be a reflective electrode. In this case, the color filter layer 480 may be disposed between the organic light-emitting diode D and the first substrate 410.
[0314] Also, a color conversion layer (not shown) may be provided between the organic light-emitting diode D and the color filter layer 480. The color conversion layer includes a red color conversion layer, a green color conversion layer, and a blue color conversion layer corresponding to each pixel region, and can convert white light from the organic light-emitting diode D into red, green, and blue, respectively. For example, the color conversion layer may include quantum dots. Therefore, the color purity of the organic light-emitting display device 400 can be further improved.
[0315] Also, a color conversion layer may be included instead of the color filter layer 480.
[0316] As described above, in the organic light-emitting display device 400, the organic light-emitting diodes D in the red pixel region RP, the green pixel region GP, and the blue pixel region BP emit white light, and the light from the organic light-emitting diodes D passes through the red color filter pattern 482, the green color filter pattern 484, and the blue color filter pattern 486, so that green, red, and blue are respectively displayed in the red pixel region RP, the green pixel region GP, and the blue pixel region BP.
[0317] Note that in FIG. 5, an organic light-emitting diode D that emits white light is used in the display device. Alternatively, the organic light-emitting diode D may be formed on the front surface of the substrate without a driving element such as a thin-film transistor Tr and a color filter layer 480, and may be used in an illumination device. In the present invention, the organic light-emitting device includes a display device and an illumination device.
[0318] FIG. 6 is a schematic cross-sectional view of an organic light-emitting diode according to the fifth embodiment of the present invention.
[0319] Referring to FIG. 6, the organic light-emitting layer 462 includes a first light-emitting portion 530 including a green light-emitting material layer 510a, a second light-emitting portion 540 including a first blue light-emitting material layer 550, and a third light-emitting portion 560 including a second blue light-emitting material layer 570. Further, the organic light-emitting layer 462 may further include a first charge generation layer 580 located between the first light-emitting portion 530 and the second light-emitting portion 540, and a second charge generation layer 590 located between the first light-emitting portion 530 and the third light-emitting portion 560. Further, the first light-emitting portion 530 may further include a red light-emitting material layer 510b.
[0320] The second light-emitting portion 540 is located between the first electrode 460 and the first light-emitting portion 530, and the third light-emitting portion 560 is located between the first light-emitting portion 530 and the second electrode 464. Further, the second light-emitting portion 540 is located between the first electrode 460 and the first charge generation layer 580, and the third light-emitting portion 560 is located between the second charge generation layer 590 and the second electrode 464. That is, the second light-emitting portion 540, the first charge generation layer 580, the first light-emitting portion 530, the second charge generation layer 590, and the third light-emitting portion 560 are sequentially stacked on the first electrode 460.
[0321] In the first light-emitting part 530, the red light-emitting material layer 510b may be located below the green light-emitting material layer 510a.
[0322] The first light-emitting part 530 may further include a first electron transport layer 534 located above the green light-emitting material layer 510a. Also, the first light-emitting part 530 may further include a first hole transport layer 532 located below the red light-emitting material layer 510b.
[0323] For example, in the first light-emitting part 530, the red light-emitting material layer 510b may be located between the first hole transport layer 532 and the green light-emitting material layer 510a, and the green light-emitting material layer 510a may be located between the red light-emitting material layer 510b and the first electron transport layer 534.
[0324] The second light-emitting part 540 may further include at least one of a second hole transport layer 544 located below the first blue light-emitting material layer 550 and a second electron transport layer 546 located above the first blue light-emitting material layer 550. Also, the second light-emitting part 540 may further include a hole injection layer 542 located between the first electrode 460 and the second hole transport layer 544.
[0325] Also, the second light-emitting part 540 may further include at least one of a first electron blocking layer (not shown) located between the second hole transport layer 544 and the first blue light-emitting material layer 550 and a first hole blocking layer (not shown) located between the second electron transport layer 546 and the first blue light-emitting material layer 550.
[0326] The third light-emitting part 560 may further include at least one of a third hole transport layer 562 located below the second blue light-emitting material layer 570 and a third electron transport layer 564 located above the second blue light-emitting material layer 570. Also, the third light-emitting part 560 may further include an electron injection layer 566 located between the second electrode 460 and the third electron transport layer 564.
[0327] Further, the third light-emitting unit 560 may further include at least one of a second electron blocking layer (not shown) located between the third hole transport layer 562 and the second blue light-emitting material layer 570 and a second hole blocking layer (not shown) located between the third electron transport layer 564 and the second blue light-emitting material layer 570.
[0328] The green light-emitting material layer 510a includes a first compound 512 which is an organic compound of the present invention represented by Chemical Formula 1. Further, the green light-emitting material layer 510a may further include a second compound 514 represented by Chemical Formula 3. Further, the green light-emitting material layer 510a may further include a third compound 516 selected from the compounds of Chemical Formula 5.
[0329] In the green light-emitting material layer 510a, the first compound 512 may be an n-type host (first host), the second compound 514 may be a p-type host (second host), and the third compound 516 may be a light emitter (dopant). The green light-emitting material layer 510a may have a thickness of 50 to 600 Å.
[0330] In the green light-emitting material layer 510a, the weight ratio of each of the first and second compounds 512 and 514 may be greater than the weight ratio of the third compound 516, and the first compound 512 and the second compound 514 may have the same or different weight ratios. In the green light-emitting material layer 510a, the weight ratio of the first compound 512 and the second compound 514 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the first compound 512 and the weight ratio of the second compound 514 may be the same. For example, the first compound 512 and the second compound 514 may have the same weight ratio, and the third compound 516 may have 5 to 25 wt% in the green light-emitting material layer 510a.
[0331] Each of the first to third electron transport layers 534, 546, and 564 may include at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a third electron transport material represented by Chemical Formula 9.
[0332] The red light-emitting material layer 510b may contain a red host and a red dopant. The red dopant may contain at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescence compound. In the red light-emitting material layer 510b, the red host may have a weight ratio larger than that of the red dopant. In the red light-emitting material layer 510b, the red dopant may be doped at a content of 1 to 10 wt%, for example, 1 to 5 wt%.
[0333] For example, the red host includes 9,9’-diphenyl-9H,9’H-3,3’-bicarbazole (BCzPh), CBP, 1,3,5-tris(carbazole-9-yl)benzene (TCP), TCTA, 4,4’-bis(carbazole-9-yl)-2,2’-dimethylbiphenyl (CDBP), 2,7-bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2’,7,7’-tetrakis(carbazole-9-yl)-9,9-spirofluorene (Spior-CBP), DPEPO, 4’-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (PCzB-2CN), 3’-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (mCzB-2CN), 3,6-bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCz1), bis(2-(2-hydroxyphenyl)-pyridine)beryllium (Bepp 2 ), bis(10-hydroxylbenzo[h]quinolinato)beryllium (Bebq 2) It can be selected from the group consisting of 1,3,5-tris(1-pyrenyl)benzene (1,3,5-Tris(1-pyrenyl)benzene; TPB3). However, it is not limited thereto.
