KR20200061711A - Organic luminescent compound, producing method of the same and organic electroluminescent device including the same - Google Patents

Abstract

The present invention relates to an organic luminescent compound represented by chemical formula 1. In chemical formula 1, R_1 and R_2 represent hydrogen, substitutable linear or branched C_1-C_20 alkyl, substitutable C_1-C_24 aryl, halogen, cyano, alkoxy, triflowlomethyl, independently; A_1 represents at least one ring selected from or fused polycyclic rings of at least two rings selected from the group consisting of substitutable 5-numbered unsaturated or aromatic ring, substitutable 6-numbered unsaturated or aromatic ring, substitutable 5-numbered unsaturated or aromatic hetero ring, and substitutable 6-numbered unsaturated or aromatic hetero ring; the hetero ring comprises one or more selected from the group consisting of N, O, and S; and the substitution is performed by linear or branched C_1-C_20 alkyl, C_1-C_24 aryl, halogen, cyano, alkoxy, triflowlomethyl.

Description

ORGANIC LUMINESCENT COMPOUND, PRODUCING METHOD OF THE SAME AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME

The present application relates to an organic light emitting compound, a method for manufacturing the same, and an organic electroluminescent device including the same.

Advances in display technology are many, from cathode ray tubes (CRTs), plasma display panels (PDPs), and liquid crystal displays (LCDs) to organic light emitting diodes (OLEDs). Development has been achieved. Of these, OLED is a next-generation display technology that uses self-emissive blue, green, and red organic compounds. In the case of OLED displays made of diode device manufacturing using each light emitting material, it shows excellent characteristics in color reproduction technology, reaction speed, viewing angle, etc., compared to LCDs that realize light using existing color filters and backlights. In particular, it has been receiving attention, and since it is a self-emissive structure that does not use a backlight, it presents an infinite potential for development as a next-generation display such as a foldable and flexible display.

The most important factor for a device using an OLED to have good efficiency is the light emission efficiency of the light emitting molecule itself. Therefore, the development of luminescent molecules with good self-luminous efficiency is one of the important research tasks. Looking from the perspective of the basic structure of the OLED, there is a sequential sandwich structure such as a hole injection layer, a hole transport layer, a light emitting layer, a hole confinement layer, an electron transport layer, an electron injection layer, and a cathode on an anode formed on a transparent electrode substrate. The former moves through the LUMO (Lowest Unoccupied Molecular Orbital) energy level of each layer forming the stacked structure, and the holes move through the HOMO (Highest Occupied Molecular Orbital) energy level of each layer forming the stacked structure to exciton (exciton) in the light emitting layer. ). The energy of the exciton formed is emitted as light energy, and light of red, green, and blue wavelengths is emitted according to each energy difference. At this time, as the exciton is formed, the excited state in the compound can be excited as a singlet state and a triplet state. The singlet state can be formed with a probability of a quarter, and a triplet state with a probability of 3/4. The falling from the singlet excited state to the bottom is called fluorescence, and the falling from the triplet state to the bottom is called phosphorescence. Therefore, depending on the ratio formed, the internal quantum efficiency can be seen as 25% for fluorescence and 75% for phosphorescence.

However, recently, phosphorescence emitting materials with improved luminous efficiency through organometallic compounds, mainly on metals with large atomic numbers, such as iridium (Ir), platinum (Pt), europium (Eu), etc. Have been used as As the phosphorescent material was developed through such a quarterly transition, the theoretical internal quantum efficiency increased up to 100%, making it possible to develop high-efficiency OLED devices.

The actual efficiency of OLED is determined by the external quantum efficiency EQE (External Quantum Efficiency), which is the amount of light emitted to the outside. In the case of external quantum efficiency, EQE can be enhanced by adjusting the balance (γ) of injected charges or by enhancing light extraction efficiency (η coupling). Finally, the ratio of singlet and triplet generation and fluorescence depending on the characteristics of the luminescent material Alternatively, the phosphorescence quantum efficiency determines the final EQE.

In general, through the device structure, injection of holes and charges in the light emitting layer can be controlled in the same manner (γ=1), and the general light extraction efficiency is about 0.2 to 0.3. However, since the generation ratio of singlet and triplet in the OLED device is 1:3, in the case of fluorescent light emitting materials that cannot use triplet exciton, EQE is only 5% to 7.5%. In the case of phosphorescence, however, most of the singlet excitons can be transferred to the triplet state through a quarterly transition. In addition, the probability of radiation transfer from T ₁ to S ₀ can be made 100% possible by spin-orbital coupling by heavy metals such as iridium or platinum with a large atomic number. Therefore, for phosphorescent materials, EQE can reach up to 20% to 30%.

Studies on organometallic compounds on platinum (PT), europium (Eu), and terbium (Tb) have been conducted, but this is due to the higher self-aggregation due to the planar square structure than the organometallic compounds using iridium (Ir). There was a problem because the luminous efficiency was not high. In the case of phosphorescence using a triplet energy level, a blue phosphor having a high energy gap has a limitation in that it is difficult to design, but it has an advantage that it can have higher efficiency than conventional fluorescence through a quarterly transition. Therefore, in the case of red and green, it is necessary to continuously study phosphors.

Korean Patent Publication No. 2011-0125932, which is the background technology of the present application, relates to a blue phosphorescent iridium organic complex compound and an organic electroluminescent device including the same. Specifically, the disclosed patent discloses a blue phosphorescent iridium organic complex compound and an organic electroluminescent device including the same, which improve the function of the iridium organic complex compound, which has many problems such as luminous efficiency, color purity, and electrical stability.

The present application is to solve the problems of the prior art described above, an object of the present invention is to provide an organic light-emitting compound having high luminous efficiency, a method for manufacturing the same, and an organic electroluminescent device including the same.

However, the technical problems to be achieved by the embodiments of the present application are not limited to the technical problems as described above, and other technical problems may exist.

As a technical means for achieving the above technical problem, the first aspect of the present application provides an organic light emitting compound represented by the following Chemical Formula 1.

[Formula 1]

In the above formula 1, R ₁ and R ₂ are each independently hydrogen, a linear or branched C ₁ -C ₂₀ alkyl which may be substituted, C ₁ -C ₂₄ aryl which may be substituted, halogen, cyano, Alkoxy, triflowlomethyl, A ₁ is a 5-membered unsaturated or aromatic ring which may be substituted, a 6-membered unsaturated or aromatic ring which may be substituted, a 5-membered unsaturated or aromatic heterocycle which may be substituted, and which may be substituted One or more rings selected from the group consisting of a 6-membered unsaturated or aromatic hetero ring, or a polycyclic ring in which two or more rings selected from the group are fused, and the hetero ring is a group consisting of N, O and S It includes one or more selected from, and the substitution may be substituted by a linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, alkoxy, trimethylsilyl, ether. It is not limited.

According to one embodiment of the present application, R ₁ and R ₂ are each independently hydrogen, t-butyl, fluoro, trifluoromethyl, cyano, methoxy, and phenyl which can be substituted, and the substitution May be substituted by linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, alkoxy, trimethylsilyl, ether, but is not limited thereto.

According to one embodiment of the present application, A ₁ is a 5-membered unsaturated or aromatic hetero ring that may be substituted, and the hetero ring includes one or more selected from the group consisting of N, O and S, and the substitution is Linear or branched C ₁ -C ₆ alkyl, or may be substituted by C ₆ -C ₂₀ aryl, but is not limited thereto.

According to the exemplary embodiment of the present application, the organic light emitting compound may include any one of the following compounds, but is not limited thereto:

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According to the exemplary embodiment of the present application, the organic light emitting compound may include any one of the following compounds, but is not limited thereto:

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The second aspect of the present application provides a method for producing an organic light emitting compound according to the first aspect, comprising reacting a compound represented by the following formula (2) with a compound represented by the following formula (3).

[Formula 2]

[Formula 3]

In the above formulas 2 and 3, R ₁ and R ₂ are each independently hydrogen, a linear or branched C ₁ -C ₂₀ alkyl which may be substituted, C ₁ -C ₂₄ aryl which may be substituted, halogen, Ano, alkoxy, triflowlomethyl, A ₁ is a 5-membered unsaturated or aromatic ring that may be substituted, a 6-membered unsaturated or aromatic ring that may be substituted, a 5-membered unsaturated or aromatic heterocycle which may be substituted, and One or more rings selected from the group consisting of 6-membered unsaturated or aromatic hetero rings which may be substituted or polycyclic rings in which two or more rings selected from the above group are fused, and X and Y are each independently hydrogen , Halogen, the hetero ring comprises at least one selected from the group consisting of N, O and S, the substitution is linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, It may be substituted with alkoxy, trimethylsilyl, ether, but is not limited thereto.

The third aspect of the present application includes a first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode, wherein the organic layer includes the organic light emitting compound according to the first aspect.

According to the exemplary embodiment of the present application, the organic layer may include a layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and combinations thereof. However, it is not limited thereto.

