Organometallic compound and organic electroluminescent device comprising the same

Abstract

An organometallic compound represented by the following chemical formula 1 is disclosed. When said organometallic compound is used as a dopant in the light-emitting layer of an organic electroluminescent device, the organometallic compound molecules are given rigidity, resulting in a narrow full width at half maximum (FWHM), thus improving color purity. Furthermore, non-luminescent recombination processes are reduced, thereby improving the luminous efficiency and lifetime of the organic electroluminescent device. Chemical formula 1 is shown below:

Description

Technical Field

[0001] This disclosure relates to organometallic compounds, and more specifically, to organometallic compounds having phosphorescent properties and organic electroluminescent devices comprising such organometallic compounds. Background Technology

[0002] Display devices are important in many fields, and there is a continuous need for improved performance. One example of such display devices is organic light-emitting display devices, such as organic light-emitting diodes: OLED displays.

[0003] In organic light-emitting diodes (OLEDs), when charge is injected into the light-emitting layer formed between the positive and negative electrodes, electrons and holes recombine to form excitons, thus converting their energy into light. This is how OLEDs emit light. Compared to traditional display devices, OLEDs can operate at lower voltages, consume relatively less power, exhibit superior color, and can be used in various ways due to the application of flexible substrates. Furthermore, the size of OLEDs can be freely adjusted. Summary of the Invention

[0004] Compared to liquid crystal displays (LCDs), the organic light-emitting diode (OLED) device according to the present invention has superior viewing angle and contrast, and is lightweight and ultra-thin because OLEDs do not require backlighting. The organic light-emitting diode includes multiple organic layers between a negative electrode (electron injection electrode; cathode) and a positive electrode (hole injection electrode; anode). The multiple organic layers may include a hole injection layer, a hole transport layer, a hole transport assist layer, an electron blocking layer, and light-emitting layers, electron transport layers, etc.

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

[0006] Organic materials used in organic electroluminescent devices can be mainly divided into luminescent materials and charge transport materials. Luminescent materials are a crucial factor determining the luminous efficiency of organic electroluminescent devices. They must possess high quantum efficiency, excellent electron and hole mobility, and exist uniformly and stably within the luminescent layer. Luminescent materials can be categorized based on the color of light emitted: blue, red, and green. Color-generating materials may include a host and dopants to improve color purity and luminous efficiency through energy transfer.

[0007] In organic light-emitting diodes (OLEDs), there is a continuous demand for low driving voltage, high efficiency, and long lifespan. Furthermore, there is an increasing need for luminescent materials capable of exhibiting high color purity covering a wide CIE color coordinate range. Particularly in white OLEDs using color filters, luminescent materials with excellent luminous efficiency and high color purity are required.

[0008] However, as color purity increases (CIE color coordinate X value increases), visibility decreases. Therefore, it is difficult to achieve high luminous efficiency with the same internal quantum efficiency. Thus, there is a need to develop a phosphorescent material that can achieve low driving voltage, high efficiency, long lifetime, and excellent color purity.

[0009] Therefore, the purpose of this disclosure is to provide an organometallic compound that enables high color purity and high brightness in an organic electroluminescent device, reduces the driving voltage of the organic electroluminescent device, and improves the luminous efficiency and lifetime of the organic electroluminescent device, and to provide an organic electroluminescent device in which the organic light-emitting layer contains the organometallic compound.

[0010] The purpose of this disclosure is not limited to the objectives described above. Other objectives and advantages not mentioned in this disclosure may be understood through the following description and may become clearer through implementation of this disclosure. Furthermore, it will be readily understood that the objectives and advantages of this disclosure can be achieved using the means set forth in the claims and combinations thereof.

[0011] To achieve the above objectives, this disclosure provides an organometallic compound having a novel structure represented by the following chemical formula 1 and an organic electroluminescent device in which the organometallic compound is contained as a dopant in the light-emitting layer.

[0012] Chemical formula

[0013]

[0014] In chemical formula 1,

[0015] M represents the central coordination metal and includes one selected from the group consisting of molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) and gold (Au);

[0016] Y is the same as or different from each other, and independently represents one of the following groups: BR1, CR1R2, C=O, C=NR1, SiR1R2, NR1, PR1, AsR1, SbR1, BiR1, P(O)R1, P(S)R1, P(Se)R1, As(O)R1, As(S)R1, As(Se)R1, Sb(O)R1, Sb(S)R1, Sb(Se)R1, Bi(O)R1, Bi(S)R1, Bi(Se)R1, Oxygen (O), Sulfur (S), Selenium (Se), Tellurium (Te), SO, SO2, SeO, SeO2, TeO, and TeO2;

[0017] X1 and X2 are different from each other, and X1 and X2 each independently represent one of the groups consisting of carbon (C), nitrogen (N), and phosphorus (P);

[0018] One of X1 and X2 is carbon (C), and the other of X1 and X2 is nitrogen (N) or phosphorus (P).

[0019] R1 and R2 each independently represent one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amido, 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 C1-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphinyl.

[0020] R a R b and R c Each of the following is independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amido, 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 C1-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphine.

[0021] It is a bidentate ligand;

[0022] m is an integer of 1, 2 or 3, n is an integer of 0, 1 or 2, and m+n is the oxidation number of metal M.

[0023] When organometallic compounds according to this disclosure are used as dopants in the light-emitting layer of an organic electroluminescent device, the driving voltage of the organic electroluminescent device can be reduced, and the luminous efficiency and lifetime characteristics of the organic electroluminescent device can be improved.

[0024] Furthermore, when organometallic compounds according to this disclosure are used as dopants in the luminescent layer of an organic electroluminescent device, the organometallic compound molecules can be made rigid, allowing for a narrower full width at half maximum (FWHM), thus improving color purity. In addition, non-luminescent recombination processes can be reduced, thereby improving the luminous efficiency and lifetime of the organic electroluminescent device.

[0025] The effects of this disclosure are not limited to those described above, and other effects not mentioned will be clearly understood by those skilled in the art through the following description. All components of each light-emitting display device according to all embodiments of this disclosure are operatively coupled and configured. Attached Figure Description

[0026] Figure 1 This is a schematic cross-sectional view of an organic electroluminescent device in which an organometallic compound according to some embodiments of the present disclosure is applied to the light-emitting layer.

[0027] Figure 2 This is a schematic cross-sectional view of an organic light-emitting display device that includes an organic electroluminescent device as an organic light-emitting element according to some embodiments of the present disclosure.

[0028] Figure 3 The graphs are plotted to show the emission wavelength and full width at half maximum (FWHM) of the organic electroluminescent devices of compound 232 of Example 12, which respectively apply the present disclosure, where the vertical axis represents the photoluminescence (PL) intensity and the horizontal axis represents the wavelength (nm).

[0029] Figure 4 This is a schematic cross-sectional view of an organic electroluminescent device having a tandem structure according to some embodiments of the present disclosure, the tandem structure having two light-emitting stacks and comprising an organometallic compound represented by chemical formula 1. Detailed Implementation

[0030] The advantages and features of this disclosure, as well as the methods for achieving these advantages and features, will become apparent from the embodiments described in detail below with reference to the accompanying drawings. However, this disclosure is not limited to the embodiments disclosed below, but can be implemented in various forms. Therefore, these embodiments are illustrated by way of example only and are not intended to be limiting.

[0031] The shapes, dimensions, ratios, angles, quantities, etc., disclosed in the accompanying drawings used to describe embodiments of this disclosure are exemplary, and this disclosure is not limited thereto. The same reference numerals refer to the same elements herein. Furthermore, for the sake of simplicity, descriptions and details of well-known steps and elements have been omitted. In addition, numerous specific details are set forth in the following detailed description of this disclosure to provide a thorough understanding of it. However, it should be understood that this disclosure can be practiced without these specific details. In other instances, well-known methods, processes, components, and circuits have not been described in detail so as not to unnecessarily obscure aspects of this disclosure.

[0032] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of this disclosure. As used herein, the singular constructs “a” and “an” are also intended to include the plural constructs, unless the context clearly indicates otherwise. It should also be understood that, when used in this specification, the terms “comprising,” “including,” “including,” and “comprising” specify the presence of the stated features, integers, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, integers, operations, elements, components, and / or portions thereof. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. When preceding a list of elements, expressions such as “at least one” may modify the entire list of elements and may not modify individual elements of the list. In the interpretation of numerical values, errors or tolerances may occur even if not explicitly described.

[0033] Furthermore, it should be understood that when a first element or layer is referred to as existing “on” a second element or layer, the first element may be directly disposed on the second element or may be indirectly disposed on the second element by a third element or layer disposed between the first and second elements or layers. It should be understood that when an element or layer is referred to as being “connected to” or “coupled to” another element or layer, it may be directly connected to or coupled to another element or layer, or one or more intermediate elements or layers may exist. Furthermore, it should be understood that when an element or layer is referred to as being “between” two elements or layers, it may be the only element or layer between the two elements or layers, or one or more intermediate elements or layers may also exist.

[0034] Furthermore, as used herein, when a layer, membrane, region, plate, etc., is disposed "on" or "on top" of another layer, membrane, region, plate, etc., the former can directly contact the latter, or another layer, membrane, region, plate, etc., can be disposed between the former and the latter. As used herein, when a layer, membrane, region, plate, etc., is directly disposed "on" or "on top" of another layer, membrane, region, plate, etc., the former directly contacts the latter, and no other layer, membrane, region, plate, etc., is disposed between the former and the latter. Furthermore, as used herein, when a layer, membrane, region, plate, etc., is disposed "below" or "under" another layer, membrane, region, plate, etc., the former can directly contact the latter, or another layer, membrane, region, plate, etc., can be disposed between the former and the latter. As used herein, when a layer, membrane, region, plate, etc., is directly disposed "below" or "under" another layer, membrane, region, plate, etc., the former directly contacts the latter, and no other layer, membrane, region, plate, etc., is disposed between the former and the latter.

