WO2019054599A1 - Organic light emitting compound and organic electroluminescent device using same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound, and can implement an organic electroluminescent device having excellent light emitting characteristics such as light emitting efficiency and quantum efficiency when the novel organic light emitting compound is applied to an electron blocking layer, a hole transport layer, a light emitting layer or the like.

Description

Organic light-emitting compounds and organic electroluminescent devices containing them

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent compound, and more specifically, to an organic electroluminescent device employing an organic electroluminescent compound employed in an organic electroluminescent element in the organic electroluminescent device, and an organic electroluminescent device using the same.

The present invention relates to a high efficiency (luminous efficiency 26) without sulfur compound-based semiconductor backplane and cadmium of high performance (mobility 70 ㎠ / Vs), which is supported by the Ministry of Industry and Commerce, cd / A) organic hybrid EL material / device technology development).

The organic electroluminescent device can not only form an element on a transparent substrate but also can operate at a low voltage of 10 V or less as compared with a plasma display panel (Plasma Display Panel) or an inorganic electroluminescence (EL) display, It has the advantage of excellent color and has three colors of green, blue, and red. It has recently become a subject of interest as a next generation display device.

However, in order for such an organic electroluminescent device to exhibit such characteristics, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are materials forming an organic layer in a device, However, until now, stable and efficient development of an organic material layer material for an organic electroluminescence device has not been sufficiently achieved. Therefore, development of a new material capable of improving luminescence characteristics and development of an organic layer structure in a device are continuously required.

Accordingly, the present invention provides a novel organic luminescent compound that can be employed as a host compound in an electron blocking layer, a hole transporting layer, or a luminescent layer in an organic electroluminescent device to significantly improve luminescent properties such as longevity and luminous efficiency, and organic electroluminescent Device.

In order to solve the above problems, the present invention provides an organic electroluminescent compound represented by the following formula (I) and an organic electroluminescent device comprising the same.

(I)

The specific structure and substituent of the above-mentioned formula (I) will be described later.

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

1 is a schematic diagram showing the structure of an organic luminescent compound according to the present invention.

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

The present invention relates to an organic electroluminescent compound represented by the following general formula (I), wherein an organic electroluminescent compound having a remarkably improved luminescent property such as a long life and a luminescent efficiency when employed in an organic layer such as a hole transporting layer, It is possible to realize a light emitting device.

(I)

In the above formula (I)

X ₁ and X ₂ are the same or different and are each independently from each other _{O, S, NR 3, BR} 4, R 5 -CR 6, R 7 -Si-R 8, R 9 -Ge-R 10 and R ₁₁ - Se-R ₁₂ , and each of R ₃ to R ₁₂ is independently selected from among hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms .

R ₁ and R ₂ are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 24 or less carbon atoms, a substituted or unsubstituted 3 to 30 A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, A substituted or unsubstituted C2 to C50 hetero aryl group, a substituted or unsubstituted C1 to C24 alkylamino group, a C6 to C24 arylamino group Is selected from the heteroaryl group has 6 to 24 carbon atoms.

According to an embodiment of the present invention, X ₁ and X ₂ are each O, and at least one of R ₁ and R ₂ is represented by the following formula (1).

[Structural formula 1]

In the above formula 1,

L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted C2 to C30 heteroaryl A substituted or unsubstituted arylene group having 6 to 50 carbon atoms in which at least one of substituted or unsubstituted C3 to C30 cycloalkyl is fused and a substituted or unsubstituted C3 to C30 cycloalkyl having at least one fused substituent Or an unsubstituted heteroarylene group having 2 to 50 carbon atoms (n is an integer of 1 to 3).

Ar ₁ to Ar ₂ are the same or different 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, a substituted or unsubstituted 6 to 30 carbon atom A substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, And a substituted or unsubstituted C2 to C50 heteroaryl group in which one or more ring-opened cycloalkyl having 3 to 30 carbon atoms is fused.

The Ar ₁ to Ar ₂ may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring. The carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may be N, S And < RTI ID = 0.0 > O, < / RTI >

The organic luminescent compound according to the present invention has excellent skeletal structure and excellent luminescent properties such as longevity and luminescence efficiency of the organic light emitting device employing the organic compound in the organic layer depending on the characteristics of the substituent to be introduced.

