Organometallic compound, organic light emitting diode and organic light emitting device including the organometallic compound

Abstract

The present invention provides an organometallic compound represented by the following chemical formula, an organic light-emitting diode containing the same in a light-emitting material layer, and an organic light-emitting display device.

Description

Technology Field

[0001] The present invention relates to metal compounds, and more specifically, to organometallic compounds with improved luminous efficiency and luminous lifetime, and to organic light-emitting diodes and organic light-emitting devices containing the same. Background Technology

[0003] Recently, with the increasing size of display devices, there is a growing demand for flat display devices that occupy less space. As one of these flat display devices, the technology of organic light emitting display (OLED) devices, which include organic light-emitting diodes and are also called organic electroluminescent devices (OLEDs), is developing rapidly.

[0004] An organic light-emitting diode (OLED) is a device formed between an electron injection electrode (cathode) and a hole injection electrode (anode) and comprises an organic light-emitting layer containing a host and a dopant. When charge is injected into the organic light-emitting layer, electrons and holes pair up and annihilate, emitting light. It has the advantages of being able to be formed on flexible transparent substrates such as plastic, operating at low voltages (below 10V), consuming relatively little power, and possessing excellent color purity.

[0005] Dopants can be classified into fluorescent materials and phosphorescent materials.

[0006] Conventional fluorescent materials have low luminescence efficiency because only singlet excitons participate in luminescence. Phosphorescent materials, in which triplet excitons also participate in luminescence, have higher luminescence efficiency compared to fluorescent materials. However, organometallic compounds, which are representative phosphorescent materials, have short luminescence lifetimes, which limits their commercialization. Therefore, there is a need to develop compounds with improved luminescence efficiency and luminescence lifetimes. The problem to be solved

[0008] The present invention aims to solve the limitations of the luminous efficiency and lifespan of conventional dopants. means of solving the problem

[0010] To solve the above problems, the present invention comprises a formula represented by the following chemical formula 1, wherein each of X1 to X5 is independently N or CR4, and each of R1, R21, R22, R23, R31, R32, and R33 is independently selected from the group consisting of deuterium, halide, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C3 to C20 cycloalkyl group, an unsubstituted or deuterium-substituted C6 to C30 aryl group, or an unsubstituted or deuterium-substituted C1 to C10 alkyl group, and a C3 to C30 heteroaryl group, wherein R4 is hydrogen, deuterium, halide, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C3 to C20 cycloalkyl group, or an unsubstituted or deuterium-substituted C1 to C10 alkyl group. The present invention provides an organometallic compound selected from the group consisting of a C6 to C30 aryl group substituted with an alkyl group, a C3 to C30 heteroaryl group that is not substituted or is substituted with a deuterium or a C1 to C10 alkyl group, wherein R5, R6, and R7 are each independently a C1 to C10 alkyl group, a to g are 0 or 1, and n is an integer from 0 to 2.

[0011] [Chemical Formula 1]

[0012]

[0013] In the organometallic compound of the present invention, X1 to X5 are characterized as being CR4.

[0014] The organometallic compound of the present invention is characterized in that n is 2.

[0015] In another aspect, the present invention provides an organic light-emitting diode comprising: a first electrode; a second electrode facing the first electrode; and a first light-emitting unit positioned between the first electrode and the second electrode and comprising a first light-emitting material layer, wherein the first light-emitting material layer comprises the aforementioned organometallic compound.

[0016] In the organic light-emitting diode of the present invention, the first light-emitting material layer comprises a first host and a first dopant, and the first dopant is characterized as being the organometallic compound.

[0017] The organic light-emitting diode of the present invention comprises a second light-emitting unit positioned between the first light-emitting unit and the first electrode, and further comprises a first charge-generating layer positioned between the first light-emitting unit and the second light-emitting unit, wherein the second light-emitting material layer comprises a blue dopant.

[0018] In the organic light-emitting diode of the present invention, the first light-emitting unit further comprises a third light-emitting material layer located below or above the first light-emitting material layer, and the third light-emitting material layer comprises a red dopant.

[0019] The organic light-emitting diode of the present invention comprises: a third light-emitting unit located between the second light-emitting unit and the second electrode and including a third light-emitting material layer; and a second charge-generating layer located between the second light-emitting unit and the third light-emitting unit, wherein the third light-emitting material layer includes a red dopant.

[0020] The organic light-emitting diode of the present invention comprises: a third light-emitting unit located between the second light-emitting unit and the second electrode and including a third light-emitting material layer; and a second charge-generating layer located between the second light-emitting unit and the third light-emitting unit, wherein the first light-emitting unit further comprises a fourth light-emitting material layer located below or above the first light-emitting material layer, wherein the third light-emitting material layer includes a blue dopant and the fourth light-emitting material layer includes a red dopant.

[0021] In another aspect, the present invention comprises: a substrate; an organic light-emitting diode comprising a first light-emitting unit positioned on the substrate, the first electrode, a second electrode facing the first electrode, and a first light-emitting material layer positioned between the first electrode and the second electrode;

[0022] The present invention provides an organic light-emitting device comprising a thin-film transistor located between the substrate and the organic light-emitting diode and connected to the organic light-emitting diode, wherein the first light-emitting material layer comprises the aforementioned organometallic compound.

[0023] In the organic light-emitting device of the present invention, the first light-emitting material layer comprises a first host and a first dopant, and the first dopant is characterized as being the organometallic compound.

[0024] In the organic light-emitting device of the present invention, the organic light-emitting diode further comprises a second light-emitting unit located between the first light-emitting unit and the first electrode, and a first charge-generating layer located between the first light-emitting unit and the second light-emitting unit, wherein the second light-emitting material layer comprises a blue dopant.

[0025] In the organic light-emitting device of the present invention, the first light-emitting unit further comprises a third light-emitting material layer located below or above the first light-emitting material layer, and the third light-emitting material layer comprises a red dopant.

[0026] In the organic light-emitting device of the present invention, the organic light-emitting diode further comprises a third light-emitting unit located between the second light-emitting unit and the second electrode and including a third light-emitting material layer, and a second charge-generating layer located between the second light-emitting unit and the third light-emitting unit, wherein the third light-emitting material layer includes a red dopant.

[0027] In the organic light-emitting device of the present invention, the organic light-emitting diode further comprises a third light-emitting unit located between the second light-emitting unit and the second electrode and including a third light-emitting material layer, and a second charge-generating layer located between the second light-emitting unit and the third light-emitting unit, wherein the first light-emitting unit further comprises a fourth light-emitting material layer located below or above the first light-emitting material layer, and wherein the third light-emitting material layer comprises a blue dopant and the fourth light-emitting material layer comprises a red dopant.

[0028] The organic light-emitting device of the present invention is characterized in that, in the substrate, a red pixel, a green pixel, and a blue pixel are defined, and the organic light-emitting diode corresponds to the red pixel, the green pixel, and the blue pixel, and further comprises a color filter layer located between the substrate and the organic light-emitting diode or on top of the organic light-emitting diode corresponding to the red pixel, the green pixel, and the blue pixel. Effects of the invention

[0030] The organometallic compound of the present invention is an iridium complex comprising a pyridine moiety and a condensed ring moiety connected thereto that contains oxygen, and has a first ligand having a structure in which an alkylsilyl group is bonded to a specific position of the condensed ring moiety. Accordingly, the luminous efficiency and lifespan of an organic light-emitting diode and an organic light-emitting device comprising the organometallic compound are improved.

[0031] In addition, the organometallic compound may further include a second ligand comprising a benzene moiety and a pyridine moiety connected thereto, and at least one of the hydrogens of the pyridine moiety of the second ligand is substituted with a non-oxidized C1 to C10 alkyl group, thereby further improving the luminous efficiency and lifespan of the organic light-emitting diode and organic light-emitting display device comprising the organometallic compound.

[0032] In addition, at least one of the hydrogens of the pyridine moiety of the first ligand is substituted with one of an unsubstituted or deuterium-substituted C1 to C10 alkyl group or an unsubstituted C1 to C10 cycloalkyl group, thereby further improving the luminous efficiency and lifespan of the organic light-emitting diode and organic light-emitting display device containing the organometallic compound. Brief explanation of the drawing

[0034] FIG. 1 is a schematic circuit diagram of an organic light-emitting display device according to the present invention. FIG. 2 is a schematic cross-sectional view of an organic light-emitting display device according to a first embodiment of the present invention. FIG. 3 is a schematic cross-sectional view of an organic light-emitting diode according to a second embodiment of the present invention. FIG. 4 is a schematic cross-sectional view of an organic light-emitting display device according to a third embodiment of the present invention. FIG. 5 is a schematic cross-sectional view of an organic light-emitting diode according to a fourth embodiment of the present invention. FIG. 6 is a schematic cross-sectional view of an organic light-emitting diode according to the fifth embodiment of the present invention. FIG. 7 is a schematic cross-sectional view of an organic light-emitting diode according to the 6th embodiment of the present invention. FIG. 8 is a schematic cross-sectional view of an organic light-emitting diode according to the seventh embodiment of the present invention. Specific details for implementing the invention

[0035] Hereinafter, preferred embodiments according to the present invention will be described with reference to the drawings.

[0036] The organometallic compound according to the present invention has improved luminescence efficiency and luminescence lifetime. The organometallic compound according to the present invention has the structure of Chemical Formula 1 below.

[0037] [Chemical Formula 1]

[0038]

[0039] In Formula 1, each of X1 to X5 is independently N or CR4, and each of R1, R21, R22, R23, R31, R32, R33 is independently selected from the group consisting of deuterium, halide, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C3 to C20 cycloalkyl group, an unsubstituted or deuterium-substituted C6 to C30 aryl group, or an unsubstituted or deuterium-substituted C1 to C10 alkyl group, or a C3 to C30 heteroaryl group. R4 is selected from the group consisting of hydrogen, deuterium, halide, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C3 to C20 cycloalkyl group, an unsubstituted or deuterium-substituted C6 to C30 aryl group, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, and a C3 to C30 heteroaryl group, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, and R5, R6, and R7 are each independently C1 to C10 alkyl groups. Additionally, a to g are 0 or 1, and n is an integer from 0 to 2.

[0040] That is, the organometallic compound of the present invention is an iridium complex and has a first ligand having a structure comprising a pyridine moiety and a condensed ring moiety connected thereto that contains oxygen, and an alkylsilyl group bonded to a specific position of the condensed ring moiety, and emits light in the wavelength range of about 500 to 540 nm, for example, light in the wavelength range of about 520 to 525 nm. Accordingly, the luminous efficiency and lifespan of organic light-emitting diodes and organic light-emitting devices containing the organometallic compound are improved.

[0041] For example, R1, R21, R22, and R23 may each be an unsubstituted C1 to C10 alkyl group, for example, a methyl group. Additionally, R31, R32, and R33 may each be an unsubstituted C1 to C10 alkyl group, for example, methyl, tertiarybutyl, neopentyl, an unsubstituted C1 to C10 cycloalkyl group, for example, cyclopentyl, or a C1 to C10 alkyl group substituted with deuterium, for example, CD3.

[0042] The organometallic compound of the present invention may include a second ligand comprising a benzene moiety and a pyridine moiety connected thereto, and at least one of the hydrogens of the pyridine moiety in the second ligand may be substituted. That is, in Formula 1, n is 1 or 2, and at least one of b, c, and d may be 1.

[0043] For example, in Chemical Formula 1, b can be 1, and c and d can be 0, and the organometallic compound of the present invention can be represented by the following Chemical Formula 2-1.

[0044] [Chemical Formula 2-1]

[0045]

[0046] In addition, in the organometallic compound of the present invention, at least one of the hydrogens of the pyridine moiety of the first ligand may be substituted. That is, at least one of e, f, and g in Formula 1 may be 1.

[0047] For example, in Chemical Formula 1, e can be 1, and f and g can be 0, and the organometallic compound of the present invention can be represented by the following Chemical Formula 2-2.

[0048] [Chemical Formula 2-2]

[0049]

[0050] In contrast, in Chemical Formula 1, f can be 1, and e and g can be 0, and the organometallic compound of the present invention can be represented by the following Chemical Formula 2-3.