[0334] In addition, the red dopant is [bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptane-3,5-dionate) iridium(III) ([Bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptane-3,5-dionate)iridium(III), bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate) iridium(III) (Bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III); Hex-Ir(phq) 2 (acac)), tris[2-(4-n-hexylphenyl)quinoline]iridium(III) (Tris[2-(4-n-hexylphenyl)quinoline]iridium(III), Hex-Ir(phq) 3 ) tris[2-phenyl-4-methylquinoline]iridium(III) (Tris[2-phenyl-4-methylquinoline]iridium(III), Ir(Mphq) 3 ) bis(2-phenylquinoline)(2,2,6,6-tetramethylheptene-3,5-dionate) iridium(III) (Bis(2-phenylquinoline)(2,2,6,6-tetramethylheptene-3,5-dionate)iridium(III), Ir(dpm)PQ 2 ) bis(phenylisoquinoline)(2,2,6,6-tetramethylheptene-3,5-dionate) iridium(III) (Bis(phenylisoquinoline)(2,2,6,6-tetramethylheptene-3,5-dionate)iridium(III), Ir(dpm)(piq) 2) Bis[(4-n-hexylphenyl)isoquinoline](acetylacetonate)iridium(III); Hex-Ir(piq) 2 (acac)), Tris[2-(4-n-hexylphenyl)quinoline]iridium(III), Hex-Ir(piq) 3 ) Tris(2-(3-methylphenyl)-7-methyl-quinolato)iridium; Ir(dmpq) 3 ) Bis[2-(2-methylphenyl)-7-methyl-quinoline](acetylacetonate)iridium(III); Ir(dmpq) 2 (acac)), Bis[2-(3,5-dimethylphenyl)-4-methyl-quinoline](acetylacetonate)iridium(III); Ir(mphmq) 2 (acac)) can be selected from the group consisting of, but is not limited to,
[0335] The first blue light-emitting material layer 550 of the second light-emitting unit 540 includes a first blue host and a first blue dopant, and the second blue light-emitting material layer 570 of the third light-emitting unit 560 includes a second blue host and a second blue dopant.
[0336] The first and second blue dopants may each contain at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. In the first blue light-emitting material layer 550, the first blue host may have a weight ratio greater than that of the first blue dopant. In the second blue light-emitting material layer 570, the second blue host may have a weight ratio greater than that of the second blue dopant. In each of the first and second blue light-emitting material layers 550 and 570, the first and second blue dopants may be doped at a content of 1 to 10 wt%, for example, 1 to 5 wt%.
[0337] For example, each of the first and second blue hosts can be selected from the group consisting of mCP, 9-(3-(9H-carbazol-9-yl)phenyl)-9H-carbazole-3-carbonitrile (mCP-CN), mCBP, CBP-CN, 9-(3-(9H-carbazol-9-yl)phenyl)-3-(diphenylphosphoryl)-9H-carbazole (mCPPO1), 3,5-di(9H-carbazol-9-yl)biphenyl (Ph-mCP), TSPO1, 9-(3’-(9H-carbazol-9-yl)-[1,1’-biphenyl]-3-yl)-9H-pyrido[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-spirobifluorene-2-yl-diphenyl-phosphine oxide (SPPO1), 9,9’-(5-(triphenylsilyl)-1,3-phenylene)bis(9H-carbazole) (SimCP). However, it is not limited thereto.
[0338] Each of the first and second blue dopants is independently selected from the group consisting of perylene, 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 4-(di-p-tolylamino)-4-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 2,7-bis(4-diphenylaminostyryl)-9,9-spirofluorene (spiro-DPVBi), [1,4-bis[2-[4-[N,N-di(p-tolyl)amino]phenyl]vinyl]benzene (DSB), 1-4-di-[4-(N,N-diphenyl)aminostyryl]-benzene (DSA), 2,5,8,11-tetra-tert-butylperylene; (TBPe), bis(2-hydroxyphenyl)-pyridine)beryllium (Bepp 2 ), 9-(9-phenylcarbazol-3-yl)-10-(naphthalen-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) 2 pic), tris(2-(4,6-difluorophenyl)pyridine))iridium(III) (Ir(Fppy) 3 ), bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III) (FIrpic), but is not limited thereto.
[0339] For example, each of the first and second blue light-emitting material layers 550, 570 may include a host that is an anthracene derivative and a dopant that is a boron derivative.
[0340] The first charge generation layer 580 is located between the first light-emitting part 530 and the second light-emitting part 540, and the second charge generation layer 590 is located between the first light-emitting part 530 and the third light-emitting part 560. That is, the first light-emitting part 530 and the second light-emitting part 540 are connected by the first charge generation layer 580, and the first light-emitting part 530 and the third light-emitting part 560 are connected by the second charge generation layer 590. The first charge generation layer 580 may be a PN junction charge generation layer in which an N-type charge generation layer 582 and a P-type charge generation layer 584 are joined, and the second charge generation layer 590 may be a PN junction charge generation layer in which an N-type charge generation layer 592 and a P-type charge generation layer 594 are joined.
[0341] The N-type charge generation layer 582 of the first charge generation layer 580 is located between the first hole transport layer 532 and the second electron transport layer 546, and the P-type charge generation layer 584 of the first charge generation layer 580 is located between the N-type charge generation layer 582 and the first hole transport layer 532.
[0342] The N-type charge generation layer 592 of the second charge generation layer 590 is located between the first electron transport layer 534 and the third hole transport layer 562, and the P-type charge generation layer 594 of the second charge generation layer 590 is located between the N-type charge generation layer 592 and the third hole transport layer 562.
[0343] Each of the first and second N-type charge generation layers 582, 592 may be made of the above-described N-type charge generating material, and each of the first and second P-type charge generation layers 584, 594 may be made of the above-described P-type charge generating material.
[0344] As described above, the organic light-emitting diode D of the present invention includes a first light-emitting part 530 including a green light-emitting material layer 510a and a red light-emitting material layer 510b, a second light-emitting part 540 including a first blue light-emitting material layer 550, and a third light-emitting part 560 including a second blue light-emitting material layer 570. The organic light-emitting diode D emits white light.
[0345] The green light-emitting material layer 510a contains the organic compound of the present invention represented by Chemical Formula 1. Thereby, in the organic light-emitting diode D, the driving voltage is decreased and the light-emitting efficiency is improved.
[0346] In addition, the green light-emitting material layer 510a further includes a compound represented by Chemical Formula 3 as a second host together with the first host which is an organic compound of the present invention, and has great advantages in driving voltage and luminous efficiency.
