Organometallic compound and organic light emitting diode comprising the same

Abstract

Disclosed are an organic metal compound represented by Chemical Formula I, and an organic light emitting diode comprising the same. The organic metal compound has excellent light emitting characteristics and structural stability. Accordingly, when the organic metal compound is used in an organic light emitting diode, the operating voltage of the organic light emitting diode is reduced, and the efficiency and lifespan characteristics of the organic light emitting diode are improved.

Description

Technical Field

[0001] This disclosure relates to an organometallic compound, and more specifically, to an organometallic compound having phosphorescent properties and an organic light-emitting diode comprising the organometallic compound. Background Technology

[0002] As display devices are applied in various fields, interest in them is increasing. One type of display device that is rapidly developing is the organic light-emitting diode (OLED) display device.

[0003] In an organic light-emitting diode (OLED), when charge is injected into the light-emitting layer formed between the positive and negative electrodes, electrons and holes recombine in the light-emitting layer to form excitons, thereby converting the energy of the excitons into light. Therefore, the OLED emits light. Compared to traditional display devices, OLEDs can operate at low voltages, consume relatively less power, exhibit superior color, and can be used in a variety of ways because they can be applied to flexible substrates. Furthermore, the size of OLEDs can be freely adjusted.

[0004] Compared to liquid crystal displays (LCDs), organic light-emitting diodes (OLEDs) offer superior viewing angles and contrast, and are lightweight and ultra-thin because they do not require backlighting. An OLED comprises multiple organic layers between a negative electrode (electron injection electrode; cathode) and a positive electrode (hole injection electrode; anode). These organic layers may include hole injection layers, hole transport layers, hole transport assist layers, electron blocking layers, light-emitting layers, and electron transport layers, among others.

[0005] In this organic light-emitting diode structure, when a voltage is applied between the two electrodes, electrons and holes are injected into the light-emitting layer from the negative electrode and the positive electrode, respectively, thus generating excitons in the light-emitting layer. The excitons then descend to the ground state and emit light.

[0006] Organic materials used in organic light-emitting diodes (OLEDs) can be broadly categorized into luminescent materials and charge-transport materials. The luminescent material is a crucial factor determining the luminous efficiency of an OLED. It must possess high quantum efficiency, excellent electron and hole mobility, and exist uniformly and stably within the luminescent layer. Based on the color of light, luminescent materials can be classified as those emitting blue, red, and green light. Color-generating materials can include a matrix and dopants to increase color purity and luminous efficiency through energy transfer.

[0007] When fluorescent materials are used, approximately 25% of the excitons generated in the emissive layer are singlet states used for luminescence, while the majority (75%) of the excitons generated in the emissive layer are triplet states that dissipate as heat. However, when phosphorescent materials are used, both singlet and triplet states are used for luminescence.

[0008] Organometallic compounds are commonly used as phosphorescent materials in organic light-emitting diodes (OLEDs). There is an ongoing need to research and develop phosphorescent materials to address issues of low efficiency and lifespan. Summary of the Invention

[0009] Therefore, the purpose of this disclosure is to provide an organometallic compound that can reduce operating voltage and improve efficiency and lifespan, and an organic light-emitting diode including an organic light-emitting layer containing the organometallic compound.

[0010] The purpose of this disclosure is not limited to those mentioned above. Other purposes and advantages not mentioned in this disclosure may be understood based on the following description and may become clearer based on embodiments of this disclosure. Furthermore, it will be readily understood that the purposes and advantages of this disclosure can be achieved using the means shown in the claims and combinations thereof.

[0011] To achieve the above objectives, this disclosure provides an organometallic compound having a novel structure represented by the following chemical formula I, an organic light-emitting diode (OLED) wherein the light-emitting layer comprises the organometallic compound as a dopant, and an organic light-emitting display device including the organic light-emitting diode:

[0012] [Chemical Formula I]

[0013]

[0014] In the above chemical formula I,

[0015] M can represent a centrally coordinated metal, and includes one selected from the group consisting of: molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt), and gold (Au).

[0016] A can represent a ring structure selected from pyridine and pyrimidine, wherein the ring structure is optionally substituted with deuterium.

[0017] R1 through R8 can each independently represent one selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, and substituted or unsubstituted C4 to C20 bicyclic alkyl.

[0018] R9 can each independently represent one selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, halogen, cyano, and alkoxy.

[0019] Optionally, when each of R1 to R9 is substituted, the substituents of each of R1 to R9 may be independently selected from the group consisting of deuterium, halogens, and substituted or unsubstituted C3 to C10 cycloalkyl groups, and when the number of substituents in each of R1 to R9 is at least two, the substituents may be the same or different from each other.

[0020] Y can represent a group selected from the following: BR 10 CR 10 R 11 C=O, CNR 10 SiR 10 R 11 NR 10 PR 10 AsR 10 SbR 10 P(O)R 10 P(S)R 10 、P(Se)R 10 As(O)R 10 As(S)R 10 As(Se)R 10 、Sb(O)R 10 、Sb(S)R 10 、Sb(Se)R 10 , O, S, Se, Te, SO, SO2, SeO, SeO2, TeO and TeO2,

[0021] X1 to X4 can each independently represent a selection from CR 12 And one of nitrogen (N),

[0022] Optionally, the substituents R of X1 to X4 12 Two adjacent substituents can fused together to form a five- or six-membered aromatic ring structure, and optionally, the aromatic ring structure can be substituted with deuterium.

[0023] R 10 To R 12Each can independently represent one selected from the group consisting of: hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C1 to C20 heteroalkyl, substituted or unsubstituted C7 to C20 arylalkyl, substituted or unsubstituted C2 to C 20-Alkenyl, substituted or unsubstituted C3 to C20 cycloalkenyl, substituted or unsubstituted C1 to C20 heteroalkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C1 to C20 alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphinyl.

[0024] Optionally, when R 10 To R 12 When each one is replaced, R 10 To R 12 The substituents of each can be independently chosen from one of the groups consisting of deuterium and halogens, and when R 10 To R 12 When each of them has at least two substituents, the substituents can be the same or different from each other.

[0025] It can represent bidentate ligands.

[0026] m can be an integer of 1, 2 or 3, n can be an integer of 0, 1 or 2, m+n can be the oxidation number of metal M, and p can be 2.

[0027] The organometallic compounds according to this disclosure can be used as dopants in the phosphorescent layer of organic light-emitting diodes (OLEDs), thereby improving the efficiency and lifetime characteristics of OLEDs, reducing the operating voltage of OLEDs, and thus enabling OLEDs to operate at low power levels.

[0028] The effects of this disclosure are not limited to those mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art based on the following description. Attached Figure Description

[0029] Figure 1 This is a schematic cross-sectional view of an organic light-emitting diode in which the light-emitting layer comprises an organometallic compound according to an illustrative embodiment of the present disclosure.

[0030] Figure 2This is a schematic cross-sectional view of an organic light-emitting diode having a series structure of two light-emitting layers and containing an organometallic compound represented by chemical formula I according to an illustrative embodiment of the present disclosure.

[0031] Figure 3 This is a schematic cross-sectional view of an organic light-emitting diode having a series structure of three light-emitting layers and containing an organometallic compound represented by chemical formula I according to an illustrative embodiment of the present disclosure.

[0032] Figure 4 This is a schematic cross-sectional view of an organic light-emitting display device including an organic light-emitting diode according to an embodiment of the present disclosure. Detailed Implementation

[0033] The advantages and features of this disclosure, as well as the methods for achieving these advantages and features, will become apparent from the embodiments described in detail below with reference to the accompanying drawings. However, this disclosure is not limited to the embodiments disclosed below, but can be implemented in various different forms. Therefore, these embodiments are set forth only to complete this disclosure and to fully inform those skilled in the art of the scope of this disclosure, which is limited only by the scope of the claims.

[0034] For simplicity and clarity, the elements in the accompanying drawings are not necessarily drawn to scale. The same reference numerals in different drawings denote the same or similar elements, thus performing similar functions. Furthermore, for the sake of simplicity, descriptions and details of well-known steps and elements have been omitted. In addition, numerous specific details are set forth in the following detailed description of this disclosure to provide a thorough understanding of it. However, it should be understood that this disclosure can be practiced without these specific details. In other instances, well-known methods, processes, components, and circuits have not been described in detail so as not to unnecessarily obscure aspects of this disclosure. Examples of various embodiments are further shown and described below. It should be understood that the description herein is not intended to limit the claims to the specific embodiments described. Rather, this disclosure is intended to cover substitutions, modifications, and equivalents that may fall within the spirit and scope of this disclosure as defined by the appended claims.

[0035] The shapes, dimensions, ratios, angles, quantities, etc., disclosed in the accompanying drawings used to describe embodiments of this disclosure are illustrative and the disclosure is not limited thereto. The same reference numerals refer to the same elements herein.

[0036] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of this disclosure. As used herein, the singular constructs “a” and “an” are also intended to include the plural constructs, unless the context clearly indicates otherwise. It should also be understood that, when used in this specification, the terms “comprising,” “including,” “comprises,” and “including” specify the presence of the stated features, integers, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, integers, operations, elements, components, and / or portions thereof. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. When preceding a list of elements, expressions such as “at least one” may modify the entire list of elements and may not modify individual elements of the list. In the interpretation of numerical values, errors or tolerances may occur even if not explicitly described.

[0037] Furthermore, it should be understood that when a first element or layer is referred to as existing “on” a second element or layer, the first element may be directly disposed on the second element or may be indirectly disposed on the second element by a third element or layer disposed between the first and second elements or layers. It should be understood that when an element or layer is referred to as being “connected to” or “coupled to” another element or layer, it may be directly connected to or coupled to another element or layer, or one or more intermediate elements or layers may exist. Furthermore, it should be understood that when an element or layer is referred to as being “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 exist.

[0038] Furthermore, as used herein, when a layer, membrane, region, plate, etc., is disposed "on" or "on top" of another layer, membrane, region, plate, etc., the former can directly contact the latter, or another layer, membrane, region, plate, etc., can be disposed between the former and the latter. As used herein, when a layer, membrane, region, plate, etc., is directly disposed "on" or "on top" of another layer, membrane, region, plate, etc., the former directly contacts the latter, and no other layer, membrane, region, plate, etc., is disposed between the former and the latter. Furthermore, as used herein, when a layer, membrane, region, plate, etc., is disposed "below" or "under" another layer, membrane, region, plate, etc., the former can directly contact the latter, or another layer, membrane, region, plate, etc., can be disposed between the former and the latter. As used herein, when a layer, membrane, region, plate, etc., is directly disposed "below" or "under" another layer, membrane, region, plate, etc., the former directly contacts the latter, and no other layer, membrane, region, plate, etc., is disposed between the former and the latter.

[0039] In descriptions of temporal relationships, such as the temporal precedence between two events as "after," "following," or "before," another event may occur between the two events unless it is specified that "immediately after," "immediately following," or "immediately before."

[0040] When a particular implementation can be carried out differently, a particular function or operation in a particular module may occur in a different order than that specified in the flowchart. For example, two consecutive blocks may be executed substantially simultaneously, or the two blocks may be executed in reverse order depending on the functions or operations involved.

[0041] It should be understood that although the terms “first,” “second,” “third,” etc., may be used herein to describe various elements, components, regions, layers, and / or parts, these elements, components, regions, layers, and / or parts should not be limited by these terms. These terms are used to distinguish one element, component, region, layer, or part from another. Therefore, without departing from the spirit and scope of this disclosure, the first element, component, region, layer, or part described below may be referred to as the second element, component, region, layer, or part.

[0042] The features of the various embodiments of this disclosure can be combined in whole or in part with each other, and can be technically related to or interoperable with each other. The embodiments can be implemented independently of each other, or they can be implemented together in a related relationship.

[0043] When interpreting numerical values, the value is interpreted to include a range of error unless otherwise explicitly stated.

[0044] Unless otherwise defined, all terms used herein, including technical and scientific terms, shall have the same meaning as commonly understood by one of ordinary skill in the art to which the inventive concept pertains. It should also be understood that terms such as those defined in commonly used dictionaries should be interpreted as having the same meaning as their meaning in the context of the relevant field, and shall not be interpreted as having an idealized or overly formal meaning, unless expressly defined herein.

[0045] As used herein, terms such as “implementation,” “example,” “aspect,” etc., should not be construed as any aspect or design described being better or superior to other aspects or designs.

[0046] Furthermore, the term "or" means "inclusive or," not "exclusive or." That is, unless otherwise stated or clear from the context, the statement "x uses a or b" implies any kind of natural inclusive permutation.