[0051] [Chemical Formula 2-3]

[0052]

[0053] An organometallic compound having the structure of Chemical Formula 1 includes iridium as a central coordination metal, a pyridine moiety and a condensed ring moiety connected thereto that includes oxygen, and a first ligand having a structure in which an alkylsilyl group is bonded to a specific position of the condensed ring moiety. Accordingly, the luminous efficiency and lifespan of an organic light-emitting diode and an organic light-emitting display device (100) containing the organometallic compound are improved.

[0054] In addition, the organometallic compound may further comprise a second ligand comprising a benzene moiety and a pyridine moiety connected thereto, and at least one hydrogen of the pyridine moiety of the second ligand is substituted with a non-modified C1 to C10 alkyl group, thereby further improving the luminous efficiency and lifespan of the organic light-emitting diode and organic light-emitting display device comprising the organometallic compound. (Chemical Formula 2-1)

[0055] In addition, by substituting at least one hydrogen of the pyridine moiety of the first ligand with one of an unsubstituted or deuterium-substituted C1 to C10 alkyl group or an unsubstituted C1 to C10 cycloalkyl group, the luminous efficiency and lifespan of the organic light-emitting diode and organic light-emitting display device comprising the organometallic compound are further improved. (Chemical Formula 2-2, Chemical Formula 2-3)

[0056] In particular, as in Chemical Formula 2-2, when the hydrogen at the 2nd position in the pyridine moiety of the first ligand is substituted, organic light-emitting diodes and organic light-emitting display devices containing organometallic compounds have a high lifespan and significantly increased luminous efficiency.

[0057] In addition, when the bidentate ligands bonded to the central metal are different heteropleptic metal complexes (n=2), the luminous efficiency and lifespan of organic light-emitting diodes and organic light-emitting display devices containing organometallic compounds are significantly improved.

[0058] For example, the organometallic compound of Chemical Formula 1 may be any one of the substances of Chemical Formula 3 below.

[0059] [Chemical Formula 3]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

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[0075]

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[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] [Example of Intermediate Synthesis]

[0135] 1. Synthesis of Compound A

[0136] (1) Compound A-4

[0137] [Reaction Equation 1-1]

[0138]

[0139] SM-1 (49.14 g, 0.20 mol), (1R, 2R)-cyclohexane-1,2-diamine (23.11 g, 0.20 mol), acetamide (35.85 g, 0.61 mol), copper(I) iodide (38.54 g, 0.20 mol), and potassium carbonate (100 g, 0.40 mol) were dissolved in toluene (500 mL) in a 1 L round-bottom flask under a nitrogen atmosphere and heated while stirring under reflux overnight. After the reaction was complete, the mixture was filtered through a Celite pad filter, and the organic layer was extracted and separated using ethyl acetate and distilled water. The organic layer was dehydrated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized with dichloromethane and hexane to obtain compound A-4 (18.45 g, 41%).

[0140] (2) Compound A-3

[0141] [Reaction Equation 1-2]

[0142]

[0143] Under a nitrogen atmosphere, A-4 (24.75 g, 0.11 mol) was dissolved in acetic acid (300 mL) in a 250 mL round-bottom flask, and then bromine (5.69 mL, 0.11 mol) diluted with acetic acid (100 mL) was added to the reaction solution and stirred at room temperature for 4 hours. Upon completion of the reaction, the solid formed at the bottom of the reaction vessel was filtered and thoroughly washed with distilled water. The solid obtained after filtration was dissolved in a mixed solution (THF:EtOH:distilled water = 1:1:1, 500 mL), potassium hydroxide (125 g, 0.56 mol) was added, and the mixture was heated and stirred under reflux overnight. After the reaction was complete, the organic layer was extracted and separated using ethyl acetate and distilled water. The organic layer was dehydrated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized with ethyl acetate and hexane to obtain compound A-3 (20.67 g, 72%).

[0144] (3) Compound A-2

[0145] [Reaction Equation 1-3]

[0146]

[0147] Under a nitrogen atmosphere, A-3 (18.27 g, 0.07 mol) and bis(pinacollato)diborone (25.84 g, 0.07 mol) were added to 200 mL of acetonitrile in a 250 mL round-bottom flask, dissolved, and stirred at room temperature. Subsequently, tertiary-butylnitrite (13.1 g, 0.12 mol) was added to the reaction solution, and the temperature was raised to 80 °C and stirred for 2 hours. Once the reaction was complete, the temperature of the reaction vessel was lowered to room temperature. The reaction solution was concentrated under reduced pressure, separated by column chromatography, and purified to obtain compound A-2 (10.94 g, 42%).

[0148] (4) Compound A-1

[0149] [Reaction Equation 1-4]

[0150]

[0151] Compound A-2 (7.44 g, 20 mmol), SM-3 (3.14 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. Water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography to obtain compound A-1 (5.49 g, 85%).

[0152] (5) Compound A

[0153] [Reaction Equation 1-5]

[0154]

[0155] Compound A-1 (4.84 g, 15 mmol) was placed in 100 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere and cooled to -78 °C. 1.6 M n-BuLi (14.06 mL, 22.50 mmol) was slowly added, and the mixture was stirred at -78 °C for 1 hour. Trimethylsilyl chloride (TMSCl, 2.85 mL, 22.50 mmol) was added to the reaction vessel and stirred at -78 °C for 1 hour; afterward, the temperature was raised, and the reaction was carried out at room temperature for 12 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and thoroughly washed with water. Anhydrous magnesium sulfate was added to remove moisture, and the filtered solution was concentrated under reduced pressure and separated by column chromatography under conditions of Ethylacetate:Hexane = 10:90 to obtain Compound A (3.09 g, 65%).

[0156] 2. Synthesis of Compound B

[0157] (1) Compound B-1

[0158] [Reaction Equation 2-1]

[0159]

[0160] Compound A-2 (7.44 g, 20 mmol), SM-4 (3.42 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. Water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography to obtain compound B-1 (5.53 g, 82%).

[0161] (2) Compound B

[0162] [Reaction Equation 2-2]

[0163]

[0164] Compound B-1 (5.06 g, 15 mmol) was placed in 100 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere and cooled to -78 °C. Then, 1.6 M n-BuLi (14.06 mL, 22.50 mmol) was slowly added and stirred at -78 °C for 1 hour. TMSCl (2.85 mL, 22.50 mmol) was added to the reaction vessel and stirred at -78 °C for 1 hour. Afterward, the temperature was raised and the reaction was carried out at room temperature for 12 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and thoroughly washed with water. Anhydrous magnesium sulfate was added to remove moisture, and the filtered solution was concentrated under reduced pressure and separated by column chromatography under conditions of Ethylacetate:Hexane = 10:90 to obtain Compound B (3.73 g, 75%).

[0165] 3. Synthesis of Compound C

[0166] (1) Compound C-1

[0167] [Reaction Equation 3-1]

[0168]

[0169] Compound A-2 (7.44 g, 20 mmol), SM-5 (4.26 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. Water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography to obtain compound C-1 (6.44 g, 85%).

[0170] (2) Compound C

[0171] [Reaction Equation 3-2]

[0172]

[0173] Compound C-1 (5.69 g, 15 mmol) was placed in 100 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere and cooled to -78 °C. Then, 1.6 M n-BuLi (14.06 mL, 22.50 mmol) was slowly added and stirred at -78 °C for 1 hour. TMSCl (2.85 mL, 22.50 mmol) was added to the reaction vessel and stirred at -78 °C for 1 hour. Afterward, the temperature was raised and the reaction was carried out at room temperature for 12 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and thoroughly washed with water. Anhydrous magnesium sulfate was added to remove moisture, and the filtered solution was concentrated under reduced pressure and separated by column chromatography under conditions of Ethylacetate:Hexane = 10:90 to obtain Compound C (3.97 g, 71%).

[0174] 4. Synthesis of Compound D

[0175] (1) Compound D-1

[0176] [Reaction Equation 4-1]

[0177]

[0178] Compound A-2 (7.44 g, 20 mmol), SM-6 (3.48 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. Water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography to obtain compound D-1 (5.44 g, 80%).

[0179] (2) Compound D

[0180] [Reaction Equation 4-2]

[0181]

[0182] Compound D-1 (5.10 g, 15 mmol) was placed in 100 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere and cooled to -78 °C. Then, 1.6 M n-BuLi (14.06 mL, 22.50 mmol) was slowly added and stirred at -78 °C for 1 hour. TMSCl (2.85 mL, 22.50 mmol) was added to the reaction vessel and stirred at -78 °C for 1 hour. Afterward, the temperature was raised and the reaction was carried out at room temperature for 12 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and thoroughly washed with water. Anhydrous magnesium sulfate was added to remove moisture, and the filtered solution was concentrated under reduced pressure and separated by column chromatography under conditions of Ethylacetate:Hexane = 10:90 to obtain Compound D (3.16 g, 63%).

[0183] 5. Synthesis of Compound E

[0184] (1) Compound E-4

[0185] [Reaction Equation 5-1]

[0186]

[0187] SM-2 (49.39 g, 0.20 mol), (1R, 2R)-cyclohexane-1,2-diamine (23.11 g, 0.20 mol), acetamide (35.85 g, 0.61 mol), copper(I) iodide (38.54 g, 0.20 mol), and potassium carbonate (100 g, 0.40 mol) were dissolved in 500 mL of toluene in a 1 L round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux overnight. After the reaction was complete, the mixture was filtered through a Celite pad filter, and the organic layer was extracted and separated using ethyl acetate and distilled water. The organic layer was dehydrated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The composition was recrystallized with dichloromethane and hexane to obtain E-4 (21.25 g, 47%).

[0188] (2) Compound E-3

[0189] [Reaction Equation 5-2]

[0190]

[0191] Under a nitrogen atmosphere, E-4 (24.87 g, 0.11 mol) was dissolved in 300 mL of acetic acid in a 250 mL round-bottom flask, and then diluted bromine (5.69 mL, 0.11 mol) was added to the reaction solution and stirred at room temperature for 4 hours. Upon completion of the reaction, the solid formed at the bottom of the reaction vessel was filtered and thoroughly washed with distilled water. The solid obtained after filtration was dissolved in 500 mL of a mixed solution (THF:EtOH:distilled water = 1:1:1), potassium hydroxide (125 g, 0.56 mol) was added, and the mixture was heated and stirred under reflux overnight. After the reaction was complete, the organic layer was extracted and separated using ethyl acetate and distilled water. The organic layer was dehydrated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized with ethyl acetate and hexane to obtain E-3 (19.88 g, 69%).

[0192] (3) Compound E-2

[0193] [Reaction Equation 5-3]

[0194]

[0195] Under a nitrogen atmosphere, E-3 (18.34 g, 0.07 mol) and bis(pinacollato)diborone (25.84 g, 0.07 mol) were added to 200 mL of acetonitrile in a 250 mL round-bottom flask, dissolved, and stirred at room temperature. Tertiary-butylnitrite (13.1 g, 0.12 mol) was added to the reaction solution, and the temperature was raised to 80 °C and stirred for 2 hours. Once the reaction was complete, the temperature of the reaction vessel was lowered to room temperature. The reaction solution was concentrated under reduced pressure, separated by column chromatography, and purified to obtain compound E-2 (12.27 g, 47%).

[0196] (4) Compound E-1

[0197] [Reaction Equation 5-4]

[0198]

[0199] Compound E-2 (7.46 g, 20 mmol), SM-4 (3.42 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. Water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography to obtain compound E-1 (4.87 g, 72%).

[0200] (5) Compound E

[0201] [Reaction Equation 5-5]

[0202]

[0203] Compound E-1 (5.07 g, 15 mmol) was placed in 100 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere and cooled to -78 °C. Then, 1.6 M n-BuLi (14.06 mL, 22.50 mmol) was slowly added and stirred at -78 °C for 1 hour. TMSCl (2.85 mL, 22.50 mmol) was added to the reaction vessel and stirred at -78 °C for 1 hour. Afterward, the temperature was raised and the reaction was carried out at room temperature for 12 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and thoroughly washed with water. Anhydrous magnesium sulfate was added to remove moisture, and the filtered solution was concentrated under reduced pressure and separated by column chromatography under conditions of Ethylacetate:Hexane = 10:90 to obtain Compound E (2.84 g, 57%).