In the definition of R ₁ to R ₁₂ , L and Ar ₁ to Ar ₂ , the substitution or unsubstitution means that R ₁ to R ₁₄ , L and Ar ₁ to Ar ₂ are deuterium, cyano group, halogen group, A nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 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, an alkoxy group having 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an aryl group having 1 to 24 carbon atoms 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, Substituted with a substituent, or two or more of the substituents in the substituent are substituted with a connected group, or have no substituent.

Specific examples of the substituted aryl group include a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group and an anthracenyl group substituted with other substituents do.

The substituted heteroaryl group includes 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, An imidazole group, a benzoxazole group, a benzothiazole group, a benzoxazole group, a dibenzothiophenyl group, a dibenzofurane group and the like are substituted with other substituents.

In the present invention, examples of the substituents will be specifically described below, but the present invention is not limited thereto.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, A tert-butyl group, a tert-butyl group, a 2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, 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 are 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 at least one hydrogen atom contained 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, dimethylpurylsilyl And the like.

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 and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluororanthrene group, but the scope of the present invention is not limited to these examples.

More specifically, at least one hydrogen atom of the aryl group may be substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" are independently of each other an alkyl group having 1 to 10 carbon atoms and in this case an "alkylamino group"), an amidino group, An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroatom having 1 to 24 carbon atoms, An alkyl group having 6 to 24 carbon atoms, 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,

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

In the present invention, the heteroaryl group is a hetero ring group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably 2 to 30 carbon atoms. Examples thereof include a thiophene group, a furan group, a furyl 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 pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofuranyl group, a phenanthroline group, An oxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and the like, but are not limited thereto.

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

In the present invention, a fluorenyl group is a structure in which two cyclic organic compounds are connected via one atom,

,

.

In the present invention, a fluorenyl group includes a structure of an open fluorenyl group, wherein an open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected via one atom For example,

,

.

In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, But are not limited to, an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group and a triphenylamine group.

In the present invention, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

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 confirmed in the specific compounds described below.

The organic luminescent compound according to the present invention represented by the above-mentioned formula (I) can be used as an organic material layer of an organic light emitting device due to its structural specificity as described above. More specifically, A blocking layer, a hole transporting layer, or a host compound of a light emitting layer.

Preferred examples of the compound represented by the formula (I) according to the present invention include, but are not limited to, the following compounds.

An organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituents into the core structure having the above structure can be synthesized. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, an electron transporting layer material and an electron blocking layer material used in manufacturing an organic electroluminescent device into the above structure, In particular, when the compound of the formula (I) according to the present invention is employed as a host material of an electron blocking layer, a hole transporting layer or a light emitting layer, and particularly in an electron blocking layer, the luminescence The characteristics can be further improved.

The organic luminescent compound according to the present invention can be applied to an organic electroluminescent device according to a conventional production method.

The organic electroluminescent device according to one embodiment of the present invention may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic electroluminescent compound according to the present invention may be used for an organic material layer And can be manufactured using conventional device manufacturing methods and materials.

The organic material layer of the organic electroluminescent device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and an electron blocking layer. However, it is not so limited and may include fewer or greater numbers of organic layers.

Therefore, in the organic electroluminescent device according to the present invention, the organic material layer may include at least one of a hole transporting layer, an electron blocking layer and a light emitting layer, and at least one of the layers may be an organic light emitting ≪ / RTI > compounds.

The organic light emitting device according to the present invention may be formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation A hole transporting layer, an electron blocking layer, a light emitting layer, and an electron transporting layer on the anode, and then depositing a material usable as a cathode thereon.

In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer, but may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.

As the anode material, a material having a large work function is preferably used so as to smoothly inject holes into the organic material layer. Specific examples of the cathode 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), indium zinc oxide (IZO) metal oxides, ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) , Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof; a multilayer such as LiF / Al or LiO ₂ / Structural materials, and the like, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

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

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazol-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and A benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, and the like.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable. Specific examples thereof include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex.

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

Also, the organic luminescent compound according to the present invention can act on a principle similar to that applied to an organic luminescent device in an organic electronic device including an organic solar cell, an organophotoreceptor, an organic transistor and the like.

