ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-ILLUMINATED DIODE CONTAINING IT

Abstract

Organometallic compound, which is compound 50:

Description

BACKGROUND area

[0001] The present disclosure relates to an organometallic compound and in particular to an organometallic compound with phosphorescence properties, as well as an organic light-emitting diode and a display device containing it. Description of the state of the art

[0002] Display devices are useful in various fields, and the creation of improved display devices is necessary. In particular, organic light emission display devices using organic light-emitting diodes (OLEDs) are undergoing rapid development.

[0003] When electric charges are injected into a light-emitting layer in an OLED, which is formed between a positive and a negative electrode, an electron and a hole in the light-emitting layer recombine to form an exciton, and the energy of the exciton is converted into light. This is how the OLED emits light.

[0004] US 2020 / 0227659 A1, US 2018 / 0138427 A1 and US 2015 / 0236276 A1 concern organic electroluminescent materials. SUMMARY OF THE REVELATION

[0005] Compared to conventional display devices, an organic light-emitting diode (OLED) can operate at a lower voltage, consume less power, reproduce excellent colors, and can be used in a variety of ways. The OLED can also be mounted on a flexible substrate to create a flexible or foldable device. Furthermore, the size of the OLED can be adjusted.

[0006] An OLED offers superior viewing angles and contrast ratios compared to a liquid crystal display (LCD) and is lightweight and ultra-thin because it does not require backlighting. An OLED can incorporate multiple organic layers between a negative electrode (e.g., electron injection electrode, cathode, etc.) and a positive electrode (e.g., hole injection electrode, anode, etc.). These layers may include a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron barrier layer, a light emission layer, an electron transport layer, and so on.

[0007] In the OLED structure described here, when a voltage is applied across the two electrodes, electrons and holes are injected from the negative and positive electrodes, respectively, into the light emission layer, thus generating excitons in the light emission layer which then fall to a ground state to emit light in the process.

[0008] Organic materials used in organic light-emitting diodes (OLEDs) can be broadly classified into light-emitting materials and charge-transport materials. The light-emitting material is a crucial factor in determining the luminescence efficiency of the OLED. The luminescent material must exhibit high quantum efficiency, excellent electron and hole mobility, and exist uniformly and stably within the light-emitting layer. Based on the colors of the light emitted, light-emitting materials can be further categorized into blue, red, and green light-emitting materials. A color-generating material may include a host and dopants to enhance color purity and luminescence efficiency through energy transfer.

[0009] When a fluorescent material is used, singlets (approximately 25% of the excitons generated in the light-emitting layer) are used to emit light, while most triplets (approximately 75% of the excitons generated in the light-emitting layer) are dissipated as heat. However, when a phosphorescent material is used, both singlets and triplets are used to emit light.

[0010] Traditionally, an organometallic compound is used as the phosphor material in an organic light-emitting diode (OLED). Ongoing research and development of the phosphor material is necessary to address issues of low efficiency and lifespan.

[0011] Consequently, one purpose of the present invention is to create an organometallic compound capable of reducing the operating voltage and improving efficiency and lifetime, and an organic light-emitting diode with an organic light-emitting layer containing the same.

[0012] The purposes of this disclosure are not limited to the purpose mentioned above. Other purposes and advantages of this disclosure, which are not mentioned, can be understood on the basis of the following descriptions and can be understood more clearly on the basis of embodiments of this disclosure. Furthermore, it is readily apparent that the purposes and advantages of this disclosure can be achieved using means shown in the claims and combinations thereof.

[0013] In one aspect, the present invention creates an organometallic compound, which is compound 50:

[0014] The organometallic compound according to the present disclosure can be used as a doping material for the light emission layer of the organic light-emitting diode, so that the operating voltage of the organic light-emitting diode can be reduced and the efficiency and lifetime characteristics of the organic light-emitting diode can be improved.

[0015] The effects of the present disclosure are not limited to the effects mentioned above, and other effects not mentioned are clearly understood by the person skilled in the art from the following descriptions. BRIEF DESCRIPTION OF THE DRAWINGS Fig.Figure 1 is a cross-sectional view schematically showing an organic light-emitting diode in which a light-emitting layer contains an organometallic compound according to an embodiment of the present disclosure. Fig. Figure 2 is a cross-sectional view schematically representing an organic light-emitting diode with a tandem structure having two light emission stacks, which contains an organometallic compound according to an embodiment of the present disclosure. Fig. Figure 3 is a cross-sectional view schematically representing an organic light-emitting diode with a tandem structure having three light emission stacks, which contains an organometallic compound according to an embodiment of the present disclosure. Fig.Figure 4 is a cross-sectional view schematically representing an organic light emission indicator device with an organic light-emitting diode according to an embodiment of the present disclosure. DETAILED DESCRIPTIONS OF THE EXECUTION FORMS

[0016] The advantages and features of the present disclosure and a method for achieving these advantages and features will become apparent with reference to embodiments that will be described in detail later, together with the accompanying drawings. However, the present disclosure is not limited to the embodiments disclosed below and can be implemented in various different forms and variations. Consequently, these embodiments are presented only to complete the present disclosure and to fully convey the scope of protection of the present disclosure to the person skilled in the art in the technical field to which the present disclosure belongs. All components of each OLED and each organic light emission indicator device according to all embodiments of the present disclosure are operationally coupled and configured.

[0017] A shape, size, ratio, angle, number, etc., disclosed in the drawings to describe the embodiments of the present disclosure are explanatory and the present disclosure is not limited to them. The same reference numerals refer to the same elements. Furthermore, descriptions and details of well-known steps and elements are omitted for the sake of simplicity. Moreover, numerous specific details are set forth in the following detailed description of the present disclosure to ensure a thorough understanding of the present disclosure. However, it is self-evident that the present disclosure can be carried out without these specific details. In other instances, well-known methods, procedures, components, and circuits have not been described in detail to avoid unnecessarily obscuring aspects of the present disclosure.

[0018] The terminology used herein is solely for the purpose of describing specific embodiments and is not intended to limit the present disclosure. As used herein, the singular terms "a" and "an" are intended to include the plural terms as well, unless the context clearly indicates otherwise. Furthermore, it is understood that the terms "comprise," "include," "comprehensive," and "including," when used in this patent description, indicate the presence of the specified features, integers, operations, elements, and / or components, but do not exclude the presence or addition of one or more other features, integers, operations, elements, components, and / or sections thereof. As used herein, the term "and / or" includes all combinations of one or more of the related listed items. The expression such as, for example,"At least one of" when preceding a list of elements can modify the entire list of elements and does not modify the individual elements within the list. When interpreting numerical values, an error or tolerance may occur, even without an explicit description.

[0019] Furthermore, it is self-evident that when a first element or layer is described as being "on" a second element or layer, the first element may be arranged directly on the second element or indirectly on the second element, with a third element or layer positioned between the first and second elements or between the first and second layers. It is also self-evident that when an element or layer is described as being "connected" or "coupled" to another element or layer, it may be located directly on, connected to, or coupled to the other element or layer, or one or more intermediate elements or layers may be present.Furthermore, it is also self-evident that when an element or layer is described as "between" two elements or layers, it may be the only element or layer between the two elements or layers, or one or more intermediate elements or layers may also be present.

