Organometallic Compound and Organic Light-Emitting Diode Comprising the Same

Abstract

An organometallic compound represented by the following Chemical Formula I, and an organic light-emitting diode including the organometallic compound are disclosed. The organometallic compound has excellent light-emitting characteristics and structural stability. Accordingly, when the organometallic compound is used in an organic light-emitting diode, the operating voltage of the organic light-emitting diode is reduced, and the efficiency and lifetime characteristics of the organic light-emitting diode are improved. [Chemical Formula I]

Description

Technical Field

[0001] The present disclosure relates to an organometallic compound, and more particularly, to an organometallic compound having phosphorescent properties and an organic light emitting diode including the organometallic compound. Background Art

[0002] As display devices are applied to various fields, the interest in display devices is increasing day by day. One of the display devices is an organic light emitting display device including an organic light emitting diode (OLED) that is rapidly developing.

[0003] In an organic light emitting diode, when charges are injected into a light emitting layer formed between a positive electrode and a negative electrode, electrons and holes are recombined with each other in the light emitting layer to form excitons, and thus the energy of the excitons is converted into light. Accordingly, the organic light emitting diode emits light. Compared with conventional display devices, the organic light emitting diode can operate at a low voltage, consume relatively less power, exhibit excellent colors, and can be used in various ways since it can be applied to a flexible substrate. In addition, the size of the organic light emitting diode can be freely adjusted.

[0004] Compared with a liquid crystal display (LCD), an organic light emitting diode (OLED) has superior viewing angles and contrast ratios, and is light and ultrathin because an OLED does not require a backlight. The organic light emitting diode includes a plurality of organic layers between a negative electrode (electron injection electrode; cathode) and a positive electrode (hole injection electrode; anode). The plurality of organic layers may include a hole injection layer, a hole transport layer, a hole transport assist layer, an electron blocking layer, a light emitting layer, and an electron transport layer, etc.

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

[0006] The organic materials used in an organic light emitting diode can be roughly classified into light emitting materials and charge transport materials. The light emitting materials are important factors that determine the light emitting efficiency of the organic light emitting diode. The light emitting materials must have high quantum efficiency, excellent electron and hole mobilities, and must be uniformly and stably present in the light emitting layer. Based on the color of light, the light emitting materials can be classified into light emitting materials that emit blue, red, and green light. The color generating materials may include a matrix and a dopant to increase color purity and light emitting efficiency through energy transfer.

[0007] When a fluorescent material is used, a singlet state of excitons generated in the light emitting layer, which is about 25%, is used for light emission, while most of the triplet states of excitons generated in the light emitting layer, which is 75%, are dissipated as heat. However, when a phosphorescent material is used, both singlet and triplet states are used for light emission.

[0008] Generally, organometallic compounds are used as phosphorescent materials used in organic light-emitting diodes. There is a continuous need to research and develop phosphorescent materials to solve the problems of low efficiency and lifespan. SUMMARY OF THE INVENTION

[0009] Accordingly, an object of the present disclosure is to provide an organometallic compound capable of reducing the operating voltage and improving the efficiency and lifespan, and an organic light-emitting diode including an organic light-emitting layer containing the organometallic compound.

[0010] The object of the present disclosure is not limited to the above-mentioned object. Other objects and advantages not mentioned in the present disclosure can be understood based on the following description and can be more clearly understood based on the embodiments of the present disclosure. In addition, it will be readily understood that the objects and advantages of the present disclosure can be achieved by using the means shown in the claims and their combinations.

[0011] To achieve the above object, the present disclosure provides an organometallic compound having a novel structure represented by the following Chemical Formula I, an organic light-emitting diode in which a light-emitting layer contains the organometallic compound as a dopant thereof, 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 may represent a central coordinating 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] Each of R1 to R8 may independently represent one selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, and substituted or unsubstituted C3 to C20 bicycloalkyl;

[0017] Y may represent one selected from the group consisting of BR9, CR9R 10 , C═O, CNR9, SiR9R 10 , NR9, PR9, AsR9, SbR9, P(O)R9, P(S)R9, P(Se)R9, As(O)R9, As(S)R9, As(Se)R9, Sb(O)R9, Sb(S)R9, Sb(Se)R9, O, S, Se, Te, SO, SO2, SeO, SeO2, TeO, and TeO2;

[0018] R9 and R 10 each independently represents one selected from the group consisting of: hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, substituted or unsubstituted C2-C20 alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, substituted or unsubstituted C1-C20 alkoxy group, amino group, silyl group, acyl group, carbonyl group, carboxyl group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group and phosphino group;

[0019] A can represent the ring structure of isoquinoline;

[0020] Each of X1 to X4 independently represents one selected from CR 11 and nitrogen (N);

[0021] Two adjacent substituents among the substituents (R 11 ) of X1 to X4 can be fused to each other to form a ring structure selected from a five-membered carbon ring, a five-membered heterocyclic ring, a six-membered carbon ring and a six-membered heterocyclic ring;

[0022] Each R 11 can independently represent one selected from the group consisting of: hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C1-C20 heteroalkenyl group, substituted or unsubstituted C2-C20 alkynyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, substituted or unsubstituted C1-C20 alkoxy group, amino group, silyl group, acyl group, carbonyl group, carboxyl group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group and phosphino group;

[0023] can represent a bidentate ligand;

[0024] m can be an integer of 1, 2 or 3, n can be an integer of 0, 1 or 2, and m + n can be the oxidation number of metal M.

[0025] The organometallic compound according to the present disclosure can be used as a dopant for a phosphorescent emitting layer of an organic light emitting diode, so that the operating voltage of the organic light emitting diode can be reduced, and the efficiency and lifetime characteristics of the organic light emitting diode can be improved.

[0026] The effects of the present disclosure are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art according to the following description. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 is a cross-sectional view schematically showing an organic light emitting diode in which the light emitting layer includes an organometallic compound according to an illustrative embodiment of the present disclosure.

[0028] Figure 2 is a cross-sectional view schematically showing an organic light emitting diode having a tandem structure with two light emitting stacks and including an organometallic compound represented by Chemical Formula I according to an illustrative embodiment of the present disclosure.

[0029] Figure 3 is a cross-sectional view schematically showing an organic light emitting diode having a tandem structure with three light emitting stacks and including an organometallic compound represented by Chemical Formula I according to an illustrative embodiment of the present disclosure.

[0030] Figure 4 is a cross-sectional view schematically showing an organic light emitting display device including an organic light emitting diode according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0031] The advantages and features of the present disclosure, and the methods for achieving these advantages and features, will become apparent by reference to the embodiments described in detail below in conjunction with the accompanying drawings. However, the present disclosure is not limited to the embodiments disclosed below, but can be implemented in various different forms. Therefore, these embodiments are described only to make the present disclosure complete and to fully inform those of ordinary skill in the art to which the present disclosure pertains of the scope of the present disclosure, and the present disclosure is defined only by the scope of the claims.

[0032] For simplicity and clarity of illustration, the elements in the drawings are not necessarily drawn to scale. The same reference numerals in different drawings denote the same or similar elements and thus perform similar functions. In addition, for the sake of simplicity of description, the description and details of well-known steps and elements are omitted. Furthermore, in the following detailed description of the present disclosure, numerous specific details are set forth in order to provide a thorough understanding of the present disclosure. However, it should be understood that the present disclosure may be practiced without these specific details. In other instances, well-known methods, procedures, components, and circuits have not been described in detail so as not to unnecessarily obscure aspects of the present 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. On the contrary, the present disclosure is intended to cover alternatives, modifications, and equivalents that may be included within the spirit and scope of the present disclosure as defined by the appended claims.

[0033] The shapes, sizes, ratios, angles, quantities, etc. disclosed in the drawings used to describe the embodiments of the present disclosure are illustrative, and the present disclosure is not limited thereto. The same reference numerals herein refer to the same elements.

[0034] The terms used herein are for the purpose of describing particular embodiments only and are not intended to limit the present disclosure. As used herein, the singular forms “a” and “an” are also intended to include the plural forms unless the context clearly dictates otherwise. It should also be understood that when used in this specification, the terms “comprises,” “comprising,” “includes,” 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 an expression such as “at least one” is used before a list of elements, it can modify the entire list of elements and can also modify individual elements of the list. In the interpretation of numerical values, errors or tolerances may occur even if not explicitly described.

[0035] In addition, it should also be understood that when a first element or layer is referred to as being “on” a second element or layer, the first element can be directly disposed on the second element or can be indirectly disposed on the second element with 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 “connected to” or “coupled to” another element or layer, it can be directly connected to or coupled to the other element or layer, or there can be one or more intermediate elements or layers. In addition, it should also be understood that when an element or layer is referred to as being “between” two elements or layers, it can be the only element or layer between the two elements or layers, or there may also be one or more intermediate elements or layers.

[0036] In addition, as used herein, when a layer, film, region, plate, etc. is disposed "on" or "on top of" another layer, film, region, plate, etc., the former may directly contact the latter, or another layer, film, region, plate, etc. may be disposed between the former and the latter. As used herein, when a layer, film, region, plate, etc. is directly disposed "on" or "on top of" another layer, film, region, plate, etc., the former directly contacts the latter and no other layer, film, region, plate, etc. is disposed between the former and the latter. In addition, as used herein, when a layer, film, region, plate, etc. is disposed "below" or "beneath" another layer, film, region, plate, etc., the former may directly contact the latter, or another layer, film, region, plate, etc. may be disposed between the former and the latter. As used herein, when a layer, film, region, plate, etc. is directly disposed "below" or "beneath" another layer, film, region, plate, etc., the former directly contacts the latter and no other layer, film, region, plate, etc. is disposed between the former and the latter.

[0037] In the description of temporal relationships, for example, the temporal precedence relationship between two events such as "after", "subsequently", "before", etc., unless specified as "immediately after", "immediately subsequently" or "immediately before", another event may occur between these two events.

[0038] When a particular embodiment can be implemented differently, a particular function or operation in a particular module can occur in an order different from the order specified in the flowchart. For example, two consecutive blocks can actually be executed substantially simultaneously, or these two blocks can be executed in the reverse order depending on the functions or operations involved.