[0204] 6. Synthesis of Compound F

[0205] (1) Compound F-1

[0206] [Reaction Equation 6-1]

[0207]

[0208] Compounds E-2 (7.46 g, 20 mmol), SM-6 (3.48 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. Water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography to obtain compound F-1 (5.25 g, 77%).

[0209] (2) Compound F

[0210] [Reaction Equation 6-2]

[0211]

[0212] Compound F-1 (5.12 g, 15 mmol) was placed in 100 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere and cooled to -78 °C. Then, 1.6 M n-BuLi (14.06 mL, 22.50 mmol) was slowly added and stirred at -78 °C for 1 hour. TMSCl (2.85 mL, 22.50 mmol) was added to the reaction vessel and stirred at -78 °C for 1 hour. Afterward, the temperature was raised and the reaction was carried out at room temperature for 12 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and thoroughly washed with water. Anhydrous magnesium sulfate was added to remove moisture, and the filtered solution was concentrated under reduced pressure and separated by column chromatography under conditions of Ethylacetate:Hexane = 10:90 to obtain Compound F (2.26 g, 45%).

[0213] 7. Synthesis of Compound AA

[0214] [Reaction Equation 7]

[0215]

[0216] A solution (Ethoxyethanol:distilled water = 90 mL:30 mL) containing compound A (6.34 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask under a nitrogen atmosphere and stirred under reflux for 24 hours. After the reaction was finished, the temperature was lowered to room temperature and the resulting solid was separated by vacuum filtration. The solid filtered through the filter was thoroughly washed with water and cold methanol, and then vacuum filtration was performed to obtain solid compound AA (28.21 g, 82%).

[0217] 8. Synthesis of Compound BB

[0218] [Reaction Equation 8]

[0219]

[0220] A solution (Ethoxyethanol:distilled water = 90 mL:30 mL) of compound B (6.62 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was added to a 250 mL round-bottom flask under a nitrogen atmosphere and stirred under reflux for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the resulting solid was separated by vacuum filtration. The solid filtered through the filter was thoroughly washed with water and cold methanol, and then vacuum filtration was performed to obtain solid compound BB (26.83 g, 78%).

[0221] 9. Synthesis of Compound CC

[0222] [Reaction Equation 9]

[0223]

[0224] A solution (Ethoxyethanol:distilled water = 90 mL:30 mL) containing compound C (7.46 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask under a nitrogen atmosphere and stirred under reflux for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the resulting solid was separated by vacuum filtration. The solid filtered through the filter was thoroughly washed with water and cold methanol, and then vacuum filtration was performed to obtain solid compound CC (33.06 g, 85%).

[0225] 10. Synthesis of Compound DD

[0226] [Reaction Equation 10]

[0227]

[0228] A solution (Ethoxyethanol:distilled water = 90 mL:30 mL) containing compound D (6.68 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask under a nitrogen atmosphere and stirred under reflux for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the resulting solid was separated by vacuum filtration. The solid filtered through the filter was thoroughly washed with water and cold methanol, and then vacuum filtration was performed to obtain solid compound DD (28.26 g, 79%).

[0229] 11. Synthesis of Compound EE

[0230] [Reaction Equation 11]

[0231]

[0232] A solution (Ethoxyethanol:distilled water = 90 mL:30 mL) containing compound E (6.64 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask under a nitrogen atmosphere and stirred under reflux for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the resulting solid was separated by vacuum filtration. The solid filtered through the filter was thoroughly washed with water and cold methanol, and then vacuum filtration was performed to obtain solid compound EE (26.35 g, 74%).

[0233] 12. Synthesis of Compound FF

[0234] [Reaction Equation 12]

[0235]

[0236] A solution (Ethoxyethanol:distilled water = 90 mL:30 mL) containing compound F (6.70 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask under a nitrogen atmosphere and stirred under reflux for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the resulting solid was separated by vacuum filtration. The solid filtered through the filter was thoroughly washed with water and cold methanol, and then vacuum filtration was performed to obtain the solid compound FF (29.04 g, 81%).

[0237] 13. Synthesis of Compound GG

[0238] [Reaction Equation 13]

[0239]

[0240] A solution (Ethoxyethanol:distilled water = 90 mL:30 mL) mixed with compound G (3.38 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask under a nitrogen atmosphere and stirred under reflux for 24 hours. After the reaction was finished, the temperature was lowered to room temperature and the resulting solid was separated by vacuum filtration. The solid filtered through the filter was thoroughly washed with water and cold methanol, and then vacuum filtration was performed to obtain solid compound GG (21.66 g, 96%).

[0241] 14. Synthesis of Compound A'

[0242] [Reaction Equation 14]

[0243]

[0244] Compound AA (6.88 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain solid compound A' (3.98 g, 94%).

[0245] 15. Synthesis of Compound B'

[0246] [Reaction Equation 15]

[0247]

[0248] Compound BB (7.11 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain solid compound B' (4.09 g, 96%).

[0249] 16. Synthesis of Compound C'

[0250] [Reaction Equation 16]

[0251]

[0252] Compound CC (7.78 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain solid compound C' (4.19 g, 91%).

[0253] 17. Synthesis of Compound D'

[0254] [Reaction Equation 17]

[0255]

[0256] Compound DD (7.15 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain solid compound D' (3.73 g, 87%).

[0257] 18. Synthesis of Compound E'

[0258] [Reaction Equation 18]

[0259]

[0260] Compound EE (7.12 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain solid compound E' (3.85 g, 90%).

[0261] 19. Synthesis of Compound F'

[0262] [Reaction Equation 19]

[0263]

[0264] Compound FF (7.17 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain solid compound F' (4.00 g, 93%).

[0265] 20. Synthesis of Compound G'

[0266] [Reaction Equation 20]

[0267]

[0268] Compound GG (4.51 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain solid compound G' (2.88 g, 97%).

[0269] [Synthesis of Organometallic Compounds]

[0270] 21. Synthesis of Compound 16

[0271] [Reaction Equation 21]

[0272]

[0273] G' (2.23 g, 3 mmol) and A (1.11 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under conditions of ethylene acetate:hexane = 25:75 to obtain compound 16 (2.16 g, 85%).

[0274] 22. Synthesis of Compound 17

[0275] [Reaction Equation 22]

[0276]

[0277] G' (2.23 g, 3 mmol) and B (1.16 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under conditions of ethylene acetate:hexane = 25:75 to obtain compound 17 (2.27 g, 88%).

[0278] 23. Synthesis of Compound 64

[0279] [Reaction Equation 23]

[0280]

[0281] G' (2.23 g, 3 mmol) and C (1.31 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under conditions of ethylene acetate:hexane = 25:75 to obtain compound 64 (2.22 g, 82%).

[0282] 24. Synthesis of Compound 136

[0283] [Reaction Equation 24]

[0284]

[0285] G' (2.23 g, 3 mmol) and D (1.17 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under conditions of ethylene acetate:hexane = 25:75 to obtain compound 136 (2.25 g, 87%).

[0286] 25. Synthesis of Compound 220

[0287] [Reaction Equation 25]

[0288]

[0289] G' (2.23 g, 3 mmol) and E (1.16 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by reducing the pressure of the filtrate obtained by filtration was purified by column chromatography under conditions of ethylene acetate:hexane = 25:75 to obtain compound 220 (2.14 g, 83%).

[0290] 26. Synthesis of Compound 225

[0291] [Reaction Equation 26]

[0292]

[0293] G' (2.23 g, 3 mmol) and F (1.17 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under conditions of ethylene acetate:hexane = 25:75 to obtain compound 225 (2.07 g, 80%).

[0294] 27. Synthesis of Compound 271

[0295] [Reaction Equation 27]

[0296]

[0297] A' (3.11 g, 3 mmol) and G (0.59 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under toluene:hexane = 1:1 conditions to obtain compound 271 (2.44 g, 82%).

[0298] 28. Synthesis of Compound 276

[0299] [Reaction Equation 28]

[0300]

[0301] Under a nitrogen atmosphere, B' (3.20 g, 3 mmol) and G (0.59 g, 3.5 mmol) were placed in a 150 mL round-bottom flask in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under conditions of toluene:hexane = 1:1 to obtain compound 276 (2.60 g, 85%).

[0302] 29. Synthesis of Compound 274

[0303] [Reaction Equation 29]

[0304]

[0305] Under a nitrogen atmosphere, C' (3.45 g, 3 mmol) and G (0.59 g, 3.5 mmol) were placed in a 150 mL round-bottom flask in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under conditions of toluene:hexane = 1:1 to obtain compound 274 (2.59 g, 78%).

[0306] 30. Synthesis of Compound 292

[0307] [Reaction Equation 30]

[0308]

[0309] D' (3.22 g, 3 mmol) and G (0.59 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under conditions of toluene:hexane = 1:1 to obtain compound 292 (2.50 g, 81%).

[0310] 31. Synthesis of Compound 284

[0311] [Reaction Equation 31]

[0312]

[0313] E' (3.20 g, 3 mmol) and G (0.59 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under toluene:hexane = 1:1 conditions to obtain compound 284 (2.73 g, 89%).

[0314] 32. Synthesis of Compound 279

[0315] [Reaction Equation 32]

[0316]

[0317] F' (3.22 g, 3 mmol) and G (0.59 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under conditions of toluene:hexane = 1:1 to obtain compound 279 (2.69 g, 87%).

[0318] 33. Synthesis of Compound 331

[0319] [Reaction Equation 33]

[0320]

[0321] Under a nitrogen atmosphere, A' (3.11 g, 3 mmol) and A (1.11 g, 3.5 mmol) were placed in a 150 mL round-bottom flask in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 48 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under toluene:hexane = 1:1 conditions to obtain compound 331 (2.67 g, 78%).

[0322] 34. Synthesis of Compound 336

[0323] [Reaction Equation 34]

[0324]

[0325] Under a nitrogen atmosphere, B' (3.20 g, 3 mmol) and B (1.16 g, 3.5 mmol) were placed in a 150 mL round-bottom flask in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 48 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under conditions of toluene:hexane = 1:1 to obtain compound 336 (3.02 g, 85%).

[0326] 35. Synthesis of Compound 334

[0327] [Reaction Equation 35]

[0328]

[0329] Under a nitrogen atmosphere, C' (3.45 g, 3 mmol) and C (1.31 g, 3.5 mmol) were placed in a 150 mL round-bottom flask in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 48 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under toluene:hexane = 1:1 conditions to obtain compound 334 (3.26 g, 83%).

[0330] 36. Synthesis of Compound 351

[0331] [Reaction Equation 36]

[0332]

[0333] D' (3.22 g, 3 mmol) and D (1.17 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 48 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under toluene:hexane = 1:1 conditions to obtain compound 351 (2.90 g, 81%).

[0334] 37. Synthesis of Compound 341

[0335] [Reaction Equation 37]

[0336]

[0337] E' (3.20 g, 3 mmol) and E (1.16 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 48 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under toluene:hexane = 1:1 conditions to obtain compound 341 (2.99 g, 84%).

[0338] 38. Synthesis of Compound 386

[0339] [Reaction Equation 38]

[0340]

[0341] F' (3.22 g, 3 mmol) and F (1.17 g, 3.5 mmol) were placed in a 150 mL round-bottom flask under a nitrogen atmosphere in a mixed solvent (2-ethoxyethanol:DMF = 40 mL:40 mL) and stirred at 135 °C for 48 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while the water was removed by adding anhydrous magnesium sulfate. The crude product obtained by filtration was purified under reduced pressure using column chromatography under toluene:hexane = 1:1 conditions to obtain compound 386 (3.12 g, 87%).

[0343] FIG. 1 is a schematic circuit diagram of an organic light-emitting display device according to the present invention.

[0344] As illustrated in FIG. 1, in an organic light-emitting display device, gate wiring (GL), data wiring (DL), and power wiring (PL) are formed intersecting each other to define a pixel area (P). In the pixel area (P), a switching thin-film transistor (Ts), a driving thin-film transistor (Td), a storage capacitor (Cst), and an organic light-emitting diode (D) are formed. The pixel area (P) may include a red pixel area, a green pixel area, and a blue pixel area.

[0345] The switching thin-film transistor (Ts) is connected to the gate wiring (GL) and data wiring (DL), and the driving thin-film transistor (Td) and storage capacitor (Cst) are connected between the switching thin-film transistor (Ts) and the power wiring (PL). The organic light-emitting diode (D) is connected to the driving thin-film transistor (Td).

