KR20190027545A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light-emitting compound and an organic electroluminescent device comprising the same. The organic light-emitting compound is represented by chemical formula (I). When the organic light-emitting compound is applied in an electron blocking layer, a hole transport layer or a light-emitting layer, the organic electroluminescent device having excellent luminescent properties such as luminescent efficiency and quantum efficiency can be implemented.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

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 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.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a schematic diagram showing the structure of an organic luminescent compound represented by formula (I) 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)

R ₁ to R ₃ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted C6- A substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a diarylamino group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroarylamino group having 5 to 40 carbon atoms.

In the organic electroluminescent compound according to the present invention represented by Formula (I), at least one of R ₁ to R ₃ is represented by the following Structural Formula 1, Layer, a hole transporting layer, etc. have excellent light emitting properties such as light emitting efficiency.

When R ₁ to R ₃ do not have the above-mentioned structural formula 1, they are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms .

[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.

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 >

According to a preferred embodiment, the L is a single bond or a substituted or unsubstituted arylene group of a ring having 6 to 30 carbon atoms, or a substituted or unsubstituted number of date heteroarylene having a carbon number of 2 to 50 rings, Ar ₁ to Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms Substituted or unsubstituted C2 to C50 heteroaryl group in which one or more substituted or unsubstituted C6 to C50 aryl and substituted or unsubstituted C3 to C30 cycloalkyl are fused together, Can be selected.

Ar ₁ to Ar ₂ may be a condensed ring group including an N-containing five-membered to six-membered ring by bonding to each other.

On the other hand, the R ₁ to R _3, L and Ar ₁ to the definition of Ar _2, substituted or non-substituted ring is the R ₁ to R _3, L and Ar ₁ to Ar ₂ is heavy hydrogen, a cyano group, a halogen group, a hydroxyl 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 6 to 24 carbon atoms An amino group, a heteroarylamino group having 5 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and an aryloxy group having 6 to 24 carbon atoms, Or substituted by group, or substituted by the substituents of two or more of the substituent the substituent is connected, it means that that or have any 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 ring organic compounds are connected via one atom, for example, and the like.

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 through 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.

Synthetic example  1: Synthesis of Compound (4)

(One) Manufacturing example  1: Synthesis of Intermediate 4-1

1-iodo-2-nitrobenzene (11.48 g, 0.046 mol, Sigma aldrich), potassium carbonate (15.94 g, 0.115 mol, Sigma aldrich), 3-bromo-4-hydroxyphenylboronic acid (10 g, 0.046 mol, Yurii) 150 mL of THF and 40 mL of water were added to Pd (PPh ₃ ) ₄ (2.66 g, 0.0023 mol, Sigma aldrich) and reacted at 60 ° C for 12 hours with stirring. After completion of the reaction, the reaction mixture was subjected to column separation with H ₂ O: MC, followed by column purification (N-HEXANE: EA) to obtain 11.7 g (yield: 86%) of <Intermediate 4-1>.

(2) Manufacturing example  2: Synthesis of intermediate 4-2

250 mL of an intermediate 4-1 (15 g, 0.051 mol), triphenylphosphine (40.13 g, 0.153 mol, sigma aldrich) and 1,2-dichlorobenzene was added and reacted at 180 ° C for 12 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) to obtain <Intermediate 4-2> (10.6 g, yield 79%).

(3) Manufacturing example  3: Synthesis of intermediate 4-3

Intermediate 4-2 (10 g, 0.02 mol) , phenylboronic acid (8.37 g, 0.069 mol, sigma aldrich), potassium carbonate (19.77 g, 0.143 mol, sigma aldrich), Pd (PPh 3) 4 (3.31 g, 0.003 mol , sigma aldrich), 150 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: EA and then subjected to column purification (N-HEXANE: EA) to obtain 11.4 g (yield: 81.4%) of Intermediate 4-3.

(4) Manufacturing example  4: Synthesis of intermediate 4-4

Iodobenzene (9.4 g, 0.046 mol, Sigma Aldrich), potassium carbonate (13.32 g, 0.096 mol, SigmaAldrich), Cu (4.90 g, 0.077 mol, Sigma Aldrich), dibenzo -18-crown-6 (1.39 g, 0.004 mol, Sigma Aldrich) and 150 mL of dimethylformamide, and the mixture was reacted at 150 ° C for 12 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 10 g (yield: 77.3%) of Intermediate 4-4.