[0020] Furthermore, as used here, if a layer, film, area, plate, or the like is arranged "on" or "on a top side" of another layer, film, area, plate, or the like, the former may directly contact the latter, or yet another layer, film, area, plate, or the like may be arranged between the former and the latter. As used here, if a layer, film, area, plate, or the like is arranged directly "on" or "on a top side" of another layer, film, area, plate, or the like, the former directly contacts the latter, and yet another layer, film, area, plate, or the like is not arranged between the former and the latter.Furthermore, as used here, if a layer, film, area, plate, or the like is arranged "below" or "under" another layer, film, area, plate, or the like, the former may directly contact the latter, or yet another layer, film, area, plate, or the like may be arranged between the former and the latter. As used here, if a layer, film, area, plate, or the like is arranged directly "below" or "under" another layer, film, area, plate, or the like, the former directly contacts the latter, and yet another layer, film, area, plate, or the like is not arranged between the former and the latter.

[0021] In descriptions of temporal relationships, for example, temporally preceding relationships between two events, such as "after", "following", "before", etc., another event may occur in between if "directly after", "directly following" or "directly before" is not specified.

[0022] It is understood that, although the terms "first," "second," "third," and so on may be used here to describe different elements, components, regions, layers, and / or sections, these elements, components, regions, layers, and / or sections should not be limited by these terms. These terms are used to distinguish one element, component, region, layer, or section from another. Consequently, a first element, component, region, layer, or section described below could be referred to as a second element, component, region, layer, or section without departing from the intent and scope of this disclosure.

[0023] The features of the various embodiments of the present disclosure can be partially or completely combined and can be technically related to one another or work together. The embodiments can be implemented independently of one another and can be implemented in a related relationship with one another.

[0024] When interpreting a numerical value, the value is interpreted as encompassing an error range if no separate explicit description of it exists.

[0025] It is self-evident that when an element or layer is described as "connected" or "coupled" to another element or layer, it may be directly attached to, connected to, or coupled to that other element or layer, or one or more intermediate elements or layers may be present. It is also self-evident that when an element or layer is described as "between" two elements or layers, it may be the only element or layer between the two elements or layers, or one or more intermediate elements or layers may also be present.

[0026] The features of the various embodiments of the present disclosure can be partially or completely combined and can be technically related to one another or work together. The embodiments can be implemented independently of one another and can be implemented in a related relationship with one another.

[0027] Unless otherwise defined, all terms, including technical and scientific terms used herein, have the same meaning as they would normally be understood by a person skilled in the art in the field to which this inventive concept belongs. Furthermore, it is self-evident that terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant field and not in an idealized or overly formal sense, unless expressly defined as such herein.

[0028] As used here, the phrase "adjacent substituents are linked together to form a ring (or ring structure)" means that adjacent substituents can bond to one another to form a substituted or unsubstituted alicyclic or aromatic ring. The phrase "adjacent substituent" to a given substituent can mean a substituent that replaces an atom directly bonded to an atom replaced by the given substituent, a substituent that is sterically closest to the given substituent, or a substituent that replaces an atom replaced by the given substituent. For example, two substituents replacing an ortho position in a benzene ring structure and two substituents replacing the same carbon in an aliphatic ring can be interpreted as "adjacent substituents."

[0029] Below, a structure and preparation example of an organometallic compound according to the present disclosure and an organic light-emitting diode containing it are described.

[0030] The organometallic compound according to the invention is compound 50. Although not bound to any theory, the inventors of the present disclosure have found that when a fused ring structure (R) as in compound 50 is introduced, the principal axis direction length of a molecule of the organometallic compound is increased to improve horizontal orientation and to impart stiffness to the molecule of the organometallic compound. Consequently, we have carried out the present disclosure. When the organometallic compound according to the invention is used as a doping material of a light-emitting layer, the full width at half maximum (FWHM) can be reduced, thus improving the color gamut and increasing luminous efficiency and lifetime.

[0031] According to one implementation of the present disclosure, the organometallic compound according to the invention can be used as a red phosphorescent material or a green phosphorescent material, preferably as a red phosphorescent material.

[0032] With reference to Fig.1. According to one implementation of the present disclosure, an organic light-emitting diode 100 can be created, comprising a first electrode 110; a second electrode 120 facing the first electrode 110; and an organic layer 130 arranged between the first electrode 110 and the second electrode 120. The organic layer 130 can comprise a light-emitting layer 160, and the light-emitting layer 160 can comprise a host material 160' and doping materials 160". The doping materials 160" can consist of the organometallic compound according to the invention.Furthermore, in the organic light-emitting diode 100, the organic layer 130, which is arranged between the first electrode 110 and the second electrode 120, can be formed by sequentially stacking a hole injection layer 140 (HIL), a hole transport layer 150 (HTL), a light emission layer 160 (EML), an electron transport layer 170 (ETL), and an electron injection layer 180 (EIL) onto the first electrode 110. The second electrode 120 can be formed on the electron injection layer 180, and a protective layer can be formed on top of it.

[0033] Furthermore, in Fig.1. A hole transport auxiliary layer is added between the hole transport layer 150 and the light emission layer 160. The hole transport auxiliary layer can contain a compound with good hole transport properties and can reduce the difference between the HOMO energy levels of the hole transport layer 150 and the light emission layer 160 in order to adjust the hole injection properties. The accumulation of holes at an interface between the hole transport auxiliary layer and the light emission layer 160 can thus be reduced, thereby minimizing a quenching phenomenon in which excitons disappear at the interface due to polarons. Consequently, the degradation of the element can be reduced and the element can be stabilized, thereby improving its efficiency and lifetime.

[0034] The first electrode 110 can act as a positive electrode and can consist of ITO, IZO, tin oxide, or zinc oxide as a conductive material with a relatively high work function value. However, the present disclosure is not limited to this.

[0035] The second electrode 120 can act as a negative electrode and can comprise Al, Mg, Ca, or Ag as a conductive material with a relatively low work function value, or an alloy or combination thereof. However, the present disclosure is not limited to this.

[0036] The hole injection layer 140 can be positioned between the first electrode 110 and the hole transport layer 150. The hole injection layer 140 can have a function for improving interfacial characteristics between the first electrode 110 and the hole transport layer 150 and can be selected from a material with suitable conductivity. The hole injection layer 140 can comprise one or more compounds selected from the group consisting of MTDATA, CuPc, TCTA, HATCN, TDAPB, PEDOT / PSS, and N1,N1'-([1,1'-Biphenyl]-4,4'-diyl)bis(N1,N4,N4)-triphenylbenzene-1,4-diamine). Preferably, the hole injection layer can comprise 140 N1,N1'-([1,1'-Biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine). However, the present disclosure is not limited thereto.

[0037] The hole transport layer 150 can be positioned adjacent to the light emission layer and between the first electrode 110 and the light emission layer 160. The material of the hole transport layer 150 can comprise a compound selected from the group consisting of TPD, NPB, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl)-4-amine, etc. Preferably, the material of the hole transport layer 150 can comprise NPB. However, the present disclosure is not limited to this.

[0038] According to the present disclosure, the light-emitting layer 160 can be formed by doping a host material 160' with the organometallic compound according to the invention as a doping material 160" in order to improve the luminous efficiency of the diode 100. The doping material 160" can be used as a green or red light-emitting material and preferably as a red phosphorescent material.