[0346] In this organic light-emitting display device, when the switching thin-film transistor (Ts) is turned on according to the gate signal applied to the gate wiring (GL), the data signal applied to the data wiring (DL) is applied to the gate electrode of the driving thin-film transistor (Td) and one electrode of the storage capacitor (Cst) through the switching thin-film transistor (Ts).

[0347] The driving thin-film transistor (Td) is turned on according to a data signal applied to the gate electrode, and as a result, a current proportional to the data signal flows from the power wiring (PL) through the driving thin-film transistor (Td) to the organic light-emitting diode (D), and the organic light-emitting diode (D) emits light with a brightness proportional to the current flowing through the driving thin-film transistor (Td).

[0348] At this time, the storage capacitor (Cst) is charged with a voltage proportional to the data signal so that the voltage of the gate electrode of the driving thin-film transistor (Td) is maintained constant during one frame.

[0349] Therefore, the organic light-emitting display device can display a desired image.

[0350] FIG. 2 is a schematic cross-sectional view of an organic light-emitting display device according to a first embodiment of the present invention.

[0351] As shown in FIG. 2, the organic light-emitting display device (100) includes a substrate (102), a driving thin-film transistor (Td) disposed on the substrate (120), and an organic light-emitting diode (D1) connected to the driving thin-film transistor (Td).

[0352] For example, a red pixel area, a green pixel area, and a blue pixel area are defined on the substrate (102), and an organic light-emitting diode (D1) may be located at each pixel. That is, an organic light-emitting diode (D1) that emits red, green, and blue light is provided in the red pixel area, the green pixel area, and the blue pixel area.

[0353] The substrate (102) may be a glass substrate or a flexible substrate. For example, the substrate (102) may be any one of a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylenenaphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, and a polycarbonate (PC) substrate.

[0354] A first buffer layer (104) is formed on a substrate (102), and a light shielding pattern (105) is formed on the first buffer layer (104) in correspondence with a driving thin-film transistor (Td). Additionally, a second buffer layer (106) is formed on the light shielding pattern (105), and a buffer contact hole (107) that exposes the light shielding pattern (105) is formed on the second buffer layer (106).

[0355] For example, each of the first and second buffer layers (104, 106) may be made of an inorganic insulating material such as silicon oxide or silicon nitride, and the light-blocking pattern (105) may be made of an opaque metallic material. The first and second buffer layers (104, 106) and the light-blocking pattern (105) may be omitted.

[0356] On the second buffer layer (106), a driving thin-film transistor (Td) comprising a semiconductor layer (110), a gate electrode (130), a source electrode (152), and a drain electrode (154), and a storage capacitor (Cst) comprising first to third storage electrodes (112, 132, 156) are formed.

[0357] The semiconductor layer (110) and the first storage electrode (112) are formed on the second buffer layer (106). For example, the semiconductor layer (110) may be made of polycrystalline silicon, and impurities are doped into both edges of the semiconductor layer (110). One end of the semiconductor layer (110), that is, the end of the semiconductor layer (110) on the side of the drain electrode (154), is connected to the light-blocking pattern (105) through the buffer contact hole (107). In addition, the first storage electrode (112) is used as an electrode of the storage capacitor (Cst) by doping impurities into polycrystalline silicon. Meanwhile, the semiconductor layer (110) may be made of an oxide semiconductor material.

[0358] A gate insulating film (120) made of an insulating material is formed on the front surface of the substrate (102) on the semiconductor layer (110) and the first storage electrode (112). The gate insulating film (120) may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

[0359] A gate electrode (130) made of a conductive material such as metal is formed on the gate insulating film (120) in correspondence with the center of the semiconductor layer (110). In FIG. 2, the gate insulating film (120) is formed on the front surface of the substrate (102), but the gate insulating film (120) may be patterned in the same shape as the gate electrode (130).

[0360] In addition, a second storage electrode (132) is formed with the same material on the same layer as the gate electrode (130) in correspondence with the first storage electrode (112).

[0361] An interlayer insulating film (140) made of an insulating material is formed on the front surface of the substrate (102) on the gate electrode (130) and the second storage electrode (132). The interlayer insulating film (140) may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or may be formed of an organic insulating material such as benzocyclobutene or photoacryl.

[0362] The interlayer insulating film (140) has first and second semiconductor layer contact holes (142, 144) that expose the upper surfaces of both sides of the semiconductor layer (110). The first and second semiconductor layer contact holes (142, 144) are located on both sides of the gate electrode (130) and spaced apart from the gate electrode (130). In FIG. 2, the first and second semiconductor layer contact holes (142, 144) are shown as also being formed within the gate insulating film (120). Alternatively, if the gate insulating film (120) is patterned in the same shape as the gate electrode (130), the first and second semiconductor layer contact holes (142, 144) are formed only within the interlayer insulating film (140).

[0363] A source electrode (152) and a drain electrode (154) made of a conductive material such as metal are formed on the interlayer insulating film (140). The source electrode (152) and the drain electrode (154) are spaced apart from the gate electrode (130) and contact both sides of the semiconductor layer (110) through the first and second semiconductor layer contact holes (142, 144), respectively.

[0364] In addition, a third storage electrode (156) is formed on the interlayer insulating film (140) that overlaps with the second storage electrode (132).

[0365] As described above, the semiconductor layer (110), gate electrode (130), source electrode (152) and drain electrode (154) form a driving thin-film transistor (Td), and the first to third storage electrodes (112, 132, 156) and the dielectric layer, gate insulating film (120) and interlayer insulating film (140), form a storage capacitor (Cst).

[0366] In FIG. 2, the driving thin-film transistor (Td) has a coplanar structure in which the gate electrode (130), source electrode (152), and drain electrode (154) are located on the upper part of the semiconductor layer (110). Alternatively, the driving thin-film transistor (Td) may have an inverted staggered structure in which the gate electrode is located on the lower part of the semiconductor layer and the source electrode and drain electrode are located on the upper part of the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon.

[0367] Although not shown in FIG. 2, a gate wiring (GL, see FIG. 1) and a data wiring (DL, see FIG. 1) intersect each other to define a pixel area, and a switching thin-film transistor (Ts, see FIG. 1) connected to the gate wiring and the data wiring is further formed. The switching thin-film transistor (Ts) is connected to a driving thin-film transistor (Td). Additionally, a power wiring (PL, see FIG. 1) is formed spaced apart from the data wiring (DL) and may further be configured to maintain a constant voltage of the gate electrode (130) of the driving thin-film transistor (Td) during one frame.

[0368] A protective layer (160) is formed on the front surface of the substrate (102) covering the driving thin-film transistor (Td) on the source electrode (152), drain electrode (154), and third storage electrode (156). The protective layer (160) has a flat upper surface and has a drain contact hole (162) that exposes the drain electrode (154) of the driving thin-film transistor (Td).

[0369] The organic light-emitting diode (D1) includes a first electrode (210) located on a protective layer (160) and connected to the drain electrode (154) of a driving thin-film transistor (Td), an organic light-emitting layer (230) and a second electrode (220) sequentially stacked on the first electrode (210).

[0370] The first electrode (210) is formed separately for each pixel area. The first electrode (210) may be an anode and may be made of a conductive material with a relatively large work function value. For example, the first electrode (210) may include a transparent conductive oxide (TCO) layer. Specifically, the first electrode (210) may be made of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zinc-oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO), and aluminum:zinc oxide (Al:ZnO; AZO).

[0371] Meanwhile, if the organic light-emitting display device (100) of the present invention is of the top-emission type, the first electrode (210) may further include a reflective layer. For example, the reflective layer may be made of silver (Ag) or an aluminum-palladium-copper (APC) alloy. For example, the first electrode (210) may have a triple-layer structure of ITO / APC / ITO or a triple-layer structure of ITO / Ag / ITO.

[0372] Additionally, a bank layer (164) covering the edge of the first electrode (210) is formed on the protective layer (160). The bank layer (164) exposes the center of the first electrode (210) corresponding to the pixel area.

[0373] An organic light-emitting layer (230) is formed on the first electrode (210). The organic light-emitting layer (230) may have a single-layer structure of an emitting material layer (EML). Alternatively, the organic light-emitting layer (230) may have a multi-layer structure including at least one additionally a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL).

[0374] In the green pixel area, the organic light-emitting layer (230) of the organic light-emitting diode (D1) comprises the organic metal compound of the present invention, and accordingly, the light-emitting efficiency and light-emitting lifespan of the organic light-emitting diode (D1) and the organic light-emitting display device (1000) are greatly improved.

[0375] A second electrode (220) is formed on the upper surface of a substrate (102) on which an organic light-emitting layer (230) is formed. The second electrode (220) is located on the front surface of the display area and may be a cathode that injects electrons, made of a conductive material with a relatively small work function value. For example, the second electrode (220) may be made of aluminum (Al), magnesium (Mg), silver (Ag), or an alloy thereof, for example, an aluminum-magnesium alloy (AlMg) or a silver-magnesium alloy (MgAg). When the organic light-emitting display device (100) is of the top-emitting type, the second electrode (229) has a thin thickness and has light-transmitting (semi-transmitting) characteristics.

[0376] That is, one of the first electrode (210) and the second electrode (220) is a transmissive (semi-transmissive) electrode, and the other of the first electrode (210) and the second electrode (220) is a reflective electrode.

[0377] On the second electrode (220), an encapsulation layer (170) and a barrier layer (180, or a barrier substrate) are sequentially formed to prevent external moisture from penetrating into the organic light-emitting diode (D1).

[0378] Although not illustrated, the organic light-emitting display device (100) may further include a color filter layer (not illustrated). The color filter layer may include a red color filter, a green color filter, and a blue color filter corresponding to each of the red pixel area, the green pixel area, and the blue pixel area. When the organic light-emitting display device (100) includes a color filter layer, the color purity of the organic light-emitting display device (100) may be improved.

[0379] The organic light-emitting display device (100) may further include a polarizing plate (not shown) to reduce the reflection of external light. For example, the polarizing plate (not shown) may be a circular polarizing plate. If the organic light-emitting display device (100) is a bottom-emitting type, the polarizing plate may be located below the substrate (102). Meanwhile, if the organic light-emitting display device (100) of the present invention is a top-emitting type, the polarizing plate may be located above the barrier layer (180).

[0380] FIG. 3 is a schematic cross-sectional view of an organic light-emitting diode in a second embodiment of the present invention.

[0381] As illustrated in FIG. 3, the organic light-emitting diode (D1) of the present invention comprises a first electrode (210) and a second electrode (220) facing each other, and an organic light-emitting layer (230) located between the first and second electrodes (210, 220). The organic light-emitting diode (D) of FIG. 3 is located in a green pixel area.

[0382] The first electrode (210) may be an anode, and the second electrode (220) may be a cathode. For example, the first electrode (310) and the second electrode (320) may each have a thickness of 30 to 300 nm.

[0383] The organic light-emitting layer (230) includes an emitting material layer (EML, 360).

[0384] Additionally, the organic light-emitting layer (230) may further include at least one of a hole transporting layer (HTL, 350) located between the first electrode (310) and the emitting material layer (EML, 360), and an electron transporting layer (ETL, 370) located between the emitting material layer (EML, 360) and the second electrode (320).

[0385] Additionally, the organic light-emitting layer (230) may further include at least one of a hole injection layer (340) located between the first electrode (210) and the hole transport layer (350), and an electron injection layer (380) located between the second electrode (224) and the electron transport layer (370).

[0386] Additionally, the organic light-emitting layer (230) may further include at least one of an electron blocking layer (355) located between the hole transport layer (350) and the light-emitting material layer (360), and a hole blocking layer (375) located between the light-emitting material layer (360) and the electron transport layer (370).

[0387] That is, the organic light-emitting diode (D1) according to the second embodiment of the present invention has a single light-emitting unit.