Hereinafter, synthesis examples and device embodiments of preferred compounds are shown to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

Synthesis Example 1: Synthesis of Compound 1

(1) Production Example 1: Synthesis of Intermediate 1-1

2-fluorophenylboronic acid (14.50 g, 0.055 mol, Sigma Aldrich), potassium carbonate (18.85 g, 0.136 mol, Sigma Aldrich), Pd (PPh ₃ ), 2-iodophenol (10 g, 0.046 mol, ) ₄ (2.63 g, 0.0023 mol, Sigma aldrich), 150 mL of Toluene, 40 mL of Ethanol, and 20 mL of H ₂ O were added and reacted by refluxing for 5 hours. After completion of the reaction, the reaction mixture was subjected to layer separation using H ₂ O: MC and then subjected to column purification (N-HEXANE: MC) to obtain 11.4 g (yield 79.85%) of Intermediate 1-1.

(2) Preparation Example 2: Synthesis of intermediate 1-2

300 mL of N- methyl-2-pyrrolidone was added to the mixture, and the mixture was reacted at 180 ° C for 3 hours under reflux with stirring. After completion of the reaction, layer separation was performed using H ₂ O: Tol, and column purification (N-HEXANE: EA) was conducted to obtain 7.5 g (yield 80%) of <Intermediate 1-2>.

(3) Preparation Example 3: Synthesis of intermediate 1-3

Add bromine (6.52 g, 0.041 mol, Sigma aldrich) slowly dropwise to the reaction mixture, stir for 1 hour, remove the ice-bath And the mixture was reacted at room temperature for 12 hours with stirring. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC, followed by column purification (N-HEXANE: MC) to obtain 10 g (yield 78.8%) of Intermediate 1-3.

(4) Production Example 4: Synthesis of Intermediate 1-4

PdCl ₂ (dppf) (0.59 g, 0.035 mol, Sigma Aldrich), potassium acetate (5.26 g, 0.054 mol, Sigma aldrich), Bis (pinacolato) dibron (8.85 g, 0.0008 mol, Sigma aldrich) and 1,4-dioxane (200 mL), and the mixture was reacted at 95 ° C for 12 hours with stirring. After completion of the reaction, the reaction mixture was poured into H ₂ O, layer separation was performed, and column purification (N-HEXANE: MC) was conducted to obtain 7.8 g (yield 78%) of Intermediate 1-4.

(5) Preparation Example 5: Synthesis of intermediate 1-5

(13.57 g, 0.036 mol), potassium carbonate (10.47 g, 0.076 mol, Sigma aldrich), Pd (PPh ₃ ) ₄ (1.75 g, 0.036 mol), 1,2-diiodobenzene (10 g, 0.030 mol, , 0.0015 mol, sigma aldrich), 200 mL of THF and 40 mL of H ₂ O, and the mixture was stirred under reflux for 12 hours. After completion of the reaction, the reaction mixture was subjected to layer separation using H ₂ O: MC and column purification (N-HEXANE: MC) was conducted to obtain 10.9 g (yield 80%) of Intermediate 1-5.

(6) Preparation Example 6: Synthesis of intermediate 1-6

Sodium tert-butoxide (8.25 g, 0.086 mol, Sigma aldrich), Catalyst Pd (dba) ₂ (0.35 g, 0.042 mol, Sigma Aldrich), 4-aminobiphenyl 150 mL of Toluene was added to 1.23 g, 0.0021 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.87 g, 0.0043 mol, Sigma aldrich) and reacted at 100 ° C for 1 hour. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC, followed by column purification (N-HEXANE: EA) to obtain 11.1 g (yield 80.5%) of Intermediate 1-6.

(7) Production Example 7: Synthesis of Intermediate 1-7

Intermediate 1-5 (10 g, 0.022 mol), intermediate 1-6 (7.87 g, 0.025 mol), sodium tert-butoxide (4.28 g, 0.045 mol, sigma aldrich), catalyst Pd (dba) ₂ tert-Bu-phosphine (0.45 g, 0.0022 mol, Sigma aldrich) was reacted with 150 mL of Toluene at 100 ° C for 6 hours. After completion of the reaction, the mixture was subjected to column separation with H ₂ O: MC and column purification (N-HEXANE: EA) was conducted to obtain 11.3 g (yield 79%) of <Intermediate 1-7>.

(8) Production Example 8: Synthesis of Intermediate 1-8

Intermediate 1-3 (10 g, 0.027 mol) , phenylboronic acid (3.92 g, 0.032 mol, sigma aldrich), potassium carbonate (9.26 g, 0.067 mol, sigma aldrich), Pd (PPh 3) 4 (1.55 g, 0.0013 mol , sigma aldrich), 200 mL of THF, 40 mL of H ₂ O, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction mixture was subjected to layer separation using H ₂ O: MC and purified by column (N-HEXANE: MC) to obtain 6.8 g (yield 78.5%) of Intermediate 1-8.