[0035] In descriptions of temporal relationships, such as the temporal precedence between two events as "after," "following," or "before," unless it is specified that "immediately after," "immediately following," or "immediately before" is given, another event may occur between the two events.

[0036] It should be understood that although the terms “first,” “second,” “third,” etc., may be used herein to describe various elements, components, regions, layers, and / or parts, these elements, components, regions, layers, and / or parts should not be limited by these terms. These terms are used to distinguish one element, component, region, layer, or part from another, and the order or sequence is not limited. Therefore, without departing from the spirit and scope of this disclosure, the first element, component, region, layer, or part described below may be referred to as the second element, component, region, layer, or part.

[0037] The features of the various embodiments of this disclosure can be combined in whole or in part with each other, and can be technically related to or interoperable with each other. The embodiments can be implemented independently of each other, or they can be implemented together in a related relationship.

[0038] When interpreting numerical values, unless otherwise explicitly stated otherwise, the value is interpreted to include a range of error.

[0039] It should be understood that when a component or layer is referred to as being "connected to" or "coupled to" another component or layer, it can be directly connected to or coupled to another component or layer, or there may be one or more intermediate components or layers. Furthermore, it should be understood that when a component or layer is referred to as being "between" two components or layers, it can be the only component or layer between the two components or layers, or there may be one or more intermediate components or layers.

[0040] Unless otherwise defined, all terms used herein, including technical and scientific terms, shall have the same meaning as commonly understood by one of ordinary skill in the art to which the inventive concept pertains. It should also be understood that terms such as those defined in commonly used dictionaries should be interpreted as having the same meaning as their meaning in the context of the relevant field, and shall not be interpreted as having an idealized or overly formal meaning, unless expressly defined herein.

[0041] As used herein, the term "heterogeneous" refers to the substitution of one or more carbon atoms (e.g., 1 to 5 carbon atoms) that constitute an aromatic or alicyclic ring by one or more heteroatoms selected from the group consisting of N, O, S and combinations thereof.

[0042] The structure and preparation examples of organometallic compounds according to this disclosure, as well as organic electroluminescent devices including such organometallic compounds, will be described below.

[0043] An organometallic compound according to one embodiment of this disclosure can be represented by the following chemical formula 1, and can be used as a dopant in the luminescent layer to impart rigidity to the organometallic compound, thereby narrowing the full width at half maximum (FWHM) to improve color purity. In addition, luminous efficiency and lifetime can be improved.

[0044] Chemical Formula 1:

[0045]

[0046] In chemical formula 1,

[0047] M represents the central coordination metal and includes one selected from the group consisting of molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) and gold (Au);

[0048] Y is the same as or different from each other, and independently represents one of the following groups: BR1, CR1R2, C=O, C=NR1, SiR1R2, NR1, PR1, AsR1, SbR1, BiR1, P(O)R1, P(S)R1, P(Se)R1, As(O)R1, As(S)R1, As(Se)R1, Sb(O)R1, Sb(S)R1, Sb(Se)R1, Bi(O)R1, Bi(S)R1, Bi(Se)R1, Oxygen (O), Sulfur (S), Selenium (Se), Tellurium (Te), SO, SO2, SeO, SeO2, TeO, and TeO2;

[0049] X1 and X2 are different from each other, and X1 and X2 each independently represent one of the groups consisting of carbon (C), nitrogen (N), and phosphorus (P);

[0050] One of X1 and X2 is carbon (C), and the other of X1 and X2 is nitrogen (N) or phosphorus (P).

[0051] R1 and R2 each independently represent one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amido, 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 C1-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphinyl.

[0052] R a R b and R c Each of the following is independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amido, 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 C1-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphine.

[0053] It is a bidentate ligand;

[0054] m is an integer of 1, 2 or 3, n is an integer of 0, 1 or 2, and m+n is the oxidation number of metal M.

[0055] Based on the position of the major ligand bonded to the central coordinating metal, the organometallic compound represented by Formula 1, as an implementation of the present disclosure, can be represented by the structure of Formula 2 or Formula 3.

[0056] Chemical formula 2

[0057]

[0058] Chemical formula 3

[0059]

[0060] Among each of chemical formulas 2 to 3, X3, X4, X5, X6, X7, X8, X9, X 10 X 11 X 12 X 13 and X 14 They are the same or different from each other, and X3, X4, X5, X6, X7, X8, X9, X 10 X 11 X 12 X 13 and X 14 Each of these elements independently represents CR, nitrogen (N), phosphorus (P), sulfur (S), and oxygen (O); chosen from X3, X4, X5, X6, X7, X8, X9, X... 10 X 11 X 12 X 13 and X 14 The adjacent groups of the group combine with each other to form a C5 ring structure or a C6 ring structure;

[0061] R independently represents a group selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amido, 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 C1-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphinyl.

[0062] M, Y, X1, X2, R1, R2, Ra, Rb, Rc, The constraints on m and n are the same as those described above.

[0063] In one embodiment of the organometallic compound according to this disclosure, a bidentate ligand can be used as an auxiliary ligand to bond to a central coordinating metal. The bidentate ligand according to this disclosure may include an electron donor to increase the amount of metal-to-ligand charge transfer (MLCT), thereby improving the luminescence properties of the organic electroluminescent device, such as luminous efficiency and external quantum efficiency.

[0064] The structure of chemical formula 1, which exhibits auxiliary ligand properties as described above, can be represented by one of the groups consisting of chemical formulas 4 to 11.

[0065]

[0066]

[0067]

[0068] In each of chemical formulas 4 to 11,

[0069] X 15 X 16 X 17 X 18 X 19 X 20 X 21 X 22 X 23 X 24 X 25 X 26 and X 27 They are the same or different from each other, and X 15 X 16 X 17 X 18 X 19 X 20 X 21 X 22 X 23 X 24 X 25 X 26 and X 27 Each of these can be represented independently as CR, nitrogen (N), phosphorus (P), sulfur (S), and oxygen (O);

[0070] Choose Freedom X 15 X 16 X 17 X 18 X 19 X20 X 21 X 22 X 23 X 24 X 25 X 26 and X 27 The adjacent groups of the group combine with each other to form a C5 ring structure or a C6 ring structure;

[0071] Z3, Z4 and Z5 each independently represent one of the groups consisting of oxygen (O), sulfur (S) and NR7;

[0072] R3, R4, R5, R6, and R7 each independently represent one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidine, 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 C1-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heteroalkenyl, alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkoxy, amino, silyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, and phosphine.

[0073] Among them, M, Y, X1, X2, R1, R2, Ra, Rb, Rc, X3, X4, X5, X6, X7, X8, X9, 10 X 11 X 12 X 13 X 14 The constraints for m and n are the same as those described above.

[0074] Phosphorescence can be efficiently obtained at room temperature using iridium (Ir) or platinum (Pt) with a large atomic number. Therefore, in an organometallic compound according to one embodiment of the present disclosure, the central coordinating metal (M) is preferably iridium (Ir) or platinum (Pt), more preferably iridium (Ir). However, the present disclosure is not limited thereto.

[0075] In addition, in one embodiment of the organometallic compound according to this disclosure, Y in Formula 1 may be selected from the group consisting of oxygen (O), sulfur (S) and CR1R2.

[0076] Specific examples of compounds represented by Formula 1 of this disclosure may include one selected from the group consisting of compounds 1 to 466. However, this disclosure is not limited thereto, as long as the compound falls within the scope of Formula 1.

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100] According to one implementation of this disclosure, the organometallic compound represented by chemical formula 1 of this disclosure can be used as a red phosphorescent material or a green phosphorescent material.

[0101] Reference Figure 1 According to one implementation of this disclosure, an organic electroluminescent device can be provided, comprising: a first electrode 110; a second electrode 120 facing the first electrode 110; and an organic layer 130 disposed between the first electrode 110 and the second electrode 120. The organic layer 130 may include a light-emitting layer 160, and the light-emitting layer 160 may include an organometallic compound represented by chemical formula I. Furthermore, in the organic electroluminescent device, the organic layer 130 disposed between the first electrode 110 and the second electrode 120 can be formed by sequentially stacking a hole injection layer 140 (HIL), a hole transport layer 150 (HTL), a light-emitting layer 160 (EML), an electron transport layer 170 (ETL), and an electron injection layer 180 (EIL) on the first electrode 110. The second electrode 120 can be formed on the electron injection layer 180, and a protective layer can be formed on the second electrode 120.

[0102] The first electrode 110 can be used as a positive electrode and can be made of ITO, IZO, tin oxide, or zinc oxide, which are conductive materials with relatively large work function values. However, the present disclosure is not limited thereto.

[0103] The second electrode 120 can be used as a negative electrode and may include Al, Mg, Ca, Ag or combinations thereof, or alloys or combinations thereof, as conductive materials having relatively small work function values. However, the present disclosure is not limited thereto.

[0104] Hole injection layer 140 may be located between first electrode 110 and hole transport layer 150. The material of hole injection layer 140 may include compounds selected from the group consisting of: MTDATA, CuPc, TCTA, NPB (NPD), HATCN, TDAPB, PEDOT / PSS, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, NPNPB (N,N'-diphenyl-N,N'-bis[4-(N,N-diphenyl-amino)phenyl]benzidine), and preferably may include NPNPB. However, the present disclosure is not limited thereto.