The above-described problem solving means are merely exemplary and should not be construed as limiting the present application. In addition to the exemplary embodiments described above, additional embodiments may exist in the drawings and detailed description of the invention.

According to the above-described problem solving means of the present application, the organic light emitting compound according to the present application has high thermal and electrochemical stability based on phenyl pyridine. The organic light emitting compound applied to the present invention is 9-(6-phenylpyridin-2-yl)-9H-pyrido[2,3-b]indole(9-(6-phenylpyridin-2-yl)-9H-pyrido[ 2,3-b]indole) can be formed into a hexagonal metal cycle using the basic skeleton as a synthesis of various substituents. In addition, while introducing various substituents, it is possible to adjust the conjugated conjugation length and adjust the three-dimensionality to adjust an appropriate emission wavelength region.

In addition, the organic light emitting compound according to the present invention has developed a tridentate ligand platinum organometallic complex in which the phenyl acetylene moiety with various substituents is rotated about 90 degrees as a result of DFT calculation. Through these DFT calculation results, it is possible to improve the luminous efficiency by reducing the self-aggregation phenomenon beyond the planar square structure of the existing platinum complex, and more effectively reduce the intermolecular interaction compared to the prior art, and through this, self-aggregation It has an excellent effect in reducing color purity and reducing efficiency.

In addition, the organic light emitting compound according to the present application may be advantageous for commercialization of phosphorescence because platinum (Pt) is easier to obtain than iridium (Ir) of the prior art. Furthermore, the organic light emitting compound according to the present application can make a positive contribution to the next generation flat panel display development industry by providing a material that solves the problems of the prior art.

1 is a schematic diagram of an organic electroluminescent device according to an embodiment of the present application.
Figure 2 is a graph showing the UV absorption wavelength of the organic electroluminescent device according to an embodiment and a comparative example of the present application.
3 is a graph showing light emission characteristics of an organic electroluminescent device according to an embodiment and a comparative example of the present application.
Figure 4 is a graph showing the light-emitting properties of the solid state on the film of the organic electroluminescent device according to an embodiment and a comparative example of the present application.

Hereinafter, embodiments of the present application will be described in detail with reference to the accompanying drawings so that those skilled in the art to which the present application pertains may easily practice.

However, the present application may be implemented in various different forms and is not limited to the embodiments described herein. In addition, in order to clearly describe the present application in the drawings, parts irrelevant to the description are omitted, and like reference numerals are assigned to similar parts throughout the specification.

Throughout this specification, when a part is "connected" to another part, this includes not only "directly connected" but also "electrically connected" with another element in between. do.

Throughout this specification, when a member is positioned on another member “on”, “on top”, “top”, “bottom”, “bottom”, “bottom”, it means that a member is on another member. This includes cases where there is another member between the two members as well as when in contact.

Throughout the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless specifically stated to the contrary.

As used herein, the terms “about”, “substantially”, and the like are used in or near the numerical values when manufacturing and material tolerances unique to the stated meanings are presented, to aid understanding of the present application Hazards are used to prevent unreasonable abuse by unscrupulous infringers of the disclosures that are either accurate or absolute. In addition, throughout the present specification, "step of" or "step of" does not mean "step for".

Throughout the present specification, the term “combination of these” included in the expression of the marki form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the marki form, the component. It means to include one or more selected from the group consisting of.

Throughout this specification, the description of “A and/or B” means “A or B, or A and B”.

Throughout the present specification, the term "aromatic ring" is an aromatic hydrocarbon ring group, a C _{6- 30,} e.g., phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthrenyl, triphenyl alkylenyl, perylenyl carbonyl , Chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzocristenyl, anthracenyl, stilbenyl, pyrenyl, and the like, including aromatic rings, and “aromatic heterocycle” means at least one As an aromatic ring containing a hetero element, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, Quinolyl group, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, triazine rings, Indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadia ring Aromatic heterocyclic groups formed from sol ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzoimidazole ring, pyran ring, dibenzofuran ring It means to do.

Throughout this specification, the term “fusion” refers to two or more rings, wherein at least one pair of adjacent atoms is included in two rings.

Throughout the present specification, the term “alkyl” may include linear or branched, saturated or unsaturated C ₁ -C ₆ alkyl, for example methyl, ethyl, propyl, butyl, pentyl, hexyl or their It may include all possible isomers, but may not be limited thereto.

Throughout this specification, the term "aryl" refers to a monovalent functional group formed by the removal of a hydrogen atom present in one or more rings of an arene, C ₆ -C ₆₀ , C ₆ -C ₄₀ , C ₆ -C ₂₀ , or C ₆ -C ₁₄ It may be containing an aryl group, for example, phenyl, biphenyl (biphenyl), terphenyl (terphenyl), naphthyl (naphthyl), anthryl (anthryl), phenan Phenanthryl, pyrenyl, dibenzothiophenyl, dibenzofuranyl, stilbenyl, anthracenyl, perylenyl, or all of these possible It may be an isomer, but may not be limited thereto. The arene is a hydrocarbon group having an aromatic ring, and includes a monocyclic or polycyclic hydrocarbon group, the polycyclic carbon hydrogen group may include one or more aromatic rings and an aromatic ring or a non-aromatic ring as an additional ring. , It may not be limited.

Throughout this specification, the term “halogen” is an element of group 17 of the periodic table, and may include, but is not limited to, F, Cl, Br, or I, for example.

Hereinafter, an organic light emitting compound of the present application, a method of manufacturing the same, and an organic electroluminescent device including the same will be described in detail with reference to embodiments and examples and drawings. However, the present application is not limited to these embodiments and examples and drawings.

The first aspect of the present application provides an organic light emitting compound represented by the following Chemical Formula 1.

[Formula 1]

In the above formula 1, R ₁ and R ₂ are each independently hydrogen, a linear or branched C ₁ -C ₂₀ alkyl which may be substituted, C ₁ -C ₂₄ aryl which may be substituted, halogen, cyano, Alkoxy, triflowlomethyl, A ₁ is a 5-membered unsaturated or aromatic ring which may be substituted, a 6-membered unsaturated or aromatic ring which may be substituted, a 5-membered unsaturated or aromatic heterocycle which may be substituted, and which may be substituted One or more rings selected from the group consisting of a 6-membered unsaturated or aromatic hetero ring, or a polycyclic ring in which two or more rings selected from the group are fused, and the hetero ring is a group consisting of N, O and S It includes one or more selected from, and the substitution may be substituted by a linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, alkoxy, trimethylsilyl, ether. It is not limited.

According to one embodiment of the present application, R ₁ and R ₂ are each independently hydrogen, t-butyl, fluoro, trifluoromethyl, cyano, methoxy, and phenyl which can be substituted, and the substitution May be substituted by linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, alkoxy, trimethylsilyl, ether, but is not limited thereto.

According to one embodiment of the present application, A ₁ is a 5-membered unsaturated or aromatic hetero ring that may be substituted, and the hetero ring includes one or more selected from the group consisting of N, O and S, and the substitution is It may be substituted by a linear or branched C ₁ -C ₆ alkyl, or C ₆ -C ₂₀ aryl, but is not limited thereto.

In the case of the platinum complex, the tetradentate ligand has a planar square structure and has a disadvantage in that efficiency decreases according to the self-aggregation phenomenon. In order to recognize and solve this problem, the present inventors developed a tridentate ligand platinum organometallic complex in which the phenyl acetylene moiety with various substituents is rotated about 90 degrees as a result of DFT calculation.

Through these DFT calculation results, it is possible to improve the luminous efficiency by reducing the self-aggregation phenomenon beyond the planar square structure of the existing platinum complex, which is the existing Ir(ppy) ₃ in the photophysical properties. It exhibits a better quantum yield, so it has better luminous efficiency in device fabrication, so that practical green luminescence can be obtained. That is, it is possible to more effectively reduce the interaction between molecules compared to the prior art, and through this, there is an excellent effect in reducing color purity and reducing efficiency due to self-aggregation.

The present invention is a pure color display panel, an organic light-emitting device and an organic light-emitting compound that can be applied to a flexible and collapsible next-generation display panel, or an organic electric field that can also be applied to power generation through solar cells, indoor and outdoor lighting, etc. It can be applied to a wide range of fields such as light emitting devices and biomarkers. In addition, the organic light emitting compound according to the present application may be advantageous in commercialization of phosphorescence because platinum (Pt) is easier to obtain than iridium (Ir) used in the prior art.

According to the exemplary embodiment of the present application, the organic light emitting compound may include any one of the following compounds, but is not limited thereto:

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According to the exemplary embodiment of the present application, the organic light emitting compound may include any one of the following compounds, but is not limited thereto:

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The second aspect of the present application provides a method for producing an organic light emitting compound according to the first aspect, comprising reacting a compound represented by the following formula (2) with a compound represented by the following formula (3).

