KR101163050B1 - Chemical Comprising Benzo Anthracene Have a Heterocyclic Ring and Organic Electronic Element using the same, Terminal thereof - Google Patents

Abstract

The present invention provides a compound having an indole derivative as a core, an organic electric device using the same, and a terminal thereof.

Description

A compound comprising a benzoanthracene constituting a heterocyclic ring, and an organic electronic device using the same, and a terminal thereof TECHNICAL COMPRISING Benzo Anthracene Have a Heterocyclic Ring and Organic Electronic Element using the same

The present invention relates to a compound comprising a benzoanthracene constituting a heterocyclic ring, an organic electric device using the same, and a terminal thereof.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as the light emitting material in order to increase the light emitting efficiency through the light emitting layer. The principle is that when a small amount of dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high-efficiency light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.

Embodiments of the present invention to solve the problems of the above-described background, a compound containing a benzoanthracene constituting a heterocyclic ring has been found, and when the compound is applied to an organic electronic device, the luminous efficiency, stability and It has been found that the lifespan can be greatly improved.

Accordingly, an object of the present invention is to provide a compound comprising a benzoanthracene constituting a heterocyclic ring, an organic electric device using the same, and a terminal thereof.

In one aspect, the present invention provides a compound of the formula:

The present invention is a hole injection, hole transport, electron injection, electron transport, suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, white, etc. according to a compound synthesized with a compound containing benzoanthracene constituting a heterocyclic ring It is useful as a luminescent material, and especially as a host material for fluorescent dopants of various colors.

The present invention also provides an organic electronic device using the compound having the above formula and a terminal including the organic electronic device.

The present invention is a compound containing a benzoanthracene constituting a heterocyclic ring hole injection, hole transport, electron injection, electron transport, luminescence suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, white, etc. It is useful as a material, and especially as a host material for fluorescent dopants of various colors.

1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.

Hereinafter, some embodiments of the present invention will be described in detail through exemplary drawings. In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected,""coupled," or "connected."

The present invention provides a compound of Formula 1 below.

(1) L ₁ and L ₂ are each independently a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted C1-50 An alkoxy group, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted arylene group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted carbon group having 5 to 60 carbon atoms A substituted or unsubstituted C1-C50 alkyl group or sulfur (S) containing at least one or more aryloxy groups, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) , A substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one of nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), Substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms containing at least one of oxygen (O), phosphorus (P) and silicon (Si) It is a ryloxy group.

(2) Ar ₁ and Ar ₂ each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted C1-50 An alkoxy group, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted arylene group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted carbon group having 5 to 60 carbon atoms A substituted or unsubstituted C1-C50 alkyl group or sulfur (S) containing at least one or more aryloxy groups, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) , A substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one of nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), Substituted or unsubstituted C5-C60 hetero containing at least one or more oxygen (O), phosphorus (P) and silicon (Si) It is an aryloxy group.

(3) R ₁ , R ₂ , R ₃ and R ₄ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms.

(4) n is an integer of 1-3.

Formula 1 may be represented by the following Formula 2 to Formula 7.

In Formula 2 to Formula 7, R ₅ , R ₆ , R ₇ and R ₈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 50 carbon atoms A group, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted arylene group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl having 5 to 60 carbon atoms A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or sulfur (S) containing at least one of oxy, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si), Substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms containing at least one of nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen Substituted or unsubstituted heteroaryl jade having 5 to 60 carbon atoms containing at least one (O), phosphorus (P) and silicon (Si) A group.

Specific examples of the compounds belonging to Formulas 1 to 7 which are compounds including benzoanthracene constituting a heterocyclic ring according to an embodiment of the present invention include compounds of the following Formula 8, but the present invention is not limited thereto.

Various organic electric devices exist in which compounds including benzoanthracene constituting the heterocyclic ring described with reference to Chemical Formulas 1 to 8 are used as the organic material layer. Examples of the organic electroluminescent device in which compounds including benzoanthracene constituting the heterocyclic ring described with reference to Chemical Formulas 1 to 8 may be used include, for example, an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC) drum, Organic transistors (organic TFTs).

