KR100846221B1 - Light-emitting compound and organic light-emitting diodes using the same - Google Patents

Abstract

An organic light emitting compound is provided to ensure excellent electrical characteristics and electroluminescent characteristics, and to be useful as a host material of a light emitting layer or a material for forming a hole transport layer or electron block layer. An organic light emitting compound has a structure represented by the following formula 1, wherein Y is carbon or silicon, X1 and X2 are a divalent linker, are identical to or different from each other, and are C6-18 substituted or unsubstituted arylene, or C4-18 substituted or unsubstituted heteroarylene, R1 and R2 are identical to or different from each other and are hydrogen, C1-8 substituted or unsubstituted alkyl groups, C6-24 substituted or unsubstituted aryl groups, or C4-24 substituted or unsubstituted heteroaryl groups, with the proviso that both R1 and R2 are not hydrogen, Ar1, Ar2, Ar3, and Ar4 are identical to or different from one another and are C6-24 substituted or unsubstituted aryl groups or C4-24 substituted or unsubstituted heteroaryl groups, and at least one of R1 and R2, R1 and X1, R1 and X2, or X1 and Ar1 is linked with each other to form a fused ring.

Description

Organic light-emitting compounds and organic light-emitting diodes using the same

1 is a view schematically showing the structure of an organic EL device according to an embodiment of the present invention.

2 is a graph showing the spectra of the organic electroluminescent devices fabricated in Example 9 and Comparative Example 1. FIG.

3 is a graph showing the luminance of the organic EL device manufactured in Example 9 and Comparative Example 1 according to the current density.

4 is a graph showing the spectrum of the organic electroluminescent device manufactured in Example 10 and Comparative Example 2.

5 is a graph showing the luminance of the organic light emitting diodes manufactured in Example 10 and Comparative Example 2 according to current density.

The present invention relates to an organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to an organic light emitting compound useful as a host material, a hole transport layer and / or an electron blocking layer forming material of the light emitting layer and an organic electroluminescent device using the same. It is about.

To date, most of the flat panel displays are liquid crystal displays, but efforts are being made to develop new flat panel displays that are more economical and superior in performance and differentiated from liquid crystal displays. Recently, the organic EL device, which has been spotlighted as a next-generation flat panel display, has advantages such as low driving voltage, fast response speed, and wide viewing angle, compared to a liquid crystal display.

On the other hand, the research on the electroluminescent device using the organic material has been focused and reviewed for a long time, but the luminous efficiency is low, it has not been put to practical use. Organic electroluminescent device is based on the principle that electrons and holes injected through the cathode and anode form excitons in the organic thin film made of monomolecule or polymer, and light of specific wavelength is generated from the formed excitons. The back was first discovered from a single crystal of anthracene. Kodak's Tang in 1987 proposed an organic electroluminescent device having a laminated structure of a functional separation type in which organic materials were divided into two layers, a hole transport layer and a light emitting layer. It was confirmed that high luminescence brightness was obtained (Tang, CW; Van Slyke, SA Appl. Phys. Lett. 1987, 51, 913.). Since then, the organic electroluminescent device has suddenly started to attract attention, and research on an organic electroluminescent device having a laminated structure of the same function separation type has been actively conducted.

The structure of a general organic electroluminescent device is a substrate, an anode, a hole injection layer for receiving holes in the anode, a hole transport layer for transporting holes, an electron blocking layer for preventing the entry of electrons from the light emitting layer to the hole transport layer, by combining the holes and electrons It consists of a light emitting layer that emits light, a hole blocking layer that blocks holes from entering the electron transport layer, an electron transport layer that accepts electrons from the cathode and transports them to the light emitting layer, an electron injection layer that accepts electrons from the cathode, and a cathode. In some cases, a light emitting layer may be formed by doping a small amount of fluorescent or phosphorescent dye into an electron transport layer or a hole transport layer without a separate light emitting layer.In the case of using a polymer, a single polymer generally includes a hole transport layer, a light emitting layer, and an electron transport layer. You can play a role at the same time. The organic thin film layers between the two electrodes are formed by vacuum deposition or spin coating, inkjet printing, laser thermal transfer, or the like. The reason why the organic electroluminescent device is manufactured in a multilayer thin film structure is to stabilize the interface between the electrode and the organic material. Also, in the case of the organic material, the hole and electron transport layer have a large difference in the movement speed of the hole. This is because luminous efficiency can be increased by effectively transferring electrons and electrons to the light emitting layer to balance the density of holes and electrons.

The driving principle of the organic EL device is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode are moved to the light emitting layer via the hole injection layer and the hole transport layer. On the other hand, electrons are injected into the light emitting layer from the cathode via the electron injection layer and the electron transport layer, and carriers are recombined in the light emitting layer to generate excitons. The excitons change from the excited state to the ground state, whereby the fluorescent molecules in the light emitting layer emit light to form an image. At this time, the excitation state is emitted to fall to the ground state through the singlet excited state is called "fluorescence", and the emission to fall to the ground state through the triplet excited state is called "phosphorescence". In the case of fluorescence, the probability of singlet excited state is 25% (triple state 75%), and there is a limit of luminous efficiency. Theoretically, the internal quantum efficiency can be up to 100%.

An organic light-emitting device using phosphorescence, which effectively emits light even in the triplet state (phosphorescence) using Ir (ppy) ₃ and PtOEP, which are phosphorescent pigments having heavy elements such as Ir and Pt having a large spin-orbit coupling force, as a dopant. The organic electroluminescent element with high efficiency of blue, green, and red was developed by carrying out. At this time, CBP (4,4'-N, N'-dicarbazole-biphenyl) was used as a host material. However, the organic electroluminescent device is insufficient in terms of commercial use because of its short lifespan of less than 150 hours. The reason is that the glass transition temperature of CBP is lower than 110 ° C and crystallization easily occurs.

