WO2011108902A9

WO2011108902A9 - Compound comprising at least two compounds comprising at least two five-membered hetero rings, an organic electrical element using the same and a terminal thereof

Info

Publication number: WO2011108902A9
Application number: PCT/KR2011/001539
Authority: WO
Inventors: 박정환; 김대성; 김기원; 박용욱; 정화순; 변지훈; 박정근; 최대혁; 김동하
Original assignee: 덕산하이메탈(주)
Priority date: 2010-03-05
Filing date: 2011-03-07
Publication date: 2012-03-01
Also published as: KR20110100877A; WO2011108902A3; KR101181280B1; WO2011108902A2

Abstract

Provided are a compound comprising at least two compounds comprising at least two five-membered hetero rings, an organic electrical element using the same and a terminal thereof.

Description

Compound containing two or more compounds containing two or more five-membered heterocycle, and organic electric device using the same, the terminal

The present invention relates to a compound comprising two or more compounds containing two or more five-membered heterocycles, an organic electric device using the same, and a terminal thereof.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, 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 according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be. 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 the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. In order to increase the light emitting efficiency through the light emitting material, a host / dopant system may be used. 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 shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be 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.

The present inventors have found a compound containing a five-membered heterocyclic ring having a novel structure, and also found that when the compound is applied to an organic electric device, the luminous efficiency, stability and lifetime of the device can be greatly improved.

Accordingly, an object of the present invention is to provide a compound containing a novel five-membered hetero ring, an organic electric device using the same, and a terminal thereof.

In one aspect, the present invention provides a compound represented by the following formula.

The present invention provides a hole injection material, a hole transport material, a light emitting device suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, white, etc., according to a compound including two or more five or more heteroatomic heterocycles. It is useful as a material and / or electron transport material, and as a host material for phosphorescent 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.

Compounds containing two or more compounds containing two or more five-membered heterocycles may play various roles in organic electronic devices and terminals, and are suitable for fluorescent and phosphorescent devices of all colors such as red, green, blue, and white. It is useful as a hole injection material, a hole transport material, a light emitting material and / or an electron transport material, and is useful as a host material for phosphorescent 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 addition, in describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can 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. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

In one aspect, the present invention provides a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

(1) R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁ ', R ₂ ', R ₃ ', R ₄ ', R ₅ ′, R ₆ ′, R ₇ ′, R ₈ ′, R ₉ ′, and R ₁₀ ′ each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted carbon number 1 An alkyl group of 50 to 50, a substituted or unsubstituted alkoxy group of 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group of 1 to 50 carbon atoms, a substituted or unsubstituted arylene group of 5 to 60 carbon atoms, a substituted or unsubstituted carbon number 5 to Substitutes containing at least one aryl group of 60, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Or a substituted or unsubstituted C 5 to 60 carbon atoms containing at least one unsubstituted alkyl group having 1 to 50 carbon atoms or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si). Heteroaryl group or sulfur (S), nitrogen (N), oxygen (O), (P) and a silicon (Si) can heteroaryloxy substituted or unsubstituted carbon atoms of 5 to 60 ring date, including at least one.

(2) R ₁ to R ₁₀ and R ₁ ′ to R ₁₀ ′ may combine with adjacent groups to form a saturated or unsaturated ring. For example, neighboring R ₁ and R ₂ , R ₂ and R ₃ , ... R ₈ and R ₉ , R ₉ and R ₁₀ may combine to form a saturated or unsaturated ring. For example, neighboring R ₁ 'and R ₂ ', R ₂ 'and R ₃ ', ... R ₈ 'and R ₉ ', R ₉ 'and R ₁₀ ' may combine to form a saturated or unsaturated ring have.

(3) X may be carbon (C) or nitrogen (N).

(4) Ar represents a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 To 60 arylene group, substituted or unsubstituted aryl group having 5 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus ( A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or at least one of P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si); Substituted or unsubstituted C 5 to 60 containing at least one or more

Heteroaryl group or substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms containing at least one or more sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si). .

