Organic metal compound and organic light emitting diode comprising the same

Abstract

Describes a novel organometallic compound represented by the following Chemical Formula I: #imgabs0# wherein R represents a fused ring connected to X1 and X2, and its variables are defined as herein. The organometallic compound serves as a dopant for the light-emitting layer of an organic light-emitting diode. The organic light-emitting device includes the organic light-emitting diode and can be a display device or a lighting device. Improved color gamut, luminous efficiency, and lifetime of the diode, as well as reduced operating voltage of the diode, are achieved.

Description

Technical Field

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

[0002] Display devices are useful in various fields, and there is a need to provide an improved display device. In particular, organic light emitting display devices including organic light emitting diodes (OLEDs) are rapidly developing.

[0003] In OLED, when charges are injected into the light-emitting layer formed between the positive electrode and the negative electrode, electrons and holes recombine with each other in the light-emitting layer to form excitons, and the energy of the excitons is converted into light. In this way, OLED emits light. Summary of the invention

[0004] Compared to conventional display devices, organic light-emitting diodes can operate at low voltages, consume less power, exhibit excellent colors, and can be used in a variety of ways. Organic light-emitting diodes can also be formed on flexible substrates to provide a flexible or foldable device. In addition, the size of OLEDs can be adjusted.

[0005] Compared with liquid crystal displays (LCDs), OLEDs have excellent viewing angles and contrast, and because OLEDs do not require a backlight, they are lightweight and ultra-thin. OLEDs may include multiple organic layers between a negative electrode (e.g., an electron injection electrode, a cathode, etc.) and a positive electrode (e.g., a hole injection electrode, an anode, etc.). The multiple organic layers may include a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, and a light-emitting layer, an electron transport layer, etc.

[0006] In the OLED structure described in this article, when voltage is applied to the two electrodes, electrons and holes are injected into the light-emitting layer from the negative electrode and the positive electrode, respectively, thereby generating excitons in the light-emitting layer, which then drop to the ground state in the process to emit light.

[0007] Organic materials used in organic light-emitting diodes can be roughly divided into luminescent materials and charge transport materials. The luminescent material is an important factor in determining the luminous efficiency of organic light-emitting diodes. The luminescent material must have high quantum efficiency, excellent electron and hole mobility, and must be uniformly and stably present in the luminescent layer. The luminescent material can be divided into luminescent materials that emit blue, red and green light according to the color of the light. The chromogenic material can include a host and a dopant to improve the color purity and luminous efficiency through energy transfer.

[0008] When a fluorescent material is used, about 25% of the singlet states of the excitons generated in the light emitting layer are used to emit light, while most of the triplet states of 75% of the excitons generated in the light emitting layer are dissipated as heat. However, when a phosphorescent material is used, both singlet and triplet states are used to emit light.

[0009] Conventionally, organometallic compounds are used as phosphorescent materials in organic light emitting diodes. Research and development of phosphorescent materials are constantly required to solve the problems of low efficiency and lifetime.

[0010] Therefore, an object of the present invention is to provide an organic metal compound capable of reducing operating voltage and improving efficiency and lifespan, and an organic light emitting diode including an organic light emitting layer containing the same.

[0011] The purpose of the present disclosure is not limited to the above-mentioned purpose. Other unmentioned purposes and advantages of the present disclosure can be understood from the following description, and can be more clearly understood from the embodiments of the present disclosure. In addition, it is easy to understand that the purposes and advantages of the present disclosure can be achieved using the means and combinations thereof shown in the claims.

[0012] In one aspect, the present disclosure provides an organometallic compound having a novel structure represented by the following Chemical Formula I, and an organic light emitting diode in which a phosphorescent light emitting layer comprises the same as a dopant of the phosphorescent light emitting layer.

[0013]

[0014] Wherein in Chemical Formula I:

[0015] M represents a metal that is one of Mo, W, Re, Ru, Os, Rh, Ir, Pd, Pt and Au;

[0016] R a represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino;

[0017] Each of X1 and X2 represents carbon;

[0018] X3 to X6 are each independently selected from CRb and one of N;

[0019] Optionally, two R on two adjacent ones of X3 to X6 b may be connected to each other to form a cyclic structure, the cyclic structure comprising one selected from the group consisting of a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C20 heterocycloalkyl group, a substituted or unsubstituted C7-C20 aralkyl group, a substituted or unsubstituted C2-C20 heteroaralkyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group,

[0020] R b represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino;

[0021] (Z1-Z2) represents a bidentate ligand;

[0022] m is an integer selected from 1, 2 or 3, n is an integer selected from 0, 1 or 2, wherein the sum of m and n is the oxidation number of said M;

[0023] R represents a fused ring connected to X1 and X2, and comprises one selected from the group consisting of the following chemical formula II to chemical formula IV:

[0024]

[0025]

[0026]

[0027] Wherein in the chemical formula II to the chemical formula IV,

[0028] Y represents the selection of BR 19 , CR 19 R 20 、C=O、CNR 19 、SiR 19 R 20 NR19 , PR 19 , AsR 19 , SbR 19 、P(O)R 19 、P(S)R 19 、P(Se)R 19 、As(O)R 19 、As(S)R 19 、As(Se)R 19 、Sb(O)R 19 、Sb(S)R 19 、Sb(Se)R 19 , one of the group consisting of O, N, S, Se, Te, SO, SO2, SeO, SeO2, TeO, and TeO2;

[0029] R1 to R 18 each independently represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino;

[0030] R 19 and R 20 Each independently represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino.

[0031] The organometallic compound according to the present disclosure may be used as a dopant of a light-emitting layer of an organic light-emitting diode, thereby reducing the operating voltage of the organic light-emitting diode and improving the efficiency and lifespan characteristics of the organic light-emitting diode.

[0032] The effects of the present disclosure are not limited to the above-mentioned effects, and other unmentioned effects will be clearly understood by those skilled in the art from the following description. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 is a cross-sectional view schematically illustrating an organic light emitting diode in which a light emitting layer includes an organic metal compound according to an embodiment of the present disclosure.

[0034] Figure 2 is a cross-sectional view schematically showing an organic light emitting diode having a tandem structure including two light emitting stacks and including the organometallic compound represented by Chemical Formula I according to an embodiment of the present disclosure.

[0035] Figure 3 is a cross-sectional view schematically showing an organic light emitting diode having a tandem structure including three light emitting stacks and including the organometallic compound represented by Chemical Formula I according to an embodiment of the present disclosure.

[0036] Figure 4 is a cross-sectional view schematically illustrating an organic light emitting display device including an organic light emitting diode according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0037] The advantages and features of the present disclosure, as well as methods for achieving these advantages and features, will be described in detail below and in the accompanying drawings. Figure 1 The embodiments described in detail above will become apparent. However, the content of the present disclosure is not limited to the embodiments disclosed below, and can be implemented in various forms and variations. Therefore, these embodiments are proposed only to make the present disclosure complete and to fully inform the scope of the present disclosure to those of ordinary skill in the art to which the present disclosure belongs. All components of each OLED and each organic light emitting display device according to all embodiments of the present disclosure are operably coupled and arranged.

[0038] The shapes, sizes, ratios, angles, numbers, etc. disclosed in the accompanying drawings for describing the embodiments of the present disclosure are illustrative, and the present disclosure is not limited thereto. The same reference numerals refer to the same elements here. In addition, in order to simplify the description, the description and details of well-known steps and elements are omitted. In addition, in the following detailed description of the present disclosure, many specific details are set forth to provide a comprehensive understanding of the present disclosure. However, it is understood that the invention can be implemented without these specific details. In other cases, well-known methods, procedures, elements and circuits are not described in detail to avoid unnecessary concealment of various aspects of the present disclosure.