[0039] 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 element, component, region, layer or part. Thus, without departing from the spirit and scope of the present disclosure, the first element, component, region, layer or part described below may be referred to as the second element, component, region, layer or part.

[0040] The features of the various embodiments of the present disclosure may be combined partially or wholly with each other, and may be technically related or interoperable with each other. Each embodiment may be implemented independently of each other, or may be implemented together in an associated relationship.

[0041] When interpreting a numerical value, the value is interpreted to include the error range, unless there is a separate and explicit description.

[0042] Unless otherwise defined, all terms used herein, including technical and scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this inventive concept pertains. It should also be understood that terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and will not be interpreted as idealized or overly formal meanings unless expressly defined in this document.

[0043] As used herein, terms such as "embodiment", "example", "aspect", etc. should not be construed as any aspect or design described as being better than or superior to other aspects or designs.

[0044] In addition, the term "or" means "inclusive or" rather than "exclusive or". That is, unless otherwise stated or clear from the context, the expression "x uses a or b" means any of the natural inclusive arrangements.

[0045] The terms used in the following description are selected as general terms in the relevant technical field. However, depending on the development and / or changes in technology, convention, the preference of those skilled in the art, etc., there may be other terms in addition to the terms. Therefore, the terms used in the following description should not be construed as limiting the technical idea, but should be understood as examples of terms used to describe embodiments.

[0046] In addition, in certain cases, the terms may be arbitrarily selected by the applicant, and in such cases, their detailed meanings will be described in the corresponding description part. Therefore, the terms used in the following description should not be simply understood based on the name of the terms, but should be understood based on the meaning of the terms and the content throughout the specific embodiments.

[0047] As used herein, the term "heterocycle" refers to a ring structure in which one or more carbon atoms, such as 1 to 5 carbon atoms, constituting an aromatic ring, an alicyclic ring, or an arylalkyl ring, are replaced by heteroatoms such as nitrogen (N), oxygen (O), and sulfur (S).

[0048] Hereinafter, the structure of an organometallic compound according to the present disclosure and an organic light-emitting diode including the organometallic compound will be described.

[0049] Conventionally, organometallic compounds have been used as dopants in the light-emitting layer of organic light-emitting diodes. For example, a structure such as 2-phenylpyridine is recognized as the main ligand structure of organometallic compounds. However, such conventional light-emitting dopants have limitations in improving the efficiency and lifetime of organic light-emitting diodes. Therefore, there is a need to develop a new type of light-emitting doping material. Accordingly, the inventors of the present disclosure have obtained a light-emitting doping material capable of further improving the efficiency and lifetime of organic light-emitting diodes, and thus completed the present disclosure.

[0050] Specifically, an organometallic compound according to an embodiment of the present disclosure can be represented by the following Chemical Formula I, wherein the main ligand of Chemical Formula I has a heterocyclic structure, and at least one of the two rings connected to the central coordination metal (M) contains nitrogen (N). For example, the main ligand can have a quinoline ring structure, an isoquinoline structure, and the like, preferably an isoquinoline structure. In addition, an aromatic ring and an alicyclic ring can be fused into the nitrogen (N)-containing heterocyclic ring to enhance the rigidity of the compound molecule and obtain a stable structure.

[0051] The inventors of the present disclosure have determined through experiments that when the doping material of the phosphorescent emitting layer of an organic light-emitting diode includes the organometallic compound represented by Chemical Formula I, the luminous efficiency and lifespan of the organic light-emitting diode are improved and its operating voltage is reduced, thereby completing the present disclosure.

[0052] The organometallic compound having the above characteristics according to the present disclosure can be represented by the following Chemical Formula I.

[0053] [Chemical Formula I]

[0054]

[0055] In the above Chemical Formula I,

[0056] M can represent a central coordination 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);

[0057] Each of R1 to R8 can independently represent one selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, and a substituted or unsubstituted C3 to C20 bicycloalkyl group, wherein at least one of R1 to R8 can be a methyl group;

[0058] Y can represent one selected from the group consisting of BR9, CR9R 10 , C=O, CNR9, SiR9R 10 , NR9, PR9, AsR9, SbR9, P(O)R9, P(S)R9, P(Se)R9, As(O)R9, As(S)R9, As(Se)R9, Sb(O)R9, Sb(S)R9, Sb(Se)R9, O, S, Se, Te, SO, SO2, SeO, SeO2, TeO, and TeO2;

[0059] R9 and R 10Each can independently represent one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 arylalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C20 alkoxy, amino, silyl, acyl, carbonyl, carboxyl, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl and phosphino;

[0060] A can represent the ring structure of isoquinoline;

[0061] Each of X1 to X4 can independently represent one selected from CR 11 and nitrogen (N);

[0062] Two adjacent substituents among the substituents (R 11 ) of X1 to X4 can be fused to each other to form a ring structure selected from a five-membered carbon ring, a five-membered heterocyclic ring, a six-membered carbon ring and a six-membered heterocyclic ring;

[0063] Each R 11 can independently represent one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 arylalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C20 alkoxy, amino, silyl, acyl, carbonyl, carboxyl, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl and phosphino;

[0064] can represent a bidentate ligand;

[0065] m can be an integer of 1, 2 or 3, n can be an integer of 0, 1 or 2, and m + n can be the oxidation number of metal M.

[0066] Based on the connection position between two rings of the isoquinoline ring structure of the ring structure (A) as the main ligand connected to the central coordinating metal (M) in Chemical Formula I, the organometallic compound according to an embodiment of the present disclosure can be represented by one selected from the group consisting of the following Chemical Formula II-1 and Chemical Formula II-2. However, the present invention is not necessarily limited to the above structure. In addition, each of the following Chemical Formula II-1 and Chemical Formula II-2 specifies the structure of the auxiliary ligand of Chemical Formula I. However, the present disclosure is not necessarily limited thereto.

[0067] [Chemical Formula II-1]

[0068]

[0069] [Chemical Formula II-2]

[0070]

[0071] In Chemical Formula II-1 and Chemical Formula II-2,

[0072] each of Z3 to Z6 and Z9 may independently represent one selected from the group consisting of: hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 arylalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C20 alkoxy, amino, silyl, acyl, carbonyl, carboxyl, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphino;

[0073] two adjacent substituents among Z3 to Z6 and Z9 may form a C3-C20 carbocyclic ring or a C3-C20 heterocyclic ring;

[0074] each of Z7 and Z8 may be one selected from oxygen (O) and nitrogen (N).

[0075] In the organometallic compound according to an embodiment of the present disclosure, the auxiliary ligand bound to the central coordinating metal may be a bidentate ligand. The bidentate ligand may contain an electron donor. The electron donor auxiliary ligand may increase the electron density of the central coordinating metal to reduce the energy of MLCT (metal-to-ligand charge transfer) and increase 3 MLCT to T 1The contribution percentage of the state. As a result, an organic light emitting diode including the organometallic compound of the present disclosure can achieve improved light emitting characteristics such as high luminous efficiency and high external quantum efficiency.

[0076] Phosphorescence can be effectively obtained at room temperature by using an iridium (Ir) or platinum (Pt) metal complex having a large atomic number. Thus, in the organometallic compound according to an embodiment of the present disclosure, the central coordinating metal (M) may preferably be iridium (Ir) or platinum (Pt), more preferably iridium (Ir). However, the present disclosure is not limited thereto.

[0077] Specific examples of the compound represented by Chemical Formula I of the present disclosure may include one selected from the group consisting of the following Compounds 1 to 183. However, the present disclosure is not limited thereto as long as the compound falls within the definition of Chemical Formula I.

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] According to an embodiment of the present disclosure, the organometallic compound represented by Chemical Formula I of the present disclosure can be used as a doping material for achieving red phosphorescence or green phosphorescence, preferably as a doping material for achieving red phosphorescence.

[0085] Refer to Figure 1, according to an embodiment of the present disclosure, an organic light emitting diode 100 may be provided, which includes 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, and the light emitting layer 160 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. In addition, in the organic light emitting diode 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.

[0086] In addition, although Figure 1 not shown in, a hole transport assisting layer may be further added between the hole transport layer 150 and the light emitting layer 160. The hole transport assisting layer may contain a compound having good hole transport performance and may reduce the HOMO energy level difference between the hole transport layer 150 and the light emitting layer 160, thereby adjusting the hole injection performance. Therefore, the accumulation of holes at the interface between the hole transport assisting layer and the light emitting layer 160 may be reduced, thereby reducing the quenching phenomenon in which excitons disappear at the interface due to polarons. Therefore, the deterioration of the device may be reduced, and the device may be stabilized, thereby improving its efficiency and lifetime.

[0087] The first electrode 110 may act as an anode and may be made of ITO, IZO, tin oxide, or zinc oxide, which is a conductive material having a relatively large work function value. However, the present disclosure is not limited thereto.

[0088] The second electrode 120 may act as a cathode and may include Al, Mg, Ca, or Ag, or an alloy or combination thereof, which is a conductive material having a relatively small work function value. However, the present disclosure is not limited thereto.

[0089] The hole injection layer 140 may be located between the first electrode 110 and the hole transport layer 150. The hole injection layer 140 may have a function of improving the interfacial characteristics between the first electrode 110 and the hole transport layer 150, and may be selected from materials having appropriate conductivity. The hole injection layer 140 may include a compound selected from the group consisting of: MTDATA, CuPc, TCTA, HATCN, TDAPB, PEDOT / PSS, and N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine). Preferably, the hole injection layer 140 may include N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine). However, the present disclosure is not limited thereto.

[0090] 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 a compound selected from the group consisting of: TPD, NPD, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-4-amine, and the like. Preferably, the hole transport layer 150 may include NPB. However, the present disclosure is not limited thereto.

[0091] According to the present disclosure, in order to improve the light-emitting efficiency of the diode 100, the light-emitting layer 160 may be formed by doping a host material 160' with an organometallic compound represented by Chemical Formula I as a dopant 160". The dopant 160" may be used as a green light-emitting material or a red light-emitting material, and is preferably used as a red phosphorescent material.