[0347] In addition, the green light-emitting material layer 510a further includes a light-emitting body (dopant) selected from the compounds of Chemical Formula 5 together with the first host which is the compound of Chemical Formula 1 and the second host which is the compound of Chemical Formula 3, and has great advantages in driving voltage and luminous efficiency.
[0348] In addition, at least one of the first to third electron transport layers 534, 546, 564 includes at least one of the first electron transport material represented by Chemical Formula 7, the second electron transport material represented by Chemical Formula 8, and the third electron transport material represented by Chemical Formula 9, thereby having great advantages in driving voltage and luminous efficiency.
[0349] FIG. 7 is a schematic cross-sectional view of an organic light-emitting diode according to a sixth embodiment of the present invention.
[0350] Referring to FIG. 7, the organic light-emitting layer 462 includes a first light-emitting portion 630 including a green light-emitting material layer 610a, a red light-emitting material layer 610b, and a yellow-green light-emitting material layer 610c, a second light-emitting portion 640 including a first blue light-emitting material layer 650, and a third light-emitting portion 660 including a second blue light-emitting material layer 670. In addition, the organic light-emitting layer 462 may further include a first charge generation layer 680 located between the first light-emitting portion 630 and the second light-emitting portion 640, and a second charge generation layer 690 located between the first light-emitting portion 630 and the third light-emitting portion 660.
[0351] The second light-emitting portion 640 is located between the first electrode 460 and the first light-emitting portion 630, and the third light-emitting portion 660 is located between the first light-emitting portion 630 and the second electrode 464. In addition, the second light-emitting portion 640 is located between the first electrode 460 and the first charge generation layer 680, and the third light-emitting portion 660 is located between the second charge generation layer 690 and the second electrode 464. That is, the second light-emitting portion 640, the first charge generation layer 680, the first light-emitting portion 630, the second charge generation layer 690, and the third light-emitting portion 660 are sequentially stacked on the first electrode 460.
[0352] In the first light-emitting part 630, the red light-emitting material layer 610b is located below the yellow-green light-emitting material layer 610c, and the green light-emitting material layer 610a is located above the yellow-green light-emitting material layer 610c. That is, in the organic light-emitting diode D of FIG. 6, the first light-emitting part 530 includes the double-layer light-emitting material layers 510a and 510b, while in the organic light-emitting diode D of FIG. 7, the first light-emitting part 630 includes the triple-layer light-emitting material layers 610a, 610b, and 610c.
[0353] The first light-emitting part 630 may further include a first electron transport layer 634 located above the green light-emitting material layer 610a. Also, the first light-emitting part 630 may further include a first hole transport layer 632 located below the red light-emitting material layer 610b.
[0354] For example, in the first light-emitting part 630, the red light-emitting material layer 610b may be located between the first hole transport layer 632 and the yellow-green light-emitting material layer 610c, and the green light-emitting material layer 610a may be located between the yellow-green light-emitting material layer 610c and the first electron transport layer 634.
[0355] The second light-emitting part 640 may further include at least one of a second hole transport layer 644 located below the first blue light-emitting material layer 650 and a second electron transport layer 648 located above the first blue light-emitting material layer 650. Also, the second light-emitting part 640 may further include a hole injection layer 642 located between the first electrode 460 and the second hole transport layer 644.
[0356] Also, the second light-emitting part 640 may further include at least one of a first electron blocking layer (not shown) located between the second hole transport layer 644 and the first blue light-emitting material layer 650 and a first hole blocking layer (not shown) located between the second electron transport layer 646 and the first blue light-emitting material layer 650.
[0357] The third light-emitting part 660 may further include at least one of a third hole transport layer 662 located below the second blue light-emitting material layer 670 and a third electron transport layer 666 located above the second blue light-emitting material layer 670. Further, the third light-emitting part 660 may further include an electron injection layer 668 located between the second electrode 460 and the third electron transport layer 666.
[0358] Further, the third light-emitting part 660 may further include at least one of a second electron blocking layer (not shown) located between the third hole transport layer 662 and the second blue light-emitting material layer 670 and a second hole blocking layer (not shown) located between the third electron transport layer 664 and the second blue light-emitting material layer 670.
[0359] The green light-emitting material layer 610a includes a first compound 612 which is an organic compound of the present invention represented by Chemical Formula 1. Further, the green light-emitting material layer 610a may further include a second compound 614 represented by Chemical Formula 3. Further, the green light-emitting material layer 610a may further include a third compound 616 which is one of the compounds of Chemical Formula 5.
[0360] In the green light-emitting material layer 610a, the first compound 612 may be an n-type host (first host), the second compound 614 may be a p-type host (second host), and the third compound 616 may be a light emitter (dopant). The green light-emitting material layer 610a may have a thickness of 50 to 600 Å.
[0361] In the green light-emitting material layer 610a, the weight ratio of each of the first and second compounds 612 and 614 may be greater than the weight ratio of the third compound 616, and the first compound 612 and the second compound 614 may have the same or different weight ratios. In the green light-emitting material layer 610a, the weight ratio of the first compound 612 and the second compound 614 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the first compound 612 and the weight ratio of the second compound 614 may be the same. For example, the first compound 612 and the second compound 614 may have the same weight ratio, and the third compound 616 may have 5 to 25 wt% in the green light-emitting material layer 610a.
[0362] The yellow-green light-emitting material layer 610c contains a first compound 622 which is an organic compound of the present invention represented by Chemical Formula 1. Further, the yellow-green light-emitting material layer 610c may further contain a second compound 624 represented by Chemical Formula 3. Further, the yellow-green light-emitting material layer 610c may further contain a third compound 626 which is one of the compounds of Chemical Formula 6.
[0363] In the yellow-green light-emitting material layer 610c, the first compound 622 may be an n-type host (first host), the second compound 624 may be a p-type host (second host), and the third compound 626 may be a light emitter (dopant). The yellow-green light-emitting material layer 610c may have a thickness of 50 to 600 Å.
[0364] In the yellow-green light-emitting material layer 610c, the weight ratio of each of the first and second compounds 622 and 624 may be greater than the weight ratio of the third compound 626, and the first compound 622 and the second compound 624 may have the same or different weight ratios. In the yellow-green light-emitting material layer 610c, the weight ratio of the first compound 622 and the second compound 624 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the first compound 622 and the weight ratio of the second compound 624 may be the same. For example, the first compound 622 and the second compound 624 may have the same weight ratio, and the third compound 626 may have 5 to 25 wt% in the yellow-green light-emitting material layer 610c.
[0365] Each of the first to third electron transport layers 634, 646, and 664 may contain at least one of the first electron transport material represented by Chemical Formula 7, the second electron transport material represented by Chemical Formula 8, and the fourth electron transport material represented by Chemical Formula 9.