[0039] The terms used herein are only for the purpose of describing specific embodiments and are not intended to limit the present disclosure. As used herein, the singular formations "a" and "an" are intended to also include plural formations, unless the context clearly indicates. It should be further understood that the terms "include", "comprise", "include", and "include" used in this specification refer to the presence of the described features, integers, operations, elements and / or components, but do not exclude the presence or increase of one or more other features, integers, operations, elements, components and / or parts thereof. As used herein, the term "and / or" includes any and all combinations of one or more related listed items. For example, an expression such as "at least one", when placed in front of a list of elements, can modify the entire list of elements without modifying a single element in the list. When interpreting numerical values, errors or tolerances may occur even without a clear description.

[0040] In addition, it is also understood that when a first element or layer is referred to as being present on a second element or layer, the first element may be directly disposed on the second element, or may be indirectly disposed on the second element, and a third element or layer may be disposed between the first and second elements or layers. It is understood that when an element or layer is referred to as being "connected to" or "coupled to" another element or layer, it may be directly on, connected to, or coupled to the other element or layer, or one or more intermediate elements or layers may be present. In addition, it is also understood that when an element or layer is referred to as being "between" two elements or layers, it may be the only element or layer between the two elements or layers, or one or more intermediate elements or layers may also be present.

[0041] Further, as used herein, when a layer, film, region, plate, etc. is set on the "upper" or "top" of another layer, film, region, plate, etc., the former can directly contact the latter or still another layer, film, region, plate, etc. can be set between the former and the latter. As used herein, when a layer, film, region, plate, etc. is directly set on the "upper" or "top" of another layer, film, region, plate, etc., the former directly contacts the latter, and another layer, film, region, plate, etc. are not set between the former and the latter. In addition, as used herein, when a layer, film, region, plate, etc. is set on the "bottom" or "below" of another layer, film, region, plate, etc., the former can directly contact the latter, or another layer, film, region, plate, etc. can be set between the former and the latter. As used herein, when a layer, film, region, plate, etc. is directly set on the "bottom" or "below" of another layer, film, region, plate, etc., the former directly contacts the latter, and another layer, film, region, plate, etc. are not set between the former and the latter.

[0042] In descriptions of temporal relationships, such as a temporal precedence relationship between two events, such as "after," "subsequently," "before," etc., unless "directly after," "directly subsequent," or "directly before" is not specified, the other event may occur in between.

[0043] It will 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. Therefore, the first element, component, region, layer or part described below may be referred to as a second element, component, region, layer or part without departing from the spirit and scope of the present disclosure.

[0044] The features of the various embodiments of the present disclosure may be partially or completely combined with each other, and may be technically related or interoperable with each other. The various embodiments may be implemented independently of each other, or may be implemented together in an associated relationship.

[0045] When interpreting a numerical value, the numerical value is interpreted as including a range of error unless otherwise expressly stated.

[0046] It will be understood that when an element or layer is referred to as being “connected to” or “coupled to” another element or layer, it can be directly on, connected to or coupled to the other element or layer, or one or more intervening elements or layers may be present. Additionally, it will 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 one or more intervening elements or layers may also be present.

[0047] The features of various embodiments of the present disclosure may be partially or completely combined 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.

[0048] Unless otherwise defined, all terms used herein, including technical and scientific terms, have the same meaning as commonly understood by those of ordinary skill in the art to which the concepts of the present disclosure belong. It will be further understood that the terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the relevant technical context and will not be interpreted in an idealized or overly formal sense unless so clearly defined in the present disclosure.

[0049] As used herein, the phrase "adjacent substituents are linked to each other to form a ring (or cyclic structure)" means that adjacent substituents can be combined with each other to form a substituted or unsubstituted alicyclic or aromatic ring. The phrase "adjacent substituents" of a certain substituent may refer to a substituent that replaces an atom directly connected to the atom substituted by the certain substituent, a substituent that is closest to the certain substituent in space, or a substituent that replaces an atom substituted by the certain substituent. For example, two substituents that replace the ortho position in a benzene ring structure and two substituents that replace the same carbon in an alicyclic ring can be interpreted as "adjacent substituents".

[0050] The structure and preparation examples of the organometallic compound according to the present disclosure and the organic light emitting diode including the same will be described below.

[0051] The organometallic compound according to the embodiment of the present disclosure can be represented by the following chemical formula I. Although not bound by theory, the inventors of the present disclosure have found that when a condensed ring structure (R) is introduced as in the following chemical formula I, the length of the main axis direction of the organometallic compound molecule increases to improve the horizontal orientation and give the organometallic compound molecule rigidity. Therefore, we have completed the present disclosure. When the organometallic compound represented by the following chemical formula I of the present disclosure is used as a dopant for the light-emitting layer, the full width at half maximum (FWHM) is reduced, thereby improving the color gamut, and improving the luminous efficiency and lifespan.

[0052]

[0053] Wherein in Chemical Formula I, M may represent one selected from the group consisting of Mo, W, Re, Ru, Os, Rh, Ir, Pd, Pt and Au;

[0054] R a represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino;

[0055] Each of X1 and X2 represents carbon;

[0056] X3 to X6 each independently represent a group selected from CR b and one of N;

[0057] Optionally, two R on two adjacent ones of X3 to X6 b may be connected to each other to form a cyclic structure, the cyclic structure comprising one selected from the group consisting of a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2-C20 heterocycloalkyl group, a substituted or unsubstituted C7-C20 aralkyl group, a substituted or unsubstituted C2-C20 heteroaralkyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group,

[0058] R b represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino;

[0059] (Z1-Z2) represents a bidentate ligand;

[0060] m is an integer selected from 1, 2 or 3, n is an integer selected from 0, 1 or 2, wherein the sum of m and n is the oxidation number of the metal M;

[0061] R represents a fused ring connected to X1 and X2, and comprises one selected from the group consisting of the following chemical formula II to chemical formula IV:

[0062]

[0063]

[0064]

[0065] Wherein in the chemical formula II to the chemical formula IV,

[0066] Y represents the selection of BR 19 , CR 19 R 20 、C=O、CNR 19 、SiR 19 R 20 NR 19 , PR 19 , AsR19 , SbR 19 、P(O)R 19 、P(S)R 19 、P(Se)R 19 、As(O)R 19 、As(S)R 19 、As(Se)R 19 、Sb(O)R 19 、Sb(S)R 19 、Sb(Se)R 19 , one of the group consisting of O, N, S, Se, Te, SO, SO2, SeO, SeO2, TeO, and TeO2;

[0067] R1 to R 18 each independently is one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino; and

[0068] R 19 and R 20 Each independently represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino.

[0069] When a metal complex of iridium (Ir) or platinum (Pt) having a large atomic number is used, phosphorescence can be effectively obtained even at room temperature. Therefore, in the organometallic compound according to the embodiment of the present disclosure, the central coordination metal (M) is preferably one of iridium (Ir) or platinum (Pt), for example, more preferably iridium (Ir). However, the present disclosure is not limited thereto.

[0070] The chemical formula I representing the organometallic compound according to the embodiment of the present disclosure may be based on the type of R (chemical formulas II to IV) and the orientation of Y, but the chemical formula I is one selected from the group consisting of the following chemical formulas II-1, II-2, III-1, III-2, IV-1, and IV-2:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] Wherein in each of Formula II-1, Formula II-2, Formula III-1, Formula III-2, Formula IV-1, and Formula IV-2, Y, X3 to X6, R a , R b , R1 to R 18 , (Z1-Z2), m and n are the same as defined herein for Formula I.