[0092] The doping concentration of the dopant 160" according to the present disclosure may be adjusted to be in the range of 1 to 30% by weight based on the total weight of the host material 160'. However, the present disclosure is not limited thereto. For example, the doping concentration may be in the range of 2 to 20% by weight, such as 3 to 15% by weight, such as 5 to 10% by weight, such as 3 to 8% by weight, such as 2 to 7% by weight, such as 5 to 7% by weight, or such as 5 to 6% by weight.

[0093] The light-emitting layer 160 according to the present disclosure includes a host material 160' known in the art and, at the same time, the light-emitting layer 160 includes an organometallic compound represented by Chemical Formula I as a dopant 160", and thus the effects of the present disclosure can be achieved. For example, according to the present disclosure, the host material 160' may include a compound containing a carbazolyl group, and may preferably include a host material selected from the group consisting of: CBP (carbazole biphenyl), mCP (1,3-bis(carbazol-9-yl)), etc. However, the present disclosure is not limited thereto.

[0094] In addition, the electron transport layer 170 and the electron injection layer 180 may 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 a high electron mobility so that electrons can be stably supplied to the light-emitting layer under smooth electron transport.

[0095] For example, the material of the electron transport layer 170 may be well-known in the art and may include one selected from the group consisting of: Alq3 (aluminum tris(8-hydroxyquinoline)), Liq (lithium 8-hydroxyquinoline), PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), TAZ (3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), spiro-PBD, BAlq (bis(2-methyl-8-hydroxyquinolinato)-4-(phenylphenolato)aluminum), SAlq, TPBi ((2,2’,2-(1,3,5-benzenetriyl)-tris(1-phenyl-1-H-benzimidazole)), (2,2',2-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)), oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, and 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl]-1-phenyl-1H-benzo[d]imidazole. Preferably, the material of the electron transport layer 170 may include 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl]-1-phenyl-1H-benzo[d]imidazole. However, the present disclosure is not limited thereto.

[0096] The electron injection layer 180 is used to facilitate electron injection. The material of the electron injection layer can be well-known in the art and can include compounds selected from the group consisting of: Alq3 (aluminum tris(8-hydroxyquinoline)), PBD, TAZ, spiro-PBD, BAlq, SAlq, etc. However, the present 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, the present disclosure is not limited thereto.

[0097] The organic light-emitting diode according to the present disclosure can be implemented as a white light-emitting diode having a tandem structure. The tandem organic light-emitting diode according to an illustrative embodiment of the present disclosure can be formed in such a structure that in this structure, adjacent light-emitting stacks among two or more light-emitting stacks are connected to each other via a charge generation layer (CGL). The organic light-emitting diode can include at least two light-emitting stacks provided on a substrate, wherein each of the at least two light-emitting stacks includes a first electrode and a second electrode facing each other, and a light-emitting layer provided between the first electrode and the second electrode to emit light in a specific wavelength band. The plurality of light-emitting stacks can emit light of the same color or different colors. In addition, one or more light-emitting layers can be included in one light-emitting stack, and the plurality of light-emitting layers can emit light of the same color or different colors.

[0098] In this case, the light-emitting layer included in at least one of the plurality of light-emitting stacks can contain an organometallic compound represented by Chemical Formula I according to the present disclosure as a dopant. Adjacent light-emitting stacks in the plurality of light-emitting stacks in the tandem structure can be connected to each other via a charge generation layer CGL including an N-type charge generation layer and a P-type charge generation layer.

[0099] According to some embodiments of the present disclosure, Figure 2 and Figure 3 are cross-sectional views schematically showing an organic light-emitting diode having a tandem structure with two light-emitting stacks and an organic light-emitting diode having a tandem structure with three light-emitting stacks, respectively.

[0100] As Figure 2As shown, the organic light-emitting diode 100 according to the present 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 including 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 including a second light-emitting layer 262, and a charge generation layer CGL located between the first light-emitting stack ST1 and the second light-emitting stack ST2. The charge generation layer CGL may include an N-type charge generation layer 291 and a P-type charge generation layer 292. At least one of the first light-emitting layer 261 and the second light-emitting layer 262 may include an organometallic compound represented by Chemical Formula I according to the present disclosure as a dopant. For example, as Figure 2 shown, the second light-emitting layer 262 of the second light-emitting stack ST2 may include a host material 262' and a dopant 262" made of an organometallic compound represented by Chemical Formula I doped into the host material 262'. Although in Figure 2 not shown, each of the first light-emitting stack ST1 and the second light-emitting stack ST2 may further include an additional light-emitting layer other than each of the first light-emitting layer 261 and the second light-emitting layer 262.

[0101] As Figure 3 shown, the organic light-emitting diode 100 according to the present 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 including a first light-emitting layer 261, a second light-emitting stack ST2 including a second light-emitting layer 262, a third light-emitting stack ST3 including a third light-emitting layer 263, a first charge generation layer CGL1 located between the first light-emitting stack ST1 and the second light-emitting stack ST2, and a second charge generation layer CGL2 located between the second light-emitting stack ST2 and the third light-emitting stack ST3. The first charge generation layer CGL1 may include an N-type charge generation layer 291 and a P-type charge generation layer 292. The second charge generation layer CGL2 may include an N-type charge generation layer 293 and a P-type charge generation 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 include an organometallic compound represented by Chemical Formula I according to the present disclosure as a dopant. For example, as Figure 3 shown, the second light-emitting layer 262 of the second light-emitting stack ST2 may include a host material 262' and a dopant 262" made of an organometallic compound represented by Chemical Formula I doped into the host material 262'. Although Figure 3Although not shown in the drawings, each of the first light-emitting stack ST1, the second light-emitting stack ST2, and the third light-emitting stack ST3 may further include additional light-emitting layers in addition to each of the first light-emitting layer 261, the second light-emitting layer 262, and the third light-emitting layer 263.

[0102] In addition, an organic light-emitting diode according to an embodiment of the present disclosure may include a tandem structure in which four or more light-emitting stacks and three or more charge generation layers are disposed between a first electrode and a second electrode.

[0103] The organic light-emitting diode according to the present disclosure may be used as a light-emitting element for each of an organic light-emitting display device and a lighting device. In one embodiment, Figure 4 FIG. is a cross-sectional view schematically showing an organic light-emitting display device including an organic light-emitting diode according to some embodiments of the present disclosure as a light-emitting element thereof.

[0104] As Figure 4 shown, the organic light-emitting display device 3000 includes a substrate 3010, an organic light-emitting diode 4000, and a package film 3900 covering the organic light-emitting diode 4000. A driving thin-film transistor Td 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.

[0105] Although not explicitly shown in Figure 4 , gate lines and data lines that cross each other to define a pixel region, a power supply line that extends parallel to and spaced apart from one of the gate lines and the data lines, a switching thin-film transistor connected to the gate lines and the data lines, and a storage capacitor connected to one electrode of the thin-film transistor and the power supply line are further formed on the substrate 3010.

[0106] 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.

[0107] The semiconductor layer 3100 may be formed on the substrate 3010 and may be made of an oxide semiconductor material or polysilicon. When the semiconductor layer 3100 is made of an oxide semiconductor material, a light-shielding pattern (not shown) may be formed under the semiconductor layer 3100. The light-shielding pattern prevents light from entering the semiconductor layer 3100 to prevent the semiconductor layer 3100 from deteriorating due to light. Alternatively, the semiconductor layer 3100 may be made of polysilicon. In this case, two edges of the semiconductor layer 3100 may be doped with impurities.

[0108] A gate insulating layer 3200 made of an insulating material is formed over the entire surface of a substrate 3010 and on a semiconductor layer 3100. The gate insulating layer 3200 can be made of an inorganic insulating material such as silicon oxide or silicon nitride.

[0109] 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.

[0110] An interlayer insulating layer 3400 made of an insulating material is formed over the entire surface of the substrate 3010 and on the gate 3300. The interlayer insulating layer 3400 can be made of an inorganic insulating material such as silicon oxide or silicon nitride or an organic insulating material such as benzocyclobutene or photo - acryl.

[0111] The interlayer insulating layer 3400 has a first semiconductor layer contact hole 3420 and a second semiconductor layer contact hole 3440 defined therein that 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 respectively located on two opposite sides of the gate 3300 and are spaced apart from the gate 3300.

[0112] A source 3520 and a drain 3540 made of a conductive material such as metal are formed on the interlayer insulating layer 3400. The source 3520 and the drain 3540 are located around the gate 3300 and are spaced apart from each other, and respectively contact two opposite sides of the semiconductor layer 3100 via the first semiconductor layer contact hole 3420 and the second semiconductor layer contact hole 3440. The source 3520 is connected to a power supply line (not shown).

[0113] The semiconductor layer 3100, the gate 3300, the source 3520, and the drain 3540 constitute a driving thin film transistor Td. The driving thin film transistor Td has a coplanar structure in which the gate 3300, the source 3520, and the drain 3540 are located on top of the semiconductor layer 3100.

[0114] Alternatively, the driving thin film transistor Td can have an inverted staggered structure in which the gate is disposed below the semiconductor layer and the source and the drain are disposed above the semiconductor layer. In this case, the semiconductor layer can be made of amorphous silicon. In one example, a switching thin film transistor (not shown) can have a structure substantially the same as that of the driving thin film transistor (Td).

[0115] 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 red color filter pattern, the green color filter pattern, and the blue color filter pattern that absorb light may be separately formed in different pixel regions. Each of these color filter patterns may be arranged 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. Employing the color filter 3600 may allow the organic light-emitting display device 3000 to achieve full-color display.

[0116] For example, when the organic light-emitting display device 3000 is a bottom-emission type, the color filter 3600 that absorbs light may be located on a 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 a top-emission type, the color filter may be located on top of the organic light-emitting diode 4000, i.e., on top of the second electrode 4200. For example, the color filter 3600 may be formed to have a thickness of 2 to 5 μm.

[0117] In one example, a passivation layer 3700 having a drain contact hole 3720 that defines an exposure of the drain 3540 of the driving thin-film transistor Td therein is formed to cover the driving thin-film transistor Td.

[0118] On the passivation layer 3700, each first electrode 4100 connected to the drain 3540 of the driving thin-film transistor Td via the drain contact hole 3720 is separately formed in each pixel region.

[0119] The first electrode 4100 may serve as a positive electrode (anode) and may be made of a conductive material having a relatively large work function value. For example, the first electrode 4100 may be made of a transparent conductive material such as ITO, IZO, or ZnO.

