High-refractive-index organic material and light-emitting device comprising same

Abstract

The present invention relates to a high-refractive-index organic material and a light-emitting device comprising same, and, more specifically, to a high-refractive-index organic material and a light-emitting device comprising same, the material being capable of functioning as a capping layer that has improved high refractive index, thin film stability, and durability and minimizes light absorption in the visible spectrum.

Description

High refractive index organic material and light-emitting device containing the same

[0001] The present invention relates to a high refractive index organic material and a light-emitting device including the same, and more particularly, to a high refractive index organic material that can function as a capping layer with improved high refractive index, thin film stability and durability, and minimized light absorption in the visible light region, and a light-emitting device including the same.

[0002] Electroluminescent devices (EL devices) are self-luminous display devices that have the advantages of a wide viewing angle, excellent contrast, and a fast response time.

[0003] EL devices are classified into inorganic EL devices and organic EL devices depending on the material used to form the emitting layer. Organic EL devices have the advantages of superior brightness, driving voltage, and response speed characteristics compared to inorganic EL devices, and are capable of multicolorization.

[0004] A typical organic EL device has a structure in which an anode is formed on top of a substrate, and a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially formed on top of the anode. Here, the hole transport layer, light-emitting layer, and electron transport layer are organic thin films made of organic compounds.

[0005] The operating principle of the organic EL device having the structure described above is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light-emitting layer via the hole transport layer. Meanwhile, electrons are injected from the cathode to the light-emitting layer via the electron transport layer, and carriers recombine in the light-emitting layer region to generate excitons. These excitons change from an excited state to a ground state, which causes molecules in the light-emitting layer to emit light, forming an image. Light-emitting materials are divided into fluorescent materials that use singlet excitons and phosphorescent materials that use triplet states, depending on their light-emitting mechanism. Depending on the light-emitting mechanism of the light-emitting layer, fluorescence has an internal quantum efficiency of 25% and phosphorescence has an internal quantum efficiency of 100%. In addition, it is known that the external luminescence efficiency, in which light emitted internally is emitted externally, is typically about 20% of the internal luminescence efficiency.

[0006] To realize a display device with high efficiency and high color reproducibility, it is necessary to prevent the light going out from being totally reflected and thus lost, or from being absorbed and lost within the device. Among the various technologies for implementing external light extraction as described above, the performance of organic light-emitting devices has been improved by applying an organic compound with a refractive index of 1.7 or higher as a capping layer. Therefore, to realize an organic light-emitting device with high efficiency and high color reproducibility, the development of a capping layer material that has a high refractive index, improved thin film stability and durability, and minimizes light absorption in the visible light region is required.

[0007] The purpose of the present invention is to provide a high refractive index organic material that can function as a capping layer with improved high refractive index, thin film stability and durability, and minimized light absorption in the visible light region, and an organic electroluminescent device including the same.

[0008] The purpose of the present invention is to provide an organic compound having high refractive index characteristics, a high glass transition temperature, high thin film stability and durability, and minimized visible light absorption, and an organic electroluminescent device including the same capable of high efficiency and high color reproducibility.

[0009] Here, the organic light-emitting device may include a supporting substrate, a first electrode formed on the supporting substrate, a hole injection layer formed on the first electrode, a hole transport layer formed on the hole injection layer, a light-emitting layer formed on the hole transport layer, an electron transport layer formed on the light-emitting layer, an electron injection layer formed on the electron transport layer, a second electrode formed on the electron injection layer, and a capping layer formed on the first electrode, the second electrode, or both.

[0010]

[0011] The present invention provides an organic electroluminescent device and an electronic device thereof, characterized in that it includes at least one organic layer between a first electrode and a second electrode, and includes a capping layer having a high refractive index on the opposite surface of the electrode, wherein the capping layer has a refractive index of 1.7 or more at a wavelength of 380 nm to 730 nm, and may include a compound having the following compound 1A or compound 1B.

[0012] [Compound 1A]

[0013]

[0014] [Compound 1B]

[0015]

[0016] In the above compound 1A or compound 1B, X1 to X7 are each independently selected from CR1 or N, and R1 is each independently hydrogen, deuterium, a halogen group, a hydroxyl group (-OH), a nitro group, a cyano group, C1~C 30 Alkyl group of C1~C 30 Alkoxy group, substituted or unsubstituted C6~C60 A monocyclic or polycyclic compound of the mobilizer, substituted or unsubstituted C6~C 60 Diatomic mono- or polycyclic compounds and C1~C 30 is selected from the group consisting of silyl groups, and R1 of multiple CR1s are each independently the same or different, and L1 and L2 are each a direct bond or substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 is selected from diatomic monocyclic or polycyclic compounds, and Ar1 and Ar2 are each substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic single or polycyclic compounds, wherein the substitution is hydrogen, deuterium, halogen group, hydroxyl group (-OH), nitro group, cyano group, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 It can be selected from the list of cylinders, but is not limited thereto.

[0017] In the compound represented by the above compound 1A or compound 1B, a plurality of L1 and L2 may be the same as each other, and a plurality of Ar1 and Ar2 may be the same as each other.

[0018] Ar1 and Ar2 of the above compound 1A or compound 1B may include a compound having the structure of the following compound 2A or compound 2B.

[0019] [Compound 2A]

[0020]

[0021] [Compound 2B]

[0022]

[0023] In the above compound 2A or compound 2B, X 11 is selected from CR2 or N,

[0024] X 12 is selected from O, S, NR3, CR4R5, SiR5R6, PR7, S=O, O=S=O, C=O, C=S, Si=O, Si=S, and X 21 Inland X 24 or X 31 Inland X 35 are each independently selected from CR8 or N, and R2 to R8 are each independently hydrogen, deuterium, halogen group, hydroxyl group (-OH), nitro group, cyano group, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 is selected from the group consisting of silyl groups, and R8 of multiple CR8s may be independently the same or different. Here, *- indicates a site that binds to L1 and L2.

[0025] The above compound 2A may be selected from compounds 3A to 3E below, but is not limited thereto.

[0026] [Compound 3A]

[0027]

[0028] [Compound 3B]

[0029]

[0030] [Compound 3C]

[0031]

[0032] [Compound 3D]

[0033]

[0034] *

[0035] [Compound 3E]

[0036]

[0037] In the above compounds 3A to 3E, R 11 , R 12 are each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 is selected from the group of R, and m can be selected from an integer from 0 to 4, but is not limited thereto, and may be a plurality of R 11 can be independently the same or different.

[0038] The capping layer may include at least one of the compounds 1 to 974 below, but is not limited thereto.

[0039]

[0040] [Compound 1 to Compound 974]

[0041]

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[0138]

[0139] In order to solve the above problem, in one embodiment of the present invention, a compound that can be used as a capping layer of a light-emitting device is provided, wherein the compound has a refractive index of 1.7 or more at a wavelength of 380 nm to 730 nm, and the compound is represented by the following chemical formula 1A or chemical formula 1B.