[0366] The red light-emitting material layer 610b may contain a red host and a red dopant. The red dopant may contain at least one of a red phosphorescent compound, a red fluorescent compound, and a red delayed fluorescent compound. The red host may be the red host material described above, and the red dopant may be the red dopant material described above.
[0367] In the red light-emitting material layer 610b, the red host may have a weight ratio larger than that of the red dopant. In the red light-emitting material layer 610b, the red dopant may be doped at a content of 1 to 10 wt%, for example, 1 to 5 wt%.
[0368] The first blue light-emitting material layer 650 of the second light-emitting unit 640 contains a first blue host and a first blue dopant, and the second blue light-emitting material layer 670 of the third light-emitting unit 660 contains a second blue host and a second blue dopant.
[0369] The first and second blue dopants may each contain at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. Each of the first and second blue hosts may be the blue host material described above, and each of the first and second blue dopants may be the blue dopant material described above.
[0370] In the first blue light-emitting material layer 650, the first blue host may have a weight ratio larger than that of the first blue dopant. In the second blue light-emitting material layer 670, the second blue host may have a weight ratio larger than that of the second blue dopant. In each of the first and second blue light-emitting material layers 650 and 670, the first and second blue dopants may be doped at a content of 1 to 10 wt%, for example, 1 to 5 wt%.
[0371] The first charge generation layer 680 is located between the first light emitting part 630 and the second light emitting part 640, and the second charge generation layer 690 is located between the first light emitting part 630 and the third light emitting part 660. That is, the first light emitting part 630 and the second light emitting part 640 are connected by the first charge generation layer 680, and the first light emitting part 630 and the third light emitting part 660 are connected by the second charge generation layer 690. The first charge generation layer 680 may be a PN junction charge generation layer in which an N-type charge generation layer 682 and a P-type charge generation layer 684 are joined, and the second charge generation layer 690 may be a PN junction charge generation layer in which an N-type charge generation layer 692 and a P-type charge generation layer 694 are joined.
[0372] The N-type charge generation layer 682 of the first charge generation layer 680 is located between the first hole transport layer 632 and the second electron transport layer 646, and the P-type charge generation layer 684 of the first charge generation layer 680 is located between the N-type charge generation layer 682 and the first hole transport layer 632.
[0373] The N-type charge generation layer 692 of the second charge generation layer 690 is located between the first electron transport layer 634 and the third hole transport layer 662, and the P-type charge generation layer 694 of the second charge generation layer 690 is located between the N-type charge generation layer 692 and the third hole transport layer 662.
[0374] As described above, the organic light emitting diode D of the present invention includes a first light emitting part 630 including a green light emitting material layer 610a, a red light emitting material layer 610b, and a yellow-green light emitting material layer 610c, a second light emitting part 640 including a first blue light emitting material layer 650, and a third light emitting part 660 including a second blue light emitting material layer 670, and the organic light emitting diode D emits white light.
[0375] At least one of the color light emitting material layer 610a and the yellow-green light emitting material layer 610c contains the organic compound of the present invention represented by Chemical Formula 1. Thereby, in the organic light emitting diode D, the driving voltage decreases and the light emitting efficiency increases.
[0376] Further, at least one of the green light-emitting material layer 610a and the yellow-green light-emitting material layer 610c further includes a compound represented by Chemical Formula 3 as a second host together with a first host which is an organic compound of the present invention, and has great advantages in driving voltage and luminous efficiency.
[0377] Further, the green light-emitting material layer 610a further includes a light-emitting body (dopant) which is one of the compounds represented by Chemical Formula 5 together with a first host which is a compound represented by Chemical Formula 1 and a second host which is a compound represented by Chemical Formula 3, and has great advantages in driving voltage and luminous efficiency.
[0378] Further, the yellow-green light-emitting material layer 610c further includes a light-emitting body (dopant) which is one of the compounds represented by Chemical Formula 6 together with a first host which is a compound represented by Chemical Formula 1 and a second host which is a compound represented by Chemical Formula 3, and has great advantages in driving voltage and luminous efficiency.
[0379] Further, at least one of the first to third electron transport layers 634, 646, and 664 includes at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a fourth electron transport material represented by Chemical Formula 9, and has great advantages in driving voltage and luminous efficiency.
[0380] FIG. 8 is a schematic cross-sectional view of an organic light-emitting diode according to a seventh embodiment of the present invention.
[0381] Referring to FIG. 8, the organic light-emitting layer 462 includes a first light-emitting portion 730 including a yellow-green light-emitting material layer 710, a second light-emitting portion 740 including a first blue light-emitting material layer 750, and a third light-emitting portion 760 including a second blue light-emitting material layer 770. Further, the organic light-emitting layer 462 may further include a first charge generation layer 780 located between the first light-emitting portion 730 and the second light-emitting portion 740, and a second charge generation layer 790 located between the first light-emitting portion 730 and the third light-emitting portion 760.
[0382] The second light-emitting part 740 is located between the first electrode 460 and the first light-emitting part 730, and the third light-emitting part 760 is located between the first light-emitting part 730 and the second electrode 464. Also, the second light-emitting part 740 is located between the first electrode 460 and the first charge generation layer 780, and the third light-emitting part 760 is located between the second charge generation layer 790 and the second electrode 464. That is, the second light-emitting part 740, the first charge generation layer 780, the first light-emitting part 730, the second charge generation layer 790, and the third light-emitting part 760 are sequentially stacked on the first electrode 460.
[0383] In the organic light-emitting diode D of FIG. 6, the first light-emitting part 530 includes double-layer light-emitting material layers 510a and 510b, and in the organic light-emitting diode D of FIG. 7, the first light-emitting part 630 includes triple-layer light-emitting material layers 610a, 610b, and 610c. Alternatively, in the organic light-emitting diode D of FIG. 8, the first light-emitting part 730 includes a single-layer light-emitting material layer 710.
[0384] The first light-emitting part 730 may further include a first electron transport layer 734 located above the yellow-green light-emitting material layer 710 and a first hole transport layer 732 located below the yellow-green light-emitting material layer 710.
[0385] For example, in the first light-emitting part 730, the lower surface of the yellow-green light-emitting material layer 710 may be in contact with the first hole transport layer 732, and the upper surface of the yellow-green light-emitting material layer 710 may be in contact with the first electron transport layer 734.
[0386] The second light-emitting part 740 may further include at least one of a second hole transport layer 744 located below the first blue light-emitting material layer 750 and a second electron transport layer 748 located above the first blue light-emitting material layer 750. Also, the second light-emitting part 740 may further include a hole injection layer (742) located between the first electrode 460 and the second hole transport layer 744.
[0387] Further, the second light-emitting unit 740 may further include at least one of a first electron blocking layer (not shown) positioned between the second hole transport layer 744 and the first blue light-emitting material layer 750 and a first hole blocking layer (not shown) positioned between the second electron transport layer 746 and the first blue light-emitting material layer 750.