[0039] The doping concentration of the doping material 160" according to the present disclosure can be adjusted to be within a range of 1 to 30 wt.% based on a total weight of the host material 160'. However, the disclosure is not limited to this. The doping concentration can, for example, be in a range of 2 to 20 wt.%, 3 to 15 wt.%, 5 to 10 wt.%, 3 to 8 wt.%, 2 to 6 wt.%, 2 to 5 wt.%, or 2 to 3 wt.%.

[0040] The light-emitting layer 160 according to the present disclosure contains the host material 160', which is known in the field, and can achieve an effect of the present disclosure, while the layer 160 contains the organometallic compound of the invention as a doping material 160". According to the present disclosure, the host material 160' can, for example, comprise a compound containing a carbazole group and can preferably comprise a host material selected from the group consisting of CBP (carbazole biphenyl), mCP (1,3-bis(carbazol-9-yl), and the like. However, the disclosure is not limited thereto.

[0041] Furthermore, the electron transport layer 170 and the electron injection layer 180 can be stacked sequentially between the light emission layer 160 and the second electrode 120. The electron transport layer 170 requires a material with high electron mobility so that electrons can be stably supplied to the light emission layer with smooth electron transport.

[0042] The material of the electron transport layer 170 can, for example, comprise a compound selected from a group consisting of Alq3 (tris(8-hydroxyquinolino)aluminium), Liq (8-hydroxyquinolinolatolithium), PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), TAZ (3-(4-biphenyl)4-phenyl-5-tert-butylphenyl-1,2,4-triazole), Spiro-PBD, BAlq (bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium), SAlq, TPBi (2,2',2-(1,3,5-benzintriyl)-tris(1-phenyl-1-H-benzimidazole), oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, and The electron transport layer material consists of 2-(4-(9,10-Di(naphthalen-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole. Preferably, the electron transport layer material can comprise 170 2-(4-(9,10-Di(naphthalen-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole. However, the present disclosure is not limited to this.

[0043] The electron injection layer 180 serves to facilitate electron injection, and the material of the electron injection layer may comprise a compound selected from the group consisting of Alq3 (tris(8-hydroxyquinolino)aluminium), PBD, TAZ, Spiro-PBD, BAlq, SAlq, etc. However, the present disclosure is not limited thereto. Alternatively, the electron injection layer 180 may consist of a metal compound. The metal compound may, for example, comprise one or more selected from the group consisting of Liq, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2, and RaF2. However, the present disclosure is not limited thereto.

[0044] The organic light-emitting diode (OLED) according to the present disclosure can be embodied as a white LED with a tandem structure. The organic tandem LED according to an explanatory embodiment of the present disclosure can be configured in a structure in which adjacent light-emitting stacks of two or more are interconnected via a charge-generating layer (CGL). The organic LED can comprise at least two light-emitting stacks arranged on a substrate, each of the at least two light-emitting stacks comprising a first and a second electrode facing each other, and the light-emitting layer arranged between the first and second electrodes to emit light in a specific wavelength band. The multiple light-emitting stacks can emit light of the same color or of different colors.Furthermore, one or more light emission layers can be contained in a light emission stack, and the multiple light emission layers can emit light of the same color or different colors.

[0045] In this case, the light emission layer contained in at least one of the multiple light emission stacks can contain the organometallic compound according to the invention as doping materials. Adjacent light emission stacks in the tandem structure can be interconnected via the charge generation layer CGL with an N-type charge generation layer and a P-type charge generation layer.

[0046] Fig. 2 and Fig.Figure 3 are cross-sectional views that schematically show an organic light-emitting diode in a tandem structure with two light emission stacks or an organic light-emitting diode in a tandem structure with three light emission stacks according to some implementations of the present disclosure.

[0047] As in Fig.As shown in Figure 2, an organic light-emitting diode 100 according to the present disclosure comprises a first electrode 110 and a second electrode 120 facing each other, and an organic layer 230 positioned between the first electrode 110 and the second electrode 120. The organic layer 230 can be positioned between the first electrode 110 and the second electrode 120 and can comprise a first light-emitting stack ST1 with a first light-emitting layer 261, a second light-emitting stack ST2 positioned between the first light-emitting stack ST1 and the second electrode 120 and comprising a second light-emitting layer 262, and the charge-generating layer CGL positioned between the first and second light-emitting stacks ST1 and ST2. The charge-generating layer CGL can comprise an N-type charge-generating layer 291 and a P-type charge-generating layer 292.The first light-emitting layer 261 and / or the second light-emitting layer 262 can comprise the organometallic compound according to the invention as doping materials. As in . Fig. As shown in Figure 2, for example, the second light emission layer 262 of the second light emission stack ST2 can contain a host material 262' and doping materials 262" doped into it, which consist of the organometallic compound according to the invention. Fig. 2. Each of the first and second light emission stacks ST1 and ST2 may further comprise an additional light emission layer in addition to each of the first light emission layer 261 and the second light emission layer 262.

[0048] As in Fig.As shown in Figure 3, the organic light-emitting diode 100 according to the present disclosure comprises the first electrode 110 and the second electrode 120 facing each other, and an organic layer 330 positioned between the first electrode 110 and the second electrode 120. The organic layer 330 can be positioned between the first electrode 110 and the second electrode 120 and can comprise the first light-emitting stack ST1 with the first light-emitting layer 261, the second light-emitting stack ST2 with the second light-emitting layer 262, a third light-emitting stack ST3 with a third light-emitting layer 263, a first charge-generating layer CGL1 positioned between the first and second light-emitting stacks ST1 and ST2, and a second charge-generating layer CGL2 positioned between the second and third light-emitting stacks ST2 and ST3.The first charge-generating layer CGL1 can comprise an N-type charge-generating layer 291 and a P-type charge-generating layer 292. The second charge-generating layer CGL2 can comprise an N-type charge-generating layer 293 and a P-type charge-generating layer 294. The first light-emitting layer 261, the second light-emitting layer 262, and / or the third light-emitting layer 263 can contain the organometallic compound according to the invention as doping materials. As in . Fig. As shown in Figure 3, for example, the second light emission layer 262 of the second light emission stack ST2 can contain the host material 262' and the doping materials 262" doped into it, which consist of the organometallic compound according to the invention. Fig.3 Each of the first, second and third light emission stacks ST1, ST2 and ST3 may further comprise an additional light emission layer in addition to each of the first light emission layer 261, the second light emission layer 262 and the third light emission layer 263.

[0049] Furthermore, an organic light-emitting diode according to an embodiment of the present disclosure can comprise a tandem structure in which four or more light emission stacks and three or more charge generation layers are arranged between the first electrode and the second electrode.

[0050] The organic light-emitting diode according to the present disclosure can be used as a light-emitting element of any organic light-emitting display device and a lighting device. In one implementation, Fig.4 a cross-sectional view which schematically represents an organic light emission indicator device with the organic light-emitting diode according to some embodiments of the present disclosure as the light emission element thereof.

[0051] As in Fig. As shown in Figure 4, an organic light emission indicator device 3000 comprises a substrate 3010, an organic light-emitting diode 4000, and an encapsulation film 3900 covering the organic light-emitting diode 4000. A driver thin-film transistor Td, acting as the driver element, and the organic light-emitting diode 4000, which is connected to the driver thin-film transistor Td, are positioned on the substrate 3010.