[0047] The terms used in the following description are chosen to be common terms in the relevant technical field. However, other terms may exist depending on the development and / or changes in technology, conventions, and the preferences of those skilled in the art. Therefore, the terms used in the following description should not be construed as limiting the technical concept, but rather as examples of terms used to describe implementation methods.

[0048] Furthermore, in certain cases, the terminology may be arbitrarily chosen by the applicant, and in such cases, its detailed meaning will be described in the corresponding descriptive section. Therefore, the terminology used in the following description should not be understood simply based on the name of the term, but rather on its meaning and its context throughout the specific embodiments.

[0049] As used in this article, the term "halogen" or "halogen" includes fluorine, chlorine, bromine, and iodine.

[0050] As used herein, the term "alkyl" refers to both straight-chain and branched alkyl groups. Unless otherwise stated, an alkyl group comprises 1 to 20 carbon atoms and includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and the like. Furthermore, alkyl groups may optionally be substituted.

[0051] As used herein, the term "cycloalkyl" refers to a cyclic alkyl group. Unless otherwise stated, a cycloalkyl group contains 3 to 20 carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, etc. Furthermore, cycloalkyl groups may optionally be substituted.

[0052] As used herein, the term "alkenyl" refers to both straight-chain and branched alkenyl groups. Unless otherwise stated, alkenyl groups contain 2 to 20 carbon atoms. Furthermore, alkenyl groups may optionally be substituted.

[0053] As used herein, the term "cycloalkenyl" refers to a cyclic alkenyl group. Unless otherwise stated, a cycloalkenyl group contains 3 to 20 carbon atoms. Furthermore, the cycloalkenyl group may optionally be substituted.

[0054] As used herein, the term "alkynyl" refers to both straight-chain and branched alkynyl groups. Unless otherwise stated, an alkynyl group contains 2 to 20 carbon atoms. Furthermore, the alkynyl group may optionally be substituted.

[0055] As used herein, the term "cycloynyl" refers to a cyclic ynyl group. Unless otherwise stated, a cycloynyl group contains 3 to 20 carbon atoms. Furthermore, the cycloynyl group may optionally be substituted.

[0056] As used herein, the terms "aralkyl" and "arylalkyl" are used interchangeably and refer to alkyl groups having an aromatic group as a substituent. Unless otherwise stated, aralkyl groups contain 2 to 60 carbon atoms. Furthermore, aralkyl groups may optionally be substituted.

[0057] As used herein, the terms "aryl" and "aromatic group" have the same meaning. Aryl groups include monocyclic and polycyclic groups. Polycyclic groups can include "fused rings," in which two or more rings are fused together such that two carbon atoms are shared by two adjacent rings. Unless otherwise stated, aryl groups contain 5 to 60 carbon atoms. Furthermore, aryl groups may optionally be substituted.

[0058] As used herein, the term "heterocyclic group" refers to a group in which at least one carbon atom constituting an aryl, cycloalkyl, cycloalkenyl, cycloynyl, aralkyl (arylalkyl), or arylamino group is substituted with a heteroatom such as oxygen (O), nitrogen (N), or sulfur (S). Referring to the above definition, a heterocyclic group may include heteroaryl, heterocycloalkyl, heterocycloalkenyl, heterocycloynyl, heteroarylalkyl (heteroarylalkyl), or heteroarylamino groups. Unless otherwise stated, a heterocyclic group comprises 2 to 60 carbon atoms. Furthermore, the heterocyclic group may optionally be substituted.

[0059] Unless otherwise stated, the term “carbocyclic” as used herein may be used to include all alicyclic groups such as “cycloalkyl”, “cycloalkenyl” and “cycloynyl”, as well as aromatic groups such as “aryl”.

[0060] As used herein, the terms “heteroalkyl,” “heteroalkenyl,” “heteroynyl,” or “heteroaryl (heteroarylalkyl)” mean that at least one carbon atom constituting a “heteroalkyl,” “heteroalkenyl,” “heteroynyl,” or “heteroaryl (heteroarylalkyl)” is substituted with a heteroatom such as oxygen (O), nitrogen (N), or sulfur (S). Furthermore, heteroalkyl, heteroalkenyl, heteroynyl, or heteroaryl (heteroarylalkyl) may optionally be substituted.

[0061] As used herein, the terms "alkylamino," "aralkylamino," "arylamino," or "heteroarylamino" refer to an amino group substituted with an alkyl, aralkyl, aryl, or heteroaryl group. In this respect, the amino group can include all primary, secondary, and tertiary amines. Furthermore, alkylamino, aralkylamino, arylamino, and heteroarylamino groups may optionally be substituted.

[0062] As used herein, the terms “alkylsilyl,” “arylsilyl,” “alkoxy,” “aryloxy,” “alkathio,” or “arylthio” mean that the silyl, oxy, and thio groups are each substituted with one of the alkyl and aryl groups. Furthermore, alkylsilyl, arylsilyl, alkoxy, aryloxy, alkathio, and arylthio may optionally be substituted.

[0063] As used herein, the term "substituted" refers to a non-hydrogen (H) substituent bonded to the corresponding carbon. When multiple substituents are present, the substituents may be the same as or different from each other.

[0064] Unless otherwise specified herein, substituents may be selected from the group consisting of: deuterium, halides, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof.

[0065] Unless otherwise specified, there are no particular restrictions on the position where substitution occurs, as long as the hydrogen atom can be substituted by a substituent at that position. When two or more substituents are present, i.e., multiple substituents, the substituents can be the same as or different from each other.

[0066] Unless otherwise stated, the subjects and substituents defined in this disclosure may be the same as or different from each other.

[0067] The structure of the organometallic compound according to this disclosure and the organic light-emitting diode comprising the organometallic compound will be described in detail below.

[0068] Conventionally, organometallic compounds have been used as dopants in the emitting layer of organic light-emitting diodes (OLEDs). For example, structures such as 2-phenylpyridine or 2-phenylquinoline are recognized as host ligand structures for organometallic compounds. However, such conventional luminescent dopants have limitations in improving the efficiency and lifetime of OLEDs. Therefore, there is a need to develop a novel luminescent doping material. Accordingly, the inventors of this disclosure have obtained a luminescent doping material capable of further improving the efficiency and lifetime of OLEDs, and thus this disclosure is completed.

[0069] Specifically, an organometallic compound according to one embodiment of this disclosure may be represented by the following chemical formula I, wherein the host ligand of formula I has a ring (pyridine ring or pyrimidine ring) structure, wherein at least one of the two rings connected to the central coordinating metal (M) contains nitrogen (N). Furthermore, aromatic rings and alicyclic rings may be fused to the nitrogen-containing (N) ring to enhance the rigidity of the compound molecule and obtain a stable structure.

[0070] The inventors of this disclosure have experimentally determined that when the doping material of the phosphorescent layer of an organic light-emitting diode (OLED) includes an organometallic compound represented by chemical formula I, the luminous efficiency and lifetime of the OLED are improved, and its operating voltage is reduced, thus completing this disclosure.

[0071] Organometallic compounds with the above-described characteristics according to this disclosure can be represented by the following chemical formula I.

[0072] [Chemical Formula I]

[0073]

[0074] In the above chemical formula I,

[0075] M can represent a centrally coordinated metal, and includes one selected from the group consisting of: molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt), and gold (Au).

[0076] A can represent a ring structure selected from pyridine and pyrimidine, wherein the ring structure is optionally substituted with deuterium.

[0077] R1 through R8 can each independently represent one selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, and substituted or unsubstituted C4 to C20 bicyclic alkyl.

[0078] R9 can each independently represent one selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, halogen, cyano, and alkoxy.

[0079] Optionally, when each of R1 to R9 is substituted, the substituents of each of R1 to R9 may be independently selected from the group consisting of deuterium, halogens, and substituted or unsubstituted C3 to C10 cycloalkyl groups, and when the number of substituents in each of R1 to R9 is at least two, the substituents may be the same or different from each other.

[0080] Y can represent a group selected from the following: BR 10 CR 10 R 11 C=O, CNR 10 SiR 10 R 11 NR 10 PR 10 AsR 10 SbR 10 P(O)R 10 P(S)R 10 、P(Se)R 10 As(O)R 10 As(S)R 10 As(Se)R 10 、Sb(O)R 10 、Sb(S)R 10 、Sb(Se)R 10, O, S, Se, Te, SO, SO2, SeO, SeO2, TeO and TeO2,

[0081] X1 to X4 can each independently represent a selection from CR 12 And one of nitrogen (N),

[0082] Optionally, the substituents R of X1 to X4 12 Two adjacent substituents can fused together to form a five- or six-membered aromatic ring structure, and optionally, the aromatic ring structure can be substituted with deuterium.

[0083] R 10 To R 12 Each can independently represent one selected from the group consisting of: hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C1 to C20 heteroalkyl, substituted or unsubstituted C7 to C20 arylalkyl, substituted or unsubstituted C2 to C20 alkenyl. Substituted or unsubstituted C3 to C20 cycloalkenyl, substituted or unsubstituted C1 to C20 heteroalkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C1 to C20 alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphinyl groups.

[0084] Optionally, when R 10 To R 12 When each one is replaced, R 10 To R 12 The substituents of each can be independently chosen from one of the groups consisting of deuterium and halogens, and when R 10 To R 12 When each of them has at least two substituents, the substituents can be the same or different from each other.

[0085] It can represent bidentate ligands.

[0086] m can be an integer of 1, 2 or 3, n can be an integer of 0, 1 or 2, m+n can be the oxidation number of metal M, and p can be 2.

[0087] In an organometallic compound according to one embodiment of the present disclosure, the auxiliary ligand binding to the central coordinating metal may be a bidentate ligand. Bidentate ligands can contain electron donors. Electron donor-assisted ligands can increase the electron density of the central coordinating metal, thereby lowering the MLCT (metal-to-ligand charge transfer) energy and increasing... 3 MLCT for T 1 The percentage contribution of the state. As a result, organic light-emitting diodes (OLEDs) comprising organometallic compounds, including those of the present disclosure, can achieve improved light-emitting characteristics, such as high luminous efficiency and high external quantum efficiency.

[0088] According to one embodiment of this disclosure, R1 to R8 may each independently represent one selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C1 to C10 straight-chain alkyl, and substituted or unsubstituted C3 to C10 branched alkyl.

[0089] According to one embodiment of this disclosure, an organometallic compound represented by chemical formula I can be represented by one of the following groups of chemical formulas I-1 and I-2:

[0090]

[0091] Among them, in chemical formulas I-1 and I-2,

[0092] Z3 through Z7 can each independently represent one selected from the group consisting of: hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C1 to C20 heteroalkyl, substituted or unsubstituted C7 to C20 arylalkyl, substituted or unsubstituted C 2 to C20 alkenyl, substituted or unsubstituted C3 to C20 cycloalkenyl, substituted or unsubstituted C1 to C20 heteroalkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C1 to C20 alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphinyl.

[0093] Z8 and Z9 can each independently represent one selected from oxygen (O) and nitrogen (NRz), where Rz represents one selected from the group consisting of: hydrogen, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, and substituted or unsubstituted C3 to C20 cycloalkyl.

[0094] According to one embodiment of this disclosure, Z3 to Z7 may each independently represent one selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 straight-chain alkyl, and substituted or unsubstituted C3 to C10 branched alkyl.

[0095] According to one embodiment of this disclosure, Z3 and Z7 may be identical to each other, and Z4 and Z6 may be identical to each other, thereby enabling the auxiliary ligand to have a symmetrical structure.

[0096] According to one embodiment of this disclosure, a compound represented by chemical formula I-1 may include a compound represented by one of the following chemical formulas: I-1-(1), I-1-(2), I-1-(3), I-1-(4), I-1-(5), and I-1-(6):

[0097]

[0098]

[0099] According to one embodiment of this disclosure, a compound represented by chemical formula I-2 may include a compound represented by one of the following chemical formulas: I-2-(1), I-2-(2), I-2-(3), I-2-(4), I-2-(5), and I-2-(6):

[0100]

[0101]

[0102]

[0103] According to one embodiment of this disclosure, A may be a cyclic structure of pyridine, wherein the cyclic structure is optionally replaced by deuterium.

[0104] According to one embodiment of this disclosure, M may be iridium (Ir). Phosphorescence can be effectively obtained at room temperature using iridium (Ir) or platinum (Pt) metal complexes having large atomic numbers. Therefore, in the organometallic compound according to one embodiment of this disclosure, the central coordinating metal (M) may preferably be iridium (Ir) or platinum (Pt), more preferably iridium (Ir). However, this disclosure is not limited thereto.