[0078] In an embodiment, R a is one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C6-C10 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, and phosphine;

[0079] X3 to X6 are each independently selected from CR b and one of N;

[0080] Optionally, two R on two adjacent ones of X3 to X6 b are connected to each other to form a cyclic structure, the cyclic structure comprising one selected from the group consisting of a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C7-C10 aralkyl group, a substituted or unsubstituted C2-C10 heteroaralkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C6-C10 aryl group, and a substituted or unsubstituted C3-C10 heteroaryl group,

[0081] R b represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 heteroalkyl, substituted or unsubstituted C7-C12 aralkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C2-C12 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C12 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfonyl, and phosphino;

[0082] (Z1-Z2) represents a bidentate ligand;

[0083] m is an integer selected from 1, 2 or 3, n is an integer selected from 0, 1 or 2, wherein the sum of m and n is the oxidation number of the metal M;

[0084] Y is selected from CR 19 R 20 NR 19 One of the group consisting of , O, S, SO, and SO2;

[0085] R1 to R 18 each independently represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C20 aralkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silicon, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino; and

[0086] R 19 and R 20 Each is independently selected from the group consisting of hydrogen, deuterium, hydroxyl, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 heteroalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C2-C12 heteroalkenyl, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C3-C12 heteroaryl.

[0087] In the organometallic compound according to the embodiment of the present disclosure, the auxiliary ligand combined with the central coordination metal can be a bidentate ligand. The bidentate ligand can contain an electron donor, thereby increasing the amount of MLCT (metal to ligand charge transfer), so that the organic light emitting diode exhibits improved luminescent properties, such as high luminous efficiency and high external quantum efficiency.

[0088] The organometallic compound according to the implementation of the present disclosure may have a heteroleptic structure or a homoleptic structure. For example, the organometallic compound according to the embodiment of the present disclosure may have a heteroleptic structure in which m is 1 and n is 2 in Chemical Formula I; or a heteroleptic structure in which m is 2 and n is 1; or a homoleptic structure in which m is 3 and n is 0.

[0089] 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 543. However, as long as the definition of the above Chemical Formula I is met, the specific examples of the compound represented by Chemical Formula I of the present disclosure are not limited thereto:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] According to one embodiment of the present disclosure, the organometallic compound represented by Chemical Formula I of the present disclosure may be used as a red phosphorescent material or a green phosphorescent material, preferably, as a red phosphorescent material.

[0118] Reference 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 host material 160' and a dopant 160". The dopant 160" may be made of an organic metal 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 emission 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 may be formed thereon.

[0119] Further, in Figure 1In the embodiment of the present invention, a hole transport auxiliary layer may be further added between the hole transport layer 150 and the light emitting layer 160. The hole transport auxiliary layer may contain a compound having good hole transport properties, and the difference between the HOMO energy levels of the hole transport layer 150 and the light emitting layer 160 may be reduced, thereby adjusting the hole injection properties. Therefore, the hole accumulation on the interface between the hole transport auxiliary layer and the light emitting layer 160 may be reduced, thereby reducing the quenching phenomenon in which the exciton disappears due to the polaron on the interface. Therefore, the degradation of the element may be reduced, and the element may be stabilized, thereby improving its efficiency and lifespan.

[0120] The first electrode 110 may serve as a positive electrode, 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.

[0121] The second electrode 120 may serve as a negative electrode, and may include Al, Mg, Ca, or Ag, which is a conductive material having a relatively small work function value, or an alloy or combination thereof. However, the present disclosure is not limited thereto.

[0122] 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 interface characteristics between the first electrode 110 and the hole transport layer 150, and may be selected from a material having appropriate conductivity. The hole injection layer 140 may include one or more compounds selected from the group consisting of MTDATA, CuPc, TCTA, HATCN, TDAPB, PEDOT / PSS, and N1, N1'-([1, 1'-biphenyl]-4, 4'-diyl)bis(N1, N4, N4)-triphenylbenzene-1, 4-diamine). Preferably, the hole injection layer 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.

[0123] The hole transport layer 150 may be adjacent to the light emitting layer and located 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, NPB, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl)-4-amine, etc. Preferably, the material of the hole transport layer 150 may include NPB. However, the present disclosure is not limited thereto.

[0124] According to the present disclosure, in order to improve the luminous efficiency of the diode 100, the light-emitting layer 160 can be formed by doping the main material 160' with an organic metal compound represented by Chemical Formula I as a dopant 160". The dopant 160" can be used as a green or red light-emitting material, preferably as a red phosphorescent material.

[0125] The doping concentration of the dopant 160 ″ according to the present disclosure may be adjusted to be in the range of 1 to 30 wt % 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 wt %, for example, 3 to 15 wt %, for example, 5 to 10 wt %, for example, 3 to 8 wt %, for example, 2 to 6 wt %, for example, 2 to 5 wt %, or for example, 2 to 3 wt %.

[0126] The light-emitting layer 160 according to the present disclosure includes a host material 160' known in the art that can achieve the effects of the present disclosure, and the layer 160 includes an organic metal compound represented by Chemical Formula I as a dopant 160". For example, according to the present disclosure, the host material 160' may include a compound containing a carbazole group, and may preferably include a host material selected from the group consisting of CBP (carbazole biphenyl), mCP (1,3-bis (carbazole-9-yl), etc. However, the present disclosure is not limited thereto.

[0127] Further, 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 high electron mobility so that electrons can be stably supplied to the light emitting layer under smooth electron transport.

[0128] For example, the material of the electron transport layer 170 may include a compound selected from the group consisting of: Alq3 (tris(8-hydroxyquinoline)aluminum), Liq (8-hydroxyquinoline lithium), PBD (2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxazole), TAZ (3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), spiro-PBD, BAlq (bis(2-methyl-8-hydroxyquinoline)-4-(phenylphenol)aluminum), SAlq, TPBi (2,2',2-(1,3,5-benzoyl)-tri(1-phenyl-1-H-benzimidazole), oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole and 2-(4-(9,10-di(naphthalene-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(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole. However, the present disclosure is not limited thereto.

[0129] The electron injection layer 180 is used to promote electron injection, and the material of the electron injection layer may include a compound selected from the group consisting of Alq3 (tris (8-hydroxyquinoline) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq, etc. However, the present disclosure is not limited to this. In addition, the electron injection layer 180 may be made of a metal compound. For example, the metal compound may include 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 to this.

[0130] The organic light emitting diode according to the present disclosure may be embodied as a white light emitting diode having a series structure. The series organic light emitting diode according to the illustrative embodiment of the present disclosure may be formed into a structure in which two or more adjacent light emitting stacks are connected to each other through a charge generation layer (CGL). The organic light emitting diode may include at least two light emitting stacks disposed on a substrate, wherein each of the at least two light emitting stacks includes first and second electrodes facing each other, and a light emitting layer disposed between the first and second electrodes to emit light of a specific wavelength band. Multiple light emitting stacks may emit light of the same color or different colors. In addition, one or more light emitting layers may be included in one light emitting stack, and the multiple light emitting layers may emit light of the same color or different colors.

[0131] In this case, the light emitting layer included in at least one of the plurality of light emitting stacks may include the organic metal compound represented by Chemical Formula I according to the present disclosure as a dopant. Adjacent ones of the plurality of light emitting stacks in the series structure may be connected to each other through a charge generation layer CGL including an N-type charge generation layer and a P-type charge generation layer.