(5) Manufacturing example  5: Synthesis of intermediate 4-5

Pyridine (6.1 g, 0.078 mol, Sigma Aldrich), potassium carbonate (16.48 g, 0.120 mol, Sigma Aldrich) and 160 mL of MC were added and the mixture was cooled to 0 ° C and trifluoromethanesulfonic anhydride (18.5 g, 0.066 mol, Sigma Aldrich) was slowly dropped and reacted at 25 ° C for 1 hour with stirring. After completion of the reaction, hydrochloric acid was added thereto, stirred, and layer separation was carried out using H ₂ O: MC, followed by column purification (N-HEXANE) to obtain 6 g (yield: 43%) of Intermediate 4-5.

(6) Manufacturing example  6: Synthesis of intermediate 4-6

Sodium tert-butoxide (7.47 g, 0.078 mol, Sigma aldrich), Catalyst Pd (dba) ₂ (1.12 g, 0.058 mol, Sigma Aldrich), 9- bromophenanthrene (10 g, 0.039 mol, , 0.002 mol, Sigma aldrich) and tri-tert-Bu-phosphine (0.79 g, 0.004 mol, Sigma aldrich) were added and reacted at 100 ° C for 4 hours. 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 g (yield: 76.4%) of Intermediate 4-6.

(7) Manufacturing example  7: Synthesis of compound 4

Intermediate 4-5 (10 g, 0.039 mol) , intermediate 4-6 (4.71 g, 0.051 mol) , cesuim carbonate (19.01 g, 0.058 mol, sigma aldrich), catalyst _{Pd (OAc) 2 (0.61 g} , 0.0027 mol, Sigma Aldrich), xant-phos (2.70 g, 0.0047 mol, Sigma Aldrich) and 150 mL of Toluene were added and reacted at 100 ° C for 4 hours with stirring. After completion of the reaction, the mixture was subjected to column separation with H ₂ O: MC and then subjected to column purification (N-HEXANE: EA) to obtain 17.2 g (yield: 75.4%) of Compound 4.

M, 7.31 / m, 7.25 / m, 6.91 / s, 6.81 / m, 7.95 / d, 7.95 / 7.51 / m, 7.50 / d, 7.20 / m, 6.63 / d)

LC / MS: m / z = 586 [(M + 1) ^&lt; ^{+ &}

Synthetic example  2: Compound 24 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 24-1

Sodium tert-butoxide (7.04 g, 0.073 mol, Sigma Aldrich), aniline (5.11 g, 0.055 mol, Sigma Aldrich), 2-bromo-9,9-dimethyl-9H- , 150 mL of toluene was added to the catalyst Pd (dba) ₂ (1.05 g, 0.002 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.74 g, 0.004 mol, sigma aldrich) . After completion of the reaction, the reaction mixture was poured into H ₂ O and the mixture was subjected to column separation (N-HEXANE: MC) to obtain 8.2 g (yield 78.5%) of Intermediate 24-1.

(2) Manufacturing example  2: Synthesis of Compound 24

Intermediate 4-5 (10 g, 0.030 mol) , intermediate 24-1 (3.1 g, 0.045 mol) , cesuim carbonate (14.57 g, 0.045 mol, sigma aldrich), catalyst _{Pd (OAc) 2 (0.47 g} , 0.0021 mol, Sigma Aldrich), xant-phos (2.07 g, 0.0036 mol, Sigma Aldrich) and 150 mL of Toluene were added and reacted at 100 ° C for 4 hours with stirring. After completion of the reaction, the mixture was subjected to column separation with H ₂ O: MC, followed by column purification (N-HEXANE: EA) to obtain 13.6 g (yield 75.7%) of Compound 24.