[0105] According to one embodiment of this disclosure, Y can be one of O (oxygen), sulfur (S), and selenium (Se). However, this disclosure is not limited thereto.

[0106] According to one embodiment of this disclosure, at least one of R9 may not be hydrogen. This may mean that at least one of R9 may be substituted with a substituent selected from the group consisting of, other than hydrogen: deuterium, substituted or unsubstituted C1 to C20 straight-chain alkyl, substituted or unsubstituted C3 to C20 branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, halogen, cyano, and alkoxy.

[0107] According to one embodiment of this disclosure, R 10 To R 12 Each can independently represent one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, nitro, alkoxy, amino, substituted or unsubstituted C1 to C10 straight-chain alkyl, substituted or unsubstituted C3 to C10 branched alkyl, and substituted or unsubstituted C3 to C10 cycloalkyl.

[0108] According to one embodiment of this disclosure, R 12 Each can independently represent one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, nitro, alkoxy, amino, substituted or unsubstituted C1 to C10 straight-chain alkyl, substituted or unsubstituted C3 to C10 branched alkyl, and substituted or unsubstituted C3 to C10 cycloalkyl.

[0109] Specific examples of compounds represented by Formula I of this disclosure may include one selected from the group consisting of compounds 1 to 331. However, this disclosure is not limited thereto, as long as the compound falls within the definition of Formula I:

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] According to one embodiment of the present disclosure, an organometallic compound represented by chemical formula I of the present disclosure can be used as a dopant material to achieve red phosphorescence or green phosphorescence, preferably as a dopant material to achieve red phosphorescence.

[0125] Reference Figure 1 According to one embodiment of this disclosure, an organic light-emitting diode (OLED) 100 may be provided, comprising a first electrode 110; a second electrode 120 facing the first electrode 110; and an organic layer 130 disposed between the first electrode 110 and the second electrode 120. The organic layer 130 may include a light-emitting layer 160, which may include a matrix material 160' and a dopant 160'. The dopant 160' may be made of an organometallic compound represented by chemical formula I. Furthermore, in the OLED 100, the organic layer 130 disposed between the first electrode 110 and the second electrode 120 may be formed by sequentially stacking a hole injection layer 140 (HIL), a hole transport layer 150 (HTL), a light-emitting layer 160 (EML), an electron transport layer 170 (ETL), and an electron injection layer 180 (EIL) on the first electrode 110. The second electrode 120 may be formed on the electron injection layer 180, and a protective layer (not shown) may be formed thereon.

[0126] Furthermore, despite Figure 1 It is not shown in the figure, but at least one of the hole transport assist layer and the electron blocking layer may be further added between the hole transport layer 150 and the light-emitting layer 160.

[0127] The hole transport auxiliary layer can contain compounds with good hole transport properties and can reduce the HOMO energy level difference between the hole transport layer 150 and the emissive layer 160, thereby modulating the hole injection performance. Therefore, hole accumulation at the interface between the hole transport auxiliary layer and the emissive layer 160 can be reduced, thus reducing the exciton quenching phenomenon caused by polarons disappearing at the interface. This reduces device degradation and stabilizes the device, thereby improving its efficiency and lifetime.

[0128] An electron blocking layer controls the movement of electrons and their binding with holes to prevent electrons from entering the hole transport layer, thereby improving the efficiency and lifetime of organic light-emitting diodes (OLEDs). Materials constituting the electron blocking layer can be selected from the group consisting of: 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, TAPC, MTDATA, mCP, mCBP, CuPC, DNTPD, TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene, and the like. Furthermore, the electron blocking layer may include inorganic compounds. The inorganic compounds may be selected from the group consisting of: halides, such as LiF, NaF, KF, RbF, CsF, FrF, MgF2, CaF2, SrF2, BaF2, LiCl, NaCl, KCl, RbCl, CsCl, FrCl, etc.; and oxides, such as Li2O, Li2O2, Na2O, K2O, Rb2O, Rb2O2, Cs2O, Cs2O2, LiAlO2, LiBO2, LiTaO3, LiNbO3, LiWO4, Li2CO, NaWO4, KAlO2, K2SiO3, B2O5, Al2O3, SiO2, etc. However, this disclosure is not limited to these.

[0129] The first electrode 110 can serve as a positive electrode and can be made of ITO, IZO, tin oxide, or zinc oxide, which are conductive materials with relatively large work function values. However, this disclosure is not limited thereto.

[0130] The second electrode 120 may serve as the negative electrode and may include Al, Mg, Ca, or Ag, or alloys or combinations thereof, as a conductive material having a relatively small work function value. However, this disclosure is not limited thereto.

[0131] Hole injection layer 140 may be located between first electrode 110 and hole transport layer 150. Hole injection layer 140 may have the function of improving the interface properties between first electrode 110 and hole transport layer 150, and may be selected from materials with suitable conductivity. Hole injection layer 140 may include 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-triphenylphenyl-1,4-diamine). Preferably, hole injection layer 140 may include N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylphenyl-1,4-diamine). However, this disclosure is not limited thereto.

[0132] The hole transport layer 150 may be located near the light-emitting layer and between the first electrode 110 and the light-emitting layer 160. The material of the hole transport layer 150 may include compounds selected from the group consisting of: TPD, NPD, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-4-amine, etc. Preferably, the hole transport layer 150 may include NPB. However, this disclosure is not limited thereto.

[0133] According to this disclosure, in order to improve the luminous efficiency of diode 100, a light-emitting layer 160 can be formed by doping the matrix material 160' with an organometallic compound represented by chemical formula I as a dopant 160". The dopant 160" can be used as a green light-emitting material or a red light-emitting material, and is preferably used as a red phosphorescent material.

[0134] The doping concentration of the dopant 160" according to this disclosure can be adjusted to a range of 1 to 30 wt% based on the total weight of the matrix material 160'. However, this disclosure is not limited thereto. For example, the doping concentration can be in the range of 2 to 20 wt%, such as 3 to 15 wt%, such as 5 to 10 wt%, such as 3 to 8 wt%, such as 2 to 7 wt%, such as 5 to 7 wt%, or such as 5 to 6 wt%.

[0135] The light-emitting layer 160 according to this disclosure comprises a matrix material 160' known in the art, and simultaneously comprises an organometallic compound represented by chemical formula I as a dopant 160', thus achieving the effects of this disclosure. For example, according to this disclosure, the matrix material 160' may comprise a compound containing a carbazole group, and may preferably comprise a matrix material selected from the group consisting of: CBP (carbazole biphenyl), mCP (1,3-bis(carbazole-9-yl)), etc. However, this disclosure is not limited thereto.

[0136] Furthermore, the electron transport layer 170 and the electron injection layer 180 can be sequentially stacked between the light-emitting layer 160 and the second electrode 120. The material of the electron transport layer 170 needs to have high electron mobility so that electrons can be stably supplied to the light-emitting layer under smooth electron transport.

[0137] For example, the material of electron transport layer 170 may be well known in the art and may include one selected from the group consisting of: Alq3 (tris(8-hydroxyquinoline)aluminum), Liq (lithium 8-hydroxyquinoline), PBD (2-(4-biphenyl)-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-hydroxyquinoline)-4-(phenylphenol)aluminum), SAlq, TPBi ((2,2',2-(1,3,5-benzotriphenyl)-tris( 1-Phenylon-1-H-benzimidazole), (2,2',2-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)), oxadiazole, triazole, phenanthrene, benzoxazole, benzothiazole, and 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl]-1-phenyl-1H-benzimidazole. Preferably, the material of the electron transport layer 170 may include 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl]-1-phenyl-1H-benzimidazole. However, this disclosure is not limited thereto.

[0138] An electron injection layer 180 is used to facilitate electron injection. The material of the electron injection layer can be a compound well-known in the art and can include compounds selected from the group consisting of: Alq3 (tris(8-hydroxyquinoline)aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq, etc. However, this disclosure is not limited thereto. Alternatively, the electron injection layer 180 can be made of a metal compound. The metal compound can include, for example, one or more selected from the group consisting of: Liq, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2, and RaF2. However, this disclosure is not limited thereto.

[0139] The organic light-emitting diode (OLED) according to this disclosure can be implemented as a white OLED with a series structure. A series OLED according to an illustrative embodiment of this disclosure can be formed in a structure in which adjacent light-emitting layers of two or more light-emitting stacks are connected to each other via a charge-generating layer (CGL). The OLED may include at least two light-emitting stacks disposed on a substrate, each of the at least two light-emitting stacks including a first electrode and a second electrode facing each other, and a light-emitting layer disposed between the first electrode and the second electrode to emit light of a specific wavelength. Multiple light-emitting stacks may emit light of the same color or different colors. Furthermore, a light-emitting stack may include one or more light-emitting layers, and multiple light-emitting layers may emit light of the same color or different colors.

[0140] In this configuration, the light-emitting layer included in at least one of the plurality of light-emitting stacks may contain an organometallic compound represented by Formula I as a dopant according to this disclosure. Adjacent light-emitting stacks in the tandem structure may be connected to each other via a charge-generating layer CGL comprising an N-type charge-generating layer and a P-type charge-generating layer.

[0141] According to some implementations of this disclosure Figure 2 and Figure 3 These are schematic cross-sectional views of an organic light-emitting diode (OLED) with a series structure of two light-emitting layers and an organic light-emitting diode with a series structure of three light-emitting layers, respectively.

[0142] like Figure 2 As shown, the organic light-emitting diode 100 according to this disclosure includes a first electrode 110 and a second electrode 120 facing each other, and an organic layer 230 located between the first electrode 110 and the second electrode 120. The organic layer 230 may be located between the first electrode 110 and the second electrode 120, and may include a first light-emitting stack ST1 containing a first light-emitting layer 261, a second light-emitting stack ST2 located between the first light-emitting stack ST1 and the second electrode 120 and containing a second light-emitting layer 262, and a charge-generating layer CGL located between the first light-emitting stack ST1 and the second light-emitting stack ST2. The charge-generating layer CGL may include an N-type charge-generating layer 291 and a P-type charge-generating layer 292. At least one of the first light-emitting layer 261 and the second light-emitting layer 262 may contain an organometallic compound represented by chemical formula I according to this disclosure as a dopant. For example, such as... Figure 2 As shown, the second light-emitting layer 262 of the second light-emitting stack ST2 may comprise a matrix material 262' and a dopant 262' made of an organometallic compound represented by chemical formula I, doped into the matrix material 262'. Although in Figure 2Not shown, but each of the first light-emitting stack ST1 and the second light-emitting stack ST2 may further include an additional light-emitting layer in addition to each of the first light-emitting layer 261 and the second light-emitting layer 262.

[0143] like Figure 3 As shown, the organic light-emitting diode 100 according to this disclosure includes a first electrode 110 and a second electrode 120 facing each other, and an organic layer 330 located between the first electrode 110 and the second electrode 120. The organic layer 330 may be located between the first electrode 110 and the second electrode 120, and may include a first light-emitting stack ST1 containing a first light-emitting layer 261, a second light-emitting stack ST2 containing a second light-emitting layer 262, a third light-emitting stack ST3 containing a third light-emitting layer 263, a first charge-generating layer CGL1 located between the first light-emitting stack ST1 and the second light-emitting stack ST2, and a second charge-generating layer CGL2 located between the second light-emitting stack ST2 and the third light-emitting stack ST3. The first charge-generating layer CGL1 may include an N-type charge-generating layer 291 and a P-type charge-generating layer 292. The second charge-generating layer CGL2 may include an N-type charge-generating layer 293 and a P-type charge-generating layer 294. At least one of the first light-emitting layer 261, the second light-emitting layer 262, and the third light-emitting layer 263 may contain an organometallic compound represented by chemical formula I as a dopant according to this disclosure. For example, such as Figure 3 As shown, the second light-emitting layer 262 of the second light-emitting stack ST2 may comprise a matrix material 262' and a dopant 262' made of an organometallic compound represented by chemical formula I, which is doped into the matrix material 262'. Although Figure 3 Not shown, but each of the first light-emitting stack ST1, the second light-emitting stack ST2 and the third light-emitting stack ST3 may further include an additional light-emitting layer in addition to each of the first light-emitting layer 261, the second light-emitting layer 262 and the third light-emitting layer 263.

[0144] Furthermore, an organic light-emitting diode according to an embodiment of the present disclosure may include a series structure in which four or more light-emitting layers and three or more charge-generating layers are disposed between a first electrode and a second electrode.