[0140] [Chemical Formula 1A]

[0141]

[0142] [Chemical Formula 1B]

[0143]

[0144] (Here, X1 to X7 are each independently selected from CR1 or N,

[0145] R1 is each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 30 Alkyl group of C1~C 30 Alkoxy group, substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer, substituted or unsubstituted C6~C 60 Diatomic mono- or polycyclic compounds and C1~C 30 Selected from the cylinders of

[0146] The R1 of multiple CR1s may be independently the same or different,

[0147] L1 and L2 are each a direct bond or substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic mono- or polycyclic compounds,

[0148] Ar1 and Ar2 are each substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic mono- or polycyclic compounds,

[0149] The above substitutions include hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 ) can be selected from the list of

[0150]

[0151] In embodiments of the present invention, L1 and L2 may be the same as each other, and Ar1 and Ar2 may be the same as each other.

[0152] In one embodiment of the present invention, Ar1 and Ar2 may each independently have a structure of the following chemical formula 2A or chemical formula 2B.

[0153] [Chemical Formula 2A]

[0154]

[0155] [Chemical Formula 2B]

[0156]

[0157] (Here, X 11 is selected from CR2 or N,

[0158] X 12 is selected from O, S, NR3, CR4R5, SiR5R6, PR7, S=O, O=S=O, C=O, C=S, Si=O, or Si=S,

[0159] X 21 Inland X 24 and X 31 Inland X 35 are each independently selected from CR8 or N,

[0160] R2 to R8 are each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 Selected from the cylinders of

[0161] The R8 of CR8 are each independently selected and may be the same or different.

[0162] *- indicates the site that binds to L1 and L2)

[0163]

[0164] In one embodiment of the present invention, the chemical formula 2A may be selected from any one of the following chemical formulas 3A to 3E.

[0165] [Chemical Formula 3A]

[0166]

[0167] [Chemical Formula 3B]

[0168]

[0169] [Chemical Formula 3C]

[0170]

[0171] [Chemical Formula 3D]

[0172]

[0173] [Chemical Formula 3E]

[0174]

[0175] (Here, R 11 , R 12 are each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 Selected from the cylinders of

[0176] m is an integer from 0 to 4,

[0177] Multiple R's 11) may be independently the same or different)

[0178]

[0179] In order to solve the above problem, in one embodiment of the present invention, a light-emitting device including the compound described above as a capping layer is provided.

[0180]

[0181] In embodiments of the present invention, the thickness of the capping layer may be 10 nm to 150 nm.

[0182] In embodiments of the present invention, the light-emitting device includes a hole injection layer, and the hole injection layer includes 0.5 wt% to 50 wt% of a p-dopant, and the lowest unoccupied orbital (LUMO) value of the p-dopant may be -4.8 eV or less.

[0183]

[0184] In embodiments of the present invention, the light-emitting device includes at least one of a hole injection layer and a hole transport layer, and at least one of the hole injection layer and the hole transport layer of the light-emitting device may include a tertiary aryl amine.

[0185]

[0186] In embodiments of the present invention, the light-emitting device includes a light-emitting layer, and the light-emitting layer may include a fluorescent dopant including an arylamine ring, a delayed fluorescent dopant including a boron ring compound or a nitrile group, a phosphorescent dopant including an iridium or platinum complex, or a combination of two or more of the fluorescent dopant, the delayed fluorescent dopant, and the phosphorescent dopant.

[0187]

[0188] In embodiments of the present invention, the light-emitting device includes an electron transport layer, and the electron transport layer may include at least one selected from the group consisting of a triazine substituent, a pyridine substituent, a pyrimidine substituent, an oxadiazole substituent, a benzimidazole substituent, and a phenanthroline substituent.

[0189]

[0190] In order to solve the above-described problem, in one embodiment of the present invention, a compound that can be used as a capping layer of an organic light-emitting device, an organic solar cell, an organic thin-film transistor, or a single-color or white lighting device is provided, wherein the compound has a refractive index of 1.7 or more at a wavelength of 380 nm to 730 nm, and the compound is represented by the following chemical formula 1A or chemical formula 1B.

[0191] [Chemical Formula 1A]

[0192]

[0193] [Chemical Formula 1B]

[0194]

[0195] (Here, X1 to X7 are each independently selected from CR1 or N,

[0196] R1 is each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 30 Alkyl group of C1~C 30 Alkoxy group, substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer, substituted or unsubstituted C6~C 60 Diatomic mono- or polycyclic compounds and C1~C 30 Selected from the cylinders of

[0197] The R1 of multiple CR1s may be independently the same or different,

[0198] L1 and L2 are each a direct bond or substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic mono- or polycyclic compounds,

[0199] Ar1 and Ar2 are each substituted or unsubstituted C6~C 60A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic mono- or polycyclic compounds,

[0200] The above substitutions include hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 ) can be selected from the list of

[0201]

[0202] In order to solve the above problem, in one embodiment of the present invention, a method for manufacturing a light-emitting device is provided, comprising: forming a first electrode on a substrate; forming a hole injection layer on the first electrode; forming a hole transport layer on the hole injection layer; forming a light-emitting layer on the hole transport layer; forming an electron transport layer on the light-emitting layer; forming an electron injection layer on the electron transport layer; forming a second electrode on the electron injection layer; and forming a capping layer on the second electrode; wherein the capping layer includes the compound described above.

[0203]

[0204]

[0205] An organic light-emitting device according to one embodiment of the present invention can improve external luminescence efficiency and color coordinates through a capping layer including an organic compound with a high refractive index for improving luminous efficiency.

[0206] In addition, it is possible to suppress color conversion shape by maintaining a wide band gap that cannot absorb RGB wavelengths of the organic light-emitting device, thereby exhibiting high color purity.

[0207] FIG. 1 illustrates an organic light-emitting device structure according to one embodiment of the present invention.

[0208]

[0209] FIG. 1 is an exemplary diagram of an organic light-emitting device according to one embodiment of the present invention.

[0210]

[0211] Referring to FIG. 1, the present invention relates to an organic light-emitting device having improved light efficiency and color purity, characterized by including an anode (100) functioning as a first electrode, a cathode (700) functioning as a second electrode, and multiple organic layers on the first and second electrodes, and at least one organic layer, i.e., a capping layer, positioned opposite to the organic layers of the first and second electrodes. The capping layer comprises a compound of Compound 1A or Compound 1B.

[0212]

[0213] The structure and manufacturing method of an organic electroluminescent device employing a high-refractive-index compound according to the present invention are described. The organic electroluminescent device according to the present invention may employ the structure of a conventional light-emitting device, and the structure may be modified as needed.

[0214] An organic light-emitting device to which a capping layer according to embodiments of the present invention can be applied has a structure including an organic film (light-emitting layer) between a first electrode (anode, 100) and a second electrode (cathode, 700), and, as a representative example, as shown in FIG. 1, may have a structure including a hole injection layer (200), a hole transport layer (300), a light-emitting layer (400), an electron transport layer (500), an electron injection layer (600), and a cathode (700).

[0215] In another embodiment of the present invention, an organic light emitting device may be used in which at least one of the hole injection layer (200) and the electron injection layer (600) is omitted, and, if necessary, a hole suppression layer, an electron suppression layer, etc. may be further included.

[0216] In another embodiment of the present invention, the light-emitting layer (400) may include a material of an inorganic light-emitting layer as well as an organic light-emitting layer.

[0217]

[0218] An organic light emitting device according to embodiments of the present invention has a structure including a light emitting layer (400) between an anode electrode (positive electrode, 100) and a cathode electrode (negative electrode, 700), and includes a hole injection layer (200) and a hole transport layer (300) between the anode electrode (positive electrode, 100) and the light emitting layer (400), and further includes an electron transport layer (500) and an electron injection layer (600) between the light emitting layer (400) and the cathode electrode (negative electrode, 700).