M, 7.48 / m, 7.48 / m, 7.75 / d, 7.62 / d, 7.55 / d, 7.45 / 7.58 / m, 7.50 / d, 7.20 / m, 6.75 / d, 6.63 / d) 6H (1.72 / s)

LC / MS: m / z = 602 [(M + 1) ^&lt; ^{+ &}

Synthetic example  3: Compound 52 Synthesis

(One) Manufacturing example  1: Synthesis of Intermediate 52-1

Sodium tert-butoxide (8.25 g, 0.086 mol, Sigma aldrich), 4-aminobiphenyl (8.71 g, 0.0515 mol, Sigma aldrich), Catalyst Pd (dba) ₂ (10 g, 0.043 mol, Sigma aldrich) 150 mL of Toluene was added to 1.23 g, 0.002 mol, sigma aldrich) and tri-tert-Bu-phosphine (0.87 g, 0.004 mol, Sigma aldrich) and reacted at 100 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was poured into H ₂ O, layered, and subjected to column purification (N-HEXANE: MC) to obtain 11.5 g (yield: 83.4%) of Intermediate 52-1.

(2) Manufacturing example  2: Synthesis of Compound 52

Intermediate 52-1 (14.4 g, 0.045 mol), cesuim carbonate (14.57 g, 0.045 mol, sigma aldrich), catalyst Pd (OAc) ₂ (0.47 g, 0.0021 mol, Sigma Aldrich), xant-phos (2.07 g, 0.0036 mol, Sigma Aldrich) and 150 mL of Toluene were added and reacted at 100 ° C for 4 hours with stirring. After completion of the reaction, the mixture was subjected to column separation with H ₂ O: MC and then subjected to column purification (N-HEXANE: EA) to obtain 14.3 g (yield 75%) of Compound 24.

M, 7.50 / m, 6.75 / d) 2H (7.58 / m, 7.50 / d) 3H (7.41 / m) 4H (7.54 / d, 6.69 / d) 6H (7.52 /

LC / MS: m / z = 638 [(M + 1) ^&lt; ^{+ &}

Synthetic example  4: Compound 68 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 68-1

Sodium tert-butoxide (5.97 g, 0.062 mol, Sigma aldrich), catalyst Pd (dba, 0.037 mol, Sigma Aldrich), 3-Bromo-9-phenylcarbazole _{) 2 (0.89 g, 0.0016 mol} , sigma aldrich), tri-tert-Bu-phosphine (0.63 g, put on Toluene 150 mL 0.003 mol, sigma aldrich) it was reacted under stirring at 100 ℃ for 5 hours. 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 10.3 g (yield 80.8%) of Intermediate 68-1.

(2) Manufacturing example  2: Synthesis of Compound 68

Intermediate 4-5 (10 g, 0.021 mol) , intermediate 90-2 (13.2 g, 0.032 mol) , cesuim carbonate (10.46 g, 0.032 mol, sigma aldrich), catalyst _{Pd (OAc) 2 (0.34 g} , 0.0015 mol, Sigma Aldrich), xant-phos (1.49 g, 0.026 mol, Sigma Aldrich) and 150 mL of Toluene were added and reacted at 100 ° C for 6 hours with stirring. After completion of the reaction, the mixture was subjected to column separation with H ₂ O: MC and then subjected to column purification (N-HEXANE: EA) to obtain 12.4 g (yield: 79.6%) of Compound 68.

M, 7.43 / d, 7.43 / d, 7.44 / d, 7.44 / d, 7.38 / m, 7.25 / m, 6.75 / m, 6.69 / d) 4H (7.58 / m, 7.52 / d, 7.51 / m, 7.50 /

LC / MS: m / z = 727 [(M + 1) ^&lt; ^{+ &}

Synthetic example  5: Compound 90 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 90-1

Dibenzo [b, d] furan-4-ylboronic acid (10.78 g, 0.051 mol, Yurii), potassium carbonate (14.65 g, 0.106 mol, Sigma Aldrich), 1,4-dibromobenzene (10 g, 0.042 mol, Sigma Aldrich) , Pd (PPh ₃ ) ₄ (2.45 g, 0.0021 mol, Sigma aldrich), 150 mL of THF and 40 mL of H ₂ O were added and reacted by refluxing for 12 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 10.8 g (yield: 78.8%) of Intermediate 90-1.

(2) Manufacturing example  2: Synthesis of intermediate 90-2

Sodium tert-butoxide (5.95 g, 0.062 mol, sigma aldrich), Catalyst Pd (dba) ₂ (0.89 g, 0.015 mol) were added to a solution of intermediate 90-1 (10 g, 0.031 mol), 4-aminobiphenyl , 0.002 mol, Sigma aldrich) and tri-tert-Bu-phosphine (0.63 g, 0.003 mol, Sigma aldrich) were added and reacted at 100 ° C for 5 hours. 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 performed to obtain 10 g (yield 78.5%) of <Intermediate 90-2>.