An organic electroluminescent device (OLED) is described as an example of an organic electroluminescent device to which compounds including a benzoanthracene constituting a heterocyclic ring described with reference to Chemical Formulas 1 to 8 can be applied, but the present invention is not limited thereto. The compounds described above can be applied to electrical devices.

Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer of the organic electric field comprising the compounds of Formula 1 to 8 Provided is a light emitting device.

1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.

The organic light emitting device according to another embodiment of the present invention, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer And a structure known in the art using conventional manufacturing methods and materials in the art, except that at least one layer of the organic material layer including the electron injection layer is formed to include the compounds of Formulas 1 to 8. It can be prepared as.

The structure of the organic light emitting display device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited thereto. In this case, reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode. Although not shown, the organic light emitting diode further includes a hole blocking layer (HBL) that blocks hole movement, an electron blocking layer (EBL) that blocks electrons from moving, a light emitting auxiliary layer that helps or assists light emission, and a protective layer. It may be located. The protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.

In this case, the compounds including benzoanthracene constituting the heterocyclic ring described with reference to Chemical Formulas 1 to 8 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer. Specifically, the compound including the benzoanthracene constituting the heterocyclic ring described with reference to Formulas 1 to 8 may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer And a protective layer, or may be used in combination with them. Of course, the organic layer may be used not only in one layer but also in two or more layers. Meanwhile, the light emitting layer includes a host and a dopant. The compound including the benzoanthracene constituting the heterocyclic ring described with reference to Chemical Formulas 1 to 8 may be used as the host material.

In particular, it may be used as a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light emitting material according to the compound containing a benzoanthracene constituting a heterocyclic ring described with reference to the formula (1) to 8, in particular a host alone Can be used as a material.

For example, the organic light emitting device according to another embodiment of the present invention is a metal having a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation An oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. Can be prepared.

In addition to the above method, an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and 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.

The organic electroluminescent device according to another embodiment of the present invention may be used in a solution process such as spin coating or ink jet process using a compound based on the indole derivative described above.

The substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.

An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon. As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

The hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.

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 hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is positioned on the hole injection layer. The hole transport layer receives holes from the hole injection layer and transports the holes to the organic light emitting layer located thereon, and serves to prevent high hole mobility, hole stability, and electrons. In addition to these general requirements, when applied for vehicle body display, heat resistance to the device is required, and a material having a glass transition temperature (Tg) of 70 ° C. or higher is preferable. Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium oxide Compound, a silicon-based arylamine compound, and the like.

The organic light emitting layer is positioned on the hole transport layer. The organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.

Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 ') to increase blue light emission efficiency. [(1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine) can be used by doping in small amounts. In the case of red, DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H Small amounts of doping such as -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile) can be used. When the light emitting layer is formed using a process such as inkjet printing, roll coating, or spin coating, an organic light emitting layer is formed of a polymer of polyphenylene vinylene (PPV) or a polymer such as poly fluorene. Can be used for

The electron transport layer is positioned on the organic light emitting layer. The electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The electron injection layer is stacked on the electron transport layer. The electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like. At this time, the electron injection layer may be formed in a thickness range of 100 ~ 300Å.

The cathode is positioned on the electron injection layer. This cathode serves to inject electrons. As the material used as the cathode, it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection. In particular, a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used. In addition, an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 μm or less may also be used.

As described above, a hole injection material, a hole transport material, suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, and white, according to the compound including benzoanthracene forming a heterocyclic ring described with reference to Chemical Formulas 1 to 8, It can be used as a light emitting material, an electron transporting material and an electron injection material, it can be used as a host material of various colors.

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

Meanwhile, the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device. This terminal means a current or future wired or wireless communication terminal. The terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, various computers, and the like.

Example

Hereinafter, the present invention will be described in more detail with reference to Preparation Examples and Experimental Examples. However, the following Preparation Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Manufacturing example

Hereinafter, the preparation or synthesis examples of the compounds containing benzoanthracene constituting a heterocyclic ring belonging to the formula (8). However, since a large number of compounds including benzoanthracene constituting a heterocyclic ring belonging to the general formula (8), one or two of the compounds belonging to the general formula (8) will be exemplarily described. Those skilled in the art, that is, those skilled in the art through the preparation examples described below, it is possible to prepare a compound comprising a benzoanthracene constituting a heterocyclic ring belonging to the invention not illustrated.