[0145] The organic light-emitting diodes (OLEDs) according to this disclosure can be used in organic light-emitting display devices, display devices including organic light-emitting diodes, or lighting devices. In one embodiment, Figure 4 This is a schematic cross-sectional view of an organic light-emitting display device that includes an organic light-emitting diode as its light-emitting element according to some embodiments of the present disclosure.

[0146] like Figure 4As shown, the organic light-emitting display device 3000 includes a substrate 3010, an organic light-emitting diode 4000, and an encapsulation film 3900 covering the organic light-emitting diode 4000. A driving thin-film transistor Td, which serves as a driving element, and the organic light-emitting diode 4000 connected to the driving thin-film transistor Td are located on the substrate 3010.

[0147] Despite Figure 4 Although not explicitly shown, gate lines and data lines that intersect each other to define pixel areas, power lines that extend parallel to and are separated from one of the gate lines and data lines, switching thin-film transistors connected to the gate lines and data lines, and storage capacitors connected to an electrode of the thin-film transistors and the power lines are further formed on substrate 3010.

[0148] The driving thin-film transistor Td is connected to the switching thin-film transistor and includes a semiconductor layer 3100, a gate 3300, a source 3520, and a drain 3540.

[0149] Semiconductor layer 3100 can be formed on substrate 3010 and can be made of oxide semiconductor material or polysilicon. When semiconductor layer 3100 is made of oxide semiconductor material, a light-shielding pattern (not shown) can be formed below semiconductor layer 3100. The light-shielding pattern prevents light from incident into semiconductor layer 3100, thereby preventing semiconductor layer 3100 from deteriorating due to light. Alternatively, semiconductor layer 3100 can be made of polysilicon. In this case, the two edges of semiconductor layer 3100 can be doped with impurities.

[0150] A gate insulating layer 3200 made of insulating material is formed over the entire surface of the substrate 3010 and on the semiconductor layer 3100. The gate insulating layer 3200 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

[0151] A gate 3300, made of a conductive material such as metal, is formed on the gate insulating layer 3200 and corresponds to the center of the semiconductor layer 3100. The gate 3300 is connected to a switching thin-film transistor.

[0152] An interlayer insulating layer 3400 made of insulating material is formed over the entire surface of the substrate 3010 and on the gate 3300. The interlayer insulating layer 3400 may be made of inorganic insulating materials such as silicon oxide or silicon nitride, or organic insulating materials such as benzocyclobutene or photo-acryl.

[0153] The interlayer insulating layer 3400 has a first semiconductor layer contact hole 3420 and a second semiconductor layer contact hole 3440 defined therein, which respectively expose two opposite sides of the semiconductor layer 3100. The first semiconductor layer contact hole 3420 and the second semiconductor layer contact hole 3440 are located on two opposite sides of the gate 3300 and spaced apart from the gate 3300.

[0154] Source 3520 and drain 3540, made of a conductive material such as metal, are formed on interlayer insulating layer 3400. Source 3520 and drain 3540 are located around gate 3300 and spaced apart from each other, and contact two opposite sides of semiconductor layer 3100 via first semiconductor layer contact hole 3420 and second semiconductor layer contact hole 3440, respectively. Source 3520 is connected to a power supply line (not shown).

[0155] Semiconductor layer 3100, gate 3300, source 3520 and drain 3540 constitute driving thin film transistor Td. Driving thin film transistor Td has a coplanar structure, wherein gate 3300, source 3520 and drain 3540 are located on top of semiconductor layer 3100.

[0156] Alternatively, the driving thin-film transistor Td can have an anti-interleaved structure, where the gate is located below the semiconductor layer, while the source and drain 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 (not shown) can have substantially the same structure as the driving thin-film transistor (Td).

[0157] In one example, the organic light-emitting display device 3000 may include a color filter 3600 that absorbs light generated from an electroluminescent element (light-emitting diode) 4000. For example, the color filter 3600 may absorb red (R), green (G), blue (B), and white (W) light. In this case, the light-absorbing red, green, and blue color filter patterns may be formed individually in different pixel regions. Each of these color filter patterns may be configured to overlap with each organic layer 4300 of the organic light-emitting diode 4000 to emit light corresponding to the wavelength band of each color filter. Using the color filter 3600 allows the organic light-emitting display device 3000 to achieve full-color illumination.

[0158] For example, when the organic light-emitting display device 3000 is bottom-emitting, the light-absorbing color filter 3600 can be located on the portion of the interlayer insulating layer 3400 corresponding to the organic light-emitting diode 4000. In an alternative embodiment, when the organic light-emitting display device 3000 is top-emitting, the color filter can be located on top of the organic light-emitting diode 4000, that is, on top of the second electrode 4200. For example, the color filter 3600 can be formed to have a thickness of 2 to 5 μm.

[0159] In one example, a passivation layer 3700 is formed having a drain contact hole 3720 that defines a drain 3540 therein that exposes the driving thin film transistor Td, to cover the driving thin film transistor Td.

[0160] On the passivation layer 3700, each first electrode 4100 connected to the drain 3540 of the driving thin film transistor Td via a drain contact hole 3720 is individually formed in each pixel region.

[0161] The first electrode 4100 can serve as the positive electrode (anode) and can be made of a conductive material with a relatively large work function value. For example, the first electrode 4100 can be made of a transparent conductive material such as ITO, IZO or ZnO.

[0162] In one example, when the organic light-emitting display device 3000 is a top-emitting type, a reflective electrode or reflective layer may be further formed below the first electrode 4100. For example, the reflective electrode or reflective layer may be made of one of aluminum (Al), silver (Ag), nickel (Ni), and aluminum-palladium-copper (APC) alloys.

[0163] A dam layer 3800 covering the edge of the first electrode 4100 is formed on the passivation layer 3700. The dam layer 3800 exposes the center of the first electrode 4100 corresponding to the pixel region.

[0164] An organic layer 4300 is formed on the first electrode 4100. If desired, the organic light-emitting diode 4000 may have a series structure. Regarding the series structure, reference can be made to some embodiments illustrating this disclosure. Figures 2 to 4 And the description above.

[0165] The second electrode 4200 is formed on the substrate 3010 on which the organic layer 4300 has been formed. The second electrode 4200 is disposed above the entire surface of the display area and is made of a conductive material with a relatively small work function value, and can be used as a negative electrode (cathode). For example, the second electrode 4200 can be made of one of aluminum (Al), magnesium (Mg), and aluminum-magnesium alloy (Al-Mg).

[0166] The first electrode 4100, the organic layer 4300, and the second electrode 4200 constitute an organic light-emitting diode 4000.

[0167] An encapsulation film 3900 is formed on the second electrode 4200 to prevent external moisture from penetrating the organic light-emitting diode 4000. Although in Figure 4 It is not explicitly shown that the encapsulation film 3900 may have a three-layer structure in which a first inorganic layer, an organic layer, and an inorganic layer are stacked sequentially. However, this disclosure is not limited thereto.

[0168] In the following sections, examples of preparation and current embodiments of this disclosure will be described. However, the following current embodiments are merely one example of this disclosure. This disclosure is not limited thereto.

[0169] Preparation Example

[0170] <Preparation Example 1: Preparation of Compound 1>

[0171]

[0172] Preparation of compound 1-1

[0173] 6-Bromo-7-methoxy-1,2,3,4-tetrahydronaphthalene (10 g, 41.4 mmol, 1.0 eq) was dissolved in 1,4-dioxane to prepare a solution. Then, bis(pinacol)diborane (15.8 g, 62.2 mmol, 1.5 eq), Pd(dppf)Cl2 (1.5 g, 2.07 mmol, 0.05 eq), and KOAc (12.1 g, 124 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. The organic layer was then purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 1-1 (11.7 g, 98%) was thus obtained.

[0174] MS (m / z): 288.19

[0175] Preparation of compounds 1-2

[0176] Compound 1-1 (11.7 g, 40.5 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 4-bromo-2-chloro-3-fluoropyridine (11.7 g, 40.5 mmol, 1.0 eq), Pd(PPh3)4 (2.3 g, 2.02 mmol, 0.05 eq), and K2CO3 (16.7 g, 121 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, compound 1-2 (10.3 g, 88%) was obtained.

[0177] MS (m / z): 291.75

[0178] Preparation of compounds 1-3

[0179] Compounds 1-2 (10.3 g, 35.6 mmol, 1.0 eq) were dissolved in dichloromethane to prepare a solution, and BBr3 was slowly added to it at 0°C, followed by stirring for 1 hour. After the reaction was complete, methanol was slowly added to it at 0°C, followed by extraction with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent to obtain compounds 1-3 (9.4 g, 95%).

[0180] MS (m / z): 277.72

[0181] Preparation of compounds 1-4

[0182] Compounds 1-3 (9.4 g, 33.8 mmol, 1.0 eq) were dissolved in N-methyl-2-pyrrolidone to prepare a solution. K₂CO₃ (14.0 g, 101.4 mmol, 3.0 eq) was then added, followed by stirring at 120 °C for 12 hours. After the reaction was complete, the mixture was extracted with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO₄, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compounds 1-4 (6.2 g, 72%).

[0183] MS (m / z): 257.72

[0184] Preparation of compounds 1-5

[0185] Compounds 1-4 (6.2 g, 24.3 mmol, 1.0 eq) were dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (3.2 g, 26.7 mmol, 1.1 eq), Pd(PPh3)4 (1.4 g, 1.21 mmol, 0.05 eq) and K2CO3 (10.0 g, 72.9 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, compounds 1-5 (6.7 g, 93%) were obtained.

[0186] MS (m / z): 299.37

[0187] Preparation of compounds 1-6

[0188] Compounds 1-5 (6.7 g, 22.6 mmol, 1.8 eq) and iridium(III) chloride hydrate (3.7 g, 12.5 mmol, 1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 h under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to obtain compounds 1-6 (8.6 g, 93%).

[0189] MS (m / z): 1648.79

[0190] Preparation of Compound 1

[0191] Compounds 1-6 (8.6 g, 21.0 mmol, 1.0 eq) and 2,6-dimethylheptane-3,5-dione (6.5 g, 42.0 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Compound 1 (6.2 g, 63%) was thus obtained.

[0192] MS (m / z): 944.16

[0193] <Preparation Example 2: Preparation of Compound 7>

[0194]

[0195] Preparation of compound 7-1

[0196] Compound 1-4 (10.0 g, 38.8 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(3-(tert-butyl)phenyl)-4,4,5-5-tetramethyl-1,3,2-dioxaborane (11.1 g, 42.6 mmol, 1.1 eq), Pd(PPh3)4 (2.2 g, 1.94 mmol, 0.05 eq), and K2CO3 (16.0 g, 116.4 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent to obtain compound 7-1 (12.5 g, 91%).

[0197] MS (m / z): 355.48

[0198] Preparation of compound 7-2

[0199] Compound 7-1 (12.5 g, 35.3 mmol, 1.8 eq) and iridium(III) chloride hydrate (5.8 g, 19.6 mmol, 1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 h under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to obtain compound 7-2 (15.0 g, 95%).

[0200] MS (m / z): 1813.09

[0201] Preparation of compound 7

[0202] Compound 7-2 (15 g, 33.5 mmol, 1.0 eq) and 2,6-dimethylheptane-3,5-dione (10.4 g, 67.0 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 7 (8.9 g, 52%) was thus obtained.

[0203] MS (m / z): 1026.31

[0204] <Preparation Example 3: Preparation of Compound 18>

[0205]

[0206] Preparation of compound 18-1

[0207] A solution was prepared by dissolving 6-bromo-7-methoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10 g, 33.6 mmol, 1.0 eq) in 1,4-dioxane. Then, bis(pinacol)diborane (12.8 g, 50.4 mmol, 1.5 eq), Pd(dppf)Cl2 (1.2 g, 1.68 mmol, 0.05 eq), and KOAc (9.9 g, 100 mmol, 3.0 eq) were added, followed by stirring at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 18-1 (11.3 g, 98%) was thus obtained.

[0208] MS (m / z): 344.30

[0209] Preparation of compound 18-2

[0210] Compound 18-1 (11.3 g, 32.9 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 4-bromo-2-chloro-3-fluoropyridine (6.9 g, 32.9 mmol, 1.0 eq), Pd(PPh3)4 (1.9 g, 1.64 mmol, 0.05 eq), and K2CO3 (13.6 g, 98.7 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, compound 18-2 (9.7 g, 85%) was obtained.

[0211] MS (m / z): 347.86

[0212] Preparation of compound 18-3

[0213] Compound 18-2 (9.7 g, 27.9 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and BBr3 was slowly added to it at 0 °C, followed by stirring for 1 hour. After the reaction was complete, methanol was slowly added to it at 0 °C, followed by extraction with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, compound 18-3 (8.9 g, 96%) was obtained.

