KR20200003521A - Organic luminescent compound, producing method of the same and organic electroluminescent device including the same - Google Patents

Abstract

The present invention provides an organic light emitting compound represented by chemical formula 1. In chemical formula 1, R_1 is a linear or branched C_1-C_20 alkyl which may be substituted and C_6-C_20 aryl which may be substituted; R_2 is at least one ring selected a group consisting of 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 hetero ring which may be substituted, and a 6-membered unsaturated or aromatic hetero ring which may be substituted or a polycyclic ring in which two or more rings selected from the group are fused; each of A_1 and A_2 is independently at least one ring selected from a group consisting of a 5-membered unsaturated or aromatic hetero ring which may be substituted and a 6-membered unsaturated or aromatic hetero ring which may be substituted; the hetero ring includes one or more selected from a group consisting of N, O, and S; and the substitution may be substituted by alkyl of C_1-C_6 or aryl of C_6-C_20, but is not limited thereto. The present invention provides stable and efficient materials.

Description

Organic light emitting compound, a method of manufacturing the same, and an organic electroluminescent device including the same {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 of manufacturing the same, and an organic electroluminescent device including the same.

Display has become an indispensable element of life, serving as a general information provider of life such as computer, television, and large commercials. Recently, with the development of the display and the improvement of the quality of life, research and development having a complex function for improving the quality of life as well as the existing simple information providing function is required. Accordingly, OLED (Organic Light-Emitting Diode) presents many possibilities and various indicators in future-oriented research such as flexible display and wearable display using thin and light materials. OLED display is a self-luminous display device that can be light and thin, has excellent contrast ratio and viewing angle, and has a fast response speed. In addition, OLED devices have many advantages in the fabrication of flexible and transparent devices, as there is no backlight that takes up a large volume in the LCD compared to liquid crystal display (LCD), which is an important material with OLED as a display material. .

In 1963, the first organic electroluminescent device (OLED) was produced using anthracene single crystal by Pope et al. [M. Pope, HP Kallmamm and P. Magnae. J. Chem. Phys. 38. 2042 (1963). Since then, in 1987, C. Tang and SA VanSlyke have reported a device of a bilayer thin film using Alq ₃ and TPD as the light emitting layer and the charge transporting layer, respectively. Nowadays, development of low molecular OLED displays having improved efficiency and stability using a multi-layered EL device incorporating a charge injection layer and a transport layer is being made.

Currently, OLED devices have fabricated a multi-layered device incorporating electron and hole injection layers and transport layers to improve efficiency and stability. Performance such as luminous efficiency and lifetime are determined by the light emitting materials (red, green, blue) used in such OLED devices. In order to realize the natural color of the light emitting material, the red, green and blue light emitting materials must have high thermal stability, efficiency and color purity.

Luminescent materials are classified into fluorescent materials and phosphorescent materials according to the light emission principle. Basically, electrons are injected from the cathode to move through each layer's Low Unoccupied Molecular Orbital (LUMO) energy level, and holes are injected from the anode to transfer the highest Occupied Molecular Orbital (HOMO) energy level of each layer. It moves through to form an exciton in the emission layer. The exciton formed falls to the ground state and emits light of red, green, and blue wavelengths according to respective energy differences. When electrons and holes are injected in an OLED device, they are divided into singlet excitons and triplet excitons according to the spin direction of the injected electrons, which are generated in a 1: 3 ratio. Fluorescent materials emit light with energy emitted while the singlet excitons, which are 25% of the excitons, become stable to the ground state, while phosphorescent materials emit energy with energy emitted when the triplet excitons, 75% of the excitons, stabilize to the ground state. Say substance.

Phosphors using heavy metals show a theoretical value of 100% of internal quantum efficiency by converting singlet excitons to triplet excitons due to intersystem crossing by spin-orbit coupling. Therefore, in red and green, phosphors using heavy metals have excellent color purity and high efficiency and are used commercially. However, triplet excitons used by phosphors have lower energy levels than singlet excitons due to exchange energy stabilization, which results in relatively wider energy band gaps than red and green light emitting materials. There is a disadvantage in that blue light emission does not obtain good color purity and shortens the life of the device.

In order to develop a light emitting material that realizes a dark blue color, many studies have been conducted on aromatic compounds such as anthracene, fluorene, and pyrene. In the case of phenanthrene, it is known that a flat and rigid molecular structure emits a wavelength in the blue region and has thermal and electrochemical stability, and many studies have been conducted. However, due to its own flat structure, the interaction between the molecules has a disadvantage in that the excimer is formed well, the concentration disappearance phenomenon and the stoke movement occur well. To solve this problem, studies have been conducted to supplement the structure of the flat phenanthrene by substituting different functional groups of the phenanthrene group [J. Mater. Chem. C., (2016), 4, 9310-9315]. In addition, the introduction of bulky amine groups in indenophenanthrene not only enabled effective injection and transport of electric charges, but also researches on the development of light emitting elements having pure blue color coordinates through conversion to warped structures. Days and Pigments, (2017), 144, 9-16. In order to further improve the characteristics of the organic EL device, there is a continuous need for development of more stable and efficient materials that can be used in the organic EL device.

Korean Patent Laid-Open Publication No. 2004-0072004, which is a background technology of the present application, relates to a light emitting compound for an organic light emitting device and an organic light emitting device using the same. However, this publication does not mention compounds in which a substituent is introduced at the 4-position of the phenyl linkage bonded to the imidazole 2-position.

The present application is to solve the above-mentioned problems of the prior art, an object of the present invention to provide an organic light emitting compound, a method for manufacturing the same and an organic electroluminescent device comprising the same.

However, the technical problem to be achieved by the embodiments of the present application is 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 formula (1).

[Formula 1]

In Chemical Formula 1, R ₁ may be substituted, linear or branched C ₁ -C ₂₀ alkyl, substituted C ₆ -C ₂₀ aryl, R ₂ may be substituted 5-membered unsaturated Or at least one selected from the group consisting of an aromatic ring, a 6-membered unsaturated or aromatic ring which may be substituted, a 5-membered unsaturated or aromatic hetero ring which may be substituted and a 6-membered unsaturated or aromatic hetero ring which may be substituted Or a polycyclic ring in which two or more rings selected from the group are fused, A ₁ and A ₂ are each independently a substituted 5-membered unsaturated or aromatic hetero ring and a substituted 6-membered unsaturated or a ring at least one selected from the group consisting of aromatic heterocycle, wherein the heterocycle comprises at least one selected from the group consisting of N, O and S, wherein the substitution is C ₁ -C ₆ It may be substituted by alkyl or C ₆ -C ₂₀ aryl, but is not limited to this.

