KR102498512B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention is an organic light emitting compound represented by the following [Chemical Formula I], and when this is employed in an electron blocking layer, a hole transport layer or a light emitting layer, etc., it is possible to implement an organic light emitting device having very excellent light emitting properties such as luminous efficiency and quantum efficiency. .
[Formula I]

Description

An organic light emitting compound and an organic electroluminescent device comprising the same {An electroluminescent compound and an electroluminescent device comprising the same}

The present invention relates to an organic light emitting compound, and more particularly, to an organic light emitting compound employed in an organic material layer in an organic light emitting device and an organic light emitting device having significantly improved light emitting properties such as long lifespan and luminous efficiency by employing the same.

Organic light emitting devices can not only be formed on a transparent substrate, but also can be driven at a low voltage of 10 V or less compared to plasma display panels or inorganic electroluminescent (EL) displays, and consume relatively little power. It has the advantage of being excellent in color and can show three colors of green, blue, and red, so it has recently become a subject of much interest as a next-generation display device.

However, in order for such an organic electroluminescent device to exhibit the above characteristics, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc., which are materials constituting the organic layer in the device, are supported by stable and efficient materials. However, the development of stable and efficient organic material layer materials for organic light emitting devices has not yet been sufficiently achieved. Therefore, there is a continuing demand for the development of new materials capable of improving light emitting properties and the development of organic layer structures in devices.

Therefore, the present invention is a novel organic light emitting compound that can be employed as a host compound of an electron blocking layer, a hole transport layer or a light emitting layer in an organic light emitting device to significantly improve light emitting properties such as long lifespan and luminous efficiency, and an organic light emitting compound including the same. We want to provide a small element.

In order to solve the above problems, the present invention provides an organic light emitting compound represented by the following [Chemical Formula I] and an organic light emitting device including the same.

[Formula I]

The detailed structure and substituents of [Chemical Formula I] will be described later.

An organic electroluminescent device employing the organic light emitting compound according to the present invention in an electron blocking layer, a hole transport layer, or a light emitting layer has remarkably excellent light emitting characteristics such as long lifespan and luminous efficiency compared to conventional devices, and can be usefully used in various display devices.

1 is a representative diagram showing the structure of an organic light emitting compound according to the present invention.

Hereinafter, the present invention will be described in more detail.

The present invention relates to an organic light emitting compound represented by the following [Chemical Formula 1], and when employed in an organic layer such as a hole transport layer, an electron blocking layer, and a light emitting layer in an organic light emitting device, organic light emitting properties such as long lifespan and light emitting efficiency are remarkably improved. It is possible to implement a light emitting device.

[Formula I]

In the above [Formula I],

Y ₁ and Y ₂ are each independently O or S, and R ₁ and R ₂ are each independently hydrogen, a substituted or unsubstituted carbon number substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms in which one or more substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms are fused. It is selected from one or more fused substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms.

A may be any one selected from the following [Structural Formula 1] to [Structural Formula 3].

[Structural Formula 1]

[Structural Formula 2]

[Structural Formula 3]

In [Structural Formula 1] to [Structural Formula 3],

X ₁ to X ₃ are the same as or different from each other, and each independently represents CH or N.

L is a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 30 carbon atoms, substituted or unsubstituted Cycloalkylene group having 3 to 30 carbon atoms, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms selected from a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which one or more fused or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused do.

Ar ₁ to Ar ₃ are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms It is selected from substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms in which one or more ringed cycloalkyls having 3 to 30 carbon atoms are fused.

The Ar ₁ to Ar ₃ may be bonded to each other or linked to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring are N, S And it may be substituted with one or more heteroatoms selected from O.

The compound according to the present invention is characterized by having a characteristic substituent A while Y ₁ and Y ₂ are each independently O or S, and an organic light emitting device employing the compound according to the present invention in an organic layer due to these structural characteristics It has excellent luminous properties such as long lifespan and luminous efficiency.

Meanwhile, in the definition of R ₁ , R ₂ , L and Ar ₁ to Ar ₃ , substituted or unsubstituted means that R ₁ , R ₂ , L and Ar ₁ to Ar ₃ are deuterium, a cyano group, a halogen group, a hydroxy group, Nitro group, C1-24 alkyl group, C1-24 halogenated alkyl group, C1-24 alkenyl group, C1-24 alkynyl group, C1-24 heteroalkyl group, C6-24 aryl group , C6-24 arylalkyl group, C2-24 heteroaryl group, or C2-24 heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C1-24 aryl It is selected from the group consisting of an amino group, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms, and is selected from one or two or more substituents It means that it is substituted, that it is substituted with a substituent in which two or more substituents among the above substituents are connected, or that it does not have any substituent.

For example, a substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, and the like are substituted with other substituents. do.

The substituted heteroaryl group refers to a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group, and condensed heterocyclic groups thereof, such as a benzquinoline group, a benzene group, It means that an imidazole group, a benzoxazole group, a benzothiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with other substituents.

In the present invention, examples of the substituents will be described in detail below, but are not limited thereto.