[0105] The hole transport layer 150 may be located near the light-emitting layer and between the first electrode 110 and the light-emitting layer 160. The material of the hole transport layer 150 may include compounds selected from the group consisting of: TPD, NPD, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl)-4-amine, etc. However, this disclosure is not limited thereto.

[0106] According to this disclosure, the light-emitting layer 160 may include a host and an organometallic compound of Formula 1 as a dopant incorporated into the host to improve the luminous efficiency of the host and the organic electroluminescent device. The light-emitting layer 160 may be formed by adding about 1% to 30% by weight of the organometallic compound of Formula 1 of this disclosure to the host material, and may emit green or red light.

[0107] For example, the light-emitting layer 160 may include a host material, which includes one selected from the group consisting of CBP (carbazole biphenyl), mCP (1,3-bis(carbazole-9-yl)), etc. However, this disclosure is not limited thereto.

[0108] Electron transport layer 170 and electron injection layer 180 can be sequentially stacked between light-emitting layer 160 and second electrode 120. The material of 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.

[0109] For example, the material of electron transport layer 170 may include compounds selected from the group consisting of: Alq3 (tris(8-hydroxyquinoline)aluminum), Liq (lithium 8-hydroxyquinoline), PBD (2-(4-biphenyl))-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), TAZ (3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), spiro-PBD, BAlq (bis(2-methyl-8-quinoline acid)). (4-(phenylphenol)aluminum), SAlq, TPBi(2,2',2-(1,3,5-phenyltriyl)-tris(1-phenyl-1-H-benzimidazole), oxadiazole, triazole, phenanthrene, benzoxazole, benzothiazole, ZADN(2-[4-(9,10-di-2-naphthyl-2-anthracene-2-yl)phenyl]-1-phenyl-1H-benzimidazole, and preferably may include ZADN. However, the disclosure herein is not limited thereto.

[0110] The electron injection layer 180 is used to facilitate electron injection, and the material of the electron injection layer may include compounds selected from the group consisting of Alq3 (tris(8-hydroxyquinoline)aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq, etc. However, this disclosure is not limited thereto. Alternatively, the electron injection layer 180 may be made of a metal compound. 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, this disclosure is not limited thereto.

[0111] The organic electroluminescent device according to this disclosure can be used as an organic light-emitting element in each of organic light-emitting display devices and lighting devices. In one implementation... Figure 2 This is a schematic cross-sectional view of an organic light-emitting display device that includes an organic electroluminescent device as its organic light-emitting element according to some embodiments of the present disclosure.

[0112] like Figure 2 As shown, the organic light-emitting display device 3000 includes a substrate 3010, an organic electroluminescent element 4000, and an encapsulation film 3900 covering the organic electroluminescent element 4000. A driving thin-film transistor Td, which serves as a driving element, and the organic electroluminescent element 4000 connected to the driving thin-film transistor Td are located on the substrate 3010.

[0113] Optionally, gate lines and data lines that intersect each other to define pixel regions, power lines that extend parallel to and are spaced apart from one of the gate lines and data lines, switching thin-film transistors connected to the gate lines and data lines, and storage capacitors connected to an electrode of the thin-film transistors and the power lines are further formed on the substrate 3010.

[0114] The driving thin-film transistor Td is connected to the switching thin-film transistor and includes a semiconductor layer 3100, a gate 3300, a source 3520, and a drain 3540.

[0115] Semiconductor layer 3100 can be formed on substrate 3010 and can be made of oxide semiconductor material or polysilicon. When semiconductor layer 3100 is made of oxide semiconductor material, a light-shielding pattern can be formed below semiconductor layer 3100. The light-shielding pattern prevents light from entering semiconductor layer 3100, thereby preventing semiconductor layer 3010 from deteriorating due to light. Alternatively, semiconductor layer 3100 can be made of polysilicon. In this case, both edges of semiconductor layer 3100 can be doped with impurities.

[0116] A gate insulating layer 3200 made of 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.

[0117] A gate 3300, made of a conductive material such as metal, is formed on the gate insulating layer 3200 and corresponds to the center of the semiconductor layer 3100. The gate 3300 is connected to a switching thin-film transistor.

[0118] An interlayer insulating layer 3400 made of insulating material is formed on the entire surface of the substrate 3010 and on the gate 3300. The interlayer insulating layer 3400 may be made of inorganic insulating materials such as silicon oxide or silicon nitride, or organic insulating materials such as benzocyclobutene or optical acrylic.

[0119] The interlayer insulating layer 3400 has a first semiconductor layer contact hole 3420 and a second semiconductor layer contact hole 3440 defined therein to expose opposite sides of the semiconductor layer 3100, respectively. The first semiconductor layer contact hole 3420 and the second semiconductor layer contact hole 3440 are located on opposite sides of the gate 3300 and spaced apart from the gate 3300.

[0120] Source 3520 and drain 3540, made of a conductive material such as metal, are formed on the interlayer insulating layer 3400. Source 3520 and drain 3540 are located around the gate 3300 and spaced apart from each other, and each contacts opposite sides of the semiconductor layer 3100 through a first semiconductor layer contact hole 3420 and a second semiconductor layer contact hole 3440, respectively. Source 3520 is connected to a power supply line.

[0121] Semiconductor layer 3100, gate 3300, source 3520 and drain 3540 constitute driving thin film transistor Td. Driving thin film transistor Td has a coplanar structure, wherein gate 3300, source 3520 and drain 3540 are located on top of semiconductor layer 3100.

[0122] Alternatively, the driving thin-film transistor (Td) can have an anti-interleaved structure, where the gate is disposed below the semiconductor layer, while the source and drain are disposed above the semiconductor layer. In this case, the semiconductor layer can be made of amorphous silicon. In one example, the switching thin-film transistor can have substantially the same structure as the driving thin-film transistor (Td).

[0123] 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 can be formed separately in different pixel areas. Each of these color filter patterns may be configured to overlap with each organic layer 4300 of the organic electroluminescent element 4000 to emit light corresponding to the wavelength band of each color filter. Using the color filter 3600 enables the organic light-emitting display device 3000 to achieve full color.

[0124] For example, when the organic light-emitting display device 3000 is bottom-emitting, the light-absorbing color filter 3600 can be disposed on a portion of the interlayer insulating layer 3400 corresponding to the organic electroluminescent element 4000. In an alternative embodiment, when the organic light-emitting display device 3000 is top-emitting, the color filter can be disposed on the top of the organic electroluminescent element 4000, i.e., on the top of the second electrode 4200. For example, the color filter 3600 can be formed to have a thickness of 2-5 μm.

[0125] In one example, a protective layer 3700 is formed to cover the driving thin-film transistor Td, the protective layer 3700 having a drain contact hole 3720 defined therein for exposing the drain 3540 of the driving thin-film transistor Td.

[0126] On the protective layer 3700, each first electrode 4100 connected to the drain 3540 of the driving thin film transistor Td via a drain contact hole 3720 is formed in each pixel region.

[0127] The first electrode 4100 can be used as a positive electrode (anode) and can be made of a conductive material with a relatively large work function value. For example, the first electrode 410 can be made of a transparent conductive material such as ITO, IZO or ZnO.

[0128] In one example, when the organic light-emitting display device 3000 is a top-emitting type, a reflective electrode or reflective layer may be further formed below the first electrode 4100. For example, the reflective electrode or reflective layer may be made of one of aluminum (Al), silver (Ag), nickel (Ni), and aluminum-palladium-copper (APC) alloys.

[0129] A dam layer 3800 covering the edge of the first electrode 4100 is formed on the protective layer 3700. The dam layer 3800 exposes the center of the first electrode 4100 corresponding to the pixel region.

[0130] An organic layer 4300 is formed on the first electrode 4100. The organic electroluminescent element 4000 may have a series structure if needed.

[0131] The second electrode 4200 is formed on the substrate 3010 on which the organic layer 4300 has been formed. The second electrode 4200 is disposed on the entire surface of the display area and is made of a conductive material with a relatively small work function value, and the second electrode 4200 can be used as a cathode. For example, the second electrode 4200 can be made of one of aluminum (Al), magnesium (Mg) and aluminum-magnesium alloy (AlMg).

[0132] The first electrode 4100, the organic layer 4300, and the second electrode 4200 constitute an organic electroluminescent element 4000.

[0133] An encapsulation film 3900 is formed on the second electrode 4200 to prevent external moisture from penetrating into the organic electroluminescent element 4000. Optionally, the encapsulation film 3900 may have a three-layer structure in which a first inorganic layer, an organic layer, and an inorganic layer are stacked sequentially. However, the present disclosure is not limited thereto.

[0134] The organic electroluminescent device according to this disclosure can be used as a white light-emitting diode with a series structure. One implementation of the organic electroluminescent element with a series structure according to this disclosure may have a structure in which at least two unit light-emitting elements are connected to each other via a charge-generating layer (CGL). The organic electroluminescent element includes a first electrode and a second electrode facing each other and disposed on a substrate, and two or more light-emitting stacks arranged perpendicularly between the first electrode and the second electrode to emit light beams of specific wavelength bands, respectively. In this respect, the light-emitting layer may contain an organometallic compound represented by Chemical Formula 1 according to this disclosure as its dopant. Adjacent light-emitting stacks in the multiple light-emitting stacks in the series structure may be connected to each other via a charge-generating layer (CGL) including an N-type charge-generating layer and a P-type charge-generating layer.

[0135] Figure 4 This is a schematic cross-sectional view illustrating an implementation of the present disclosure of an organic electroluminescent element having two light-emitting stacks in a series structure. Figure 4 As shown, the organic electroluminescent element 100 according to this disclosure may include 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 includes: a first light-emitting stack (ST1) 240 located between the first electrode 110 and the second electrode 120 and including a first light-emitting layer 161; a second light-emitting stack (ST2) 250 located between the first light-emitting stack 240 and the second electrode 120 and including a second light-emitting layer 162; and a charge-generating layer (CGL) 260 disposed between the first light-emitting stack 240 and the second light-emitting stack 250. The charge-generating layer may include an N-type charge-generating layer 191 and a P-type charge-generating layer 192.