According to an embodiment of the present disclosure, R ₁ is a single bond, methyl, phenyl which may be substituted, biphenyl, chrysene, phenanthrene, naphthyl, fluorenyl, quinoline, perylene, pyrene and combinations thereof It includes one selected from the group consisting of, the substitution may be substituted by linear or branched C ₁ -C ₂₀ alkyl, but is not limited thereto.

According to an embodiment of the present disclosure, R ₂ is phenoxazine, phenoxyazine, dimethylacridin, diphenylacridine, carbazole, phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, Selected from the group consisting of pyrene, fluoranthene, chrysene, benzofluoranthene, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiophene, dibenzofuran and combinations thereof It may be to include a material, but is not limited thereto.

According to an embodiment of the present disclosure, A ₁ and A ₂ may be each independently, a material selected from the group consisting of pyridine, pyrimidine, pyrrole, carbazole, quinoline, and combinations thereof, It is not limited to this.

According to an embodiment of the present disclosure, 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 is a method for producing an organic light emitting compound according to the first aspect comprising reacting a compound represented by the following formula (2), a compound represented by the following formula (3) and a compound comprising pyridine in the presence of an ammonium salt To provide.

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3, R ₁ may be substituted, linear or branched C ₁ -C ₂₀ alkyl, substituted C ₆ -C ₂₀ aryl, and R ₂ may be substituted 5- 1 selected from the group consisting of circularly unsaturated or aromatic rings, optionally substituted 6-membered unsaturated or aromatic rings, optionally substituted 5-membered unsaturated or aromatic hetero rings and optionally substituted 6-membered unsaturated or aromatic hetero rings At least two rings or at least two rings selected from the group are fused polycyclic rings, wherein the hetero ring includes at least one selected from the group consisting of N, O, and S, and the substitution of C ₁ -C ₆ It may be substituted by alkyl or C ₆ -C ₂₀ aryl, but is not limited thereto.

According to an embodiment of the present disclosure, R ₁ is a single bond, methyl, phenyl which may be substituted, biphenyl, chrysene, phenanthrene, naphthyl, fluorenyl, quinoline, perylene, pyrene and combinations thereof It includes one selected from the group consisting of, the substitution may be substituted by linear or branched C ₁ -C ₂₀ alkyl, but is not limited thereto.

According to an embodiment of the present disclosure, R ₂ is phenoxazine, phenoxyazine, dimethylacridin, diphenylacridine, carbazole, phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, Selected from the group consisting of pyrene, fluoranthene, chrysene, benzofluoranthene, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiophene, dibenzofuran and combinations thereof It may be to include a material, but is not limited thereto.

According to an embodiment of the present disclosure, the compound containing pyridine is 1,2-di (pyridin-2-yl) ethane-1,2-dione (1,2-di (pyridine-2-yl) ethane-1 , 2-dione), but is not limited thereto.

According to one embodiment of the present invention, the ammonium salt is a group consisting of ammonium acetate, ammonium fluoride, ammonium chloride, ammonium bromide, ammonium iodide, ammonium cyanide, ammonium nitrate, ammonium sulfate, ammonium carbonate and combinations thereof It may be to include an ammonium salt selected from, 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.

According to one embodiment of the present application, 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 But may include, but are not limited to, a solvent comprising side, dimethylformamide, toluene, tetrahydrofuran, dichloromethane, acetonitrile and combinations thereof.

The third aspect of the present application provides an organic electroluminescent device comprising the organic light emitting compound according to the present application.

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

According to the above-mentioned means for solving the problem of the present application, the organic light emitting compound according to the present application has a high thermal and electrochemical stability because the base skeleton is a pyridine-bonded imidazole. For example, by introducing pyridine into the imidazole, the organic light emitting compound has a high thermal decomposition temperature (T _d ) and a glass transition temperature (T _g ) to have high thermal stability.

The organic light emitting compound according to the present invention has a variety of compounds such as phenoxazine, phenoxycazine, dimethylacridin, carbazole and the like at the 4-position of the phenyl linkage linked to the imidazole 2-position, centered on the imidazole into which the pyridine is introduced. Substitution of the compound increases the dihedral angle between the phenyl links and at the same time the molecule is distorted. This makes it possible to have more three-dimensional molecular orbital (molecular orbital) than in planar molecules and to increase the mutual repulsion between molecules effectively prevent the intermolecular interaction. As the interaction between molecules is reduced, color purity and luminous efficiency can be improved by preventing the formation of excimers or self-extinction. The energy gap can be adjusted to a shorter conjugation length to induce an appropriate emission wavelength region, particularly a blue emission wavelength region of the device. For example, since pyridine-induced imidazole is used as a basic skeleton, energy levels can be controlled by introducing various substituents, and in particular, fine color purity can be controlled in the blue region.

In addition, by having a distorted structure of the molecule, it is possible to efficiently separate the HOMO and LUMO energy levels of the molecule itself, thereby exhibiting the intrinsic properties of the material, and to prevent the phenomenon that the color purity of light due to the self-aggregation phenomenon in the solid state falls. have.

Furthermore, the organic light emitting compound may exhibit a better life due to the characteristics of delayed fluorescent light.

The organic light emitting compound according to the present invention can make a great contribution to the development of next-generation OLED materials by solving the problems of the prior art and providing an organic light emitting compound having excellent efficiency and color purity.

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

DETAILED DESCRIPTION Hereinafter, exemplary embodiments of the present disclosure will be described in detail with reference to the accompanying drawings so that those skilled in the art may easily implement the present disclosure.

As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention. In the drawings, parts irrelevant to the description are omitted for simplicity of explanation, and like reference numerals designate like 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 said to be located on another member "on", "upper", "top", "bottom", "bottom", "bottom", this means that any member This includes not only the contact but also the presence of another member between the two members.