In the present invention, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but is not limited thereto.

Specific examples of the aryloxy group used in the present invention include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyloxy, indenyloxy, and the like, and one or more hydrogen atoms included in the aryloxy group can be further substituted.

Specific examples of the silyl group used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl etc. can be mentioned.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and the like, and examples of a polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, and tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited only to these examples.

In addition, the aryl group may also be further substituted with one or more substituents, and more specifically, at least one hydrogen atom of the aryl group is a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (—NH ₂ , -NH(R), -N(R')(R"), R' and R" are each independently an alkyl group having 1 to 10 carbon atoms, in which case it is referred to as "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-24 alkyl group, C1-24 halogenated alkyl group, C1-24 alkenyl group, C1-24 alkynyl group, C1-24 hetero group It may be substituted with an alkyl group, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, and the like.

In the present invention, the alkenyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 20. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1 -butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited thereto.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms. Examples thereof include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, and an acridyl group. , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group , carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, iso Examples include an oxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, and a phenothiazinyl group, but are not limited thereto.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, and a cyclohexyl group. Pyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo octyl group and the like, but are not limited thereto.

In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In addition, various specific examples of the substituent according to the present invention can be clearly identified in the specific compounds described below.

As described above, the organic light-emitting compound according to the present invention represented by [Chemical Formula I] can be used as an organic material layer of an organic light-emitting device due to its structural specificity, and more specifically, depending on the characteristics of various substituents introduced, the organic light-emitting compound of the organic material layer It can be used as a host compound for a blocking layer, a hole transport layer or a light emitting layer.

Preferable specific examples of the compound represented by [Chemical Formula I] according to the present invention include the following [Compound 1] to [Compound 208], but the scope of the present invention is not limited only to these.

By introducing various substituents into the core structure of the above structure, an organic light emitting compound having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, the electron transport layer material and the electron blocking layer material used in the manufacture of the organic light emitting device into the structure, the conditions required by each organic layer are met. A material can be produced, in particular, when the compound of [Formula I] according to the present invention is used as a host material for an electron blocking layer, a hole transport layer or a light emitting layer, in particular, when the electron blocking layer is employed, long life of the device, luminous efficiency, etc. characteristics can be further improved.

The organic light emitting compound according to the present invention can be applied to an organic light emitting device according to a conventional manufacturing method.

An organic electroluminescent device according to one embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic material layer disposed therebetween, and the organic light emitting compound according to the present invention is used in the organic material layer of the device. Except that it can be manufactured using conventional device manufacturing methods and materials.

The organic material layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and the like. However, it is not limited thereto and may include fewer or more organic material layers.

Therefore, in the organic electroluminescent device according to the present invention, the organic material layer may include at least one layer of a hole transport layer, an electron blocking layer, and a light emitting layer, and at least one layer among the layers is an organic light emitting layer represented by the [Chemical Formula I] compounds may be included.

In addition, the organic light emitting device according to the present invention uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer is formed by using various polymer materials and using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. Can be made in layers.

As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , but conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

As the cathode material, it is preferable to use a material having a small work function so as to easily inject electrons into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayers such as LiF/Al or LiO ₂ /Al. structural materials, etc., but are not limited thereto.

The hole injection material is a material capable of receiving holes well from the anode at a low voltage, and the hole injection material preferably has a highest occupied molecular orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

The light-emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazoles, benzthiazoles, and Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited thereto.

As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include an Al complex of 8-hydroxyquinoline, a complex including Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

In addition, the organic light emitting compound according to the present invention may act in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like, on a principle similar to that applied to organic light emitting devices.

Hereinafter, synthesis examples and device examples of preferred compounds are presented to aid understanding of the present invention. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereby.

synthesis example 1: compound 6 synthesis

(One) manufacturing example 1: synthesis of intermediate 6-1

After adding 4-bromo-1,2-dimethoxybenzene (10 g, 0.046 mol, sigma aldrich) and 200 mL of dichloromethane, boron tribromide (25.39 g, 0.101 mol, sigma aldrich) was added dropwise at 0 ° C, followed by stirring at room temperature for 12 hours. made it After completion of the reaction, H ₂ O (NaHCO ₃ ) was added, the layers were separated, and column purification (N-HEXANE: MC) was performed to obtain 7.5 g of <Intermediate 6-1> (yield: 86%).

(2) manufacturing example 2: synthesis of intermediate 6-2

Intermediate 6-1 (10 g, 0.053 mol, sigma Aldrich), Iodobenzene (24.83 g, 0.122 mol, sigma Aldrich), potassium carbonate (29.25 g, 0.212 mol, sigma Aldrich), Iron(II) acetylacetonate (3.74 g, 0.212 mol, sigma aldrich), copper iodide (2.02 g, 0.011 mol, sigma aldrich), and 200 mL of DMSO were stirred and reacted at 140 °C for 65 hours. After completion of the reaction, ether and H ₂ 0 were added, and layers were separated and extracted by adding EA and sodium sulfate anhydrous, followed by column purification to obtain 14.6 g of <Intermediate 6-2> (yield: 81%).