[0136] Furthermore, one implementation of the organic electroluminescent element according to this disclosure may have a series structure with three light-emitting stacks. Alternatively, four or more light-emitting stacks and three or more charge-generating layers may be disposed between the first electrode and the second electrode.

[0137] In the following description, examples of the synthesis of this disclosure and this embodiment will be described. However, the following embodiment is merely an example of this disclosure. This disclosure is not limited thereto.

[0138] Synthesis example

[0139] <Preparation of Compound A1>

[0140]

[0141] Step 1) Preparation of compound A1-2

[0142] Benzofuran-3-ylboronic acid (50 g, 308.73 mmol), 2-bromoaniline (53 g, 308.73 mmol), Pd(PPh3)4 (17.8 g, 15.43 mmol), and NaHCO3 (51 g, 617.46 mmol) were placed in a reaction vessel and dissolved in 500 mL toluene, 100 mL ethanol, and 100 mL H2O. The mixture was stirred at 100 °C for 6 hours. After the reaction was complete, the temperature was lowered to room temperature, and the solvent was removed by concentration under reduced pressure. The concentrated solution was dissolved in excess dichloromethane (MC) and then post-treated with MC / H2O. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was then purified using a column (MC / Hex = 1 / 1) to obtain compound A1-2 (42 g, 66% yield).

[0143] MS (m / z): 209.08

[0144] Step 2) Preparation of compound A1-1

[0145] Compound A1-2 (42 g, 200.72 mmol) was placed in a reaction vessel and dissolved in 500 mL of THF, followed by the addition of triethylamine (56 mL, 401.43 mmol). After cooling the reaction solution to 0 °C, ethyl chloroformate (19 mL, 200.72 mmol) was slowly added, and the mixture was stirred at room temperature for 3 hours. After the reaction was complete, the mixture was dissolved in excess ethyl acetate (EA) and then post-treated with EA / H2O. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was purified using a column (MC / Hex = 1 / 5) to obtain compound A1-1 (50 g, 89% yield).

[0146] MS(m / z): 281.11

[0147] Step 3) Preparation of compound A1

[0148] Compound A1-1 (50 g, 177.74 mmol) was placed in a reaction vessel, and the temperature was lowered to 0 °C. POCl3 (83 mL, 888.71 mmol) and triethylamine (25 mL, 177.74 mmol) were slowly added in this order. The reaction solution was stirred at room temperature for 30 minutes and then at 60 °C for 2 hours. After the reaction was complete, the temperature was lowered to 0 °C, and 3N NaOH (aq) was added for neutralization. The mixture was dissolved in excess MC for extraction. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was recrystallized to obtain compound A1 (25 g, 56% yield).

[0149] MS (m / z): 253.03

[0150] <Preparation of Compound A2>

[0151]

[0152] Step 1) Preparation of compound A2-2

[0153] Compound A2-2 (41.7 g, 60% yield) was obtained in the same manner as in the preparation of compound A1-2, except that benzo[b]thiophene-3-ylboronic acid (55 g, 308.73 mmol) was used instead of benzofuran-3-ylboronic acid (50 g, 308.73 mmol).

[0154] MS (m / z): 225.06

[0155] Step 2) Preparation of compound A2-1

[0156] Compound A2-1 (46.7 g, 85% yield) was prepared in the same manner as in the preparation of compound A1-1, except that A2-2 (41.7 g, 184.86 mmol) was used instead of benzofuran-3-ylboronic acid A1-2 (42 g, 200.72 mmol).

[0157] MS (m / z): 297.08

[0158] Step 3) Preparation of compound A2

[0159] Compound A2 (23.3 g, 55% yield) was obtained in the same manner as compound A1, except that A2-1 (46.7 g, 157.13 mmol) was used instead of A1-1 (50 g, 177.74 mmol).

[0160] MS (m / z): 269.01

[0161] <Preparation of Compound A3>

[0162]

[0163] Step 1) Preparation of compound A3-2

[0164] 4-Bromo-2-chloroquinoline (50 g, 206.18 mmol), 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol), Pd(PPh3)4 (12 g, 10.31 mmol), and K2CO3 (57 g, 412.36 mmol) were placed in a reaction vessel and dissolved in 600 mL of 1,4-dioxane and 100 mL of H2O. The mixture was stirred at 100 °C for 5 hours. After the reaction was complete, the temperature was lowered to room temperature, and the solvent was removed by concentration under reduced pressure. The concentrated solution was dissolved in excess MC and post-treated with MC / H2O. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was purified using a column (MC / Hex = 1 / 2) to obtain compound A3-2 (37 g, 63% yield).

[0165] MS (m / z): 284.04

[0166] Step 2) Preparation of compound A3-1

[0167] Compound A3-2 (37 g, 129.96 mmol) and PPh3 (68 g, 259.92 mmol) were placed in a reaction vessel and dissolved in 500 mL of DCB. The mixture was then stirred at 150 °C for 17 hours. After the reaction was complete, the temperature was lowered to room temperature, and the mixture was dissolved in excess MC, followed by MC / H2O post-treatment. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was purified using a column (MC / Hex = 2 / 1) to obtain compound A3-1 (24 g, 74% yield).

[0168] MS (m / z): 252.05

[0169] Step 3) Preparation of compound A3

[0170] Compound A3-1 (24 g, 94.97 mmol), iodobenzene (19.3 g, 94.97 mmol), CuI (18 g, 94.97 mmol), trans-1,2-diaminocyclohexane (10.8 g, 94.97 mmol), and K3PO4 (40 g, 189.94 mmol) were placed in a reaction vessel and dissolved in 500 mL of 1,4-dioxane. The mixture was then stirred at 100 °C for 6 hours. After the reaction was complete, the temperature was lowered to room temperature, and the insoluble inorganic salts were removed by filtration. The filtrate was dissolved in excess MC for extraction. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was purified using a column (MC / Hex = 1 / 3) to obtain compound A3 (26 g, 85% yield).

[0171] MS (m / z): 328.08

[0172] <Preparation of Compound A4>

[0173]

[0174] Step 1) Preparation of compound A4-2

[0175] Compound A4-2 (44 g, 68% yield) was obtained in the same manner as in the preparation of compound A3-2, except that ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxoborane-2-yl)benzoate (57 g, 206.18 mmol) was used instead of 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0176] MS (m / z): 311.07

[0177] Step 2) Preparation of compound A4-1

[0178] Compound A4-2 (44 g, 141.13 mmol) was placed in a reaction vessel and dissolved in 500 mL of diethyl ether. Then, 94 mL of MeMgBr 3M (in diethyl ether) (282.26 mmol) was slowly added. The reaction temperature was raised to 60 °C, and the mixture was stirred for 14 hours. After the reaction was complete, the temperature was lowered to 0 °C, and 100 mL of 5N NH4Cl (aq) was slowly added. The mixture was then dissolved in excess EA for extraction. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was purified using a column (MC / Hex = 1 / 1) to obtain compound A4-1 (24 g, 59% yield).

[0179] MS (m / z): 297.09

[0180] Step 3) Preparation of compound A4

[0181] Compound A4-1 (24 g, 80.59 mmol) was placed in a reaction vessel and dissolved in 300 mL of dichloromethane. BF3OEt2 (11 mL, 88.65 mmol) was slowly added, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, 30 mL of 3N NaHCO3 (aq) was added, followed by extraction with excess MC. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was purified using a column (MC / Hex = 1 / 3) to obtain compound A4 (20 g, 89% yield).

[0182] MS (m / z): 279.08

[0183] <Preparation of Compound A5>

[0184]

[0185] Step 1) Preparation of compound A5-2

[0186] Compound A5-2 (48.2 g, 66% yield) was obtained in the same manner as that used in the preparation of compound A3-2, except that ethyl 2-isopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoborane-1,3-yl)benzoate (65.6 g, 206.18 mmol) was used instead of 4,4,5,5-tetramethyl-1,3-(2-nitrophenyl)-2,2-dioxoborane (51 g, 206.18 mmol).

[0187] MS (m / z): 353.12

[0188] Step 2) Preparation of compound A5-1

[0189] Compound A5-1 (25.4 g, 55% yield) was prepared in the same manner as compound A4-1, except that A5-2 (48.2 g, 136.08 mmol) was used instead of benzofuran-3-ylboronic acid A4-2 (44 g, 141.13 mmol).

[0190] MS (m / z): 339.14

[0191] Step 3) Preparation of compound A5

[0192] Compound A5 (21.7 g, 90% yield) was obtained in the same manner as compound A4, except that A5-1 (25.4 g, 74.84 mmol) was used instead of A4-1 (24 g, 80.59 mmol).

[0193] MS (m / z): 321.13

[0194] <Preparation of Compound A6>

[0195]

[0196] Step 1) Preparation of compound A6-2

[0197] Compound A6-2 (40.7 g, 63% yield) was obtained in the same manner as in the preparation of compound A1-2, except that benzo[b]thiophene-3-ylboronic acid (50 g, 308.73 mmol) was used instead of benzofuran-3-ylboronic acid (50 g, 308.73 mmol).

[0198] MS (m / z): 209.08

[0199] Step 2) Preparation of compound A6-1

[0200] Compound A2-1 (47.1 g, 86% yield) was prepared in the same manner as in the preparation of compound A1-1, except that A6-2 (40.7 g, 194.50 mmol) was used instead of A1-2 (42 g, 200.72 mmol).