[0214] MS (m / z): 333.83

[0215] Preparation of compound 18-4

[0216] Compound 18-3 (8.9 g, 26.7 mmol, 1.0 eq) was dissolved in N-methyl-2-pyrrolidone to prepare a solution, and then K₂CO₃ (11.0 g, 80.1 mmol, 3.0 eq) was added, followed by stirring at 120 °C for 12 h. After the reaction was complete, the mixture was extracted with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO₄, and then the solvent was removed by rotary evaporation. The mixture was then purified by column chromatography using dichloromethane and hexane as developing solvents. Compound 18-4 (6.6 g, 79%) was thus obtained.

[0217] MS (m / z): 313.83

[0218] Preparation of compound 18-5

[0219] Compound 18-4 (6.6 g, 21.0 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (2.8 g, 23.1 mmol, 1.1 eq), Pd(PPh3)4 (1.2 g, 1.05 mmol, 0.05 eq), and K2CO3 (8.7 g, 63.0 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, compound 18-5 (7.0 g, 94%) was obtained.

[0220] MS (m / z): 355.48

[0221] Preparation of compound 18-6

[0222] Compound 18-5 (7.0 g, 19.7 mmol, 1.8 eq) and iridium(III) chloride hydrate (3.2 g, 10.9 mmol, 1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to obtain compound 18-6 (8.3 g, 93%).

[0223] MS (m / z): 1828.12

[0224] Preparation of compound 18

[0225] Compound 18-6 (8.3 g, 18.3 mmol, 1.0 eq) and 2,6-dimethylheptane-3,5-dione (5.7 g, 36.9 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Compound 18 (6.1 g, 65%) was thus obtained.

[0226] MS (m / z): 1026.31

[0227] <Preparation Example 4: Preparation of Compound 31>

[0228]

[0229] Preparation of compound 31-1

[0230] Compound 18-4 (10.0 g, 31.8 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(3-(tert-butyl)phenyl)-4,4,5-5-tetramethyl-1,3,2-dioxaborane (10.8 g, 35.0 mmol, 1.1 eq), Pd(PPh3)4 (1.8 g, 1.59 mmol, 0.05 eq), and K2CO3 (13.1 g, 95.4 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, compound 31-1 (13.5 g, 92%) was obtained.

[0231] MS (m / z): 461.65

[0232] Preparation of compound 31-2

[0233] Compound 31-1 (13.5 g, 29.2 mmol, 1.8 eq) and iridium(III) chloride hydrate (4.8 g, 16.2 mmol, 1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 h under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to obtain compound 31-2 (16 g, 97%).

[0234] MS (m / z): 2267.83

[0235] Preparation of compound 31

[0236] Compound 31-2 (16 g, 28.3 mmol, 1.0 eq) and 2,6-dimethylheptane-3,5-dione (8.8 g, 56.6 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Compound 31 (9.2 g, 52%) was thus obtained.

[0237] MS (m / z): 1255.70

[0238] <Preparation Example 5: Preparation of Compound 40>

[0239]

[0240] Preparation Example 5: Preparation of Compound 40

[0241] Compound 40 was prepared in the same manner as compound 31 in Preparation Example 4, except that 2,2,6,6-tetramethylheptane-3,5-dione was used instead of 2,6-dimethylheptane-3,5-dione.

[0242] MS (m / z): 1283.75

[0243] <Preparation Example 6: Preparation of Compound 41>

[0244]

[0245] Compound 41 was obtained in the same manner as compound 31 in Preparation Example 4, except that 3,7-diethylnonane-4,6-dione was used instead of 2,6-dimethylheptane-3,5-dione.

[0246] MS (m / z): 1311.81

[0247] <Preparation Example 7: Preparation of Compound 42>

[0248]

[0249] Compound 42 was obtained in the same manner as compound 31 in Preparation Example 4, except that 3,7-diethyl-3,7-dimethylnonane-4,6-dione was used instead of 2,6-dimethylheptane-3,5-dione.

[0250] MS (m / z): 1339.86

[0251] <Preparation Example 8: Preparation of Compound 44>

[0252]

[0253] Compound 44 was obtained in the same manner as compound 31 in Preparation Example 4, except that 3,7-diethyl-3,7-dimethylnonane-4,6-dione-5-d was used instead of 2,6-dimethylheptane-3,5-dione.

[0254] MS (m / z): 1340.87

[0255] <Preparation Example 9: Preparation of Compound 53>

[0256]

[0257] Compound 53 was obtained in the same manner as compound 31 in Preparation Example 4, except that (Z)-3,7-diethyl-6-(isopropylimino)non-4-one was used instead of 2,6-dimethylheptane-3,5-dione.

[0258] MS (m / z): 1352.90

[0259] <Preparation Example 10: Preparation of Compound 59>

[0260]

[0261] Preparation of compound 59-1

[0262] 6-Bromo-5-methoxy-1,1,4-4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10 g, 33.6 mmol, 1.0 eq) was dissolved in 1,4-dioxane to prepare a solution. Then, bis(pinacol)diborane (1.5 eq), Pd(dppf)Cl2 (0.05 eq), and KOAc (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 59-1 (10.8 g, 94%) was thus obtained.

[0263] MS (m / z): 344.30

[0264] Preparation of compound 59-2

[0265] Compound 59-1 (10.8 g, 31.5 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 3-bromo-4-fluoropyridine (1.0 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 59-2 (8.2 g, 84%) was thus obtained.

[0266] MS (m / z): 313.42

[0267] Preparation of compound 59-3

[0268] Compound 59-2 (8.2 g, 26.4 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and then BBr3 (2 eq) was slowly added to it at 0 °C, followed by stirring for 1 hour. After the reaction was complete, methanol was slowly added to it at 0 °C, followed by extraction with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, compound 59-3 (7.2 g, 92%) was obtained.

[0269] MS (m / z): 299.39

[0270] Preparation of compound 59-4

[0271] Compound 59-3 (7.2 g, 24.2 mmol, 1.0 eq) was dissolved in N-methyl-2-pyrrolidone to prepare a solution. K₂CO₃ (3.0 eq) was then added, and the mixture was stirred at 120 °C for 12 hours. After the reaction was complete, the solution was extracted with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO₄, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Compound 59-4 (6.0 g, 90%) was thus obtained.

[0272] MS (m / z): 279.38

[0273] Preparation of compound 59-5

[0274] Compound 59-4 (6.0 g, 21.7 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution. Then, m-CPBA was added to the solution, and the mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was separated by chromatographic chromatography using distilled water and dichloromethane, and the organic layer was concentrated. The concentrated residue was dissolved in POCl3 (10 mL) to prepare a solution, and the mixture was stirred at 80 °C for 4 hours. After the reaction was complete, the POCl3 was removed by rotary evaporation, and then the mixture was neutralized by adding a saturated aqueous solution of NaHCO3. The mixture was separated by chromatographic chromatography using distilled water and dichloromethane, and the organic layer was dried over anhydrous MgSO4. The solvent was removed by rotary evaporation, and then purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 59-5 (5.5 g, 81%) was thus obtained.

[0275] MS (m / z): 313.83

[0276] Preparation of compound 59-6

[0277] Compound 59-5 (5.5 g, 17.5 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 59-6 (7.4 g, 92%) was thus obtained.

[0278] MS (m / z): 461.65

[0279] Preparation of compound 59-7

[0280] Compound 59-6 (7.4 g, 16.1 mmol, 1.8 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, compound 59-7 (8.4 g, 92%) was obtained.

[0281] MS (m / z): 2282.86

[0282] Preparation of compound 59

[0283] Compound 59-7 (8.4 g, 14.8 mmol, 1.0 eq) and 3,7-diethyl-3,7-dimethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then filtered. The solvent was removed from the filtrate by rotary evaporation. The residue was then purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, compound 59 (6.1 g, 61%) was obtained.

[0284] MS (m / z): 1352.88

[0285] <Preparation Example 11: Preparation of Compound 78>

[0286]

[0287] Preparation of compound 78-1

[0288] 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-thiol (10 g, 45.3 mmol) was dissolved in DMSO (100 mL) to prepare a solution. Cs₂CO₃ (1.2 eq), iodobenzene (0.1 eq), and CuMoO₄ (0.03 eq) were then added to the solution, and the mixture was stirred at 30 °C for 12 hours under nitrogen reflux. After the reaction was complete, the layers were separated using distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO₄, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using ethyl acetate and hexane as the developing solvent. Compound 78-1 (14 g, 90%) was thus obtained.

[0289] MS (m / z): 346.92

[0290] Preparation of compound 78-2

[0291] Compound 78-1 (14 g, 40.7 mmol) was dissolved in acetonitrile (CAN) to prepare a solution, and then t-BuONO (2 eq) was slowly added dropwise to this solution, followed by stirring at 0°C for 30 minutes. Then, copper powder (2 eq) was added to the reaction solution, and the mixture was stirred at 80°C for 3 hours. After the reaction was complete, the reaction solution was filtered. The filtrate was concentrated and purified by column chromatography using hexane as the developing solvent. This yielded compound 78-2 (4.1 g, 31%) and byproduct 78-2-1 (3.7 g, 28%).

[0292] MS (m / z): 329.89

[0293] Preparation of compound 78-3

[0294] Compound 78-2 (4.1 g, 12.6 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 78-3 (4.4 g, 94%) was thus obtained.

[0295] MS (m / z): 371.54

[0296] Preparation of compound 78-4

[0297] Compound 78-3 (4.4 g, 11.8 mmol, 1.8 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to obtain compound 78-4 (5.1 g, 92%).

[0298] MS (m / z): 1894.38

[0299] Preparation of compound 78

[0300] Compound 78-4 (5.1 g, 10.8 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 78 (3.3 g, 61%) was thus obtained.

[0301] MS (m / z): 1004.34

[0302] <Preparation Example 12: Preparation of Compound 82>

[0303]

[0304] Preparation of compound 82-2

[0305] Compound 82-1 (3.7 g, 11.2 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 82-2 (3.8 g, 92%) was thus obtained.

[0306] MS (m / z): 371.54

[0307] Preparation of compound 82-3

[0308] Compound 82-2 (3.8 g, 10.3 mmol, 1.8 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 h under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to obtain compound 82-3 (4.6 g, 93%).

[0309] MS (m / z): 1196.40

[0310] Preparation of compound 82

[0311] Compound 82-3 (4.6 g, 9.57 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Compound 82 (3.0 g, 61%) was thus obtained.

[0312] MS (m / z): 661.86

[0313] <Preparation Example 13: Preparation of Compound 102>

[0314]

[0315] Preparation of compound 102-1

[0316] Compound 78-2 (10 g, 30.3 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 102-1 (13.8 g, 95%) was thus obtained.

[0317] MS (m / z): 477.71

[0318] Preparation of compound 102-2

[0319] Compound 102-1 (13.8 g, 28.7 mmol, 1.8 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, compound 102-2 (15.4 g, 92%) was obtained.

[0320] MS(m / z): 2347.11

[0321] Preparation of compound 102

[0322] Compound 102-2 (15.4 g, 26.4 mmol, 1.0 eq) and 3,7-diethyl-3,7-dimethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Compound 102 (10.9 g, 60%) was thus obtained.

[0323] MS (m / z): 1385.00

[0324] <Preparation Example 14: Preparation of Compound 103>

[0325]

[0326] Compound 103 was obtained in the same manner as compound 102 in Preparation Example 13, except that (Z)-3,7-diethyl-6-hydroxynon-5-en-4-one-5-d was used instead of 3,7-diethyl-3,7-dimethylnonane-4,6-dione.

[0327] MS (m / z): 1357.95

[0328] <Preparation Example 15: Preparation of Compound 104>

[0329]

[0330] Compound 104 was obtained in the same manner as compound 102 in Preparation Example 13, except that (Z)-3,7-diethyl-6-hydroxy-3,7-dimethylnon-5-en-4-one-5-d was used instead of 3,7-diethyl-3,7-dimethylnonane-4,6-dione.

[0331] MS (m / z): 1386.01

[0332] <Preparation Example 16: Preparation of Compound 111>

[0333]

[0334] Compound 111 was obtained in the same manner as compound 102 in Preparation Example 13, except that (Z)-5-(cyclohexylamino)-2,6-dimethylheptane-3-one was used instead of 3,7-diethyl-3,7-dimethylnonane-4,6-dione.

[0335] MS (m / z): 1382.00

[0336] <Preparation Example 17: Preparation of Compound 113>

[0337]

[0338] Compound 113 was obtained in the same manner as compound 102 in Preparation Example 13, except that (Z)-6-(cyclohexylamino)-3,7-diethylnonane-4-one was used instead of 3,7-diethyl-3,7-dimethylnonane-4,6-dione.