[0219] Meanwhile, the organic light-emitting device of FIG. 1 according to one embodiment of the present invention is manufactured through the following process, which is merely illustrative and is not limited to this method.

[0220] First, an anode electrode is formed by coating an anode material on the upper part of the substrate. Here, the substrate may be a substrate commonly used in this field, and in particular, a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance is preferable. In addition, the anode electrode material formed on the substrate may be a material having a high work function to facilitate hole injection. Specific examples include, but are not limited to, indium tin oxide (ITO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity.

[0221] A hole injection layer (HIL) is selectively formed on the upper portion of the anode electrode. At this time, the hole injection layer is formed through a conventional method such as vacuum deposition or spin coating. There is no particular limitation on the material for the hole injection layer, but in order to minimize the energy level difference with the anode electrode, a tertiary amine organic material such as an aromatic ring amine is mainly used, and specific examples include m-MTDATA, DNTPD, NPB, TDATA, 2T-NATA, etc., and in the case of a metal complex compound, there is a CuPc (copper phthalocyanine) compound, and materials with a low LUMO value include HATCN, F4TCNQ, NDP-9, etc.

[0222] Next, the hole transport layer (HTL) is formed on the hole injection layer by a conventional method such as vacuum deposition or spin coating. As the material for the hole transport layer, N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine, N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine:α-NPD) can be generally used, but is not limited thereto.

[0223] Next, an emission layer (EML) is formed on top of the hole transport layer. A fluorescent material can be used as the material for forming the emission layer, and a phosphorescent material composed of a transition metal iridium complex or platinum complex can be used.

[0224] Fluorescent materials have been mainly used for blue emission, and phosphorescent materials have been mainly used for green and red emission. However, there is a trend of changing fluorescent materials to phosphorescent or delayed fluorescent materials to improve efficiency. The light-emitting layer is composed of a host and a dopant, and the dopant content can be included within the range of 1 to 95 wt% based on the total weight of the material constituting the light-emitting layer. The light-emitting layer can be formed by a vacuum deposition method, and can also be deposited through a wet process such as spin coating, and laser induced thermal imaging (LITI) can also be used. Optionally, a hole blocking layer (HBL) can be formed on the light-emitting layer to block excitons formed in the light-emitting material from moving to the electron transport layer or to block holes from moving to the electron transport layer. The material for the hole blocking layer is not particularly limited, but a phenanthroline-based compound (e.g., BCP) can be used. This can be formed by a vacuum deposition method or a spin coating method.

[0225] Additionally, an electron transport layer (ETL) may be formed on the light-emitting layer, and this may be formed using a vacuum deposition method or a spin coating method. Materials for the electron transport layer are not particularly limited, but may include TBPI, Bphen, TAZ, and aluminum complexes (e.g., Alq3(tris(8-quinolinolato)-aluminum)).

[0226] An electron injection layer (EIL) can be formed on the electron transport layer using a method such as vacuum deposition or spin coating, and materials for the electron injection layer are not particularly limited, but materials such as LiF, NaCl, and CsF can be used.

[0227] Next, a cathode electrode is formed on top of the electron injection layer through vacuum deposition, thereby completing the light-emitting device. Here, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), indium zinc oxide (IZO), etc. can be used as the cathode metal.

[0228]

[0229] Next, a capping layer is used, as previously described, because an organic material with a high refractive index affects the improvement of external luminescence efficiency. Typically, the capping layer may have a refractive index of 1.7 or higher at a wavelength of 380 nm to 730 nm.

[0230] In order to construct an organic light-emitting device, a structure in which the organic layers described above are laminated is applied, but the light emitted cannot be emitted to the outside due to internal reflection, and as a result, the light is extinguished within the device, which has been a problem in reducing efficiency.

[0231] To solve this problem, when a capping layer illustrated as compound 1A or compound 1B is used, the emission performance is improved by the constructive interference effect in the process of emitted light being emitted to the outside, so that the light efficiency of the organic light-emitting device can be greatly improved.

[0232] In addition, the organic light-emitting device according to the present invention has a laminated structure as shown in Fig. 1, and, if necessary, it is also possible to further form one or two intermediate layers, such as a hole-blocking layer. In addition, the thickness of each layer of the light-emitting device can be determined as necessary within a range generally used in this field.

[0233] In addition, although the capping layer (800) is illustrated as being positioned on the upper surface of the cathode (700) in FIG. 1, in embodiments of the present invention, the position of the capping layer (800) is not limited, and for example, it may be positioned on the anode (100) side. In this case, the position of the substrate may vary.

[0234]

[0235] Hereinafter, a capping layer with improved refractive index, thin film stability, and durability, and with minimized light absorption in the visible light region, and a manufacturing method thereof, will be described in detail with reference to synthesis examples, examples, and drawings. However, the present invention is not limited to these synthesis examples, examples, and drawings.

[0236]

[0237] [Synthesis Example 1] Synthesis of the capping layer compound of compound 3

[0238]

[0239] 9H-carbazole (10.0 g, 59.8 mmol) and 1-bromoisoquinoline (18.7 g, 89.7 mmol) were placed in a two-necked round-bottom flask, 200 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (2.8 g, 15.0 mmol), tripotassium phosphate (25.4 g, 119.6 mmol), and 1,2-cyclohexanediamine (4.1 g, 35.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was then used to obtain compound 3-1 (21.9 g, 74.5 mmol) using the ratio of toluene and hexane. MS:[M+H] + =294

[0240] Compound 3-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.3 g, 35.7 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 3-2 (6.8 g, 14.9 mmol). MS: [M+H] + =452

[0241] Compound 3-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole-6-carbonitrile (4.8 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.2 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 3 (4.0 g, 6.9 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =579

[0242]

[0243] [Synthesis Example 2] Synthesis of the capping layer compound of compound 20

[0244]

[0245] Compounds 3-1 and 3-2 are synthesized in the same manner as in Synthesis Example 1.

[0246] Afterwards, compound 3-2 (5.0 g, 11.1 mmol), (3',5'-dicyano-[1,1'-biphenyl]-4-yl)boronic acid (6.6 g, 26.5 mmol) were added to 110 ml of toluene, 28 ml of ethanol, and 28 ml of DI water, and stirred. Then, potassium carbonate (9.2 g, 66.3 mmol) and Tetrakis(triphenylphosphine)-palladium(0) (1.3 g, 1.1 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the produced solid was filtered. Afterwards, compound 20 (5.3 g, 7.5 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =699

[0247]

[0248] [Synthesis Example 3] Synthesis of the capping layer compound of compound 21

[0249]

[0250] 9H-carbazole (10.0 g, 59.8 mmol) and 4-bromoisoquinoline (18.7 g, 89.7 mmol) were placed in a two-necked round-bottom flask, 200 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (2.8 g, 15.0 mmol), tripotassium phosphate (25.4 g, 119.6 mmol), and 1,2-cyclohexanediamine (4.1 g, 35.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 21-1 (22.7 g, 77.1 mmol) using the ratio of toluene and hexane. MS:[M+H] + =294

[0251] Compound 21-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.3 g, 35.7 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 21-2 (7.0 g, 15.5 mmol). MS: [M+H] + =452