[0132] Figure 2 and Figure 3 are cross-sectional views schematically illustrating an organic light emitting diode in a series structure having two light emitting stacks and an organic light emitting diode in a series structure having three light emitting stacks according to some embodiments of the present disclosure.

[0133] like 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 disposed 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 disposed between the first and second light emitting stacks ST1 and 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 organic metal compound represented by Chemical Formula I according to the present disclosure as a dopant. For example, as Figure 2 As 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 organic metal compound represented by Chemical Formula I doped therein. Figure 2 In the embodiment, each of the first and second light emitting stacks ST1 and ST2 may further include an additional light emitting layer in addition to each of the first light emitting layer 261 and the second light emitting layer 262 .

[0134] like Figure 3 As 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 and second light emitting stacks ST1 and ST2, and a second charge generation layer CGL2 located between the second and third light emitting stacks ST2 and 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 organic metal compound represented by Chemical Formula I according to the present disclosure as a dopant. For example, as Figure 3 As 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 organic metal compound represented by Chemical Formula I doped therein. Figure 3In the embodiment, each of the first, second, and third light emitting stacks ST1, ST2, and ST3 may further include an additional light emitting layer in addition to each of the first, second, and third light emitting layers 261, 262, and 263.

[0135] In addition, the 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 the first electrode and the second electrode.

[0136] The organic light emitting diode according to the present disclosure can be used as a light emitting element of each of an organic light emitting display device and a lighting device. In an embodiment, Figure 4 is a cross-sectional view schematically illustrating an organic light emitting display device including an organic light emitting diode according to some embodiments of the present disclosure.

[0137] like Figure 4 As shown, the organic light emitting display device 3000 includes a substrate 3010, an organic light emitting diode 4000, and a packaging 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.

[0138] exist Figure 4 In the present invention, gate lines and data lines intersecting each other to define pixel areas, power lines extending parallel to and spaced apart from one of the gate lines and the data lines, switching thin film transistors connected to the gate lines and the data lines, and storage capacitors connected to one electrode of the thin film transistor and the power line are further formed on the substrate 3010.

[0139] The driving thin film transistor Td is connected to the switching thin film transistor, and includes a semiconductor layer 3100 , a gate electrode 3300 , a source electrode 3520 , and a drain electrode 3540 .

[0140] 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 may be formed under the semiconductor layer 3100. The light shielding pattern may prevent light from being incident on the semiconductor layer 3100 to prevent the semiconductor layer 3100 from being deteriorated by light. In addition, the semiconductor layer 3100 may be made of polysilicon. In this case, both edges of the semiconductor layer 3100 may be doped with impurities.

[0141] A gate insulating layer 3200 made of an insulating material is formed on the entire surface of the substrate 3010 and on the semiconductor layer 3100. The gate insulating layer 3200 may be made of an inorganic insulating material, such as silicon oxide or silicon nitride.

[0142] The gate electrode 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 electrode 3300 is connected to the switching thin film transistor.

[0143] An interlayer insulating layer 3400 made of an insulating material is formed on the entire surface of the substrate 3010 and the gate electrode 3300. The interlayer insulating layer 3400 may 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.

[0144] The interlayer insulating layer 3400 has first and second semiconductor layer contact holes 3420 and 3440 respectively exposing two opposite sides of the semiconductor layer 3100 as defined herein. The first and second semiconductor layer contact holes 3420 and 3440 are respectively disposed on two opposite sides of the gate 3300 and spaced apart from the gate 3300.

[0145] A source electrode 3520 and a drain electrode 3540 made of a conductive material such as metal are formed on the interlayer insulating layer 3400. The source electrode 3520 and the drain electrode 3540 are disposed around the gate electrode 3300 and are spaced apart from each other and contact two opposite sides of the semiconductor layer 3100 through first and second semiconductor layer contact holes 3420 and 3440, respectively. The source electrode 3520 is connected to a power line.

[0146] The semiconductor layer 3100 , the gate electrode 3300 , the source electrode 3520 , and the drain electrode 3540 constitute a driving thin film transistor Td. The driving thin film transistor Td has a coplanar structure, in which the gate electrode 3300 , the source electrode 3520 , and the drain electrode 3540 are disposed on top of the semiconductor layer 3100 .

[0147] Alternatively, the driving thin film transistor Td may have an inverted staggered structure, in which the gate is disposed below the semiconductor layer, and the source and drain are disposed above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon. In one example, the switching thin film transistor may have a structure substantially the same as that of the driving thin film transistor (Td).

[0148] 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, red, green, and blue color filter patterns that absorb light may be formed separately 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 of a wavelength band corresponding to each color filter. The use of the color filter 3600 may enable the organic light-emitting display device 3000 to achieve full color.

[0149] 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, for example, on top of the second electrode 4200. For example, the color filter 3600 may be formed to have a thickness of 2 to 5 micrometers.

[0150] In one example, the planarization layer 3700 having the drain contact hole 3720 exposing the drain electrode 3540 of the driving thin film transistor Td as defined herein is formed to cover the driving thin film transistor Td.

[0151] On the planarization layer 3700 , each first electrode 4100 connected to the drain electrode 3540 of the driving thin film transistor Td through the drain contact hole 3720 is individually formed in each pixel region.

[0152] 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.

[0153] 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.

[0154] A bank layer 3800 covering the edge of the first electrode 4100 is formed on the planarization layer 3700. The bank layer 3800 exposes the center of the first electrode 4100 corresponding to the pixel area.

[0155] An organic layer 4300 is formed on the first electrode 4100. If necessary, the organic light emitting diode 4000 may have a series structure. Figures 2 to 4 and the above description thereof.

[0156] The second electrode 4200 is formed on the substrate 3010 on which the organic layer 4300 has been formed. The second electrode 4200 is arranged on the entire surface of the display area, and is made of a conductive material having a relatively small work function value, and can be used as a negative electrode (cathode). For example, the second electrode 4200 can be made of one of aluminum (Al), magnesium (Mg), and aluminum-magnesium alloy (Al-Mg).

[0157] The first electrode 4100 , the organic layer 4300 , and the second electrode 4200 constitute an organic light emitting diode 4000 .

[0158] An encapsulation film 3900 is formed on the second electrode 4200 to prevent external moisture from penetrating into the organic light emitting diode 4000. Figure 4 In the embodiment, 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.

[0159] Hereinafter, the preparation examples and embodiments of the present disclosure will be described. However, the following examples are only examples of the present disclosure. The present disclosure is not limited thereto.

[0160] Preparation Example

[0161] (1) Preparation of Compound 1

[0162]

[0163] Preparation of compound D1

[0164] M1 (9.78 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D1 (7.36 g, yield 60%).

[0165] Preparation of compound 1

[0166] D1 (7.36 g, 4.5 mmol), pentane-2,4-dione (4.51 g, 45 mmol), Na2CO3 (9.54 g, 90 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4. After filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound 1 (4.37 g, yield 55%) was obtained.

[0167] MS (m / z): 882.18

[0168] (2) Preparation of Compound 31

[0169]

[0170] Preparation of compound D31

[0171] M31 (12.82 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D31 (8.27 g, yield 55%).

[0172] Preparation of compound 31

[0173] D31 (8.27 g, 4.13 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (9.92 g, 41 mmol), Na2CO3 (8.74 g, 82.5 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 31 (4.98 g, yield 50%).