With respect to the method for manufacturing the organic light emitting compound according to the second aspect of the present application, detailed descriptions of parts overlapping with the first aspect of the present application have been omitted, but the description of the first aspect of the present application may be omitted even if the description is omitted. The same can be applied to the second aspect.

[Formula 2]

[Formula 3]

In the above formulas 2 and 3, R ₁ and R ₂ are each independently hydrogen, a linear or branched C ₁ -C ₂₀ alkyl which may be substituted, C ₁ -C ₂₄ aryl which may be substituted, halogen, Ano, alkoxy, triflowlomethyl, A ₁ is a 5-membered unsaturated or aromatic ring that may be substituted, a 6-membered unsaturated or aromatic ring that may be substituted, a 5-membered unsaturated or aromatic heterocycle which may be substituted, and One or more rings selected from the group consisting of 6-membered unsaturated or aromatic hetero rings which may be substituted or polycyclic rings in which two or more rings selected from the above group are fused, and X and Y are each independently hydrogen , Halogen, the hetero ring comprises at least one selected from the group consisting of N, O and S, the substitution is linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, It may be substituted with alkoxy, trimethylsilyl, ether, but is not limited thereto.

According to one embodiment of the present application, the reaction may be performed under a solvent, but is not limited thereto.

The solvent is acetic acid, water, ethanol, methanol, propanol, butanol, hexane, methylene chloride, ethyl acetate, propylene glycol, butylene glycol, dipropylene glycol, glycerin, ketone, acetone, dimethyl sulfoxide, dimethylformamide, toluene, Tetrahydrofuran, dichloromethane, acetonitrile, and may include a solvent consisting of a combination thereof, but is not limited thereto.

According to one embodiment of the present application, the reaction may be performed under a catalyst, but is not limited thereto.

The catalyst comprises a metal selected from the group consisting of Pt, Pd, Ni, Rh, Ti, Zr, Hf, V, Ta, Cr, Mo, W, Fe, Ru, Os, Ir and combinations thereof. However, it is not limited thereto.

The third aspect of the present application includes a first electrode; A second electrode; And at least one layer of an organic layer between the first electrode and the second electrode, wherein the organic layer includes the organic light emitting compound according to the first aspect.

For the organic electroluminescent device according to the third aspect of the present application, a detailed description of parts overlapping with the first aspect of the present application is omitted, but even if the description is omitted, the contents described in the first aspect of the present application are the third of the present application. The same can be applied to the side.

According to the exemplary embodiment of the present application, the organic layer may include a layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and combinations thereof. However, it is not limited thereto.

The organic electroluminescent device is, for example, ITO (180 nm) / 4,4', 4″- tris [2-naphthyl (phenyl) amino] triphenylamine (2-TNATA, HIL) (30 nm) / 4,4′-bis[N-(1-naphthyl)-N-phenylamino]-biphenyl (NPB, HTL) (20 nm)/4,4′,4″-tris (carbazo-9-day )-Triphenylamine (TCTA, HTL) (10 nm) / CBP: Green phosphorescent material 1-8 (20 nm, EML)/ 2,2′,2"-(1,3,5-benzyltril)-tris (1-phenyl-1-H-benzimidazole) (TPBi, ETL) (40 nm)/ lithium quinolate (Liq) (2 nm)/Al (100 nm) structure, but is not limited thereto. .

The organic electroluminescent device can be applied to various fields such as indoor and outdoor lighting, photoelectric devices, and solar power generation.

The organic electroluminescent device may be manufactured as follows: a transparent electrode ITO (indium-tin-oxide) thin film (surface resistance 10 Ω/square) obtained from an organic EL glass using acetone, methanol, and distilled water sequentially. After ultrasonic cleaning, it is stored in isopropyl alcohol for 20 minutes and then used after treatment with oxygen plasma. The ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl) is installed in a cell in the vacuum deposition equipment. After adding -4,4'-diamine (NPB) and evacuating until the vacuum in the chamber reaches 5.0 × 10 ^-7 Torr, a current is applied to the cell to evaporate the NPB to about 50 on the ITO substrate. A hole injection layer of nm thickness is deposited. Thereafter, under similar conditions, tris(4-carbazoyl-9-ylphenyl)amine (TCTA) is evaporated to deposit a 10 nm thick hole transport layer. The organic light emitting compound according to the present application is evaporated at a rate of 1.0 Å/sec in the vacuum deposition equipment to deposit a light emitting layer having a thickness of about 20 nm on the hole transport layer. Then, under similar conditions, 2,2',2''-(1,3,5-benzyltri)-tris(1-phenyl-1-H-benzimidazole) (TPBi) and lithium quinolate (Liq) Is sequentially evaporated to deposit an electron transport layer and an electron injection layer having a thickness of about 30 nm and about 2 nm, respectively. Then, an Al cathode having a thickness of 100 nm was deposited using another vacuum deposition equipment to manufacture an organic electroluminescent device.

1 is a schematic diagram of an organic electroluminescent device according to an embodiment of the present application.

The present invention will be described in more detail through the following examples, but the following examples are for illustrative purposes only and are not intended to limit the scope of the present application.

[Example]

Example 1: Synthesis of final compound 1

Example 1-(1): Synthesis of 9H-pyrido[2,3-b]indole (9H-pyrido[2,3-b]indole)

( ¹ H NMR (500 MHz, DMSO) δ 11.78 (s, 1H), 8.50 (dd, J = 7.6, 1.4 Hz, 1H), 8.41 (dd, J = 4.8, 1.6 Hz, 1H), 8.16 (d, J = 7.8 Hz, 1H), 7.54-7.40 (m, 2H), 7.28-7.13 (m, 2H))

Example 1-(2): 9-(6-phenylpyridin-2-yl-9H-pyrido[2,3-b]indole(9-(6-phenylpyridin-2-yl)-9H-pyrido[2 ,3-b]indole)

9H-pyrido[2,3-b]indole (9H-pyrido[2,3-b]indole) obtained in Example 1-(1) above 2.0 g (1.0 eq, 11.9 mmol), copper iodide (Copper Iodide) 0.68 g (0.3 eq, 3.57 mmol), 1,10-phenanthroline (1,10-Phenanthroline) 0.21 g (0.1 eq, 1.19 mmol) and potassium carbonate 4.94 g (3 eq, 35.7 mmol) And dried under vacuum to fill nitrogen gas. After dissolving the compounds in 20 ml of dimethylformamide in the flask, the mixture was stirred under reflux at 160°C for 12 hours. After the reaction, the organic layer was extracted with washing with distilled water and ethyl acetate. It was dried with magnesium sulfate and filtered through diatomaceous earth. After purification through column chromatography, white solid 9-(6-phenylpyridin-2-yl-9H-pyrido[2,3-b]indole (9-) through recrystallization method using methylene chloride and methanol (6-phenylpyridin-2-yl)-9H-pyrido[2,3-b]indole) 2.22 g (yield=58.1%) was obtained ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 8.52 (dd, J = 4.8, 1.6 Hz, 1H), 8.44 (d, J = 8.4 Hz, 1H), 8.39 (dd, J = 7.7, 1.6 Hz, 1H), 8.20 (d, J = 7.9 Hz, 1H), 8.17-8.13 (m, 2H), 8.12 (d, J = 7.7 Hz, 1H), 8.03 (t, J = 7.9 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.54 (ddd, J = 20.0, 11.6, 4.4 Hz, 3H), 7.45 (dd, J = 8.4, 6.2 Hz, 1H), 7.42-7.36 (m, 1H), 7.29 (dt, J = 8.5, 4.3 Hz, 1H))

Example 1-(3): Synthesis of Compound 1-(3)

Platinum (II) chloride (Platinum (II) chloride) 0.83 g (1.0 eq, 3.11 mmol) was placed in a reaction vessel and dried under vacuum to fill with nitrogen gas. 9 ml of benzonitrile was added to the flask to dissolve the compounds, followed by stirring under reflux at 160°C for about 30 minutes. Subsequently, 9-(6-phenylpyridin-2-yl-9H-pyrido[2,3-b]indole obtained in Example 1-(2) above was added to 9 ml of benzonitrile (9-(6- After dissolving 1.0 g (1.0 eq, 3.11 mmol) of phenylpyridin-2-yl)-9H-pyrido[2,3-b]indole), add it to the reaction vessel, and then stir while refluxing at 200°C for about 1 hour 30 minutes. After the reaction was completed, methanol was added to about 20 ml and extracted under reduced pressure.The obtained solid was obtained 1.33 g (yield=80.6%) of compound 1-(3) through column chromatography using methylene chloride. .( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.77 (dd, J = 5.7, 1.3 Hz, 1H), 8.65 (dd, J = 7.6, 1.3 Hz, 1H), 8.20 (d, J = 7.7 Hz, 1H), 8.14 (t, J = 8.1 Hz, 1H), 8.07 (dd, J = 16.3, 8.0 Hz, 2H), 7.89 (d, J = 7.6 Hz, 1H), 7.72 (d, J = 7.7 Hz, 1H), 7.69-7.61 (m, 2H), 7.59-7.51 (m, 2H), 7.28 (td, J = 7.5, 1.3 Hz, 1H), 7.21 (dd, J = 10.7, 4.2 Hz, 1H) )