(9) Preparation Example 9: Synthesis of Intermediate 1-9

(10 g, 0.031 mol), Bis (pinacolato) dibron (10.21 g, 0.040 mol, Sigma Aldrich), potassium acetate (6.07 g, 0.062 mol, SigmaAldrich), PdCl ₂ (dppf) 0.0009 mol, Sigma aldrich) and 1,4-dioxane (200 mL), and the mixture was reacted at 95 ° C for 12 hours with stirring. After completion of the reaction, the reaction mixture was poured into H ₂ O, layer separation was performed, and column purification (N-HEXANE: MC) was conducted to obtain 9 g (yield 78.6%) of <Intermediate 1-9>.

(10) Production Example 10: Synthesis of Compound 1

Intermediate 1-7 (10 g, 0.0156 mol) , intermediate 1-9 (6.91 g, 0.0187 mol) , potassium carbonate (5.38 g, 0.039 mol, sigma aldrich), Pd (PPh 3) 4 (0.90 g, 0.0008 mol, sigma aldrich), 200 mL of THF, 40 mL of H ₂ O, and the mixture was stirred under reflux for 6 hours. After completion of the reaction, the mixture was subjected to layer separation using H ₂ O: MC and then subjected to column purification (N-HEXANE: EA) to obtain 10 g (yield: 79.7%) of Compound 1.

M, 6H (7.54 / d, 7.68 / d, 7.68 / d, 7.66 / d, 7.38 / 7.52 / d, 7.51 / m, 6.69 / d)

LC / MS: m / z = 805 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 2: Compound 38 Synthesis

(1) Production example 1: Synthesis of intermediate 38-1

Sodium tert-butoxide (15.56 g, 0.16 mol, Sigma aldrich), Catalyst Pd (dba) ₂ (2.33 g, 0.097 mol, Sigma Aldrich), 4-bromodibenzofuran (20 g, 300 mL of Toluene was added to tri-tert-Bu-phosphine (1.64 g, 0.008 mol, Sigma aldrich) and reacted at 100 ° C for 2 hours. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC and then subjected to column purification (N-HEXANE: EA) to obtain 19.2 g (yield 70.7%) of Intermediate 38-1.

(2) Production example 2: Synthesis of intermediate 38-2

Intermediate 1-5 (10 g, 0.022 mol) , intermediate 38-1 (8.22 g, 0.045 mol) , Sodium tert-butoxide (4.28 g, 0.045 mol, sigma aldrich), catalyst _{Pd (dba) 2 (0.64 g} , 0.0011 150 mL of Toluene was added to tri-tert-Bu-phosphine (0.45 g, 0.0022 mol, Sigma aldrich) and reacted at 100 ° C for 4 hours. After completion of the reaction, the reaction mixture was subjected to column separation with H ₂ O: MC and column purification (N-HEXANE: EA) yielded 11.6 g (yield 79.3%) of Intermediate 38-2.

(3) Production Example 3: Synthesis of Compound 38

Intermediate 38-2 (10 g, 0.015 mol) , intermediate 1-9 (6.77 g, 0.018 mol) , potassium carbonate (5.26 g, 0.038 mol, sigma aldrich), Pd (PPh 3) 4 (0.88 g, 0.0008 mol, sigma aldrich), 200 mL of THF, 40 mL of H ₂ O, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, layer separation was performed using H ₂ O: MC and column purification (N-HEXANE: EA) was conducted to obtain 9.8 g (yield 78.5%) of Compound 38.

7.89 / d, 7.66 / d, 7.68 / d, 7.41 / m) 2H (7.87 / d, 7.68 / d, 7.41 / 7.38 / m, 7.32 / m) 4H (7.54 / d, 7.52 / d, 7.51 / m, 6.69 / d)

LC / MS: m / z = 819 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 3: Synthesis of Compound 70

(1) Production Example 1: Synthesis of Intermediate 70-1

(7.30 g, 0.076 mol, Sigma aldrich), 2-bromodibenzo [b, d] thiophene (10 g, 0.038 mol, (dba) ₂ (1.09 g, 0.0019 mol, Sigma aldrich) and tri-tert-Bu-phosphine (0.77 g, 0.0038 mol, Sigma aldrich) were added 150 mL of Toluene and reacted at 100 ° C for 4 hours. After the completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC, followed by column purification (N-HEXANE: EA) to obtain 10.6 g (yield: 79.4%) of Intermediate 70-1.