[0174] MS (m / z): 1206.46

[0175] (3) Preparation of Compound 50

[0176] (Step 1) Preparation of Compound A1

[0177]

[0178] Preparation of compound A1-1

[0179] In a reaction vessel, 5-bromo-4,6-dichloropyrimidine (25.6 g, 112.34 mmol), (1-methoxynaphthalene-2-yl)boric acid (24.97 g, 123.57 mmol), Pd(PPh3)4 (6.5 g, 5.62 mmol) and K2CO3 (31.05 g, 224.68 mmol) were dissolved in 1,4-dioxane (500 ml) and distilled water (100 ml), and the mixture was refluxed for 15 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. MgSO4 was added to the organic layer to remove the moisture therein, and then the solvent therein was removed by filtration under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound A1-1 (30.51 g, yield 89%) was obtained.

[0180] MS (m / z): 305.16

[0181] Preparation of Compound A1-2

[0182] A1-1 (30.51 g, 99.98 mmol) was dissolved in dichloromethane (450 ml) in a reaction vessel, and then BBr3 (23.7 ml, 249.95 mmol) was added dropwise thereto, and the mixture was stirred at room temperature for 3 hours. After adding distilled water to complete the reaction, the mixture was stirred at room temperature for 30 minutes, and then extracted with dichloromethane and distilled water. MgSO4 was added to the organic layer to remove the moisture therein, and then the solvent therein was removed by filtration under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound A1-2 (28.23 g, yield 97%).

[0183] MS (m / z): 291.13

[0184] Preparation of Compound A1

[0185] A1-2 (28.23 g, 96.98 mmol) and Cs2CO3 (47.40 g, 145.47 mmol) were dissolved in 300 ml of N, N-dimethylacetamide in a reaction vessel, and the mixture was refluxed for 16 hours. The reaction solution was cooled to room temperature, filtered through diatomaceous earth to remove inorganic matter therein, and the filtrate was concentrated. The mixture was dissolved in ethyl acetate, the mixed solution was filtered through silica gel, and then filtered under reduced pressure to remove the solvent therein. The obtained solid was converted into a slurry using n-hexane to obtain compound A1 (22.47 g, yield 91%) in the form of an ivory solid.

[0186] MS (m / z): 254.67

[0187] (Step 2) Preparation of Compound M50

[0188]

[0189] A1 (22.4 g, 87.96 mmol), 2-(4-(tert-butyl)naphthalene-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (30.02 g, 96.75 mmol), Pd(PPh3)4 (10.17 g, 8.80 mmol) and K2CO3 (24.31 g, 175.92 mmol) were dissolved in 1,4-dioxane (330 ml) and distilled water (66 ml), and the mixture was refluxed for 16 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. MgSO4 was added to the organic layer to remove moisture therein, and then the solvent therein was removed by filtration under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound M50 (25.84 g, yield 73%) was obtained.

[0190] MS (m / z): 402.49

[0191] (Step 3) Preparation of Compound 50

[0192]

[0193] Preparation of compound D50

[0194] M50 (25 g, 62.11 mmol), 2-ethoxyethanol 500 ml, and distilled water 167 ml were charged into a reaction vessel, and then nitrogen was bubbled for 1 hour, and IrCl3, H2O (9.95 g, 28.23 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D50 (16.3 g, yield 56%).

[0195] Preparation of compound 50

[0196] D50 (16.3 g, 7.91 mmol), 3,7-diethylnonyl-4,6-dione (5.88 g, 27.68 mmol), Na2CO3 (16.76 g, 158.16 mmol) and 300 ml of 2-ethoxyethanol were charged into a reaction vessel and refluxed in nitrogen for 24 hours. After the reaction was completed, dichloromethane was added to the reaction mixture, the reaction mixture was dissolved therein, and then extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtering, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound 50 (8.2 g, yield 43%) was obtained.

[0197] MS (m / z): 1206.50

[0198] (4) Preparation of Compound 57

[0199]

[0200] Preparation of compound D57

[0201] M57 (13.28 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D57 (7.42 g, yield 48%).

[0202] Preparation of compound 57

[0203] Under nitrogen stream, M57 (7.42 g, 3.6 mmol) and THF 200 ml were charged into the reaction vessel. Then, L57 (1.75 g, 7.9 mmol) dissolved in THF was slowly added thereto, and then stirred at room temperature overnight. After the reaction was completed, THF was removed under reduced pressure in a vacuum, and the mixture was extracted with toluene and filtered with diatomaceous earth. Toluene was removed under reduced pressure, and column chromatography was carried out with n-hexane and dichloromethane to obtain compound 57 (4.65 g, 55% yield).

[0204] MS (m / z): 1175.43

[0205] (5) Preparation of Compound 58

[0206]

[0207] Preparation of compound D58

[0208] M58 (15.13 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, and then nitrogen was bubbled for 1 hour, and then IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D58 (8.06 g, yield 47%).

[0209] Preparation of Compound 58

[0210] Under nitrogen flow, 2-bromopropane (1.73 g, 14.10 mmol) and 50 ml of THF were charged into a reaction vessel, the temperature was lowered to -78°C, and n-BuLi (5.8 ml, 2.5 M, n-hexane) was slowly added. After 30 minutes, N,N'-diisopropylcarbodiimide (1.78 g, 14.10 mmol) was slowly added while maintaining the temperature, and the mixture was stirred for 30 minutes. The reaction mixture was charged into a reaction vessel, D58 (8.06 g, 3.53 mmol) was dissolved in 200 ml of THF, and the reaction mixture was stirred at 80°C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed therefrom, and the reaction mixture was recrystallized with THF / pentane and dichloromethane / hexane solvents. Thus, compound 58 (4.41 g, yield 49%) was obtained.

[0211] MS (m / z): 1175.43

[0212] (6) Preparation of Compound 74

[0213]

[0214] Preparation of compound D74

[0215] M74 (12.82 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D74 (7.82 g, yield 52%).

[0216] Preparation of Compound 74

[0217] D74 (7.82 g, 3.9 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (9.37 g, 39 mmol), Na2CO3 (8.27 g, 78 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 74 (4.23 g, yield 45%).

[0218] MS (m / z): 1206.46

[0219] (7) Preparation of Compound 86

[0220]

[0221] Preparation of compound D86

[0222] M86 (12.82 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D86 (6.02 g, yield 40%).

[0223] Preparation of Compound 86

[0224] D86 (6.02 g, 3.0 mmol), 3,7-diethylnonyl-4,6-dione (6.37 g, 30 mmol), Na2CO3 (6.36 g, 60 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 86 (2.97 g, yield 42%).

[0225] MS (m / z): 1178.43

[0226] (8) Preparation of Compound 102

[0227]

[0228] Preparation of compound D102

[0229] M102 (10.70 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D102 (8.13 g, yield 62%).

[0230] Preparation of Compound 102

[0231] D102 (8.13 g, 4.65 mmol), pentane-2,4-dione (4.66 g, 46.5 mmol), Na2CO3 (9.86 g, 93 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture, the reaction mixture was dissolved therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound 102 (4.62 g, yield 53%) was obtained.

[0232] MS (m / z): 938.24

[0233] (9) Preparation of Compound 124

[0234]

[0235] Preparation of compound D124

[0236] M124 (11.70 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D124 (7.15 g, yield 51%).

[0237] Preparation of Compound 124

[0238] D124 (7.15 g, 3.83 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (7.05 g, 38.3 mmol), Na2CO3 (8.11 g, 77 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was dissolved therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 124 (4.06 g, yield 49%).

[0239] MS (m / z): 1082.32

[0240] (10) Preparation of Compound 148

[0241]

[0242] Preparation of compound D148

[0243] M148 (12.42 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D148 (5.58 g, yield 38%).