Throughout this specification, when a part is said to "include" a certain component, it means that it can further include other components, without excluding the other components unless specifically stated otherwise.

As used herein, the terms "about", "substantially", and the like, are used at, or in proximity to, the numerical values of the preparations and material tolerances inherent in the meanings referred to and aid the understanding herein. In order to prevent the unfair use of unscrupulous infringers. In addition, throughout this specification, "step to" or "step of" does not mean "step for."

Throughout this specification, the term "combination of these" included in the expression of the makushi form means one or more mixtures or combinations selected from the group consisting of constituents described in the expression of the makushi form, wherein the constituents It means to include one or more selected from the group consisting of.

 Throughout this specification, description of "A and / or B" means "A or B or A and B."

Throughout this specification, the term "aromatic ring" refers to a C _6-30 aromatic hydrocarbon ring group, for example, phenyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, perrylenyl Means an aromatic ring, such as chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzocrisenyl, anthracenyl, stilbenyl, pyrenyl, and the like. As an aromatic ring containing a hetero element, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindoleyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, Quinolyl groups, isoquinolyl, quinoxalinyl, carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, triazine rings, Indole ring, quinoline ring, acridingo , Pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole It is meant to include aromatic heterocyclic groups formed from rings, thiadiazole rings, benzothiazole rings, triazole rings, imidazole rings, benzoimidazole rings, pyran rings, dibenzofuran rings.

Throughout this specification, the term “fusion” means that, with respect to two or more rings, at least one pair or more adjacent atoms are included in two rings.

Throughout this 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 be to include all possible isomers, but may not be limited thereto.

Throughout this specification, the term “halogen” is a Group 17 element of the periodic table, which may include, for example, F, Cl, Br, or I, but may not be limited thereto.

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

The 1st side of this application relates to the organic light emitting compound represented by following formula (1).

[Formula 1]

In Chemical Formula 1, R ₁ may be substituted, linear or branched C ₁ -C ₂₀ alkyl, substituted C ₆ -C ₂₀ aryl, R ₂ may be substituted 5-membered unsaturated Or at least one selected from the group consisting of an aromatic ring, a 6-membered unsaturated or aromatic ring which may be substituted, a 5-membered unsaturated or aromatic hetero ring which may be substituted and a 6-membered unsaturated or aromatic hetero ring which may be substituted Or a polycyclic ring in which two or more rings selected from the group are fused, A ₁ and A ₂ are each independently a substituted 5-membered unsaturated or aromatic hetero ring and a substituted 6-membered unsaturated or a ring at least one selected from the group consisting of aromatic heterocycle, wherein the heterocycle comprises at least one selected from the group consisting of N, O and S, wherein the substitution is C ₁ -C ₆ It may be substituted by alkyl or C ₆ -C ₂₀ aryl, but is not limited to this.

According to an embodiment of the present disclosure, R ₁ is a single bond, methyl, phenyl which may be substituted, biphenyl, chrysene, phenanthrene, naphthyl, fluorenyl, quinoline, perylene, pyrene and combinations thereof It includes one selected from the group consisting of, the substitution may be substituted by linear or branched C ₁ -C ₂₀ alkyl, but is not limited thereto.

According to an embodiment of the present invention, R ₂ is phenoxazine, phenoxazine, phenoxthiazine, dimethylacridine, dimethylacridine, diphenylacridine, carbazole, Phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, pyrene, fluoranthene, chrysene, benzofluoranthene, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiene It may include, but is not limited to, a substance selected from the group consisting of offen, dibenzofuran and combinations thereof.

R ₂ may serve as an electron donor, but is not limited thereto.

The organic light emitting compound according to the present invention may be based on a light emitting compound of a derivative of imidazole incorporating pyridine, but is not limited thereto.

The organic light emitting compound according to the present invention has high thermal and electrochemical stability because it is based on a pyridine-bonded imidazole. For example, by introducing pyridine into the imidazole, the organic light emitting compound has a high thermal decomposition temperature (T _d ) and a glass transition temperature (T _g ) to have high thermal stability.

The organic light emitting compound according to the present invention has a variety of compounds such as phenoxazine, phenoxycazine, dimethylacridin, carbazole and the like at the 4-position of the phenyl linkage linked to the imidazole 2-position, centered on the imidazole into which the pyridine is introduced. Substitution of the compound increases the dihedral angle between the phenyl links and at the same time the molecule is distorted. This makes it possible to have more three-dimensional molecular orbital (molecular orbital) than in planar molecules and to increase the mutual repulsion between molecules effectively prevent the intermolecular interaction. As the interaction between molecules is reduced, color purity and luminous efficiency can be improved by preventing the formation of excimers or self-extinction. The energy gap can be adjusted to a shorter conjugation length to induce an appropriate emission wavelength region, particularly a blue emission wavelength region of the device. For example, since pyridine-induced imidazole is used as a basic skeleton, energy levels can be controlled by introducing various substituents, and in particular, fine color purity can be controlled in the blue region.

In addition, by having a distorted structure of the molecule, it is possible to efficiently separate the HOMO and LUMO energy levels of the molecule itself, thereby exhibiting intrinsic properties of the material, and to prevent the phenomenon that the color purity of light due to self-aggregation in the solid state falls. have.

Furthermore, the organic light emitting compound may exhibit a better life due to the characteristics of delayed fluorescent light.

The organic light emitting compound according to the present invention can make a great contribution to the development of next-generation OLED materials by solving the problems of the prior art and providing an organic light emitting compound having excellent efficiency and color purity.

The organic light emitting compound may make a positive contribution to the development of next-generation displays such as flat panel displays and flexible displays.

According to an embodiment of the present disclosure, A ₁ and A ₂ may be each independently, a material selected from the group consisting of pyridine, pyrimidine, pyrrole, carbazole, quinoline, and combinations thereof, It is not limited to this.

A ₁ and A ₂ may be each independently, a position of N, O, or S in a hetero ring may be ortho-, meta-, or para-, but is not limited thereto. It doesn't happen. For example, when A ₁ and A ₂ are pyridine, each position of N may be independently ortho-, meta-, or para-, but is not limited thereto. It doesn't happen.