Example 1-(4): Synthesis of final compound 1

0.8 g (1.0 eq, 1.45 mmol) of the compound obtained in Example 1-(3), 0.27 g (0.8 eq, 1.16 mmol) of copper iodide was placed in a reaction vessel, and vacuum-dried to fill nitrogen gas. After adding 12 ml of triethylamine, 120 ml of methylene chloride and 0.48 ml (3 eq, 4.36 mmol) of phenylacetylene (Phenylacethylene), block the light in the reaction vessel, and then cool the reaction vessel at 0°C for 1 hour. Stir for 30 minutes. After the reaction was completed, the solvent was removed and then dissolved in methylene chloride and separated through column chromatography. Subsequently, the final compound 1 is recrystallized using methylene chloride and methanol. 0.47 g (yield = 52.6%) was obtained. ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.90 (d, J = 5.7 Hz, 1H), 8.60 (d, J = 7.6 Hz, 1H), 8.27 (d, J = 7.5 Hz, 1H), 8.12 (d, J = 7.7 Hz, 1H), 8.07 (t, J = 8.1 Hz, 1H), 7.98 (d, J = 8.5 Hz, 1H), 7.92 (d, J = 8.3 Hz, 1H), 7.73 ( d, J = 7.8 Hz, 1H), 7.62 (d, J = 7.2 Hz, 1H), 7.57 (t, J = 7.3 Hz, 1H), 7.50-7.35 (m, 4H), 7.23 (t, J = 7.6 Hz, 2H), 7.17 (t, J = 6.8 Hz, 1H), 7.14-7.07 (m, 2H).APCI-MS (m/z): 617 [M +1] ⁺ )

Example 2: Synthesis of final compound 2

Example 2-(1): 9-(6-(4-methoxyphenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole(9-(6-(4-methoxyphenyl) Synthesis of pyridin-2-yl)-9H-pyrido[2,3-b]indole)

2-bromo-6-(4-methoxyphenyl)pyridine (2-bromo-6-(4-methoxyphenyl)pyridine) 0.8 g (1.0 eq, 3.02 mmol), 9H- obtained in Example 1-(1) Pyrido[2,3-b]indole (9H-pyrido[2,3-b]indole) 0.51 g (1.0 eq, 3.02 mmol), Copper Iodide 0.17 g (0.3 eq, 0.91 mmol), 1 ,10-Phenanthroline (1,10-Phenanthroline) 0.05 g (0.1 eq, 0.30 mmol) and potassium carbonate 1.26 g (3 eq, 9.09 mmol) were placed in a reaction vessel, dried under vacuum, and filled with nitrogen gas. After dissolving the compounds in 10 ml of dimethylformamide in the flask, the mixture was stirred under reflux at 160°C for 12 hours. After the reaction, the organic layer was extracted with washing with distilled water and ethyl acetate. It was dried with magnesium sulfate and filtered through diatomaceous earth (celite). After purification through column chromatography, 9-(6-(4-methoxyphenyl)pyridin-2-yl)-9H-pyrido[2,3-b through recrystallization method using methylene chloride and methanol. ] 0.75 g of indole (9-(6-(4-methoxyphenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole) was obtained (yield=70.4%). ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 8.52 (dd, J = 4.8, 1.5 Hz, 1H), 8.41 (d, J = 8.4 Hz, 1H), 8.39 (dd, J = 7.7, 1.6 Hz, 1H ), 8.14-8.07 (m, 4H), 7.98 (t, J = 7.9 Hz, 1H), 7.70 (d, J = 7.7 Hz, 1H), 7.55 (dd, J = 11.4, 4.1 Hz, 1H), 7.38 (t, J = 7.5 Hz, 1H), 7.30-7.27 (m, 1H), 7.03 (d, J = 8.8 Hz, 2H), 3.88 (s, 3H))

Example 2-(2): Synthesis of Compound 2-(2)

Platinum (II) chloride (Platinum (II) chloride) 0.33 g (1.0 eq, 1.23 mmol) was placed in a reaction vessel and dried under vacuum to fill with nitrogen gas. 4 ml of benzonitrile was added to the flask to dissolve the compounds, followed by stirring under reflux at 160°C for about 30 minutes. Subsequently, 9-(6-(4-methoxyphenyl)pyridin-2-yl)-9H-pyrido[2,3-b] obtained in Example 2-(1) above was added to 4 ml of benzonitrile. After dissolving 0.43 g (1.0 eq, 1.23 mmol) of indole (9-(6-(4-methoxyphenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole), add it to the reaction vessel. The mixture was stirred under reflux at 200°C for about 1 hour and 30 minutes. After the reaction was completed, about 20 ml of methanol was added, followed by extraction under reduced pressure. 0.50 g (yield=70.3%) of compound 2-(2) was obtained by column chromatography using methylene chloride. ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.69 (d, J = 5.7 Hz, 1H), 8.57 (d, J = 7.6 Hz, 1H), 8.12 (d, J = 7.6 Hz, 1H), 8.02-7.86 (m, 2H), 7.70 (d, J = 8.4 Hz, 1H), 7.64-7.40 (m, 5H), 6.66 (dd, J = 8.6, 2.5 Hz, 1H), 3.82 (s, 3H) )

Example 2-(3): Synthesis of Final Compound 2

0.5 g (1.0 eq, 0.86 mmol) of the compound obtained in Example 2-(2) and 0.13 g (0.8 eq, 0.69 mmol) of copper iodide were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. After adding 7.5 ml of triethylamine, 90 ml of methylene chloride and 0.28 ml (3 eq, 2.58 mmol) of phenylacetylene (Phenylacethylene), the light was blocked in a reaction vessel and stirred at room temperature for 1 hour 30 minutes. After the reaction was completed, the solvent was removed and then separated by column chromatography using methylene chloride. Subsequently, recrystallization using methylene chloride and methanol yielded 0.31 g of the final compound 2 (yield=55.7%). ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.85 (d, J = 5.6 Hz, 1H), 8.57 (dd, J = 7.6, 1.2 Hz, 1H), 8.09 (d, J = 7.6 Hz, 1H ), 8.03-7.74 (m, 4H), 7.74-7.34 (m, 8H), 7.22 (t, J = 7.6 Hz, 2H), 7.12 (t, J = 7.4 Hz, 1H), 6.62 (dd, J = 8.5, 2.6 Hz, 1H), 3.81 (s, 3H).APCI-MS (m/z): 647[M +1] ⁺ )

Example 3: Synthesis of final compound 3

Example 3-(1): 9-(6-(4-tertiary-butylphenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole (9-(6-(4- Synthesis of tert-butylphenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole)

2-(4-tert-butylphenyl)-6-bromopyridine (2-(4-tert-butylphenyl)-6-bromopyridine) 3.88 g (1.5 eq, 13.4 mmol), in Example 1-(1) Obtained 9H-pyrido[2,3-b]indole (9H-pyrido[2,3-b]indole) 1.5 g (1.0 eq, 8.92 mmol), copper iodide 0.51 g (0.3 eq, 2.68 mmol) ), 1,10-phenanthroline (1,10-Phenanthroline) 0.16 g (0.1 eq, 0.82 mmol) and potassium carbonate 13.70 g (3.0 eq, 26.8 mmol) were placed in a reaction vessel, vacuum dried and then filled with nitrogen gas. Dimethyl formamide 10 ml was added to the flask, the compounds were dissolved, and stirred at 160° C. for reflux for 12 hours. After the reaction was completed, the organic layer was extracted with washing with distilled water and ethyl acetate. It was dried with magnesium sulfate and filtered through diatomaceous earth (celite). After purification through column chromatography, 9-(6-(4-tertiary-butylphenyl)pyridin-2-yl)-9H-pyrido[2,3] is obtained by recrystallization using methylene chloride and methanol. -b] Indole (9-(6-(4-tert-butylphenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole) 1.87 g (yield = 55.5%) was obtained. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 8.52 (dd, J = 4.8, 1.5 Hz, 1H), 8.46 (d, J = 8.4 Hz, 1H), 8.39 (dd, J = 7.7, 1.5 Hz, 1H ), 8.17 (d, J = 7.9 Hz, 1H), 8.11 (d, J = 7.6 Hz, 1H), 8.09 (d, J = 8.5 Hz, 2H), 8.00 (t, J = 7.9 Hz, 1H), 7.73 (t, J = 7.7 Hz, 1H), 7.56-7.50 (m, 3H), 7.38 (t, J = 7.4 Hz, 1H), 7.28 (dt, J = 7.8, 3.9 Hz, 1H), 1.38 (s , 9H))