(3) Manufacturing example  3: Synthesis of Compound 90

Intermediate 4-5 (10 g, 0.021 mol) , intermediate 90-2 (13.2 g, 0.032 mol) , cesuim carbonate (10.46 g, 0.032 mol, sigma aldrich), catalyst _{Pd (OAc) 2 (0.34 g} , 0.0015 mol, sigma aldrich), xant-phos (1.49 g, 0.026 mol, Sigma Aldrich) and 150 mL of Toluene were added and reacted at 100 ° C for 4 hours with stirring. After completion of the reaction, the reaction mixture was subjected to column separation with H ₂ O: MC, followed by column purification (N-HEXANE: EA) to obtain 12.1 g (yield: 77.6%) of Compound 90.

D, 7.89 / d, 7.85 / d, 7.81 / d, 7.66 / d, 7.45 / m, 7.33 / m, 7.52 / d, 7.51 / m, 6.69 / d). [0050]

LC / MS: m / z = 728 [(M + 1) ^&lt; ^{+ &}

Synthetic example  6: Synthesis of Compound 140

(One) Manufacturing example  1: Synthesis of intermediate 140-1

1-iodo-2-nitrobenzene (12.70 g, 0.051 mol, Sigma aldrich), potassium carbonate (11.75 g, 0.085 mol, Sigma aldrich), 3-bromo-4-chlorophenylboronic acid (10 g, 0.043 mol, 150 mL of THF and 40 mL of water were added to Pd (PPh ₃ ) ₄ (2.46 g, 0.0021 mol, sigma aldrich), and the mixture was reacted at 60 ° C for 12 hours with stirring. 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 11 g (yield: 82.8%) of Intermediate 140-1.

(2) Manufacturing example  2: Synthesis of intermediate 140-2

250 mL of the intermediate 140-1 (10 g, 0.032 mol), triphenylphosphine (25.18 g, 0.096 mol, sigma aldrich) and 1,2-dichlorobenzene was added and reacted at 180 ° C for 12 hours with stirring. After completion of the reaction, the reaction mixture was subjected to column separation with H ₂ O: MC and then subjected to column purification (N-HEXANE) to obtain 7.2 g (yield 80%) of Intermediate 140-2.

(3) Manufacturing example  3: Synthesis of intermediate 140-3

Iodobenzene (9.5 g, 0.046 mol, Sigma Aldrich), potassium carbonate (14.78 g, 0.1069 mol, SigmaAldrich), Cu (4.53 g, 0.071 mol, Sigma Aldrich), dibenzo -18-crown-6 (1.28 g, 0.004 mol, Sigma Aldrich) and 150 mL of dimethylformamide, and the mixture was reacted at 150 ° C for 12 hours. After completion of the reaction, the reaction mixture was subjected to layer separation on H 2 O: MC and column purification (N-HEXANE: EA) yielded 10 g (yield 78.7%) of Intermediate 140-3.

(4) Manufacturing example  4: Synthesis of intermediate 140-4

Intermediate 140-3 (10 g, 0.028 mol) , 4- (Diphenylamino) phenylboronic acid (9.73 g, 0.034 mol, sigma aldrich), potassium carbonate (7.75 g, 0.056 mol, sigma aldrich), Pd (PPh 3) 4 ( 1.62 g, 0.0014 mol, sigma aldrich), 200 mL of Toluene, 40 mL of EtOH and 20 mL of H ₂ O were added and reacted by refluxing for 5 hours. After completion of the reaction, layer separation was performed using H ₂ O: EA and column purification (N-HEXANE: EA) was conducted to obtain 11.4 g (yield 78%) of Intermediate 140-4.

(5) Manufacturing example  5: Synthesis of Compound 140

Pd (PPh3) 4 (1.11g, 0.001mol, Sigma Aldrich), potassium carbonate (5.30g, 0.038mol, Sigma Aldrich), phenylboronic acid (2.81g, 0.023mol, sigma aldrich), 150 mL of Toluene, 30 mL of EtOH and 15 mL of H ₂ O were added, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, the reaction mixture was subjected to layer separation using H ₂ O: EA and then subjected to column purification (N-HEXANE: EA) to obtain 8.5 g (yield 78.7%) of Compound 140.