[0339] MS (m / z): 1438.11

[0340] <Preparation Example 18: Preparation of Compound 121>

[0341]

[0342] Preparation of compound 121-1

[0343] Compound 18-4 (10.0 g, 31.8 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, (phenyl-d5)boric acid (10.8 g, 35.0 mmol, 1.1 eq), Pd(PPh3)4 (1.8 g, 1.59 mmol, 0.05 eq), and K2CO3 (13.1 g, 95.4 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Compound 121-1 (10.5 g, 92%) was thus obtained.

[0344] MS (m / z): 360.51

[0345] Preparation of compound 121-2

[0346] Compound 121-1 (10.5 g, 29.2 mmol, 1.8 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 h under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to give compound 121-2 (11.9 g, 89%).

[0347] MS (m / z): 1840.19

[0348] Preparation of compound 121

[0349] Compound 121-2 (11.9 g, 25.9 mmol, 1.0 eq) and 2,6-dimethylheptane-3,5-dione (8.8 g, 56.6 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Compound 121 (7.3 g, 52%) was thus obtained.

[0350] MS (m / z): 1088.45

[0351] <Preparation Example 19: Preparation of Compound 123>

[0352]

[0353] Compound 123 was obtained in the same manner as compound 121 in Preparation Example 18, except that 4,4,5,5-tetramethyl-2-(4-(prop-2-yl-2-d)naphth-2-yl)-1,3,2-dioxaborane was used instead of (phenyl-d5)boronic acid.

[0354] MS (m / z): 1268.71

[0355] <Preparation Example 20: Preparation of Compound 124>

[0356]

[0357] Compound 124 was obtained in the same manner as compound 121 in Preparation Example 18, except that 2-(4-(tert-butyl)naphth-2-yl-1,3,5,6,7,8-d6)-4,4,5,5-tetramethyl-1,3,2-dioxaborane was used instead of (phenyl-d5)boronic acid.

[0358] MS (m / z): 1304.82

[0359] <Preparation Example 21: Preparation of Compound 126>

[0360]

[0361] Compound 126 was obtained in the same manner as compound 111 in Preparation Example 16, except that 2-(4-(tert-butyl)naphth-2-yl-1,3,5,6,7,8-d6)-4,4,5,5-tetramethyl-1,3,2-dioxaborane was used instead of 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane.

[0362] MS (m / z): 1336.94

[0363] <Preparation Example 22: Preparation of Compound 130>

[0364]

[0365] Preparation of compound 130-1

[0366] 6-Bromo-7-methoxy-5-methyl-1,2,3,4-tetrahydronaphthalene (10 g, 39.3 mmol, 1.0 eq) was dissolved in 1,4-dioxane to prepare a solution. Then, bis(pinacol)diborane (14.9 g, 58.9 mmol, 1.5 eq), Pd(dppf)Cl2 (1.45 g, 1.96 mmol, 0.05 eq), and KOAc (11.5 g, 117 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane (MC). The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 130-1 (11.6 g, 98%) was obtained.

[0367] Preparation of compound 130-2

[0368] Compound 130-1 (11.6 g, 38.5 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 4-bromo-2-chloro-3-fluoropyridine (8.04 g, 38.5 mmol, 1.0 eq), Pd(PPh3)4 (2.22 g, 1.92 mmol, 0.05 eq), and K2CO3 (15.9 g, 115 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 130-2 (10.2 g, 87%) was obtained.

[0369] Preparation of compound 130-3

[0370] Compound 130-2 (10.2 g, 33.4 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and BBr3 was slowly added to it at 0°C, followed by stirring for 1 hour. After the reaction was complete, methanol was slowly added to it at 0°C, followed by extraction with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 130-3 (9.2 g, 95%) was obtained.

[0371] Preparation of compound 130-4

[0372] Compound 130-3 (9.2 g, 31.7 mmol, 1.0 eq) was dissolved in N-methyl-2-pyrrolidone (NMP) to prepare a solution. K₂CO₃ (13.1 g, 95.1 mmol, 3.0 eq) was then added, followed by stirring at 120 °C for 12 hours. After the reaction was complete, the solution was extracted with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO₄, and the solvent was removed by rotary evaporation. The solution was then purified by column chromatography using dichloromethane and hexane as eluents. The target compound 130-4 (6.0 g, 70%) was thus obtained.

[0373] Preparation of compound 130-5

[0374] Compound 130-4 (6.0 g, 22.1 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (2.9 g, 24.3 mmol, 1.1 eq), Pd(PPh3)4 (1.2 g, 1.10 mmol, 0.05 eq) and K2CO3 (9.1 g, 66.3 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 130-5 (6.4 g, 93%) was obtained.

[0375] Preparation of compound 130-6

[0376] Compound 130-5 (6.4 g, 20.5 mmol, 2.0 eq) and iridium(III) chloride hydrate (3.6 g, 10.2 mmol, 1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 130-6 (7.4 g, 85%) was obtained.

[0377] Preparation of compound 130

[0378] Compound 130-6 (7.4 g, 17.4 mmol, 1.0 eq) and pentane-2,4-dione (3.4 g, 34.8 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 130 (5.0 g, 63%) was obtained.

[0379] MS (m / z): 916.11

[0380] <Preparation Example 23: Preparation of Compound 134>

[0381]

[0382] Preparation of compound 134-6

[0383] Compound 134-5 (12.2 g, 33.2 mmol, 2.0 eq) and iridium(III) chloride hydrate (5.8 g, 16.6 mmol, 1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 134-6 (15 g, 95%) was obtained.

[0384] Preparation of compound 134

[0385] Compound 134-6 (15 g, 31.5 mmol, 1.0 eq) and pentane-2,4-dione (6.3 g, 63.0 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 134 (8.2 g, 52%) was obtained.

[0386] MS (m / z): 1013.39

[0387] <Preparation Example 24: Preparation of Compound 136>

[0388]

[0389] The target compound 136 was obtained in the same manner as the preparation of compound 134 in Preparation Example 23 above.

[0390] MS (m / z): 1054.43

[0391] <Preparation Example 25: Preparation of Compound 152>

[0392]

[0393] Preparation of compound 152-1

[0394] 5-Bromo-6-methoxy-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (10 g, 32.2 mmol, 1.0 eq) was dissolved in 1,4-dioxane to prepare a solution. Then, bis(pinacol)diborane (1.5 eq), Pd(dppf)Cl2 (0.05 eq), and KOAc (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. The organic layer was then purified by column chromatography using dichloromethane and hexane as the developing solvent. The target compound 152-1 (9.6 g, 84%) was thus obtained.

[0395] Preparation of compound 152-2

[0396] Compound 152-1 (9.6 g, 27.0 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 4-bromo-2-chloro-3-fluoropyridine (1.0 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 152-2 (8.2 g, 84%) was obtained.

[0397] Preparation of compound 152-3

[0398] Compound 152-2 (8.2 g, 22.6 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and BBr3 was slowly added to it at 0°C, followed by stirring for 1 hour. After the reaction was complete, methanol was slowly added to it at 0°C, followed by extraction with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 152-3 (7.4 g, 95%) was obtained.

[0399] Preparation of compound 152-4

[0400] Compound 152-3 (7.4 g, 21.4 mmol, 1.0 eq) was dissolved in NMP to prepare a solution, and then K2CO3 (3.0 eq) was added to it, followed by stirring at 120 °C for 12 h. After the reaction was complete, it was extracted with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. Purification was then performed using column chromatography with dichloromethane and hexane as the developing solvent. Thus, the target compound 152-4 (5.0 g, 72%) was obtained.

[0401] Preparation of compound 152-5

[0402] Compound 152-4 (5.0 g, 15.4 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (2.9 g, 1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 152-5 (5.2 g, 92%) was obtained.

[0403] Preparation of compound 152-6

[0404] Compound 152-5 (5.2 g, 14.1 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 152-6 (6.2 g, 92%) was obtained.

[0405] Preparation of compound 152

[0406] Compound 152-6 (6.2 g, 12.9 mmol, 1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 152 (4.5 g, 61%) was obtained.

[0407] MS (m / z): 1140.54

[0408] <Preparation Example 26: Preparation of Compound 153>

[0409]

[0410] Compound 153-6 (1.0 eq) and 3,7-diethyl-3,7-dimethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110°C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. The target compound 153 (63%) was thus obtained.

[0411] MS (m / z): 1168.57

[0412] <Preparation Example 27: Preparation of Compound 163>

[0413]

[0414] Preparation of compound 163-1

[0415] A solution was prepared by dissolving 6-bromo-5-methoxy-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (10 g, 32.2 mmol, 1.0 eq) in 1,4-dioxane. Then, bis(pinacol)diborane (1.5 eq), Pd(dppf)Cl2 (0.05 eq), and KOAc (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and MC. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as eluents. The target compound 163-1 (9.4 g, 82%) was thus obtained.

[0416] Preparation of compound 163-2

[0417] Compound 163-1 (9.4 g, 26.4 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 4-bromo-2-chloro-3-fluoropyridine (1.0 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 163-2 (8.1 g, 85%) was obtained.

[0418] Preparation of compound 163-3

[0419] Compound 163-2 (8.1 g, 22.4 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and BBr3 was slowly added to it at 0°C, followed by stirring for 1 hour. After the reaction was complete, methanol was slowly added to it at 0°C, followed by extraction with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 163-3 (7.4 g, 95%) was obtained.

[0420] Preparation of compound 163-4

[0421] Compound 163-3 (7.4 g, 21.2 mmol, 1.0 eq) was dissolved in NMP to prepare a solution, and then K2CO3 (3.0 eq) was added to it, followed by stirring at 120 °C for 12 h. After the reaction was complete, it was extracted with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. Purification was then performed by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 163-4 (5.0 g, 73%) was obtained.

[0422] Preparation of compound 163-5

[0423] Compound 163-4 (5.0 g, 15.4 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 163-5 (5.2 g, 91%) was obtained.

[0424] Preparation of compound 163-6

[0425] Compound 163-5 (5.2 g, 14.1 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 163-6 (6.4 g, 94%) was obtained.

[0426] Preparation of compound 163

[0427] Compound 163-6 (6.4 g, 13.2 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 163 (3.9 g, 58%) was obtained.

[0428] MS (m / z): 1028.41

[0429] <Preparation Example 28: Preparation of Compound 177>

[0430]

[0431] Preparation of compound 177-5

[0432] Compound 177-4 (5.0 g, 15.4 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Naphthaleneboronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were then added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 177-5 (5.8 g, 91%) was obtained.

[0433] Preparation of compound 177-6

[0434] Compound 177-5 (5.8 g, 14.0 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 177-6 (6.7 g, 94%) was obtained.

[0435] Preparation of compound 177

[0436] Compound 177-6 (6.7 g, 13.2 mmol, 1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 177 (4.2 g, 53%) was obtained.

[0437] MS (m / z): 1201.54

[0438] <Preparation Example 29: Preparation of Compound 180>

[0439]

[0440] Therefore, target compound 180 was obtained in the same manner as compound 177 in preparation example 28, except that (4-(tert-butyl)naphth-2-yl)boronic acid was used instead of naphthaleneboronic acid in preparation example 28.

[0441] MS (m / z): 1298.65

[0442] <Preparation Example 30: Preparation of Compound 183>

[0443]

[0444] Preparation of compound 183-1

[0445] 6-Bromo-5-methoxy-1,1,4,4-tetramethyl-8-neopentyl-1,2,3,4-tetrahydronaphthalene (10 g, 27.3 mmol, 1.0 eq) was dissolved in 1,4-dioxane to prepare a solution. Then, bis(pinacol)diborane (1.5 eq), Pd(dppf)Cl2 (0.05 eq), and KOAc (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and MC. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, the target compound 183-1 (9.2 g, 82%) was obtained.

[0446] Preparation of compound 183-2

[0447] Compound 183-1 (9.2 g, 22.3 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 4-bromo-2-chloro-3-fluoropyridine (1.0 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 12 h. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 183-2 (8.1 g, 87%) was obtained.

[0448] Preparation of compound 183-3

[0449] Compound 183-2 (8.1 g, 19.4 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and BBr3 was slowly added to it at 0°C, followed by stirring for 1 hour. After the reaction was complete, methanol was slowly added to it at 0°C, followed by extraction with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 183-3 (7.4 g, 95%) was obtained.