[0244] Preparation of Compound 148

[0245] D148 (5.58 g, 2.85 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (6.85 g, 28.5 mmol), Na2CO3 (6.04 g, 57 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 148 (2.70 g, yield 40%).

[0246] MS (m / z): 1182.36

[0247] (11) Preparation of Compound 170

[0248]

[0249] Preparation of compound D170

[0250] M170 (13.81 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, IrCl3, H2O (5.29 g, 15 mmol) were added thereto, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D170 (8.77 g, yield 55%).

[0251] Preparation of Compound 170

[0252] D170 (8.77 g, 4.13 mmol), 3,7-diethylnonyl-4,6-dione (8.76 g, 41.3 mmol), Na2CO3 (8.74 g, 83 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound 170 (4.90 g, yield 48%) was obtained.

[0253] MS (m / z): 1238.42

[0254] (12) Preparation of Compound 177

[0255]

[0256] Preparation of compound D177

[0257] M177 (13.81 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D177 (7.17 g, yield 45%).

[0258] Preparation of Compound 177

[0259] Under nitrogen flow, M177 (7.17 g, 3.4 mmol) and THF 200 ml were charged into a reaction vessel, and L177 (1.64 g, 7.4 mmol) dissolved in THF was slowly added thereto, followed by stirring at room temperature overnight. After the reaction was completed, THF was removed under reduced pressure in a vacuum, the mixture was extracted with toluene, and filtered with diatomaceous earth. Toluene was removed under reduced pressure, and column chromatography was performed with n-hexane and dichloromethane to obtain compound 177 (4.08 g, 50% yield).

[0260] MS(m / z):1207.39

[0261] (13) Preparation of Compound 178

[0262]

[0263] Preparation of compound D178

[0264] M178 (15.66 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D178 (7.58 g, yield 43%).

[0265] Preparation of Compound 178

[0266] Under nitrogen flow, 2-bromopropane (1.59 g, 12.90 mmol) and 50 ml of THF were charged into a reaction vessel, the temperature was lowered to -78 °C, and n-BuLi (5.3 ml, 2.5 M, n-hexane) was slowly added. After 30 minutes, N, N'-diisopropylcarbodiimide (1.63 g, 12.90 mmol) was slowly added while maintaining the temperature, and the mixture was stirred for 30 minutes. The reaction mixture was charged into a reaction vessel, D178 (7.58 g, 3.23 mmol) was dissolved in 200 ml of THF, and the mixture was stirred at 80 °C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed therefrom, and the mixture was recrystallized with THF / pentane and dichloromethane / hexane solvents. Thus, compound 178 (3.71 g, yield 44%) was obtained.

[0267] MS (m / z): 1308.54

[0268] (14) Preparation of Compound 190

[0269]

[0270] Preparation of compound D190

[0271] M190 (13.81 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D190 (9.09 g, yield 57%).

[0272] Preparation of Compound 190

[0273] D190 (9.09 g, 4.28 mmol), 3,7-diethylnonyl-4,6-dione (9.08 g, 42.8 mmol), Na2CO3 (9.06 g, 86 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 190 (4.87 g, yield 46%).

[0274] MS (m / z): 1238.42

[0275] (15) Preparation of Compound 216

[0276]

[0277] Preparation of compound D216

[0278] M216 (14.28 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D216 (6.38 g, yield 39%).

[0279] Preparation of Compound 216

[0280] D216 (6.38 g, 2.93 mmol), 3,7-diethyl-5-methylnonane-4,6-dione (6.62 g, 29.3 mmol), Na2CO3 (6.20 g, 59 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 216 (2.85 g, yield 38%).

[0281] MS (m / z): 1280.46

[0282] (16) Preparation of Compound 223

[0283]

[0284] Preparation of compound D223

[0285] M223 (12.16 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, IrCl3, H2O (5.29 g, 15 mmol) were added thereto, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D223 (8.66 g, yield 60%).

[0286] Preparation of Compound 223

[0287] D223 (8.66 g, 4.50 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (8.29 g, 45.0 mmol), Na2CO3 (9.54 g, 90 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 223 (5.10 g, yield 51%).

[0288] MS (m / z): 1110.36

[0289] (17) Preparation of Compound 241

[0290]

[0291] Preparation of compound D241

[0292] M241 (10.64 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D241 (6.27 g, yield 48%).

[0293] Preparation of Compound 241

[0294] D241 (6.27 g, 3.60 mmol), pentane-2,4-dione (3.60 g, 36.0 mmol), Na2CO3 (7.63 g, 72 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 241 (3.16 g, yield 47%).

[0295] MS (m / z): 934.29

[0296] (18) Preparation of Compound 271

[0297]

[0298] Preparation of compound D271

[0299] M271 (13.68 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D271 (8.07 g, yield 51%).

[0300] Preparation of Compound 271

[0301] D271 (8.07 g, 3.83 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (9.19 g, 38.3 mmol), Na2CO3 (8.11 g, 77 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 271 (4.14 g, yield 43%).

[0302] MS (m / z): 1258.57

[0303] (19) Preparation of Compound 290

[0304]

[0305] Preparation of compound D290

[0306] M290 (14.14 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D290 (8.45 g, yield 52%).

[0307] Preparation of Compound 290

[0308] D290 (8.45 g, 3.90 mmol), 3,7-diethylnonyl-4,6-dione (8.28 g, 39.0 mmol), Na2CO3 (8.27 g, 78 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 290 (4.42 g, yield 45%).

[0309] MS (m / z): 1258.57

[0310] (20) Preparation of Compound 298

[0311]

[0312] Preparation of compound D298

[0313] M298 (15.99 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D298 (7.35 g, yield 41%).

[0314] Preparation of Compound 298

[0315] Under nitrogen flow, 2-bromopropane (1.51 g, 12.30 mmol) and 50 ml of THF were charged into a reaction vessel, the temperature was lowered to -78°C, and n-BuLi (5.3 ml, 2.5 M, n-hexane) was slowly added. After 30 minutes, N, N'-diisopropylcarbodiimide (1.55 g, 12.30 mmol) was slowly added while maintaining the temperature, and the mixture was stirred for 30 minutes. The reaction mixture was charged into a reaction vessel, D298 (7.35 g, 3.08 mmol) was dissolved in 200 ml of THF, and the mixture was stirred at 80°C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed therefrom, and the mixture was then recrystallized with THF / pentane and dichloromethane / hexane solvents. Thus, compound 298 (3.27 g, yield 40%) was obtained.

[0316] MS (m / z): 1328.69

[0317] (21) Preparation of Compound 300

[0318]

[0319] Preparation of compound D300

[0320] M300 (15.07 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D300 (5.13 g, yield 30%).

[0321] Preparation of compound 300

[0322] Bromobenzene (1.41 g, 9.00 mmol) and 50 ml of THF were charged into a reaction vessel under a nitrogen stream, the temperature was reduced to -78 °C, and then n-butanol (3.7 ml, 2.5 M, n-hexane) was slowly added. After 30 minutes, N, N'-methyldicyclohexylamine (1.86 g, 9.00 mmol) was slowly added while maintaining the temperature, and the mixture was stirred for 30 minutes. The reaction mixture was charged into a reaction vessel, D300 (5.13 g, 2.25 mmol) was dissolved in 100 ml of THF, and then the mixture was stirred at 80 °C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed therefrom, and then the mixture was recrystallized with THF / pentane and dichloromethane / hexane solvents. Thus, compound 300 (2.18 g, yield 35%) was obtained.