[0052] In Fig.4 are a gate line and a data line that intersect to define a pixel area, a power line that extends parallel to and spaced apart from one of the gate line and the data line, a switching thin-film transistor connected to the gate line and the data line, and a storage capacitor connected to an electrode of the thin-film transistor and the power line, further formed on the substrate 3010.

[0053] The control thin-film transistor Td is connected to the switching thin-film transistor and comprises a semiconductor layer 3100, a gate electrode 3300, a source electrode 3520 and a drain electrode 3540.

[0054] The semiconductor layer 3100 can be formed on the substrate 3010 and can consist of an oxide semiconductor material or polycrystalline silicon. If the semiconductor layer 3100 consists of an oxide semiconductor material, a light-shielding pattern can be formed beneath the semiconductor layer 3100. The light-shielding pattern prevents light from entering the semiconductor layer 3100, thus preventing light-induced degradation. Alternatively, the semiconductor layer 3100 can consist of polycrystalline silicon. In this case, both edges of the semiconductor layer 3100 can be doped with impurities.

[0055] The gate insulating layer 3200, which consists of an insulating material, is formed over a total surface area of ​​the substrate 3010 and on the semiconductor layer 3100. The gate insulating layer 3200 can consist of an inorganic insulating material such as silicon oxide or silicon nitride.

[0056] The gate electrode 3300, which consists of a conductive material such as a metal, is formed on the gate insulating layer 3200 and corresponds to a center of the semiconductor layer 3100. The gate electrode 3300 is connected to the switching thin-film transistor.

[0057] The intermediate insulating layer 3400, which consists of an insulating material, is formed over the entire surface of the substrate 3010 and on the gate electrode 3300. The intermediate insulating layer 3400 can consist of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photoacrylic.

[0058] The intermediate insulation layer 3400 has a first and a second semiconductor layer contact hole 3420 and 3440 defined therein, each exposing opposite sides of the semiconductor layer 3100. The first and the second semiconductor layer contact holes 3420 and 3440 are each positioned on opposite sides of the gate electrode 3300 and are spaced apart from the gate electrode 3300.

[0059] The source electrode 3520 and the drain electrode 3540, which consist of a conductive material such as metal, are formed on the intermediate insulating layer 3400. The source electrode 3520 and the drain electrode 3540 are positioned around the gate electrode 3300 and are spaced apart from each other, contacting opposite sides of the semiconductor layer 3100 via the first and second semiconductor layer contact holes 3420 and 3440, respectively. The source electrode 3520 is connected to a power line.

[0060] The semiconductor layer 3100, the gate electrode 3300, the source electrode 3520 and the drain electrode 3540 form the driver thin-film transistor Td. The driver thin-film transistor Td has a coplanar structure in which the gate electrode 3300, the source electrode 3520 and the drain electrode 3540 are positioned on the semiconductor layer 3100.

[0061] Alternatively, the driver thin-film transistor Td can have a reverse staggered structure in which the gate electrode is located below the semiconductor layer, while the source and drain electrodes are located above the semiconductor layer. In this case, the semiconductor layer can be made of amorphous silicon. In one example, the switching thin-film transistor can have essentially the same structure as that of the driver thin-film transistor (Td).

[0062] In one example, the organic light emission display device 3000 can include a color filter 3600 that absorbs the light generated by the electroluminescent element (light-emitting diode) 4000. The color filter 3600 can, for example, absorb red (R), green (G), blue (B), and white (W) light. In this case, the light-absorbing patterns of the red, green, and blue color filters can be formed separately in different pixel areas. Each of these color filter patterns can be arranged to overlap with each organic layer 4300 of the organic light-emitting diode 4000 to emit light of a wavelength band corresponding to each color filter. The inclusion of the color filter 3600 can enable the organic light emission display device 3000 to achieve full color.

[0063] For example, if the organic light emission indicator device 3000 is of a bottom emission type, the color filter 3600, which absorbs light, can be positioned on a section of the intermediate insulating layer 3400 corresponding to the organic light-emitting diode 4000. In an optional embodiment, if the organic light emission indicator device 3000 is of a top emission type, the color filter can be positioned on the organic light-emitting diode 4000, for example, on a second electrode 4200. The color filter 3600 can, for example, be configured to have a thickness of 2 to 5 µm.

[0064] In one example, a planarization layer 3700 with a drain contact hole 3720, defined therein, is designed to cover the drain electrode 3540 of the driving thin-film transistor Td.

[0065] On the planarization layer 3700, each first electrode 4100, which is connected to the drain electrode 3540 of the control thin-film transistor Td via the drain contact hole 3720, is individually formed in each pixel area.

[0066] The first electrode 4100 can act as the positive electrode (anode) and can be made of a conductive material with a relatively high work function value. For example, the first electrode 4100 can be made of a transparent conductive material such as ITO, IZO, or ZnO.

[0067] In an example, if the organic light emission indicator device 3000 is of a top-emission type, a reflective electrode or reflective layer may further be formed below the first electrode 4100. The reflective electrode or reflective layer may, for example, consist of an aluminum (Al), silver (Ag), nickel (Ni), and an aluminum-palladium-copper alloy (APC alloy).

[0068] A bank layer 3800, covering an edge of the first electrode 4100, is formed on the planarization layer 3700. The bank layer 3800 exposes a center of the first electrode 4100 that corresponds to the pixel area.

[0069] An organic layer 4300 is formed on the first electrode 4100. If required, the organic light-emitting diode 4000 can have a tandem structure. Regarding the tandem structure, see below. Fig. 2 to Fig.4, which show some embodiments of the present disclosure, and to which reference is made above to the descriptions thereof.

[0070] The second electrode 4200 is formed on the substrate 3010, on which the organic layer 4300 has been formed. The second electrode 4200 is arranged over the entire surface of the display area and consists of a conductive material with a relatively low work function value and can be used as a negative electrode (cathode). The second electrode 4200 can, for example, be made of aluminum (Al), magnesium (Mg), or an aluminum-magnesium alloy (Al-Mg alloy).

[0071] The first electrode 4100, the organic layer 4300 and the second electrode 4200 form the organic light-emitting diode 4000.

[0072] An encapsulation film 3900 is formed on the second electrode 4200 to prevent external moisture from penetrating the organic light-emitting diode 4000. Fig. 4. The encapsulation film 3900 can have a triple-layer structure in which a first inorganic layer, an organic layer, and an inorganic layer are stacked sequentially. However, the present disclosure is not limited to this.