[0252] Compound 21-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole (4.0 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.2 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 21 (4.4 g, 8.4 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =529

[0253]

[0254] [Synthesis Example 4] Synthesis of the capping layer compound of compound 84

[0255]

[0256] 9H-carbazole (10.0 g, 59.8 mmol) and 5-bromoisoquinoline (18.7 g, 89.7 mmol) were placed in a two-necked round-bottom flask, 200 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (2.8 g, 15.0 mmol), tripotassium phosphate (25.4 g, 119.6 mmol), and 1,2-cyclohexanediamine (4.1 g, 35.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was then used to obtain compound 84-1 (21.4 g, 72.7 mmol) using the ratio of toluene and hexane. MS:[M+H] + =294

[0257] Compound 84-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.3 g, 35.7 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 84-2 (6.5 g, 14.3 mmol). MS: [M+H] + =452

[0258] Compound 84-2 (5.0 g, 11.1 mmol) and benzo[d]thiazole (4.5 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.2 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 84 (4.4 g, 7.9 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =561

[0259]

[0260] [Synthesis Example 5] Synthesis of the capping layer compound of compound 139

[0261]

[0262] 9H-carbazole (10.0 g, 59.8 mmol) and 8-bromoquinoline (18.7 g, 89.7 mmol) were placed in a two-necked round-bottom flask, 200 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (2.8 g, 15.0 mmol), tripotassium phosphate (25.4 g, 119.6 mmol), and 1,2-cyclohexanediamine (4.1 g, 35.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was complete, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 139-1 (22.4 g, 76.3 mmol) using the ratio of toluene and hexane. MS:[M+H] + =294

[0263] Compound 139-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.3 g, 35.7 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 139-2 (6.9 g, 15.3 mmol). MS: [M+H] + =452

[0264] Compound 139-2 (5.0 g, 11.1 mmol), (4'-cyano-[1,1'-biphenyl]-4-yl)boronic acid (5.9 g, 26.5 mmol) were added to 110 ml of toluene, 28 ml of ethanol, and 28 ml of DI water, and stirred. Then, potassium carbonate (9.2 g, 66.3 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.3 g, 1.1 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the resulting solid was filtered. Afterwards, compound 139 (5.6 g, 8.6 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =649

[0265]

[0266] [Synthesis Example 6] Synthesis of the capping layer compound of compound 141

[0267]

[0268] 9H-carbazole (10.0 g, 59.8 mmol) and 1-bromonaphthalene (18.6 g, 89.7 mmol) were placed in a two-necked round-bottom flask, 200 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (2.8 g, 15.0 mmol), tripotassium phosphate (25.4 g, 119.6 mmol), and 1,2-cyclohexanediamine (4.1 g, 35.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 141-1 (22.4 g, 76.3 mmol) using the ratio of toluene and hexane. MS:[M+H] + =293

[0269] Compound 141-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.4 g, 35.8 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 141-2 (6.9 g, 15.3 mmol). MS: [M+H] + =451

[0270] Compound 141-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole (4.0 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 141 (4.1 g, 7.8 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =528

[0271]

[0272] [Synthesis Example 7] Synthesis of the capping layer compound of compound 143

[0273]

[0274] Compounds 141-1 and 141-2 are synthesized in the same manner as in Synthesis Example 6.

[0275] Afterwards, compound 141-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole-6-carbonitrile (4.8 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 143 (4.0 g, 6.9 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H]+ =578

[0276]

[0277] [Synthesis Example 8] Synthesis of the capping layer compound of compound 144

[0278]

[0279] Afterwards, compound 141-2 (5.0 g, 11.1 mmol) and benzo[d]thiazole (4.5 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 144 (5.1 g, 9.1 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =560

[0280]

[0281] [Synthesis Example 9] Synthesis of the capping layer compound of compound 147

[0282]

[0283] Compounds 141-1 and 141-2 are synthesized in the same manner as in Synthesis Example 6.

[0284] Afterwards, compound 141-2 (5.0 g, 11.1 mmol) and benzofuran (3.9 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 147 (4.4 g, 8.3 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =526

[0285]

[0286] [Synthesis Example 10] Synthesis of the capping layer compound of compound 150

[0287]

[0288] Compounds 141-1 and 141-2 are synthesized in the same manner as in Synthesis Example 6.

[0289] Afterwards, compound 141-2 (5.0 g, 11.1 mmol) and benzo[b]thiophene (4.5 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 150 (4.5 g, 8.0 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] +=558

[0290]

[0291] [Synthesis Example 11] Synthesis of the capping layer compound of compound 153

[0292]

[0293] Compounds 141-1 and 141-2 are synthesized in the same manner as in Synthesis Example 6.

[0294] Afterwards, compound 141-2 (5.0 g, 11.1 mmol) and 1-phenyl-1H-benzo[d]imidazole (6.5 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 153 (5.0 g, 7.4 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =678

[0295]

[0296] [Synthesis Example 12] Synthesis of the capping layer compound of compound 159

[0297]

[0298] Compounds 141-1 and 141-2 are synthesized in the same manner as in Synthesis Example 6.

[0299] Afterwards, compound 141-2 (5.0 g, 11.1 mmol), (4'-cyano-[1,1'-biphenyl]-4-yl)boronic acid (5.9 g, 26.6 mmol) were added to 110 ml of toluene, 28 ml of ethanol, and 28 ml of DI water, and stirred. Then, potassium carbonate (9.2 g, 66.5 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.3 g, 1.1 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the produced solid was filtered. Afterwards, compound 159 (5.4 g, 8.3 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =648

[0300]

[0301] [Synthesis Example 13] Synthesis of the capping layer compound of compound 181

[0302]

[0303] 9H-carbazole (10.0 g, 59.8 mmol) and 3-bromoquinoline (18.7 g, 89.7 mmol) were placed in a two-necked round-bottom flask, 200 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (2.8 g, 15.0 mmol), tripotassium phosphate (25.4 g, 119.6 mmol), and 1,2-cyclohexanediamine (4.1 g, 35.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was complete, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 181-1 (22.4 g, 76.3 mmol) using the ratio of toluene and hexane. MS:[M+H] + =294

[0304] Compound 181-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.4 g, 35.8 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 181-2 (6.7 g, 14.8 mmol). MS: [M+H] + =452

[0305] Compound 181-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole (4.0 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 181 (4.4 g, 8.4 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =529

[0306]

[0307] [Synthesis Example 14] Synthesis of the capping layer compound of compound 184

[0308]

[0309] Compounds 181-1 and 181-2 are synthesized in the same manner as in Synthesis Example 13.

[0310] Afterwards, compound 181-2 (5.0 g, 11.1 mmol) and benzo[d]thiazole (4.5 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 184 (4.4 g, 7.9 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =561

[0311]

[0312] [Synthesis Example 15] Synthesis of the capping layer compound of compound 200

[0313]

[0314] Compounds 181-1 and 181-2 are synthesized in the same manner as in Synthesis Example 13.