(2) Production example 2: Synthesis of intermediate 70-2

Intermediate 1-5 (10 g, 0.038 mol), intermediate 70-1 (6.78 g, 0.042 mol), sodium tert-butoxide (4.28 g, 0.045 mol, sigma aldrich), catalyst Pd (dba) ₂ 150 mL of Toluene was added to tri-tert-Bu-phosphine (0.45 g, 0.0022 mol, Sigma aldrich) and reacted at 100 ° C for 4 hours. After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC, followed by column purification (N-HEXANE: EA) to obtain 12 g (yield 80.1%) of Intermediate 70-2.

(3) Production Example 3: Synthesis of Compound 70

Intermediate 70-2 (10 g, 0.015 mol) , intermediate 1-9 (6.61 g, 0.018 mol) , potassium carbonate (5.14 g, 0.037 mol, sigma aldrich), Pd (PPh 3) 4 (0.86 g, 0.0007 mol, Sigma aldrich), 150 mL of Toluene, 40 mL of EtOH, 20 mL of H ₂ O, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, the mixture was subjected to layer separation using H ₂ O: MC and purified by column (N-HEXANE: EA) to obtain 9.9 g (yield: 79.7%) of Compound 70.

7.89 / d, 7.73 / d, 7.50 / m, 7.40 / s, 7.16 / m, 6.87 / m, 6.86 / d) 2H (7.89 / d, 7.87 d, 7.68 d, 7.66 d, 7.41 m, 7.38 m, 7.32 m, 7.08 d) 3H (7.54 d, 7.52 m, 6.69 d)

LC / MS: m / z = 835 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 4: Synthesis of Compound 113

(1) Preparation Example 1: Synthesis of intermediate 113-1

Sodium tert-butoxide (4.28 g, 0.045 mol, Sigma aldrich), Catalyst Pd (dba) ₂ (0.64 g, 0.0011 mol), biphenylamine (4.14 g, 0.025 mol, 150 mL of Toluene was added to tri-tert-Bu-phosphine (0.45 g, 0.0022 mol, Sigma aldrich) and reacted at 100 ° C for 3 hours. After the completion of the reaction, the reaction mixture was subjected to layer separation into H ₂ O: MC and purified by column (N-HEXANE: EA) to obtain 9 g (yield: 82.4%) of Intermediate 113-1.

(2) Production example 2: Synthesis of intermediate 113-2

Potassium acetate (4 g, 0.041 mol, SigmaAldrich), PdCl ₂ (dppf) (0.45 g, 0.026 mol) was added to a solution of intermediate 113-1 (10 g, 0.020 mol), Bis (pinacolato) dibron 0.0006 mol, Sigma aldrich) and 1,4-dioxane (200 mL), and the mixture was reacted at 95 DEG C for 12 hours with stirring. After completion of the reaction, the reaction mixture was poured into H ₂ O, layer separation was performed, and column purification (N-HEXANE: MC) was conducted to obtain 8.3 g (yield 75.7%) of Intermediate 113-2.

(3) Preparation Example 3: Synthesis of Compound 113

Intermediate 113-1 (10 g, 0.020 mol) , intermediate 113-2 (13.15 g, 0.025 mol) , potassium carbonate (7.05 g, 0.051 mol, sigma aldrich), Pd (PPh 3) 4 (1.18 g, 0.0010 mol, sigma aldrich), 200 mL of THF, 40 mL of H ₂ O, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, the layers were separated using H ₂ O: MC and purified by column (N-HEXANE: EA) to obtain 13.2 g (yield 78.8%) of Compound 113.