[0120] In one example, when the organic light-emitting display device 3000 is a top-emission type, a reflective electrode or a reflective layer may be further formed under the first electrode 4100. For example, the reflective electrode or the reflective layer may be made of one of aluminum (Al), silver (Ag), nickel (Ni), and aluminum-palladium-copper (APC) alloy.

[0121] A bank layer 3800 that covers the edge of the first electrode 4100 is formed on the passivation layer 3700. The bank layer 3800 exposes the center of the first electrode 4100 corresponding to the pixel region.

[0122] The organic layer 4300 is formed on the first electrode 4100. If necessary, the organic light-emitting diode 4000 may have a tandem structure. Regarding the tandem structure, reference may be made to Figures 2 to 4 and the description above it.

[0123] 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 having a relatively small work function value, and may be used as a negative electrode (cathode). For example, the second electrode 4200 may be made of one of aluminum (Al), magnesium (Mg), and an aluminum-magnesium alloy (Al-Mg).

[0124] The first electrode 4100, the organic layer 4300, and the second electrode 4200 constitute the organic light-emitting diode 4000.

[0125] The encapsulation film 3900 is formed on the second electrode 4200 to prevent external moisture from penetrating the organic light-emitting diode 4000. Although not explicitly shown in Figure 4 , the encapsulation film 3900 may have a three-layer structure in which a first inorganic layer, an organic layer, and an inorganic layer are sequentially stacked. However, the present disclosure is not limited thereto.

[0126] Hereinafter, preparation examples and current examples of the present disclosure will be described. However, the following current examples are only one example of the present disclosure. The present disclosure is not limited thereto.

[0127] Preparation Example

[0128] <Preparation Example 1: Preparation of Compound 1>

[0129]

[0130] Preparation of Compound 1-1

[0131] 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(pinacolato)diboron (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 h. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 1-1 (11.7 g, 98%) was obtained.

[0132] MS(m / z): 288.19

[0133] Preparation of Compound 1-2

[0134] 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, 7-bromo-6-fluoroisoquinoline (9.15 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 h. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 1-2 (10.9 g, 88%) was obtained.

[0135] MS(m / z): 307.14

[0136] Preparation of Compound 1-3

[0137] Compound 1-2 (10.9 g, 35.6 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution. Then, BBr3 was slowly added thereto at 0 °C, and the mixture was stirred for 1 h. After the reaction was completed, methanol was slowly added thereto at 0 °C, and then it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents to obtain compound 1-3 (9.9 g, 95%).

[0138] MS (m / z): 293.12

[0139] Preparation of Compounds 1-4

[0140] Dissolve Compound 1-3 (9.9 g, 33.8 mmol, 1.0 eq) in N-methyl-2-pyrrolidone to prepare a solution. Then, add K2CO3 (14.0 g, 101.4 mmol, 3.0 eq) thereto, and subsequently stir at 120 °C for 12 hours. After the reaction is completed, extract with distilled water and ethyl acetate at room temperature. Dry the organic layer with anhydrous MgSO4, then remove the solvent therefrom using a rotary evaporator. Subsequently, purify it by column chromatography using dichloromethane and hexane as the eluent to obtain Compound 1-4 (8.1 g, 88%).

[0141] MS (m / z): 273.12

[0142] Preparation of Compounds 1-5

[0143] Dissolve Compound 1-4 (8.1 g, 29.7 mmol, 1.0 eq) in dichloromethane to prepare a solution. Then, add m-CPBA to the solution and stir at room temperature for 24 hours. After the reaction is completed, perform layer separation with distilled water and dichloromethane, and then concentrate the organic layer. Dissolve the concentrated residue in POCl3 (40 ml) to prepare a solution and stir at 80 °C for 4 hours. After the reaction is completed, remove POCl3 therefrom using a rotary evaporator, then add saturated aqueous NaHCO3 solution thereto for neutralization. Perform layer separation with distilled water and dichloromethane, then dry the organic layer with anhydrous MgSO4, remove the solvent therefrom using a rotary evaporator. Subsequently, purify it by column chromatography using dichloromethane and hexane as the eluent to obtain Compound 1-5 (7.4 g, 81%).

[0144] MS (m / z): 307.08

[0145] Preparation of Compounds 1-6

[0146] Compound 1-5 (7.4 g, 24.0 mmol, 1.0 eq) was 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 completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed therefrom using a rotary evaporator. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the eluent to obtain Compound 1-6 (7.7 g, 93%).

[0147] MS (m / z): 349.15

[0148] Preparation of Compound 1-7

[0149] Compound 1-6 (7.7 g, 22.3 mmol, 2.0 eq) and iridium(III) chloride hydrate (3.3 g, 11.2 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 then the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to obtain Compound 1-7 (8.6 g, 98%).

[0150] MS (m / z): 1572.51

[0151] Preparation of Compound 1

[0152] Compound 1-7 (8.6 g, 21.8 mmol, 1.0 eq) and pentane-2,4-dione (6.5 g, 42.0 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol, and then stirred at 110 °C for 24 hours under nitrogen reflux. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 1 (9.0 g, 84%) was obtained.

[0153] MS (m / z): 988.29

[0154] <Preparation Example 2: Preparation of Compound 7>

[0155]

[0156] Preparation of Compound 7-1

[0157] Compounds 1 - 5 (10.0 g, 32.5 mmol, 1.0 eq) were dissolved in 1,4 - dioxane and distilled water to prepare a solution. Then, (3 - (tert - butyl)phenyl)boronic acid (6.3 g, 35.8 mmol, 1.1 eq), Pd(PPh3)4 (1.8 g, 1.62 mmol, 0.05 eq), and K2CO3 (13.4 g, 97.5 mmol, 3.0 eq) were added to the solution, and the mixture was stirred at 110 °C for 8 hours. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed from it using a rotary evaporator. Subsequently, it was purified by column chromatography using dichloromethane and hexane as eluents to obtain compound 7 - 1 (11.8 g, 90%).

[0158] MS (m / z): 405.21

[0159] Preparation of Compound 7 - 2

[0160] Compound 7 - 1 (11.8 g, 29.2 mmol, 2.0 eq) and iridium(III) chloride hydrate (4.3 g, 14.6 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 then the resulting solid was filtered and washed with methanol. The solid was dried under vacuum to obtain compound 7 - 2 (9.0 g, 98%).

[0161] MS (m / z): 1572.51

[0162] Preparation of Compound 7

[0163] Compound 7 - 2 (9.0 g, 28.6 mmol, 1.0 eq) and pentane - 2,4 - dione (5.6 g, 57.2 mmol, 2.0 eq) were dissolved in 2 - ethoxyethanol, and then stirred at 110 °C for 24 hours under nitrogen reflux. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed from it using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 7 (11.8 g, 84%) was obtained.

[0164] MS (m / z): 988.29

[0165] <Preparation Example 3: Preparation of Compound 18>

[0166]

[0167] Preparation of Compound 18-1

[0168] Dissolve 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 to prepare a solution, and then add bis(pinacolato)diboron (12.8 g, 50.4 mmol, 1.5 eq), Pd(dppf)Cl2 (1.3 g, 1.68 mmol, 0.05 eq) and KOAc (9.9 g, 100.8 mmol, 3.0 eq) thereto, and then stir at 110 °C for 8 hours. After the reaction is completed, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 18-1 (11.7 g, 97%) is obtained.

[0169] MS(m / z): 344.25

[0170] Preparation of Compound 18-2

[0171] Dissolve Compound 18-1 (11.2 g, 32.5 mmol, 1.0 eq) in 1,4-dioxane and distilled water to prepare a solution, and then add 7-bromo-6-fluoroisoquinoline (7.3 g, 32.5 mmol, 1.0 eq), Pd(PPh3)4 (1.8 g, 1.62 mmol, 0.05 eq) and K2CO3 (13.4 g, 97.5 mmol, 3.0 eq) to the solution, and then stir at 110 °C for 12 hours. After the reaction is completed, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 18-2 (10.3 g, 88%) is obtained.

[0172] MS(m / z): 363.20

[0173] Preparation of Compound 18-3

[0174] Compound 18 - 2 (10.3 g, 28.6 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and then BBr3 was slowly added thereto at 0 °C, followed by stirring for 1 hour. After the reaction was completed, methanol was slowly added thereto at 0 °C, and then extraction was carried out with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as the eluent. Thus, compound 18 - 3 (9.5 g, 96%) was obtained.

[0175] MS (m / z): 349.18

[0176] Preparation of Compound 18 - 4

[0177] Compound 18 - 3 (9.5 g, 27.4 mmol, 1.0 eq) was dissolved in N - methyl - 2 - pyrrolidone to prepare a solution, and then K2CO3 (11.3 g, 82.2 mmol, 3.0 eq) was added thereto, followed by stirring at 120 °C for 12 hours. After the reaction was completed, extraction was carried out with distilled water and ethyl acetate at room temperature. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as the eluent. Thus, compound 18 - 4 (8.1 g, 90%) was obtained.

[0178] MS (m / z): 329.18

[0179] Preparation of Compound 18 - 5

[0180] Compound 18 - 4 (8.1 g, 24.6 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and then m - CPBA was added to the solution and stirred at room temperature for 24 hours. After the reaction was completed, layer separation was carried out with distilled water and dichloromethane, and then the organic layer was concentrated. The concentrated residue was dissolved in POCl3 (40 ml) and stirred at 80 °C for 4 hours. After the reaction was completed, POCl3 was removed therefrom using a rotary evaporator, and then saturated aqueous NaHCO3 solution was added thereto for neutralization. Layer separation was carried out with distilled water and dichloromethane, the organic layer was dried over anhydrous MgSO4, and the solvent was removed therefrom using a rotary evaporator. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the eluent, thereby obtaining compound 18 - 5 (7.4 g, 83%).

[0181] MS (m / z): 363.14

[0182] Preparation of Compound 18 - 6

[0183] Compound 18-5 (7.4 g, 24.0 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, phenylboronic acid (3.2 g, 26.4 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 h. After completion of the reaction, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 18-6 (9.0 g, 93%) was obtained.