The organic light emitting compound may include the following compound, but is not limited thereto.

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

In a second aspect of the present application, the second aspect of the present application, comprising a reaction of a compound represented by the following formula (2), a compound represented by the following formula (3) and a compound containing pyridine in the presence of an ammonium salt It relates to a method for producing an organic light emitting compound.

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3, R ₁ may be substituted, linear or branched C ₁ -C ₂₀ alkyl, substituted C ₆ -C ₂₀ aryl, R ₂ may be substituted 5- 1 selected from the group consisting of circularly unsaturated or aromatic rings, optionally substituted 6-membered unsaturated or aromatic rings, optionally substituted 5-membered unsaturated or aromatic hetero rings and optionally substituted 6-membered unsaturated or aromatic hetero rings At least two rings or at least two rings selected from the group are fused polycyclic rings, wherein the hetero ring includes at least one selected from the group consisting of N, O, and S, and the substitution of C ₁ -C ₆ It may be substituted by alkyl or C ₆ -C ₂₀ aryl, but is not limited thereto.

According to an embodiment of the present disclosure, R ₁ is a single bond, methyl, phenyl which may be substituted, biphenyl, chrysene, phenanthrene, naphthyl, fluorenyl, quinoline, perylene, pyrene and combinations thereof It includes one selected from the group consisting of, the substitution may be substituted by linear or branched C ₁ -C ₂₀ alkyl, but is not limited thereto.

According to an embodiment of the present disclosure, R ₂ is phenoxazine, phenoxyazine, dimethylacridin, diphenylacridine, carbazole, phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, Selected from the group consisting of pyrene, fluoranthene, chrysene, benzofluoranthene, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiophene, dibenzofuran and combinations thereof It may be to include a material, but is not limited thereto.

R ₂ may serve as an electron donor, but is not limited thereto.

According to an embodiment of the present disclosure, the compound containing pyridine is 1,2-di (pyridin-2-yl) ethane-1,2-dione (1,2-di (pyridine-2-yl) ethane-1 , 2-dione), but is not limited thereto.

The compound represented by Chemical Formula 2 may be one containing aniline, but is not limited thereto.

According to one embodiment of the present invention, the ammonium salt is ammonium acetate (ammonium acetate), ammonium fluoride, ammonium chloride, ammonium bromide, ammonium iodide, ammonium cyanide, ammonium nitrate, ammonium sulfate, ammonium carbonate and combinations thereof It may be to include an ammonium salt selected from the group consisting of, 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.

According to one embodiment of the present application, 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 But may include, but are not limited to, a solvent comprising side, dimethylformamide, toluene, tetrahydrofuran, dichloromethane, acetonitrile and combinations thereof.

The reaction may be performed under a catalyst, but is not limited thereto.

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

For the organic electroluminescent device according to the third aspect of the present application, detailed descriptions of portions overlapping with the first side of the present application are omitted. However, the descriptions of the first aspect of the present application are not described herein. The same can be applied to the side.

The third aspect of the present application provides an organic electroluminescent device comprising the organic light emitting compound according to the present application.

The organic electroluminescent device is for example ITO (150 nm) / 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB, HIL) (50 nm) / 4,4 ', 4' '-tris (carbazo-9-yl) -triphenylamine (TCTA, HTL) (10 nm) / the organic light emitting compound (EML) (20 nm) / 2,2', 2 ''-(1,3,5-benzintril) -tris (1-phenyl-1-H-benzimidazole) (TPBi, ETL) (30 nm) / lithium quinolate (Liq, EIL) (2 nm) It may have a structure of / Al (100 nm), but is not limited thereto.

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

The organic electroluminescent device may be manufactured as follows: A transparent electrode indium-tin-oxide (ITO) thin film (sheet resistance 10 Ω / square) obtained from glass for organic EL is sequentially prepared using acetone, methanol, and distilled water. After ultrasonic cleaning, it is stored in isopropyl alcohol for 20 minutes before use. The ITO substrate was placed in the substrate folder of the vacuum deposition equipment, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB) was placed in a cell in the vacuum deposition equipment, After evacuating until the vacuum in the chamber reaches 5.0 × 10 ⁻⁷ Torr, current is applied to the cell to evaporate the NPB to deposit a hole injection layer of about 50 nm thickness on the ITO substrate. The 4,4 ', 4''-tris (carbazo-9-yl) -triphenylamine (TCTA) is then evaporated under similar conditions to deposit a 10 nm thick hole transport layer. The organic light emitting compound according to the present invention is evaporated at a rate of 1.0 μs / 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-benzintril) -tris (1-phenyl-1-H-benzimidazole) (TPBi) and lithium quinolate (Liq) Are 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. Thereafter, an Al cathode having a thickness of 100 nm is deposited by using another vacuum deposition apparatus to manufacture an organic EL device.

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

Hereinafter, the present invention will be described in more detail with reference to 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 10- (4- (1-phenyl-4,5-di (perridin-2-yl) -1H-imidazol-2-yl) phenyl) -10H-phenoxazine (10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -10H-phenoxazine) Synthesis

Example 1- (1): Synthesis of 10- (4-bromophenyl) -10H-phenoxazine (10- (4-bromophenyl) -10H-phenoxazine)

1.4 g (1.0 eq, 7.64 mmol) of 10-phenoxazine, 2.81 g (1.3 eq, 9.93 mmol) of 1-bromo-4-iodobenzene, 0.25 g (0.25 eq) of Cu powder , 3.97 mmol), 0.16 g (0.08 eq, 0.61 mmol) of 18-crown-6 and 4.22 g (4.0 eq, 30.56 mmol) of potassium carbonate were placed in a reaction vessel and vacuum dried, followed by nitrogen gas. 15 ml of 1,2-dichlorobenzene was added to the reaction vessel to dissolve the compounds, and the mixture was stirred under reflux at a temperature of 180 ° C to 200 ° C. After completion of the reaction, the solvent was evaporated after filtration through celite using dichloromethane. Then, column chromatography gave 2.06 g (yield = 79.46%) of 10- (4-bromophenyl) -10H-phenoxazine. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 7.75-7.70 (m, 2H), 7.25-7.22 (m, 2H), 6.67 (dtd, J = 9.2, 7.8, 1.6 Hz, 4H), 6.60 (td, J = 7.6, 1.7 Hz, 2H), 5.94-5.88 (m, 2H)