[0388] The hole injection layer (340) is located between the first electrode (210) and the hole transport layer (350), and improves the interface characteristics between the first electrode (310), which is an inorganic material, and the hole transport layer (350), which is an organic material. For example, the hole injection layer (340) is 4,4',4"-tris(3-methylphenylamino)triphenylamine (4,4',4"-tris(3-methylphenylamino)triphenylamine; MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (4,4',4"-tris(N,N-diphenyl-amino)triphenylamine; NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine; 1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazoyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPB or NPD), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrene sulfonate;It may include a hole injection material that is any one of PEDOT / PSS), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, and N,N'-diphenyl-N,N'-di[4-(N,N-diphenyl-amino)phenyl]benzidine (NPNPB). For example, the hole injection layer (340) may include a compound of the following chemical formula 4. The hole injection layer (340) may have a thickness of 20 to 120 nm, preferably 40 to 80 nm.;

[0389] The hole transport layer (350) is located between the first electrode (310) and the light-emitting material layer (360) adjacent to the light-emitting material layer (360), for example, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), Poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine](poly[N,N'-bis(4-butylpnehyl)-N,N'-bis(phenyl)-benzidine]; Poly-TPD), Poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))](poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))], TFB), Di-[4-(N,N-di-p-tolyl-amino)phenyl]cyclohexane(di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane; TAPC), 3,5-di(9H-carbazol-9-yl)-N,N-diphenylaniline;DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine), N-(biphenyl]-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl)-4-amine(N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine), It may include, but is not limited to, any one of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine. The hole transport layer (350) may each have a thickness of 30 nm to 150 nm, preferably 50 nm to 120 nm. For example, the thickness of the hole transport layer (350) may be greater than the thickness of the hole injection layer (340).

[0390] The light-emitting material layer (360) includes a first compound, which is an organometallic compound of the present invention, as a dopant (light-emitting body, 362). Additionally, the light-emitting material layer (360) may further include a second compound as a host (not shown).

[0391] The light-emitting material layer (360) may have a thickness of 10 to 100 nm, preferably 20 to 50 nm. Additionally, the dopant (362) may have 1 to 20 weight%, preferably 1 to 10 weight%, in the light-emitting material layer (360).

[0392] For example, the host of the luminescent material layer (360) is 9-(3-(9H-carbazol-9-yl)phenyl)-9H-carbazole-3-carbonitrile (mCP-CN), CBP, 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), 1,3-bis(carbazol-9-yl)benzene (mCP), DPEPO, 2,8-bis(diphenylphosphoryl)dibenzothiophene (PPT), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene (1,3,5-Tri[(3-pyridyl)-phen-3-yl]benzene; TmPyPB), 2,6-di(9H-carbazol-9-yl)pyridine (2,6-Di(9H-carbazol-9-yl)pyridine; PYD-2Cz), 2,8-di(9H-carbazol-9-yl)dibenzothiophene (2,8-di(9H-carbazol-9-yl)dibenzothiophene; DCzDBT), 3',5'-di(carbazol-9-yl)-[1,1'-biphenyl]-3,5-dicarbonitrile (3',5'-Di(carbazol-9-yl)-[1,1'-bipheyl]-3,5-dicarbonitrile; DCzTPA), 4'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile(4'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile(pCzB-2CN), 3'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile(3'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile(mCzB-2CN), TSPO1, 9-(9-phenyl-9H-carbazol-6-yl)-9H-carbazole(9-(9-phenyl-9H-carbazol-6-yl)-9H-carbazole;CCP), 4-(3-(triphenylen-2-yl)phenyl)dibenzo[b,d]thiophene(4-(3-(triphenylen-2-yl)phenyl)dibenzo[b,d]thiophene), 9-(4-(9H-carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole(9-(4-(9H-carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole), 9-(3-(9H-carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole(9-(3-(9H-carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole), 9-(6-(9H-carbazol-9-yl)pyridin-3-yl)-9H-3,9'-bicabazole), 9,9'-Diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 1,3,5-Tris(carbazole-9-yl)benzene (TCP), TCTA, 4,4'-Bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), It may be any one of 2,7-Bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-Tetrakis(carbazole-9-yl)-9,9-spiorofluorene (Spiro-CBP), and 3,6-Bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCz1), but is not limited thereto.

[0393] The electron transport layer (370) located between the light-emitting material layer (360) and the second electrode (220) is made of tris-(8-hydroxyquinoline)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tertiary-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate (Liq), and 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi). Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline; BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (3-(4-Biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole; NTAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole; NTAZ), 1,3,5-tri(p-pyrid-3-yl-phenyl)benzene (1,3,5-Tri(p-pyrid-3-yl-phenyl)benzene;TpPyPB), 2,4,6-Tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine(2,4,6-Tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine; TmPPPyTz), Poly[(9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene)-alt-2,7-(9,9-dioctylfluorene)](Poly[9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)]; PFNBr), Tris(phenylquinoxaline)(tris(phenylquinoxaline; TPQ), It may include an electron transport material that is one of diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), 2-[4-(9,10-di-naphthalen-2-yl-anthracen-2-yl)phenyl]-1-phenyl-1H-benzimidazole (ZADN), and combinations thereof. For example, the electron transport layer (370) may include a compound of Formula 7.;

[0394] The electron injection layer (380) is located between the second electrode (320) and the electron transport layer (370) and may include an electron injection material which is, for example, LiF, CsF, NaF, BaF2, Liq (lithium quinolate), lithium benzoate, or sodium stearate.

[0395] Alternatively, the electron injection layer (380) may be omitted by forming an electron transport layer (370) by co-depositing the electron transport material of Formula 7 and the electron injection material (Liq). At this time, the electron transport layer (370) may have a thickness of 10 to 60 nm, preferably 20 to 40 nm.

[0396] The organometallic compound of the present invention is an iridium complex comprising a first ligand having a structure comprising a pyridine moiety and a condensed ring moiety connected thereto containing oxygen, wherein an alkylsilyl group is bonded to a specific position of the condensed ring moiety, and a second ligand comprising a benzene moiety and a pyridine moiety connected thereto, wherein an alkylsilyl group is bonded to a specific position of the condensed ring moiety. Accordingly, the luminous efficiency and lifespan of an organic light-emitting diode (D1) and an organic light-emitting display device (100) comprising the organometallic compound are improved.

[0397] In addition, at least one of the hydrogens of the pyridine moiety of the second ligand is substituted with a non-oxidized C1 to C10 alkyl group, thereby further improving the luminous efficiency and lifespan of the organic light-emitting diode (D1) and organic light-emitting display device (100) containing the organometallic compound.

[0398] In addition, at least one of the hydrogens of the pyridine moiety of the first ligand is substituted with one of an unsubstituted or deuterium-substituted C1 to C10 alkyl group or an unsubstituted C1 to C10 cycloalkyl group, thereby further improving the luminous efficiency and lifespan of the organic light-emitting diode (D1) and organic light-emitting display device (100) containing the organometallic compound.

[0399] [Organic Light Emitting Diode]

[0400] On a glass substrate coated with an anode (ITO, 100 nm), a hole injection layer (Chemical Formula 4, 60 nm), a hole transport layer (Chemical Formula 5, 80 nm), a light-emitting material layer (host (Chemical Formula 6), dopant, 30 nm), an electron transport layer (Chemical Formula 7:Liq(1:1), 30 nm), and a cathode (Al, 100 nm) were sequentially deposited.

[0401] [Chemical Formula 4]

[0402]

[0403] [Chemical Formula 5]

[0404]

[0405] [Chemical Formula 6]

[0406]

[0407] [Chemical Formula 7]

[0408]

[0409] 1. Comparative Examples 1 to 13 (Ref1~Ref13)

[0410] Compounds Ref-1 to Ref-13 of Chemical Formula 8 were used as dopants.

[0411] 2. Experimental Examples 1 to 32 (Ex1~Ex33)

[0412] Organometallic compounds of Chemical Formula 3 (Compound 271, Compound 292, Compound 276, Compound 279, Compound 284, Compound 336, Compound 331, Compound 334, Compound 351, Compound 386, Compound 16, Compound 17, Compound 64, Compound 136, Compound 225, Compound 220, Compounds 391–405, Compound 20, Compound 62) were used as dopants.

[0413] [Chemical Formula 8]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419] The characteristics of the organic light-emitting diodes fabricated in Comparative Examples 1 to 13 and Experimental Examples 1 to 31 (driving voltage, maximum luminous quantum efficiency (Emax), external quantum efficiency (EQE), and lifetime (LT95, %)) were measured and listed in Tables 1 to 4. (The maximum luminous efficiency, external quantum efficiency, and lifetime are relative values ​​with respect to Comparative Example 1.)

[0420] [Table 1]

[0421]

[0422] [Table 2]

[0423]

[0424] [Table 3]

[0425]

[0426] [Table 4]

[0427]

[0428] As shown in Tables 1 to 4, the luminous efficiency and lifespan of the organic light-emitting diodes of Experimental Examples 1 to 33 are increased compared to the organic light-emitting diodes of Comparative Examples 1 to 13. For example, compounds Ref-2 to Ref-13 of Formula 8 and compounds 16, 17, 64, 136, and 391 to 398 of Formula 3 each differ in the bonding position of the alkylsilyl group (trimethylsilyl group), and the organic light-emitting diodes of Experimental Examples 11 to 14, 17, 18, 25 to 28, 30, and 31 using the organometallic compounds of the present invention have high luminous efficiency and lifespan.

[0429] Meanwhile, for example, compounds 220, 225, and 284 of Chemical Formula 3 contain nitrogen within the oxygen-containing condensation ring moiety, whereas compounds 17, 136, and 276 of Chemical Formula 3 do not contain nitrogen within the oxygen-containing condensation ring moiety. In this case, compared to the organic light-emitting diodes of Experimental Examples 16, 15, and 5 using compounds 220, 225, and 284 of Chemical Formula 3, the luminous efficiency and lifespan of the organic light-emitting diodes of Experimental Examples 12, 14, and 3 using compounds 17, 136, and 276 of Chemical Formula 3 are improved. That is, in Chemical Formula 1, Chemical Formula 2-1, Chemical Formula 2-2, and Chemical Formula 2-3, X1 to X5 may be CR5.

[0430] In addition, for example, compounds 271, 276, 292, and 292 of Formula 3 and compounds 16, 17, and 136 of Formula 3 each differ in the number of first and second ligands, and compared to the organic light-emitting diodes of Experimental Examples 1, 3, and 2 using compounds 271, 276, 292, and 292 of Formula 3, the luminous efficiency and lifetime of the organic light-emitting diodes of Experimental Examples 11, 12, and 14 using compounds 16, 17, and 136 of Formula 3 are improved. That is, in Formula 1, Formula 2-1, Formula 2-2, and Formula 2-3, n can be 2.

[0431] In addition, compounds 17 and 20 differ from compounds 62 and 64, respectively, only in the position of the alkyl group bonded to the pyridine moiety of the first ligand, and the luminous efficiency and / or lifetime of the organic light-emitting diodes of Experimental Example 12 and Experimental Example 32 using compounds 17 and 20 are further improved.

[0433] FIG. 4 is a schematic cross-sectional view of an organic light-emitting display device according to a third embodiment of the present invention.

[0434] As illustrated in FIG. 4, an organic light-emitting display device (400) according to the third embodiment of the present invention comprises a first substrate (402) in which a red pixel (RP), a green pixel (GP), and a blue pixel (BP) are each defined, a second substrate (404) facing the first substrate (402), an organic light-emitting diode (D2) located between the first substrate (402) and the second substrate (404) and emitting white light, and a color filter layer (480) located between the organic light-emitting diode (D2) and the second substrate (404).

[0435] The first substrate (402) and the second substrate (404) may each be a glass substrate or a plastic substrate. For example, the first and second substrates (402, 404) may each be any one of a PI substrate, a PES substrate, a PEN substrate, a PET substrate, and a PC substrate.

[0436] A buffer layer (406) is formed on the first substrate (402), and a thin-film transistor (Tr) is formed on the buffer layer (406) corresponding to each of the red pixel region (RP), the green pixel region (GP), and the blue pixel region (BP). The buffer layer (406) may be omitted. The thin-film transistor (Tr) may be a driving thin-film transistor.

[0437] A semiconductor layer (410) is formed on the buffer layer (406). For example, the semiconductor layer (410) may be made of an oxide semiconductor material or polycrystalline silicon.

[0438] A gate insulating film (420) made of an insulating material, such as silicon oxide or silicon nitride, is formed on the upper part of the semiconductor layer (410).