D, 6.81 / m, 6.69 / d, 7.68 / d, 7.66 / d, 7.38 / d) 8H (7.20 / m, 6.63 / d)

LC / MS: m / z = 820 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 5: Synthesis of Compound 129

(1) Preparation Example 1: Synthesis of intermediate 129-1

Sodium tert-butoxide (7.04 g, 0.073 mol, Sigma Aldrich), 4-aminobiphenyl (7.43 g, 0.044 mol, Sigma Aldrich), 2-bromo-9,9-dimethyl-9H- 150 mL of Toluene was added to the catalyst Pd (dba) ₂ (1.05 g, 0.0018 mol, sigma aldrich), tri-tert-Bu-phosphine (0.74 g, 0.0037 mol, Sigma aldrich), and the mixture was stirred at 100 ° C. for 5 hours Lt; / RTI &gt; After completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC, followed by column purification (N-HEXANE: MC) to obtain 10.3 g (yield: 77.8%) of <Intermediate 129-1>.

(2) Production example 2: Synthesis of intermediate 129-2

Intermediate 1-5 (10 g, 0.022 mol), intermediate 129-1 (8.85 g, 0.025 mol), sodium tert-butoxide (4.28 g, 0.045 mol, sigma aldrich), catalyst Pd (dba) ₂ 150 mL of Toluene was added to tri-tert-Bu-phosphine (0.45 g, 0.0022 mol, Sigma aldrich) and reacted at 100 ° C for 5 hours. After the completion of the reaction, the reaction mixture was subjected to layer separation with H ₂ O: MC, followed by column purification (N-HEXANE: EA) to obtain 12 g (yield 78.9%) of <intermediate 129-2>.

(3) Preparation Example 3: Synthesis of intermediate 129-3

(2.88 g, 0.029 mol, Sigma Aldrich), PdCl ₂ (dppf) (0.32 g, 0.019 mol, Sigma Aldrich), Bis (pinacolato) dibron (4.84 g, 0.0004 mol, Sigma aldrich) and 1,4-dioxane (200 mL), and the mixture was reacted at 95 DEG C for 12 hours with stirring. After completion of the reaction, the reaction mixture was poured into H ₂ O and the mixture was subjected to column separation, followed by column purification (N-HEXANE: MC) to obtain 8.5 g (yield: 79.5%) of Intermediate 129-3.

(4) Production Example 4: Synthesis of Compound 129

Intermediate 129-2 (10 g, 0.015 mol) , intermediate 129-3 (13.15 g, 0.025 mol) , potassium carbonate (7.05 g, 0.051 mol, sigma aldrich), Pd (PPh 3) 4 (1.18 g, 0.0010 mol, sigma aldrich), 200 mL of Toluene, 40 mL of EtOH and 20 mL of H ₂ O, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, the mixture was subjected to layer separation using H ₂ O: MC and then subjected to column purification (N-HEXANE: EA) to obtain 13.4 g (yield 75.9%) of Compound 129.

M, 7.28 / m, 6.75 (d, 7.68 / d, 7.66 / d, 7.62 / d, 7.55 / d, 7.41 / 12H (1.72 / s), 8H (7.54 / d, 6.69 / m)

LC / MS: m / z = 1205 [(M + 1) ^&lt; ^{+ &}

Synthesis Example 6: Synthesis of Compound 158

(1) Preparation Example 1: Synthesis of intermediate 158-1

(0.14 g, 0.020 mol, Sigma Aldrich), potassium acetate (3.05 g, 0.031 mol, Sigma Aldrich), PdCl ₂ (dppf) (0.34 g, 0.0005 mol, Sigma aldrich) and 1,4-dioxane (200 mL), and the mixture was reacted at 95 ° C for 12 hours with stirring. After completion of the reaction, the reaction mixture was poured into H ₂ O, layer separation was performed, and the product was subjected to column purification (N-HEXANE: MC) to obtain 8.5 g (yield: 79.2%) of Intermediate 158-1.

(2) Production Example 2: Synthesis of Compound 158

Intermediate 38-2 (10 g, 0.015 mol) , intermediate 158-1 (12.60 g, 0.018 mol) , potassium carbonate (6.32 g, 0.046 mol, sigma aldrich), Pd (PPh 3) 4 (0.88 g, 0.0008 mol, sigma aldrich), 200 mL of Toluene, 40 mL of EtOH and 20 mL of H ₂ O, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, layer separation was carried out using H ₂ O: EA and column purification (N-HEXANE: EA) was conducted to obtain 13.6 g (yield 78.4%) of compound 158.