Step 1-1) Synthesis of Intermediate A-1

After dissolving 10-Bromoanthracene-9-boronic acid, dimethyl-2,5-dibromoisophthalate, Pd (PPh ₃ ) ₄ , and K ₂ CO ₃ in anhydrous THF and a small amount of water, the mixture was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to give the desired intermediate A-1 (yield: 32%).

Step 1-2) Synthesis of Intermediate A-2

9-Anthraceneboronic acid, dimethyl-2,5-dibromoisophthalate, Pd (PPh ₃ ) ₄ , and K ₂ CO ₃ were dissolved in anhydrous THF and a small amount of water and refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated, and the resulting product was separated using column chromatography to obtain the desired intermediate A-2 (yield: 55%).

Step 1-3) Synthesis of Intermediate A-3

10-Bromoanthracene-9-boronic acid, dimethyl-2-bromoisophthalate, Pd (PPh ₃ ) ₄ , and K ₂ CO ₃ were dissolved in anhydrous THF and a small amount of water and refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to give the desired intermediate A-3 (yield: 38%).

Step 2-1) Synthesis of Intermediate B-1

The intermediate A-1 obtained in step 1-1) was dissolved in anhydrous THF, the temperature of the reaction was lowered to 78 ° C., the methylmagnesium bromide solution was slowly added dropwise, and the temperature of the reaction was slowly raised to reflux for 24 hours. After the reaction was completed, 2N-HCl aqueous solution was slowly added dropwise, stirred for 30 minutes, and extracted with CH ₂ Cl ₂ . The resulting product was concentrated using column chromatography to give the desired intermediate B-1 (yield: 62%).

Step 2-2) Synthesis of Intermediate B-2

The intermediate A-2 obtained in step 1-2) was dissolved in anhydrous THF, the temperature of the reaction was lowered to 78 ° C., and the methylmagnesium bromide solution was slowly added dropwise, and the temperature of the reaction was slowly raised to reflux for 24 hours. After the reaction was completed, 2N-HCl aqueous solution was slowly added dropwise, stirred for 30 minutes, and extracted with CH ₂ Cl ₂ . Water in the reaction was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to obtain the desired intermediate B-2 (yield: 65%).

Step 2-3) Synthesis of Intermediate B-3

The intermediate A-3 obtained in step 1-3) was dissolved in anhydrous THF, the temperature of the reaction was lowered to 78 ° C., the methylmagnesium bromide solution was slowly added dropwise, and the temperature of the reaction was slowly raised to reflux for 24 hours. After the reaction was completed, 2N-HCl aqueous solution was slowly added dropwise, stirred for 30 minutes, and extracted with CH ₂ Cl ₂ . After removing the water in the reaction with anhydrous MgSO ₄ and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired intermediate B-3 (yield: 68%).

Step 3-1) Synthesis of Intermediate C-1

The intermediate B-1 obtained in step 2-1) was dissolved in hot acetic acid, and an aqueous solution of HCl was added dropwise, followed by reflux for 3 hours. When the reaction was completed, the reaction was poured into iced water and the resulting solid was filtered under reduced pressure, separated by column chromatography to give the desired intermediate C-1 (yield: 51%).

Step 3-2) Synthesis of Intermediate C-2

Intermediate B-2 obtained in step 2-2) was dissolved in hot acetic acid, and an aqueous solution of HCl was added dropwise, followed by reflux for 3 hours. When the reaction was completed, the reaction was poured into iced water and the resulting solid was filtered under reduced pressure, separated by column chromatography to give the desired intermediate C-2 (yield: 55%).

Step 3-3) Synthesis of Intermediate C-3

Intermediate B-3 obtained in step 2-3) was dissolved in hot acetic acid, and an aqueous solution of HCl was added dropwise, followed by reflux for 3 hours. When the reaction was completed, the reaction was poured into iced water and the resulting solid was filtered under reduced pressure, separated by column chromatography to give the desired intermediate C-3 (yield: 53%).