[0315] Afterwards, compound 181-2 (5.0 g, 11.1 mmol), (3',5'-dicyano-[1,1'-biphenyl]-4-yl)boronic acid (6.6 g, 26.6 mmol) were added to 110 ml of toluene, 28 ml of ethanol, and 28 ml of DI water, and stirred. Then, potassium carbonate (9.2 g, 66.5 mmol) and Tetrakis(triphenylphosphine)-palladium(0) (1.3 g, 1.1 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the produced solid was filtered. Afterwards, compound 200 (6.5 g, 9.3 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H]+ =699

[0316]

[0317] [Synthesis Example 16] Synthesis of the capping layer compound of compound 207

[0318]

[0319] 9H-carbazole (5.0 g, 29.9 mmol) and 6-bromoquinoline (9.3 g, 44.9 mmol) were placed in a two-necked round-bottom flask, 100 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 h. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was then used to obtain compound 207-1 (10.7 g, 36.3 mmol) using the ratio of toluene and hexane. MS: [M+H] + =294

[0320] Compound 207-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.4 g, 35.8 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 207-2 (6.5 g, 14.4 mmol). MS: [M+H] + =452

[0321] Compound 207-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole (4.0 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 207 (4.4 g, 8.3 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =529

[0322]

[0323] [Synthesis Example 17] Synthesis of the capping layer compound of compound 239

[0324]

[0325] 9H-carbazole (5.0 g, 29.9 mmol) and 6-bromoisoquinoline (9.3 g, 44.9 mmol) were placed in a two-necked round-bottom flask, and 100 ml of 1,4-dioxane was added and stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was then used to obtain compound 239-1 (10.8 g, 36.8 mmol) using the ratio of toluene and hexane. MS: [M+H] + =294

[0326] Compound 239-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.4 g, 35.8 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 239-2 (6.8 g, 14.9 mmol). MS: [M+H] + =452

[0327] Compound 239-2 (5.0 g, 11.1 mmol), (4'-cyano-[1,1'-biphenyl]-4-yl)boronic acid (5.9 g, 26.5 mmol) were added to 110 ml of toluene, 28 ml of ethanol, and 28 ml of DI water, and stirred. Then, potassium carbonate (9.2 g, 66.5 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.3 g, 1.1 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the resulting solid was filtered. Afterwards, compound 239 (5.7 g, 8.7 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =649

[0328]

[0329] [Synthesis Example 18] Synthesis of the capping layer compound of compound 262

[0330]

[0331] 9H-carbazole (5.0 g, 29.9 mmol) and 7-bromoquinoline (9.3 g, 44.9 mmol) were placed in a two-necked round-bottom flask, and 100 ml of 1,4-dioxane was added and stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 h. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was then used to obtain compound 262-1 (10.3 g, 35.0 mmol) using the ratio of toluene and hexane. MS: [M+H] + =294

[0332] Compound 262-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.3 g, 35.7 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 262-2 (6.4 g, 14.1 mmol). MS: [M+H] + =452

[0333] Compound 262-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole-5-carbonitrile (4.8 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 262 (4.4 g, 7.6 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =579

[0334]

[0335] [Synthesis Example 19] Synthesis of the capping layer compound of compound 301

[0336]

[0337] 9H-carbazole (10.0 g, 59.8 mmol) and 2-bromonaphthalene (18.6 g, 89.7 mmol) were placed in a two-necked round-bottom flask, 200 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (2.8 g, 15.0 mmol), tripotassium phosphate (25.4 g, 119.6 mmol), and 1,2-cyclohexanediamine (4.1 g, 35.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 301-1 (23.7 g, 80.7 mmol) using the ratio of toluene and hexane. MS:[M+H] + =293

[0338] Compound 301-1 (5.0 g, 17.0 mmol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.4 g, 35.8 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 301-2 (7.2 g, 15.9 mmol). MS: [M+H] + =451

[0339] Compound 301-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole (4.0 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 301 (4.6 g, 8.6 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =528

[0340]

[0341] [Synthesis Example 20] Synthesis of the capping layer compound of compound 302

[0342]

[0343] Compounds 301-1 and 301-2 are synthesized in the same manner as in Synthesis Example 19.

[0344] Afterwards, compound 301-2 (5.0 g, 11.1 mmol) and benzo[d]oxazole-5-carbonitrile (4.8 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 302 (4.2 g, 8.0 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =578

[0345]

[0346] [Synthesis Example 21] Synthesis of the capping layer compound of compound 304

[0347]

[0348] Compounds 301-1 and 301-2 are synthesized in the same manner as in Synthesis Example 19.

[0349] Afterwards, compound 301-2 (5.0 g, 11.1 mmol) and benzo[d]thiazole (4.5 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 304 (5.0 g, 9.0 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =560

[0350]

[0351] [Synthesis Example 22] Synthesis of the capping layer compound of compound 307

[0352]

[0353] Compounds 301-1 and 301-2 are synthesized in the same manner as in Synthesis Example 19.

[0354] Afterwards, compound 301-2 (5.0 g, 11.1 mmol) and benzofuran (3.9 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 307 (4.0 g, 7.5 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] +=526

[0355]

[0356] [Synthesis Example 23] Synthesis of the capping layer compound of compound 310

[0357]

[0358] Compounds 301-1 and 301-2 are synthesized in the same manner as in Synthesis Example 19.

[0359] Afterwards, compound 301-2 (5.0 g, 11.1 mmol) and benzo[b]thiophene (4.5 g, 33.2 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.3 mmol), triphenylphosphine (2.9 g, 11.1 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 310 (4.4 g, 7.9 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =558

[0360]

[0361] [Synthesis Example 24] Synthesis of the capping layer compound of compound 320

[0362]

[0363] Compounds 301-1 and 301-2 are synthesized in the same manner as in Synthesis Example 19.

[0364] Afterwards, compound 301-1 (5.0 g, 11.1 mmol), (3',5'-dicyano-[1,1'-biphenyl]-4-yl)boronic acid (6.6 g, 26.6 mmol) were added to 110 ml of toluene, 28 ml of ethanol, and 28 ml of DI water, and stirred. Then, potassium carbonate (9.2 g, 66.5 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.3 g, 1.1 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the produced solid was filtered. Afterwards, compound 320 (6.3 g, 9.0 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =698

[0365]

[0366] [Synthesis Example 25] Synthesis of the capping layer compound of compound 335

[0367]

[0368] 9H-carbazole (5.0 g, 29.9 mmol) and 8-bromoquinoxaline-5-carbonitrile (10.5 g, 44.9 mmol) were placed in a two-necked round-bottom flask, 100 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was complete, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 335-1 (10.2 g, 31.8 mmol) using the ratio of toluene and hexane. MS:[M+H] + =320

[0369] Compound 335-1 (5.0 g, 15.6 mmol) was dissolved in 78 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (5.8 g, 32.8 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 335-2 (6.3 g, 13.3 mmol). MS: [M+H] + =478

[0370] Compound 335-2 (5.0 g, 10.5 mmol) and benzo[d]oxazole (3.7 g, 31.4 mmol) were added to 105 ml of toluene and stirred. Then, potassium carbonate (5.8 g, 41.8 mmol), triphenylphosphine (2.7 g, 10.5 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.2 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 335 (3.6 g, 6.5 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =555

[0371]

[0372] [Synthesis Example 26] Synthesis of the capping layer compound of compound 375

[0373]

[0374] Compounds 335-1 and 335-2 are synthesized in the same manner as in Synthesis Example 25.