[0201] MS(m / z): 281.11

[0202] Step 3) Preparation of compound A6

[0203] Compound A6 (21.6 g, 51% yield) was obtained in the same manner as compound A1, except that A6-1 (47.1 g, 167.27 mmol) was used instead of A1-1 (50 g, 177.74 mmol).

[0204] MS (m / z): 253.03

[0205] <Preparation of Compound A7>

[0206]

[0207] Step 1) Preparation of compound A7-2

[0208] Compound A7-2 (36.3 g, yield 59%) was obtained in the same manner as in the preparation of compound A1-2, except that 7-isopropylbenzofuran-2-ylboronic acid (50 g, 245.06 mmol) was used instead of benzofuran-3-ylboronic acid (50 g, 308.73 mmol).

[0209] MS (m / z): 251.13

[0210] Step 2) Preparation of compound A7-1

[0211] Compound A7-1 (36.9 g, 79% yield) was prepared in the same manner as compound A1-1, except that A7-2 (36.3 g, 144.59 mmol) was used instead of A1-2 (42 g, 200.72 mmol).

[0212] MS (m / z): 323.15

[0213] Step 3) Preparation of compound A7

[0214] Compound A7 (19.4 g, 58% yield) was obtained in the same manner as compound A1, except that A7-1 (36.9 g, 114.22 mmol) was used instead of A1-1 (50 g, 177.74 mmol).

[0215] MS (m / z): 295.08

[0216] <Preparation of Compound A8>

[0217]

[0218] Step 1) Preparation of compound A8-2

[0219] Compound A8-2 (41.8 g, 66% yield) was obtained in the same manner as in the preparation of compound A1-2, except that benzo[b]thiophene-3-ylboronic acid (50 g, 308.73 mmol) was used instead of benzofuran-3-ylboronic acid (50 g, 308.73 mmol).

[0220] MS (m / z): 225.06

[0221] Step 2) Preparation of compound A8-1

[0222] Compound A8-1 (42.4 g, 77% yield) was prepared in the same manner as in the preparation of compound A1-1, except that A8-2 (41.8 g, 185.37 mmol) was used instead of A1-2 (42 g, 200.72 mmol).

[0223] MS (m / z): 297.08

[0224] Step 3) Preparation of compound A8

[0225] Compound A8 (21.2 g, 55% yield) was obtained in the same manner as compound A1, except that A8-1 (42.4 g, 142.74 mmol) was used instead of A1-1 (50 g, 177.74 mmol).

[0226] MS (m / z): 269.01

[0227] <Preparation of Compound A9>

[0228]

[0229] Step 1) Preparation of compound A9-2

[0230] Compound A9-2 (42.5 g, 70% yield) was obtained in the same manner as in the preparation of compound A1-2, except that 7-isopropylbenzo[b]thiophene-3-ylboronic acid (50 g, 227.17 mmol) was used instead of benzofuran-3-ylboronic acid (50 g, 308.73 mmol).

[0231] MS (m / z): 267.11

[0232] Step 2) Preparation of compound A9-1

[0233] Compound A9-1 (43.2 g, 80% yield) was prepared in the same manner as in the preparation of compound A1-1, except that A9-2 (42.5 g, 159.02 mmol) was used instead of benzofuran-3-ylboronic acid A1-2 (42 g, 200.72 mmol).

[0234] MS (m / z): 339.13

[0235] Step 3) Preparation of compound A9

[0236] Compound A9 (22.6 g, 57% yield) was obtained in the same manner as compound A1, except that A9-1 (43.2 g, 127.21 mmol) was used instead of A1-1 (50 g, 177.74 mmol).

[0237] MS (m / z): 311.05

[0238] <Preparation of Compound A10>

[0239]

[0240] Step 1) Preparation of compound A10-2

[0241] Compound A10-2 (39.1 g, yield 65%) was obtained in the same manner as in the preparation of compound A1-2, except that benzofuran-3-ylboronic acid (50 g, 308.73 mmol) was used instead of 7,7-isobutylbenzo[b]thiophene-3-ylboronic acid (50 g, 213.57 mmol).

[0242] MS (m / z): 281.12

[0243] Step 2) Preparation of compound A10-1

[0244] Compound A10-1 (36.8 g, 75% yield) was prepared in the same manner as in the preparation of compound A1-1, except that A10-2 (39.1 g, 138.82 mmol) was used instead of A1-2 (42 g, 200.72 mmol).

[0245] MS (m / z): 353.14

[0246] Step 3) Preparation of compound A10

[0247] Compound A10 (16.6 g, 49% yield) was obtained in the same manner as in the preparation of compound A1, except that A10-1 (36.8 g, 104.11 mmol) was used instead of A1-1 (50 g, 177.74 mmol).

[0248] MS (m / z): 325.07

[0249] <Preparation of Compound A11>

[0250]

[0251] Step 1) Preparation of compound A11-2

[0252] Compound A11-2 (48.9 g, 76% yield) was obtained in the same manner as compound A3-2, except that 3-bromo-2-chloroquinoline (50 g, 206.18 mmol) and ethyl 2-isopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxoborane-2-yl)benzoate (65.6 g, 206.18 mmol) were used instead of 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0253] MS (m / z): 311.07

[0254] Step 2) Preparation of compound A11-1

[0255] Compound A11-1 (21.0 g, 45% yield) was prepared in the same manner as compound A4-1, except that A11-2 (48.9 g, 156.70 mmol) was used instead of benzofuran-3-ylboronic acid A4-2 (44 g, 141.13 mmol).

[0256] MS (m / z): 297.09

[0257] Step 3) Preparation of compound A11

[0258] Compound A11 (16.2 g, 82% yield) was obtained in the same manner as compound A4, except that A11-1 (21.0 g, 70.52 mmol) was used instead of A4-1 (24 g, 80.59 mmol).

[0259] MS (m / z): 279.08

[0260] <Preparation of Compound A12>

[0261]

[0262] Step 1) Preparation of compound A12-2

[0263] Compound A12-2 (34.0 g, 58% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) was used instead of 3-bromo-2-chloroquinoline (50 g, 206.18 mmol).

[0264] MS (m / z): 284.04

[0265] Step 2) Preparation of compound A12-1

[0266] Compound A12-1 (22.7 g, 75% yield) was prepared in the same manner as compound A3-1, except that A12-2 (34.0 g, 119.59 mmol) was used instead of benzofuran-3-ylboronic acid A3-2 (37 g, 129.96 mmol).

[0267] MS (m / z): 252.05

[0268] Step 3) Preparation of compound A12

[0269] Compound A12 (11.4 g, 88% yield) was obtained in the same manner as in the preparation of compound A3, except that A12-1 (10 g, 39.57 mmol) was used instead of A3-1 (24 g, 94.97 mmol).

[0270] MS (m / z): 328.08

[0271] <Preparation of Compound A13>

[0272]

[0273] Compound A13 (9.1 g, 78% yield) was obtained in the same manner as in the preparation of compound A3, except that A3-1 (24 g, 94.97 mmol) and iodobenzene (19.3 g, 94.97 mmol) were replaced with A12-1 (10 g, 39.57 mmol) and 2-iodopropane (6.7 g, 39.57 mmol).

[0274] MS (m / z): 294.09

[0275] <Preparation of Compound B1>

[0276]

[0277] Compound B1 (8.8 g, 76% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxoborane (8.0 g, 39.42 mmol) were replaced with A1 (10 g, 39.42 mmol) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0278] MS (m / z): 295.10

[0279] <Preparation of Compound B2>

[0280]

[0281] Compound B2 (9.4 g, 74% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (9.2 g, 39.42 mmol) were replaced with A1 (10 g, 39.42 mmol) and 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0282] MS (m / z): 323.13

[0283] <Preparation of Compound B3>

[0284]

[0285] Compound B3 (12.2 g, 80% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A1 (10 g, 39.42 mmol) and 2-(4-isopropylnaphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (11.6 g, 39.42 mmol).

[0286] MS (m / z): 387.16

[0287] <Preparation of Compound B4>

[0288]

[0289] Compound B4 (12.3 g, 78% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A1 (10 g, 39.42 mmol) and 2-(4-tert-butylnaphthyl-2-yl)-4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0290] MS (m / z): 401.18

[0291] <Preparation of Compound B5>

[0292]

[0293] Compound B5 (10.9 g, 73% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-2-(1,6,8-trimethylnaphthyl-2-yl)-1,3,2-dioxoborane (11.0 g, 37.07 mmol) were replaced with A2 (10 g, 37.07 mmol) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0294] MS (m / z): 403.14

[0295] <Preparation of Compound B6>

[0296]

[0297] Compound B6 (11.1 g, 72% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A2 (10 g, 37.07 mmol) and 2-(4-isopropylnaphthyl-2-yl)-4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0298] <Preparation of Compound B7>

[0299]

[0300] Compound B7 (9.5 g, 84% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxoborane (6.2 g, 30.41 mmol) were replaced with A3 (10 g, 30.41 mmol) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0301] MS (m / z): 370.15

[0302] <Preparation of Compound B8>

[0303]

[0304] Compound B8 (10.2 g, 84% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (7.2 g, 31.07 mmol) were replaced with A5 (10 g, 31.07 mmol) and 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0305] MS (m / z): 391.23

[0306] <Preparation of Compound B9>

[0307]

[0308] Compound B9 (10.4 g, 82% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A1 (10 g, 35.74 mmol) and SM-1 (8.0 g, 35.74 mmol).