Example 3-(2): Synthesis of Compound 3-(2)

Platinum (II) chloride (Platinum (II) chloride) 0.70 g (1.0 eq, 2.65 mmol) was placed in a reaction vessel and dried under vacuum to fill with nitrogen gas. 10 ml of benzonitrile was added to the flask to dissolve the compounds, followed by stirring under reflux at 160°C for about 30 minutes. Subsequently, 9-(6-(4-tertiary-butylphenyl)pyridin-2-yl)-9H-pyrido[2,3- obtained in Example 3-(1) was added to 10 ml of benzonitrile. b] 1.0 g (1.0 eq, 2.65 mmol) of indole (9-(6-(4-tert-butylphenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole) is dissolved and then reacted After adding to the mixture, the mixture was stirred under reflux for about 1 hour and 30 minutes at 200°C. After the reaction was completed, about 20 ml of methanol was added, followed by extraction under reduced pressure. The obtained solid was obtained 1.09 g (yield=67.7%) of compound 3-(2) through column chromatography using methylene chloride. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 9.84 (d, J = 4.6 Hz, 1H), 8.57 (d, J = 6.5 Hz, 1H), 8.26 (d, J = 1.8 Hz, 1H), 8.13 ( d, J = 7.7 Hz, 1H), 8.05-7.97 (m, 2H), 7.77 (d, J = 8.1 Hz, 1H), 7.60 (dd, J = 14.6, 7.5 Hz, 2H), 7.54-7.45 (m , 3H), 7.22 (dd, J = 8.2, 1.7 Hz, 1H), 1.54 (s, 9H))

Example 3-(3): Synthesis of Final Compound 3

0.5 g (1.0 eq, 0.82 mmol) of the compound obtained in Example 3-(2) at all times, 0.13 g (0.8 eq, 0.69 mmol) of copper iodide were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. After adding 7.5 ml of triethylamine, 75 ml of methylene chloride and 0.30 ml (3.0 eq, 2.47 mmol) of phenylacetylene (Phenylacethylene), block the light in the reaction vessel, and then cool the reaction vessel at 0°C for 1 hour. Stir for 30 minutes. After the reaction is completed, the solvent is removed and then separated through column chromatography using methylene chloride. Thereafter, recrystallization using methylene chloride and methanol gave 0.28 g of the final compound 3 (yield=50.9%). ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 10.03-9.93 (m, 1H), 8.65-8.44 (m, 2H), 8.09 (d, J = 7.6 Hz, 1H), 8.01 (dd, J = 17.2, 8.4 Hz, 2H), 7.84 (d, J = 8.1 Hz, 1H), 7.70-7.37 (m, 7H), 7.31 (t, J = 7.6 Hz, 2H), 7.19 (dd, J = 10.7, 4.4 Hz, 2H), 1.40 (s, 9H).APCI-MS (m/z): 673 [M +1] ⁺ )

Example 4: Synthesis of final compound 4

Example 4-(1): 9-(6-(2,4-difluorophenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole (9-(6-(2 Synthesis of ,4-difluorophenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole)

2-bromo-6-(2,4-difluorophenyl)pyridine (2-bromo-6-(2,4-difluorophenyl)pyridine 2.5 g (1.2 eq, 9.28 mmol), Example 1-(1 9H-pyrido[2,3-b]indole obtained from) 1.3 g (1.0 eq, 7.73 mmol) of 9H-pyrido[2,3-b]indole, 0.44 g of copper iodide (0.3 eq, 2.32 mmol), 1,10-phenanthroline (1,10-Phenanthroline) 0.14 g (0.1 eq, 0.77 mmol) and potassium carbonate 3.21 g (3.0 eq, 23.19 mmol) were placed in a reaction vessel, dried under vacuum, and then nitrogen gas. Dimethylformamide 10 ml was added to the flask, the compounds were dissolved, and stirred at 160° C. for reflux for 12 hours. After the reaction was completed, the organic layer was extracted with washing with distilled water and ethyl acetate. It was dried with magnesium sulfate and filtered through diatomaceous earth (celite). After purification through column chromatography, white solid 9-(6-(2,4-difluorophenyl)pyridin-2-yl)-9H-pyrido[] through recrystallization using methylene chloride and methanol 2,3-b]indole (9-(6-(2,4-difluorophenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole) 0.74 g (yield = 49.7%) was obtained. ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 8.54 (dt, J = 6.6, 3.3 Hz, 1H), 8.47 (dd, J = 7.7, 1.5 Hz, 1H), 8.40 (d, J = 8.3 Hz , 1H), 8.31 (d, J = 8.1 Hz, 1H), 8.21-8.15 (m, 2H), 8.08 (t, J = 7.9 Hz, 1H), 7.83 (dd, J = 7.7, 1.8 Hz, 1H) , 7.57 (dd, J = 11.4, 4.2 Hz, 1H), 7.43 (t, J = 7.5 Hz, 1H), 7.39-7.32 (m, 1H), 7.13-7.00 (m, 2H))

Example 4-(2): Synthesis of Compound 4-(2)

Platinum (II) chloride (Platinum (II) chloride) 0.55 g (1.0 eq, 2.08 mmol) was placed in a reaction vessel and dried under vacuum to fill with nitrogen gas. 8 ml of benzonitrile was added to the flask, the compounds were dissolved, and stirred at 160° C. for reflux for about 30 minutes. Subsequently, 9-(6-(2,4-difluorophenyl)pyridin-2-yl)-9H-pyrido[2,3] obtained in Example 4-(1) was added to 8 ml of benzonitrile. -b] dissolving 1.0 g (1.0 eq, 2.08 mmol) of indole (9-(6-(2,4-difluorophenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole) After being added to the container, the mixture was stirred at reflux for about 1 hour and 30 minutes at 200°C. After the reaction was completed, about 20 ml of methanol was added, followed by extraction under reduced pressure. 0.59 g (yield=48.2%) of compound 4-(2) was obtained from the obtained solid through column chromatography using methylene chloride. ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.65 (d, J = 5.7 Hz, 1H), 8.58 (d, J = 7.6 Hz, 1H), 8.17-8.06 (m, 2H), 8.01 (d , J = 9.5 Hz, 1H), 7.92 (d, J = 8.4 Hz, 1H), 7.83 (d, J = 8.2 Hz, 1H), 7.68-7.42 (m, 4H), 6.65-6.58 (m, 1H) )

Example 4-(3): Synthesis of Final Compound 4

0.5 g (1.0 eq, 0.85 mmol) of the compound obtained in Example 4-(2) and 0.13 g (0.8 eq, 0.68 mmol) of copper iodide were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. After adding 7.5 ml of triethylamine, 75 ml of methylene chloride and 0.28 ml (3.0 eq, 2.56 mmol) of phenylacetylene (Phenylacethylene), block the light in the reaction vessel, and then cool the reaction vessel at 0°C for 1 hour. Stir for 30 minutes. After the reaction was completed, the solvent was removed and then separated through column chromatography using methylene chloride. Subsequently, recrystallization using methylene chloride and methanol gave the final compound 4 0.30 g (yield=52.9%). ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.79 (d, J = 5.7 Hz, 1H), 8.55 (d, J = 7.6 Hz, 1H), 7.93 (m, J = 37.0, 34.6, 21.5, 16.4 Hz, 7H), 7.55 (t, J = 7.8 Hz, 1H), 7.49-7.40 (m, 2H), 7.37 (dd, J = 7.6, 5.7 Hz, 1H), 7.24 (t, J = 7.6 Hz, 2H), 7.13 (t, J = 7.4 Hz, 1H), 6.65-6.45 (m, 1H).APCI-MS (m/z): 653 [M +1] ⁺ )

Example 5: Synthesis of final compound 5

Example 5-(1): 9-(6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole (9-(6-( Synthesis of 4-(trifluoromethyl)phenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole)

2-bromo-6-(4-trifluoromethyl)phenyl)pyridine (2-bromo-6-(4-(trifluoromethyl)phenyl)pyridine 3.5 g (1.0 eq, 11.59 mmol), Example 1-( 1) obtained 9H-pyrido[2,3-b]indole (9H-pyrido[2,3-b]indole) 1.94 g (1.0 eq, 11.59 mmol), copper iodide (Copper Iodide) 0.66 g (0.3 eq , 3.48 mmol), 1,10-phenanthroline (1,10-Phenanthroline) 0.21 g (0.1 eq, 1.16 mmol) and potassium carbonate 4.80 g (3.0 eq, 34.76 mmol) in a reaction vessel, vacuum dried and nitrogen gas Dimethylformamide After dissolving the compounds in 20 ml of the flask, the mixture was stirred under reflux at 160°C for 12 hours. After the reaction was completed, the organic layer was extracted with washing with distilled water and ethyl acetate. It was dried with magnesium sulfate and filtered through diatomaceous earth (celite). After purification through column chromatography, white solid 9-(6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9H-pyrido through recrystallization method using methylene chloride and methanol [2,3-b]indole (9-(6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole) 1.25 g (yield=27.7%) Got. ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 8.55 (dd, J = 4.8, 1.5 Hz, 1H), 8.51-8.43 (m, 2H), 8.39 (d, J = 8.1 Hz, 1H), 8.33 (d, J = 8.3 Hz, 2H), 8.19 (d, J = 7.8 Hz, 1H), 8.12 (t, J = 7.9 Hz, 1H), 7.88 (d, J = 7.7 Hz, 1H), 7.83 (d , J = 8.4 Hz, 2H), 7.60 (t, J = 7.8 Hz, 1H), 7.45 (t, J = 7.5 Hz, 1H), 7.37 (dd, J = 7.7, 4.8 Hz, 1H))