[0184] MS (m / z): 405.21

[0185] Preparation of Compound 18-7

[0186] Compound 18-6 (9.0 g, 22.3 mmol, 2.0 eq) and iridium(III) chloride hydrate (3.3 g, 11.2 mmol, 1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then the mixture was stirred at 110 °C under nitrogen reflux for 24 h. The reaction mixture was cooled to room temperature, and then the resulting solid was filtered and washed with methanol. The solid was dried in vacuo to obtain compound 18-7 (9.5 g, 95%).

[0187] MS (m / z): 1796.76

[0188] Preparation of Compound 18

[0189] Compound 18-7 (9.5 g, 21.1 mmol, 1.0 eq) and pentane-2,4-dione (6.5 g, 42.0 mmol, 2.0 eq) were dissolved in 2-ethoxyethanol, and then the mixture was stirred at 110 °C under nitrogen reflux for 24 h. After completion of the reaction, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 18 (9.6 g, 83%) was obtained.

[0190] MS (m / z): 1100.41

[0191] <Preparation Example 4: Preparation of Compound 22>

[0192]

[0193] Preparation of Compound 22-1

[0194] Dissolve 6-bromo-5-methoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10 g, 33.6 mmol, 1.0 eq) in 1,4-dioxane to prepare a solution, then add bis(pinacolato)diboron (1.5 eq), Pd(dppf)Cl2 (0.05 eq) and KOAc (3.0 eq) thereto, and then stir at 110 °C for 8 hours. After the reaction is completed, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 22-1 (10.8 g, 94%) is obtained.

[0195] MS (m / z): 344.25

[0196] Preparation of Compound 22-2

[0197] Dissolve Compound 22-1 (10.8 g, 31.5 mmol, 1.0 eq) in 1,4-dioxane and distilled water to prepare a solution, then add 7-bromo-6-fluoroisoquinoline (1.0 eq), Pd(PPh3)4 (0.05 eq) and K2CO3 (3.0 eq) to the solution, and then stir at 110 °C for 12 hours. After the reaction is completed, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 22-2 (9.6 g, 84%) is obtained.

[0198] MS (m / z): 363.20

[0199] Preparation of Compound 22-3

[0200] Dissolve Compound 22-2 (9.6 g, 26.4 mmol, 1.0 eq) in dichloromethane to prepare a solution, and slowly add BBr3 thereto at 0 °C, then stir for 1 hour. After the reaction is completed, slowly add methanol thereto at 0 °C, and then extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 22-3 (9.2 g, 96%) is obtained.

[0201] MS (m / z): 363.20

[0202] Preparation of Compound 22-4

[0203] Dissolve Compound 22-3 (9.2 g, 25.3 mmol, 1.0 eq) in N-methyl-2-pyrrolidone, then add K2CO3 (3.0 eq) thereto, and subsequently stir at 120 °C for 12 hours. After completion of the reaction, extract with distilled water and ethyl acetate at room temperature. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 22-4 (7.9 g, 95%) is obtained.

[0204] MS (m / z): 329.18

[0205] Preparation of Compound 22-5

[0206] Dissolve Compound 22-4 (7.9 g, 24.0 mmol, 1.0 eq) in dichloromethane to prepare a solution, then add m-CPBA to the solution, and further stir at room temperature for 24 hours. After completion of the reaction, perform layer separation with distilled water and dichloromethane, and then concentrate the organic layer. Dissolve the concentrated residue in POCl3 (40 ml), and subsequently stir at 80 °C for 4 hours. After completion of the reaction, remove POCl3 therefrom using a rotary evaporator, and then add saturated aqueous NaHCO3 solution thereto for neutralization. Perform layer separation with distilled water and dichloromethane, dry the organic layer with anhydrous MgSO4, remove the solvent therefrom using a rotary evaporator, and then purify it by column chromatography using dichloromethane and hexane as eluents, thereby obtaining Compound 22-5 (7.4 g, 85%).

[0207] MS (m / z): 363.14

[0208] Preparation of Compound 22-6

[0209] Dissolve Compound 22-5 (7.4 g, 24.0 mmol, 1.0 eq) in 1,4-dioxane and distilled water to prepare a solution, then add phenylboronic acid (1.1 eq), Pd(PPh3)4 (0.05 eq) and K2CO3 (3.0 eq) to the solution, and further stir at 110 °C for 8 hours. After completion of the reaction, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 22-6 (8.9 g, 92%) is obtained.

[0210] MS (m / z): 405.21

[0211] Preparation of Compound 22-7

[0212] Dissolve Compound 22-6 (8.9 g, 22.0 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) in 2-ethoxyethanol and distilled water, and then stir at 110 °C under nitrogen reflux for 24 hours. Cool the reaction mixture to room temperature, then filter the resulting solid and wash it with methanol. Dry the solid under vacuum to obtain Compound 22-7 (8.9 g, 92%).

[0213] MS (m / z): 1766.71

[0214] Preparation of Compound 22

[0215] Dissolve Compound 22-7 (8.9 g, 20.2 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) in 2-ethoxyethanol, and then stir at 110 °C under nitrogen reflux for 24 hours. After the reaction is completed, cool the mixed solution to room temperature and extract it with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 22 (9.4 g, 85%) is obtained.

[0216] MS (m / z): 1100.41

[0217] <Preparation Example 5: Preparation of Compound 40>

[0218]

[0219] Preparation of Compound 40-1

[0220] Dissolve Compound 22-5 (10.0 g, 27.5 mmol, 1.0 eq) in 1,4-dioxane and distilled water to prepare a solution, then add 2-(4-(tert-butyl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.1 eq), Pd(PPh3)4 (0.05 eq) and K2CO3 (3.0 eq) thereto, and then stir at 110 °C for 8 hours. After the reaction is completed, cool the mixed solution to room temperature and extract it with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 40-1 (13.9 g, 93%) is obtained.

[0221] MS (m / z): 511.29

[0222] Preparation of Compound 40-2

[0223] Dissolve Compound 40-1 (13.9 g, 25.6 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) in 2-ethoxyethanol and distilled water, and then stir at 110 °C for 24 hours under nitrogen reflux. Cool the reaction mixture to room temperature, then filter the resulting solid and wash it with methanol. Dry the solid under vacuum to obtain Compound 40-2 (11.8 g, 90%).

[0224] MS (m / z): 2064.89

[0225] Preparation of Compound 40

[0226] Dissolve Compound 40-2 (11.8 g, 23.0 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) in 2-ethoxyethanol, and then stir at 110 °C for 24 hours under nitrogen reflux. After the reaction is completed, cool the mixed solution to room temperature and extract it with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 40 (11 g, 82%) is obtained.

[0227] MS (m / z): 1255.50

[0228] <Preparation Example 6: Preparation of Compound 41>

[0229]

[0230] Preparation of Compound 41-1

[0231] Dissolve Compound 22-5 (10.0 g, 27.5 mmol, 1.0 eq) in 1,4-dioxane and distilled water to prepare a solution, then add 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.1 eq), Pd(PPh3)4 (0.05 eq) and K2CO3 (3.0 eq) thereto, and then stir at 110 °C for 8 hours. After the reaction is completed, cool the mixed solution to room temperature and extract it with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 41-1 (13.9 g, 93%) is obtained.

[0232] MS (m / z): 511.29

[0233] Preparation of Compound 41-2

[0234] Dissolve Compound 41-1 (13.9 g, 25.6 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) in 2-ethoxyethanol and distilled water, and then stir at 110 °C under nitrogen reflux for 24 hours. Cool the reaction mixture to room temperature, then filter the resulting solid and wash it with methanol. Dry the solid under vacuum to obtain Compound 41-2 (11.9 g, 92%).

[0235] MS (m / z): 2028.89

[0236] Preparation of Compound 41

[0237] Dissolve Compound 41-2 (11.9 g, 23.5 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) in 2-ethoxyethanol, and then stir at 110 °C under nitrogen reflux for 24 hours. After the reaction is completed, cool the mixed solution to room temperature, and extract it with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent from it using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 41 (12 g, 83%) is obtained.

[0238] MS (m / z): 1243.50

[0239] <Preparation Example 7: Preparation of Compound 44>

[0240]

[0241] Preparation of Compound 44

[0242] Compound 44 is obtained in the same manner as the preparation method of Compound 41 in Preparation Example 6, except that 2,2,6,6-tetramethylheptane-3,5-dione is used instead of pentane-2,4-dione in Preparation Example 6.

[0243] MS (m / z): 1327.59

[0244] <Preparation Example 8: Preparation of Compound 45>

[0245]

[0246] Compound 45 is obtained in the same manner as the preparation method of Compound 41 in Preparation Example 6, except that 3,7-diethylnonane-4,6-dione is used instead of pentane-2,4-dione in Preparation Example 6.

[0247] MS (m / z): 1355.62

[0248] <Preparation Example 9: Preparation of Compound 46>

[0249]

[0250] Compound 46 was obtained in the same manner as in the preparation method of Compound 41 in Preparation Example 6, except that 3,7 - diethyl - 3,7 - dimethylnonane - 4,6 - dione was used instead of pentane - 2,4 - dione in Preparation Example 6.

[0251] MS (m / z): 1383.65

[0252] <Preparation Example 10: Preparation of Compound 47>

[0253]

[0254] Preparation of Compound 47

[0255] Compound 47 was obtained in the same manner as in the preparation method of Compound 41 in Preparation Example 6, except that 3,7 - diisopropyl - 2,3,7,8 - tetramethylnonane - 4,6 - dione was used instead of pentane - 2,4 - dione in Preparation Example 6.

[0256] MS (m / z): 1439.72

[0257] <Preparation Example 11: Preparation of Compound 54>

[0258]

[0259] Preparation of Compound 54

[0260] Compound 54 was obtained in the same manner as in the preparation method of Compound 41 in Preparation Example 6, except that (Z) - 5 - (cyclohexylamino) - 2,6 - dimethylheptan - 3 - one was used instead of pentane - 2,4 - dione in Preparation Example 6.

[0261] MS (m / z): 1380.65

[0262] <Preparation Example 12: Preparation of Compound 77>

[0263]

[0264] Preparation of Compound 77 - 1

[0265] Compound 18-1 (10.0 g, 29.0 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 6-bromo-7-fluoroisoquinoline (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 completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 77-1 (9.5 g, 90%) was obtained.