[0450] Preparation of compound 183-4

[0451] Compound 183-3 (7.4 g, 18.4 mmol, 1.0 eq) was dissolved in NMP to prepare a solution, and then K2CO3 (3.0 eq) was added to it, followed by stirring at 120 °C for 12 h. After the reaction was complete, it was extracted with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. Purification was then performed using column chromatography with dichloromethane and hexane as the developing solvent. Thus, the target compound 183-4 (5.0 g, 72%) was obtained.

[0452] Preparation of compound 183-5

[0453] Compound 183-4 (5.0 g, 13.2 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 183-5 (6.3 g, 91%) was obtained.

[0454] Preparation of compound 183-6

[0455] Compound 183-5 (6.3 g, 12.0 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 183-6 (6.6 g, 94%) was obtained.

[0456] Preparation of compound 183

[0457] Compound 183-6 (6.6 g, 11.2 mmol, 1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 183 (4.4 g, 58%) was obtained.

[0458] MS (m / z): 1353.70

[0459] <Preparation Example 31: Preparation of Compound 187>

[0460]

[0461] The target compound 187 was obtained in the same manner as the preparation of compound 183 in Preparation Example 30 above, except that 6-bromo-8-(2,2-dimethylpropyl-1,1-d2)-5-methoxy-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene was used instead of 6-bromo-5-methoxy-1,1,4,4-tetramethyl-8-neopentyl-1,2,3,4-tetrahydronaphthalene in Preparation Example 30.

[0462] MS (m / z): 1381.73

[0463] <Preparation Example 32: Preparation of Compound 197>

[0464]

[0465] Preparation of compound 197-1

[0466] A solution was prepared by dissolving 6-bromo-7-methoxy-1,1,4,4,5-pentamethyl-1,2,3,4-tetrahydronaphthalene (10 g, 32.2 mmol, 1.0 eq) in 1,4-dioxane. Then, bis(pinacol)diborane (1.5 eq), Pd(dppf)Cl2 (0.05 eq), and KOAc (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and MC. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as eluents. The target compound 197-1 (9.5 g, 83%) was thus obtained.

[0467] Preparation of compound 197-2

[0468] Compound 197-1 (9.5 g, 26.7 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 4-bromo-2-chloro-3-fluoropyridine (1.0 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 12 h. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 197-2 (8.1 g, 84%) was obtained.

[0469] Preparation of compound 197-3

[0470] Compound 197-2 (8.1 g, 22.4 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and BBr3 was slowly added to it at 0°C, followed by stirring for 1 hour. After the reaction was complete, methanol was slowly added to it at 0°C, followed by extraction with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 197-3 (7.4 g, 95%) was obtained.

[0471] Preparation of compound 197-4

[0472] Compound 197-3 (7.4 g, 21.2 mmol, 1.0 eq) was dissolved in NMP to prepare a solution, and then K2CO3 (3.0 eq) was added to it, followed by stirring at 120 °C for 12 h. After the reaction was complete, it was extracted with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. Purification was then performed using column chromatography with dichloromethane and hexane as the developing solvent. Thus, the target compound 197-4 (5.0 g, 73%) was obtained.

[0473] Preparation of compound 197-5

[0474] Compound 197-4 (5.0 g, 15.4 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 197-5 (6.7 g, 92%) was obtained.

[0475] Preparation of compound 197-6

[0476] Compound 197-5 (6.7 g, 14.1 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 197-6 (6.9 g, 92%) was obtained.

[0477] Preparation of compound 197

[0478] Compound 197-6 (6.9 g, 12.9 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 197 (4.5 g, 58%) was obtained.

[0479] MS (m / z): 1223.53

[0480] <Preparation Example 33: Preparation of Compound 202>

[0481]

[0482] Preparation of compound 202-1

[0483] 4-Methyl-5,6,7,8-tetrahydronaphthalene-2-thiol (10 g, 56.1 mmol, 1.0 eq) was dissolved in DMSO to prepare a solution, to which 2-chloro-3-iodopyridin-4-amine (2 eq), CuI (1 eq), Fe(acac)3 (1 eq), and K3PO4 (2 eq) were added, and the mixture was stirred at 140 °C for 3 h. After the reaction was complete, the mixture was extracted with distilled water and MC. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 202-1 (6.8 g, 40%) was obtained.

[0484] Preparation of compound 202-2

[0485] Compound 202-1 (6.8 g, 22.4 mmol, 1 eq) was dissolved in acetic acid to prepare a solution, and then tert-butyl nitrite (1.0 eq) was slowly added to it, followed by stirring at room temperature for 2 hours. After the reaction was complete, extraction was performed using distilled water and MC. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 202-2 (2.7 g, 42%) was obtained.

[0486] Preparation of compound 202-3

[0487] Compound 202-2 (2.7 g, 9.4 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 202-3 (3.3 g, 93%) was obtained.

[0488] Preparation of compound 202-4

[0489] Compound 202-3 (3.3 g, 8.74 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 202-4 (3.5 g, 85%) was obtained.

[0490] Preparation of compound 202

[0491] Compound 202-4 (3.5 g, 7.42 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 202 (2.3 g, 63%) was obtained.

[0492] MS (m / z): 934.22

[0493] <Preparation Example 34: Preparation of Compound 208>

[0494]

[0495] Preparation of compound 208-1

[0496] 4-Isobutyl-5,6,7,8-tetrahydronaphthalene-2-thiol (10 g, 45.4 mmol, 1.0 eq) was dissolved in DMSO to prepare a solution, to which 2-chloro-3-iodopyridin-4-amine (2 eq), CuI (1 eq), Fe(acac)3 (1 eq), and K3PO4 (2 eq) were added, and the mixture was stirred at 140 °C for 3 h. After the reaction was complete, the mixture was extracted with distilled water and MC. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 208-1 (6.4 g, 41%) was obtained.

[0497] Preparation of compound 208-2

[0498] Compound 208-1 (6.4 g, 18.6 mmol, 1 eq) was dissolved in acetic acid to prepare a solution, and then tert-butyl nitrite (1.0 eq) was slowly added to it, followed by stirring at room temperature for 2 hours. After the reaction was complete, extraction was performed using distilled water and MC. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 208-2 (2.5 g, 42%) was obtained.

[0499] Preparation of compound 208-3

[0500] Compound 208-2 (2.5 g, 7.81 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, (3-(tert-butyl)phenyl)boronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 208-3 (3.5 g, 94%) was obtained.

[0501] Preparation of compound 208-4

[0502] Compound 208-3 (3.5 g, 7.34 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 208-4 (3.3 g, 82%) was obtained.

[0503] Preparation of compound 208

[0504] Compound 208-4 (3.3 g, 6.01 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 208 (2.1 g, 62%) was obtained.

[0505] MS (m / z): 1167.45

[0506] <Preparation Example 35: Preparation of Compound 219>

[0507]

[0508] The target compound 219 was obtained in the same manner as the preparation of compound 202 in Preparation Example 33 above, except that 1,4,5,5,8-8-hexamethyl-5,6,7-8-tetrahydronaphthalene-2-thiol was used instead of 4-methyl-5,6,7,8-tetrahydronaphthalene-2-thiol in Preparation Example 33.

[0509] MS (m / z): 1044.33

[0510] <Preparation Example 36: Preparation of Compound 225>

[0511]

[0512] Preparation of compound 225-1

[0513] 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-thiol (10 g, 42.7 mmol, 1.0 eq) was dissolved in DMSO to prepare a solution, to which 2-chloro-3-iodopyridin-4-amine (2 eq), CuI (1 eq), Fe(acac)3 (1 eq), and K3PO4 (2 eq) were added, and the mixture was stirred at 140 °C for 3 h. After the reaction was complete, the mixture was extracted with distilled water and MC. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 225-1 (6.4 g, 42%) was obtained.

[0514] Preparation of compound 225-2

[0515] Compound 225-1 (6.4 g, 18.0 mmol, 1 eq) was dissolved in acetic acid to prepare a solution, and then tert-butyl nitrite (1.0 eq) was slowly added to it, followed by stirring at room temperature for 2 hours. After the reaction was complete, the mixture was extracted with distilled water and MC. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 225-2 (5.7 g, 93%) was obtained.

[0516] Preparation of compound 225-3

[0517] Compound 225-2 (5.7 g, 16.7 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 225-3 (6.0 g, 93%) was obtained.

[0518] Preparation of compound 225-4

[0519] Compound 225-3 (6.0 g, 15.5 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 225-4 (6.0 g, 83%) was obtained.

[0520] Preparation of compound 225

[0521] Compound 225-4 (6.0 g, 12.8 mmol, 1.0 eq) and 3,7-diethyl-3,7-dimethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 225 (3.9 g, 62%) was obtained.

[0522] MS (m / z): 1142.44

[0523] <Preparation Example 37: Preparation of Compound 234>

[0524]

[0525] Preparation of compound 234-1

[0526] 4,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-1-thiol (10 g, 42.7 mmol, 1.0 eq) was dissolved in DMSO to prepare a solution, to which 2-chloro-3-iodopyridin-4-amine (2 eq), CuI (1 eq), Fe(acac)3 (1 eq), and K3PO4 (2 eq) were added, and the mixture was stirred at 140 °C for 3 h. After the reaction was complete, the mixture was extracted with distilled water and MC. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 234-1 (6.6 g, 43%) was obtained.

[0527] Preparation of compound 234-2

[0528] Compound 234-1 (6.6 g, 18.3 mmol, 1 eq) was dissolved in acetic acid to prepare a solution, and then tert-butyl nitrite (1.0 eq) was slowly added to it, followed by stirring at room temperature for 2 hours. After the reaction was complete, extraction was performed using distilled water and MC. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 234-2 (5.7 g, 92%) was obtained.

[0529] Preparation of compound 234-3

[0530] Compound 234-2 (5.7 g, 16.8 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 234-3 (6.0 g, 93%) was obtained.

[0531] Preparation of compound 234-4

[0532] Compound 234-3 (6.0 g, 15.5 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 234-4 (6.5 g, 85%) was obtained.

[0533] Preparation of compound 234

[0534] Compound 234-4 (6.5 g, 13.1 mmol, 1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110 °C for 24 h under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 234 (4.3 g, 64%) was obtained.

[0535] MS (m / z): 1144.46

[0536] <Preparation Example 38: Preparation of Compound 236>

[0537]

[0538] The target compound 236 was obtained in the same manner as the preparation of compound 234 in Preparation Example 37 above, except that 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-1-thiol was used instead of 4,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-1-thiol in Preparation Example 37.

[0539] MS (m / z): 1159.48

[0540] <Preparation Example 39: Preparation of Compound 245>

[0541]

[0542] The target compound 245 was obtained in the same manner as the preparation of compound 234 in Preparation Example 37 above, except that 3,5,5,8,8-pentamethyl-4-neopentyl-5,6,7,8-tetrahydronaphthalene-1-thiol was used instead of 4,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-1-thiol in Preparation Example 37.

[0543] MS (m / z): 1228.55

[0544] <Preparation Example 40: Preparation of Compound 251>

[0545]

[0546] Preparation of compound 251-1

[0547] Compound 234-2 (10 g, 29.1 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 251-1 (13.1 g, 92%) was obtained.

[0548] Preparation of compound 251-2

[0549] Compound 251-1 (15.2 g, 13.1 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 251-2 (85%) was obtained.

[0550] Preparation of compound 251

[0551] Compound 251-2 (1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110°C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. The target compound 251 (64%) was thus obtained.

[0552] MS (m / z): 1275.54

[0553] <Preparation Example 41: Preparation of Compound 252>

[0554]

[0555] Preparation of compound 252-1

[0556] Compound 236-2 (10 g, 29.1 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 252-1 (13.1 g, 92%) was obtained.

[0557] Preparation of compound 252-2

[0558] Compound 252-1 (15.2 g, 13.1 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 252-2 was obtained.

[0559] Preparation of compound 252

[0560] Compound 252-2 (1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110°C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 252 was obtained.

[0561] MS (m / z): 1290.57

[0562] <Preparation Example 42: Preparation of Compound 255>

[0563]

[0564] Preparation of compound 255-2

[0565] Compound 255-1 (1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 255-2 (13.1 g, 92%) was obtained.

[0566] Preparation of compound 255-3

[0567] Compound 255-2 (2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110°C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 255-3 was obtained.

[0568] Preparation of compound 255

[0569] Compound 255-3 (1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110°C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 255 was obtained.

[0570] MS (m / z): 1331.61

[0571] <Preparation Example 43: Preparation of Compound 258>

[0572]

[0573] Preparation of compound 258-2

[0574] Compound 258-1 (1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 258-2 (13.1 g, 92%) was obtained.