7.89 / d, 7.66 / d, 7.41 / m, 7.7 / d, 7.68 / d) 2H (7.87 / d, 7.68 / 7.38 / m) 6H (7.52 / d, 7.51 / m) 10H (7.54 / d, 6.69 / d)

LC / MS: m / z = 1138 [(M + 1) ^&lt; ^{+ &}

Device Example

In the embodiment according to the present invention, the ITO transparent electrode is formed by patterning an ITO glass substrate having an ITO transparent electrode on a glass substrate of 25 mm x 25 mm x 0.7 mm so as to have a light emitting area of 2 mm x 2 mm And then washed. After the substrate was mounted in a vacuum chamber and the base pressure was adjusted to 1 × 10 ^-6 torr, organic matter and metal were deposited on the ITO by the following structure.

Device Embodiments 1 through 12

A blue light emitting organic electroluminescent device having the following device structure was prepared by using a compound represented by the formula [I] according to the present invention as a compound of the electron blocking layer, and the luminescent characteristics including the luminescent efficiency were measured.

Electron transport layer (201 nm Liq 30 nm) / LiF (1 nm) / ITO / hole injection layer (HAT_CN 5 nm) / hole transport layer (α-NPB 100 nm) / electron blocking layer (10 nm) / Al (100 nm)

In order to form a hole injection layer on the ITO transparent electrode, the hole injection layer was formed to a thickness of 5 nm by vacuum thermal deposition method using [HAT_CN], and then the hole transport layer was formed by using α-NPB. The electron blocking layer was formed to have a thickness of 10 nm by using the chemical vapor deposition method of the present invention, which is represented by Chemical Formula 1, 10, 17, 38, 56, 70, 82, 93, 113, 129, Further, an electron transport layer (doped with Liq 50% of the following compound [201]) was further formed on the light emitting layer so as to have a thickness of about 20 nm by using [BH1] as a host compound and [BD1] 30 nm, LiF 1 nm and aluminum 100 nm were deposited by a vapor deposition method to produce an organic electroluminescent device.

Device Comparative Example 1

An organic electroluminescent device for Device Comparison Example 1 was fabricated in the same manner except that TCTA was used as an electron blocking layer in the device structure of Example 1. [

EXPERIMENTAL EXAMPLE 1: Luminescent characteristics of element embodiments 1 to 12

The voltage, current and luminous efficiency of the organic EL device were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research). The current density was 10 mA / Is defined as " driving voltage " The results are shown in Table 1 below.

Example	Electronic stop layer	V	cd / A	QE (%)	CIEx	CIEy
One	One	4.19	8.05	6.80	0.145	0.154
2	10	4.21	8.01	6.77	0.145	0.155
3	17	4.20	8.11	6.85	0.145	0.154
4	38	4.16	8.20	6.95	0.145	0.153
5	56	4.24	8.06	6.81	0.144	0.154
6	70	4.20	8.12	6.85	0.145	0.155
7	82	4.18	8.02	6.78	0.144	0.154
8	93	4.19	8.15	6.89	0.145	0.155
9	113	4.17	8.13	6.86	0.146	0.156
10	129	4.20	8.18	6.93	0.145	0.154
11	137	4.23	8.04	6.80	0.145	0.155
12	158	4.22	8.14	6.88	0.144	0.154
Comparative Example 1	TCTA	4.20	6.40	5.30	0.145	0.156

It can be seen from the results shown in [Table 1] that, when the electron blocking layer according to the present invention is applied to a compound device, the light emitting properties such as luminous efficiency and quantum efficiency are remarkably superior to those of the conventional device (comparative example) .

[HAT_CN] [? -NPB] [BH1]

[BD1] [201]

[TCTA]

Device Embodiments 13 to 24

An organic electroluminescent device having the following device structure was manufactured using the compound represented by formula (I) according to the present invention as a compound of the hole transport layer, and the luminescent characteristics including the luminous efficiency were measured.

InP QDs / hole transport layer (50 nm) / MoO ₃ (10 nm) / Al (100 nm) / ITO / ZnO (40 nm) / PFN

The ZnO nanoparticle solution was spin-coated on the ITO transparent electrode to a thickness of 40 nm, and the solvent was removed in a vacuum oven at 150 ° C. Then, a 10 nm thick PFN solution was spin-coated and heat-treated. Then, an InP QD dispersion was spin-coated to form a film. After that, the substrate is mounted in a vacuum chamber, and the base pressure is adjusted to 1 × 10 ^-6 torr. Thereafter, a hole transport layer is formed on the surface of the hole transport layer of Formula 1, 10, 17, 38, 56, 70, 82, 93, , 137, and 158, respectively. MoO ₃ was deposited to a thickness of about 10 nm, and aluminum was deposited to a thickness of 100 nm by vapor deposition to prepare an organic electroluminescent device.