[0266] MS (m / z): 363.20

[0267] Preparation of Compound 77-2

[0268] Compound 77-1 (9.5 g, 26.1 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution. Then, BBr3 was slowly added thereto at 0 °C, and the mixture was stirred for 1 hour. After the reaction was completed, methanol was slowly added thereto at 0 °C, and then it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 77-2 (8.7 g, 96%) was obtained.

[0269] MS (m / z): 349.18

[0270] Preparation of Compound 77-3

[0271] Compound 77-2 (8.7 g, 25.0 mmol, 1.0 eq) was dissolved in N-methyl-2-pyrrolidone, and K2CO3 (3.0 eq) was added thereto. Subsequently, the mixture was stirred at 120 °C for 12 hours. After the reaction was completed, 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 therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 77-3 (7.6 g, 93%) was obtained.

[0272] MS (m / z): 329.18

[0273] Preparation of Compound 77-4

[0274] Compound 77-3 (7.6 g, 23.2 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 completed, liquid separation was performed using distilled water and dichloromethane, and then the organic layer was concentrated. The concentrated residue was dissolved in POCl3 (40 ml), and then stirred at 80 °C for 4 hours. After the reaction was completed, POCl3 was removed therefrom using a rotary evaporator, and then saturated aqueous NaHCO3 was added thereto for neutralization. Liquid separation was performed using distilled water and dichloromethane, the organic layer was dried over anhydrous MgSO4, the solvent was removed therefrom using a rotary evaporator, and then it was purified by column chromatography using dichloromethane and hexane as eluents to obtain Compound 77-4 (7.1 g, 85%).

[0275] MS (m / z): 363.14

[0276] Preparation of Compound 77-5

[0277] Compound 77-4 (7.1 g, 19.7 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution. Then, 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added thereto, and then stirred at 110 °C for 8 hours. After the reaction was completed, the mixed solution was cooled to room temperature and extracted using distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, the solvent was removed therefrom using a rotary evaporator, and then it was purified by column chromatography using dichloromethane and hexane as eluents to obtain Compound 77-5 (9.3 g, 93%).

[0278] MS (m / z): 511.29

[0279] Preparation of Compound 77-6

[0280] Compound 77-5 (9.3 g, 18.3 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 under nitrogen reflux for 24 hours. The reaction mixture was cooled to room temperature, and then the resulting solid was filtered and washed with methanol. The solid was dried in vacuo to obtain Compound 77-6 (9.4 g, 94%).

[0281] MS (m / z): 2191.03

[0282] Preparation of Compound 77

[0283] Compound 77-6 (9.4 g, 17.2 mmol, 1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol, and then stirred at 110 °C for 24 hours under nitrogen reflux. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 77 (11.1 g, 81%) was obtained.

[0284] MS (m / z): 1411.68

[0285] <Preparation Example 13: Preparation of Compound 85>

[0286]

[0287] Preparation of Compound 85

[0288] Compound 85 was obtained in the same manner as in the preparation of compound 41 in Preparation Example 6, except that (Z)-3,7-diethyl-6-hydroxy-3,7-dimethylnon-5-en-4-one-5-d was used instead of pentane-2,4-dione.

[0289] MS (m / z): 1356.63

[0290] <Preparation Example 14: Preparation of Compound 86>

[0291]

[0292] Preparation of Compound 86

[0293] Compound 86 was obtained in the same manner as in the preparation of compound 41 in Preparation Example 6, except that (Z)-3,7-diethyl-6-hydroxy-3,7-dimethylnon-5-en-4-one-5-d was used instead of pentane-2,4-dione.

[0294] MS (m / z): 1384.66

[0295] <Preparation Example 15: Preparation of Compound 106>

[0296]

[0297] Preparation of Compound 106-1

[0298] 3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-thiol (10 g, 33.4 mmol, 1.0 eq) was dissolved in 1,4-dioxane to prepare a solution, and then 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq) were added thereto, followed by stirring at 110 °C for 8 h. After completion of the reaction, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4, the solvent was removed therefrom using a rotary evaporator, and then it was purified by column chromatography using dichloromethane and hexane as eluents, thereby obtaining Compound 106-1 (11.0 g, 95%).

[0299] MS (m / z): 347.17

[0300] Preparation of Compound 106-2

[0301] Compound 106-1 (11.0 g, 31.7 mmol, 1.0 eq) was dissolved in DMSO, and then PdCl2 (0.05 eq) was added thereto, followed by stirring at 140 °C for 12 h. After completion of the reaction, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 106-2 (5.2 g, 48%) was obtained.

[0302] MS (m / z): 345.16

[0303] Preparation of Compound 106-3

[0304] Compound 106-2 (5.2 g, 15.2 mmol, 1.0 eq) was dissolved in dichloromethane to prepare a solution, and then m-CPBA was added to the solution, followed by stirring at room temperature for 24 h. After completion of the reaction, layer separation was carried out with distilled water and dichloromethane, and then the organic layer was concentrated. The concentrated residue was dissolved in POCl3 (40 ml), followed by stirring at 80 °C for 4 h. After completion of the reaction, POCl3 was removed therefrom using a rotary evaporator, and then saturated aqueous NaHCO3 solution was added thereto for neutralization. Layer separation was carried out with distilled water and dichloromethane, the organic layer was dried over anhydrous MgSO4, the solvent was removed therefrom using a rotary evaporator, and then it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 106-3 (5.0 g, 88%) was obtained.

[0305] MS (m / z): 379.12

[0306] Preparation of Compound 106-4

[0307] Compound 106-3 (5.0 g, 13.3 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 completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed from it using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 106-4 (5.2 g, 93%) was obtained.

[0308] MS (m / z): 421.19

[0309] Preparation of Compound 106-5

[0310] Compound 106-4 (5.2 g, 12.3 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 then the resulting solid was filtered and washed with methanol. The solid was dried in vacuo to obtain Compound 106-5 (6.0 g, 92%).

[0311] MS (m / z): 2136.58

[0312] Preparation of Compound 106

[0313] Compound 106-5 (6.0 g, 11.3 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) were dissolved in 2-ethoxyethanol, and then stirred at 110 °C for 24 hours under nitrogen reflux. After the reaction was completed, the mixed solution 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 from it using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 106 (5.6 g, 88%) was obtained.

[0314] MS (m / z): 1132.36

[0315] <Preparation Example 16: Preparation of Compound 120>

[0316]

[0317] Preparation of Compound 120-1

[0318] Dissolve Compound 106-3 (10.0 g, 26.3 mmol, 1.0 eq) in 1,4-dioxane and distilled water to prepare a solution. Then add 4,4,5,5-tetramethyl-2-(4-(propan-2-yl-2-d)naphthalen-2-yl)-1,3,2-dioxaborolane (1.1 eq), Pd(PPh3)4 (0.05 eq) and K2CO3 (3.0 eq) to the solution, and stir at 110 °C for 8 hours. After the reaction is completed, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, remove the solvent therefrom using a rotary evaporator, and then purify it by column chromatography using dichloromethane and hexane as eluents to obtain Compound 120-1 (12.4 g, 92%).

[0319] MS (m / z): 514.26

[0320] Preparation of Compound 120-2

[0321] Dissolve Compound 120-1 (12.4 g, 24.2 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) in 2-ethoxyethanol and distilled water, and then stir at 110 °C for 24 hours under nitrogen reflux. Cool the reaction mixture to room temperature, then filter the resulting solid and wash it with methanol. Dry the solid under vacuum to obtain Compound 120-2 (13.0 g, 90%).

[0322] MS (m / z): 2396.73

[0323] Preparation of Compound 120

[0324] Dissolve Compound 120-2 (13.0 g, 21.7 mmol, 1.0 eq) and pentane-2,4-dione (2.0 eq) in 2-ethoxyethanol, and then stir at 110 °C for 24 hours under nitrogen reflux. After the reaction is completed, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, and then remove the solvent therefrom using a rotary evaporator. Then purify it by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 120 (11.6 g, 85%) is obtained.

[0325] MS (m / z): 1262.44

[0326] <Preparation Example 17: Preparation of Compound 121>

[0327]

[0328] Preparation of Compound 121

[0329] Compound 121 was obtained in the same manner as the preparation method of Compound 120 in Preparation Example 16, except that 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 4,4,5,5-tetramethyl-2-(4-(propan-2-yl-2-d)naphthalen-2-yl)-1,3,2-dioxaborolane in the preparation of Compound 120-1 in Preparation Example 16.

[0330] MS(m / z): 1275.45

[0331] <Preparation Example 18: Preparation of Compound 133>

[0332]

[0333] Preparation of Compound 133-1

[0334] 7-Bromoisoquinoline-6-thiol (10 g, 41.6 mmol, 1.0 eq) was dissolved in 1,4-dioxane to prepare a solution, and then 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane (1.1 eq), Pd(PPh3)4 (0.05 eq) and K2CO3 (3.0 eq) were added to the solution, and then stirred at 110 °C for 8 hours. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 133-1 (13.5 g, 94%) was obtained.

[0335] MS(m / z): 347.17

[0336] Preparation of Compound 133-2

[0337] Compound 133-1 (13.5 g, 39.1 mmol, 1.0 eq) was dissolved in DMSO to prepare a solution, and then PdCl2 (0.05 eq) was added thereto, and then stirred at 140 °C for 12 hours. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 133-2 (6.5 g, 48%) was obtained.

[0338] MS (m / z): 345.16

[0339] Preparation of Compound 133-3

[0340] Dissolve Compound 133-2 (6.5 g, 18.7 mmol, 1.0 eq) in dichloromethane to prepare a solution. Then, add m-CPBA to the solution and stir at room temperature for 24 hours. After the reaction is complete, perform liquid-liquid separation with distilled water and dichloromethane, and then concentrate the organic layer. Dissolve the concentrated residue in POCl3 (40 ml), and then stir at 80 °C for 4 hours. After the reaction is complete, remove POCl3 using a rotary evaporator, and then add saturated aqueous NaHCO3 for neutralization. Perform liquid-liquid separation with distilled water and dichloromethane, dry the organic layer with anhydrous MgSO4, remove the solvent using a rotary evaporator, and then purify it by column chromatography using dichloromethane and hexane as eluents to obtain Compound 133-3 (6.7 g, 90%).