(3) manufacturing example 3: synthesis of intermediate 6-3

Intermediate 6-2 (10 g, 0.029 mol), potassium carbonate (0.81 g, 0.006 mol, sigma aldrich), Palladium (II) acetate (0.66 g, 0.003 mol, sigma aldrich) 150 mL of pivalic acid was added and stirred at 120 ° C for 45 hours. The reaction was stirred while refluxing. After completion of the reaction, layer separation was performed using H ₂ O:MC, followed by column purification (N-HEXANE:EA) to obtain 7.2 g of <Intermediate 6-3> (yield: 73%).

(4) manufacturing example 4: synthesis of intermediate 6-4

Intermediate 6-3 (10 g, 0.030 mol), Bis(pinacolato)dibron (9.79 g, 0.039 mol, sigma aldrich), potassium acetate (5.82 g, 0.06 mol, sigma aldrich), PdCl ₂ (dppf) (0.65 g, 0.0009 mol, sigma aldrich) and 200 mL of 1,4-Dioxane were added, followed by stirring at 95 °C for 12 hours. After completion of the reaction, H ₂ 0 was added, layer separation was performed, and column purification (N-HEXANE: MC) was performed to obtain 9 g of <Intermediate 6-4> (yield: 79%).

(5) manufacturing example 5: synthesis of intermediate 6-5

1-bromo-4-iodobenzene (10 g, 0.035 mol, sigma aldrich), intermediate 6-4 (16.3 g, 0.042 mol, sigma aldrich), potassium carbonate (9.77 g, 0.071 mol, sigma aldrich), Pd (PPh ₃ ) ₄ (2.04 g, 0.0018 mol, sigma aldrich), 200 mL of THF, and 40 mL of H ₂ O were added and stirred under reflux for 12 hours to react. After completion of the reaction, layer separation was performed using H ₂ O:MC, followed by column purification (N-HEXANE:MC) to obtain 12 g of <Intermediate 6-5> (yield: 82%).

(6) manufacturing example 6: synthesis of intermediate 6-6

4-bromobiphenyl (10 g, 0.043 mol, sigma aldrich), 4-aminobiphenyl (8.71 g, 0.052 mol, sigma aldrich), sodium tert-butoxide (8.25 g, 0.086 mol, sigma aldrich), catalyst Pd (dba) ₂ ( 1.23 g, 0.0021 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.87 g, 0.0043 mol, sigma aldrich) were added with 150 mL of toluene, followed by stirring at 100 °C for 1 hour. After completion of the reaction, H ₂ 0 : MC was layered and purified by column (N-HEXANE: EA) to obtain 11.1 g of <Intermediate 6-6> (yield: 80.5%).

(7) manufacturing example 7: synthesis of compound 6

Intermediate 6-5 (10 g, 0.025 mol), Intermediate 6-6 (11.95 g, 0.030 mol), Sodium tert-butoxide (4.81 g, 0.050 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.72 g, 0.0013 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.51 g, 0.0025 mol, sigma aldrich) were added with 150 mL of toluene, followed by stirring at 100 °C for 4 hours. After completion of the reaction, H ₂ 0 : MC was layer-separated, and column purification (N-HEXANE: EA) was performed to obtain 11.7 g of Compound 7 (yield: 72.5%).

H-NMR (200 MHz, CDCl3): δ ppm, 1H (7.91/d, 7.89/d, 7.81/d, 7.66/d, 7.38/m, 7.32/m) 2H (7.85/d, 7.79/d, 7.47/ m) 3H (7.41/m) 4H (7.52/d) 6H (7.54/d, 7.51/m, 6.69/d)

LC/MS: m/z=715 [(M+1) ⁺ ]

synthesis example 2: compound 13 synthesis

(One) manufacturing example 1: synthesis of intermediate 13-1

2-bromo-9,9-dimethyl-9H-fluorene (10 g, 0.037 mol, sigma aldrich), 4-aminobiphenyl (7.43 g, 0.044 mol, sigma aldrich), sodium tert-butoxide (7.04 g, 0.073 mol, sigma aldrich), catalyst Pd (dba) ₂ (1.05 g, 0.0018 mol, sigma aldrich), and tri-tert-Bu-phosphine (0.74 g, 0.0037 mol, sigma aldrich) were added with 150 mL of toluene and stirred at 100 ° C for 5 hours. and reacted. After completion of the reaction, layer separation was performed on _H2 :MC, followed by column purification (N-HEXANE:MC) to obtain 10.3 g of <Intermediate 13-1> (yield: 77.8%).

(2) manufacturing example 2: synthesis of compound 13

Intermediate 6-5 (10 g, 0.024 mol), Intermediate 13-1 (10.50 g, 0.029 mol), Sodium tert-butoxide (4.65 g, 0.048 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.70 g, 0.0012 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.49 g, 0.0024 mol, sigma aldrich) were added with 150 mL of toluene, followed by stirring at 100°C for 4 hours to react. After completion of the reaction, layer separation was performed on H ₂ O:MC, followed by column purification (N-HEXANE: EA) to obtain 12.9 g of Compound 13 (yield: 76.8%).