Example 5-(2): Synthesis of Compound 5-(2)

Platinum (II) chloride (Platinum (II) chloride) 0.48 g (1.0 eq, 1.80 mmol) was placed in a reaction vessel and dried under vacuum to fill with nitrogen gas. 8 ml of benzonitrile was added to the flask, the compounds were dissolved, and stirred at 160° C. for reflux for about 30 minutes. Subsequently, 9-(6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9H-pyrido[2, obtained in Example 5-(1) above was added to 8 ml of benzonitrile. After dissolving 1.0 g (1.0 eq, 1.80 mmol) of 3-b]indole (9-(6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-9H-pyrido[2,3-b]indole) After adding to the reaction vessel, the mixture was stirred under reflux at 200°C for about 1 hour and 30 minutes. After the reaction was completed, about 20 ml of methanol was added, followed by extraction under reduced pressure. The obtained solid was obtained by 0.72 g (yield=64.9%) of compound 5-(2) through column chromatography using methylene chloride. ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.70 (d, J = 5.9 Hz, 1H), 8.59 (d, J = 7.5 Hz, 1H), 8.32 (s, 1H), 8.18-8.07 (m , 2H), 7.97-7.86 (m, 2H), 7.73 (d, J = 7.8 Hz, 1H), 7.67-7.46 (m, 4H), 7.35 (d, J = 8.1 Hz, 1H))

Example 5-(3): Synthesis of Final Compound 5

0.5 g (1.0 eq, 0.81 mmol) of the compound obtained in Example 5-(2) and 0.12 g (0.8 eq, 0.65 mmol) of copper iodide were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. After adding 7.5 ml of triethylamine, 75 ml of methylene chloride and 0.27 ml (3.0 eq, 2.42 mmol) of phenylacetylene (Phenylacethylene), block the light in the reaction vessel, and then cool the reaction vessel at 0°C for 1 hour. Stir for 30 minutes. After the reaction was completed, the solvent was removed and then separated through column chromatography using methylene chloride. Subsequently, recrystallization using methylene chloride and methanol gave the final compound 5 0.47 g (yield=85.27%). ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.82-9.75 (m, 1H), 8.61 (d, J = 36.2 Hz, 1H), 8.53 (dd, J = 7.6, 1.3 Hz, 1H), 8.08 (t, J = 8.0 Hz, 2H), 8.00 (d, J = 8.4 Hz, 2H), 7.69 (d, J = 7.6 Hz, 1H), 7.63 (d, J = 8.1 Hz, 1H), 7.54 (t , J = 7.8 Hz, 1H), 7.50-7.40 (m, 3H), 7.39-7.28 (m, 2H), 7.28-7.20 (m, 2H), 7.14 (t, J = 7.4 Hz, 1H).APCI- MS (m/z): 685[M +1] ⁺ )

Example 6: Synthesis of final compound 6

Example 6-(1): 4-(6-(9H-pyrido[2,3-b]indol-9-yl)benzonitrile (4-(6-(9H-pyrido[2,3-b) ]synthesis of indol-9-yl)pyridin-2-yl)benzonitrile)

4-(6-bromopyridin-2-yl)benzonitrile (4-(6-bromopyridin-2-yl)benzonitrile) 0.91 g (1.0 eq, 3.53 mmol), obtained in Example 1-(1) above 9H-pyrido[2,3-b]indole (9H-pyrido[2,3-b]indole) 0.59 g (1.0 eq, 3.53 mmol), Copper Iodide 0.20 g (0.3 eq, 1.06 mmol) , 1,10-phenanthroline (1,10-Phenanthroline) 0.21 g (0.1 eq, 0.35 mmol) and potassium carbonate 1.47 g (3.0 eq, 10.59 mmol) were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. Dimethyl formamide 10 ml was added to the flask, the compounds were dissolved, and stirred at 160° C. for reflux for 12 hours. After the reaction was completed, the organic layer was extracted with washing with distilled water and ethyl acetate. It was dried with magnesium sulfate and filtered through diatomaceous earth (celite). After purification through column chromatography, a white solid 4-(6-(9H-pyrido[2,3-b]indole-9-yl)benzonitrile is obtained by recrystallization using methylene chloride and methanol. 4-(6-(9H-pyrido[2,3-b]indol-9-yl)pyridin-2-yl)benzonitrile) 0.919 g (yield=75.9%) was obtained.( ¹ H NMR (500 MHz, CDCl ₃ ) δ 8.52 (dd, J = 4.8, 1.5 Hz, 1H), 8.40 (dd, J = 7.7, 1.5 Hz, 1H), 8.38 (d, J = 8.4 Hz, 1H), 8.34 (d, J = 8.1 Hz, 1H), 8.26 (d, J = 8.4 Hz, 2H), 8.13 (d, J = 7.7 Hz, 1H), 8.08 (t, J = 7.9 Hz, 1H), 7.80 (m, J = 7.9, 4.9 Hz, 3H), 7.56 (t, J = 7.4 Hz, 1H), 7.41 (t, J = 7.4 Hz, 1H), 7.31 (dd, J = 7.6, 4.8 Hz, 1H))

Example 6-(2): Synthesis of Compound 6-(2)

Platinum (II) chloride (Platinum (II) chloride) 0.38 g (1.0 eq, 1.44 mmol) was placed in a reaction vessel and dried under vacuum to fill with nitrogen gas. 5 ml of benzonitrile was added to the flask to dissolve the compounds, followed by stirring under reflux at 160°C for about 30 minutes. Subsequently, 4-(6-(9H-pyrido[2,3-b]indole-9-yl)benzonitrile (4-() obtained in Example 6-(1) was added to 6 ml of benzonitrile. After dissolving 0.5 g (1.0 eq, 1.44 mmol) of 6-(9H-pyrido[2,3-b]indol-9-yl)pyridin-2-yl)benzonitrile), add it to the reaction vessel, and then add it to The mixture was stirred at reflux for 1 hour and 30 minutes After the reaction was completed, 20 ml of methanol was added, followed by extraction under reduced pressure.The obtained solid was 0.24 g of compound 6-(2) through column chromatography using methylene chloride. (Yield=28.9%).( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.69 (d, 1H), 8.60 (d, J = 7.0 Hz, 1H), 8.37 (s, 1H), 8.15 (d, J = 10.8 Hz, 2H), 7.97-7.92 (t, J = 6.56, 2H), 7.72 (d, J = 8.2 Hz, 2H), 7.64-7.57 (m, 3H), 7.53-7.48 (t , J = 6.85, 2H), 7.40 (d, 1H))

Example 6-(3): Synthesis of final compound 6

The compound obtained in Example 6-(2) 0.24 g (1.0 eq, 0.42 mmol), copper iodide (Copper Iodide) 0.06 g (0.8 eq, 0.34 mmol) was placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. 6.0 ml of triethylamine, 100 ml of methylene chloride and 0.14 ml (3.0 eq, 1.27 mmol) of phenylacetylene were added to the reaction vessel, blocked the light, and then cooled to 0°C for 1 hour. Stir for 30 minutes. After the reaction was completed, the solvent was removed and then separated through column chromatography using methylene chloride. Thereafter, recrystallization using methylene chloride and methanol gave 0.23 g of the final compound 6 (yield=85.2%). ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.70 (d, J = 5.7 Hz, 1H), 8.50 (d, J = 7.6 Hz, 1H), 8.40 (t, J = 15.6 Hz, 1H), 8.13-7.94 (m, 4H), 7.64 (d, J = 7.6 Hz, 1H), 7.54 (t, J = 8.5 Hz, 2H), 7.46 (t, J = 7.5 Hz, 1H), 7.40 (d, J = 7.2 Hz, 2H), 7.30 (ddd, J = 5.6, 3.3, 1.7 Hz, 2H), 7.25 (t, J = 7.6 Hz, 2H), 7.14 (t, J = 7.4 Hz, 1H).APCI-MS (m/z): 642[M +1] ⁺ )