[0341] MS (m / z): 379.12

[0342] Preparation of Compound 133-4

[0343] Dissolve Compound 133-3 (6.7 g, 17.8 mmol, 1.0 eq) in 1,4-dioxane and distilled water to prepare a solution. Then, add 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.1 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (3.0 eq), and then stir at 110 °C for 8 hours. After the reaction is complete, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4, remove the solvent using a rotary evaporator, and then purify it by column chromatography using dichloromethane and hexane as eluents to obtain Compound 133-4 (8.7 g, 93%).

[0344] MS (m / z): 527.26

[0345] Preparation of Compound 133-5

[0346] Dissolve Compound 133-4 (8.7 g, 16.5 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) in 2-ethoxyethanol and distilled water, and then stir at 110 °C under nitrogen reflux for 24 hours. Cool the reaction mixture to room temperature, then filter the resulting solid and wash it with methanol. Dry the solid under vacuum to obtain Compound 133-5 (9.4 g, 91%).

[0347] MS (m / z): 2517.84

[0348] Preparation of Compound 133

[0349] Dissolve Compound 133-5 (9.4 g, 15.0 mmol, 1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) in 2-ethoxyethanol, and then stir at 110 °C for 24 hours under nitrogen reflux. After the reaction is completed, cool the mixed solution to room temperature and extract with distilled water and dichloromethane. Dry the organic layer with anhydrous MgSO4 and then remove the solvent therefrom using a rotary evaporator. Then, purify it by column chromatography using dichloromethane and hexane as the eluent. Thus, Compound 133 (9.6 g, 89%) is obtained.

[0350] MS (m / z): 1443.64

[0351] <Preparation Example 19: Preparation of Compound 134>

[0352]

[0353] Preparation of Compound 134

[0354] Compound 134 is obtained in the same manner as the preparation method of Compound 133 in Preparation Example 18, except that 3,7-diethyl-3,7-dimethylnonane-4,6-dione is used instead of 3,7-diethylnonane-4,6-dione in Preparation Example 18.

[0355] MS (m / z): 1471.67

[0356] <Preparation Example 20: Preparation of Compound 135>

[0357]

[0358] Preparation of Compound 135

[0359] Compound 135 is obtained in the same manner as the preparation method of Compound 133 in Preparation Example 18, except that 3,7-diisopropyl-2,3,7,8-tetramethylnonane-4,6-dione is used instead of 3,7-diethylnonane-4,6-dione in Preparation Example 18.

[0360] MS (m / z): 1527.73

[0361] <Preparation Example 21: Preparation of Compound 139>

[0362]

[0363] Preparation of Compound 139

[0364] Compound 139 was obtained in the same manner as the preparation method of Compound 133 in Preparation Example 18, except that (3Z,5E)-5-(isopropylimino)-2,6-dimethylhept-3-en-3-ol was used instead of 3,7-diethylnonane-4,6-dione in Preparation Example 18.

[0365] MS(m / z): 1428.64

[0366] <Preparation Example 22: Preparation of Compound 170>

[0367]

[0368] Preparation of Compound 170-1

[0369] 6-Bromo-7-iodo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10 g, 25.4 mmol, 1.0 eq), Pd(PPh3)4 (0.03 eq) and CuI (0.03 eq) were placed in a reaction vessel, and Et3N (300 ml) and trimethylsilylacetylene (1.5 eq) were added thereto under a nitrogen atmosphere. The reaction solution was stirred at 80 °C for 16 hours. After completion of the reaction, the solvent was removed therefrom using a rotary evaporator, and then it was purified by column chromatography using hexane as the eluent to obtain Compound 170-1 (8.7 g, 95%).

[0370] MS(m / z): 363.41

[0371] Preparation of Compound 170-2

[0372] 9H2O (2.4 eq) was dissolved in N-methylpyrrolidone to prepare a solution, and then Compound 170-1 (24.1 mmol) was added to the solution, and the mixture was stirred at 180 °C for 12 hours. After completion of the reaction, an aqueous saturated ammonium chloride solution was added thereto, and the resulting solid was filtered and washed with distilled water and methanol. Then it was purified by column chromatography using hexane and dichloromethane as the eluents. Thus, Compound 170-2 (4.1 g, 70%) was obtained.

[0373] MS(m / z): 244.40

[0374] Preparation of Compound 170-3

[0375] Compound 170-2 (16.8 mmol) was dissolved in THF to prepare a solution, and then n-BuLi (1.5 eq) was slowly added thereto at -78 °C, followed by stirring for 30 minutes. Triisopropyl borate (1.5 eq) was added to the reaction solution, and then the mixture was stirred at room temperature for 1 hour. Then, HCl was added to the reaction solution and stirred for 1 hour. After completion of the reaction, extraction was performed with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, compound 170-3 (4.6 g, 95%) was obtained.

[0376] MS (m / z): 288.21

[0377] Preparation of Compound 170-4

[0378] Compound 170-3 (4.6 g, 15.9 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution, and then 4-bromo-6-chloronicotinaldehyde (1.1 eq), Pd(PPh3)4 (0.05 eq) and K2CO3 (3.0 eq) were added to the solution, followed by stirring at 110 °C for 8 hours. After completion of the reaction, the mixed solution was cooled to room temperature and extraction was performed with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents, thereby obtaining compound 170-4 (5.6 g, 92%).

[0379] MS (m / z): 383.93

[0380] Preparation of Compound 170-5

[0381] Chloro(methoxymethyl)triphenylphosphonium (1.5 eq) was dissolved in THF to prepare a solution, and then potassium tert-butoxide (1.6 eq) was added thereto at room temperature, followed by stirring for 30 minutes. Compound 170-4 (5.6 g, 14.6 mmol, 1 eq) was added to the reaction solution, and then the mixture was stirred at room temperature for 4 hours. After completion of the reaction, extraction was performed with distilled water and ethyl acetate. The organic layer was dried over anhydrous MgSO4 and the solvent was removed therefrom using a rotary evaporator. The concentrated residue was dissolved in dichloromethane to prepare a solution, and then methanesulfonic acid was added thereto, followed by stirring under reflux for 4 hours. Thus, compound 170-5 (4.4 g, 80%) was obtained without further purification.

[0382] MS (m / z): 379.95

[0383] Preparation of Compound 170-6

[0384] Compound 170-5 (4.4 g, 11.6 mmol, 1.0 eq) was dissolved in 1,4-dioxane and distilled water to prepare a solution, and then 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.1 eq), Pd(PPh3)4 (0.05 eq) and K2CO3 (3.0 eq) were added thereto, and then the mixture was stirred at 110 °C for 8 hours. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents to obtain Compound 170-6 (5.7 g, 94%).

[0385] MS (m / z): 527.77

[0386] Preparation of Compound 170-7

[0387] Compound 170-6 (5.7 g, 10.9 mmol, 2.0 eq) and iridium(III) chloride hydrate (1.0 eq) were dissolved in 2-ethoxyethanol and distilled water, and then the mixture was stirred at 110 °C for 24 hours under nitrogen reflux. The reaction mixture was cooled to room temperature, and then the resulting solid was filtered and washed with methanol. The solid was dried in vacuo to obtain Compound 170-7 (6.2 g, 91%).

[0388] MS (m / z): 2523.48

[0389] Preparation of Compound 170

[0390] Compound 170-7 (6.2 g, 9.9 mmol, 1.0 eq) and 3,7-diethylnonane-4,6-dione (2.0 eq) were dissolved in 2-ethoxyethanol, and then the mixture was stirred at 110 °C for 24 hours under nitrogen reflux. After the reaction was completed, the mixed solution was cooled to room temperature and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO4 and then the solvent was removed therefrom using a rotary evaporator. Then, it was purified by column chromatography using dichloromethane and hexane as eluents. Thus, Compound 170 (4.3 g, 61%) was obtained.

[0391] MS (m / z): 1457.07

[0392] <Preparation Example 23: Preparation of Compound 176>

[0393]

[0394] Preparation of Compound 176

[0395] Compound 176 was obtained in the same manner as in the preparation of Compound 170 in Preparation Example 22, except that (Z)-3,7-diethyl-6-hydroxynon-5-en-4-one-5-d was used instead of 3,7-diethylnonane-4,6-dione in Preparation Example 22.

[0396] MS(m / z): 1457.65

[0397] <Preparation Example 24: Preparation of Compound 177>

[0398]

[0399] Preparation of Compound 177

[0400] Compound 177 was obtained in the same manner as in the preparation of Compound 170 in Preparation Example 22, except that 3,7-diethyl-3,7-dimethylnonane-4,6-dione was used instead of 3,7-diethylnonane-4,6-dione in Preparation Example 22.

[0401] MS(m / z): 1485.12

[0402] <Preparation Example 25: Preparation of Compound 179>

[0403]

[0404] Preparation of Compound 179

[0405] Compound 179 was obtained in the same manner as in the preparation of Compound 170 in Preparation Example 22, except that (3Z,5E)-5-(cyclohexylamino)-2,6-dimethylhept-3-en-3-ol was used instead of 3,7-diethylnonane-4,6-dione in Preparation Example 22.

[0406] MS(m / z): 1481.68

[0407] <Preparation Example 26: Preparation of Compound 181>

[0408]

[0409] Preparation of Compound 181

[0410] Compound 181 was obtained in the same manner as in the preparation of Compound 170 in Preparation Example 22, except that 2-(4-(tert-butyl)naphthalen-2-yl-1,3,5,6,7,8-d6)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in Preparation Example 22.

[0411] MS(m / z): 1493.17

[0412] <Preparation Example 27: Preparation of Compound 182>

[0413]

[0414] Preparation of Compound 182

[0415] Compound 182 was obtained in the same manner as in the preparation of Compound 170 in Preparation Example 22, except that 2-chloro-8,8,11,11-tetramethyl-8,9,10,11-tetrahydronaphtho[2',3':4,5]thieno[2,3-f]isoquinoline-1,4,5,6,7,12-d6 was used instead of 2-chloro-8,8,11,11-tetramethyl-8,9,10,11-tetrahydronaphtho[2',3':4,5]thieno[2,3-f]isoquinoline.