Synthetic example ) One- subgenuses  (compound One )of Example

In step 3-1), the intermediate C-1, phenylboronic acid, Pd (PPh ₃ ) ₄ , and K ₂ CO ₃ were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to give the desired compound 1 (yield: 45%).

Synthetic example ) 2- subgenuses  (compound 58 )of Example

In step 3-2), intermediate C-2, 1-naphthylboronic acid, Pd (PPh ₃ ) ₄ , and K ₂ CO ₃ were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to give the desired compound 58 (yield: 56%).

Synthetic example ) 3- subgenuses  (compound 84 )of Example

In step 3-3), intermediate C-3, biphenylboronic acid, Pd (PPh ₃ ) ₄ , and K ₂ CO ₃ were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated and the resulting product was separated using column chromatography to give the desired compound 84 (yield: 50%).

Synthetic example ) 4- subgenuses  (compound 100 )of Example

The intermediate C-1 synthesized in step 3-1) and biphenylamine, Pd ₂ (dba) ₃ , P ( ^t Bu) ₃ and NaO ^t Bu were dissolved in a toluene solvent and then stirred at 110 ° C. for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. After removal of a small amount of water with anhydrous MgSO ₄ and filtration under reduced pressure, the resulting organic solvent was concentrated to give the desired compound 100 by column chromatography (yield: 53%).

Synthetic example ) 5- subgenuses  (compound 113 )of Example

Intermediate C-2 and 9,9-dimethyl- N- phenyl-9 H- fluoren-2-amine synthesized in step 3-2), Pd ₂ (dba) ₃ , P ( ^t Bu) ₃ and NaO ^t Bu Was dissolved in a toluene solvent and stirred at 110 ° C. for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. After removing a small amount of water with anhydrous MgSO ₄ and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 113 by column chromatography (yield: 52%).

Synthetic example 6- subgenuses  (compound 122 )of Example

Intermediate C-3 and dibiphenyl-4-ylamine, Pd ₂ (dba) ₃ , P ( ^t Bu) ₃ and NaO ^t Bu synthesized in step 3-3) were dissolved in toluene solvent, and then at 110 ° C. for 12 hours. Stirred. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. After removing a small amount of water with anhydrous MgSO ₄ and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 122 by column chromatography (yield: 51%).

abandonment Field  Manufacturing evaluation of the device

Compounds 1, 58, 84, 100, 113, and 122, each obtained through synthesis, were used as light emitting host materials or hole transporting layers of the light emitting layer, thereby manufacturing an organic light emitting diode according to a conventional method. First, a 60 nm thick hole injection layer (hole injection layer material: 4,4 ', 4' tris ( N- (2-naphthyl) -N -phenylamino) -tree on the ITO layer (anode) formed on the glass substrate Phenylamine (2T-NATA), hole transport layer 30 nm thick (hole transport layer material: N , N ' Di (naphthalen-1-yl) -N , N ' diphenylbenzidine (NPB)), a light emitting layer doped with 30% thick BD052X 7% (BD052X is a blue fluorescent dopant available from Idemitsu), 20 nm thick Electron transport layer (electron transport layer material: tris (8-quinolinolato) aluminum (Alq ₃ )), 1 nm thick electron injection layer (electron injection layer material: LiF) and 150 nm thick aluminum cathode was sequentially deposited An organic electroluminescent device was manufactured.

Comparative Experimental Example

When the compounds of the present invention were measured by the hole transport layer, a compound represented by the following Chemical Formula 9 (hereinafter abbreviated as 2-AND) was used as a light emitting host material instead of the compounds of the present invention for comparison. An organic electroluminescent device was manufactured.