In addition, as another example of an organic EL device using phosphorescence, an organic light emitting device employing a blue phosphorescent dopant (4,6-F2ppy) 2Irpic and an Ir compound based on a fluorinated ppy ligand structure has been developed. (METhompson, ACS Aug., 18, 2002 and Chem. Commun., 2001 1494-1495). In such organic electroluminescent devices, the energy gap of the triplet state of CBP allows sufficient energy transfer with respect to the energy gaps of green and red phosphorescent dopant materials. However, since the energy gap is smaller than the energy gap of the blue material, an exothermic energy transition is not found in a material such as (4,6-F2ppy) 2Irpic, which is a material for skyblue having PL peaks at 475 nm and 495 nm. A very inefficient endothermic transition has been reported. As a result, the CBP host does not provide sufficient energy transfer to the blue phosphorescent dopant, which is pointed out as a cause of problems of low blue light emission efficiency and short lifetime. In addition, US Patent Publication 2002/0125818 A1 discloses an organic EL device using a CBP compound. Recently, mCP (1,3-Bis (carbazol-9-yl) -benzene) compound having a triplet energy gap larger than CBP has been used, but this compound has problems such as low molecular weight and poor stability. Therefore, it is very important and urgent to secure an efficient and stable host material as a host for the blue dopant.

Accordingly, an object of the present invention is to provide an organic light emitting material which is useful as a host material of the light emitting layer because of its excellent electrical and light emitting properties, and in some cases also useful as a hole transport layer or an electron blocking layer forming material.

Still another object of the present invention is to provide an organic electroluminescent device having excellent luminous efficiency and current efficiency by employing the organic light emitting material.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1):

[Formula 1]

here,

Y is carbon or silicon;

X ₁ and X ₂ are divalent linking groups, which may be the same or different, substituted or unsubstituted arylene of C6 to C18, or substituted or unsubstituted divalent heteroarylene of C4 to C18;

R ₁ And R ₂ , which may be the same or different, is hydrogen or a substituted or unsubstituted alkyl group of C1 to C8, a substituted or unsubstituted aryl group of C6 to C24, a substituted or unsubstituted heteroaryl group of C4 to C24 ( Provided that R ₁ and R ₂ are not simultaneously hydrogen);

Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ , which may be the same or different, are a substituted or unsubstituted aryl group of C6 to C24, a substituted or unsubstituted heteroaryl group of C4 to C24;

_One or more of R ₁ and R ₂ , R ₁ and X ₁ , R ₁ and X ₂ , or X ₁ and Ar ₁ may be connected to each other to form a fused ring.

According to one embodiment of the present invention, at least one or more of the hydrogen atoms of R ₁ , R ₂ , Ar ₁ , Ar ₂ , Ar ₃ , or Ar _{4 described} above may be substituted by the following substituents:

,

,

또는

.

,

,

or

.

In order to achieve the above another object, the present invention is a first electrode; Second electrode; And an organic electroluminescent device comprising an organic layer interposed between the first electrode and the second electrode, the organic layer provides an organic electroluminescent device comprising the compound according to the invention described above.

The compound represented by Formula 1 according to the present invention is useful as a host material or an electron blocking layer forming material of the light emitting layer of the organic electroluminescent device. The organic electroluminescent device of the present invention comprising such a compound in a light emitting layer or an electron blocking layer provides excellent light emission efficiency and current efficiency.

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

The organic light emitting compound according to the present invention is a compound having an aryl phosphine oxide group and an aryl amine group at the same time. An aryl phosphine oxide group is a functional group excellent in the electron transport ability, and an aryl amine group is a functional group excellent in the hole transport ability. In the compound according to the present invention, the aryl phosphine oxide group and the aryl amine group are connected by Y in a non-conjugated state. Accordingly, the compound can be provided in which the respective functional group properties are maintained independently with the influence between the aryl phosphine oxide group and the aryl amine group minimized. This means that in the organic electroluminescent device, heat resistance to Joule heat generated between the organic layer and the organic layer and between the organic layer and the electrode and the resistance at high temperature can be increased. The organic light emitting compound according to the present invention may be used as a host material and an electron blocking layer material hole transport layer material of the light emitting layer, thereby providing an organic EL device having improved light emission efficiency.

As such, the present invention may be represented by the following Chemical Formula 1:

[Formula 1]

,

,

here,

Y is carbon or silicon;

X ₁ and X ₂ are divalent linking groups, which may be the same or different, substituted or unsubstituted arylene of C6 to C18, or substituted or unsubstituted heteroarylene of C4 to C18;

R ₁ And R ₂ , which may be the same or different, is hydrogen or a substituted or unsubstituted alkyl group of C1 to C8, a substituted or unsubstituted aryl group of C6 to C24, a substituted or unsubstituted heteroaryl group of C4 to C24 ( Provided that R ₁ and R ₂ are not simultaneously hydrogen);

Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ , which may be the same or different, are a substituted or unsubstituted aryl group of C6 to C24, a substituted or unsubstituted heteroallyl group of C4 to C24;

_One or more of R ₁ and R ₂ , R ₁ and X ₁ , R ₁ and X ₂ , or X ₁ and Ar ₁ may be connected to each other to form a fused ring.

Meanwhile, in the compound represented by Formula 1, X ₁ , X _{2 ,} R _{1 ,} R ₂ And Ar ₁ to Ar ₄ may include appropriate substituents to provide an organic light emitting compound having properties such as light emission efficiency, electrical properties and melting point, depending on the specific compound. Suitable substituents include, for example, halogen groups such as fluorine groups; C1 to C6 alkyl groups such as methyl group, isopentyl group, t-butyl group and the like; C1 to C6 alkoxy groups such as methoxy group, ethoxy group, isopentoxy group and the like; Cyano group; Including, but not limited to.

In Formula 1, X ₁ and X ₂ are divalent linking groups selected from the group consisting of phenylene, biphenylene, furanylene, thiophenylene, pyridinylene, pyrrolylene and fluorenylene. At least one substituent selected from the group consisting of a methyl group, a methoxy group, a t-butyl group, a fluorine group, and a trifluoromethyl group so as to provide an organic light emitting compound having desirable luminous efficiency and physical properties according to a specific compound. May be further substituted.

In Formula 1, R ₁ and R ₂ are a phenyl group, α-naphthyl group, β-naphthyl group, biphenyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-phenanthrenyl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 4-phenanthrenyl group, 9-phenanthrenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9- -Fluorenyl group, 2-thiophenyl group, 3-thiophenyl group, 2-pyridinyl group, 3-pyridinyl group, 2-pyrrolyl group, 3-pyrrolyl group, 2-furanyl group, 3-furanyl group 4-methylphenyl Group, 4-fluorophenyl group, 4-nitrophenyl group, 4-methylphenyl group, methyl group, ethyl group, 1-propyl group 2-propyl group, 1-butyl group, 2-butyl group, t-butyl group, 1-pentyl group, 2-pentyl group, 3-pentyl group, neopentyl group cyclohexyl group, n-hexyl group and nonyl group can be selected.