[0388] The third light-emitting unit 760 may further include at least one of a third hole transport layer 762 positioned below the second blue light-emitting material layer 770 and a third electron transport layer 766 positioned above the second blue light-emitting material layer 770. Further, the third light-emitting unit 760 may further include an electron injection layer (not shown) positioned between the second electrode 460 and the third electron transport layer 766.
[0389] Further, the third light-emitting unit 760 may further include at least one of a second electron blocking layer (not shown) positioned between the third hole transport layer 762 and the second blue light-emitting material layer 770 and a second hole blocking layer (not shown) positioned between the third electron transport layer 764 and the second blue light-emitting material layer 770.
[0390] The yellow-green light-emitting material layer 710 includes a first compound 712 which is an organic compound of the present invention represented by Chemical Formula 1. Further, the yellow-green light-emitting material layer 710 may further include a second compound 714 represented by Chemical Formula 3. Further, the yellow-green light-emitting material layer 710 may further include a third compound 716 which is one of the compounds of Chemical Formula 6.
[0391] In the yellow-green light-emitting material layer 710, the first compound 712 may be an n-type host (first host), the second compound 714 may be a p-type host (second host), and the third compound 716 may be a light emitter (dopant). The yellow-green light-emitting material layer 710 may have a thickness of 50 to 600 Å.
[0392] In the yellow-green light-emitting material layer 710, the weight ratio of each of the first and second compounds 712 and 714 may be greater than the weight ratio of the third compound 716, and the first compound 712 and the second compound 714 may have the same or different weight ratios. In the yellow-green light-emitting material layer 710, the weight ratio of the first compound 712 and the second compound 714 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the first compound 712 and the weight ratio of the second compound 714 may be the same. For example, the first compound 712 and the second compound 714 may have the same weight ratio, and the third compound 716 may have 5 to 25 wt% in the yellow-green light-emitting material layer 710.
[0393] Each of the first to third electron transport layers 734, 746, and 764 may contain at least one of the first electron transport material represented by Chemical Formula 7, the second electron transport material represented by Chemical Formula 8, and the fourth electron transport material represented by Chemical Formula 9.
[0394] The first blue light-emitting material layer 750 of the second light-emitting unit 740 includes a first blue host and a first blue dopant, and the second blue light-emitting material layer 770 of the third light-emitting unit 760 includes a second blue host and a second blue dopant.
[0395] Each of the first and second blue dopants may contain at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. Each of the first and second blue hosts may be the blue host material described above, and each of the first and second blue dopants may be the blue dopant material described above.
[0396] In the first blue light-emitting material layer 750, the first blue host may have a weight ratio greater than that of the first blue dopant. In the second blue light-emitting material layer 770, the second blue host may have a weight ratio greater than that of the second blue dopant. In each of the first and second blue light-emitting material layers 750 and 770, the first and second blue dopants may be doped at a content of 1 to 10 wt%, for example, 1 to 5 wt%.
[0397] The first charge generation layer 780 is located between the first light emitting part 730 and the second light emitting part 740, and the second charge generation layer 790 is located between the first light emitting part 730 and the third light emitting part 760. That is, the first light emitting part 730 and the second light emitting part 740 are connected by the first charge generation layer 780, and the first light emitting part 730 and the third light emitting part 760 are connected by the second charge generation layer 790. The first charge generation layer 780 may be a PN junction charge generation layer in which an N-type charge generation layer 782 and a P-type charge generation layer 784 are joined, and the second charge generation layer 790 may be a PN junction charge generation layer in which an N-type charge generation layer 792 and a P-type charge generation layer 794 are joined.
[0398] The N-type charge generation layer 782 of the first charge generation layer 780 is located between the first hole transport layer 732 and the second electron transport layer 746, and the P-type charge generation layer 784 of the first charge generation layer 780 is located between the N-type charge generation layer 782 and the first hole transport layer 732.
[0399] The N-type charge generation layer 792 of the second charge generation layer 790 is located between the first electron transport layer 734 and the third hole transport layer 762, and the P-type charge generation layer 794 of the second charge generation layer 790 is located between the N-type charge generation layer 792 and the third hole transport layer 762.
[0400] As described above, the organic light emitting diode D of the present invention includes a first light emitting part 730 including a yellow-green light emitting material layer 710, a second light emitting part 740 including a first blue light emitting material layer 750, and a third light emitting part 760 including a second blue light emitting material layer 770, and the organic light emitting diode D emits white light.
[0401] The yellow-green light emitting material layer 710 contains the organic compound of the present invention represented by Chemical Formula 1. Thereby, in the organic light emitting diode D, the driving voltage decreases and the light emitting efficiency increases.
[0402] In addition, the yellow-green light emitting material layer 710 further contains a compound represented by Chemical Formula 3 as a second host together with the first host which is the organic compound of the present invention, and has great advantages in driving voltage and light emitting efficiency.
[0403] In addition, the yellow-green light-emitting material layer 710 further includes a light-emitting body (dopant) which is one of the compounds of Chemical Formula 6 together with a first host which is a compound of Chemical Formula 1 and a second host which is a compound of Chemical Formula 3, and has great advantages in driving voltage and luminous efficiency.
[0404] In addition, at least one of the first to third electron transport layers 734, 746, 760 includes at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a fourth electron transport material represented by Chemical Formula 9, thereby having great advantages in driving voltage and luminous efficiency.
[0405] FIG. 9 is a schematic cross-sectional view of an organic light-emitting diode according to the eighth embodiment of the present invention.
[0406] Referring to FIG. 9, the organic light-emitting layer 462 includes a first light-emitting portion 830 including a green light-emitting material layer 810a and a second light-emitting portion 840 including a blue light-emitting material layer 850. Further, the organic light-emitting layer 462 may further include a charge generation layer 860 located between the first light-emitting portion 830 and the second light-emitting portion 840. Further, the first light-emitting portion 830 may further include a red light-emitting material layer 810b.
[0407] The second light-emitting portion 840 is located between the first electrode 460 and the first light-emitting portion 830. Further, the first light-emitting portion 830 is located between the second electrode 464 and the charge generation layer 860, and the second light-emitting portion 840 is located between the first electrode 460 and the charge generation layer 860. That is, the second light-emitting portion 840, the charge generation layer 860, and the first light-emitting portion 830 are sequentially stacked on the first electrode 460.
[0408] The organic light-emitting diode D in FIG. 6 includes first to third light-emitting portions 530, 540, 560, the organic light-emitting diode D in FIG. 7 includes first to third light-emitting portions 630, 640, 660, and the organic light-emitting diode D in FIG. 8 includes first to third light-emitting portions 730, 740, 760. Alternatively, the organic light-emitting diode D in FIG. 9 has a two-stack structure including first and second light-emitting portions 830, 840.