H-NMR (200 MHz, CDCl3): δ ppm, 1H (7.87/d, 7.62/d, 7.55/d, 7.41/m, 7.35/s, 7.28/m, 6.75/s, 6.58/d) 2H (7.89/d) d, 7.66/d, 7.52/d, 7.51/m, 7.32/m) 3H (7.38/m) 4H (7.54/d, 6.69/d) 6H (1.72/s)

LC/MS: m/z=693 [(M+1) ⁺ ]

synthesis example 3: Synthesis of compound 40

(One) manufacturing example 1: synthesis of intermediate 40-1

4-iodoaniline (10 g, 0.046 mol, sigma aldrich), 3-bromophenylboronic acid (10.09 g, 0.050 mol, sigma aldrich), potassium carbonate (15.78 g, 0.114 mol, sigma aldrich), Pd(PPh ₃ ) ₄ (2.64 g, 0.0023 mol, sigma aldrich), 200 mL of THF, and 40 mL of H ₂ O were added and stirred under reflux for 6 hours to react. After completion of the reaction, layer separation was performed using H ₂ O:MC, followed by column purification (N-HEXANE: EA) to obtain 9 g of <Intermediate 40-1> (yield: 79.4%).

(2) manufacturing example 2: synthesis of intermediate 40-2

Intermediate 40-1 (10 g, 0.040 mol), phenylboronic acid (5.90 g, 0.048 mol, sigma aldrich), potassium carbonate (13.93 g, 0.101 mol, sigma aldrich), Pd(PPh ₃ ) ₄ (2.33 g, 0.0020 mol , sigma aldrich), 200 mL of THF, and 40 mL of H ₂ O were added and reacted by stirring under reflux for 6 hours. After completion of the reaction, layer separation was performed using H ₂ O:MC, followed by column purification (N-HEXANE: EA) to obtain 9.8 g of <Intermediate 40-2> (yield: 79.3%).

(3) manufacturing example 3: synthesis of intermediate 40-3

3-bromo-9-phenyl-9H-carbazole (10 g, 0.031 mol, TCI), intermediate 16-1 (8.38 g, 0.034 mol), sodium tert-butoxide (5.97 g, 0.062 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.89 g, 0.0016 mol, sigma aldrich), tri-tert-Bu-phosphine (0.63 g, 0.0031 mol, sigma aldrich) was added with 150 mL of Toluene, 30 mL of EtOH, and 15 mL of H ₂ O and heated to 100 °C. was reacted by stirring for 2 hours. After completion of the reaction, H ₂ 0 : MC was layer-separated, and column purification (N-HEXANE: EA) was performed to obtain 12 g of <Intermediate 40-3> (yield: 79.5%).

(4) manufacturing example 4: synthesis of compound 40

Intermediate 6-5 (10 g, 0.024 mol), Intermediate 40-3 (12.95 g, 0.027 mol), Sodium tert-butoxide (4.65 g, 0.048 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.70 g, 0.0012 mol, sigma aldrich), and tri-tert-Bu-phosphine (0.49 g, 0.0024 mol, sigma aldrich) were mixed with 150 mL of Toluene, 30 mL of EtOH, and 15 mL of H ₂ O, and stirred at 100 °C for 8 hours to react. After completion, layer separation was performed on H ₂ 0:MC, followed by column purification (N-HEXANE: EA) to obtain 15.7 g of Compound 40 (yield: 79.2%).

H-NMR (200 MHz, CDCl3): δ ppm, 1H (8.12/d, 7.70/s, 7.69/d, 7.57/m, 7.45/m, 7.41/m, 7.35/s, 7.29/m, 5.93/d) 2H(7.89/d, 7.66/d, 7.63/d, 7.58/m, 7.52/d, 7.51/m, 7.48/d, 7.38/m, 7.32/m) 3H(7.50/m) 4H(7.54/d, 6.69/d)

LC/MS: m/z=818 [(M+1) ⁺ ]

synthesis example 4: compound 85 synthesis

(One) manufacturing example 1: synthesis of intermediate 85-1

4-bromodibenzofuran (10 g, 0.041 mol, sigma aldrich), 9,9-dimethyl-9H-fluoren-2-amine (9.32 g, 0.045 mol, TCI), sodium tert-butoxide (7.78 g, 0.081 mol, sigma aldrich ), catalyst Pd(dba) ₂ (1.16 g, 0.002 mol, sigma aldrich), tri-tert-Bu-phosphine (0.82 g, 0.004 mol, sigma aldrich) in 150 mL of Toluene, 30 mL of EtOH, 15 mL of H ₂ O was added and reacted by stirring at 100 °C for 3 hours. After completion of the reaction, H ₂ 0 : MC was layer-separated and then purified by column (N-HEXANE: EA) to obtain 12.2 g of <Intermediate 85-1> (yield: 80.3%).