[0309] MS (m / z): 355.22

[0310] <Preparation of Compound B10>

[0311]

[0312] Compound B10 (9.7 g, 76% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (9.2 g, 39.42 mmol) were replaced with A6 (10 g, 39.42 mmol) and 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0313] MS (m / z): 323.13

[0314] <Preparation of Compound B11>

[0315]

[0316] Compound B11 (11.3 g, 80% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-2-(1-methylnaphthyl-2-yl)-1,3,2-dioxoborane (10.6 g, 39.42 mmol) were replaced with A6 (10 g, 39.42 mmol) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0317] MS (m / z): 359.13

[0318] <Preparation of Compound B12>

[0319]

[0320] Compound B12 (11.9 g, 78% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A6 (10 g, 39.42 mmol) and 2-(4-isopropylnaphthyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (11.7 g, 39.42 mmol).

[0321] MS (m / z): 387.16

[0322] <Preparation of Compound B13>

[0323]

[0324] Compound B13 (12.2 g, 77% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A6 (10 g, 39.42 mmol) and 2-(4-tert-butylnaphthyl-2-yl)-4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0325] MS (m / z): 401.18

[0326] <Preparation of Compound B14>

[0327]

[0328] Compound B14 (12.2 g, 72% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A7 (10 g, 33.81 mmol) and 2-(4-tert-butylnaphthyl-2-yl)-4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0329] MS (m / z): 443.22

[0330] <Preparation of Compound B15>

[0331]

[0332] Compound B15 (11.1 g, 88% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (8.6 g, 37.07 mmol) were replaced with A8 (10 g, 37.07 mmol) and 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0333] MS (m / z): 339.11

[0334] <Preparation of Compound B16>

[0335]

[0336] Compound B16 (11.1 g, 88% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (8.6 g, 37.07 mmol) were replaced with A8 (10 g, 37.07 mmol) and 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0337] MS (m / z): 339.11

[0338] <Preparation of Compound B17>

[0339]

[0340] Compound B17 (11.0 g, 76% yield) was obtained in the same manner as compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (9.5 g, 30.69 mmol) were replaced with A10 (10 g, 30.69 mmol) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0341] MS (m / z): 473.22

[0342] <Preparation of Compound B18>

[0343]

[0344] Compound B18 (10.8 g, 81% yield) was obtained in the same manner as in the preparation of compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-2-(naphthyl-2-yl)-1,3,2-dioxoborane (9.1 g, 35.74 mmol) were replaced with A11 (10 g, 35.74 mmol) and 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0345] MS (m / z): 371.17

[0346] <Preparation of Compound B19>

[0347]

[0348] Compound B19 (10.4 g, 72% yield) was obtained in the same manner as compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A12 (10 g, 30.41 mmol) and 2-(4-tert-butylnaphthyl-2-yl)-4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxoborane (51 g, 206.18 mmol).

[0349] MS (m / z): 476.23

[0350] <Preparation of Compound B20>

[0351]

[0352] Compound B20 (11.2 g, 77% yield) was obtained in the same manner as compound A3-2, except that 4-bromo-2-chloroquinoline (50 g, 206.18 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxoborane (51 g, 206.18 mmol) were replaced with A13 (10 g, 33.92 mmol) and 2-(6-isopropylnaphthyl-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxoborane (10.0 g, 33.92 mmol).

[0353] MS (m / z): 428.23

[0354] <Preparation of Compound 1>

[0355]

[0356] Step 1) Preparation of compound C1

[0357] B1 (5.5 g, 18.72 mmol), 80 mL of 1,4-dioxane, and 20 mL of H2O were introduced into a reaction vessel and bubbled with nitrogen for 1 hour. Then, IrCl3(H2O)X (3 g, 8.51 mmol) was added, and the mixture was stirred at 100 °C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and the resulting solid was filtered. The filtered solid was dried to obtain intermediate C1 (5.7 g, yield 38%).

[0358] Step 2) Preparation of Compound 1

[0359] C1 (5.7 g, 3.50 mmol), pentane-2,4-dione (3.5 g, 7.35 mmol), and Na2CO3 (7.5 g, 70.39 mmol) were added to a reaction vessel and dissolved in 100 mL of 1,4-dioxane. The mixture was stirred for 24 hours. After the reaction was complete, the mixture was dissolved in excess MC for extraction. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was recrystallized to obtain compound 1 (1.9 g, 61% yield).

[0360] MS (m / z): 880.19

[0361] <Preparation of Compound 4>

[0362] Intermediate C2 (5.6 g, 35% yield) was obtained in the same manner as compound C1, except that B3 (7.3 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 4 (1.8 g, 58% yield) was obtained in the same manner as compound 1, except that C2 (5.6 g, 2.98 mmol) was used instead of C1 (5.7 g, 3.50 mmol).

[0363] MS (m / z): 1038.3

[0364] <Preparation of Compound 24>

[0365] Compound 24 (0.7 g, 38% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (0.7 g, 3.89 mmol) were used instead of C1 (3 g, 1.85 mmol) and pentane-2,4-dione (0.7 g, 3.89 mmol).

[0366] MS (m / z): 949.31

[0367] <Preparation of Compound 36>

[0368] Intermediate C3 (6.8 g, 41% yield) was obtained in the same manner as in the preparation of compound C1, except that B4 (7.5 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 36 (2.2 g, 55% yield) was obtained in the same manner as in the preparation of compound 1, except that C3 (6.8 g, 3.49 mmol) and (E)-N,N'-diisopropylbenzamide (1.4 g, 6.98 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol).

[0369] MS (m / z): 1144.43

[0370] <Preparation of Compound 58>

[0371] Intermediate C4 (7.7 g, 52% yield) was obtained in the same manner as in the preparation of compound C1, except that B2 (6.1 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 58 (2.2 g, 55% yield) was obtained in the same manner as in the preparation of compound 1, except that C4 (7.7 g, 4.45 mmol) and pyridinecarboxylic acid (1.1 g, 9.34 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol).

[0372] MS (m / z): 959.23

[0373] <Preparation of Compound 88>

[0374] Intermediate C5 (7.8 g, 48% yield) was obtained in the same manner as in the preparation of compound C1, except that B5 (7.6 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 88 (1.8 g, 41% yield) was obtained in the same manner as in the preparation of compound 1, except that C5 (7.8 g, 4.08 mmol) was used instead of C1 (5.7 g, 3.50 mmol).

[0375] MS (m / z): 1081.25

[0376] <Preparation of Compound 127>

[0377] Intermediate C6 (7.6 g, 46% yield) was obtained in the same manner as in the preparation of compound C1, except that B5 (7.6 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 127 (1.8 g, 39% yield) was obtained in the same manner as in the preparation of compound 1, except that C6 (7.6 g, 3.91 mmol) and 2,4-dimethyl-6-phenylpyridine (1.5 g, 8.21 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol).

[0378] MS (m / z): 1166.32

[0379] <Preparation of Compound 129>

[0380] Intermediate C7 (5.2 g, 32% yield) was obtained in the same manner as in the preparation of compound C1, except that B7 (6.9 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 129 (1.6 g, 57% yield) was obtained in the same manner as in the preparation of compound 1, except that C7 (5.2 g, 2.72 mmol) was used instead of C1 (5.7 g, 3.50 mmol).

[0381] MS (m / z): 1030.20 <Preparation of Compound 163>

[0382] Intermediate C8 (7.0 g, 41% yield) was obtained in the same manner as in the preparation of compound C1, except that B8 (7.3 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 163 (2.1 g, 52% yield) was obtained in the same manner as in the preparation of compound 1, except that C4 (7.0 g, 3.49 mmol) and (Z)-1,3-dicyclopentyl-3-hydroxyprop-2-en-1-one (1.5 g, 7.32 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol).

[0383] MS (m / z): 1180.55

[0384] <Preparation of Compound 171>

[0385] Intermediate C9 (7.1 g, 45% yield) was obtained in the same manner as in the preparation of compound C1, except that B9 (6.5 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 171 (1.4 g, 37% yield) was obtained in the same manner as in the preparation of compound 1, except that C9 (7.1 g, 3.83 mmol) was used instead of C1 (5.7 g, 3.50 mmol).

[0386] MS (m / z): 975.23

[0387] <Preparation of Compound 220>

[0388] Intermediate C10 (6.6 g, 43% yield) was obtained in the same manner as in the preparation of compound C1, except that B11 (6.7 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 220 (1.5 g, 40% yield) was obtained in the same manner as in the preparation of compound 1, except that C10 (6.6 g, 3.66 mmol) was used instead of C1 (5.7 g, 3.50 mmol).

[0389] MS (m / z): 1008.25

[0390] <Preparation of Compound 232>

[0391] Intermediate C11 (8.9 g, 51% yield) was obtained in the same manner as in the preparation of compound C1, except that B13 (7.5 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 232 (1.9 g, 38% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were used instead of C1 (8.9 g, 4.34 mmol) and (Z)-3,7-diethyl-6-hydroxynon-5-en-4-one (1.9 g, 9.11 mmol).

[0392] MS (m / z): 1178.46

[0393] <Preparation of Compound 236>

[0394] Compound 236 (1.1 g, 38% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.0 g, 2.43 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were replaced by C1 (5.0 g, 2.43 mmol) and (E)-N,N'-((Z)-pent-2-en-2-yl-4-ylidene)dipropane-2-amine (0.9 g, 5.10 mmol).

[0395] MS (m / z): 1148.46

[0396] <Preparation of Compound 239>

[0397] Compound 239 (1.0 g, yield 35%) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.0 g, 2.43 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were replaced by C1 (5.0 g, 2.43 mmol) and (E)-N,N'-diisopropylbenzamide (1.0 g, 5.10 mmol).