[0409] In the first light-emitting part 830, the red light-emitting material layer 810b may be located below the green light-emitting material layer 810a.
[0410] The first light-emitting part 830 may further include a first electron transport layer 834 located above the green light-emitting material layer 810a. Further, the first light-emitting part 830 may further include a first hole transport layer 832 located below the red light-emitting material layer 810b.
[0411] Further, the first light-emitting part 830 may further include an electron injection layer 836 located on the first electron transport layer 834.
[0412] Further, the first light-emitting part 830 may further include at least one of a first electron blocking layer (not shown) located between the first hole transport layer 832 and the red light-emitting material layer 810b and a first hole blocking layer (not shown) located between the first electron transport layer 834 and the green light-emitting material layer 810a.
[0413] The second light-emitting part 840 may further include at least one of a second hole transport layer 844 located below the blue light-emitting material layer 850 and a second electron transport layer 848 located above the blue light-emitting material layer 850. Further, the second light-emitting part 840 may further include a hole injection layer 842 located between the first electrode 460 and the second hole transport layer 844.
[0414] Further, the second light-emitting part 840 may further include at least one of a second electron blocking layer (not shown) located between the second hole transport layer 844 and the blue light-emitting material layer 850 and a second hole blocking layer (not shown) located between the second electron transport layer 846 and the blue light-emitting material layer 850.
[0415] The green light-emitting material layer 810a includes a first compound 812 which is an organic compound of the present invention represented by Chemical Formula 1. Further, the green light-emitting material layer 810a may further include a second compound 814 represented by Chemical Formula 3. Further, the green light-emitting material layer 810a may further include a third compound 816 which is one of the compounds of Chemical Formula 5.
[0416] In the green light-emitting material layer 810a, the first compound 812 may be an n-type host (first host), the second compound 814 may be a p-type host (second host), and the third compound 816 may be a light emitter (dopant). The green light-emitting material layer 810a may have a thickness of 50 to 600 Å.
[0417] In the green light-emitting material layer 810a, the weight ratio of each of the first and second compounds 812 and 814 may be greater than the weight ratio of the third compound 816, and the first compound 812 and the second compound 814 may have the same or different weight ratios. In the green light-emitting material layer 810a, the weight ratio of the first compound 812 to the second compound 814 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the first compound 812 and the weight ratio of the second compound 814 may be the same. For example, the first compound 812 and the second compound 814 may have the same weight ratio, and the third compound 816 may have 5 to 25 wt% in the green light-emitting material layer 810a.
[0418] Each of the first and second electron transport layers 834 and 846 may contain at least one of the first electron transport material represented by Chemical Formula 7, the second electron transport material represented by Chemical Formula 8, and the fourth electron transport material represented by Chemical Formula 9.
[0419] The blue light-emitting material layer 850 of the second light-emitting unit 840 contains a blue host and a blue dopant. Each blue dopant may contain at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescent compound. The blue host may be the blue host material described above, and the blue dopant may be the blue dopant material described above.
[0420] In the blue light-emitting material layer 850, the blue host may have a weight ratio greater than that of the blue dopant. In the blue light-emitting material layer 850, the blue dopant may be doped at a content of 1 to 10 wt%, for example, 1 to 5 wt%.
[0421] The charge generation layer 860 is located between the first light emitting part 830 and the second light emitting part 840. That is, the first light emitting part 830 and the second light emitting part 840 are connected by the charge generation layer 860. The charge generation layer 860 may be a PN junction charge generation layer in which an N-type charge generation layer 882 and a P-type charge generation layer 884 are joined.
[0422] The N-type charge generation layer 862 of the charge generation layer 860 is located between the first hole transport layer 832 and the second electron transport layer 846, and the P-type charge generation layer 864 of the charge generation layer 860 is located between the N-type charge generation layer 862 and the first hole transport layer 832.
[0423] As described above, the organic light emitting diode D of the present invention includes a first light emitting part 830 including a green light emitting material layer 810a and a red light emitting material layer 810b, and a second light emitting part 840 including a blue light emitting material layer 850, and the organic light emitting diode D emits white light.
[0424] The green light emitting material layer 810a contains the organic compound of the present invention represented by Chemical Formula 1. Thereby, in the organic light emitting diode D, the driving voltage decreases and the light emitting efficiency increases.
[0425] Further, the green light emitting material layer 810a further contains a compound represented by Chemical Formula 3 as a second host together with a first host which is the organic compound of the present invention, and has great advantages in driving voltage and light emitting efficiency.
[0426] Further, the green light emitting material layer 810a further contains a light emitter (dopant) which is one of the compounds of Chemical Formula 5 together with a first host which is the compound of Chemical Formula 1 and a second host which is the compound of Chemical Formula 3, and has great advantages in driving voltage and light emitting efficiency.
[0427] Further, when at least one of the first and second electron transport layers 834 and 846 contains at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a fourth electron transport material represented by Chemical Formula 9, it has great advantages in driving voltage and light emitting efficiency.
[0428] Figure 10 is a schematic cross-sectional view of an organic light-emitting diode according to a ninth embodiment of the present invention.
[0429] Referring to Figure 10, the organic light-emitting layer 462 includes a first light-emitting portion 930 including a yellow-green light-emitting material layer 910 and a second light-emitting portion 940 including a blue light-emitting material layer 950. Further, the organic light-emitting layer 462 may further include a charge generation layer 960 positioned between the first light-emitting portion 930 and the second light-emitting portion 940.
[0430] The second light-emitting portion 940 is positioned between the first electrode 460 and the first light-emitting portion 930. Also, the first light-emitting portion 930 is positioned between the second electrode 464 and the charge generation layer 960, and the second light-emitting portion 940 is positioned between the first electrode 460 and the charge generation layer 960. That is, the second light-emitting portion 940, the charge generation layer 960, and the first light-emitting portion 930 are sequentially stacked on the first electrode 460.
[0431] In the organic light-emitting diode D of Figure 9, the first light-emitting portion 830 includes a double-layer light-emitting material layer 810a, 810b, whereas in the organic light-emitting diode D of Figure 10, the first light-emitting portion 930 includes a single-layer light-emitting material layer 910.
[0432] The first light-emitting portion 930 may further include a first electron transport layer 934 positioned above the yellow-green light-emitting material layer 910 and a first hole transport layer 932 positioned below the yellow-green light-emitting material layer 910.
[0433] Also, the first light-emitting portion 930 may further include an electron injection layer 936 positioned on the first electron transport layer 934.
[0434] Also, the first light-emitting portion 930 may further include at least one of a first electron blocking layer (not shown) positioned between the first hole transport layer 932 and the yellow-green light-emitting material layer 910 and a first hole blocking layer (not shown) positioned between the first electron transport layer 934 and the yellow-green light-emitting material layer 910.