[0439] A gate electrode (430) made of a conductive material such as metal is formed on the upper part of the gate insulating film (420) in correspondence with the center of the semiconductor layer (410).

[0440] An interlayer insulating film (440) is formed on the upper part of the gate electrode (430), the insulating material being an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photoacryl.

[0441] The interlayer insulating film (440) has first and second semiconductor layer contact holes (442, 444) that expose the upper surfaces of both sides of the semiconductor layer (410). The first and second semiconductor layer contact holes (442, 444) are located spaced apart from the gate electrode (430) on both sides of the gate electrode (430).

[0442] On the upper part of the interlayer insulating film (440), a source electrode (452) and a drain electrode (454) made of a conductive material such as metal are formed. The source electrode (452) and the drain electrode (454) are spaced apart from the gate electrode (430) and contact both sides of the semiconductor layer (410) through the first and second semiconductor layer contact holes (442, 444), respectively.

[0443] The semiconductor layer (410), gate electrode (430), source electrode (452) and drain electrode (454) form a thin-film transistor (Tr).

[0444] A protective layer (460) is formed on the front surface of the first substrate (402) and covers the thin-film transistor (Tr) on the upper portion of the source electrode (452) and the drain electrode (454). The protective layer (460) has a drain contact hole (462) that exposes the drain electrode (454) of the thin-film transistor (Tr).

[0445] An organic light-emitting diode (D2) is positioned on a protective layer (460). The organic light-emitting diode (D2) includes a first electrode (510) connected to the drain electrode (452) of a thin-film transistor (Tr), a second electrode (520) facing the first electrode (510), and an organic light-emitting layer (530) positioned between the first and second electrodes (510, 520).

[0446] The first electrode (510) is positioned separately for each pixel area and may be an anode. The first electrode (510) includes a transparent conductive oxide layer.

[0447] A bank layer (464) covering the edge of the first electrode (510) is formed on the protective layer (460). The bank layer (464) exposes the center of the first electrode (510) corresponding to the pixel regions (RP, GP, BP). Since the organic light-emitting diode (D2) emits white light in the red, green, and blue pixel regions (Rp, GP, BP), the light-emitting layer (530) can be formed as a common layer without needing to be separated from the red, green, and blue pixel regions (Rp, GP, BP). The bank layer (464) is formed to prevent current leakage at the edge of the first electrode (510), and the bank layer (464) may be omitted.

[0448] The organic light-emitting layer (530) is formed on the first electrode (510) and includes multiple light-emitting units as described below. That is, the organic light-emitting diode (D2) has a tandem structure. For example, as shown in FIGS. 5 to 8, the organic light-emitting layer (530) may include a plurality of light-emitting units (630, 730, 730A, 830, 930, 930A, 1030, 1030A) and one or more charge-generating layers (690, 890, 990). Each light-emitting unit includes a light-emitting material layer, and the charge-generating layer is located between adjacent light-emitting units.

[0449] A second electrode (520) is formed on the upper surface of the first substrate (402) on which the organic light-emitting layer (530) is formed. The second electrode (520) is located on the front surface of the display area and may be a cathode.

[0450] In the organic light-emitting display device (400), light emitted from the organic light-emitting layer (530) is incident on the color filter layer (480) through the second electrode (520), so the second electrode (520) has a thin thickness so that light can be transmitted. In addition, a reflective layer may be located below the first electrode (510).

[0451] The color filter layer (480) is located on top of the organic light-emitting diode (D2) and includes a red color filter (482), a green color filter (484), and a blue color filter (486) corresponding to each of the red pixel area (RP), the green pixel area (GP), and the blue pixel area (BP). The red color filter (482) may include at least one of a red dye and a red pigment, the green color filter (484) may include at least one of a green dye and a green pigment, and the blue color filter (486) may include at least one of a blue dye and a blue pigment.

[0452] Although not illustrated, the color filter layer (480) may be attached to the organic light-emitting diode (D2) by an adhesive layer. Alternatively, the color filter layer (480) may be formed directly on the organic light-emitting diode (D2).

[0453] In FIG. 4, light emitted from the organic light-emitting layer (530) passes through the second electrode (520), and the color filter layer (480) is placed on top of the organic light-emitting diode (D2). Alternatively, the light from the organic light-emitting layer (530) may pass through the first electrode (510), and the color filter layer (480) may be placed between the organic light-emitting diode (D2) and the first substrate (402).

[0454] Additionally, a color conversion layer (not shown) may be provided between the organic light-emitting diode (D2) and the color filter layer (480). The color conversion layer includes a red color conversion layer, a green color conversion layer, and a blue color conversion layer corresponding to each pixel area, and can convert white light emitted from the organic light-emitting diode (D2) into red, green, and blue, respectively.

[0455] As described above, white light emitted from the organic light-emitting diode (D2) passes through the red color filter (482), green color filter (484), and blue color filter (486) corresponding to the red pixel area (RP), green pixel area (GP), and blue pixel area (BP), respectively, thereby displaying red, green, and blue light in the red pixel (RP), green pixel (GP), and blue pixel (BP).

[0456] FIG. 5 is a schematic cross-sectional view of an organic light-emitting diode in the fourth embodiment of the present invention.

[0457] As illustrated in FIG. 5, an organic light-emitting diode (D2) according to the fourth embodiment of the present invention comprises a first electrode (610) and a second electrode (620) facing each other, a first light-emitting unit (630) located between the first electrode (610) and the second electrode (620), a second light-emitting unit (730) located between the first light-emitting unit (630) and the second electrode (620), and a charge-generating layer (690) located between the first and second light-emitting units (630, 730).

[0458] The first electrode (610) may be an anode, and the second electrode (620) may be a cathode.

[0459] The first light-emitting unit (630) includes a first light-emitting material layer (660). Additionally, the first light-emitting unit (630) may further include at least one of a first hole transport layer (lower hole transport layer, 650) below the first light-emitting material layer (660) and a first electron transport layer (lower electron transport layer, 670) above the first light-emitting material layer (660). Additionally, the first light-emitting unit (630) may further include a hole injection layer (640) below the first hole transport layer (650). In this case, the hole injection layer (640) is located between the first electrode (610) and the first hole transport layer (650). Additionally, the first light-emitting unit (630) may further include at least one of a first electron blocking layer (lower electron blocking layer, 655) located between the first hole transport layer (650) and the first light-emitting material layer (660), and a first hole blocking layer (lower hole blocking layer, 675) located between the first light-emitting material layer (660) and the first electron transport layer (670).

[0460] The second light-emitting unit (730) includes a second light-emitting material layer (760). Additionally, the second light-emitting unit (730) may further include at least one of a second hole transport layer (upper hole transport layer, 750) below the second light-emitting material layer (760) and a second electron transport layer (upper electron transport layer, 770) above the second light-emitting material layer (760). Additionally, the second light-emitting unit (730) may further include an electron injection layer (780) above the second electron transport layer (770). In this case, the electron injection layer (780) is located between the second electrode (620) and the second electron transport layer (770). Additionally, the second light-emitting unit (730) may further include at least one of a second electron blocking layer (upper electron blocking layer, 755) located between the second hole transport layer (750) and the second light-emitting material layer (760), and a second hole blocking layer (upper hole blocking layer, 775) located between the second light-emitting material layer (760) and the second electron transport layer (770).

[0461] At this time, one of the first light-emitting material layer (660) and the second light-emitting material layer (760) may include an organometallic compound of the present invention and emit green (G) light. For example, the second light-emitting material layer (760) may include an organometallic compound of the present invention. In this case, the first light-emitting material layer (660) may emit red (R) light and / or blue (B) light. Thus, the organic light-emitting diode (600) can emit white (W) light.

[0462] A charge generation layer (CGL; 690) is located between the first light-emitting unit (630) and the second light-emitting unit (730). The charge generation layer (690) includes an N-type charge generation layer (N-CGL, 710) located adjacent to the first light-emitting unit (630) and a P-type charge generation layer (P-CGL, 720) located adjacent to the second light-emitting unit (730). The N-type charge generation layer (710) injects electrons into the first light-emitting unit (630), and the P-type charge generation layer (720) injects holes into the second light-emitting unit (730).

[0463] The second light-emitting material layer (760) comprises a first host (not shown) and a first dopant (766), and the first dopant (766) is an organometallic compound of the present invention. For example, the first host is mCP-CN, CBP, mCBP, mCP, DPEPO, PPT, TmPyPB, PYD-2Cz, DCzDBT, DCzTPA, pCzB-2CN, mCzB-2CN, TSPO1, CCP, 4-(3-(triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(6-(9H-carbazole-9-yl)pyridine-3-yl)-9H-3,9'-bicarbazole, BCzPh, TCP, TCTA, CDBP, DMFL-CBP, Spiro-CBP, TCz1 It could be any one of them.

[0464] The first dopant (762) may be doped into the second light-emitting material layer (760) in a ratio of 1 to 20 weight%, preferably 1 to 10 weight%. For example, the second light-emitting material layer (760) may have a thickness of 10 to 100 nm, preferably 20 to 50 nm.

[0465] The first light-emitting material layer (660) may be a blue (B) and / or red (R) light-emitting material layer. For example, the first light-emitting material layer (660) may include a blue light-emitting material layer and a red light-emitting material layer. In this case, the first light-emitting material layer (660) includes a lower light-emitting material layer (not shown) located between the first electron blocking layer (655) and the first hole blocking layer (675), and an upper light-emitting material layer (not shown) located between the lower light-emitting material layer and the first hole blocking layer (675), and either of the lower light-emitting material layer and the upper light-emitting material layer (not shown) may be a red light-emitting material layer and the other may be a blue light-emitting material layer.

[0466] For example, when the lower light-emitting material layer (not shown) is a red light-emitting material layer, the lower light-emitting material layer (not shown) may include a second host that is a red (R) host and a second dopant that is a red (R) dopant.

[0467] The second host, which is a red (R) host, may be any one of the aforementioned first host, bis(2-hydroxylphenyl)-pyridine)beryllium (Bepp2), bis(10-hydroxybenzo[h]quinolinato)beryllium (Bebq2), and 1,3,5-tris(1-pyrenyl)benzene (TPB3), but is not limited thereto.

[0468] Meanwhile, the second dopant that can be applied as a red (R) dopant may be an organometallic compound having the structure of the following chemical formula 9 or chemical formula 10, but is not limited thereto.

[0469] [Chemical Formula 9]

[0470]

[0471] [Chemical Formula 10]

[0472]

[0473] In chemical formulas 9 and 10, R 31 , R 32 , R 36 , R 37 Each independently consists of deuterium, a halogen atom, a C1–C6 alkyl group, a C3–C6 cycloalkyl group, and a C6–C 10 aryl group or C4~C 10 Selected from hetero-aryl groups, R 33 to R 35 and R 38 to R 40 Each is independently selected from hydrogen, deuterium, or C1-C6 alkyl groups. o and q are each independently integers from 0 to 4, and p and r are each independently integers from 0 to 6.

[0474] The upper light-emitting material layer (not shown) includes a third host and a third dopant which is a blue (B) dopant.

[0475] For example, the third host is mCP, mCP-CN, mCBP, CBP-CN, CBP, 9-(3-(9H-carbazol-9-yl)phenyl)-3-(diphenylphosphoryl)-9H-carbazole(9-(3-(9H-Carbazol-9-yl)phenyl)-3-(diphenylphosphoryl)-9H-carbazole, mCPPO1), 3,5-di(9H-carbazol-9-yl)biphenyl(3,5-Di(9H-carbazol-9-yl)biphenyl; Ph-mCP), TSPO1, 9-(3'-(9H-carbazol-9-yl-[1,1'-biphenyl]-3-yl)-9H-pyrido[2,3-b]indole(9-(3'-(9H- carbazol -9-yl)-[1,1'-biphenyl]-3-yl)-9H-pyrido[2,3-b]indole; It may be any one of CzBPCb), bis(2-methylphenyl)diphenylsilane (UGH-1), 1,4-bis(triphenylsilyl)benzene (UGH-2), 1,3-bis(triphenylsilyl)benzene (UGH-3), 9,9-spirobifluoren-2-yl-diphenyl-phosphine oxide (SPPO1), and 9,9'-(5-triphenylsilyl)-1,3-phenylene)bis(9H-carbazole) (9,9'-(5-(Triphenylsilyl)-1,3-phenylene)bis(9H-carbazole); SimCP), but is not limited thereto.