In Formula 1, Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are a phenyl group, α-naphthyl group, β-naphthyl group, biphenyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group , 1-phenanthrenyl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 4-phenanthrenyl group, 9-phenanthrenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4 -Fluorenyl group, 9-fluorenyl group, 2-thiophenyl group, 3-thiophenyl group, 2-pyridinyl group, 3-pyridinyl group, 2-pyrrolyl group, 3-pyrrolyl group, 2-furanyl group, 3- Furanyl group 4-methylphenyl group, 4-fluorophenyl group, 4-nitrophenyl group, and 4-methylphenyl group.

In addition, R ₁ , R ₂ , Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ At least one of the hydrogen atoms may be substituted with the following substituents to provide an organic electroluminescent device exhibiting an appropriate wavelength and having improved luminous efficiency:

,

,

또는

.

,

,

or

.

Examples of the compound represented by Formula 1 include a compound represented by the following formula:

,

,

,

,

,

,

[Formula 1-1] [Formula 1-2] [Formula 1-3]

,

,

,

,

,

,

[Formula 1-4] [Formula 1-5] [Formula 1-6]

,

,

,

,

,

,

[Formula 1-7] [Formula 1-8] [Formula 1-9]

,

,

,

,

,

,

[Formula 1-10] [Formula 1-11] [Formula 1-12]

,

,

,

,

,

,

[Formula 1-13] [Formula 1-14] [Formula 1-15]

,

,

,

,

,

,

[Formula 1-16] [Formula 1-17] [Formula 1-18]

,

,

,

,

,

,

[Formula 1-19] [Formula 1-20] [Formula 1-21]

,

,

,,

,

,

,

[Formula 1-22] [Formula 1-23] [Formula 1-24]

,

,

,

,

,

,

[Formula 1-25] [Formula 1-26] [Formula 1-27]

,

,

,

,

,

,

[Formula 1-28] [Formula 1-29] [Formula 1-30]

또는

.

or

.

[Formula 1-31] [Formula 1-32]

Compound represented by Formula 1 can be obtained through the following schemes 1 and 2:

Scheme 1

Scheme 2

Scheme 1 is a process of obtaining a tertiary alcohol through lithium lithiation of a phosphine compound using basic n-butyl lithium and a condensation reaction of the lithium-substituted phosphine compound with a ketone compound. In addition, Scheme 2 is a process of replacing the alcohol with an aryl amine group through the SN1 reaction by an acid catalyst, as a result of obtaining a compound of formula (1) according to the present invention. As the acid catalyst, sulfonic acids such as methanesulfonic acid and ethanesulfonic acid may be used. It is a matter of course that the compound of formula 1 can be obtained by appropriately modifying the reaction scheme.

Hereinafter, an organic electroluminescent device using the organic light emitting compound according to the present invention will be described.

The organic EL device according to the present invention can be realized in various structures. Referring to FIG. 1, in the organic electroluminescent device 100 according to an embodiment of the present invention, the light emitting layer 6 is inserted between the anode 2 and the cathode 10 on the transparent substrate 1. If necessary, one or more layers of the hole injection layer 3, the hole transport layer 4, or the electron blocking layer 5 may be inserted between the anode 2 and the light emitting layer 6, and the cathode 10 and the light emitting layer ( 6) one or more layers of the hole blocking layer 7, the electron transport layer 8, or the electron injection layer 9 may be interposed therebetween. However, the structure of the organic EL device according to the present invention is not limited thereto, and one layer may be formed of the emission layer and the electron transport layer.

The anode 2 of the organic electroluminescent device of the present invention may be formed using a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of about 4 eV or more. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO ₂ and ZnO which are metals are mentioned. The thickness of the anode layer may be about 10 to 200 nm.

The cathode 10 of the organic electroluminescent device of the present invention may be formed using a metal, alloy, electroconductive compound or mixtures thereof having a work function of less than about 4 eV. Specific examples include aluminum, Na, Na-K alloys, calcium, magnesium, lithium, lithium alloys, indium, aluminum, magnesium alloys, and aluminum alloys. In addition, aluminum / AlO ₂ , aluminum / lithium, magnesium / silver or magnesium / indium may be used. Among these, aluminum (Al) which is excellent in stability especially can be used as a cathode. The thickness of the cathode layer may be about 10 to 200 nm.

In order to increase the luminous efficiency of the organic electroluminescent device, at least one electrode should preferably have a light transmittance of 10% or more. The sheet resistance of the electrode should preferably be several hundreds of mm 3 / mm or less. The thickness of the electrode is 10 nm to 1 탆, preferably 10 to 400 nm. Such an electrode may be manufactured by forming the above electrode material into a thin film through vapor deposition or sputtering such as chemical vapor deposition (CVD), physical vapor deposition (PVD), or the like.

The hole transport layer 4 may be formed using the compound of Formula 1 according to the present invention. It can be formed by selecting arbitrarily from known materials used. For example, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'-diaminobiphenyl (hereinafter referred to as TPD), N, N'-bis (1- Naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine (hereinafter referred to as NPD), N, N'-diphenyl-N, N'-dinaphthyl -4,4'-diaminobiphenyl, N, N, N'N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N, N, N'N'-tetraphenyl-4, 4'-diaminobiphenyl; Porphyrin compound derivatives such as Copper (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin and the like; Polymers having aromatic tertiary amines in the main or side chain, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N, N-tri (p-tolyl) amine, 4 ', 4' Triarylamine derivatives such as 4'-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine; Carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole; Phthalocyanine derivatives such as metal phthalocyanine and copper phthalocyanine; Starburst amine derivatives; Enamine stilbene derivatives; Derivatives of aromatic tertiary amines and styryl amine compounds; And polysilanes.

The hole transport layer 4 may be formed of a single layer containing one or more kinds of the above-described compounds, or may be composed of a plurality of layers containing different kinds of compounds stacked on each other.

The electron blocking layer 5 may be formed using the organic light emitting compound according to the present invention.