[0073] The following are examples of preparation and examples of the present revelation. However, the following examples are only examples of the present revelation; the present revelation is not limited to them. Preparation example (1) Preparation of the connection 1 Preparation of the D1 connection

[0074] M1 (9.78 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D1 (7.36 g, 60% yield). Preparing the connection 1

[0075] D1 (7.36 g, 4.5 mmol), pentane-2,4-dione (4.51 g, 45 mmol), Na₂CO₃ (9.54 g, 90 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer. After filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane. Consequently, compound 1 (4.37 g, yield 55%) was obtained. MS (m / z): 882.18(2) Preparation of connection 31 Preparation of the D31 connection

[0076] M31 (12.82 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D31 (8.27 g, 55% yield). Preparation of connection 31

[0077] D31 (8.27 g, 4.13 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (9.92 g, 41 mmol), Na₂CO₃ (8.74 g, 82.5 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 31 (4.98 g, 50% yield). MS (m / z): 1206.46(3) Preparing connection 50(Step 1) Preparing connection A1 Preparation of the A1-1 connection

[0078] In a reaction vessel, 5-bromo-4,6-dichloropyrimidine (25.6 g, 112.34 mmol), (1-methoxynaphthalen-2-yl)boronic acid (24.97 g, 123.57 mmol), Pd(PPh3)4 (6.5 g, 5.62 mmol), and K2CO3 (31.05 g, 224.68 mmol) were dissolved in 1,4-dioxane (500 mL) and distilled water (100 mL), and the mixture was heated under reflux for 15 hours. After completion of the reaction, the mixture was cooled to room temperature and subjected to extraction using dichloromethane and distilled water. MgSO4 was added to an organic layer to remove moisture, and the solvent was then removed by filtration under reduced pressure. Column chromatography was performed using hexane and dichloromethane. Consequently, compound A1-1 (30.51 g, yield 89%) was obtained. MS (m / z): 305.16 Preparation of connection A1-2

[0079] A1-1 (30.51 g, 99.98 mmol) was dissolved in dichloromethane (450 ml) in a reaction vessel, and then BBr3 (23.7 ml, 249.95 mmol) was added dropwise, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction by adding distilled water, the mixture was stirred at room temperature for 30 minutes, followed by extraction using dichloromethane and distilled water. MgSO4 was added to an organic layer to remove moisture, and then the solvent was removed by filtration under reduced pressure. Column chromatography was carried out with hexane and dichloromethane to obtain compound A1-2 (28.23 g, 97% yield). MS (m / z): 291.13 Preparation of connection A1

[0080] A1-2 (28.23 g, 96.98 mmol) and Cs2CO3 (47.40 g, 145.47 mmol) were dissolved in 300 mL of N,N-dimethylacetamide in a reaction vessel, and the mixture was heated under reflux for 16 hours. A reaction solution was cooled to room temperature and filtered through Celite to remove any inorganic components, and a filtrate was concentrated. The mixture was dissolved in ethyl acetate, and the resulting solution was filtered through silica gel and then filtered under reduced pressure to remove the solvent. A resulting solid was converted to a suspension using hexane to obtain compound A1 (22.47 g, 91% yield) as an ivory-colored solid. MS (m / z): 254.67 (Step 2) Preparation of connection M50

[0081] A1 (22.4 g, 87.96 mmol), 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30.02 g, 96.75 mmol), Pd(PPh3)4 (10.17 g, 8.80 mmol), and K2CO3 (24.31 g, 175.92 mmol) were dissolved in 1,4-dioxane (330 mL) and distilled water (66 mL), and the mixture was heated under reflux for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and subjected to extraction using dichloromethane and distilled water. MgSO4 was added to an organic layer to remove moisture, and the solvent was then removed by reduced-pressure filtration. Column chromatography was performed using hexane and dichloromethane. Consequently, compound M50 (25.84 g, yield 73%) was obtained. MS (m / z): 402.49 (Step 3) Preparing the connection 50 Preparation of the D50 connection

[0082] M50 (25 g, 62.11 mmol), 2-ethoxyethanol 500 ml, and distilled water 167 ml were placed in a reaction vessel and nitrogen bubbling was carried out for 1 hour. Then, IrCl3,H2O (9.95 g, 28.23 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D50 (16.3 g, yield 56%). Preparing for connection 50

[0083] D50 (16.3 g, 7.91 mmol), 3,7-diethylnonane-4,6-dione (5.88 g, 27.68 mmol), Na₂CO₃ (16.76 g, 158.16 mmol), and 300 mL of 2-ethoxyethanol were placed in a reaction vessel and heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, followed by extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane. Consequently, compound 50 (8.2 g, yield 43%) was obtained. MS (m / z): 1206.50(4) Preparation of the connection 57 Preparation of the D57 connection

[0084] M57 (13.28 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D57 (7.42 g, yield 48%). Preparation of connection 57

[0085] M57 (7.42 g, 3.6 mmol) and 200 ml of THF were placed in a reaction vessel under a nitrogen stream. Then, L57 (1.75 g, 7.9 mmol), dissolved in THF, was slowly added, followed by stirring at room temperature overnight. After completion of the reaction, the THF was removed under reduced pressure in a vacuum. The mixture was extracted with toluene and filtered with Celite. Toluene was removed under reduced pressure, and column chromatography was carried out with hexane and dichloromethane to obtain compound 57 (4.65 g, yield 55%). MS (m / z): 1175.43(5) Preparation of the connection 58 Preparation of the D58 connection

[0086] M58 (15.13 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D58 (8.06 g, yield 47%). Preparation of connection 58

[0087] 2-Bromopropane (1.73 g, 14.10 mmol) and 50 mL of THF were placed in a reaction vessel under a nitrogen stream, the temperature was lowered to -78 °C, and n-BuLi (5.8 mL, 2.5 M in hexane) was slowly added. After 30 minutes, N,N'-Diisopropylcarbodiimide (1.78 g, 14.10 mmol) was slowly added, and the mixture was stirred for 30 minutes while maintaining the temperature. The reaction mixture was then transferred to a reaction vessel containing D58 (8.06 g, 3.53 mmol) dissolved in 200 mL of THF, and the mixture was stirred at 80 °C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed, and the mixture was recrystallized using the solvents THF / pentane and dichloromethane / hexane. Consequently, compound 58 (4.41 g, yield 49%) was obtained. MS (m / z): 1175.43(6) Preparation of connection 74 Preparation of the D74 connection

[0088] M74 (12.82 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel and nitrogen bubbling was carried out for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D74 (7.82 g, yield 52%). Preparation of connection 74

[0089] D74 (7.82 g, 3.9 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (9.37 g, 39 mmol), Na₂CO₃ (8.27 g, 78 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 74 (4.23 g, yield 45%). MS (m / z): 1206.46(7) Preparation of the connection 86 Preparation of the D86 connection

[0090] M86 (12.82 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D86 (6.02 g, 40% yield). Preparation of connection 86

[0091] D86 (6.02 g, 3.0 mmol), 3,7-diethylnonane-4,6-dione (6.37 g, 30 mmol), Na₂CO₃ (6.36 g, 60 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and the solvent was removed by filtration under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 86 (2.97 g, yield 42%). MS (m / z): 1178.43(8) Preparation of connection 102 Preparation of the D102 connection

[0092] M102 (10.70 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D102 (8.13 g, yield 62%). Preparation of connection 102

[0093] D102 (8.13 g, 4.65 mmol), pentane-2,4-dione (4.66 g, 46.5 mmol), Na₂CO₃ (9.86 g, 93 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane. Consequently, compound 102 (4.62 g, yield 53%) was obtained. MS (m / z): 938.24(9) Preparation of connection 124 Preparation of the D124 connection

[0094] M124 (11.70 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D124 (7.15 g, yield 51%). Preparation of connection 124