[0575] Preparation of compound 258-3

[0576] Compound 258-2 (2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110°C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 258-3 was obtained.

[0577] Preparation of compound 258

[0578] Compound 258-3 (1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110°C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, column chromatography-based purification was performed using dichloromethane and hexane as developing solvents. Thus, the target compound 258 was obtained.

[0579] MS (m / z): 1290.57

[0580] <Preparation Example 44: Preparation of Compound 260>

[0581]

[0582] Preparation of compound 260-1

[0583] Compound 258-1 (1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl-1,3,5,6,7,8-d6)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 260-1 was obtained.

[0584] Preparation of compound 260-2

[0585] Compound 260-1 (2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110°C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 260-2 was obtained.

[0586] Preparation of compound 260

[0587] Compound 260-2 (1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110°C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, it was purified by column chromatography using dichloromethane and hexane as developing solvents. Thus, the target compound 260 was obtained.

[0588] MS (m / z): 1394.71

[0589] <Preparation Example 45: Preparation of Compound 261>

[0590]

[0591] Preparation of compound 261-2

[0592] Compound 261-1 (1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphth-2-yl-1,3,5,6,7,8-d6)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added to the solution, and the mixture was stirred at 110°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvent. Thus, the target compound 261-2 was obtained.

[0593] Preparation of compound 261-3

[0594] Compound 261-2 (2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then stirred at 110°C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with methanol. The solid was dried under vacuum. Thus, the target compound 261-3 was obtained.

[0595] Preparation of compound 261

[0596] Compound 261-3 (1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol and stirred at 110°C for 24 hours under nitrogen reflux. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation. Then, column chromatography-based purification was performed using dichloromethane and hexane as developing solvents. Thus, the target compound 261 was obtained.

[0597] MS (m / z): 1400.75

[0598] <Preparation Example 46: Preparation of Compound 274>

[0599]

[0600] The target compound 274 was obtained in the same manner as the preparation of compound 255 in Preparation Example 42 above, except that compound 274-1 was used instead of compound 255-1 in Preparation Example 42.

[0601] MS (m / z): 1242.46

[0602] <Preparation Example 47: Preparation of Compound 276>

[0603]

[0604] The target compound 276 was obtained in the same manner as the preparation of compound 255 in Preparation Example 42 above, except that compound 276-1 was used instead of compound 255-1 in Preparation Example 42.

[0605] MS (m / z): 1266.5

[0606] <Preparation Example 48: Preparation of Compound 279>

[0607]

[0608] The target compound 279 was obtained in the same manner as the preparation of compound 255 in Preparation Example 42 above, except that compound 279-1 was used instead of compound 255-1 in Preparation Example 42.

[0609] MS (m / z): 1312.53

[0610] <Preparation Example 49: Preparation of Compound 281>

[0611]

[0612] The target compound 281 was obtained in the same manner as the preparation of compound 255 in Preparation Example 42 above, except that compound 281-1 was used instead of compound 255-1 in Preparation Example 42.

[0613] MS (m / z): 1495.61

[0614] <Preparation Example 50: Preparation of Compound 282>

[0615]

[0616] The target compound 282 was obtained in the same manner as the preparation of compound 255 in Preparation Example 42 above, except that compound 282-1 was used instead of compound 255-1 in Preparation Example 42.

[0617] MS (m / z): 912.38

[0618] <Preparation Example 51: Preparation of Compound 285>

[0619]

[0620] The target compound 285 was obtained in the same manner as the preparation of compound 255 in Preparation Example 42 above, except that compound 285-1 was used instead of compound 255-1 in Preparation Example 42.

[0621] MS (m / z): 968.44

[0622] Example

[0623] <Current Example 1>

[0624] It is coated with a thickness of The glass substrate containing the ITO (indium tin oxide) thin film is cleaned, followed by ultrasonic cleaning with a solvent such as isopropanol, acetone, or methanol. The glass substrate is then dried. This forms the ITO transparent electrode.

[0625] HI-1, serving as a hole injection material, was deposited on an ITO transparent electrode using thermal vacuum deposition. This formed a hole injection layer with a thickness of 60 nm. Then, NPB, serving as a hole transport material, was deposited on the hole injection layer using thermal vacuum deposition. This formed a hole transport layer with a thickness of 80 nm. Next, CBP, serving as a matrix material for the light-emitting layer, was deposited on the hole transport layer using thermal vacuum deposition. Compound 1, serving as a dopant, was doped into the matrix material at a doping concentration of 5 wt%. This formed a light-emitting layer with a thickness of 30 nm. ET-1:Liq (1:1, weight ratio) (30 nm), serving as both an electron transport layer and an electron injection layer, was deposited on the light-emitting layer. Then, a 100 nm thick layer of aluminum was deposited on top to form the negative electrode. An organic light-emitting diode was thus fabricated. The materials used in the present embodiment 1 are as follows.

[0626]

[0627]

[0628] HI-1 is NPNPB, and ET-1 is ZADN.

[0629] <Comparative Example 1>

[0630] An organic light-emitting diode is manufactured in the same manner as in the present embodiment 1, except that RD having the following structure is used instead of compound 1 in the present embodiment 1.

[0631]

[0632] <Current Embodiment 2 to Current Embodiment 53>

[0633] The organic light-emitting diodes of each of the present embodiments 2 to 53 are manufactured in the same manner as in the present embodiment 1, except that the dopant compounds shown in Table 1 below are used instead of compound 1 in the present embodiment 1.

[0634] Test case

[0635] The organic light-emitting diodes (OLEDs) prepared in the present embodiments 1 to 53 and the comparative examples were connected to an external power source, and the characteristics of the OLEDs were evaluated at room temperature using a constant current source and a photometer.

[0636] Specifically, at 10mA / cm 2Operating voltage (%; relative value), external quantum efficiency (EQE; %; relative value), lifetime characteristics (LT95; %; relative value), full width at half maximum (FWHM) (%; relative value), and aspect ratio (%; relative value) were measured at the current density, and the relative values ​​were calculated relative to those of Comparative Example 1. The results are shown in Table 1 below.

[0637] LT95 lifespan refers to the time it takes for a display element to lose 5% of its initial brightness. LT95 is the most difficult customer specification to meet. LT95 can be used to determine whether image burn-in has occurred on a monitor.

[0638] Full width at half maximum (FWHM) refers to the wavelength width corresponding to half the maximum value of the curve representing the wavelength. A narrow FWHM indicates high color purity, meaning that light-emitting diodes (LEDs) can efficiently achieve the desired color based on combinations of light beams and can obtain a high color gamut. The FWHM was evaluated by photoluminescence (PL) intensity measurement, and the measurement equipment was model / manufacturer FS-5 / Edinburgh Instruments.

[0639] Aspect ratio is calculated based on the following formula: {(length of the long axis of the molecule centered on the metal (N-metal-N direction)) / (length of the short axis perpendicular to the long axis of the molecule centered on the metal)}. The aspect ratio is measured based on the distances between atoms in the molecule calculated using the Gaussian molecular calculation program (Gaussian 16).

[0640] Table 1

[0641]

[0642]

[0643]

[0644] The results in Table 1 show that the organometallic compounds used in each of the present embodiments 1 to 53 satisfy the structure represented by Formula I of this disclosure. Compared to the organic light-emitting diodes in Comparative Example 1, which used dopants that did not satisfy the structure represented by Formula I of this disclosure, the organic light-emitting diodes in which the dopants of the light-emitting layer are made by each of the present embodiments 1 to 53 have lower operating voltages and higher aspect ratios, and have improved external quantum efficiency (EQE) and lifetime (LT95). Furthermore, the organic light-emitting diodes in which the dopants of the light-emitting layer are made by each of the present embodiments 1 to 53 have narrow full width at half maximum (FWHM), resulting in improved color purity. Although embodiments of this disclosure have been described in more detail with reference to the accompanying drawings, this disclosure is not necessarily limited to these embodiments and can be modified in various ways within the spirit of the present disclosure. Therefore, the embodiments disclosed in this disclosure are intended to describe, not limit, the technical concept of this disclosure, and the scope of the technical concept of this disclosure is not limited by these embodiments. Therefore, it should be understood that the embodiments described above are not limiting in all respects, but rather illustrative.

Claims

1. An organometallic compound, said organometallic compound being represented by one of the group consisting of the following chemical formulas I-1-(4) and I-1-(5): <Chemical formula I-1-(4)> , In the chemical formula I-1-(4), M represents iridium (Ir), R1 through R8 each independently represent one selected from the group consisting of: hydrogen, C1 to C20 straight-chain alkyl groups, and deuterated C1 to C20 straight-chain alkyl groups. R9 independently represents one selected from the group consisting of: hydrogen, deuterium, halogen, C1 to C20 straight-chain alkyl and deuterium-substituted C1 to C20 straight-chain alkyl. Y represents S, X1 to X4 each represent CR independently. 12 ; Two adjacent R values ​​of X3 and X4 12 They fuse together to form a six-membered aromatic ring structure, and optionally, the aromatic ring structure is replaced by deuterium. R 12 It indicates that it is selected from the group consisting of: hydrogen, C1 to C20 straight-chain alkyl, deuterated C1 to C20 straight-chain alkyl, C3 to C20 branched alkyl and deuterated C3 to C20 branched alkyl. Z8 and Z9 represent oxygen (O), and Z3 and Z7 do not exist. Z4 to Z6 each independently represent one selected from the group consisting of: hydrogen, deuterium, and C3 to C20 branched alkyl groups. m is an integer of 2, n is an integer of 1, and p is 2. <Chemical formula I-1-(5)> In the chemical formula I-1-(5), M represents iridium (Ir), R1 through R8 each independently represent one selected from the group consisting of: hydrogen, C1 to C20 straight-chain alkyl groups, and deuterated C1 to C20 straight-chain alkyl groups. R9 independently represents one selected from the group consisting of: hydrogen, deuterium, halogen, C1 to C20 straight-chain alkyl and deuterium-substituted C1 to C20 straight-chain alkyl. Y represents S, X1 to X4 each represent CR independently. 12 ; Two adjacent R values ​​of X3 and X4 12 They fuse together to form a six-membered aromatic ring structure, and optionally, the aromatic ring structure is replaced by deuterium. R 12 It indicates that it is selected from the group consisting of: hydrogen, deuterium, C1 to C20 straight-chain alkyl, deuterium-substituted C1 to C20 straight-chain alkyl, C3 to C20 branched alkyl and deuterium-substituted C3 to C20 branched alkyl. Z8 and Z9 represent oxygen (O), and Z3 and Z7 do not exist. Z4 to Z6 each independently represent one selected from the group consisting of: hydrogen, deuterium, and C3 to C20 branched alkyl groups. m is an integer of 2, n is an integer of 1, and p is 2.

2. The organometallic compound of claim 1, wherein at least one of R9 is not hydrogen.

3. An organometallic compound, wherein the organometallic compound is selected from the group consisting of: 。 4. The organometallic compound of claim 1, wherein the organometallic compound is used as a red phosphorescent material.

5. An organic light-emitting diode, comprising: First electrode; The second electrode facing the first electrode; and An organic layer disposed between the first electrode and the second electrode; The organic layer mentioned above includes a light-emitting layer. The light-emitting layer contains a doped material. The doped material includes an organometallic compound according to any one of claims 1 to 4.

6. The organic light-emitting diode of claim 5, wherein the light-emitting layer is a red phosphorescent light-emitting layer.

7. The organic light-emitting diode of claim 5, wherein the organic layer further comprises at least one selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.

8. An organic light-emitting diode, comprising: The first and second electrodes facing each other; and The first light-emitting stack and the second light-emitting stack are located between the first electrode and the second electrode. Each of the first light-emitting stack and the second light-emitting stack includes at least one light-emitting layer. At least one of the light-emitting layers is a red phosphorescent light-emitting layer. The red phosphorescent emitting layer contains doped material. The doped material includes an organometallic compound according to any one of claims 1 to 4.

9. An organic light-emitting diode, comprising: The first and second electrodes facing each other; and The first light-emitting stack, the second light-emitting stack, and the third light-emitting stack are located between the first electrode and the second electrode. Each of the first light-emitting stack, the second light-emitting stack, and the third light-emitting stack includes at least one light-emitting layer. At least one of the light-emitting layers is a red phosphorescent light-emitting layer. The red phosphorescent emitting layer contains doped material. The doped material includes an organometallic compound according to any one of claims 1 to 4.

10. An organic light-emitting display device, comprising: substrate; Drive elements located on the substrate; and An organic light-emitting diode (OLED) disposed on the substrate and connected to the driving element, wherein the OLED comprises an OLED according to any one of claims 5 to 9.

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