[0323] MS (m / z): 1386.68

[0324] (22) Preparation of Compound 310

[0325]

[0326] Preparation of compound D310

[0327] M310 (14.14 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D310 (6.33 g, yield 39%).

[0328] Preparation of compound 310

[0329] D310 (6.33 g, 2.93 mmol), 3,7-diethylnonyl-4,6-dione (6.21 g, 29.3 mmol), Na2CO3 (6.20 g, 59 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours in a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 310 (2.72 g, yield 37%).

[0330] MS (m / z): 1258.57

[0331] (23) Preparation of Compound 330

[0332]

[0333] Preparation of compound D330

[0334] M330 (14.14 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D330 (6.50 g, yield 40%).

[0335] Preparation of compound 330

[0336] D330 (6.50 g, 3.00 mmol), 3,7-diethylnonyl-4,6-dione (6.37 g, 30.0 mmol), Na2CO3 (6.36 g, 60 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 330 (2.95 g, yield 39%).

[0337] MS (m / z): 1258.57

[0338] (24) Preparation of Compound 352

[0339]

[0340] Preparation of compound D352

[0341] M352 (14.14 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D352 (6.01 g, yield 37%).

[0342] Preparation of compound 352

[0343] D352 (6.01 g, 2.78 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (6.67 g, 27.8 mmol), Na2CO3 (5.88 g, 56 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture, the reaction mixture was dissolved therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 352 (2.50 g, yield 35%).

[0344] MS (m / z): 1286.60

[0345] (25) Preparation of Compound 363

[0346]

[0347] Preparation of compound D363

[0348] M363 (12.99 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D363 (5.32 g, yield 35%).

[0349] Preparation of compound 363

[0350] D363 (5.32 g, 2.63 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (4.84 g, 26.3 mmol), Na2CO3 (5.56 g, 53 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture, the reaction mixture was dissolved therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 363 (2.38 g, yield 39%).

[0351] MS (m / z): 1160.53

[0352] (26) Preparation of Compound 382

[0353]

[0354] Preparation of compound D382

[0355] M382 (11.13 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D382 (7.02 g, yield 52%).

[0356] Preparation of compound 382

[0357] D382 (7.02 g, 3.90 mmol), pentane-2,4-dione (3.90 g, 39.0 mmol), Na2CO3 (8.27 g, 78 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture, the reaction mixture was dissolved therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 382 (3.31 g, yield 44%).

[0358] MS (m / z): 964.31

[0359] (27) Preparation of Compound 410

[0360]

[0361] Preparation of compound D410

[0362] M410 (13.71 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D410 (7.13 g, yield 45%).

[0363] Preparation of Compound 410

[0364] D410 (7.13 g, 3.38 mmol), 3,7-diethylnonyl-4,6-dione (7.17 g, 33.8 mmol), Na2CO3 (7.15 g, 68 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture, the reaction mixture was dissolved therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound 410 (3.58 g, yield 43%) was obtained.

[0365] MS (m / z): 1232.53

[0366] (28) Preparation of Compound 417

[0367]

[0368] Preparation of compound D417

[0369] M417 (13.71 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D417 (6.50 g, yield 41%).

[0370] Preparation of Compound 417

[0371] Under nitrogen flow, M417 (6.50 g, 3.1 mmol) and THF 200 ml were charged into a reaction vessel, and L177 (1.49 g, 6.8 mmol) dissolved in THF was slowly added thereto, followed by stirring at room temperature overnight. After the reaction was completed, THF was removed under reduced pressure in a vacuum, the mixture was extracted with toluene, and filtered with diatomaceous earth. Toluene was removed under reduced pressure, and column chromatography was carried out with n-hexane and dichloromethane to obtain compound 417 (2.88 g, 39% yield).

[0372] MS (m / z): 1201.50 (29)

[0373] Preparation of Compound 418

[0374]

[0375] Preparation of compound D418

[0376] M418 (15.56 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D418 (6.84 g, yield 39%).

[0377] Preparation of Compound 418

[0378] Under the action of nitrogen gas flow, 2-bromopropane (1.44 g, 11.70 mmol) and 50 ml of THF were charged into the reaction vessel, the temperature was lowered to -78 ° C, and n-BuLi (4.80 ml, 2.5 M, n-hexane) was slowly added. After 30 minutes, N, N'-diisopropylcarbodiimide (1.48 g, 11.70 mmol) was slowly added while maintaining the temperature, and the mixture was stirred for 30 minutes. The reaction mixture was charged into the reaction vessel, D418 (6.84 g, 2.93 mmol) was dissolved in 200 ml of THF, and the mixture was stirred at 80 ° C for 8 hours. The temperature of the reaction mixture was lowered to room temperature, volatile substances were removed therefrom, and the mixture was then recrystallized with THF / pentane and dichloromethane / hexane solvents. Thus, compound 418 (2.90 g, yield 38%) was obtained.

[0379] MS (m / z): 1302.65

[0380] (30) Preparation of Compound 426

[0381]

[0382] Preparation of compound D426

[0383] M426 (13.71 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D426 (5.86 g, yield 37%).

[0384] Preparation of Compound 426

[0385] D426 (5.86 g, 2.28 mmol), 3,7-diethylnonyl-4,6-dione (5.89 g, 27.8 mmol), Na2CO3 (5.88 g, 56 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture, the reaction mixture was dissolved therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound 426 (2.39 g, yield 35%) was obtained.

[0386] MS (m / z): 1232.53

[0387] (31) Preparation of Compound 441

[0388]

[0389] (Step 1) Preparation of Compound A2

[0390] Preparation of compound A2-1

[0391] 4,6-dichloropyrimidine (25 g, 167.81 mmol), (3-nitronaphthalene-2-yl)boric acid (40.05 g, 184.59 mmol), Pd(PPh3)4 (9.7 g, 8.39 mmol) and K2CO3 (46.38 g, 335.62 mmol) were dissolved in a reaction vessel of 1,4-dioxane (500 ml) and distilled water (100 ml), and the mixture was refluxed for 15 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. MgSO4 was added to the organic layer to remove the moisture therein, and then the solvent therein was removed by filtration under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound A2-1 (36.43 g, yield 76%) was obtained.

[0392] MS (m / z): 285.69

[0393] Preparation of compound A2-2

[0394] A2-1 (36.43 g, 127.53 mmol) and PPh3 (83.62 g, 318.82 mmol) were dissolved in a reaction vessel of 1,2-dichlorobenzene (400 ml), and the mixture was refluxed for 15 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. MgSO4 was added to the organic layer to remove the moisture therein, and then the solvent therein was removed by filtration under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound A2-2 (22.32 g, yield 69%) was obtained.

[0395] MS (m / z): 253.69

[0396] Preparation of Compound A2

[0397] A2-2 (22.32 g, 87.98 mmol), iodobenzene (19.74 g, 94.78 mmol), CuI (15 g, 87.98 mmol), trans-1 2-cyclohexyldiamine (10.05 g, 87.98 mmol) and NaOH (7.04 g, 175.96 mmol) were dissolved in a reaction vessel of toluene (250 ml), and the mixture was refluxed for 16 hours. After the reaction solution was cooled to room temperature, the resulting solution was extracted with dichloromethane and distilled water. MgSO4 was added to the organic layer to remove the moisture therein, and then the solvent therein was removed by filtration under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane. Thus, compound A2 (25.2 g, yield 87%) was obtained in the form of an ivory solid.