[0398] MS (m / z): 1196.46

[0399] <Preparation of Compound 241>

[0400] Intermediate C12 (7.8 g, 42% yield) was obtained in the same manner as in the preparation of compound C1, except that B14 (8.3 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 241 (2.4 g, 52% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and (Z)-3,7-diethyl-6-hydroxy-3,7-dimethylnon-5-en-4-one (1.8 g, 8.21 mmol).

[0401] MS (m / z): 1290.58

[0402] <Preparation of Compound 264>

[0403] Intermediate C13 (8.0 g, 47% yield) was obtained in the same manner as in the preparation of compound C1, except that B12 (7.3 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 264 (1.8 g, 43% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were used instead of C1 (8.0 g, 3.99 mmol) and pyridinecarboxylic acid (1.0 g, 8.40 mmol).

[0404] MS (m / z): 1061.28

[0405] <Preparation of Compound 266>

[0406] Intermediate C14 (6.4 g, 43% yield) was obtained in the same manner as in the preparation of compound C1, except that B10 (6.1 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 266 (2.1 g, 56% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were used instead of C1 (6.4 g, 3.66 mmol) and (Z)-1,3-dicyclopentyl-3-hydroxyprop-2-en-1-one (1.6 g, 7.68 mmol).

[0407] MS (m / z): 1034.33

[0408] <Preparation of Compound 286>

[0409] Intermediate C15 (6.2 g, 40% yield) was obtained in the same manner as in the preparation of compound C1, except that B15 (6.4 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 286 (1.4 g, 43% yield) was obtained in the same manner as in the preparation of compound 1, except that C15 (6.2 g, 3.40 mmol) was used instead of C1 (5.7 g, 3.50 mmol).

[0410] MS (m / z): 968.21

[0411] <Preparation of Compound 310>

[0412] Intermediate C16 (7.3 g, 38% yield) was obtained in the same manner as in the preparation of compound C1, except that B16 (8.6 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 310 (2.3 g, 57% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and (Z)-5-hydroxy-2,2,6,6-tetramethylhept-4-en-3-one (1.3 g, 6.78 mmol).

[0413] MS (m / z): 1266.47

[0414] <Preparation of Compound 311>

[0415] Intermediate C17 (7.6 g, 39% yield) was obtained in the same manner as in the preparation of compound C1, except that B17 (8.9 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 311 (2.2 g, 50% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and (Z)-3,7-diethyl-6-hydroxynon-5-en-4-one (1.9 g, 6.97 mmol).

[0416] MS (m / z): 1307.51

[0417] <Preparation of Compound 360>

[0418] Intermediate C18 (5.3 g, 32% yield) was obtained in the same manner as in the preparation of compound C1, except that B18 (7.0 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 360 (1.6 g, 54% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and (Z)-3,7-diethyl-6-hydroxynon-5-en-4-one (1.9 g, 5.72 mmol).

[0419] MS (m / z): 1118.44

[0420] <Preparation of Compound 403>

[0421] Intermediate C19 (8.5 g, 43% yield) was obtained in the same manner as in the preparation of compound C1, except that B19 (8.9 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 403 (1.7 g, 37% yield) was obtained in the same manner as in the preparation of compound 1, except that C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and (Z)-3,7-diethyl-6-hydroxynon-5-en-4-one (1.6 g, 7.68 mmol).

[0422] MS (m / z): 1276.52

[0423] <Preparation of Compound 412>

[0424] Intermediate C20 (8.0 g, 44% yield) was obtained in the same manner as in the preparation of compound C1, except that B20 (8.0 g, 18.72 mmol) was used instead of B1 (5.5 g, 18.72 mmol). Compound 412 (1.9 g, 41% yield) was obtained in the same manner as in the preparation of compound 1, except that C20 (8.0 g, 3.74 mmol) and (Z)-5-hydroxy-2,2,6,6-tetramethylhept-4-en-3-one (1.4 g, 7.86 mmol) were used instead of C1 (5.7 g, 3.50 mmol) and pentane-2,4-dione (3.5 g, 7.35 mmol).

[0425] MS (m / z): 1230.54

[0426] <Preparation of Compound 433>

[0427]

[0428] Step 1) Preparation of compound C21

[0429] B21 (8.6 g, 18.72 mmol), 100 mL of 1,4-dioxane, and 20 mL of H2O were introduced into a reaction vessel and bubbled with nitrogen for 1 hour. Then, IrCl3(H2O)X (3 g, 8.51 mmol) was added, and the mixture was stirred at 100 °C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and the resulting solid was filtered. The filtered solid was dried to obtain intermediate C21 (7.9 g).

[0430] Step 2) Preparation of compound 433

[0431] C21 (7.9 g, 3.46 mmol), 3,7-diisopropyl-2,3,7,8-tetramethylnonane-4,6-dione (2.2 g, 7.27 mmol), and Na2CO3 (7.3 g, 69.24 mmol) were added to a reaction vessel and dissolved in 100 mL of 1,4-dioxane. The mixture was stirred for 24 hours. After the reaction was complete, the mixture was dissolved in excess MC for extraction. Anhydrous MgSO4 was added to the organic layer, and filtration was performed. The filtrate was concentrated under reduced pressure, and the mixture was recrystallized to obtain compound 433 (2.1 g).

[0432] MS (m / z): 1400.69

[0433] Example

[0434] <Example 1>

[0435] It is coated with a layer of ITO (indium tin oxide) with a thickness of [missing information]. The glass substrate of the thin film is washed, and the glass substrate is ultrasonically cleaned and dried using a solvent such as isopropanol, acetone or methanol.

[0436] A 60 nm thick layer of HI-1, serving as a hole injection material, was formed on the prepared ITO transparent electrode via thermal vacuum deposition. An 80 nm thick layer of NPB, serving as a hole transport material, was then thermally vacuum deposited on the hole injection layer. A light-emitting layer was then thermally vacuum deposited on the hole transport material. In this regard, the light-emitting layer contained CBP as the host material and Compound 1 as a dopant. The doping concentration was 5%, and the thickness of the light-emitting layer was 30 nm. An ET-1:Liq(1:1) (30 nm) material, serving as both an electron transport layer and an electron injection layer, was then thermally vacuum deposited on the light-emitting layer. Then, a 100 nm thick layer of aluminum was deposited on top to form the negative electrode. Thus, an organic electroluminescent device was fabricated. The materials used in Example 1 described above are as follows.

[0437]

[0438]

[0439] In this material, HI-1 is NNPPB, and ET-1 is ZADN.

[0440] <Example 2>

[0441] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 4 was used instead of compound 1 in Example 1 above.

[0442] <Example 3>

[0443] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 24 was used instead of compound 1 in Example 1 above.

[0444] <Example 4>

[0445] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 36 was used instead of compound 1 in Example 1 above.

[0446] <Example 5>

[0447] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 58 was used instead of compound 1 in Example 1 above.

[0448] <Example 6>

[0449] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 88 was used instead of compound 1 in Example 1 above.

[0450] <Example 7>

[0451] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 127 was used instead of compound 1 in Example 1 above.

[0452] <Example 8>

[0453] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 129 was used instead of compound 1 in Example 1 above.

[0454] <Example 9>

[0455] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 163 was used instead of compound 1 in Example 1 above.

[0456] <Example 10>

[0457] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 171 was used instead of compound 1 in Example 1 above.

[0458] <Example 11>

[0459] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 220 was used instead of compound 1 in Example 1 above.

[0460] <Example 12>

[0461] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 232 was used instead of compound 1 in Example 1 above.

[0462] <Example 13>

[0463] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 236 was used instead of compound 1 in Example 1 above.

[0464] <Example 14>

[0465] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 239 was used instead of compound 1 in Example 1 above.

[0466] <Example 15>

[0467] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 241 was used instead of compound 1 in Example 1 above.

[0468] <Example 16>

[0469] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 264 was used instead of compound 1 in Example 1 above.

[0470] <Example 17>

[0471] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 266 was used instead of compound 1 in Example 1 above.

[0472] <Example 18>

[0473] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 286 was used instead of compound 1 in Example 1 above.

[0474] <Example 19>

[0475] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 310 was used instead of compound 1 in Example 1 above.

[0476] <Example 20>

[0477] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 311 was used instead of compound 1 in Example 1 above.

[0478] <Example 21>

[0479] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 360 was used instead of compound 1 in Example 1 above.

[0480] <Example 22>

[0481] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 403 was used instead of compound 1 in Example 1 above.

[0482] <Example 23>

[0483] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 412 was used instead of compound 1 in Example 1 above.

[0484] <Example 24>

[0485] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 433 was used instead of compound 1 in Example 1 above.

[0486] <Example 25>

[0487] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 434 was used instead of compound 1 in Example 1 above.

[0488] <Example 26>

[0489] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 435 was used instead of compound 1 in Example 1 above.

[0490] <Example 27>

[0491] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 436 was used instead of compound 1 in Example 1 above.

[0492] <Example 28>

[0493] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 437 was used instead of compound 1 in Example 1 above.

[0494] <Example 29>

[0495] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 438 was used instead of compound 1 in Example 1 above.

[0496] <Example 30>

[0497] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 439 was used instead of compound 1 in Example 1 above.

[0498] <Example 31>

[0499] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 440 was used instead of compound 1 in Example 1 above.

[0500] <Example 32>

[0501] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 441 was used instead of compound 1 in Example 1 above.

[0502] <Example 33>

[0503] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 442 was used instead of compound 1 in Example 1 above.

[0504] <Example 34>

[0505] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 443 was used instead of compound 1 in Example 1 above.

[0506] <Example 35>

[0507] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 444 was used instead of compound 1 in Example 1 above.

[0508] <Example 36>

[0509] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 445 was used instead of compound 1 in Example 1 above.

[0510] <Example 37>

[0511] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 446 was used instead of compound 1 in Example 1 above.