 The light emitting layer 6 may be formed using the compound of Formula 1 according to the present invention as a host material, and may further include at least one of a phosphorescent host, a fluorescent host, or a dopant in the visible light region. It may also be formed using a known light emitting material, for example, a phosphorescent fluorescent material, a fluorescent brightener, a laser dye, an organic scintillator and a fluorescence reagent. Specific examples include polyaromatic compounds such as AlQ 3, anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone; Oligophenylene compounds such as quiterphenyl; 1,4-bis (2-methylstyryl) benzene, 1,4-bis (4-methylstyryl) benzene, 1,4-bis (4-methyl-5-phenyl-2-oxazolyl) benzene, 1 , 4-bis (5-phenyl-2-oxazolyl) benzene, 2,5-bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, Scintillators for liquid scintillation such as 1,6-diphenyl-1,3,5-hexatriene, 1,1,4,4-tetraphenyl-1,3-butadiene; Metal complexes of auxin derivatives; Coumarin pigments; Dicyano methylene pyran pigment; Dicyano methylenethiopyran pigments; Polymethine pigments; Oxobenzanthracene pigment; Xanthene pigments; Carbostyryl pigments; Perylene pigments; Oxazine compounds; Stilbene derivatives; Spiro compounds; And oxadiazole compounds. These may be used in combination with the compounds according to the present invention.

The hole blocking layer can also be formed using the allyl phosphine compound described in Applicant's patent application 2004-0054699.

The electron transport layer 8 is preferably a material having a high electron mobility that can receive electrons from the electron injection layer 11 and transfer the electrons to the light emitting layer. Specific examples of materials that may be used to form the electron transport layer 8 in the present invention include 8-hydroxyquinoline aluminum complex (AlQ3); Organic compounds including AlQ3 structures; Hydroxyflavone-metal complexes; And silacyclopentadiene (silole) compounds, but are not limited thereto. It may also be formed using the allyl phosphine compound described in Applicant's patent application 2005-0031628.

The electron injection layer 9 is, of course, formed as an aryl phosphine oxide compound represented by the above formula (1). The thickness of the electron injection layer 9 may be about 1 to 5 nm, preferably about 2 to 5 nm. If the thickness is less than about 1 nm, the film thickness is so thin that a uniform film is difficult to obtain, the electron injection performance is lowered, and the electron injection performance is similarly lowered even if the film thickness exceeds about 5 nm.

The organic electroluminescent device having the above structure is supported by the transparent substrate 1. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. For example, glass, a transparent plastic film, etc. can be used.

Each layer constituting the organic electroluminescent device of the present invention may be formed into a thin film through a known method such as vacuum deposition, spin coating or laser thermal transfer, or may be manufactured using materials used in each layer. There is no particular limitation on the film thickness of each layer, and may be appropriately selected depending on the properties of the material, but can usually be determined in the range of 2 to 5000 nm.

An organic electroluminescent device having an anode / hole transporting layer / light emitting layer / electron transporting layer / electron injection layer / cathode structure as an example of the method of manufacturing an organic electroluminescent device using the host material represented by Formula 1 of the present invention as a light emitting layer host material The explanation is as follows.

First, a hole transport layer is formed using a hole transport material on an ITO transparent substrate having a thickness of 1 μm or less, preferably 10 to 200 nm. Subsequently, the light emitting layer is formed to cover the hole transport layer by vacuum-depositing the compound of formula 1 according to the present invention with a fluorescent or phosphorescent dopant. Subsequently, an electron transport layer is formed on the emission layer by using the electron transport material. Subsequently, an electron injection layer is formed on this electron transport layer using an electron injection material. Finally, an organic electroluminescent device is obtained by coating the electron injection layer with a thin film containing a cathode material with a thickness of 1 μm or less to form a cathode. When the DC voltage is applied to the organic electroluminescent device obtained by using the anode as the positive electrode and the cathode as the negative electrode, light emission can be observed through the transparent or opaque electrode (either the anode or the cathode, or both electrodes). .

Hereinafter, a method of manufacturing an organic EL device having an organic light emitting compound and an emission layer or an electronic blocking layer formed using the same according to the present invention will be described in more detail. However, this is for illustrative purposes and the scope of the present invention is not limited thereby.

Example

Synthesis of Intermediates

Hereinafter, preparation examples for synthesizing the following intermediates 1 to 9 are described:

,

,

,

,

[Intermediate 1] [Intermediate 2] [Intermediate 3]

,

,

,

,

,

[Intermediate 4] [Intermediate 5] [Intermediate 6]

,

,

,

,

[Intermediate 7] [Intermediate 8] [Intermediate 9]

Production Example  1: Synthesis of Intermediate 1

1,4-dibromobenzene (23.6 g, 100 mmol) was dissolved in 300 ml of purified THF under nitrogen atmosphere and cooled to -78 ° C. 42 ml (105 mmol, 2.5 M hexane solution) of n-butyl lithium were slowly added to the reaction solution for 30 minutes. The reaction solution was further stirred at the same temperature for 1 hour, then chlorodiphenylphosphine (22 g, 100 mmol) was added slowly. After the cooling vessel was removed and stirred at room temperature for 3 hours, excess water was added to the reaction solution. The organic layer was then extracted using methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography gave 25 g of a compound of white solid intermediate 1 (yield 73.3%).

Production Example  2: synthesis of intermediate 2

3.1 g of the compound of Intermediate 2 was obtained as a white solid by the same method as Preparation Example 1, except that 4,4'-dibromobiphenyl was used instead of 1,4-dibromobenzene (yield 74.3%).

Production Example  3: synthesis of intermediate 3

In a nitrogen atmosphere, 10.2 g (30 mmol) of the compound of Intermediate 1 were dissolved in 200 mL of purified THF and cooled to -78 ° C. 14 ml (35 mmol, 2.5 M hexane solution) of n-butyl lithium was slowly added to the reaction solution for 30 minutes. After stirring for another hour at the same temperature, 9-fluorenone (5.4 g, 30 mmol) was added slowly. After removing the cooling vessel and stirred for 3 hours at room temperature, excess water was added to the reaction solution. The organic layer was extracted using methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography gave a white solid. The obtained white solid was dissolved in acetone, and excess hydrogen peroxide was added and stirred for about 10 minutes. The solvent was removed under reduced pressure to give 10.2 g of the compound of Intermediate 3 (yield 74.2%).

Production Example  4: Synthesis of Intermediate 4

9.3 g of a compound of the intermediate 4 was obtained as a white solid by the same method as Preparation Example 3, except that benzophenone was used instead of 9-fluorenone (yield 67.4%).

Production Example  5; Synthesis of Intermediate 5

3.3 g of a compound of the intermediate 5 was obtained as a white solid by the same method as Preparation Example 3, except that 4,4'-dimethylbenzophenone was used instead of 9-fluorenone (yield 67.3%).