[0476] In addition, the third dopant, which is the blue (B) dopant, is perylene, 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (4,4'-Bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (4-(Di-p-tolylamino)-4-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (4,4'-Bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 2,5,8,11-tetra-tetr-butylperylene (TBPe), Bepp2, 9-(9-phenylcarbazole-3-yl)-10-(naphthalene-1-yl)anthracene (9-(9-Phenylcarbazole-3-yl)-10-(naphthalene-1-yl)anthracene (PCAN), mer-Tris(1-phenyl-3-methylimidazolin-2-ylidene-C,C(2)'iridium(Ⅲ)), mer-Ir(pmi)3), fac-Tris(1,3-diphenyl-benzimidazolin-2-ylidene-C,C(2)'iridium(Ⅲ), fac-Ir(dpbic)3), bis(3,4,5-trifluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(Ⅲ); Ir(tfpd)2pic), tris(2-(4,6-difluorophenyl)pyridine)iridium(Ⅲ); Ir(Fppy)3), bis[2-(4,6-difluorophenyl)pyridinato-C 2 ,N](Piccolinato)iridium(III)(Bis[2-(4,6-difluorophenyl)pyridinato-C2 It may be any one of [,N](picolinato)iridium(Ⅲ); FIrpic), but is not limited thereto.

[0477] For example, in each of the red and blue light-emitting material layers capable of forming the first light-emitting material layer (660), the second dopant or the third dopant may be doped in a ratio of 1 to 30 weight percent.

[0478] The organic light-emitting diode (D2) of the present invention has a tandem structure, and one of the light-emitting material layers (660, 760) includes the organic metal compound of the present invention. Accordingly, the organic light-emitting diode (D2) can achieve white light emission with improved light emission efficiency, color purity, and lifespan.

[0479] These organic light-emitting diodes (D2) can be used in an organic light-emitting display device (400 of FIG. 4) that includes a color filter layer (480) to realize a color image.

[0480] FIG. 6 is a schematic cross-sectional view of an organic light-emitting diode according to the fifth embodiment of the present invention.

[0481] As illustrated in FIG. 6, an organic light-emitting diode (D2) according to the fifth embodiment of the present invention comprises a first electrode (610) and a second electrode (620) facing each other, a first light-emitting unit (630A) located between the first electrode (610) and the second electrode (620), a second light-emitting unit (730A) located between the first light-emitting unit (630A) and the second electrode (420), and a charge-generating layer (690) located between the first and second light-emitting units (630A, 730A).

[0482] The first light-emitting unit (630A) includes a first light-emitting material layer (660A). Additionally, the first light-emitting unit (630A) may further include at least one of a first hole transport layer (650) below the first light-emitting material layer (660A) and a first electron transport layer (670) above the first light-emitting material layer (660A). Additionally, the first light-emitting unit (630A) may further include a hole injection layer (640) below the first hole transport layer (650). In this case, the hole injection layer (640) is located between the first electrode (610) and the first hole transport layer (650). Additionally, the first light-emitting unit (630A) may further include at least one of a first electron blocking layer (655) located between the first hole transport layer (650) and the first light-emitting material layer (660A), and a first hole blocking layer (675) located between the first light-emitting material layer (660A) and the first electron transport layer (670).

[0483] The second light-emitting unit (730A) includes a second light-emitting material layer (760A). Additionally, the second light-emitting unit (730A) may further include at least one of a second hole transport layer (750) below the second light-emitting material layer (760A) and a second electron transport layer (770) above the second light-emitting material layer (760A). Additionally, the second light-emitting unit (730A) may further include an electron injection layer (780) above the second electron transport layer (770). In this case, the electron injection layer (780) is located between the second electrode (620) and the second electron transport layer (770). Additionally, the second light-emitting unit (730A) may further include at least one of a second electron blocking layer (755) located between the second hole transport layer (750) and the second light-emitting material layer (760A), and a second hole blocking layer (775) located between the second light-emitting material layer (760A) and the second electron transport layer (770).

[0484] Additionally, the charge generating layer (690) located between the first and second light-emitting units (630A, 730A) includes an N-type charge generating layer (710) located adjacent to the first light-emitting unit (630) and a P-type charge generating layer (720) located adjacent to the second light-emitting unit (730A).

[0485] The organic light-emitting diode (D2) of FIG. 5 and the organic light-emitting diode (D2) of FIG. 6 differ in the first light-emitting material layer (660A) and the second light-emitting material layer (760A). Therefore, a detailed description of the remaining components, excluding the first and second light-emitting material layers (660A, 760A), is omitted.

[0486] The second light-emitting material layer (660A) includes a lower light-emitting material layer (762) located between the second electron blocking layer (655) and the second hole blocking layer (675), and an upper light-emitting material layer (764) located between the lower light-emitting material layer (762) and the second hole blocking layer (775). At this time, one of the upper and lower light-emitting material layers (762, 764) includes an organometallic compound of the present invention and emits green (G) light, and the other of the upper and lower light-emitting material layers (762, 764) emits red (R) light. For example, the lower light-emitting material layer (762) may include an organometallic compound of the present invention.

[0487] The lower light-emitting material layer (762) of the second light-emitting material layer (760A) includes a first host and a first dopant (768). The first host is one of mCP-CN, CBP, mCBP, mCP, DPEPO, PPT, TmPyPB, PYD-2Cz, DCzDBT, DCzTPA, pCzB-2CN, mCzB-2CN, TSPO1, CCP, 4-(3-(triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(6-(9H-carbazole-9-yl)pyridine-3-yl)-9H-3,9'-bicarbazole, BCzPh, TCP, TCTA, CDBP, DMFL-CBP, Spiro-CBP, TCz1 The first dopant (768) is an organometallic compound of the present invention.

[0488] The upper light-emitting material layer (764) of the second light-emitting material layer (760A) may include a second host and a second dopant which is a red dopant. For example, the second dopant may be an organometallic compound having the structure of Formula 9 or Formula 10.

[0489] The first dopant (768) may be doped into the lower light-emitting material layer (762) at a ratio of 1 to 20 weight%, preferably 1 to 10 weight%. For example, the lower light-emitting material layer (762) may have a thickness of 10 to 100 nm, preferably 20 to 50 nm.

[0490] The second dopant may be doped into the upper light-emitting material layer (764) at a ratio of 1 to 30 weight percent. The upper light-emitting material layer (764) may be formed with a thickness of 10 to 100 nm, preferably 10 to 50 nm, but the present invention is not limited thereto.

[0491] The first emitting material layer (660A) may be a blue (B) emitting material layer. The first emitting material layer (660A) may include a third host and a third dopant which is a blue (B) dopant. In the first emitting material layer (660A), the third dopant may be doped in a ratio of 1 to 30 weight%. For example, the first emitting material layer (660A) may be formed with a thickness of 10 to 200 nm, preferably 20 to 100 nm, more preferably 20 to 50 nm, but the present invention is not limited thereto.

[0492] As described above, the organic light-emitting diode (D2) has a tandem structure, and one of the light-emitting material layers includes the organic metal compound of the present invention. Accordingly, the organic light-emitting diode (D2) can achieve white light emission with improved light-emitting efficiency, color purity, and light-emitting lifetime.

[0493] These organic light-emitting diodes (D2) can be used in an organic light-emitting display device (400 of FIG. 4) that includes a color filter layer (480) to realize a color image.

[0494] FIG. 7 is a schematic cross-sectional view of an organic light-emitting diode according to the 6th embodiment of the present invention.

[0495] As illustrated in FIG. 7, an organic light-emitting diode (D2) according to the sixth embodiment of the present invention comprises a first electrode (810) and a second electrode (820) facing each other, a first light-emitting unit (830) located between the first electrode (810) and the second electrode (820), a second light-emitting unit (930) located between the first light-emitting unit (830) and the second electrode (820), a third light-emitting unit (1030) located between the second light-emitting unit (930) and the second electrode (820), a first charge-generating layer (890) located between the first and second light-emitting units (830, 930), and a second charge-generating layer (990) located between the second and third light-emitting units (930, 1030).

[0496] The first electrode (810) may be an anode, and the second electrode (820) may be a cathode.

[0497] The first light-emitting unit (830) includes a hole injection layer (840), a first hole transport layer (850), a first light-emitting material layer (860), and a first electron transport layer (870) that are sequentially stacked. Additionally, the first light-emitting unit (830) may further include at least one of a first electron blocking layer (855) located between the first hole transport layer (850) and the first light-emitting material layer (860), and a first hole blocking layer (875) located between the first light-emitting material layer (860) and the first electron transport layer (870).

[0498] The second light-emitting unit (930) includes a second hole transport layer (950), a second light-emitting material layer (960), and a second electron transport layer (970) that are sequentially stacked. Additionally, the second light-emitting unit (930) may further include at least one of a second electron blocking layer (955) located between the second hole transport layer (950) and the second light-emitting material layer (960), and a second hole blocking layer (975) located between the second light-emitting material layer (960) and the second electron transport layer (970).

[0499] The third light-emitting unit (1030) includes a third hole transport layer (1050), a third light-emitting material layer (1060), a third electron transport layer (1070), and an electron injection layer (1080) that are sequentially stacked. Additionally, the third light-emitting unit (1030) may further include at least one of a third electron blocking layer (1055) located between the third hole transport layer (1050) and the third light-emitting material layer (1060), and a third hole blocking layer (1075) located between the third light-emitting material layer (1060) and the third electron transport layer (1070).

[0500] At this time, one of the first to third light-emitting material layers (860, 960, 1060) contains the organometallic compound of the present invention and emits green (G) light. At this time, another of the first to third light-emitting material layers (860, 960, 1060) emits red (R) light, and the other emits blue (B) light. Thus, the organic light-emitting diode (800) can achieve white (W) light emission.

[0501] For example, the second light-emitting material layer (960) may emit green (G) light by including the organometallic compound of the present invention, the first light-emitting material layer (860) may emit red (R) light, and the third light-emitting material layer (1060) may emit blue (B) light.

[0502] The first charge generation layer (890) is located between the first light-emitting unit (830) and the second light-emitting unit (930), and the second charge generation layer (990) is located between the second light-emitting unit (930) and the third light-emitting unit (1030). The first charge generation layer (890) includes a first N-type charge generation layer (910) located adjacent to the first light-emitting unit (830) and a first P-type charge generation layer (920) located adjacent to the second light-emitting unit (930). The second charge generation layer (990) includes a second N-type charge generation layer (1010) located close to the second light-emitting unit (930) and a second P-type charge generation layer (1020) located adjacent to the third light-emitting unit (1030). At this time, the first and second N-type charge generation layers (910, 1010) each inject electrons into the first and second light-emitting units (830, 930), and the first and second P-type charge generation layers (920, 1020) each inject holes into the second and third light-emitting units (930, 1030).

[0503] The second light-emitting material layer (960) includes the first host and the first dopant (966), which is an organometallic compound of the present invention, and emits green (G) light. The first host is one of mCP-CN, CBP, mCBP, mCP, DPEPO, PPT, TmPyPB, PYD-2Cz, DCzDBT, DCzTPA, pCzB-2CN, mCzB-2CN, TSPO1, CCP, 4-(3-(triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(6-(9H-carbazole-9-yl)pyridine-3-yl)-9H-3,9'-bicarbazole, BCzPh, TCP, TCTA, CDBP, DMFL-CBP, Spiro-CBP, TCz1 It is possible, but is not limited to this.

[0504] The first dopant (966) may be doped into the second light-emitting material layer (960) in a ratio of 1 to 20 weight%, preferably 1 to 10 weight%. For example, the second light-emitting material layer (960) may have a thickness of 10 to 100 nm, preferably 20 to 50 nm.

[0505] The first light-emitting material layer (860) may be a red (R) light-emitting material layer. The first light-emitting material layer (860) includes a second host and a second dopant which is a red (R) dopant. Additionally, the third light-emitting material layer (1060) includes a third host and a third dopant which is a blue (B) dopant.

[0506] The second and third dopants in the first and third light-emitting material layers (860, 1060) may each be doped in a ratio of 1 to 30 weight%. Additionally, the first and third light-emitting material layers (860, 1060) may each be formed with a thickness of 10 to 200 nm, preferably 20 to 100 nm, and more preferably 20 to 50 nm.