Example 1- (2): Synthesis of 4- (10H-phenoxazin-10-yl) benzaldehyde (4- (10H-phenoxazin-10-yl) benzaldehyde)

1.50 g (1.0 eq, 4.44 mmol) of 10- (4-bromophenyl) -10H-phenoxazine obtained in the above Example 1- (1) was placed in a reaction vessel, and vacuum dried and filled with nitrogen gas. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 10.11 (s, 1H), 8.16-8.08 (m, 2H), 7.62-7.51 (m, 2H), 6.71 (dtd, J = 9.3, 7.9, 1.6 Hz, 4H), 6.61 (ddd, J = 17.8, 10.1, 6.1 Hz, 2H), 5.96 (dd, J = 8.0, 1.4 Hz, 2H))

Example 1- (3): 10- (4- (1-phenyl-4,5-di (perridin-2-yl) -1H-imidazol-2-yl) phenyl) -10H-phenoxazine (10 -(4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -10H-phenoxazine) Synthesis

0.40 g (1.0 eq, 1.39 mmol), 1,2-di (pyridin-2-yl) ethane-1, 4- (10H-phenoxazin-10-yl) benzaldehyde obtained in Example 1- (2) above 0.295 g (1.0 eq, 1.39 mmol) of 2,2-dione, 0.65 g (5.0 eq, 6.96 mmol) of aniline, and 1.33 g (12.4 eq, 17.26 mmol) of ammonium acetate were placed in a reaction vessel and vacuum dried, followed by nitrogen gas. 9 ml of acetic acid was added to the reaction vessel to dissolve the compounds, and the mixture was stirred under reflux for 12 hours at a temperature of 120 ° C. After completion of the reaction, neutralization was performed using an aqueous sodium hydroxide solution, washed with distilled water, and an organic layer was extracted with chloroform. Dried over anhydrous magnesium sulfate, filtered through celite, and then purified by column chromatography to give the compound 10- (4- (1-phenyl-4,5-di (perridin-2-yl) -1H-imidazole-2- Il) phenyl) -10H-phenoxazine was obtained 0.52 g (yield = 67.50%). ( ¹ H NMR (500 MHz, CDCl 3) δ 8.49 (dd, J = 24.3, 4.8 Hz, 2H), 7.84 (d, J = 8.0 Hz, 1H), 7.72-7.66 (m, 2H), 7.64 (t, J = 7.7 Hz, 1H), 7.58 (t, J = 7.7 Hz, 1H), 7.40 (d, J = 7.8 Hz, 1H), 7.30 (dd, J = 8.1, 2.9 Hz, 3H), 7.25-7.19 ( m, 4H), 7.17-7.09 (m, 2H), 6.71-6.55 (m, 6H), 5.89 (d, J = 7.9 Hz, 2H) .APCI-MS (m / z): 555 [M ⁺ ])

Example 2 10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -10H-phenoxycyazine (10- (4- Synthesis of (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -10H-phenothiazine)

Example 2- (1): Synthesis of 4- (10H-phenothiazin-10-yl) benzaldehyde (4- (10H-phenothiazin-10-yl) benzaldehyde)

1.5 g (1.0 eq, 7.53 mmol) of 10H-phenoxycazine, 1.57 g (1.13 eq, 8.51 mmol) of 4-bromobenzaldehyde, 0.135 g (0.08 eq, 0.60 mmol) of palladium (II) acetate and 2.60 g of calcium carbonate (2.5 eq, 18.82 mmol) was added to the reaction vessel and vacuum dried, followed by nitrogen gas. 0.35 g (0.1 eq, 0.75 mmol) of 50 wt% tri-talt-butylphosphine and 18 ml of toluene were added to the reaction vessel to dissolve the compounds, and the mixture was stirred under reflux at a temperature of 120 ° C. After completion of the reaction, the mixture was washed with distilled water, and extracted with ethyl acetate. Then, dried over anhydrous magnesium sulfate, filtered through celite, and then 1.48 g (yield = 64.91%) of compound 4- (10H-phenocyazin-10-yl) benzaldehyde through column chromatography. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 9.85 (s, 1H), 7.77-7.72 (m, 2H), 7.41 (dd, J = 7.8, 1.0 Hz, 2H), 7.31-7.24 (m, 4H) , 7.21-7.13 (m, 4H))

Example 2- (2): 10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -10H-phenoxycyazine (10 Synthesis of-(4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -10H-phenothiazine)

1.44 g (1.0 eq, 4.71 mmol), 1,2-di (pyridin-2-yl) ethane of compound 4- (10H-phenoxyazin-10-yl) benzaldehyde obtained in the above Example 2- (1) 1.0 g (1.0 eq, 4.71 mmol) of -1,2-dione, 2.15 ml (5.0 eq, 23.56 mmol) of aniline, and 4.5 g (12.4 eq, 58.43 mmol) of ammonium acetate were placed in a reaction vessel and dried under vacuum. Filled. 30 ml of acetic acid was added to the reaction vessel to dissolve the compounds, and the mixture was stirred under reflux for 12 hours at a temperature of 120 ° C. After completion of the reaction, neutralization was performed using an aqueous sodium hydroxide solution, washed with distilled water, and an organic layer was extracted with chloroform. Dried over anhydrous magnesium sulfate, filtered through celite, and then purified by column chromatography to give the compound 10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl 1.82 g (yield = 67.66%) of (phenyl) -10H-phenoxycyazine were obtained. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 8.48 (dd, J = 23.9, 4.1 Hz, 2H), 7.84 (d, J = 7.9 Hz, 1H), 7.69-7.61 (m, 7H), 7.57 (td , J = 7.7, 1.8 Hz, 1H), 7.39 (d, J = 7.8 Hz, 1H), 7.33-7.19 (m, 13H), 7.12 (dddd, J = 18.1, 7.4, 4.9, 1.1 Hz, 2H), 7.06-7.00 (m, 2H), 6.86 (dtd, J = 24.4, 7.4, 1.4 Hz, 4H), 6.28 (dd, J = 8.1, 1.1 Hz, 2H) .APCI-MS (m / z): 571 [ M ⁺ ])