[0435] The second light-emitting unit 940 may further include at least one of a second hole transport layer 944 located below the blue light-emitting material layer 950 and a second electron transport layer 948 located above the blue light-emitting material layer 950. Further, the second light-emitting unit 940 may further include a hole injection layer 942 located between the first electrode 460 and the second hole transport layer 944.
[0436] Further, the second light-emitting unit 940 may further include at least one of a second electron blocking layer (not shown) located between the second hole transport layer 944 and the blue light-emitting material layer 950 and a second hole blocking layer (not shown) located between the second electron transport layer 946 and the blue light-emitting material layer 950.
[0437] The yellow-green light-emitting material layer 910 includes a first compound 912 which is an organic compound of the present invention represented by Chemical Formula 1. Further, the yellow-green light-emitting material layer 910 may further include a second compound 914 represented by Chemical Formula 3. Further, the yellow-green light-emitting material layer 910 may further include a third compound 916 which is one of the compounds of Chemical Formula 6.
[0438] In the yellow-green light-emitting material layer 910, the first compound 912 may be an n-type host (first host), the second compound 914 may be a p-type host (second host), and the third compound 916 may be a light emitter (dopant). The yellow-green light-emitting material layer 910 may have a thickness of 50 to 600 Å.
[0439] In the yellow-green light-emitting material layer 910, the weight ratio of each of the first and second compounds 912 and 914 may be greater than the weight ratio of the third compound 916, and the first compound 912 and the second compound 914 may have the same or different weight ratios. In the yellow-green light-emitting material layer 910, the weight ratio of the first compound 912 and the second compound 914 may be 1:9 to 9:1, for example, 2:8 to 8:2 or 3:7 to 7:3. Preferably, the weight ratio of the first compound 912 and the weight ratio of the second compound 914 may be the same. For example, the first compound 912 and the second compound 914 may have the same weight ratio, and the third compound 916 may have 5 to 25 wt% in the yellow-green light-emitting material layer 910.
[0440] Each of the first and second electron transport layers 934 and 946 may contain at least one of the first electron transport material represented by Chemical Formula 7, the second electron transport material represented by Chemical Formula 8, and the fourth electron transport material represented by Chemical Formula 9.
[0441] The blue light-emitting material layer 950 of the second light-emitting unit 940 includes a blue host and a blue dopant. The blue dopant may each contain at least one of a blue phosphorescent compound, a blue fluorescent compound, and a blue delayed fluorescence compound. The blue host may be the blue host material described above, and the blue dopant may be the blue dopant material described above.
[0442] In the blue light-emitting material layer 950, the blue host may have a weight ratio larger than that of the blue dopant. In the blue light-emitting material layer 950, the blue dopant may be doped at a content of 1 to 10 wt%, for example, 1 to 5 wt%.
[0443] The charge generation layer 960 is located between the first light-emitting unit 930 and the second light-emitting unit 940. That is, the first light-emitting unit 930 and the second light-emitting unit 940 are connected by the charge generation layer 960. The charge generation layer 960 may be a PN junction charge generation layer in which an N-type charge generation layer 982 and a P-type charge generation layer 984 are joined.
[0444] The N-type charge generation layer 962 of the charge generation layer 960 is located between the first hole transport layer 932 and the second electron transport layer 946, and the P-type charge generation layer 964 of the charge generation layer 960 is located between the N-type charge generation layer 962 and the first hole transport layer 932.
[0445] As described above, the organic light-emitting diode D of the present invention includes a first light-emitting unit 930 including a yellow-green light-emitting material layer 910 and a second light-emitting unit 940 including a blue light-emitting material layer 950, and the organic light-emitting diode D emits white light.
[0446] The yellow-green light-emitting material layer 910 contains the organic compound of the present invention represented by Chemical Formula 1. Thereby, in the organic light-emitting diode D, the driving voltage decreases and the luminous efficiency increases.
[0447] Further, the yellow-green light-emitting material layer 910 further contains, as a second host, a compound represented by Chemical Formula 3 together with a first host which is the organic compound of the present invention, and has great advantages in driving voltage and luminous efficiency.
[0448] Further, the yellow-green light-emitting material layer 910 further contains a light emitter (dopant) which is one of the compounds of Chemical Formula 6 together with a first host which is the compound of Chemical Formula 1 and a second host which is the compound of Chemical Formula 3, and has great advantages in driving voltage and luminous efficiency.
[0449] Further, at least one of the first and second electron transport layers 934 and 946 contains at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a fourth electron transport material represented by Chemical Formula 9, thereby having great advantages in driving voltage and luminous efficiency.
[0450] As described above, the preferred embodiments of the present invention have been described. However, those skilled in the art can understand that the present invention can be variously modified and changed without departing from the technical idea and scope of the present invention described in the following claims.
Explanation of Reference Numerals
[0451] 100, 400 Organic light-emitting display device 160, 460 First electrode 162, 462 Organic light-emitting layer 164, 464 Second electrode 230, 320, 340 (Green or yellow-green) light-emitting material layer 510a, 610a, 810a Green light-emitting material layer 610c, 710, 910 Yellow-green light-emitting material layer D Organic light-emitting diode
Claims
1. Represented by chemical formula 1, a1 is an integer from 0 to 5, a2 is an integer from 0 to 3, R 1 each is independently selected from the group consisting of deuterium, and a substituted or unsubstituted C1-C10 alkyl group; R 2 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; When a1 is 2 or more, a plurality of R 1 may be the same or different, and when a2 is 2 or more, a plurality of R 2 may be the same or different from each other, L 1 , L 2 , L 3 each is independently selected from the group consisting of a single bond (direct bond), a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; Ar 1 is selected from formula 1a-1 to formula 1a-5, In Chemical Formula 1a-1, b1 is an integer of 0 to 5, In Chemical Formula 1a-2, b2 is an integer of 0 to 7, In each of Chemical Formulae 1a-3 to 1a-5, each b3 is independently an integer of 0 to 4; In Chemical Formula 1a-4, V 1 is O, S, C (R 3 ) 2 is selected from In Chemical Formula 1a-5, V 2 is selected from O, S; In each of Chemical Formulae 1a-1 to 1a-5, R 3 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; When b1, b2, and b3 are each 2 or more, a plurality of R 3 may be the same or different from each other, Ar 2 is selected from formula 1b-1 and formula 1b-2, In each of Chemical Formula 1b-1 and Chemical Formula 1b-2, b4 is an integer of 0 to 4, R 4 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; When b4 is 2 or more, multiple R 4 may be the same or different from each other, In Chemical Formula 1b-2, R 5 is an organic compound selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C30 aryl group. [Chemical formula 1] [Chemical formula 1a-1] [Chemical formula 1a-2] [Chemical formula 1a-3] [Chemical formula 1a-4] [Chemical formula 1a-5] [Chemical formula 1b-1] [Chemical formula 1b-2]
2. Ar 1 , Ar 2 The organic compound according to claim 1 , wherein are different from each other.
3. The formula 1 is represented by the following formula 1-5 or 1-6: [Chemical formula 1-5] [Chemical formula 1-6] In each of Chemical Formula 1-5 and Chemical Formula 1-6, a1, a2, R 1 , R 2 , L 1 , L 2 , Ar 1 is the same as defined in Chemical Formula 1; In Chemical Formula 1-5, R 4 , b4 are the same as defined in formula 1b-1; In Chemical Formula 1-6, R 4 , R 5 2. The organic compound according to claim 1, wherein b1, b2, b3, b4 are the same as those defined in formula 1b-2.