Device Comparative Example 2

An organic electroluminescent device for Device Comparison Example 2 was fabricated in the same manner except that TCTA was used as a hole transport layer in the device structure of Example 13. [

Experimental Example 2: Luminescent characteristics of the device examples 13 to 24

The voltage, current and luminous efficiency of the organic EL device were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research). The current density was 10 mA / Is defined as " driving voltage " The results are shown in Table 2 below.

Example	Hole transport layer	V	cd / A	EL (nm)
13	One	3.25	13.71	543
14	10	2.98	13.25	542
15	17	2.68	12.54	543
16	38	2.87	12.82	545
17	56	3.14	13.42	540
18	70	3.21	14.61	541
19	82	3.05	13.44	544
20	93	2.94	13.08	542
21	113	3.19	14.63	540
22	129	3.30	15.01	544
23	137	3.12	15.43	547
24	158	3.24	14.04	542
Comparative Example 2	TCTA	3.68	7.7	539

When the hole transport layer according to the present invention is applied to a compound device, it can be confirmed that the luminous efficiency and luminescence characteristics are significantly superior to those of the conventional device (Comparative Example 2).

[PFN] [TCTA]

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

Claims (7)

1. An organic light-emitting compound represented by the following formula (I):

   (I)

   

   In the above formula (I)

   X ₁ and X ₂ are the same or different and are each independently from each other _{O, S, NR 3, BR} 4, R 5 -CR 6, R 7 -Si-R 8, R 9 -Ge-R 10 and R ₁₁ - Se-R ₁₂ , and each of R ₃ to R ₁₂ is independently selected from among hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, ,

   R ₁ and R ₂ are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 24 or less carbon atoms, a substituted or unsubstituted 3 to 30 A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, A substituted or unsubstituted C2 to C50 hetero aryl group, a substituted or unsubstituted C1 to C24 alkylamino group, a C6 to C24 arylamino group Is selected from the heteroaryl group has 6 to 24 carbon atoms.
2. The method according to claim 1,

   Wherein at least one of R &lt; ₁ &gt; and R &lt; ₂ &gt; is the following formula [1]

   [Structural formula 1]

   

   In the above formula 1,

   L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted C2 to C30 heteroaryl A substituted or unsubstituted arylene group having 6 to 50 carbon atoms in which at least one of substituted or unsubstituted C3 to C30 cycloalkyl is fused and a substituted or unsubstituted C3 to C30 cycloalkyl having at least one fused substituent Or an unsubstituted heteroarylene group having 2 to 50 carbon atoms (n is an integer of 1 to 3)

   Ar ₁ to Ar ₂ are the same or different 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, a substituted or unsubstituted 6 to 30 carbon atom A substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl, A substituted or unsubstituted C2 to C50 heteroaryl group in which one or more ring-opened cycloalkyls having 3 to 30 carbon atoms is fused,

   The Ar ₁ to Ar ₂ may be bonded to each other or may be connected to adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring. The carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may be N, S And &lt; RTI ID = 0.0 &gt; O, &lt; / RTI &gt;
3. The method according to claim 1,

   And X &lt; _{1 &gt;} and X &lt; ₂ &gt; are each O.
4. 3. The method according to claim 1 or 2,

   In the definition of R ₁ to R ₁₂ , L and Ar ₁ to Ar ₂ , the substitution or unsubstitution means that R ₁ to R ₁₂ , L and Ar ₁ to Ar ₂ are deuterium, cyano group, halogen group, , An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, 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, an alkoxy group having 24 carbon atoms, an alkylamino group having 1 to 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, A substituted or an organic light emitting compound or substituted with a substituent of two or more of the substituent the substituent is connected, or means that also does not have any substituent.
5. The method according to claim 1,

   The organic luminescent compound according to claim 1, wherein the compound represented by Formula (I) is any one selected from the following Formulas (1) to (187)

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   
6. 1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,

   Wherein at least one of the organic material layers comprises at least one organic light emitting compound represented by Formula (I) according to Claim 1.
7. The method according to claim 6,

   Wherein 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,

   Wherein at least one of the layers comprises an organic light emitting compound represented by the formula (I).

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