Example 3: 9,9-dimethyl-10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -9,10-di Hydroacridine (9,9-dimethyl-10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -9,10-dihydroacridine ) Synthesis

Example 3- (1): Synthesis of methyl 2- (phenylamino) benzoate

10 g (1.0 eq, 46.9 mmo) of 2- (phenylamino) benzoic acid was added to a reaction vessel, followed by vacuum drying, and nitrogen gas. 60 ml of methanol was added to the reaction vessel, and the mixture was stirred under reflux for 12 hours at a temperature of 60 ° C. After cooling to room temperature, a saturated sodium bicarbonate solution was put into the reaction vessel to terminate the reaction. After completion of the reaction, the mixture was washed with distilled water, and extracted with ethyl acetate. Then, dried over anhydrous magnesium sulfate, filtered through celite, the solvent was evaporated and 8.5 g (yield = 80.2%) of the compound methyl 2- (phenylamino) benzoate was obtained through column chromatography. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 9.52 (s, 1H), 7.91 (d, J = 8.0 Hz, 1H), 7.26 (t, J = 7.8 Hz, 2H), 7.23-7.19 (m, 3H ), 7.18 (s, 1H), 7.01 (t, J = 7.3 Hz, 1H), 6.70-6.58 (m, 1H), 3.78 (s, 3H))

Example 3- (2): Synthesis of 9,10-dihydro-9.9-dimethylacridine (9,10-dihydro-9,9-dimethylacridine)

8.5 g (1.0 eq, 37.4 mmol) of methyl 2- (phenylamino) benzoate obtained in Example 3- (1) were added to a reaction vessel, followed by vacuum drying, followed by filling with nitrogen gas. 400 ml of tetrahydrofuran (THF) was added to the reaction vessel and 50 ml (4.0 eq, 149.6 mmol) of methylmagnesium bromide at a concentration of 3.0 M were slowly added dropwise and stirred for 3 hours. After completion of the reaction using an aqueous ammonium chloride solution, the mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate and dried. The dried reactant was placed in a reaction vessel, dissolved with methylene chloride, sulfuric acid was added, and stirred at room temperature for 30 minutes. After completion of the reaction, the mixture was neutralized with an aqueous sodium hydroxide solution, washed with distilled water, and the organic layer was extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, filtration through celite, the solvent was evaporated and 4.93 g (yield = 63.0%) of compound 9,10-dihydro-9.9-dimethylacridine was obtained by column chromatography. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 7.38 (d, J = 7.7 Hz, 2H), 7.10 (t, J = 7.2 Hz, 2H), 6.92 (d, J = 6.8 Hz, 2H), 6.69 ( d, J = 7.5 Hz, 2H), 6.13 (s, 1H), 1.58 (s, 3H))

Example 3- (3): 10- (4-bromophenyl) -9,10-dihydro-9,9-dimethylacridine (10- (4-bromophenyl) -9,10-dihydro-9, 9-dimethylacridine)

3.0 g (1.0 eq, 14.33 mmol) of 9,10-dihydro-9.9-dimethylacridine obtained in Example 3- (2), 1-bromo-4-iodobenzene (1-bromo-4- iodobenzene) 5.27 g (1.3 eq, 18.63 mmol), Cu powder 0.472 g (0.52 eq, 7.45 mmol), 18-crown-6 0.3 g (0.08 eq, 1.15 mmol) and potassium carbonate 7.92 g (4.0 eq, 57.34 mmol) To the reaction vessel was dried under vacuum and filled with nitrogen gas. 20 ml of 1,2-dichlorobenzene was added to the reaction vessel to dissolve the compounds, and the mixture was stirred under reflux for 2 hours at a temperature of 190 ° C. After completion of the reaction, the mixture was washed with distilled water, and extracted with ethyl acetate. 3.75 g of compound 10- (4-bromophenyl) -9,10-dihydro-9,9-dimethylacridine, dried over anhydrous magnesium sulfate, filtered through celite and evaporated the solvent. (Yield = 71.8%) was obtained. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 7.78-7.73 (m, 2H), 7.45 (dd, J = 7.6, 1.6 Hz, 2H), 7.24-7.20 (m, 2H), 7.00-6.91 (m, 4H), 6.25 (dd, J = 8.1, 1.4 Hz, 2H), 1.70-1.66 (s, 6H))

Example 3- (4): Synthesis of 4- (9,9-dimethylacridin-10 (9H) -yl) benzaldehyde (4- (9,9-dimethylacridin-10 (9H) -yl) benzaldehyde)

3.75 g (1.0 eq, 5.16 mmol) of 10- (4-bromophenyl) -9,10-dihydro-9,9-dimethylacridine obtained in Example 3- (3) was added to a reaction vessel. After vacuum drying, nitrogen gas was charged. 8 ml of tetrahydrofuran (THF) was added thereto, and the compounds were dissolved by stirring. The concentration of the additive compound was adjusted to -78 ° C using dry ice. 6.2 ml (1.5 eq, 7.74 mmol) of 1.6 M concentration of n-butyl lithium were slowly added dropwise to the reactor while maintaining the temperature at −78 ° C. and stirred for 90 minutes. Subsequently, 1.2 ml (1.5 eq, 7.74 mmol) of dimethylformamide was added to the reaction vessel and stirred for 3 hours. After completion of the reaction, the mixture was washed with distilled water, and extracted with ethyl acetate. Then, dried over anhydrous magnesium sulfate, filtered through celite, and then subjected to column chromatography 2.4 g of compound 4- (9,9-dimethylacridin-10 (9H) -yl) benzaldehyde (yield = 74.2%). Obtained. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 10.12 (s, 1H), 8.17-8.10 (m, 2H), 7.56-7.52 (m, 2H), 7.51-7.47 (m, 2H), 7.02-6.96 ( m, 4H), 6.36-6.30 (m, 2H), 1.69 (s, 6H))

Example 3- (5): 9,9-dimethyl-10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -9 , 10-dihydroacridine (9,9-dimethyl-10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -9 , 10-dihydroacridine)