Production Example  6: Synthesis of Intermediate 6

12.5 g (30 mmol) of the compound of Intermediate 2 were dissolved in purified THF (200 mL) under nitrogen atmosphere and cooled to -78 ° C. N-butyl lithium (14 mL, 35 mmol, 2.5 M hexane solution) was slowly added to the reaction solution for 30 minutes. After stirring for 1 hour at the same temperature, 9-fluorenone (5.4 g, 30 mmol) was added slowly. After removing the cooling vessel and stirred for 3 hours at room temperature, excess water was added to the reaction solution. The organic layer was extracted using methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. The crude product obtained was purified by column chromatography. After dissolving the obtained solid in acetone, an excess of hydrogen peroxide was added and stirred for about 10 minutes. The solvent was removed under reduced pressure to obtain 12.3 g of a compound of intermediate 6 as a white solid (yield 76.9%).

Production Example  7: Synthesis of Intermediate 7

In a nitrogen atmosphere, Compound 1-15 (2g, 3 mmol) and dimethylformamide (DMF) 30ml were added thereto, and then dissolved. The mixture was cooled to 0 ° C. POCl ₃ in the reaction solution It was slowly heated to 100 ° C. with 4.6 g (30 mmol) added. The reaction solution was stirred for 2 hours, the reaction degree was confirmed by thin layer chromatography, and excess water was added to precipitate a solid. The precipitated solid was filtered and further purified by column chromatography to obtain 1.3 g of a compound of intermediate 7 as a yellow solid (yield 60.7%). The results of NMR analysis are as follows:

NMR- ¹ H (400 MHz, CDCl ₃ ; ppm): δ = 6.96, 6.98, 7.00 (t, 4H), 7.09-7.14 (m, 5H), 7.7.29-7.31 (m, 5H), 7.38-7.47 ( m, 7H), 7.58-7.74 (m, 11H), 7.76-7.78 (d, 2H), 8.01 (s, 1H), 9.78 (s, 1H).

Production Example  8: Synthesis of Intermediate 8

In a nitrogen atmosphere, 8.4 g (25 mmol) of 1-bromo-4- (2,2-diphenylvinyl) benzene was dissolved in 200 ml of purified THF and cooled to -78 deg. To the reaction solution was added 9.6 mL (24 mmol, 2.5 M hexane solution) of n-butyl lithium slowly over 30 minutes. After stirring for another hour at the same temperature, 4-bromobenzophenone (6 g, 23 mmol) was added slowly. After removing the cooling vessel and stirred for 3 hours at room temperature, excess water was added to the reaction solution. The organic layer was extracted using methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography gave 9.8 g of compound 8 as a white solid (yield 82.3%).

Production Example  9: Synthesis of Intermediate 9

5 g (9.6 mmol) of the compound of Intermediate 8 and 5 g (20 mmol) of triphenylamine were dissolved in 50 ml of methylene chloride under a nitrogen atmosphere, and then cooled to 0 ° C. 1.0 g (10 mmol) of methane sulfonic acid was slowly added to the reaction solution, stirred at room temperature for 2 hours, and excess water was added to the reaction solution. The organic layer was extracted with methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography gave 6.5g of intermediate 9 as a white solid (yield 90.9%).

Hereinafter, examples for synthesizing the compounds according to the present invention will be described.

Example  1: Synthesis of Compound of Formula 1-1

In a nitrogen atmosphere, 2.3 g (5 mmol) of the compound of Intermediate 4 and 3.7 g (15 mmol) of triphenylamine were dissolved in 100 ml of methylene chloride, and then cooled to 0 ° C. 1.0 g (10 mmol) of methane sulfonic acid was slowly added to the reaction solution, stirred at room temperature for 2 hours, and excess water was added to the reaction solution. The organic layer was extracted with methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography gave 2.8 g of a white solid compound of the formula 1-1 (yield 81.4%).

NMR- ¹ H (400 MHz, CDCl ₃ ; ppm): δ = 6.88-6.70 (d, 2H), 6.96-7.00 (m, 4H), 7.03-7.05 (d, 4H), 7.19, 7.21, 7.23 (t, 4H), 7.27-7.31 (m, 4H), 7.34-7.43 (m, 10H), 7.48-7.50 (m, 4H), 7.61-7.62 (m, 4H), 7.74-7.72 (d, 2H).

Example  2: Synthesis of Compound of Formula 1-10

In a nitrogen atmosphere, 2.4 g (5 mmol) of the compound of Intermediate 5 and 3.7 g (15 mmol) of triphenylamine were dissolved in 100 ml of methylene chloride, and then cooled to 0 ° C. Methanesulfonic acid (1.0 g, 10 mmol) was slowly added to the reaction solution, stirred at room temperature for 2 hours, and excess water was added. The organic layer was extracted with methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography gave 2.1g of the compound of Formula 1-10 as a white solid (yield 58.6%).

NMR- ¹ H (400 MHz, DMSO-d ₆ ; ppm): δ = 2.25 (s, 6H), 6.86-6.88 (d, 1H), 6.99-7.05 (m, 13H), 7.09-7.71, (d, 4H ), 7.27-7.74 (m, 6H), 7.51-7.57 (m, 6H), 7.60-7.75 (m, 6H).

Example  3: Synthesis of Compound of Formula 1-14

In a nitrogen atmosphere, 2.7 g (6 mmol) of the compound of formula 3 and 5.0 g (20 mmol) of triphenylamine were dissolved in 100 ml of methylene chloride, and the reaction solution was cooled to 0 ° C. Methanesulfonic acid 1.5g (16 mmol) was slowly added to the reaction solution, stirred at room temperature for 2 hours, and excess water was added. The organic layer was extracted with methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography gave 3.2 g of the compound of Formula 1-14 as a white solid (yield 78%).

NMR- ¹ H (400 MHz, DMSO-d ₆ ; ppm): δ = 6.84-6.68 (d, 2H), 6.95-6.97 (d, 4H), 6.99-7.04 (m, 4H), 7.24-7.74 (m, 8H), 7.39, 7.41, 7.43 (t, 2H), 7.46-7.48 (d, 2H), 7.49-7.54 (d, 6H), 7.56-7.61 (m, 6H), 7.92-7.74 (d, 2H).

Example  4: Synthesis of Compound of Formula 1-15

In a nitrogen atmosphere, 2.7 g (6 mmol) of the compound of formula 3 and 5.0 g (20 mmol) of 9-phenylcarbazole were dissolved in 100 ml of methylene chloride and cooled to 0 ° C. 1.5 g (16 mmol) of methanesulfonic acid was slowly added to the reaction solution, stirred at room temperature for 2 hours, and excess water was added thereto. The organic layer was extracted with methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography afforded 3 g of a compound of formula 1-15 as a white solid (yield 73%).