(2) manufacturing example 2: synthesis of compound 85

Intermediate 6-5 (10 g, 0.024 mol), Intermediate 85-1 (9.99 g, 0.027 mol), Sodium tert-butoxide (4.65 g, 0.048 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.70 g, 0.0012 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.49 g, 0.0024 mol, sigma aldrich) were mixed with 150 mL of Toluene, 30 mL of EtOH, and 15 mL of H ₂ O, and reacted by stirring at 100 °C for 8 hours. After completion of the reaction, H ₂ O:MC was layer-separated and then purified by column (N-HEXANE: EA) to obtain 13.6 g of Compound 85 (yield: 79.4%).

H-NMR (200 MHz, CDCl3): δ ppm, 1H (7.87/d, 7.62/s, 7.55/d, 7.35/s, 7.28/m, 7.25/d, 7.07/m, 6.75/s, 6.58/d, 6.39/d) 2H (7.54/d, 6.69/d) 3H (7.89/d, 7.66/d, 7.32/m) 4H (7.38/m) 6H (1.72/s)

LC/MS: m/z=707 [(M+1) ⁺ ]

synthesis example 5: compound 112 synthesis

(One) manufacturing example 1: synthesis of intermediate 112-1

4-bromobiphenyl (10 g, 0.043 mol, sigma aldrich), 4-amino-p-terphenyl (11.58 g, 0.047 mol, sigma aldrich), sodium tert-butoxide (8.25 g, 0.089 mol, sigma aldrich), catalyst Pd ( 150 mL of Toluene was added to dba) ₂ (1.23 g, 0.0021 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.87 g, 0.0043 mol, sigma aldrich), followed by stirring at 100°C for 6 hours. After completion of the reaction, H ₂ 0 : MC was layered and purified by column (N-HEXANE: MC) to obtain 13.4 g of <Intermediate 112-1> (yield: 78.6%).

(2) manufacturing example 2: synthesis of intermediate 112-2

1-bromo-3-iodobenzene (10 g, 0.035 mol, sigma aldrich), intermediate 6-4 (16.3 g, 0.042 mol, sigma aldrich), potassium carbonate (9.77 g, 0.071 mol, sigma aldrich), Pd (PPh ₃ ) ₄ (2.04 g, 0.0018 mol, sigma aldrich), 200 mL of THF, and 40 mL of H ₂ O were added and stirred under reflux for 12 hours to react. After completion of the reaction, layer separation was performed using H ₂ O:MC, followed by column purification (N-HEXANE:MC) to obtain 12 g of <Intermediate 112-2> (yield: 82%).

(3) manufacturing example 3: Synthesis of Compound 112

Intermediate 112-2 (10 g, 0.024 mol), Intermediate 112-1 (10.58 g, 0.027 mol), Sodium tert-butoxide (4.65 g, 0.048 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.70 g, 0.0012 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.49 g, 0.0024 mol, sigma aldrich) were added with 150 mL of toluene, and reacted by stirring at 100 °C for 1 hour. After completion of the reaction, H ₂ O:MC was layer-separated, and column purification (N-HEXANE: EA) was performed to obtain 14 g of Compound 112 (yield: 79.3%).

H-NMR (200 MHz, CDCl3): δ ppm, 1H (7.44/m, 7.35/s, 6.89/s, 6.88/d, 6.59/d) 2H (7.89/d, 7.66/d, 7.41/m, 7.38/ m, 7.32/m) 4H (7.54/d, 7.52/d, 7.51/m, 7.25/d, 6.69/d)

LC/MS: m/z=729 [(M+1) ⁺ ]

synthesis example 6: compound 168 synthesis

(One) manufacturing example 1: synthesis of intermediate 168-1

3-bromodibenzo[b,d]furan (10 g, 0.041 mol, Yurui), 2-(methylthio)phenylboronic acid (8.16 g, 0.049 mol, sigma aldrich), potassium carbonate (16.78 g, 0.121 mol, sigma aldrich), Pd(PPh ₃ ) ₄ (2.34 g, 0.0020 mol, sigma aldrich), 200 mL of THF, and 40 mL of H ₂ O were added and reacted by stirring under reflux for 4 hours. After completion of the reaction, layer separation was performed using H ₂ O : EA, followed by column purification (N-HEXANE : EA) to obtain 10 g of <Intermediate 168-1> (yield: 85%).

(2) manufacturing example 2: synthesis of intermediate 168-2

10 mL of hydrogen peroxide (35%) was slowly added dropwise to Intermediate 168-1 (10 g, 0.031 mol), 150 mL of THF, and 150 mL of acetic acid, followed by stirring at room temperature for 12 hours to react. After completion of the reaction, the solvent was removed by concentrating, and the organic layer was extracted using MC: H ₂ O, and then concentrated after removing moisture to proceed with the next reaction.

(3) manufacturing example 3: synthesis of intermediate 168-3

Intermediate 168-2, 120 mL of Pyridine, and 250 mL of H ₂ O were added thereto, followed by stirring under reflux for 4 hours at 120 °C. After completion of the reaction, layer separation was performed using H ₂ O:MC, followed by column purification (N-HEXANE:MC) to obtain 8.3 g of <Intermediate 168-3> (yield: 87.8%).