[0375]

[0376] *Afterwards, compound 335-2 (5.0 g, 10.5 mmol) and benzo[d]thiazole (4.2 g, 31.4 mmol) were added to 105 ml of toluene and stirred. Then, potassium carbonate (5.8 g, 41.8 mmol), triphenylphosphine (2.7 g, 10.5 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.2 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 375 (4.0 g, 6.8 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =587

[0377]

[0378] [Synthesis Example 27] Synthesis of the capping layer compound of compound 455

[0379]

[0380] Compounds 335-1 and 335-2 are synthesized in the same manner as in Synthesis Example 25.

[0381] Afterwards, compound 335-2 (5.0 g, 10.5 mmol), (4'-cyano-[1,1'-biphenyl]-4-yl)boronic acid (5.6 g, 25.1 mmol) were added to 105 ml of toluene, 26 ml of ethanol, and 26 ml of DI water, and stirred. Then, potassium carbonate (8.7 g, 62.7 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.2 g, 1.0 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the produced solid was filtered. Afterwards, compound 455 (5.7 g, 8.5 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H]+ =675

[0382]

[0383] [Synthesis Example 28] Synthesis of the capping layer compound of compound 491

[0384]

[0385] Place 9H-carbazole (5.0 g, 29.9 mmol) and 2-bromoquinoxaline-6,7-dicarbonitrile (11.6 g, 44.9 mmol) in a two-necked round-bottom flask, add 100 ml of 1,4-dioxane, and stir. Next, add copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol), and reflux at 100°C for 24 hours. After the reaction is complete, remove 1,4-dioxane and filter the resulting solid. Afterwards, the filtered solid was used to obtain compound 491-1 (11.5 g, 33.2 mmol) using the ratio of toluene and hexane. MS: [M+H] + =345

[0386] Compound 491-1 (5.0 g, 14.5 mol) was dissolved in 72 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (5.4 g, 30.4 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 491-2 (6.0 g, 12.0 mmol). MS: [M+H] + =503

[0387] Compound 491-2 (5.0 g, 9.9 mmol) and benzo[d]oxazole (3.6 g, 29.8 mmol) were added to 100 ml of toluene and stirred. Then, potassium carbonate (5.5 g, 39.7 mmol), triphenylphosphine (2.6 g, 9.9 mmol), palladium(II) acetate (0.04 g, 0.2 mmol), and copper(II) acetate (0.7 g, 4.0 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 491 (3.9 g, 6.8 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =580

[0388]

[0389] [Synthesis Example 29] Synthesis of the capping layer compound of compound 505

[0390]

[0391] 9H-carbazole (5.0 g, 29.9 mmol) and 2-bromoquinoline-6-carbonitrile (10.5 g, 44.9 mmol) were placed in a two-necked round-bottom flask, 100 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was complete, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 505-1 (11.6 g, 36.3 mmol) using the ratio of toluene and hexane. MS:[M+H] + =319

[0392] Compound 505-1 (5.0 g, 15.7 mol) was dissolved in 78 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (5.9 g, 32.9 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 505-2 (6.6 g, 13.8 mmol). MS: [M+H] + =477

[0393] Compound 505-2 (5.0 g, 10.5 mmol) and benzo[d]oxazole (3.7 g, 31.4 mmol) were added to 105 ml of toluene and stirred. Then, potassium carbonate (5.8 g, 41.9 mmol), triphenylphosphine (2.7 g, 10.5 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.2 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 505 (4.3 g, 7.8 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =554

[0394]

[0395] [Synthesis Example 30] Synthesis of the capping layer compound of compound 515

[0396]

[0397] 9H-carbazole (5.0 g, 29.9 mmol) and 3-bromoquinoline-6-carbonitrile (10.5 g, 44.9 mmol) were placed in a two-necked round-bottom flask, 100 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was complete, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 515-1 (11.3 g, 35.4 mmol) using the ratio of toluene and hexane. MS:[M+H] + =319

[0398] Compound 515-1 (5.0 g, 15.7 mol) was dissolved in 78 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (5.9 g, 32.9 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 515-2 (6.8 g, 14.2 mmol). MS: [M+H] + =477

[0399] Compound 515-2 (5.0 g, 10.5 mmol) and benzofuran (3.7 g, 31.4 mmol) were added to 105 ml of toluene and stirred. Then, potassium carbonate (5.8 g, 41.9 mmol), triphenylphosphine (2.7 g, 10.5 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.2 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 515 (4.0 g, 7.2 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =552

[0400]

[0401] [Synthesis Example 31] Synthesis of the capping layer compound of compound 533

[0402]

[0403] 9H-carbazole (5.0 g, 29.9 mmol) and 2-bromoquinazoline (9.4 g, 44.9 mmol) were placed in a two-necked round-bottom flask, 100 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 h. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was then used to obtain compound 533-1 (11.3 g, 38.1 mmol) using the ratio of toluene and hexane. MS: [M+H] + =295

[0404] Compound 533-1 (5.0 g, 16.9 mol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.3 g, 35.6 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 533-2 (7.1 g, 15.6 mmol). MS: [M+H] + =453

[0405] Compound 533-2 (5.0 g, 11.0 mmol) and benzo[d]thiazole (4.5 g, 33.1 mmol) were added to 110 ml of toluene and stirred. Then, potassium carbonate (6.1 g, 44.1 mmol), triphenylphosphine (2.9 g, 11.0 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.4 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed, and the resulting solid was filtered. Afterwards, compound 533 (5.1 g, 9.0 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =562

[0406]

[0407] [Synthesis Example 32] Synthesis of the capping layer compound of compound 541

[0408]

[0409] 9H-carbazole (5.0 g, 29.9 mmol) and 6-bromoquinoline-2-carbonitrile (10.5 g, 44.9 mmol) were placed in a two-necked round-bottom flask, 100 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was complete, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was then used to obtain compound 541-1 (11.0 g, 34.5 mmol) using the ratio of toluene and hexane. MS:[M+H] + =319

[0410] Compound 541-1 (5.0 g, 15.7 mol) was dissolved in 85 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (5.9 g, 32.9 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 541-2 (6.3 g, 13.2 mmol). MS: [M+H] + =477

[0411] Compound 541-2 (5.0 g, 10.5 mmol) and benzo[d]thiazole (4.2 g, 31.4 mmol) were added to 105 ml of toluene and stirred. Then, potassium carbonate (5.8 g, 41.9 mmol), triphenylphosphine (2.7 g, 10.5 mmol), palladium(II) acetate (0.05 g, 0.2 mmol), and copper(II) acetate (0.8 g, 4.2 mmol) were added and refluxed at 100°C for 24 hours. After the reaction was completed, toluene was removed and the resulting solid was filtered. Afterwards, compound 541 (4.8 g, 8.3 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =586

[0412]

[0413] [Synthesis Example 33] Synthesis of the capping layer compound of compound 564

[0414]

[0415] 9H-carbazole (5.0 g, 29.9 mmol) and 2-bromo-6-methylnaphthalene (9.9 g, 44.9 mmol) were placed in a two-necked round-bottom flask, 100 ml of 1,4-dioxane was added, and the mixture was stirred. Next, copper(I) iodide (1.4 g, 7.5 mmol), tripotassium phosphate (12.7 g, 59.8 mmol), and 1,2-cyclohexanediamine (2.0 g, 17.9 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, 1,4-dioxane was removed, and the resulting solid was filtered. The filtered solid was used to obtain compound 564-1 (12.0 g, 39.0 mmol) using the ratio of toluene and hexane. MS:[M+H] + =307