NMR- ¹ H (400 MHz, CDCl ₃ ; ppm): δ = 7.19-7.21 (m, 1H), 7.23-7.29 (m, 4H), 7.33-7.74 (m, 2H), 7.46-7.50 (m, 6H) , 7.53 to 7.74 (m, 3H), 7.63 to 7.08 (m, 4H), 7.78 to 7.79 (d, 2H), 7.85 to 7.86 (d, 1H), 7.93 to 7.95 (d, 1H).

Example  5: Synthesis of Compound of Formula 1-19

In a nitrogen atmosphere, 2.7 g (6 mmol) of the compound of Intermediate 6 and 5.0 g (20 mmol) of triphenylamine were dissolved in 100 ml of methylene chloride and cooled to 0 ° C. 1.5 g (16 mmol) of methanesulfonic acid was slowly added to the reaction solution, stirred at room temperature for 2 hours, and excess water was added thereto. The organic layer was extracted with methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed. Purification by column chromatography gave 3.4 g of a compound of the formula 1-19 as a white solid (yield 74.4%).

NMR- ¹ H (400 MHz, DMSO-d ₆ ; ppm): δ = 6.86-6.88 (d, 2H), 6.95-6.97 (d, 4H), 6.98, 7.00, 7.02 (t, 2H), 7.06-7.09 ( d, 2H), 7.20 ~ 7.22 (d, 2H), 7.24, 7.26, 7.28 (t, 4H), 7.30, 7.32, 7.34 (t, 2H), 7.38, 7.40, 7.42 (t, 2H), 7.47 ~ 7.49 (d, 2H), 7.52-7.56 (m, 4H), 7.58-7.72 (m, 10H), 7.74-7.72 (m, 2H), 7.92-7.74 (d, 2H).

Example  6: Synthesis of Compound of Formula 1-16

0.56 g (1.2 mmol) of the compound of Intermediate 3 and 1.3 g (5 mmol) of 4-methyltriphenylamine were dissolved in 10 ml of methylene chloride and cooled to 0 ° C. under a nitrogen atmosphere. 0.24 g (2.5 mmol) of methanesulfonic acid was slowly added to the reaction solution, stirred at room temperature for 2 hours, and excess water was added thereto. The organic layer was extracted with methylene chloride and water was removed with anhydrous magnesium sulfate to obtain 0.3 g of the compound of Formula 1-16 (yield 50%).

NMR- ¹ H (400 MHz, DMSO-d ₆ ; ppm): δ = 2.23 (s, 3H), 6.79-6.82 (d, 2H), 6.87-6.92 (m, 4H), 6.96-7.00 (m, 3H) , 7.08 ~ 7.10 (d, 2H), 7.21, 7.23, 7.25 (t, 2H), 7.27 ~ 7.33 (m, 4H), 7.38 ~ 7.46 (m, 4H), 7.48 ~ 7.53 (m, 6H), 7.55 ~ 7.61 (m, 6H), 7.91-7.73 (d, 2H).

Example  7: Synthesis of Compound of Formula 1-20

Under a nitrogen atmosphere, 0.74 g (4 mmol) of 1-bromomethyl-4-methylbenzene and 0.83 g (5 mmol) of triethylphosphite were heated to 150 ° C., stirred for 3 hours, and then cooled to room temperature. 2.14 g (3 mmol) of the compound of Intermediate 7 and 20 ml of THF were added to the reaction solution, followed by stirring for 10 minutes. Then 1.34 g (12 mmol) of potassium t-butoxide (t-BuOK) was added and stirred at room temperature for 3 hours, followed by addition of excess water. The solid obtained was filtered and dried. The dried solid was purified by column chromatography to give 1.3 g of the compound of formula 1-20 (yield 54.2%).

NMR- ¹ H (400 MHz, CDCl ₃ ; ppm): δ = 6.90-6.72 (d, 2H), 6.96-6.97 (d, 2H), 7.00-7.02 (m, 5H), 7.05-7.07 (m, 2H) , 7.13--7.15 (d, 1H), 7.20--7.22 (d, 1H). 7.27 ~ 7.32 (m, 7H), 7.36 ~ 7.38 (m, 7H), 7.40 ~ 7.43 (m, 6H), 7.49 ~ 7.51 (m, 4H), 7.61 ~ 7.66 (m, 6H), 7.74 ~ 7.76 (d , 1H).

Example  8: Synthesis of Compound of Formula 1-26

Intermediate 9 (3.7 g, 5 mmol) was dissolved in 100 mL of purified THF under nitrogen atmosphere and cooled to -78 ° C. 3.2 mL (8 mmol, 2.5 M hexane solution) of n-butyl lithium was slowly added to the reaction solution for 30 minutes. After further stirring at the same temperature for 1 hour, chlorodiphenylphosphine (1.1 g, 5 mmol) was added slowly. After the cooling vessel was removed and stirred at room temperature for 3 hours, excess water was added to the reaction solution. Subsequently, the organic layer was extracted using methylene chloride, water was removed with anhydrous magnesium sulfate, and then the solvent was removed to obtain a white solid. The obtained white solid was dissolved in acetone, and excess hydrogen peroxide was added and stirred for about 10 minutes. The solvent was removed under reduced pressure to purify the column to obtain 3.5 g of a white compound of formula 1-26 (yield 80.8%).

NMR- ¹ H (400 MHz, DMSO-d ₆ ; ppm): δ = 6.81-6.63 (d, 2H), 6.90 (s, 4H), 6.94 (s, 1H), 6.96-7.01 (m, 5H), 7.02 ~ 7.04 (m, 3H), 708.-7.10 (d, 2H). 7.12 ~ 7.14 (d, 2H), 7.17 ~ 7.19 (d, 1H), 7.25 ~ 7.29 (m, 12H), 7.30 ~ 7.33 (m, 2H), 7.35 ~ 7.38 (m, 2H), 7.49 ~ 7.54 (m , 6H), 7.58-7.63 (m, 6H).

Hereinafter, a phosphorescent organic EL device manufactured using the compound according to the present invention as a light emitting layer forming material will be described with a comparative example.