0.738 g (1.0 eq, 4.71 mmol) of 4- (9,9-dimethylacridin-10 (9H) -yl) benzaldehyde obtained in step 3 (4), 1,2-di (pyridine- 2-yl) ethane-1,2-dione 0.5 g (1.0 eq, 2.36 mmol), aniline 1.08 g (5.0 eq, 11.78 mmol), and 2.25 g (12.4 eq, 29.22 mmol) of ammonium acetate were placed in a reaction vessel and vacuumed. After drying, nitrogen gas was charged. 15 ml of acetic acid was added to the reaction vessel to dissolve the compounds, and the mixture was stirred under reflux for 12 hours at a temperature of 120 ° C. After completion of the reaction, neutralization was performed using an aqueous sodium hydroxide solution, washed with distilled water, and an organic layer was extracted with chloroform. Dried over anhydrous magnesium sulfate, filtered through celite, and then purified by column chromatography to give the compound 9,9-dimethyl-10- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H- 0.61 g (yield = 44.50%) of imidazol-2-yl) phenyl) -9,10-dihydroacridine was obtained. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 8.49 (d, J = 25.3 Hz, 2H), 7.87 (d, J = 8.0 Hz, 1H), 7.74-7.69 (m, 2H), 7.65 (t, J = 6.9 Hz, 1H), 7.62-7.55 (m, 1H), 7.45-7.37 (m, 3H), 7.33-7.28 (m, 3H), 7.25-7.19 (m, 4H), 7.16-7.09 (m, 2H ), 6.94 (dtd, J = 23.4, 7.3, 1.5 Hz, 4H), 6.24 (dd, J = 8.1, 1.3 Hz, 2H), 1.66 (s, 6H), APCI-MS (m / z): 581 [ M ⁺ ])

Example 4: 9- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -9H-carbazole (9- (4- ( Synthesis of 1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -9H-carbazole)

Example 4- (1): Synthesis of 4- (9H-carbazol-9-yl) benzaldehyde (4- (9H-carbazol-9-yl) benzaldehyde)

9H-carbazole 1.5 g (1.0 eq, 7.53 mmol), 4-bromobenzaldehyde 1.57 g (1.13 eq, 8.51 mmol), bis (dibenzylideneacetone) palladium (0) 0.135 g (0.08 eq, 0.60 mmol) And 2.60 g (2.5 eq, 18.82 mmol) of calcium carbonate were placed in a reaction vessel and dried in vacuo to fill with nitrogen gas. 0.35 g (0.1 eq, 0.75 mmol) of 50 wt% tri-talt-butylphosphine and 18 ml of toluene were added to the reaction vessel to dissolve the compounds, and the mixture was stirred under reflux at a temperature of 120 ° C. After completion of the reaction, the mixture was washed with distilled water, and extracted with ethyl acetate. Then, dried over anhydrous magnesium sulfate, filtered through celite, and then column chromatography gave 1.48 g (yield = 64.91%) of compound 4- (9H-carbazol-9-yl) benzaldehyde. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 10.12 (s, 1H), 8.18-8.11 (m, 4H), 7.80 (d, J = 8.3 Hz, 2H), 7.51 (d, J = 8.2 Hz, 2H ), 7.47-7.41 (m, 2H), 7.36-7.31 (m, 2H))

Example 4- (2): 9- (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -9H-carbazole (9- Synthesis of (4- (1-phenyl-4,5-di (pyridin-2-yl) -1H-imidazol-2-yl) phenyl) -9H-carbazole)

0.86 g (1.0 eq, 3.16 mmol), 1,2-di (pyridin-2-yl) ethane of compound 4- (9H-carbazol-9-yl) benzaldehyde obtained in the above Example 4- (1) 0.67 g (1.0 eq, 3.16 mmol) of -1,2-dione, 1.44 ml (5.0 eq, 15.84 mmol) of aniline, and 3.03 g (12.4 eq, 39.30 mmol) of ammonium acetate were placed in a reaction vessel and dried under vacuum. Filled. 20 ml of acetic acid was added to the reaction vessel to dissolve the compounds, and the mixture was stirred under reflux for 12 hours at a temperature of 120 ° C. After completion of the reaction, neutralization was performed using an aqueous sodium hydroxide solution, washed with distilled water, and an organic layer was extracted with chloroform. After drying over anhydrous magnesium sulfate and filtration through celite, compound 9- (4- (1-phenyl-4,5-di (pyridine) was purified by column chromatography and recrystallization with ethyl acetate, n-hexane, and ethanol. 0.78 g (yield = 45.88%) of 2-yl) -1H-imidazol-2-yl) phenyl) -9H-carbazole were obtained. ( ¹ H NMR (500 MHz, CDCl ₃ ) δ 8.49 (dd, J = 24.1, 4.1 Hz, 2H), 8.12 (d, J = 7.7 Hz, 2H), 7.87 (d, J = 7.9 Hz, 1H), 7.70 (d, J = 8.5 Hz, 2H), 7.64 (td, J = 7.8, 1.8 Hz, 1H), 7.58 (td, J = 7.7, 1.8 Hz, 1H), 7.47 (d, J = 8.5 Hz, 2H ), 7.40 (dd, J = 10.3, 5.8 Hz, 5H), 7.36-7.31 (m, 3H), 7.28-7.24 (m, 4H), 7.13 (dddd, J = 17.5, 7.4, 4.9, 1.0 Hz, 2H APCI-MS (m / z): 539 [M ⁺ ])

Experimental Example 1 Measurement of Organic Electroluminescence Characteristics