(4) manufacturing example 4: synthesis of intermediate 168-4

Intermediate 168-3 (10 g, 0.034 mol) and 200 mL of chloroform were added, cooled to 0 ° C, and bromine (6.05 g, 0.038 mol, sigma aldrich) was slowly added dropwise, followed by stirring and reacting at room temperature for 12 hours. After the reaction was completed, bromine was removed using 2M NaOH aqueous solution, and the resulting solid was filtered to obtain 10.6 g of <Intermediate 168-4> (yield: 82.3%).

(5) manufacturing example 5: synthesis of intermediate 168-5

Intermediate 168-4 (10 g, 0.028 mol), Bis(pinacolato)dibron (9.35 g, 0.037 mol, sigma aldrich), potassium acetate (5.56 g, 0.057 mol, sigma aldrich), PdCl ₂ (dppf) (0.62 g, 0.0008 mol, sigma aldrich) and 200 mL of 1,4-Dioxane were added, followed by stirring at 95 °C for 12 hours. After completion of the reaction, H ₂ 0 was added, layer separation was performed, and column purification (N-HEXANE: MC) was performed to obtain 8.8 g of <Intermediate 168-5> (yield: 77.7%).

(6) manufacturing example 6: synthesis of intermediate 168-6

1-bromo-4-iodobenzene (10 g, 0.035 mol, sigma aldrich), intermediate 168-5 (15.56 g, 0.039 mol, sigma aldrich), potassium carbonate (12.21 g, 0.088 mol, sigma aldrich), Pd (PPh ₃ ) ₄ (2.04 g, 0.0018 mol, sigma aldrich), 200 mL of THF, and 40 mL of H ₂ O were added and stirred under reflux for 12 hours to react. After completion of the reaction, layer separation was performed using H ₂ 0:MC, followed by column purification (N-HEXANE:MC) to obtain 12.6 g of <Intermediate 168-6> (yield: 83%).

(7) manufacturing example 7: synthesis of intermediate 168-7

4-bromodibenzofuran (10 g, 0.041 mol, sigma aldrich), 4-aminophenylboronic acid pinacol ester (10.64 g, 0.047 mol, sigma aldrich), potassium carbonate (13.98 g, 0.101 mol, sigma aldrich), Pd (PPh ₃ ) ₄ (2.34 g, 0.002 mol, sigma aldrich), 150 mL of THF, and 40 mL of H ₂ O were added and stirred under reflux for 4 hours to react. After completion of the reaction, layer separation was performed using H ₂ O:MC, followed by column purification (N-HEXANE:MC) to obtain 8.1 g of <Intermediate 168-7> (yield: 77.19%).

(8) manufacturing example 8: synthesis of intermediate 168-8

4-bromobiphenyl (10 g, 0.043 mol, sigma aldrich), intermediate 168-7 (12.24 g, 0.047 mol), sodium tert-butoxide (8.25 g, 0.086 mol, sigma aldrich), catalyst Pd (dba) ₂ (1.23 g , 0.0021 mol, sigma aldrich), tri-tert-Bu-phosphine (0.87 g, 0.0043 mol, sigma aldrich) was added with 150 mL of toluene, and reacted by stirring at 100 °C for 1 hour. After completion of the reaction, H ₂ 0 : MC was layered and purified by column (N-HEXANE: EA) to obtain 14.4 g of <Intermediate 168-8> (yield: 81.6%).

(9) manufacturing example 9: synthesis of compound 168

Intermediate 187-3 (10 g, 0.023 mol), Intermediate 187-4 (10.54 g, 0.026 mol), Sodium tert-butoxide (4.48 g, 0.047 mol, sigma aldrich), catalyst Pd (dba) ₂ (0.67 g, 0.0012 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.47 g, 0.0023 mol, sigma aldrich) were added with 200 mL of toluene, stirred at 100 °C for 8 hours, and reacted. After completion of the reaction, layer separation was performed on H ₂ O:MC, followed by column purification (N-HEXANE: EA) to obtain 14.2 g of Compound 168 (yield: 80.2%).

H-NMR (200 MHz, CDCl3): δ ppm, 1H (8.45/d, 7.98/d, 7.85/d, 7.81/d, 7.55/s, 7.50/m, 7.41/m) 2H (7.89/d, 7.66/m) d, 7.51/m, 7.32/m) 3H (7.52/d, 7.38/m) 6H (7.54/d, 6.69/d)

LC/MS: m/z=759 [(M+1) ⁺ ]

synthesis example 7: compound 181 synthesis

(One) manufacturing example 1: synthesis of intermediate 181-1

2,4-dibromo-6-phenyl-1,3,5-triazine (10 g, 0.032 mol, sigma aldrich), 2-naphthylboronic acid (6.55 g, 0.038 mol, sigma aldrich), potassium carbonate (10.97 g, 0.079 mol, sigma aldrich), Pd(PPh ₃ ) ₄ (1.83 g, 0.0016 mol, sigma aldrich), 150 mL of Toluene, 40 mL of Ethanol, and 20 mL of H ₂ O were added and stirred under reflux for 5 hours to react. After completion of the reaction, layer separation was performed using H ₂ 0:MC, followed by column purification (N-HEXANE:MC) to obtain 8.7 g of <Intermediate 181-1> (yield: 75.6%).