(7.79 / d, 7.85 / d, 7.45 / m, 7.41 / m, 7.33 / m, 7.25 / m) d, 7.58 / m, 7.54 / d, 7.51 / m, 7.50 / d, 6.81 /

LC / MS: m / z = 562 [(M + 1) ^&lt; ^{+ &}

Synthetic example  7: Compound 164 Synthesis

(One) Manufacturing example  1: Synthesis of intermediate 164-1

4,6-dibromodibenzofuran (20 g, 0.061 mol, Yurui), phenylboronic acid (8.98 g, 0.074 mol, sigma aldrich), potassium carbonate (16.96 g, 0.123 mol, sigma aldrich), Pd (PPh 3) 4 (3.54 g , 0.0031 mol, Sigma aldrich), 250 mL of THF and 50 mL of H ₂ O were added, 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 then subjected to column purification (N-HEXANE: MC) to obtain 14.3 g (yield: 72%) of Intermediate 164-1.

(2) Manufacturing example  2: Synthesis of intermediate 164-2

Potassium acetate (6.07 g, 0.062 mol, SigmaAldrich), PdCl ₂ (dppf) (0.68 g, 0.040 mol), bis (pinacolato) dibron (10.21 g, 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 and the mixture was subjected to column separation (N-HEXANE: MC) to obtain 8.2 g (yield: 72%) of Intermediate 164-2.

(3) Manufacturing example  3: Synthesis of intermediate 164-3

(15.71 g, 0.042 mol, Sigma aldrich), potassium carbonate (9.77 g, 0.071 mol, Sigma aldrich), Pd (PPh ₃ ), 1-bromo-4-iodobenzene ) ₄ (2.04 g, 0.0018 mol, Sigma aldrich), 150 mL of THF and 40 mL of H ₂ O were added, 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 then subjected to column purification (N-HEXANE: MC) to obtain 11.6 g (yield: 82%) of Intermediate 164-3.

(4) Manufacturing example  4: Synthesis of intermediate 164-4

Sodium tert-butoxide (4.81 g, 0.050 mol, sigma aldrich), Catalyst Pd (dba) ₂ (0.72 g, 0.03 mol) were added to a solution of intermediate 164-3 (10 g, 0.025 mol), 4-aminobiphenyl , 0.0013 mol, Sigma aldrich) and tri-tert-Bu-phosphine (0.51 g, 0.0025 mol, Sigma aldrich) were added 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: MC) to obtain 8.1 g (yield 78.6%) of Intermediate 164-4.

(5) Manufacturing example  5: Synthesis of intermediate 164-5

Sodium tert-butoxide (9.57 g, 0.0997 mol, Sigma aldrich), Catalyst Pd (dba), 4-bromophenylboronic acid (10 g, 0.05 mol, Sigma aldrich), Intermediate 164-4 (24.59 g, 0.06 mol, _{2 (1.43 g, 0.0025 mol,} sigma aldrich), tri-tert-Bu-phosphine into a 150 mL Toluene in (1.01 g, 0.005 mol, sigma aldrich) was reacted under stirring at 100 ℃ for 4 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 20.7 g (yield: 78.2%) of Intermediate 164-5.

(6) Manufacturing example  6: Synthesis of intermediate 164-6

Intermediate 140-3 (10 g, 0.028 mol) , intermediate 164-5 (17.88 g, 0.034 mol, sigma aldrich), potassium carbonate (7.75 g, 0.056 mol, sigma aldrich), Pd (PPh 3) 4 (1.62 g, 0.0014 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 7 hours. After completion of the reaction, the reaction mixture was subjected to layer separation using H ₂ O: EA and then subjected to column purification (N-HEXANE: EA) to obtain 18 g (yield 79.5%) of Intermediate 164-6.