[0398] MS (m / z): 329.78

[0399] (Step 2) Preparation of Compound M441

[0400]

[0401] A2 (25.2 g, 76.41 mmol), (3,5-dimethylphenyl) boronic acid (12.61 g, 84.05 mmol), Pd (PPh 3) 4 (8.83 g, 7.64 mmol) and K 2 CO 3 (21.12 g, 152.82 mmol) were dissolved in a reaction vessel of 1,4-dioxane (375 ml) and distilled water (75 ml), and the mixture was refluxed for 16 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. MgSO 4 was added to the organic layer to remove the moisture therein, and then the solvent therein was removed by filtration under reduced pressure. Column chromatography was performed with n-hexane and MC. Thus, compound M441 (22.28 g, yield 73%) was obtained.

[0402] MS (m / z): 399.49

[0403] (Step 3) Preparation of Compound 441

[0404]

[0405] Preparation of compound D441

[0406] M441 (13.18 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, and IrCl3, H2O (5.29 g, 15 mmol) were added, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D441 (5.07 g, yield 33%).

[0407] Preparation of Compound 441

[0408] D441 (5.07 g, 2.48 mmol), 1,3-dicyclohexyl-2-methylpropane-1,3-dione (6.20 g, 24.8 mmol), Na2CO3 (5.25 g, 50 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture, the reaction mixture was dissolved therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 441 (1.90 g, yield 31%).

[0409] MS (m / z): 1238.48

[0410] (32) Preparation of Compound 470

[0411]

[0412] Preparation of compound D470

[0413] M470 (13.71 g, 33 mmol), 200 ml of 2-ethoxyethanol and 66 ml of distilled water were charged into a reaction vessel, then nitrogen was bubbled for 1 hour, IrCl3, H2O (5.29 g, 15 mmol) were added thereto, and the mixture was refluxed for 24 hours. After the reaction was completed, the temperature was slowly lowered to room temperature, and the obtained solid was filtered. The filtered solid was washed with methanol and dried to obtain compound D470 (6.34 g, yield 40%).

[0414] Preparation of Compound 470

[0415] D470 (6.34 g, 3.00 mmol), 3,7-diethylnonyl-4,6-dione (6.37 g, 30.0 mmol), Na2CO3 (6.36 g, 60 mmol) and 200 ml of 2-ethoxyethanol were charged into a reaction vessel, and the mixture was refluxed for 24 hours under a nitrogen atmosphere. After the reaction was completed, dichloromethane was added to the reaction mixture to dissolve the reaction mixture therein, and then the resulting solution was extracted with dichloromethane and distilled water. The water in the organic layer was removed with MgSO4, and after filtration, the solvent was removed under reduced pressure. Column chromatography was performed with n-hexane and dichloromethane to obtain compound 470 (2.88 g, yield 39%).

[0416] MS (m / z): 1232.53

[0417] Example

[0418] <Example 1>

[0419] Clean the coating with a thickness of A glass substrate with an ITO (indium tin oxide) film is then ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol. Then, the glass substrate is dried. Thus, an ITO transparent electrode is formed. 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 60nm 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 80nm is formed. Then, CBP as the main 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 main material at a doping concentration of 5%. Thus, a light-emitting layer with a thickness of 30nm is formed. ET-1:Liq (1:1) (30nm) as a material for an electron transport layer and an electron injection layer is deposited on the light-emitting layer. Then, 100 nanometers thick aluminum is deposited thereon to form a negative electrode. In this way, an organic light-emitting diode is manufactured.

[0420]

[0421] HI-1 means N1,N1′-([1,1′-biphenyl]-4,4′-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine).

[0422] ET-1 means 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole.

[0423] <Examples 2 to 32 and Comparative Example 1>

[0424] Organic light emitting diodes of Examples 2 to 32 and Comparative Example 1 were manufactured in the same manner as in Example 1, except that compounds shown in the following Tables 1 to 3 were used instead of Compound 1 as a dopant in Example 1.

[0425] <Performance Evaluation of Organic Light Emitting Diodes>

[0426] Regarding the organic light emitting diodes prepared according to Examples 1 to 95 and Comparative Example 1, the 2 The operating voltage and efficiency characteristics at current, as well as at 20 mA / cm 2 Therefore, the operating voltage (V), EQE (%), and LT95 (%) were measured and converted into values ​​relative to the values ​​of Comparative Example 1, and the results are shown in Tables 1 to 8 below. LT95 refers to a lifetime evaluation scheme and means the time required for an organic light emitting diode to lose 5% of its initial brightness.

[0427] Table 1

[0428]

[0429]

[0430] The structure of the dopant material RD of Comparative Example 1 in Table 1 is as follows.

[0431]

[0432] Table 2

[0433]

[0434]

[0435] Table 3

[0436]

[0437] Table 4

[0438]

[0439]

[0440] Table 5

[0441]

[0442] Table 6

[0443]

[0444]

[0445] Table 7

[0446]

[0447] Table 8

[0448]

[0449]

[0450] It can be seen from the results of Tables 1 to 8 above that in the organic light-emitting diodes in which the organic metal compounds of Examples 1 to 95 of the present disclosure are used as dopants for the light-emitting layer of the organic light-emitting diodes, the operating voltage of the diodes is reduced compared with those in Comparative Example 1, and the external quantum efficiency (EQE) and lifetime (LT95) of the diodes are improved.

[0451] The scope of protection of the present disclosure should be interpreted by the scope of the claims, and all technical concepts within the scope equivalent thereto should be interpreted as included within the scope of the present disclosure. 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. The present disclosure can be implemented in various modified ways without departing from the scope of the technical concept of the present disclosure. Therefore, the embodiments of the present disclosure are not intended to limit the technical concept of the present disclosure, but are intended to describe the present disclosure. The scope of the technical concept of the present disclosure is not limited by the embodiments. Therefore, it should be understood that the above-mentioned embodiments are illustrative and non-restrictive in all aspects. The scope of protection of the present disclosure should be interpreted by the claims, and all technical concepts within the scope of the present disclosure should be interpreted as included within the scope of the present disclosure.

Claims

1. An organometallic compound represented by the following chemical formula:

2. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer, wherein the light emitting layer comprises a dopant material, Wherein the dopant material comprises the organometallic compound according to claim 1. The organic light-emitting device according to claim 2 , wherein the light-emitting layer is a red light-emitting layer. The organic light-emitting device according to claim 2 , wherein the light-emitting layer further comprises a host material. 5 . The organic light-emitting device according to claim 2 , wherein the organic layer further comprises at least one selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.

6. The organic light-emitting device according to claim 5, wherein the hole injection layer comprises one or more 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.

7. An organic light-emitting device according to claim 5, wherein the hole transport layer includes one or more of TPD, NPB, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine.

8. An organic light-emitting device according to claim 5, wherein the electron transport layer comprises one or more of Alq3, Liq, PBD, TAZ, spiro-PBD, BAlq, SAlq, TPBi, and 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole. 9 . The organic light-emitting device according to claim 5 , wherein the electron injection layer comprises one or more of Alq 3 , PBD, TAZ, spiro-PBD, BAlq, and SAlq.

10. An organic light-emitting device, comprising: A first electrode and a second electrode facing each other; as well as 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 comprises 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 comprises a dopant material, Wherein the dopant material comprises the organometallic compound according to claim 1.

11. An organic light-emitting device, comprising: a first electrode and a second electrode facing each other; as well as 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 comprises a dopant material, Wherein the dopant material comprises the organometallic compound according to claim 1.

12. An organic light emitting display device, comprising: substrate; a driving element located on the substrate; as well as An organic light emitting element disposed on the substrate and connected to the driving element, The organic light-emitting element comprises the organic light-emitting device according to claim 2.

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