4. The organic compound according to claim 1 , wherein the organic compound is one of the compounds of formula 2. [Chemical formula 2]
5. A substrate; an organic light emitting diode located on the substrate, the organic light emitting diode including a first electrode, a second electrode facing the first electrode, and a first light emitting portion including a first light emitting material layer and located between the first electrode and the second electrode; An organic light emitting device, wherein the first light emissive layer comprises a first compound which is an organic compound according to any one of claims 1 to 3.
6. The first light emitting material layer further includes a second compound represented by Chemical Formula 3, [Chemical formula 3] In Chemical Formula 3, c1 and c4 are each an integer from 0 to 4, and c2 and c3 are each an integer from 0 to 3; R 11 , R 12 , R 13 , R 14 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; L 11 , L 12 each is independently selected from the group consisting of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; Ar 11 , Ar 12 6. The organic light emitting device of claim 5, wherein each is independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group.
7. The organic light emitting device of claim 6 , wherein the second compound is one of the compounds of Formula 4: [Chemical formula 4]
8. The organic light emitting device of claim 7, wherein the first light emitting material layer further comprises a third compound, which is one of the compounds of Formula 5. [Chemical formula 5]
9. The organic light emitting device of claim 6, wherein the first light emitting material layer further comprises a third compound, which is one of the compounds of Formula 6: [Chemical formula 6]
10. 9. The organic light emitting device of claim 8, wherein the weight percentage of each of the first compound and the second compound is greater than the weight percentage of the third compound.
11. 11. The organic light emitting device of claim 10, wherein a weight ratio of the first compound to the second compound is from 1:9 to 9:1, from 2:8 to 8:2, or from 3:7 to 7:
3.
12. 9. The organic light emitting device of claim 8, wherein the weight percentage of the first compound is the same as the weight percentage of the second compound.
13. 13. The organic light emitting device of claim 12, wherein the third compound is present in the first light emitting layer in an amount of 5 to 25% by weight, based on the total weight of the components of the first light emitting layer.
14. The first light emitting unit further includes a first electron transport layer located between the first light emitting material layer and the second electrode, The first electron transport layer includes at least one of a first electron transport material represented by Chemical Formula 7, a second electron transport material represented by Chemical Formula 8, and a third electron transport material represented by Chemical Formula 9, [Chemical formula 7] In Chemical Formula 7, L 21 is selected from the group consisting of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; Ar 21 is represented by chemical formula 7a or chemical formula 7b, Ar 22 , Ar 23 each is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; [Chemical formula 7a] [Chemical formula 7b] In Chemical Formula 7a, d1 is an integer of 0 to 4; R 21 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; R 22 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; In Chemical Formula 7b, d2 is an integer of 0 to 4; R 23 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; R 24 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; [Chemical formula 8] In Chemical Formula 8, e1, e2, e3, and e4 each independently represent an integer of 0 to 4; e5 represents 0 or 1; R 31 , R 32 , R 33 , R 34 each is independently selected from the group consisting of deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; X 1 , X 2 , X 3 Each is independently N or CR 35 And X 1 , X 2 , X 3 at least two of are N; R 35 each is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; Ar 31 , Ar 32 each is independently selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; L 31 is selected from the group consisting of a substituted or unsubstituted C6 to C30 arylene group, and a substituted or unsubstituted C3 to C30 heteroarylene group; [Chemical formula 9] In Chemical Formula 9, f1, f2, and f3 each independently represent an integer of 0 to 4, and f4 represents an integer of 0 to 3; R 41 , R 42 , R 43 , R 44 each is independently selected from the group consisting of a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; X 11 is O, S or NR 45 and R 45 is a substituted or unsubstituted C6-C30 aryl group, which is linked to the adjacent benzene ring to form a ring; X 12 , X 13 , X 14 Each is independently N or CR 46 And X 12 , X 13 , X 14 at least two of are N; Ar 41 , Ar 42 , R 46 each is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; L 41 6. The organic light emitting device of claim 5, wherein is selected from the group consisting of a single bond, a substituted or unsubstituted C6 to C60 arylene group, and a substituted or unsubstituted C3 to C60 heteroarylene group.
15. The organic light emitting device of claim 14, wherein the first electron transport material is one of the compounds of Formula 10: [Chemical formula 10]
16. The organic light emitting device of claim 14, wherein the second electron transport material is one of the compounds of Formula 11: [Chemical formula 11]
17. The organic light emitting device of claim 14, wherein the third electron transport material is one of the compounds of Formula 12: [Chemical formula 12]
18. The organic light emitting diode further includes a second light emitting portion, the second light emitting portion including a second light emitting material layer and being located between the first light emitting portion and the second electrode; The organic light emitting device of claim 5 , wherein the second light emitting material layer comprises the first compound.
19. 6. The organic light emitting device of claim 5, wherein the organic light emitting diode further comprises a second light emitting portion, the second light emitting portion including a first blue light emitting material layer and positioned between the first electrode and the first light emitting portion.
20. The organic light emitting device of claim 19, wherein the first light emitting unit further comprises a red light emitting material layer disposed between the second light emitting unit and the first light emitting material layer.
21. The organic light emitting device of claim 20, wherein the first light emitting part further comprises a yellow-green light emitting material layer disposed between the first light emitting material layer and the red light emitting material layer.
22. 20. The organic light emitting device of claim 19, wherein the organic light emitting diode further comprises a third light emitting portion, the third light emitting portion including a second blue light emitting material layer and positioned between the first light emitting portion and the second electrode.
23. The organic light emitting device of claim 22, wherein the first light emitting unit further comprises a red light emitting material layer disposed between the second light emitting unit and the first light emitting material layer.
24. The organic light emitting device of claim 23, wherein the first light emitting part further comprises a yellow-green light emitting material layer disposed between the first light emitting material layer and the red light emitting material layer.
25. 6. The organic light emitting device of claim 5, further comprising color filter layers corresponding to red, green and blue pixel regions.
Citation Information
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