(2) manufacturing example 2: synthesis of intermediate 181-2

Intermediate 168-6 (10 g, 0.023 mol), Bis(pinacolato)dibron (7.69 g, 0.030 mol, sigma aldrich), potassium acetate (4.57 g, 0.047 mol, sigma aldrich), PdCl ₂ (dppf) (0.51 g, 0.0007 mol, sigma aldrich) and 200 mL of 1,4-Dioxane were added, followed by stirring at 95 °C for 12 hours. After completion of the reaction, H ₂ 0 was added, layer separation was performed, and column purification (N-HEXANE: MC) was performed to obtain 8.5 g of <Intermediate 181-2> (yield: 76.6%).

(3) manufacturing example 3: Synthesis of Compound 181

Intermediate 181-1 (10 g, 0.028 mol), Intermediate 181-2 (15.78 g, 0.033 mol), potassium carbonate (9.54 g, 0.069 mol, sigma aldrich), Pd(PPh ₃ ) ₄ (1.60 g, 0.0014 mol, sigma aldrich), 150 mL of Toluene, 40 mL of Ethanol, and 20 mL of H ₂ O were added and reacted by stirring under reflux for 8 hours. After completion of the reaction, layer separation was performed using H ₂ O:MC, followed by column purification (N-HEXANE: EA) to obtain 12 g of Compound 181 (yield: 78.2%).

H-NMR (200 MHz, CDCl3): δ ppm, 1H (9.09/s, 8.49/d, 8.45/d, 7.98/d, 7.92/d, 7.89/d, 7.66/d, 7.55/s, 7.52/m, 7.50/m, 7.41/m, 7.38/m, 7.32/m) 2H (8.28/d, 8.00/d, 7.59/m, 7.51/m)

LC/MS: m/z=555 [(M+1) ⁺ ]

Device Example

In an embodiment according to the present invention, the ITO transparent electrode is patterned on a glass substrate of 25 mm × 25 mm × 0.7 mm so that the light emitting area is 2 mm × 2 mm in size by using an ITO glass substrate to which the ITO transparent electrode is attached. After that, it was washed. After the substrate was mounted in a vacuum chamber and the base pressure was 1 × 10 ^-6 torr, an organic material and a metal were deposited on the ITO in the following structure.

Device Examples 1 to 12

A blue light emitting organic light emitting device having the following device structure was prepared using the compound implemented according to the present invention as a compound of the electron blocking layer, and light emitting characteristics including light emitting efficiency were measured.

ITO / hole injection layer (HAT_CN 5 nm) / hole transport layer (α-NPB 100 nm) / electron blocking layer (10 nm) / light emitting layer (20 nm) / electron transport layer (301:Liq 30 nm) / LiF (1 nm) / Al (100 nm)

In order to form a hole injection layer on the ITO transparent electrode, [HAT_CN] was used to form a hole injection layer with a thickness of 5 nm by vacuum thermal evaporation, and then a hole transport layer was formed using α-NPB. The electron blocking layer was formed to a thickness of 10 nm using Chemical Formulas 1, 6, 13, 20, 35, 40, 62, 85, 94, 112, 136, and 168, respectively. In the light emitting layer, [BH1] was used as a host compound and [BD1] was used as a dopant compound to form a film having a thickness of about 20 nm, and an electron transport layer (doped with 50% Liq of [301] compound below). A film of 30 nm, LiF 1 nm, and aluminum 100 nm was formed by a vapor deposition method to prepare an organic light emitting device.

Device Comparative Example 1

The organic light emitting device for Device Comparative Example 1 was fabricated in the same manner as the device structure of Example 1, except that TCTA was used for the electron blocking layer.

Experimental Example 1: Light Emission Characteristics of Device Examples 1 to 12

Voltage, current, and luminous efficiency of the organic light emitting device manufactured according to the above example were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the current density was 10 mA/cm 2 The voltage that becomes is defined as "driving voltage" and compared. The results are shown in [Table 1] below.

Example electronic blocking layer V cd/A QE (%) CIEx CIEy One One 4.12 8.02 7.54 0.143 0.155 2 6 4.15 8.10 7.61 0.145 0.155 3 13 4.13 8.19 7.70 0.145 0.154 4 20 4.09 8.33 7.83 0.144 0.154 5 35 4.15 8.20 7.71 0.144 0.155 6 40 4.20 8.16 7.68 0.144 0.155 7 62 4.22 8.05 7.56 0.145 0.155 8 85 4.22 8.13 7.64 0.144 0.155 9 94 4.20 8.11 7.63 0.144 0.154 10 112 4.21 8.09 7.60 0.146 0.155 11 136 4.18 8.16 7.67 0.145 0.154 12 168 4.17 8.17 7.67 0.145 0.155 Comparative Example 1 TCTA 4.20 6.40 5.30 0.145 0.156

As can be seen in [Table 1], in the case of a device employing the organic light emitting compound according to the present invention in an electron blocking layer, compared to a device employing a conventional TCTA (Comparative Example 1), luminescence efficiency, quantum efficiency, etc. It can be confirmed that the characteristics are remarkably excellent.