Example 7: Synthesis of final compound 7

Example 7-(1): Preparation of final compound 7

0.7 g (1.0 eq, 1.32 mmol) of the compound obtained in Example 1-(3) and 0.20 g (0.8 eq, 1.05 mmol) of copper iodide were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. Add 11 ml of triethylamine, 100 ml of methylene chloride and 0.71 ml (3 eq, 3.96 mmol) of 1-tert-butyl-4-phenylacetylene (1-tert-butyl-4-ethynylbenzene) to the reaction vessel After blocking the light on, the reaction vessel was cooled to 0°C and stirred for 1 hour 30 minutes. After the reaction was completed, the solvent was removed and then dissolved in methylene chloride and separated through column chromatography. Subsequently, recrystallization using methylene chloride and methanol gave the final compound 7 0.35 g (yield=39.3%). ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.84 (dd, J = 5.6, 1.4 Hz, 1H), 8.54 (dd, J = 7.6, 1.4 Hz, 1H), 8.33-8.16 (t, 1H) , 8.07 (d, J = 7.6 Hz, 1H), 8.02 (t, J = 8.1 Hz, 1H), 7.97 (d, J = 8.4 Hz, 1H), 7.88 (d, J = 8.2 Hz, 1H), 7.66 (d, J = 7.8 Hz, 1H), 7.58 (d, J = 7.2 Hz, 1H), 7.55-7.49 (td, 1H), 7.48-7.31 (m, 4H), 7.30-7.20 (m, 2H), 7.14 (td, J = 7.4, 1.3 Hz, 1H), 7.10-7.04 (td, 1H), 1.27 (s, 9H).APCI-MS (m/z): 673 [M +1] ⁺ )

Example 8: Synthesis of final compound 8

Example 8-(1): Synthesis of Final Compound 8

0.4 g (1.0 eq, 0.75 mmol) of the compound obtained in Example 1-(3) and 0.12 g (0.8 eq, 0.60 mmol) of copper iodide were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. Add 6 ml of triethylamine, 60 ml of methylene chloride and 0.26 ml (3 eq, 2.26 mmol) of 1-ethynyl-4-fluorobenzene to light in the reaction vessel. After blocking, the reaction vessel was cooled to 0°C and then stirred for 1 hour 30 minutes. After the reaction was completed, the solvent was removed and then dissolved in methylene chloride and separated through column chromatography. Subsequently, recrystallization using methylene chloride and methanol gave the final compound 8 0.36 g (yield 76.0%). ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.84 (dd, J = 5.6, 1.5 Hz, 1H), 8.58 (dd, J = 7.6, 1.5 Hz, 1H), 8.22 (dt, J = 30.6, 15.3 Hz, 1H), 8.11 (d, J = 7.7 Hz, 1H), 8.05 (t, J = 8.1 Hz, 1H), 7.97 (d, J = 8.4 Hz, 1H), 7.91 (dd, J = 8.3, 0.7 Hz, 1H), 7.71 (d, J = 7.7 Hz, 1H), 7.60 (d, J = 6.8 Hz, 1H), 7.58-7.52 (m, 1H), 7.50-7.33 (m, 4H), 7.16 ( td, J = 7.4, 1.4 Hz, 1H), 7.09 (td, J = 7.5, 1.3 Hz, 1H), 6.97-6.82 (m, 2H).APCI-MS (m/z): 635 [M +1] ⁺ )

Example 9: Preparation of final compound 9

Example 9-(1): Preparation of final compound 9

0.4 g (1.0 eq, 0.75 mmol) of the compound obtained in Example 1-(3) and 0.12 g (0.8 eq, 0.60 mmol) of copper iodide were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. Add 6 ml of triethylamine, 60 ml of methylene chloride and 0.29 ml (3 eq, 2.26 mmol) of 1-ethynyl-4-methoxybenzene to light in the reaction vessel. After blocking, the reaction vessel was cooled to 0°C and then stirred for 1 hour 30 minutes. After the reaction was completed, the solvent was removed and then dissolved in methylene chloride and separated through column chromatography. Thereafter, recrystallization using methylene chloride and methanol gave 0.22 g of the final compound 9 (yield=45.2%). ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.87 (dd, J = 5.6, 1.3 Hz, 1H), 8.56 (dd, J = 7.6, 1.5 Hz, 1H), 8.33-8.15 (m, 1H) , 8.09 (dd, J = 7.7, 0.6 Hz, 1H), 8.06-7.99 (m, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.89 (dd, J = 8.3, 0.7 Hz, 1H), 7.67 (d, J = 7.8 Hz, 1H), 7.61-7.51 (m, 2H), 7.49-7.42 (m, 1H), 7.41-7.35 (m, 2H), 7.15 (td, J = 7.4, 1.4 Hz, 1H), 7.07 (td, J = 7.5, 1.3 Hz, 1H), 6.83-6.73 (m, 2H), 1.44 (s, 3H).APCI-MS (m/z): 647 [M +1] ⁺ )

Example 10: Preparation of final compound 10

Example 10-(1): Preparation of final compound 10

0.50 g (1.0 eq, 0.82 mmol) of 1-(2-bromophenyl)naphthalene obtained in Example 3-(2) above, 0.06 g of Copper Iodide (0.8 eq, 0.66 mmol) was placed in a reaction vessel, dried under vacuum, and filled with nitrogen gas. 6.0 ml of triethylamine, 75 ml of methylene chloride and 0.45 ml (3.0 eq, 2.47 mmol) of 1-tert-butyl-4-phenylacetylene (1-tert-butyl-4-ethynylbenzene) and reaction vessel After blocking the light on, the reaction vessel was cooled to 0°C and stirred for 1 hour 30 minutes. After the reaction was completed, the solvent was removed and then separated through column chromatography using methylene chloride. Thereafter, recrystallization using methylene chloride and methanol gave 0.21 g (yield=35.0%) of the final compound 10. ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.88 (s, 1H), 8.57 (d, J = 7.3 Hz, 1H), 8.40 (t, J = 25.3 Hz, 1H), 8.09 (d, J = 7.8 Hz, 1H), 8.03-7.92 (m, 2H), 7.85 (d, J = 8.3 Hz, 1H), 7.66 (t, 1H), 7.58-7.34 (m, 8H), 7.12 (d, J = 7.3 Hz, 1H), 1.44 (s, 9H), 1.30 (s, 9H).APCI-MS (m/z): 729 [M +1] ⁺ )

Example 11: Preparation of final compound 11

Example 11-(1): Preparation of final compound 11

0.5 g (1.0 eq, 0.82 mmol) of the compound obtained in Example 3-(2) and 0.13 g (0.8 eq, 0.68 mmol) of copper iodide were placed in a reaction vessel, dried under vacuum, and charged with nitrogen gas. 8.0 ml of triethylamine, 75 ml of methylene chloride and 0.48 ml (3.0 eq, 2.47 mmol) of (4-ethynylphenyl) trimethylsilane were added and the light was blocked in the reaction vessel. After cooling the reaction vessel to 0 ℃ and stirred for 1 hour 30 minutes. After the reaction was completed, the solvent was removed and then separated through column chromatography using methylene chloride. Subsequently, recrystallization using methylene chloride and methanol yielded 0.12 g of the final compound 11 (yield=20.7%). ( ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 9.88 (s, 1H), 8.57 (d, J = 7.3 Hz, 1H), 8.40 (t, J = 25.3 Hz, 1H), 8.09 (d, J = 7.8 Hz, 1H), 8.03-7.92 (m, 2H), 7.85 (d, J = 8.3 Hz, 1H), 7.66 (t, 1H), 7.58-7.34 (m, 8H), 7.12 (d, J = 7.3 Hz, 1H), 1.44 (s, 9H), 1.30 (s, 9H).APCI-MS (m/z): 745 [M +1] ⁺ )

Comparative Example: Ir(ppy)3

Ir(ppy) ₃ Was dissolved in 10 to ⁵ M in a dried toluene solvent, and the solid material was measured in the film state. In the case of a glass film, after soaking in a piranha solution, ultrasonic cleaning for about 30 minutes, followed by washing with distilled water, isopropyl alcohol and acetone, and then drying with nitrogen. Then, a small amount of solid is melted and spin-coated to make a sample. Shimadzu UV-1650PC for UV-spectra measurement, Amincobrowman series 2 luminescence spectrometer for photophysical luminescence measurement, and cell 101.650-QG for liquid samples (all manufactured by German Spectroscopy Co., Ltd.) were used. In the measurement of photophysical properties, the relative luminescence intensity was measured at room temperature in a toluene solution phase diluted with a relative value of the reference material Ir(ppy) ₃ of 1.000 and a solid film state. It was calculated from the UV absorption value based on the excitation light 360 nm and the integral value of the PL emission region.