Example  9: phosphorescent organic Electric field  Manufacture of light emitting device

First, using polyimide tape as a mask on a glass substrate coated with an ITO (indium tin oxide) thin film having a surface resistance of 10 Ω / □ and a thickness of 150 nm, and forming a first electrode pattern, hydrochloric acid is removed. (35%) and nitric acid (60%) were removed by etching with a 3: 1 solution. Ultrasonic washing was performed sequentially using a mixed solution of isopropyl alcohol and pure water 1: 1, pure water, and isopropyl alcohol solution, and then dried using an inert gas. 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (α-NPD) over washed ITO at a rate of 0.2-2.0 kPa / sec under a vacuum of 2 x 10 ^-6 torr Vacuum deposition was carried out to form a hole transport layer having a thickness of 30 nm. The compound of Formula 1-14 was vacuum-deposited at a rate of 0.2 to 2.0 kPa / sec under a vacuum of 2 x 10 ^-6 torr to form a 6 nm thick electron blocking layer. Subsequently, the compound of Formula 1-14 and tris (2-phenylpyridine) iridium (Irppy) were vacuum deposited on the electronic blocking layer at a rate of 1.0 mW / sec and 0.1 mW / sec, respectively, to form a light emitting layer having a thickness of 30 nm. Subsequently, B-alq was vacuum-deposited on the light emitting layer under a vacuum of 2 × 10 ⁻⁶ torr at a rate of 0.2˜2.0 μs / sec to form a first electron transport layer having a thickness of 15 nm. Subsequently, a compound of the following Chemical Formula 2-1 was vacuum-deposited at a rate of 0.2 to 2.0 mW / sec under a vacuum of 2 × 10 ⁻⁶ torr to form a second electron transport layer having a thickness of 30 nm. The compound of Chemical Formula 2-2 was vacuum deposited at a rate of 0.2 to 2.0 mW / sec under a vacuum of 2 × 10 ⁻⁶ torr to form an electron injection layer having a thickness of 3 nm.

,

,

[Formula 2-1] [Formula 2-2]

Subsequently, Al was vacuum-deposited thereon to form a cathode layer of about 200 nm to complete the phosphorescent organic light emitting device.

The maximum light emission wavelength of the completed phosphorescent organic EL device was 505 nm, and current efficiency was 33.67 cd / A and light emission efficiency was 11.27 lm / W at a current density of 10 mA / cm ² .

The synthesis method of Chemical Formula 2-1 is disclosed in Korean Patent Application No. 2005-0031628 of the applicant, and the synthesis method of Compound of Chemical Formula 2-2 is disclosed in Korean Patent Application 2006-0025213 of the applicant. have.

Comparative example  1: phosphorescent organic Electric field  Manufacture of light emitting device

The same method as in Example 9, except that CBP (4,4'-N, N'-dicarbazole-biphenyl) is used instead of the compound of Chemical Formula 1-14 in the emission layer, and the electron blocking layer is not formed. The organic electroluminescent element was completed.

The maximum light emission wavelength of the completed organic light emitting device was 505 nm, and the current efficiency was 12.8 cd / A and the light emission efficiency was 5.05 lm / W at a current density of 10 mA / cm ² .

Hereinafter, a phosphorescent organic EL device manufactured using the compound according to the present invention as an electron blocking layer forming material will be described with a comparative example.

Example  10 phosphorescent organic Electric field  Manufacture of light emitting device

NPD was vacuum-deposited on the washed ITO under a vacuum of 2 × 10 ⁻⁶ torr at a rate of 0.2˜2.0 μs / sec to form a hole transport layer having a thickness of 20 nm. The compound of Formula 1-14 was vacuum-deposited at a rate of 0.2 to 2.0 kPa / sec under a vacuum of 2 x 10 ^-6 torr to form a 20 nm thick electron blocking layer. Subsequently, CBP and [2- (4,6-difluorophenyl) pyridinato-N, C2 '] (picolinato) iridium (FIrpic) were vacuum-deposited on the electronic blocking layer in a ratio of 85:15. A light emitting layer of 40 nm was formed. Subsequently, the compound of the following formula 2-3 was vacuum deposited on the light emitting layer at a rate of 0.2 to 2.0 mW / sec under a vacuum of 2 × 10 ⁻⁶ torr to form a hole blocking layer having a thickness of 20 nm.

  [Formula 2-3]

Subsequently, the compound of Formula 2-1 was added on it under a vacuum of 2 × 10 ⁻⁶ torr of 0.2 to

Vacuum deposition at a rate of 2.0 mA / sec was performed to form an electron transport layer having a thickness of 30 nm. The compound of Chemical Formula 2-2 was vacuum-deposited at a rate of 0.2˜2.0 μs / sec under a vacuum of 2 × 10 ⁻⁶ torr to form an electron injection layer having a thickness of 3 nm. Subsequently, Al was vacuum-deposited thereon to form a cathode layer of about 200 nm to complete the phosphorescent organic light emitting device.

The maximum light emission wavelength of the phosphorescent organic EL device was 465 nm, with a current efficiency of 9.16 cd / A and a light emission efficiency of 2.67 lm / W at a current density of 10 mA / cm ² .

Method for synthesizing the compound of Formula 2-3 is disclosed in Korean Patent Application No. 2004-0054699 of the applicant.

Comparative example  2: organic Electric field  Manufacture of light emitting device

An organic light-emitting device was manufactured in the same manner as in Example 10, except that the thickness of the hole transport layer was increased to 40 nm instead of the electron blocking layer.

Table 1 summarizes the evaluation results of the organic electroluminescent devices produced in Examples 9 and 10 and Comparative Examples 1 and 2.

Emission wavelength Current Efficiency [@ 10mA / cm ² ] Luminous efficiency Example 9 505 nm 33.67 cd / A 11.27 lm / W Example 10 465 nm 9.16 cd / A 2.67 lm / W Comparative Example 1 505 nm 12.8 cd / A 5.05 lm / W Comparative Example 2 465 nm 6.92 cd / A 2.02 lm / W

 Comparing Example 9 with Comparative Example 1 in which only the host material of the light emitting layer of the organic light emitting device is compared, the organic electroluminescent device of Example 9 has a light emission efficiency of 123.2% and a current efficiency of 163.0 based on the light emitting device of Comparative Example 1 You can see that it is increased by% In addition, when comparing Example 10 in which the electron blocking layer was formed with the compound according to the present invention and Comparative Example 2 in which the electron blocking layer was not formed, the organic electroluminescent device of Example 10 was based on the light emitting device of Comparative Example 2. This shows that the current efficiency is increased by 32.4%. That is, the organic light emitting compound according to the present invention having an aryl phosphine oxide group and an aryl amine group simultaneously provides an organic electroluminescent device having a significantly increased luminous efficiency and current efficiency compared to a material used for a conventional organic electroluminescent device. Able to know.