[0095] D124 (7.15 g, 3.83 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (7.05 g, 38.3 mmol), Na₂CO₃ (8.11 g, 77 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 124 (4.06 g, yield 49%). MS (m / z): 1082.32(10) Preparation of connection 148 Preparation of the D148 connection

[0096] M148 (12.42 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel and nitrogen bubbling was carried out for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D148 (5.58 g, yield 38%). Preparation of connection 148

[0097] D148 (5.58 g, 2.85 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (6.85 g, 28.5 mmol), Na₂CO₃ (6.04 g, 57 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 148 (2.70 g, yield 40%). MS (m / z): 1182.36(11) Preparation of the connection 170 Preparation of the D170 connection

[0098] M170 (13.81 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D170 (8.77 g, 55% yield). Preparation of connection 170

[0099] D170 (8.77 g, 4.13 mmol), 3,7-diethylnonane-4,6-dione (8.76 g, 41.3 mmol), Na₂CO₃ (8.74 g, 83 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane. Consequently, compound 170 (4.90 g, yield 48%) was obtained. MS (m / z): 1238.42(12) Preparation of connection 177 Preparation of the D177 connection

[0100] M177 (13.81 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D177 (7.17 g, yield 45%). Preparation of connection 177

[0101] M177 (7.17 g, 3.4 mmol) and 200 ml of THF were placed in a reaction vessel under a nitrogen stream, and L177 (1.64 g, 7.4 mmol), dissolved in THF, was slowly added, followed by stirring at room temperature overnight. After completion of the reaction, the THF was removed under reduced pressure in a vacuum, and the mixture was subjected to extraction with toluene and filtered with Celite. Toluene was removed under reduced pressure, and column chromatography was carried out with hexane and dichloromethane to obtain compound 177 (4.08 g, yield 50%). MS (m / z): 1207.39(13) Preparation of connection 178 Preparation of the D178 connection

[0102] M178 (15.66 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D178 (7.58 g, yield 43%). Preparation of connection 178

[0103] 2-Bromopropane (1.59 g, 12.90 mmol) and 50 mL of THF were placed in a reaction vessel under a nitrogen stream, and the temperature was lowered to -78 °C. n-BuLi (5.3 mL, 2.5 M in hexane) was then added slowly. After 30 minutes, while maintaining the temperature, N,N'-Diisopropylcarbodiimide (1.63 g, 12.90 mmol) was added slowly, and the mixture was stirred for 30 minutes. The reaction mixture was then transferred to a reaction vessel containing D178 (7.58 g, 3.23 mmol) dissolved in 200 mL of THF, and the mixture was stirred at 80 °C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed, and the mixture was recrystallized using the solvents THF / pentane and dichloromethane / hexane. Consequently, compound 178 (3.71 g, yield 44%) was obtained. MS (m / z): 1308.54(14) Preparation of connection 190 Preparation of the D190 connection

[0104] M190 (13.81 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D190 (9.09 g, yield 57%). Preparation of connection 190

[0105] D190 (9.09 g, 4.28 mmol), 3,7-diethylnonane-4,6-dione (9.08 g, 42.8 mmol), Na₂CO₃ (9.06 g, 86 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 190 (4.87 g, yield 46%). MS (m / z): 1238.42 Preparation of the D216 connection

[0106] M216 (14.28 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D216 (6.38 g, yield 39%). Preparation of connection 216

[0107] D216 (6.38 g, 2.93 mmol), 3,7-diethyl-5-methylnonane-4,6-dione (6.62 g, 29.3 mmol), Na2CO3 (6.20 g, 59 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO4 was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 216 (2.85 g, yield 38%). MS (m / z): 1280.46(16) Preparation of connection 223 Preparation of the D223 connection

[0108] M223 (12.16 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D223 (8.66 g, 60% yield). Preparation of connection 223

[0109] D223 (8.66 g, 4.50 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (8.29 g, 45.0 mmol), Na2CO3 (9.54 g, 90 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO4 was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 223 (5.10 g, yield 51%). MS (m / z): 1110.36(17) Preparation of connection 241 Preparation of the D241 connection

[0110] M241 (10.64 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, and nitrogen bubbling was carried out for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D241 (6.27 g, yield 48%). Preparation of connection 241

[0111] D241 (6.27 g, 3.60 mmol), pentane-2,4-dione (3.60 g, 36.0 mmol), Na₂CO₃ (7.63 g, 72 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 241 (3.16 g, yield 47%). MS (m / z): 934, 29(18) Preparation of connection 271 Preparation of the D271 connection

[0112] M271 (13.68 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D271 (8.07 g, yield 51%). Preparation of connection 271

[0113] D271 (8.07 g, 3.83 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (9.19 g, 38.3 mmol), Na₂CO₃ (8.11 g, 77 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 271 (4.14 g, yield 43%). MS (m / z): 1258.57(19) Preparation of the connection 290 Preparation of the D290 connection

[0114] M290 (14.14 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D290 (8.45 g, yield 52%). Preparation of connection 290

[0115] D290 (8.45 g, 3.90 mmol), 3,7-diethylnonane-4,6-dione (8.28 g, 39.0 mmol), Na2CO3 (8.27 g, 78 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO4 was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 290 (4.42 g, yield 45%). MS (m / z): 1258.57(20) Preparation of the connection 298 Preparation of the D298 connection

[0116] M298 (15.99 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel and nitrogen bubbling was carried out for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D298 (7.35 g, yield 41%). Preparation of connection 298

[0117] 2-Bromopropane (1.51 g, 12.30 mmol) and 50 mL of THF were placed in a reaction vessel under a nitrogen stream, and the temperature was lowered to -78 °C. n-BuLi (5.0 mL, 2.5 M in hexane) was added slowly. After 30 minutes, while maintaining the temperature, N,N'-Diisopropylcarbodiimide (1.55 g, 12.30 mmol) was added slowly, and the mixture was stirred for 30 minutes. The reaction mixture was then transferred to a reaction vessel containing D298 (7.35 g, 3.08 mmol) dissolved in 200 mL of THF, and the mixture was stirred at 80 °C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed, and the mixture was recrystallized using the solvents THF / pentane and dichloromethane / hexane. Consequently, compound 298 (3.27 g, yield 40%) was obtained. MS (m / z): 1328.69(21) Preparation of the connection 300 Preparing the D300 connection

[0118] M300 (15.07 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel and nitrogen bubbling was carried out for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D300 (5.13 g, yield 30%). Preparing for connection 300

[0119] Bromobenzene (1.41 g, 9.00 mmol) and 50 mL of THF were placed in a reaction vessel under a nitrogen stream and the temperature was lowered to -78 °C. n-BuLi (3.7 mL, 2.5 M in hexane) was then added slowly. After 30 minutes, while maintaining the temperature, N,N'-methanediylidene dicyclohexanamine (1.86 g, 9.00 mmol) was added slowly, and the mixture was stirred for 30 minutes. The reaction mixture was then transferred to a reaction vessel containing D300 (5.13 g, 2.25 mmol) dissolved in 100 mL of THF, and the mixture was stirred at 80 °C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed, and the mixture was recrystallized using the solvents THF / pentane and dichloromethane / hexane. Consequently, compound 300 (2.18 g, yield 35%) was obtained. MS (m / z): 1386.68(22) Preparation of connection 310 Preparing the D310 connection