[0416] Compound 564-1 (5.0 g, 16.3 mmol) was dissolved in 80 ml of dimethylformamide and stirred at 0°C. N-BromoSuccinimide (6.1 g, 34.2 mmol) was then added and stirred at room temperature for 24 hours. Upon completion of the reaction, methanol was added to form a precipitate, and the resulting solid was filtered to obtain compound 564-2 (6.4 g, 13.8 mmol). MS: [M+H] + =465

[0417] Compound 564-2 (5.0 g, 10.7 mmol) and (4-cyanophenyl)boronic acid (3.8 g, 25.8 mmol) were added to 110 ml of toluene, 28 ml of ethanol, and 28 ml of DI water, and stirred. Then, potassium carbonate (8.9 g, 64.5 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.2 g, 1.1 mmol) were added, and the mixture was refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the resulting solid was filtered. Afterwards, compound 564 (4.5 g, 8.8 mmol) was obtained from the filtered solid by utilizing the ratio of toluene to hexane. MS: [M+H] + =510

[0418]

[0419] [Synthesis Example 34] Synthesis of the capping layer compound of compound 611

[0420]

[0421] Compounds 491-1 and 491-2 are synthesized in the same manner as in Synthesis Example 28.

[0422] Afterwards, compound 491-2 (5.0 g, 9.9 mmol), (4'-cyano-[1,1'-biphenyl]-4-yl)boronic acid (5.3 g, 25.8 mmol) were added to 100 ml of toluene, 25 ml of ethanol, and 25 ml of DI water, and stirred. Then, potassium carbonate (8.2 g, 59.6 mmol) and Tetrakis(triphenylphosphine)-palladium(0) (1.1 g, 1.0 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the produced solid was filtered. Afterwards, compound 611 (5.0 g, 7.2 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] + =700

[0423]

[0424] [Synthesis Example 35] Synthesis of the capping layer compound of compound 613

[0425]

[0426] Compounds 533-1 and 533-2 are synthesized in the same manner as in Synthesis Example 31.

[0427] Afterwards, compound 533-2 (5.0 g, 11.0 mmol), (4'-cyano-[1,1'-biphenyl]-4-yl)boronic acid (5.9 g, 26.5 mmol) were added to 110 ml of toluene, 28 ml of ethanol, and 28 ml of DI water, and stirred. Then, potassium carbonate (9.2 g, 66.2 mmol) and Tetrakis(triphenylphosphine)-palladium(0) (1.3 g, 1.1 mmol) were added, and refluxed at 100°C for 24 hours. After the reaction was completed, the solvent was removed, and the produced solid was filtered. Afterwards, compound 613 (5.4 g, 8.4 mmol) was obtained from the filtered solid by utilizing the ratio of toluene and hexane. MS: [M+H] +=650

[0428]

[0429] Compounds according to the embodiments of the present invention described above can be synthesized by a person skilled in the art with reference to Synthesis Examples 1 to 35.

[0430]

[0431] [Example 1] Manufacturing of an organic light-emitting device comprising compound 3 of the synthesis example

[0432] After washing the ITO with distilled water, it was ultrasonically cleaned with isopropanol, acetone, and methanol, and then dried. Next, it was cleaned for 5 minutes using oxygen plasma, and then the substrate was moved to a vacuum deposition machine. HT-2 doped with HT-1 (3%) was deposited on the ITO electrode at a rate of 100 A hole injection layer is created with a thickness of 1100 HT-2 as a hole transport layer on top of it. It is deposited with a thickness of 75 HT-3 as an electron blocking layer on top. After forming a film with a thickness of , the host BH and dopant BD were added as a blue light-emitting layer at a ratio of 2 wt% of the dopant at 200 Deposited. Afterwards, ET-1 was applied as a hole blocking layer at 60 The membrane was formed, and on top of it, ET-2 and LiQ were added as an electron transport layer in a ratio of 1:1, 270 Deposit. On top of that, Yb and LiF are added as an electron injection layer in a ratio of 2:1, 10 The membrane was made of Ag:Mg in a ratio of 10:1 as a transparent electrode, 120 After that, compound 3 is added as a capping layer at 650 By forming a membrane, an organic light-emitting diode was manufactured.

[0433]

[0434]

[0435]

[0436]

[0437] [Examples 2-35] Manufacturing of an organic light-emitting device comprising the compound of Table 1

[0438] A device was manufactured under the same conditions as in Example 1, except that the capping layer of Example 1 was made using the compound in Table 1 below instead of Compound 3.

[0439] Example Compound Example Compound Example Compound Example 220 Example 14184 Example 26375 Example 321 Example 15200 Example 27455 Example 484 Example 16207 Example 28491 Example 5139 Example 17239 Example 29505 Example 6141 Example 18262 Example 30515 Example 7143 Example 19301 Example 31533 Example 8144 Example 20302 Example 32541 Example 9147 Example 21304 Example 33564 Example 10150 Example 22307 Example 34611 Example 11153 Example 23310 Example 35613 Example 12159 Example 24320 Example 13181 Example 25335

[0440] [Comparative Example 1] A device was manufactured under the same conditions as in Example 1, except that no capping layer was used.

[0441] [Comparative Example 2]

[0442] Except for using Alq3 as the capping layer, the device was manufactured under the same conditions as in Example 1.

[0443]

[0444] [Comparative Example 3]

[0445] Except for using NPB as the capping layer, the device was manufactured under the same conditions as in Example 1.

[0446]

[0447]

[0448] [Experimental Results]

[0449] 10 mA / cm for the organic light emitting devices of Examples 1 to 35 and Comparative Examples 1 to 3 2 The wavelength characteristics of electroluminescence were observed by applying an electric field, and are summarized in Table 2.

[0450] Example Capping Layer Driving Voltage (V) Current Efficiency (cd / A) Power Efficiency (lm / W) CI Ex CIE y Example 1 Compound 3 3.99 9.63 7.58 0.136 0.047 Example 2 Compound 204.06 9.04 7.00 0.139 0.043 Example 3 Compound 214.04 9.14 7.11 0.139 0.043 Example 4 Compound 844.04 9.19 7.15 0.138 0.043 Example 5 Compound 1394.06 8.86 6.86 0.138 0.044 Example 6 Compound 1414.03 9.54 7.44 0.137 0.046 Example 7 Compound 1433.989.247.290.1390.043 Example 8 Compound 1444.169.106.870.1380.044 Example 9 Compound 1474.159.487.180.1370.046 Example 10 Compound 1504.099.517.300.1370.045 Example 11 Compound 1534.159.487.180.1370.046 Example 12 Compound 1594.039.557.440.1370.046 Example 13 Compound 1814.199.617.210.1360.048 Example 14 Compound 1844.059.557.410.1360.047 Example 15 Compound 2004.179.507.160.1370.047 Example 16 Compound 2073.969.067.190.1380.044 Example 17 Compound 2394.159.417.120.1360.048 Example 18 Compound 2624.039.387.310.1360.046 Example 19 Compound 3014.179.507.160.1370.047 Example 20 Compound 3024.029.397.340.1370.045 Example 21 Compound 3044.059.127.070.1380.043 Example 22 Compound 3074.059.006.980.1380.043 Example 23 Compound 3104.049.377.290.1380.044 Example 24 Compound 3204.029.057.070.1380.043 Example 25 Compound 3354.109.327.150.1380.045 Example 26 Compound 3754.079.367.230.1380.045 Example 27 Compound 4554.139.317.090.1380.044 Example 28 Compound 4914.159.487.180.1370.046 Example 29 Compound 5054.069.537.370.1370.045 Example 30 Compound 5154.179.557.190.1360.047 Example 31 Compound 5334.049.557.430.1370.046 Example 32 Compound 5414.189.567.180.1360.047 Example 33 Compound 5644.019.317.300.1370.045 Example 34 Compound 6114.169.467.140.1360.047 Example 35 Compound 6134.009.227.250.1370.045Comparative Example 1-4.066.424.970.1360.050Comparative Example 2Alq34.207.905.910.1390.042Comparative Example 3NPB4.017.826.130.1380.044.