2 is a graph showing the spectra of the organic electroluminescent devices fabricated in Example 9 and Comparative Example 1. FIG. Referring to FIG. 2, it can be seen that the organic electroluminescent device using the material of Chemical Formula 1-14 as the host material of the light emitting layer emits light at the same wavelength as that of the conventional host material.

3 is a graph showing the luminance of the organic EL device manufactured in Example 9 and Comparative Example 1 according to the current density. Referring to FIG. 3, it can be seen that the emission efficiency of the organic EL device of Example 9 is improved.

4 is a graph showing the spectrum of the organic electroluminescent device manufactured in Example 10 and Comparative Example 2. Referring to FIG. 4, it can be seen that the organic electroluminescent device in which the electron blocking layer is formed using the material of Chemical Formula 1-14 emits light at the same wavelength as the organic electroluminescent device manufactured in Comparative Example 2.

5 is a graph showing the luminance of the phosphorescent organic light emitting diodes manufactured in Example 10 and Comparative Example 2 according to current density. Referring to FIG. 5, it can be seen that the luminous efficiency of the organic light emitting diode of Example 10 is improved.

The organic electroluminescent device having the electron blocking layer forming material, the hole transport layer forming material and / or the host material of the light emitting layer formed by using the organic light emitting compound according to the present invention has excellent luminous efficiency, current efficiency and brightness.

Claims (12)

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

, here, Y is carbon or silicon; X ₁ and X ₂ are divalent linking groups, which may be the same or different, substituted or unsubstituted arylene of C6 to C18, or substituted or unsubstituted heteroarylene of C4 to C18; R ₁ and R ₂ may be the same or different, hydrogen, a substituted or unsubstituted alkyl group of C1 to C8, a substituted or unsubstituted aryl group of C6 to C24, a substituted or unsubstituted heteroaryl group of C4 to C24 Provided that R ₁ and R ₂ are not simultaneously hydrogen; Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be the same or different, a substituted or unsubstituted aryl group of C6 to C24, a substituted or unsubstituted heteroaryl group of C4 to C24; _One or more of R ₁ and R ₂ , R ₁ and X ₁ , R ₁ and X ₂ , or X ₁ and Ar ₁ may be connected to each other to form a fused ring. 2. A compound according to claim 1, wherein X ₁ and X ₂ are divalent linking groups comprising phenylene, biphenylene, furanylene, thiophenylene, pyridinylene, pyrrolylene or fluorenylene An organic light emitting compound characterized by the above. The compound according to claim 2, wherein the divalent linking group is further substituted with at least one substituent selected from the group consisting of methyl group, methoxy group, t-butyl group, fluorine group and trifluoromethyl group. The method of claim 1, wherein, R ₁ and R ₂ are a phenyl group, a naphthyl group, α-, β- naphthyl group, a biphenyl group, a 1-anthracenyl group, a 2-anthracenyl group, 9-anthracenyl group, 1-phenanthrenyl group , 2-phenanthrenyl group, 3-phenanthrenyl group, 4-phenanthrenyl group, 9-phenanthrenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9 -Fluorenyl group, 2-thiophenyl group, 3-thiophenyl group, 2-pyridinyl group, 3-pyridinyl group, 2-pyrrolyl group, 3-pyrrolyl group, 2-furanyl group, 3-furanyl group, 4-methylphenyl Group, 4-fluorophenyl group, 4-nitrophenyl group, 4-methylphenyl group, methyl group, ethyl group, 1-propyl group 2-propyl group, 1-butyl group, 2-butyl group, t-butyl group, 1-pentyl group, 2-pentyl group, 3-pentyl group, neopentyl group cyclohexyl group, n-hexyl group and nonyl group, characterized in that the compound selected from the group consisting of. The organic light emitting compound according to claim 4, wherein at least one of the hydrogen atoms of R ₁ or R ₂ is substituted by at least one of the following substituents:

,

,

or

. The compound of claim ₁ , wherein Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are a phenyl group, α-naphthyl group, β-naphthyl group, biphenyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl Group, 1-phenanthrenyl group, 2-phenanthrenyl group, 3-phenanthrenyl group, 4-phenanthrenyl group, 9-phenanthrenyl group, 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 9-fluorenyl group, 2-thiophenyl group, 3-thiophenyl group, 2-pyridinyl group, 3-pyridinyl group, 2-pyrrolyl group, 3-pyrrolyl group, 2-furanyl group, 3 -Furanyl group 4-methylphenyl group, 4-fluorophenyl group, 4-nitrophenyl group and 4-methylphenyl group selected from the group consisting of an organic light emitting compound. 7. An organic light emitting compound according to claim 6, wherein at least one of the hydrogen atoms of Ar ₁ or Ar ₂ is substituted by one or more of the following substituents:

, or

. The organic light emitting compound of claim 1, which is one of compounds represented by the following formula:

,

,

, [Formula 1-1] [Formula 1-2] [Formula 1-3]

,

,

, [Formula 1-4] [Formula 1-5] [Formula 1-6]

,

,

, [Formula 1-7] [Formula 1-8] [Formula 1-9]

,

,

, [Formula 1-10] [Formula 1-11] [Formula 1-12]

,

,

, [Formula 1-13] [Formula 1-14] [Formula 1-15]

,

,

, [Formula 1-16] [Formula 1-17] [Formula 1-18]

,

,

, [Formula 1-19] [Formula 1-20] [Formula 1-21] ,

,

,

, [Formula 1-22] [Formula 1-23] [Formula 1-24]

,

,

, [Formula 1-25] [Formula 1-26] [Formula 1-27]

,

,

, [Formula 1-28] [Formula 1-29] [Formula 1-30]

or

. [Formula 1-31] [Formula 1-32] A first electrode; Second electrode; And an organic layer interposed between the first electrode and the second electrode. An organic electroluminescent device, characterized in that the organic layer comprises the organic compound according to any one of claims 1 to 8. The organic electroluminescent device according to claim 9, wherein the organic layer is a light emitting layer. The organic electroluminescent device according to claim 10, wherein the light emitting layer further comprises at least one of a phosphorescent host, a fluorescent host, and a dopant in the visible light region. The organic electroluminescent device according to claim 9, wherein the organic layer is an electron blocking layer or a hole transport layer.

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