[0512] <Example 38>

[0513] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 447 was used instead of compound 1 in Example 1 above.

[0514] <Example 39>

[0515] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 448 was used instead of compound 1 in Example 1 above.

[0516] <Example 40>

[0517] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 449 was used instead of compound 1 in Example 1 above.

[0518] <Example 41>

[0519] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 450 was used instead of compound 1 in Example 1 above.

[0520] <Example 42>

[0521] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 451 was used instead of compound 1 in Example 1 above.

[0522] <Example 43>

[0523] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 452 was used instead of compound 1 in Example 1 above.

[0524] <Example 44>

[0525] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 453 was used instead of compound 1 in Example 1 above.

[0526] <Example 45>

[0527] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 454 was used instead of compound 1 in Example 1 above.

[0528] <Example 46>

[0529] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 455 was used instead of compound 1 in Example 1 above.

[0530] <Example 47>

[0531] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 456 was used instead of compound 1 in Example 1 above.

[0532] <Example 48>

[0533] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 457 was used instead of compound 1 in Example 1 above.

[0534] <Example 49>

[0535] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 458 was used instead of compound 1 in Example 1 above.

[0536] <Example 50>

[0537] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 459 was used instead of compound 1 in Example 1 above.

[0538] <Example 51>

[0539] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 460 was used instead of compound 1 in Example 1 above.

[0540] <Example 52>

[0541] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 461 was used instead of compound 1 in Example 1 above.

[0542] <Example 53>

[0543] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 462 was used instead of compound 1 in Example 1 above.

[0544] <Example 54>

[0545] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 463 was used instead of compound 1 in Example 1 above.

[0546] <Example 55>

[0547] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 464 was used instead of compound 1 in Example 1 above.

[0548] <Example 56>

[0549] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 465 was used instead of compound 1 in Example 1 above.

[0550] <Example 57>

[0551] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that compound 466 was used instead of compound 1 in Example 1 above.

[0552] <Comparative Example 1>

[0553] An organic electroluminescent device was manufactured in the same manner as in Example 1 above, except that RD having the following structure was used instead of compound 1 in Example 1 above.

[0554]

[0555] Experimental Example

[0556] Each organic electroluminescent device prepared in Examples 1 to 57 and Comparative Example 1 was connected to an external power source, and the characteristics of the organic electroluminescent devices were evaluated at room temperature using a current source and a photometer.

[0557] Specifically, at 10 mA / cm 2 The driving voltage, external quantum efficiency (EQE), lifetime characteristics (LT95), and full width at half maximum (FWHM) were measured under the current, and the results are shown in Tables 1 and 2 below.

[0558] LT95 lifespan refers to the time it takes for a display element to lose 5% of its initial brightness. LT95 lifespan is the most difficult customer specification to meet, as it determines whether a monitor will exhibit image aging.

[0559] Full width at half maximum (FWHM) refers to the wavelength width corresponding to half the maximum value of the curve (kr) representing the wavelength (see [reference]). Figure 3 A narrow FWHM means a wide range of colors that can be rendered, thus allowing for colors closer to natural colors and improving the color gamut. The FWHM was evaluated based on photoluminescence (PL) intensity measurements, and the measurement equipment was model / manufacturer FS-5 / Edinburgh Instruments.

[0560] Table 1

[0561]

[0562]

[0563]

[0564] Table 2

[0565]

[0566]

[0567]

[0568] The structural difference between the dopant compound of the light-emitting layer in Comparative Example 1 of this disclosure and the compound represented by Chemical Formula 1 in this embodiment of the disclosure is that no additional ring is introduced into the 6-membered ring in which X1 is introduced.

[0569] As can be seen from the results in Tables 1 and 2, compared with Comparative Example 1, the organic electroluminescent devices using the organometallic compounds used as dopants in Examples 1 to 57 of this disclosure as the light-emitting layer have a lower driving voltage, improved external quantum efficiency (EQE) and lifetime (LT95), and improved color purity due to the narrow full width at half maximum (FWHM).

[0570] The scope of protection of this disclosure should be understood through the scope of the claims, and all technical concepts within the scope of the claims should be understood to be included within the scope of this disclosure. Although embodiments of this disclosure have been described in more detail with reference to the accompanying drawings, this disclosure is not necessarily limited to these embodiments. This disclosure can be implemented in various modifications without departing from the scope of the technical concept of this disclosure. Therefore, the embodiments disclosed in this disclosure are not intended to limit the technical concept of this disclosure, but are used to describe this disclosure. The scope of the technical concept of this disclosure is not limited by these embodiments. Therefore, it should be understood that the embodiments described above are illustrative and not restrictive in all respects. The scope of protection of this disclosure should be interpreted through the claims, and all technical concepts within the scope of this disclosure should be understood to be included within the scope of this disclosure.

Claims

1. An organometallic compound represented by chemical formula 1: Chemical Formula 1 In chemical formula 1, M represents the centrally coordinated metal iridium (Ir); Y may be the same as or different from each other, and independently represent one of the groups consisting of CR1R2, SiR1R2, NR1, oxygen (O), sulfur (S) and selenium (Se); X1 represents nitrogen (N), and X2 represents carbon (C); R1 and R2 each independently represent one selected from the group consisting of hydrogen, deuterium, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 heteroalkyl, C7-C20 aralkyl, and C1-C20 alkenyl; R a R b and R c Each independently represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 heteroalkyl, C7-C20 aralkyl and C1-C20 alkenyl; It is a bidentate ligand; m is an integer of 1, 2, or 3, n is an integer of 0, 1, or 2, and m+n is the oxidation number of metal M; X3, X4, X5, X6, X7, X8, X9, X 10 X 11 X 12 X 13 and X 14 Each CR is represented independently; When Y is CR1R2, at least one R is not H. The compound represented by chemical formula 1 is a compound represented by one of the following chemical formulas: chemical formula 5, chemical formula 7, chemical formula 9 and chemical formula 11. Chemical formula 5 Chemical Formula 7 Chemical formula 9 Chemical Formula 11 In each of the chemical formulas 5, 7, 9, and 11, X 24 X 25 X 26 and X 27 They are the same or different from each other, and X 24 X 25 X 26 and X 27 Each represents CR and nitrogen (N) independently; Z3 and Z4 are both NR7; R6 and R7, and X 24 To X 27 Each of the Rs in the group represents one selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, cyano, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 heteroalkyl, C7-C20 aralkyl, and C1-C20 alkenyl.

2. The organometallic compound according to claim 1, wherein Y represents a compound selected from the group consisting of oxygen (O), sulfur (S) and CRIR2.

3. An organometallic compound, wherein the organometallic compound comprises one selected from the group consisting of compounds 99, 122, 124, 174, 176, 239, 248, 262, 264, 307, 322, 364, 367, 376, 382 and 384: 。 4. An organic electroluminescent device, comprising: First electrode; The second electrode facing the first electrode; and An organic layer disposed between the first electrode and the second electrode. The organic layer includes a light-emitting layer, and The light-emitting layer comprises the organometallic compound according to claim 1.

5. The organic electroluminescent device according to claim 4, wherein the organometallic compound is used as a dopant in the light-emitting layer.

6. The organic electroluminescent device according to claim 4, 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.

7. The organic electroluminescent device according to claim 4, wherein the organic layer is formed by sequentially stacking a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and an electron injection layer on the first electrode.

8. The organic electroluminescent device according to claim 6, wherein the hole injection layer comprises a compound selected from the group consisting of: MTDATA, CuPc, TCTA, NPB (NPD), HATCN, TDAPB, PEDOT / PSS, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, and NPNPB (N,N'-diphenyl-N,N'-bis[4-(N,N-diphenyl-amino)phenyl]benzidine).

9. The organic electroluminescent device according to claim 6, wherein the hole transport layer comprises a compound selected from the group consisting of: TPD, NPD, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine.

10. The organic electroluminescent device according to claim 4, wherein the light-emitting layer comprises a host and the organometallic compound represented by chemical formula I as a dopant, wherein the host material is selected from the group consisting of CBP and mCP.

11. The organic electroluminescent device according to claim 6, wherein the electron transport layer and the electron injection layer are sequentially stacked between the light-emitting layer and the second electrode.

12. The organic electroluminescent device according to claim 6, wherein the electron transport layer comprises a compound selected from the group consisting of: Alq3 (tris(8-hydroxyquinoline)aluminum), Liq (lithium 8-hydroxyquinoline), PBD (2-(4-biphenyl))-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), TAZ (3-(4-biphenyl)4-phenyl-5-tert-butylphenyl-1,2,4-triazole), spiro-PBD, BAlq (bis(2-methyl-8-quinoline acid)-4-(phenylphenol)aluminum), SAlq, TPBi, oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, and ZADN (2-[4-(9,10-di-naphthyl-2-yl-2-anthracene-2-yl)phenyl]-1-phenyl-1H-benzimidazole).

13. The organic electroluminescent device according to claim 6, wherein the electron injection layer comprises a compound selected from the group consisting of: Alq3 (tris(8-hydroxyquinoline)aluminum), PBD, TAZ, spiro-PBD, BAlq and SAlq.

14. The organic electroluminescent device according to claim 6, wherein the electron injection layer comprises a metal compound selected from the group consisting of: Liq, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2 and RaF2.

15. The organic electroluminescent device according to claim 6, wherein the organic electroluminescent device has a series structure comprising two light-emitting stacks or three light-emitting stacks.

16. An organic light-emitting display device, comprising: substrate; Drive elements located on the substrate; and An organic light-emitting element, wherein the organic light-emitting element is disposed on the substrate and connected to the driving element. The organic light-emitting element described herein includes the organic electroluminescent device according to claim 5.

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