[0507] As described above, the organic light-emitting diode (D2) has a tandem structure of a first light-emitting unit (830) including a first light-emitting material layer (860) that emits red light, a second light-emitting unit (930) including a second light-emitting material layer (960) that emits green light, and a third light-emitting unit (1030) including a third light-emitting material layer (1060) that emits blue light, and emits white light.

[0508] In addition, since one of the light-emitting material layers (860, 960, 1060) includes the organometallic compound of the present invention, the light-emitting efficiency, color purity, and lifespan of the organic light-emitting diode (D2) and the organic light-emitting display device (400) are improved.

[0509] These organic light-emitting diodes (D2) can be used in an organic light-emitting display device (400 of FIG. 4) that includes a color filter layer (480) to realize a color image.

[0511] FIG. 8 is a schematic cross-sectional view of an organic light-emitting diode according to the seventh embodiment of the present invention.

[0512] As illustrated in FIG. 8, an organic light-emitting diode (D2) according to the seventh embodiment of the present invention comprises a first electrode (810) and a second electrode (820) facing each other, a first light-emitting unit (830A) located between the first electrode (810) and the second electrode (820), a second light-emitting unit (930A) located between the first light-emitting unit (830A) and the second electrode (820), a third light-emitting unit (1030A) located between the second light-emitting unit (930A) and the second electrode (820), a first charge-generating layer (810) located between the first and second light-emitting units (830A, 930A), and a second charge-generating layer (990) located between the second and third light-emitting units (930A, 1030A).

[0513] The first electrode (810) may be an anode, and the second electrode (820) may be a cathode.

[0514] The first light-emitting unit (830A) includes a hole injection layer (840), a first hole transport layer (850), a first light-emitting material layer (860A), and a first electron transport layer (870) that are sequentially stacked. Additionally, it may include a first electron blocking layer (855) and / or a first hole blocking layer (875) as needed.

[0515] The second light-emitting unit (930A) includes a second hole transport layer (950), a second light-emitting material layer (960A), and a second electron transport layer (970) that are sequentially stacked. Additionally, it may include a second electron blocking layer (955) and / or a second hole blocking layer (975).

[0516] The third light-emitting unit (1030A) includes a third hole transport layer (1050), a third light-emitting material layer (1060A), a third electron transport layer (1070), and an electron injection layer (1080) that are sequentially stacked. Additionally, it may include a third electron blocking layer (1055) and / or a third hole blocking layer (1075).

[0517] A first charge generating layer (890) located between the first and second light-emitting units (830A, 930A) includes a first N-type charge generating layer (910) located adjacent to the first light-emitting unit (830A) and a first P-type charge generating layer (920) located adjacent to the second light-emitting unit (930A). Meanwhile, a second charge generating layer (990) located between the second and third light-emitting units (930A, 1030A) includes a second N-type charge generating layer (1010) located adjacent to the second light-emitting unit (930A) and a second P-type charge generating layer (1020) located adjacent to the third light-emitting unit (1030A).

[0518] The organic light-emitting diode (D2) of FIG. 7 and the organic light-emitting diode (D2) of FIG. 8 differ in the first to third light-emitting material layers (860A, 960A, 1060A). Therefore, a detailed description of the remaining components excluding the first to third light-emitting material layers (860A, 960A, 1060A) is omitted.

[0519] One of the first to third light-emitting material layers (860A, 960A, 1060A) may include an organometallic compound of the present invention. Below, an organic light-emitting diode (D2) in which the second light-emitting material layer (960A) includes an organometallic compound of the present invention will be described.

[0520] The second light-emitting material layer (960A) includes a lower light-emitting material layer (962) located between the second electron blocking layer (955) and the second hole blocking layer (975), and an upper light-emitting material layer (964) located between the lower light-emitting material layer (962) and the second hole blocking layer (975). At this time, one of the upper and lower light-emitting material layers (962, 964) may emit green (G) light by including an organometallic compound of the present invention, and the other of the upper and lower light-emitting material layers (962, 964) may emit red (R) light. Below, an organic light-emitting diode (D2) in which the lower light-emitting material layer (962) includes an organometallic compound of the present invention will be described.

[0521] The lower light-emitting material layer (962) of the second light-emitting material layer (960A) includes a first host and a first dopant (968). The first host is one of mCP-CN, CBP, mCBP, mCP, DPEPO, PPT, TmPyPB, PYD-2Cz, DCzDBT, DCzTPA, pCzB-2CN, mCzB-2CN, TSPO1, CCP, 4-(3-(triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(6-(9H-carbazole-9-yl)pyridine-3-yl)-9H-3,9'-bicarbazole, BCzPh, TCP, TCTA, CDBP, DMFL-CBP, Spiro-CBP, TCz1 The first dopant (968) is an organometallic compound of the present invention.

[0522] The upper light-emitting material layer (964) of the second light-emitting material layer (960A) may include a second host and a second dopant which is a red dopant. For example, the second dopant may be an organometallic compound having the structure of Formula 9 or Formula 10.

[0523] The first dopant (968) may be doped into the lower light-emitting material layer (962) at a ratio of 1 to 20 weight%, preferably 1 to 10 weight%. For example, the lower light-emitting material layer (962) may have a thickness of 10 to 100 nm, preferably 20 to 50 nm.

[0524] The second dopant may be doped into the upper light-emitting material layer (964) at a ratio of 1 to 30 weight percent. The upper light-emitting material layer (964) may be formed with a thickness of 10 to 100 nm, preferably 10 to 50 nm, but the present invention is not limited thereto.

[0525] The first and third light-emitting material layers (860A, 1060A) may be blue (B) light-emitting material layers. The first and third light-emitting material layers (860A, 1060A) may include a third host and a third dopant which is a blue (B) dopant.

[0526] The third dopant, which is a blue dopant forming the first and third light-emitting material layers (860A, 1060A) respectively, may be doped into each light-emitting material layer at a ratio of 1 to 30 weight%. For example, the first and third light-emitting material layers (860A, 1060A) may each be formed with a thickness of 10 to 200 nm, preferably 20 to 100 nm, more preferably 20 to 50 nm, but the present invention is not limited thereto.

[0527] As described above, the organic light-emitting diode (D2) has a tandem structure, and one of the light-emitting material layers includes the organic metal compound of the present invention. Accordingly, the organic light-emitting diode (D2) can achieve white light emission with improved light-emitting efficiency, color purity, and light-emitting lifetime.

[0528] These organic light-emitting diodes (D2) can be used in an organic light-emitting display device (400 of FIG. 4) that includes a color filter layer (480) to realize a color image.

[0530] Although the present invention has been described above with reference to preferred embodiments, those skilled in the art will understand that various modifications and changes can be made to the invention without departing from the technical spirit and scope of the invention as described in the following claims. Explanation of the symbols

[0532] 100, 400, 1100: Organic light-emitting display device D1, D2: Organic light-emitting diode 210, 310, 410, 510, 610, 810,: First electrode 220, 320, 420, 520, 620, 810,: Second electrode 230, 530: Organic light-emitting layer 330, 430, 630, 730, 730A, 830, 930, 930A, 1030, 1030A,: Light-emitting unit 360, 460, 660, 760, 760A, 860, 960, 960A, 1060, 1060A: Luminescent material layer 762, 962: Lower luminescent material layer 764, 964: Upper luminescent material layer 690, 890, 990: Charge generation layer 362, 766, 768, 966, 968: Green dopant

Claims

Claim 1 An organometallic compound represented by the following chemical formula 2-2, wherein X1 to X5 are each independently CR4, R1 and R21 are each independently selected from C1 to C10 alkyl groups that are unsubstituted or deuterium-substituted, R31 is selected from C1 to C10 alkyl groups that are unsubstituted or deuterium-substituted or C3 to C20 cycloalkyl groups that are unsubstituted or deuterium-substituted, R4 is hydrogen, R5, R6, and R7 are each independently C1 to C10 alkyl groups, a is 1, and n is an integer from 0 to 2. [Chemical Formula 2-2] Claim 2 delete Claim 3 The organometallic compound of claim 1, characterized in that the organometallic compound is one of the compounds of the following chemical formula 3.[Chemical Formula 3] Claim 4 delete Claim 5 An organometallic compound according to claim 1, characterized in that n is 2. Claim 6 An organic light-emitting diode comprising: a first electrode; a second electrode facing the first electrode; and a first light-emitting unit positioned between the first electrode and the second electrode and comprising a first light-emitting material layer, wherein the first light-emitting material layer comprises an organometallic compound described in any one of claims 1, 3, and 5. Claim 7 An organic light-emitting diode according to claim 6, wherein the first light-emitting material layer comprises a first host and a first dopant, and the first dopant is the organometallic compound. Claim 8 An organic light-emitting diode according to claim 7, further comprising a second light-emitting unit positioned between the first light-emitting unit and the first electrode, and a first charge-generating layer positioned between the first light-emitting unit and the second light-emitting unit, wherein the second light-emitting material layer comprises a blue dopant. Claim 9 An organic light-emitting diode according to claim 8, wherein the first light-emitting unit further comprises a third light-emitting material layer located below or above the first light-emitting material layer, and the third light-emitting material layer comprises a red dopant. Claim 10 An organic light-emitting diode according to claim 8, further comprising: a third light-emitting unit located between the first light-emitting unit and the second electrode and including a third light-emitting material layer; and a second charge-generating layer located between the first light-emitting unit and the third light-emitting unit, wherein the third light-emitting material layer includes a red dopant. Claim 11 An organic light-emitting diode according to claim 8, further comprising: a third light-emitting unit located between the first light-emitting unit and the second electrode and including a third light-emitting material layer; a second charge-generating layer located between the first light-emitting unit and the third light-emitting unit, wherein the first light-emitting unit further comprises a fourth light-emitting material layer located below or above the first light-emitting material layer, wherein the third light-emitting material layer includes a blue dopant and the fourth light-emitting material layer includes a red dopant. Claim 12 An organic light-emitting diode comprising: a substrate; a first light-emitting unit located on the substrate and comprising a first electrode, a second electrode facing the first electrode, and a first light-emitting material layer located between the first electrode and the second electrode; and a thin-film transistor located between the substrate and the organic light-emitting diode and connected to the organic light-emitting diode, wherein the first light-emitting material layer comprises an organometallic compound described in any one of claims 1, 3, and 5. Claim 13 An organic light-emitting device according to claim 12, wherein the first light-emitting material layer comprises a first host and a first dopant, and the first dopant is the organometallic compound. Claim 14 An organic light-emitting diode according to claim 13, wherein the organic light-emitting diode further comprises a second light-emitting material layer, a second light-emitting unit located between the first light-emitting unit and the first electrode, and a first charge-generating layer located between the first light-emitting unit and the second light-emitting unit, and wherein the second light-emitting material layer comprises a blue dopant. Claim 15 An organic light-emitting device according to claim 14, wherein the first light-emitting unit further comprises a third light-emitting material layer located below or above the first light-emitting material layer, and the third light-emitting material layer comprises a red dopant. Claim 16 An organic light-emitting diode according to claim 14, wherein the organic light-emitting diode further comprises a third light-emitting unit located between the first light-emitting unit and the second electrode and including a third light-emitting material layer, and a second charge-generating layer located between the first light-emitting unit and the third light-emitting unit, wherein the third light-emitting material layer includes a red dopant. Claim 17 An organic light-emitting diode according to claim 14, wherein the organic light-emitting diode further comprises a third light-emitting unit located between the first light-emitting unit and the second electrode and including a third light-emitting material layer, and a second charge-generating layer located between the first light-emitting unit and the third light-emitting unit, wherein the first light-emitting unit further comprises a fourth light-emitting material layer located below or above the first light-emitting material layer, and wherein the third light-emitting material layer comprises a blue dopant and the fourth light-emitting material layer comprises a red dopant. Claim 18 An organic light-emitting device according to claim 12, wherein a red pixel, a green pixel, and a blue pixel are defined on the substrate, and the organic light-emitting diode corresponds to the red pixel, the green pixel, and the blue pixel, and further comprising a color filter layer located between the substrate and the organic light-emitting diode or on top of the organic light-emitting diode corresponding to the red pixel, the green pixel, and the blue pixel.

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