A glass substrate coated with an indium tin oxide (ITO) thin film was used for OLED manufacturing, and the sheet resistance of the glass substrate was 10 Ω / square and the thickness was 150 nm. The ITO-coated glass was ultrasonically washed in an ultrasonic bath in the order of acetone, methyl alcohol, and distilled water, then left in isopropyl alcohol for 20 minutes and dried using an N ₂ gas gun. The substrate was treated with O ₂ plasma in an Ar atmosphere. Mount the ITO-coated glass on the substrate folder of the vacuum deposition equipment and 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB) to the cell in the vacuum deposition equipment. Put it. After evacuating until the vacuum in the chamber reached 5.0 × 10 ⁻⁷ Torr, a current was applied to the cell to evaporate the organic layer to deposit a 50 nm thick hole injection layer on the ITO substrate. Then, 4,4 ', 4''-tris (carbazo-9-yl) -triphenylamine (TCTA) was evaporated under the same conditions to deposit a 10 nm thick hole transport layer. In addition, the organic light emitting compound (1-4) synthesized as in Example 1 was evaporated in the vacuum deposition equipment at a rate of 1.0 mW / sec to deposit a light emitting layer having a thickness of 20 nm on the hole transport layer. Later, under similar conditions, 2,2 ', 2''-(1,3,5-benzintril) -tris (1-phenyl-1-H-benzimidazole) (TPBi) and lithium quinolate (Liq) Evaporation was performed sequentially to deposit an electron transport layer and an electron injection layer having a thickness of 30 nm and 2 nm, respectively. All organic materials and metals were deposited under high vacuum (5.0 × 10 ⁻⁷ Torr). Then, an Al cathode was deposited to a thickness of 100 nm using another vacuum deposition equipment to manufacture an OLED.

OLEDs according to this Experimental Example were prepared in the following order: ITO (150 nm) / 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPB, HIL) (50 nm) / 4,4 ′, 4 ″ -tris (carbazo-9-yl) -triphenylamine (TCTA, HTL) 10 nm / blue fluorescent material 1-4 (20 nm, EML) / 2,2 ′ , 2 "-(1,3,5-benzintril) -tris (1-phenyl-1-H-benzimidazole) (TPBi, ETL) (30 nm) / lithium quinolate (Liq) (2 nm) / Al (100 nm).

The luminescence properties and electroluminescence (EL) spectra of the OLED were measured using a Keithley 2400 source measurement unit and a CS1000A spectrophotometer and the results are shown in Table 1.

The above description of the present application is intended for illustration, and it will be understood by those skilled in the art that the present invention may be easily modified in other specific forms without changing the technical spirit or essential features of the present application. Therefore, it should be understood that the embodiments described above are exemplary 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 following claims rather than the above description, and it should be construed that all changes or modifications derived from the meaning and scope of the claims and their equivalents are included in the scope of the present application.

Claims (13)

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

(In Formula 1,
R ₁ is substituted or linear or branched C ₁ -C ₂₀ alkyl, substituted C ₆ -C ₂₀ aryl,
R ₂ 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 hetero ring which may be substituted and a 6-membered unsaturated or aromatic which may be substituted At least one ring selected from the group consisting of hetero rings, or at least two rings selected from the group are fused polycyclic rings,
A ₁ and A ₂ are each independently at least one ring selected from the group consisting of a 5-membered unsaturated or aromatic hetero ring which may be substituted and a 6-membered unsaturated or aromatic hetero ring which may be substituted,
The hetero ring includes one or more selected from the group consisting of N, O and S,
Said substitution is by C ₁ -C ₆ alkyl or C ₆ -C ₂₀ aryl).
The method of claim 1,
R ₁ is selected from the group consisting of a single bond, methyl, substituted phenyl, biphenyl, chrysene, phenanthrene, naphthyl, fluorenyl, quinoline, perylene, pyrene and combinations thereof To do that,
Wherein said substitution is substituted by linear or branched C ₁ -C ₂₀ alkyl.
The method of claim 1,
R ₂ is phenoxazine, phenoxyazine, dimethylacridine, diphenylacridine, carbazole, phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, pyrene, fluoranthene, Organic, including a material selected from the group consisting of sen, benzofluoranthene, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiophene, dibenzofuran and combinations thereof Luminescent compounds.
The method of claim 1,
Wherein A ₁ and A ₂ are each independently pyridine, pyrimidine, pyrrole, carbazole, quinoline, and a combination thereof, and an organic light emitting compound.
The method of claim 1,
The organic light emitting compound is any one of the following compounds, an organic light emitting compound:

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A method for preparing an organic light emitting compound according to claim 1, comprising reacting a compound represented by the following Chemical Formula 2, a compound represented by the following Chemical Formula 3, and a compound including pyridine in the presence of an ammonium salt:
[Formula 2]

[Formula 3]

(In Chemical Formulas 2 and 3,
R ₁ is substituted or linear or branched C ₁ -C ₂₀ alkyl, substituted C ₆ -C ₂₀ aryl,
R ₂ 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 hetero ring which may be substituted and a 6-membered unsaturated or aromatic which may be substituted At least one ring selected from the group consisting of hetero rings, or at least two rings selected from the group are fused polycyclic rings,
The hetero ring includes one or more selected from the group consisting of N, O and S,
Said substitution is by C ₁ -C ₆ alkyl or C ₆ -C ₂₀ aryl).
The method of claim 6,
R ₁ is selected from the group consisting of a single bond, methyl, substituted phenyl, biphenyl, chrysene, phenanthrene, naphthyl, fluorenyl, quinoline, perylene, pyrene and combinations thereof To do that,
Wherein said substitution is substituted by linear or branched C ₁ -C ₂₀ alkyl.
The method of claim 6,
R ₂ is phenoxazine, phenoxyazine, dimethylacridine, diphenylacridine, carbazole, phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, pyrene, fluoranthene, Organic, including a material selected from the group consisting of sen, benzofluoranthene, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiophene, dibenzofuran and combinations thereof Method for producing a luminescent compound.
The method of claim 6,
The compound containing pyridine includes 1,2-di (pyridin-2-yl) ethane-1,2-dione (1,2-di (pyridine-2-yl) ethane-1,2-dione) It is a manufacturing method of an organic light emitting compound.
The method of claim 6,
The ammonium salt includes ammonium salt selected from the group consisting of ammonium acetate, ammonium fluoride, ammonium chloride, ammonium bromide, ammonium iodide, ammonium cyanide, ammonium nitrate, ammonium sulfate, ammonium carbonate and combinations thereof , Manufacturing method of organic light emitting compound.
The method of claim 6,
The reaction is carried out under a solvent, a method for producing an organic light emitting compound.
The method of claim 11,
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, A method for producing an organic light emitting compound, comprising a solvent consisting of tetrahydrofuran, dichloromethane, acetonitrile and combinations thereof.
An organic electroluminescent device comprising the organic light emitting compound according to any one of claims 1 to 5.

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