[0416] MS(m / z): 1495.18

[0417] <Preparation Example 28: Preparation of Compound 183>

[0418]

[0419] Preparation of Compound 183

[0420] Compound 183 was obtained in the same manner as in the preparation of Compound 182 in Preparation Example 27, except that 2-(4-(tert-butyl)naphthalen-2-yl-1,3,5,6,7,8-d6)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

[0421] MS(m / z): 1503.23

[0422] Example

[0423] <Current Example 1>

[0424] On which was coated with a thickness of The glass substrate of ITO (indium tin oxide) thin film is cleaned, and then ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone or methanol. Then, the glass substrate is dried. Thus, an ITO transparent electrode is formed.

[0425] HI-1 as a hole injection material is deposited on the ITO transparent electrode by thermal vacuum deposition. Thus, a hole injection layer with a thickness of 60 nm is formed. Then, NPB as a hole transport material is deposited on the hole injection layer by thermal vacuum deposition. Thus, a hole transport layer with a thickness of 80 nm is formed. Then, CBP as a matrix material of the light-emitting layer is deposited on the hole transport layer by thermal vacuum deposition. Compound 1 as a dopant is doped into the matrix material at a doping concentration of 5%. Thus, a light-emitting layer with a thickness of 30 nm is formed. ET-1:Liq(1:1)(30 nm) as a material for the electron transport layer and electron injection layer is deposited on the light-emitting layer. Then, aluminum with a thickness of 100 nm is deposited thereon to form a negative electrode. In this way, an organic light-emitting diode is manufactured. The materials used in the current Example 1 are as follows.

[0426]

[0427]

[0428] HI-1 is NPNPB and ET-1 is ZADN.

[0429] <Current Example 2>

[0430] An organic light-emitting diode is manufactured in the same manner as in Current Example 1, except that Compound 7 is used instead of Compound 1 in Current Example 1.

[0431] <Current Example 3>

[0432] An organic light-emitting diode is manufactured in the same manner as in Current Example 1, except that Compound 18 is used instead of Compound 1 in Current Example 1.

[0433] <Current Example 4>

[0434] An organic light-emitting diode is manufactured in the same manner as in Current Example 1, except that Compound 22 is used instead of Compound 1 in Current Example 1.

[0435] <Current Example 5>

[0436] An organic light-emitting diode is manufactured in the same manner as in Current Example 1, except that Compound 40 is used instead of Compound 1 in Current Example 1.

[0437] <Current Example 6>

[0438] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 41 is used instead of Compound 1 in Current Example 1.

[0439] <Current Example 7>

[0440] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 44 is used instead of Compound 1 in Current Example 1.

[0441] <Current Example 8>

[0442] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 45 is used instead of Compound 1 in Current Example 1.

[0443] <Current Example 9>

[0444] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 46 is used instead of Compound 1 in Current Example 1.

[0445] <Current Example 10>

[0446] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 47 is used instead of Compound 1 in Current Example 1.

[0447] <Current Example 11>

[0448] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 54 is used instead of Compound 1 in Current Example 1.

[0449] <Current Example 12>

[0450] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 77 is used instead of Compound 1 in Current Example 1.

[0451] <Current Example 13>

[0452] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 85 is used instead of Compound 1 in Current Example 1.

[0453] <Current Example 14>

[0454] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 86 is used instead of Compound 1 in Current Example 1.

[0455] <Current Example 15>

[0456] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 106 is used instead of Compound 1 in Current Example 1.

[0457] <Current Example 16>

[0458] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 120 is used instead of Compound 1 in Current Example 1.

[0459] <Current Example 17>

[0460] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 121 is used instead of Compound 1 in Current Example 1.

[0461] <Current Example 18>

[0462] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 133 is used instead of Compound 1 in Current Example 1.

[0463] <Current Example 19>

[0464] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 134 is used instead of Compound 1 in Current Example 1.

[0465] <Current Example 20>

[0466] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 135 is used instead of Compound 1 in Current Example 1.

[0467] <Current Example 21>

[0468] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 139 is used instead of Compound 1 in Current Example 1.

[0469] <Current Example 22>

[0470] An organic light-emitting diode is fabricated in the same manner as in Current Example 1, except that Compound 170 is used instead of Compound 1 in Current Example 1.

[0471] <Current Example 23>

[0472] An organic light-emitting diode was fabricated in the same manner as in Current Example 1, except that Compound 176 was used instead of Compound 1 in Current Example 1.

[0473] <Current Example 24>

[0474] An organic light-emitting diode was fabricated in the same manner as in Current Example 1, except that Compound 177 was used instead of Compound 1 in Current Example 1.

[0475] <Current Example 25>

[0476] An organic light-emitting diode was fabricated in the same manner as in Current Example 1, except that Compound 179 was used instead of Compound 1 in Current Example 1.

[0477] <Current Example 26>

[0478] An organic light-emitting diode was fabricated in the same manner as in Current Example 1, except that Compound 181 was used instead of Compound 1 in Current Example 1.

[0479] <Current Example 27>

[0480] An organic light-emitting diode was fabricated in the same manner as in Current Example 1, except that Compound 182 was used instead of Compound 1 in Current Example 1.

[0481] <Current Example 28>

[0482] An organic light-emitting diode was fabricated in the same manner as in Current Example 1, except that Compound 183 was used instead of Compound 1 in Current Example 1.

[0483] <Comparative Example 1>

[0484] An organic light-emitting diode was fabricated in the same manner as in Current Example 1, except that an RD having the following structure was used instead of Compound 1 in Current Example 1.

[0485]

[0486] Test Example

[0487] The organic light-emitting diodes fabricated in Current Examples 1 to 28 and the Comparative Example were connected to an external power supply, and the characteristics of the organic light-emitting diodes were evaluated using a constant current source and a photometer at room temperature.

[0488] Specifically, at 10 mA / cm 2The operating voltage (%), external quantum efficiency (EQE; %), lifetime characteristics (LT95; %), full width at half maximum (FWHM) (%), and aspect ratio (%) were measured at a current density of , and the relative values with respect to those of Comparative Example 1 were calculated. The results are shown in Table 1 below.

[0489] The LT95 lifetime refers to the time it takes for the display element to lose 5% of its initial brightness. LT95 is the most difficult customer specification to meet. Whether image burn-in occurs on the display can be determined based on LT95.

[0490] The full width at half maximum (FWHM) refers to the wavelength width corresponding to 1 / 2 of the maximum value of the curve representing the wavelength. A narrow FWHM means high color purity, which means that the light-emitting diode can efficiently achieve the combination of light beams to present the desired color and a high color gamut can be obtained. The full width at half maximum is evaluated by photoluminescence (PL) intensity measurement, and the model / manufacturer of the measurement device is FS-5 / Edinburgh Instruments.

[0491] The aspect ratio is calculated based on the following: {(the length of the major axis of the metal-centered molecule (N-metal-N direction)) / (the length of the minor axis perpendicular to the major axis of the metal-centered molecule)}. The aspect ratio is measured based on the results of calculating the distances between atoms in the molecule using the Gaussian molecular calculation program (Gaussian 16).

[0492]

Table 1

[0493]

[0494]

[0495]

[0496] From the results in Table 1, it can be determined that the organometallic compounds used in each of Examples 1 to 28 of the present invention satisfy the structure represented by Chemical Formula I of the present disclosure. Compared with the organic light-emitting diodes in Comparative Example 1 using dopants that do not satisfy the structure represented by Chemical Formula I of the present disclosure, the organic light-emitting diodes in which the dopant of the light-emitting layer is made of each of Examples 1 to 28 of the present invention have a lower operating voltage and a higher aspect ratio, and have an improved external quantum efficiency (EQE) and lifetime (LT95). In addition, the organic light-emitting diodes in which the dopant of the light-emitting layer is made of each of Examples 1 to 28 of the present invention have a narrow full width at half maximum, resulting in improved color purity.

[0497] Although the embodiments of the present disclosure have been described in more detail with reference to the accompanying drawings, the present disclosure is not necessarily limited to these embodiments and can be modified in various ways within the technical spirit of the present disclosure. Therefore, the embodiments disclosed in the present disclosure are intended to describe rather than limit the technical concept of the present disclosure, and the scope of the technical concept of the present disclosure is not limited by these embodiments. Therefore, it should be understood that the above-described embodiments are not restrictive in all aspects but illustrative.

Claims

1. An organometallic compound represented by one selected from the group consisting of the following compounds:

2. An organic light-emitting diode, comprising: A first electrode; A second electrode facing the first electrode; And An organic layer disposed between the first electrode and the second electrode; Wherein the organic layer includes a light-emitting layer, Wherein the light-emitting layer contains a doping material, Wherein the doping material includes the organometallic compound according to claim 1.

3. The organic light-emitting diode according to claim 2, wherein the light-emitting layer is a red phosphorescent light-emitting layer.

4. The organic light-emitting diode according to claim 2, wherein the organic layer further includes 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.

5. An organic light-emitting diode, comprising: A first electrode and a second electrode facing each other; And A first light-emitting stack and a second light-emitting stack located between the first electrode and the second electrode, Wherein each of the first light-emitting stack and the second light-emitting stack includes at least one light-emitting layer, Wherein at least one of the light-emitting layers is a red phosphorescent light-emitting layer, Wherein the red phosphorescent light-emitting layer contains a doping material, Wherein the doping material includes the organometallic compound according to claim 1.

6. An organic light-emitting diode, comprising: A first electrode and a second electrode facing each other; And A first light-emitting stack, a second light-emitting stack, and a third light-emitting stack located between the first electrode and the second electrode, Wherein 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, Wherein at least one of the light-emitting layers is a red phosphorescent light-emitting layer, Wherein the red phosphorescent light-emitting layer contains a doping material, Wherein the doping material includes the organometallic compound according to claim 1.

7. An organic light-emitting display device, comprising: A substrate; A driving element located on the substrate; And An organic light-emitting diode disposed on the substrate and connected to the driving element, wherein the organic light-emitting diode includes the organic light-emitting diode according to any one of claims 2 to 6.

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