[0120] M310 (14.14 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D310 (6.33 g, yield 39%). Preparation of connection 310

[0121] D310 (6.33 g, 2.93 mmol), 3,7-diethylnonane-4,6-dione (6.21 g, 29.3 mmol), Na₂CO₃ (6.20 g, 59 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 310 (2.72 g, yield 37%). MS (m / z): 1258.57(23) Preparation of connection 330 Preparing the D330 connection

[0122] M330 (14.14 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel and nitrogen bubbling was carried out for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D330 (6.50 g, yield 40%). Preparation of connection 330

[0123] D330 (6.50 g, 3.00 mmol), 3,7-diethylnonane-4,6-dione (6.37 g, 30.0 mmol), Na₂CO₃ (6.36 g, 60 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 330 (2.95 g, yield 39%). MS (m / z): 1258.57(24) Preparation of connection 352 Preparation of the D352 connection

[0124] M352 (14.14 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D352 (6.01 g, yield 37%). Preparation of connection 352

[0125] D352 (6.01 g, 2.78 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (6.67 g, 27.8 mmol), Na₂CO₃ (5.88 g, 56 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 352 (2.50 g, yield 35%). MS (m / z): 1286.60(25) Preparation of connection 363 Preparation of the D363 connection

[0126] M363 (12.99 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D363 (5.32 g, yield 35%). Preparation of connection 363

[0127] D363 (5.32 g, 2.63 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (4.84 g, 26.3 mmol), Na₂CO₃ (5.56 g, 53 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 363 (2.38 g, yield 39%). MS (m / z): 1160.53(26) Preparation of connection 382 Preparation of the D382 connection

[0128] M382 (11.13 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D382 (7.02 g, yield 52%). Preparation of connection 382

[0129] D382 (7.02 g, 3.90 mmol), pentane-2,4-dione (3.90 g, 39.0 mmol), Na₂CO₃ (8.27 g, 78 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 382 (3.31 g, yield 44%). MS (m / z): 964.31(27) Preparation of connection 410 Preparation of the D410 connection

[0130] M410 (13.71 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D410 (7.13 g, yield 45%). Preparation of connection 410

[0131] D410 (7.13 g, 3.38 mmol), 3,7-diethylnonane-4,6-dione (7.17 g, 33.8 mmol), Na₂CO₃ (7.15 g, 68 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane. Consequently, compound 410 (3.58 g, yield 43%) was obtained. MS (m / z): 1232.53(28) Preparation of connection 417 Preparation of the D417 connection

[0132] M417 (13.71 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D417 (6.50 g, yield 41%). Preparation of connection 417

[0133] M417 (6.50 g, 3.1 mmol) and 200 ml of THF were placed in a reaction vessel under a nitrogen stream, and L417 (1.49 g, 6.8 mmol), dissolved in THF, was slowly added, followed by stirring at room temperature overnight. After completion of the reaction, the THF was removed under reduced pressure in a vacuum, the mixture was extracted with toluene, and filtered with Celite. Toluene was removed under reduced pressure, and column chromatography was carried out with hexane and dichloromethane to obtain compound 417 (2.88 g, yield 39%). MS (m / z): 1201.50(29) Preparation of connection 418 Preparation of the D418 connection

[0134] M418 (15.56 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel and nitrogen bubbling was carried out for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D418 (6.84 g, yield 39%). Preparation of connection 418

[0135] 2-Bromopropane (1.44 g, 11.70 mmol) and 50 mL of THF were placed in a reaction vessel under a nitrogen stream, and the temperature was lowered to -78 °C. n-BuLi (4.80 mL, 2.5 M in hexane) was added slowly. After 30 minutes, while maintaining the temperature, N,N'-Diisopropylcarbodiimide (1.48 g, 11.70 mmol) was added slowly, and the mixture was stirred for 30 minutes. The reaction mixture was then transferred to a reaction vessel containing D418 (6.84 g, 2.93 mmol) dissolved in 200 mL of THF, and the mixture was stirred at 80 °C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed, and the mixture was recrystallized using the solvents THF / pentane and dichloromethane / hexane. Consequently, compound 418 (2.90 g, yield 38%) was obtained. MS (m / z): 1302.65(30) Preparation of connection 426 Preparation of the D426 connection

[0136] M426 (13.71 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D426 (5.86 g, yield 37%). Preparation of connection 426

[0137] D426 (5.86 g, 2.28 mmol), 3,7-diethylnonane-4,6-dione (5.89 g, 27.8 mmol), Na₂CO₃ (5.88 g, 56 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane. Consequently, compound 426 (2.39 g, yield 35%) was obtained. MS (m / z): 1232.53(31) Preparation of connection 441 (Step 1) Preparation of connection A2Preparation of connection A2-1

[0138] 4,6-Dichloropyrimidine (25 g, 167.81 mmol), (3-nitronaphthalen-2-yl)boronic acid (40.05 g, 184.59 mmol), Pd(PPh3)4 (9.7 g, 8.39 mmol), and K2CO3 (46.38 g, 335.62 mmol) were dissolved in 1,4-dioxane (500 mL) and distilled water (100 mL) in a reaction vessel, and the mixture was heated under reflux for 15 hours. After completion of the reaction, the mixture was cooled to room temperature and subjected to extraction using dichloromethane and distilled water. MgSO4 was added to an organic layer to remove moisture, and then the solvent was removed by filtration under reduced pressure. Column chromatography was performed using hexane and dichloromethane. Consequently, compound A2-1 (36.43 g, yield 76%) was obtained. MS (m / z): 285.69 Preparation of connection A2-2

[0139] A2-1 (36.43 g, 127.53 mmol) and PPh3 (83.62 g, 318.82 mmol) were dissolved in 1,2-dichlorobenzene (400 mL) in a reaction vessel, and the mixture was heated under reflux for 15 hours. After completion of the reaction, the mixture was cooled to room temperature and subjected to extraction using dichloromethane and distilled water. MgSO4 was added to an organic layer to remove moisture, and then the solvent was removed by filtration under reduced pressure. Column chromatography was performed with hexane and dichloromethane. Consequently, compound A2-2 (22.32 g, yield 69%) was obtained. MS (m / z): 253.69 Preparation of connection A2

[0140] A2-2 (22.32 g, 87.98 mmol), iodobenzene (19.74 g, 94.78 mmol), CuI (15 g, 87.98 mmol), trans-1,2-cyclohexanediamine (10.05 g, 87.98 mmol), and NaOH (7.04 g, 175.96 mmol) were dissolved in toluene (250 mL) in a reaction vessel, and the mixture was heated under reflux for 16 hours. After the reaction solution cooled to room temperature, a resulting solution was subjected to extraction using dichloromethane and distilled water. MgSO4 was added to an organic layer to remove moisture, and then the solvent was removed by filtration under reduced pressure. Column chromatography was performed using hexane and dichloromethane. Consequently, compound A2 (25.2 g, yield 87%) was obtained in the form of an ivory-colored solid. MS (m / z): 329.78 (Step 2) Preparation of connection M441