Emitting layer
Host material Voltage
(V) Current density
(mA / cm ² ) Luminous efficiency
(cd / A) Chromaticity coordinates
(x, y) Example 1 Compound 1 5.92 14.72 7.33 (0.154, 0.141) Example 2 Compound 58 5.69 13.98 7.54 (0.151, 0.142) Example 3 Compound 84 5.57 13.75 7.85 (0.152, 0.142) Example 4 Compound 100 6.72 15.77 6.33 (0.153, 0.144) Example 5 Compound 113 6.23 15.12 6.42 (0.153, 0.143) Example 6 Compound 122 6.21 15.10 6.44 (0.152, 0.143) Comparative Example 1 2-ADN 6.89 15.81 6.31 (0.152, 0.143)

As can be seen from the results of Table 1, the organic light emitting display device using the organic light emitting device material of the present invention has a low driving voltage and excellent electrical stability and high luminous efficiency and lower than the conventional material (2-AND). Since it has a light emission luminance and can realize a high color purity and can also improve the lifespan, it can be used as a blue fluorescent light emitting material of an organic light emitting device and can significantly improve the light emitting efficiency and life of the organic light emitting device.

It is apparent that the compounds of the present invention can achieve the same effect even when used in other organic material layers of the organic light emitting device, for example, a hole transport layer as well as a light emitting layer, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer. Do.

While the present invention has been described in connection with what is presently considered to be practical exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It will be understood that the invention may be practiced. It is therefore to be understood that the embodiments described above are to be considered in all respects only as illustrative and not restrictive. In addition, the scope of the present invention is indicated by the following claims rather than the detailed description. Also, it is to be construed that all changes or modifications derived from the meaning and scope of the claims and their equivalent concepts are included in the scope of the present invention.

101: substrate 102: anode
103: hole injection layer 104: hole transport layer
105: light emitting layer 106: electron injection layer
107: electron transport layer 108: cathode

Claims (9)

A compound represented by the following formula (1).

In the above formula (1),
(1) L ₁ , L ₂ , Ar ₁ , Ar ₂ are each independently a hydrogen atom; Halogen atom; Cyano group; Thiol group ; Substituted or unsubstituted C1-C50 alkyl group ; Substituted or unsubstituted C1-C50 alkoxy group ; Substituted or unsubstituted C2-C50 alkenyl group ; Substituted or unsubstituted C6-C60 aryl group ; Substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms ; Substituted or unsubstituted C1-C50 heteroalkyl group containing at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) ; Substituted or unsubstituted C5- C60 heteroaryl group containing at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) ; And a substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms including at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) ; Is selected from the group consisting of

(2) R ₁ , R ₂ , R ₃ and R ₄ are each independently of the other hydrogen atoms; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms ; And a substituted or unsubstituted aryl group having 6 to 60 carbon atoms ; It is selected from the group consisting of.
(3) except that L ₁ , L ₂ , Ar ₂ , R ₁ to R ₄ are all hydrogen atoms and Ar ₁ is a hydrogen atom or a halogen atom. The compound represented by following General formula (2)-(4).

In the above formulas (2) to (4),
(1) R ₁ to R ₄ are each independently a hydrogen atom; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms ; And a substituted or unsubstituted aryl group having 6 to 60 carbon atoms ; Selected from the group consisting of,
(2) R ₅ to R ₈ are each independently of the other hydrogen atoms; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms ; A substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms ; A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms ; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms ; Substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms ; Substituted or unsubstituted C1-C50 heteroalkyl group containing at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) ; Substituted or unsubstituted C5- C60 heteroaryl group containing at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) ; And a substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms including at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) ; It is selected from the group consisting of. An organic electric device comprising at least one organic material layer comprising the compound of claim 1 or 2. The method of claim 3,
The organic electroluminescent device according to claim 1, wherein the organic layer is formed by a solution process. The method of claim 3,
The organic electronic device includes a first electrode, the organic material layer of one or more layers and the second electrode in a stacked form sequentially, organic electronic device. The method of claim 5,
The organic material layer is any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, an organic electric device. The method of claim 6,
The light emitting layer includes a host and a dopant,
The host is an organic electronic device comprising the compound. A display device comprising the organic electric element of claim 5;
And a control unit for driving the display device. The method of claim 8,
The organic electroluminescent device is an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC) drum, characterized in that one of the organic transistor (organic TFT).

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