[HAT_CN] [α-NPB] [BH1] [BD1] [301]

[TCTA]

Device Examples 13 to 19

By using the compound implemented according to the present invention as the compound of the electron transport layer, a blue light emitting organic light emitting device having the following device structure was prepared, and light emitting characteristics including luminous efficiency were measured.

ITO / hole injection layer (HAT_CN 5 nm) / hole transport layer (α-NPB 100 nm) / light emitting layer (20 nm) / electron transport layer (compound: Liq 30 nm) / LiF (1 nm) / Al (100 nm)

To form a hole injection layer on the ITO transparent electrode, [HAT_CN] was used to form a hole injection layer with a thickness of 5 nm by vacuum thermal evaporation, and then a hole transport layer was formed using α-NPB. In the light emitting layer, [BH1] was used as a host compound and [BD1] was used as a dopant compound to form a film having a thickness of about 20 nm. 183, 190, 193, 198, and 200 were used to form a film with a thickness of 30 nm (Liq doping), and 1 nm of LiF and 100 nm of aluminum were formed by evaporation to manufacture an organic light emitting device.

Device Comparative Example 2

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner as in Example 1, except that 301 was used instead of the chemical formula implemented in the present invention for the electron transport layer.

Experimental Example 1: Light Emission Characteristics of Device Examples 13 to 19

Voltage, current, and luminous efficiency of the organic light emitting device manufactured according to the above example were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the current density was 10 mA/cm 2 The voltage that becomes is defined as "driving voltage" and compared. The results are shown in [Table 2] below.

Example electron transport layer V cd/A QE (%) CIEx CIEy 13 Formula 181 4.08 7.64 7.17 0.144 0.154 14 Formula 182 4.12 7.72 7.23 0.145 0.155 15 Formula 183 3.92 7.91 7.43 0.145 0.154 16 Formula 190 4.11 7.57 7.10 0.145 0.155 17 Formula 193 4.16 7.61 7.15 0.144 0.155 18 Formula 198 4.20 7.69 7.20 0.145 0.154 19 chemical formula 200 4.18 7.70 7.21 0.145 0.155 Comparative Example 2 301 4.2 6.20 5.24 0.145 0.156

As can be seen from [Table 2], it can be confirmed that the device employing the organic light emitting compound according to the present invention in the electron transport layer has significantly superior light emitting properties such as luminous efficiency and quantum efficiency compared to the conventional device (Comparative Example 2). can

[HAT_CN] [α-NPB] [BH1] [BD1] [301]

Claims (5)

An organic light-emitting compound represented by the following [Chemical Formula 1]:
[Formula I]

In the above [Formula I],
Y ₁ and Y ₂ are each independently O or S;
R ₁ and R ₂ are each independently any one selected from hydrogen and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
A is any one selected from the following [Structural Formula 1] to [Structural Formula 3],
[Structural Formula 1]

[Structural Formula 2]

[Structural Formula 3]

In [Structural Formula 1] to [Structural Formula 3],
X ₁ to X ₃ are the same as or different from each other and each independently represent CH or N (at least one or more of X ₁ to X ₃ is N);
L is a single bond, or any one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
L in [Formula 3] is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms (excluding anthracenylene group) and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms (excluding carbazolylene group) which one is
Ar ₁ to Ar ₃ are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms. Any one selected from an aryl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,
Ar ₃ in [Formula 3] is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms (except for anthracenyl group). ), any one selected from a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms (excluding carbazolyl group). According to claim 1,
In the definition of R ₁ , R ₂ , L and Ar ₁ to Ar ₃ , substituted or unsubstituted means that R ₁ , R ₂ , L and Ar ₁ to Ar ₃ are deuterium, a cyano group, a halogen group, a hydroxyl group, or a nitro group. , C1-24 alkyl group, C1-24 halogenated alkyl group, C1-24 alkenyl group, C1-24 alkynyl group, C1-24 heteroalkyl group, C6-24 aryl group (anthracene excluding groups), arylalkyl groups having 6 to 24 carbon atoms, heteroaryl groups having 2 to 24 carbon atoms (excluding carbazolyl groups), or heteroarylalkyl groups having 2 to 24 carbon atoms, alkoxy groups having 1 to 24 carbon atoms, and 1 to 24 carbon atoms. A group consisting of an alkylamino group having 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms An organic light emitting compound that is selected from, substituted with one or two or more substituents selected, substituted with a substituent in which two or more substituents among the substituents are connected, or does not have any substituents. According to claim 1,
[Formula I] is an organic light-emitting compound, characterized in that any one selected from the following [Formula 1] to [Formula 208]:

An organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode,
An organic electroluminescent device characterized in that at least one of the organic material layers includes at least one organic light emitting compound represented by [Chemical Formula I] according to claim 1. According to claim 4,
The organic material layer includes at least one of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
An organic electroluminescent device characterized in that at least one of the layers includes the organic light emitting compound represented by the [Chemical Formula I].

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