(7) Manufacturing example  7: Synthesis of compound 164

Intermediate 164-6 (10 g, 0.012 mol) , phenylboronic acid (1.81 g, 0.015 mol, sigma aldrich), potassium carbonate (3.42 g, 0.0248 mol, sigma aldrich), Pd (PPh 3) 4 (0.72 g, 0.0006 mol , sigma aldrich), 150 mL of Toluene, 30 mL of EtOH, and 15 mL of H ₂ O were added, and the mixture was stirred under reflux for 8 hours. After completion of the reaction, the reaction mixture was subjected to layer separation using H ₂ O: EA and then subjected to column purification (N-HEXANE: EA) to obtain 7.7 g (yield 77.3%) of Compound 164.

7.81 / d, 7.79 / d, 7.45 / m, 7.33 / m, 7.25 / m, 6.81 / d, 7.58 / m, 7.52 / d, 7.50 / d, 7.41 / m, 7.38 / m, 7.20 / m, 6.63 / d)

LC / MS: m / z = 804 [(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 17

A blue light emitting organic electroluminescent device having the following device structure was prepared by using the compound implemented 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 injecting layer on the ITO transparent electrode, a hole injecting layer was formed by a vacuum thermal evaporation method with a thickness of 5 nm by using [HAT_CN], and then the hole transporting layer was formed by using α-NPB. The electron blocking layer may be formed using a composition of the present invention having a thickness of 10 nm using the chemical formulas 4, 24, 40, 52, 68, 81, 90, 105, 118, 126, 129, 132, 140, 152, 164, 175, Thick. Further, an electron transport layer (doped with Liq 50% of the following compound [201]) was further formed in 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 vapor deposition to produce an organic electroluminescent device.

Device Comparative Example 1

The organic electroluminescent device for Device Comparison Example 1 was fabricated in the same manner as in Example 1, except that TCTA was used instead of the chemical formula 12 according to the present invention as the electron blocking layer material in the device structure of Example 1 above.

EXPERIMENTAL EXAMPLE 1: Luminescent characteristics of element embodiments 1 to 17

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 Host V cd / A QE (%) CIEx CIEy One Formula 4 4.05 8.25 6.97 0.143 0.153 2 24 4.20 8.10 6.80 0.145 0.155 3 40 4.22 8.14 6.83 0.145 0.154 4 Formula 52 4.15 8.20 6.88 0.144 0.155 5 68 4.09 8.22 6.90 0.144 0.153 6 81 4.20 8.12 6.80 0.145 0.156 7 90 4.19 8.20 6.84 0.144 0.152 8 105 4.17 8.12 6.81 0.144 0.154 9 Formula 118 4.25 8.01 6.68 0.145 0.154 10 126 4.20 8.05 6.73 0.145 0.155 11 129 4.22 8.09 6.80 0.145 0.155 12 Formula 132 4.13 8.17 6.86 0.144 0.154 13 140 4.16 8.14 6.82 0.145 0.155 14 Formula 152 4.11 8.18 6.88 0.144 0.154 15 (164) 4.18 8.16 6.85 0.145 0.154 16 Formula 175 4.17 8.09 6.80 0.145 0.155 17 180 4.21 8.10 6.80 0.145 0.156 Comparative Example 1 TCTA 4.14 6.40 5.10 0.145 0.155

When the compounds according to the present invention were employed in the electron blocking layer of the device, the light emitting properties such as luminous efficiency and quantum efficiency were remarkably superior to those of the conventional device (Comparative Example 1, TCTA) can confirm.

[HAT_CN] [? -NPB] [BH1] [BD1] [201] [TCTA]

Claims (6)

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

In the above formula (I)
R ₁ to R ₃ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted C6- A substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted diarylamino group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroarylamino group having 5 to 40 carbon atoms,
At least one of R ₁ to R ₃ is represented by the following formula 1,
[Structural formula 1]

In the structural 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; The method according to claim 1,
When R ₁ to R ₃ are not each the above-mentioned [structural formula 1], they are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms Organic luminescent compound. 3. The method according to claim 1 or 2,
In the definition of R ₁ to R ₃ , L and Ar ₁ to Ar ₂ , the substitution or unsubstitution means that R ₁ to R ₃ , L and Ar ₁ to Ar ₂ are deuterium, a cyano group, a 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 6 to 24 carbon atoms, A heteroarylamino group having 5 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, and an aryloxy group having 6 to 24 carbon atoms, and one or two or more substituents 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. 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 (192)

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. 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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