Experimental Example 1: Measurement of organic electroluminescence properties

For manufacturing an organic electroluminescent device, a glass substrate coated with an indium tin oxide (ITO) thin film is used, and the sheet resistance of the glass substrate to be used is 10 Ω/square and the thickness is 180 nm. The ITO-coated glass was ultrasonically washed in the order of acetone, methanol and distilled water in an ultrasonic bath, then left in isopropanol for 20 minutes and dried using a nitrogen gas gun. The substrate was treated with oxygen plasma in an argon environment. Mounting the ITO-coated glass in the substrate folder of the vacuum deposition equipment, and 2-TNATA (4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine) in a cell in the vacuum deposition equipment. And NPB (4,4′-bis[ N- (1-naphthyl) -N -phenylamino]-biphenyl) and TCTA (4,4′,4″-tris(carbazo-9-yl)-tree Phenylamine). After evacuating until the vacuum degree in the chamber reaches 5.0 × 10 ^-7 Torr, a current is applied to the cell to evaporate the organic layer to deposit a hole injection layer and a hole transport layer of 30, 20, and 10 nm thickness on the ITO substrate, respectively. It was deposited. In addition, CBP (4,4′'-bis( N -carbazolyl)-1,1′'-biphenyl) was used as a host in the vacuum deposition equipment, and the compound synthesized in the following example was 85:15 as a dopant. A light emitting layer having a thickness of 20 nm was deposited on the hole transport layer by evaporating at a rate of 1.0 kPa/sec by doping at a weight of 92:8 and 95:5. Subsequently, TPBi (2,2′,2”-(1,3,5-benzintrile)-tris(1-phenyl-1-H-benzimidazole)) and Liq (lithium quinolate) were sequentially subjected to similar conditions. The electron transport layer and the electron injection layer of 40 nm and 2 nm thickness, respectively, were deposited by evaporation, and all organic materials and metals were deposited under a high vacuum (5.0 x 10 ^-7 Torr). The device was fabricated by depositing an Al cathode to a thickness of 100 nm.

The device according to this experimental example was produced in the following order: ITO (180 nm)/4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA, HIL) (30 nm) / 4,4′-bis[ N -(1-naphthyl)- N -phenylamino]-biphenyl (NPB, HTL) (20 nm)/4,4′,4″-tris (cover Crude-9-day)-triphenylamine (TCTA, HTL) (10 nm) / CBP: green phosphorescent material 1-8 (20 nm, EML)/ 2,2′,2”-(1,3,5- Benzintri)-tris(1-phenyl-1-H-benzimidazole) (TPBi, ETL) (40 nm)/ lithium quinolate (Liq) (2 nm)/ Al (100 nm).

The final compounds 1 to 11 newly synthesized from Examples 1 to 11 were measured by dissolving in 10 to ⁵ M in a dried toluene solvent, and the solid material was measured in a film state. In the case of a glass film, after soaking in a piranha solution, ultrasonic cleaning for about 30 minutes, followed by washing with distilled water, isopropyl alcohol, and acetone, followed by drying with nitrogen. Then, a small amount of solid is melted and spin-coated to make a sample. Shimadzu UV-1650PC for UV-spectra measurement, Amincobrowman series 2 luminescence spectrometer for photophysical luminescence measurement, and cell 101.650-QG for liquid samples (all manufactured by German Spectroscopy Co., Ltd.) were used. In the measurement of photophysical properties, the relative luminescence intensity was measured at room temperature in a toluene solution phase diluted with a relative value of the reference material Ir(ppy) ₃ of 1.000 and a solid film state. As the excitation light, light having a wavelength of 360 nm was used. In addition, the maximum emission wavelength of light emitted by each luminescent organic platinum complex was also measured.

Table 1 is a table on the photophysical properties measured using the final compounds 1 to 11 synthesized in Examples 1 to 11 as a luminescent material.

Organic electroluminescence properties of final compounds 1 to 11 Material UV(λ _max ) ^a
[nm] PL(λ _max ) ^a
[nm] PL(λ _max ) ^b
[nm] E _g ^c
[eV] Relative Luminescence
Intensity ^d Relative Luminescence
Intensity ^e Comparative example Ir(ppy) ₃ 286,384 513 521 2.58 1.0000 1.0000 Example 1 One 301,340,390 501 596 2.60 1.3465 3.8700 Example 2 2 286,334,364 508 606 2.74 0.5908 1.5900 Example 3 3 284,388,396 506 494,530 2.70 1.6098 4.3920 Example 4 4 290,388 494 522 2.79 1.6015 39.8530 Example 5 5 286,330,388 510 503 2.62 1.6056 5.2378 Example 6 6 285,336,408 521 618 2.60 2.2688 11.6018 Example 7 7 284,325,403 504 611 2.62 1.0270 0.5820 Example 8 8 285,320,375 501 532 2.82 0.5280 2.6273 Example 9 9 285,325,366 509 2.65 0.3453 Example 10 10 285,325,403 504 611 2.63 1.027 0.3523 Example 11 11 284,329,402 507 494,530 2.57 1.0183 0.5128

a. Toluene solution (1x10 ^-5 M). b. Solid thin film on quartz plates. c. E _g is the band gap energy estimated from the intersection of absorption and photoluminescence spectra. d. The values of Examples 1 to 11 calculated in comparison with Comparative Example (Ir(ppy) ³ ); (Relative emission intensity = 1.000 in toluene solution (1x10 ^-5 M), λ _ex = 360 nm). e. The values of Examples 1 to 11 calculated in comparison with Comparative Example (Ir(ppy) ³ ); (Relative emission intensity = 1.000 in a thin film, λ _ex = 360 nm)

Figure 2 is a graph showing the UV absorption wavelength of the organic electroluminescent device according to an embodiment and a comparative example of the present application, Figure 3 is a graph showing the light emitting properties of the organic electroluminescent device according to an embodiment and a comparative example of the present application , Figure 4 is a graph showing the light emission characteristics of the solid state on the film of the organic electroluminescent device according to an embodiment and a comparative example of the present application.

The foregoing description of the present application is for illustration, and a person having ordinary knowledge in the technical field to which the present application belongs will understand that it is possible to easily change to other specific forms without changing the technical spirit or essential characteristics of the present application. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined form.

The scope of the present application is indicated by the claims, which will be described later, rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and equivalent concepts should be interpreted to be included in the scope of the present application.

Claims (8)

An organic light-emitting compound represented by Formula 1 below:
[Formula 1]

(In the above formula 1,
R ₁ and R ₂ are each independently hydrogen, substituted linear or branched C ₁ -C ₂₀ alkyl, substituted C ₁ -C ₂₄ aryl, halogen, cyano, alkoxy, triflow Methyl,
A ₁ is a 5-membered unsaturated or aromatic ring that may be substituted, a 6-membered unsaturated or aromatic ring that may be substituted, a 5-membered unsaturated or aromatic heterocycle which may be substituted, and a 6-membered unsaturated or aromatic which may be substituted. One or more rings selected from the group consisting of hetero rings or a polycyclic ring in which two or more rings selected from the group are fused,
The hetero ring includes at least one selected from the group consisting of N, O and S,
The substitution is substituted by linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, alkoxy, trimethylsilyl, ether).
According to claim 1,
R ₁ and R ₂ are each independently hydrogen, t-butyl, fluoro, trifluoromethyl, cyano, methoxy, and phenyl which may be substituted,
The substitution is substituted by a linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, alkoxy, trimethylsilyl, ether.
According to claim 1,
A ₁ is a 5-membered unsaturated or aromatic hetero ring that may be substituted,
The hetero ring includes at least one selected from the group consisting of N, O and S,
The substitution is that of a linear or branched C ₁ -C ₆ alkyl, or C ₆ -C ₂₀ is substituted by aryl, the organic light emitting compound.
According to claim 1,
The organic light-emitting compound, any one of the following compounds, an organic light-emitting compound:

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According to claim 1,
The organic light-emitting compound, any one of the following compounds, an organic light-emitting compound:

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A method for producing the organic light emitting compound according to claim 1, comprising reacting the compound represented by the following formula (2) with the compound represented by the following formula (3):
[Formula 2]

[Formula 3]

(In the above formula 2 and 3,
R ₁ and R ₂ are each independently hydrogen, substituted linear or branched C ₁ -C ₂₀ alkyl, substituted C ₁ -C ₂₄ aryl, halogen, cyano, alkoxy, triflow Methyl,
A ₁ is a 5-membered unsaturated or aromatic ring that may be substituted, a 6-membered unsaturated or aromatic ring that may be substituted, a 5-membered unsaturated or aromatic heterocycle which may be substituted, and a 6-membered unsaturated or aromatic which may be substituted. One or more rings selected from the group consisting of hetero rings or a polycyclic ring in which two or more rings selected from the group are fused,
X and Y are each independently hydrogen or halogen,
The hetero ring includes at least one selected from the group consisting of N, O and S,
The substitution is substituted by linear or branched C ₁ -C ₆ alkyl, C ₆ -C ₂₀ aryl, halogen, alkoxy, trimethylsilyl, ether).
A first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode.
The organic layer comprises an organic light emitting compound according to any one of claims 1 to 5, an organic electroluminescent device.
The method of claim 7,
The organic layer includes a layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and combinations thereof.

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