[0141] A2 (25.2 g, 76.41 mmol), (3,5-Dimethylphenyl)boronic acid (12.61 g, 84.05 mmol), Pd(PPh3)4 (8.83 g, 7.64 mmol), and K2CO3 (21.12 g, 152.82 mmol) were dissolved in 1,4-dioxane (375 mL) and distilled water (75 mL) in a reaction vessel, and the mixture was heated under reflux for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and subjected to extraction using dichloromethane and distilled water. MgSO4 was added to an organic layer to remove moisture, and then the solvent was removed by filtration under reduced pressure. Column chromatography was performed with hexane and MC. Consequently, compound M441 (22.28 g, yield 73%) was obtained. MS (m / z): 399.49 (Step 3) Preparing the connection 441 Preparation of the D441 connection

[0142] M441 (13.18 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D441 (5.07 g, yield 33%). Preparation of connection 441

[0143] D441 (5.07 g, 2.48 mmol), 1,3-dicyclohexyl-2-methylpropane-1,3-dione (6.20 g, 24.8 mmol), Na₂CO₃ (5.25 g, 50 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 441 (1.90 g, yield 31%). MS (m / z): 1238.48(32) Preparation of connection 470 Preparation of the D470 connection

[0144] M470 (13.71 g, 33 mmol), 200 ml of 2-ethoxyethanol, and 66 ml of distilled water were placed in a reaction vessel, followed by nitrogen bubbling for 1 hour. Then, IrCl3,H2O (5.29 g, 15 mmol) was added, and the mixture was heated under reflux for 24 hours. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D470 (6.34 g, 40% yield). Preparation of connection 470

[0145] D470 (6.34 g, 3.00 mmol), 3,7-diethylnonane-4,6-dione (6.37 g, 30.0 mmol), Na₂CO₃ (6.36 g, 60 mmol), and 200 mL of 2-ethoxyethanol were placed in a reaction vessel, and the mixture was heated under reflux for 24 hours in a nitrogen atmosphere. After the reaction was complete, dichloromethane was added to the reaction mixture to dissolve it, and the resulting solution was then subjected to extraction with dichloromethane and distilled water. MgSO₄ was used to remove water from an organic layer, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with hexane and dichloromethane to obtain compound 470 (2.88 g, yield 39%). MS (m / z): 1232.53 Present example<Vorliegendes Beispiel 1>

[0146] A glass substrate with a 1000 Å thick ITO (indium tin oxide) film applied to it was washed, followed by ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, and methanol. The glass substrate was then dried. This resulted in a transparent ITO electrode. HI-1, as the hole injection material, was deposited onto the transparent ITO electrode using thermal vacuum deposition. This resulted in a 60 nm thick hole injection layer. NPB, as the hole transport material, was then deposited onto the hole injection layer using thermal vacuum deposition. This resulted in a hole transport layer with a thickness of 80 nm. Finally, CBP, as the host material for a light emission layer, was deposited onto the hole transport layer using thermal vacuum deposition.Compound 1, acting as a dopant, was doped into the host material at a concentration of 5%. Consequently, a light-emitting layer with a thickness of 30 nm was formed. ET-1:Liq (1:1) (30 nm) was deposited on the light-emitting layer as material for an electron transport layer and an electron injection layer. Then, 100 nm thick aluminum was deposited on top to form a negative electrode. In this way, an organic light-emitting diode was fabricated.

[0147] HI-1 means N1,N1'-([1,1'-Biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine).

[0148] ET-1 means 2-(4-(9,10-Di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole. <Vorliegende Beispiele 2 bis 32 und Vergleichsbeispiel 1>

[0149] Organic light-emitting diodes of Examples 2 to 32 and Comparative Example 1 were prepared in the same manner as in Example 1, except that the compounds listed in Tables 1 to 3 below were used as dopant material instead of compound 1 in Example 1. Examples 1, 2, 4 to 32 are not according to the invention. < Performance evaluation of organic light-emitting diodes>

[0150] Regarding the organic light-emitting diodes prepared according to the present examples 1 to 32 and the comparative example 1, operating voltages and efficiency characteristics were determined at 10 mA / cm². 2 Current and lifetime characteristics under acceleration at 20 mA / cm 2The operating voltage (V), EQE (%), and LT95 (%) were measured and converted into values ​​relative to values ​​of comparison example 1. The results are shown in Tables 1 to 3 below. LT95 refers to a lifetime rating scheme and represents the time it takes for an organic light-emitting diode to lose 5% of its initial brightness. Table 1 Examples Doping material Operating voltage (%, relative value) EQE(%, relative value) LT95(%, relative value) Comparative example 1 RD 100 100 100 Example 1 1 91,5 121 134 Example 2 31 89,0 131 152 Example 3 50 88,1 138 158 Example 4 57 86,5 141 122 Example 5 58 87,3 145 116 Example 6 74 90,6 127 140 Example 7 86 89,8 134 146 Example 8 102 92,3 124 128 Example 9 124 90,6 118 127 Example 10 148 88,1 131 145

[0151] The structure of RD as doping material for comparison example 1 in Table 1 is as follows. Table 2 Examples Doping material Operating voltage (%, relative value) EQE(%, relative value) LT95(%, relative value) Comparative example 1 RD 100 100 100 Example 11 170 87,3 135 149 Example 12 177 85,6 138 122 Example 13 178 86,5 142 118 Example 14 190 89,8 125 140 Example 15 216 89,0 128 136 Example 16 223 91,5 121 131 Example 17 241 90,4 109 130 Example 18 271 87,1 117 138 Example 19 290 86,3 125 162 Present example 20 298 84,6 137 114 Table 3 Examples Doping material Operating voltage (V, relative value) EQE(%, relative value) LT95(%, relative value) Comparative example 1 RD 100 100 100 Example 21 300 85,4 133 122 Example 22 310 89,6 113 170 Example 23 330 88,8 121 154 Example 24 352 87,9 129 146 Example 25 363 89,2 103 113 Example 26 382 88,3 107 118 Example 27 410 85,0 123 139 Example 28 417 84,2 127 107 Example 29 418 83,3 131 102 Present example 30 426 86,7 115 128 Example 31 441 87,5 111 123 Example 32 470 85,8 119 134

[0152] From the results in Table 1 to Table 3 above, it can be identified that in the organic light-emitting diode in which the organometallic compound of each of the present examples 1 to 32 is used as the doping material of the light emission layer of the diode, compared to those in Comparative Example 1, the operating voltage of the diode is reduced and the external quantum efficiency (EQE) and lifetime (LT95) of the diode are improved.

Claims

[1] Organometallic compound, which is compound 50: [2] Organic light emission device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer that is positioned between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer, wherein the light emission layer comprises a doping material, wherein the doping material comprises the organometallic compound according to claim 1. [3] Organic light emission device comprising: a first electrode and a second electrode facing each other; and a first light emission stack and a second light emission stack positioned between the first electrode and the second electrode, wherein each of the first light emission stack and the second light emission stack comprises at least one light emission layer, wherein at least one of the light emission layers is a red phosphorescent light emission layer, wherein the red phosphorescent light emission layer comprises a doping material, wherein the doping material comprises the organometallic compound according to claim 1. [4] Organic light emission indicator device comprising: a substrate; a control element that is positioned on the substrate; and an organic light emission element arranged on the substrate and connected to the control element, wherein the organic light emission element comprises the organic light emission device according to claim 2 or 3.

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