[0451] According to the examples and comparative examples of the present invention, when an organic light-emitting device is manufactured using the compound 1A or 1B of the present invention as a capping layer, the existing problem of total internal reflection and the light generated in the light-emitting layer not being able to escape to the outside, causing the light to be extinguished and the efficiency to be reduced is solved, and in the process of the emitted light being emitted to the outside, the emission performance is greatly increased due to the constructive interference effect, thereby improving the luminous efficiency of the organic light-emitting device. Although the examples have been described with limited drawings as described above, those skilled in the art can apply various technical modifications and variations based on the above. For example, appropriate results can be achieved even if the described techniques are performed in a different order from the described method, and / or components such as the described system, structure, device, circuit, etc. are combined or combined in a different form from the described method, or are replaced or substituted by other components or equivalents.

[0452] Therefore, other implementations, other embodiments, and equivalents to the claims also fall within the scope of the claims described below.

Claims

1. A compound that can be used as a capping layer of a light-emitting device, The compound has a refractive index of 1.7 or more at a wavelength of 380 nm to 730 nm, The above compound is a compound represented by the following chemical formula 1A or chemical formula 1B. [Chemical Formula 1A] [Chemical Formula 1B] (Here, X1 to X7 are each independently selected from CR1 or N, R1 is each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 30 Alkyl group of C1~C 30 Alkoxy group, substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer, substituted or unsubstituted C6~C 60 Diatomic mono- or polycyclic compounds and C1~C 30 Selected from the cylinders of The R1 of multiple CR1s may be independently the same or different, L1 and L2 are each a direct bond or substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic mono- or polycyclic compounds, Ar1 and Ar2 are each substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic mono- or polycyclic compounds, The above substitutions include hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 ) can be selected from the list of 2. In claim 1, The above L1 and L2 are identical to each other, A compound wherein the above Ar1 and Ar2 are identical to each other.

3. In claim 1, A compound wherein Ar1 and Ar2 each independently have a structure represented by the following chemical formula 2A or chemical formula 2B. [Chemical Formula 2A] [Chemical Formula 2B] (Here, X 11 is selected from CR2 or N, X 12 is selected from O, S, NR3, CR4R5, SiR5R6, PR7, S=O, O=S=O, C=O, C=S, Si=O, or Si=S, X 21 Inland X 24 and X 31 Inland X 35 are each independently selected from CR8 or N, R2 to R8 are each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 Selected from the cylinders of The R8 of CR8 are each independently selected and may be the same or different. *- indicates the site that binds to L1 and L2) 4. In claim 3, The above chemical formula 2A is a compound selected from any one of the following chemical formulas 3A to 3E. [Chemical Formula 3A] [Chemical Formula 3B] [Chemical Formula 3C] [Chemical Formula 3D] [Chemical Formula 3E] (Here, R 11 , R 12 are each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 Selected from the cylinders of m is an integer from 0 to 4, Multiple R's 11 ) may be independently the same or different) 5. In paragraph 1, The above compound is, An organic light-emitting device comprising a material represented by at least one of the following chemical formulas 1 to 974. [Compound 1 to Compound 974] 6. A light-emitting device comprising the compound described in claim 1 as a capping layer.

7. In claim 6, A light-emitting device having a thickness of the capping layer of 10 nm to 150 nm.

8. In claim 6, The above light-emitting element includes a hole injection layer, A light-emitting device, wherein the hole injection layer comprises 0.5 wt% to 50 wt% of a p-dopant, and the lowest unoccupied orbital (LUMO) value of the p-dopant is -4.8 eV or less.

9. In claim 6, The above light-emitting element includes at least one of a hole injection layer and a hole transport layer, A light-emitting device, wherein at least one of the hole injection layer and the hole transport layer of the light-emitting device comprises a tertiary aryl amine.

10. In claim 6, The above light-emitting element includes a light-emitting layer, The above light-emitting layer is, A light-emitting device comprising a fluorescent dopant comprising an arylamine ring, a delayed fluorescent dopant comprising a boron ring compound or a nitrile group, a phosphorescent dopant comprising an iridium or platinum complex, or a combination of two or more of the fluorescent dopants, delayed fluorescent dopants, and phosphorescent dopants.

11. In paragraph 6, The above light-emitting element includes an electron transport layer, An organic light-emitting device, wherein the electron transport layer comprises at least one selected from the group consisting of a triazine substituent, a pyridine substituent, a pyrimidine substituent, an oxadiazole substituent, a benzimidazole substituent, and a phenanthroline substituent.

12. A compound that can be used as a capping layer for an organic electroluminescent device, an organic solar cell, an organic thin film transistor, or a device for monochrome or white lighting. The compound has a refractive index of 1.7 or more at a wavelength of 380 nm to 730 nm, The above compound is a compound represented by the following chemical formula 1A or chemical formula 1B. [Chemical Formula 1A] [Chemical Formula 1B] (Here, X1 to X7 are each independently selected from CR1 or N, R1 is each independently hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 30 Alkyl group of C1~C 30 Alkoxy group, substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer, substituted or unsubstituted C6~C 60 Diatomic mono- or polycyclic compounds and C1~C 30 Selected from the cylinders of The R1 of multiple CR1s may be independently the same or different, L1 and L2 are each a direct bond or substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic mono- or polycyclic compounds, Ar1 and Ar2 are each substituted or unsubstituted C6~C 60 A monocyclic or polycyclic compound of the mobilizer and a substituted or unsubstituted C6~C 60 Selected from diatomic mono- or polycyclic compounds, The above substitutions include hydrogen, deuterium, halogen, hydroxyl (-OH), nitro, cyano, C1~C 50 Alkyl group of C1~C 50 Fluoroalkyl group, C1~C 50 Alkenyl group, C1~C 50 Alkynyl group, C1~C 50 Alkoxy group, C6~C 50 Aryl group of C6~C 50 Heteroaryl group and C1~C 50 ) can be selected from the list of 13. A method for manufacturing an organic electroluminescent device, A step of forming a first electrode on a substrate; A step of forming a hole injection layer on the first electrode; A step of forming a hole transport layer on the above hole injection layer; A step of forming a light-emitting layer on the above hole transport layer; A step of forming an electron transport layer on the above light-emitting layer; A step of forming an electron injection layer on the electron transport layer; A step of forming a second electrode on the electron injection layer; and a step of forming a capping layer on the second electrode; A method for manufacturing an organic light-emitting device, wherein the capping layer comprises the compound described in claim 1.

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