(5) The compound having the above structural formula can be used in a soluble process. That is, the organic material layer of the organic electric device, which will be described later, may be formed by a soluble process using the compound. In other words, the organic material layer of the organic electronic device is made by using a variety of polymer materials, and less by a solvent process (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method) rather than deposition. It can be prepared in a number of layers.

In another aspect, the present invention provides a compound represented by the following formula (2).

[Formula 2]

In another aspect, the present invention provides a compound represented by the formula (3) below.

[Formula 3]

Ar in Formulas 2 and 3 is the same as in Formula 1.

In Formulas 1 to 3, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁ ', R ₂ ', R ₃ ', R ₄ Substituents of ', R ₅ ', R ₆ ', R ₇ ', R ₈ ', R ₉ ', and R ₁₀ 'may be substituted or unsubstituted. When substituted, each independently of each other, a hydrogen atom, Halogen atom, cyano group, alkoxy group, thiol group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, substitution Or an 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 aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen ( A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and at least one of O), phosphorus (P) and silicon (Si); At least one silicon (Si) Substituted or unsubstituted containing at least one substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) It may be substituted with one selected from the group consisting of a heteroaryloxy group having 5 to 60 carbon atoms.

Specific examples of the compounds belonging to Chemical Formulas 1 to 3, which are compounds including two or more five-membered heterocyclic rings, according to one embodiment of the present invention include the compounds of Formula 4 below, but the present invention It is not limited only to. The compounds of Formula 4 below are represented by R ₁ to R ₁₀ and R ₁ 'to R ₁₀ ' are hydrogen atoms, but may be other functional groups described in Formulas 1 to 3.

In other words, the compounds represented by Formulas 1 to 3 may be represented by R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁ ', R ₂ ', Substituted or unsubstituted substituents of the substituents of R ₃ ′, R ₄ ′, R ₅ ′, R ₆ ′, R ₇ ′, R ₈ ′, R ₉ ′, and R ₁₀ ′ exemplify all compounds in a broad context. Since it is difficult to realistically describe exemplary compounds by way of example, the compounds represented by Chemical Formulas 1 to 3 not described in Chemical Formula 4 may also form part of the present specification.

[Formula 4]

Various organic electric devices exist in which compounds including two or more compounds including two or more five-membered heterocycles described with reference to Chemical Formulas 1 to 4 are used as the organic material layer. Examples of organic electroluminescent devices in which compounds including two or more compounds including two or more five-membered heterocycles described with reference to Chemical Formulas 1 and 4 may be used include, for example, an organic light emitting diode (OLED), an organic solar cell, Organophotoreceptor (OPC) drums, organic transistors (organic TFTs), photodiodes, organic lasers, laser diodes, and the like.

One example of an organic electroluminescent device to which compounds including two or more five-membered heterocyclic rings described with reference to Chemical Formulas 1 to 4 may be applied is described below. The present invention is not limited thereto, and a compound including two or more compounds including two or more five-membered heterocycles described above may be applied to various organic electric 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 these electrodes, wherein at least one layer of the organic material layer comprises an organic electric field comprising the compounds of Formulas 1 to 4 Provided is a light emitting device.

In an organic light emitting display device according to another embodiment of the present invention, at least one layer of 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 to include the compounds of Formulas 1 to 6 above. Except for the above, it may be manufactured in a structure known in the art using conventional manufacturing methods and materials in the art.

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 may further include a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for preventing the movement of electrons, and a protective layer. The protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.

In this case, the compound including two or more compounds containing two or more five-membered heterocyclic ring described with reference to Formulas 1 to 4 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. have. Specifically, the compound including two or more compounds containing two or more five-membered heterocyclic ring described with reference to Formulas 1 to 4 is a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, It may be used in place of one or more of the electronic blocking layer, the protective layer, or may be used by forming a layer with them. Of course, the organic layer may be used not only in one layer but also in two or more layers.

Compounds containing two or more compounds containing two or more five-membered heterocycles described with reference to Formulas 1 to 4 may play various roles in the organic electronic device and the terminal, and all of red, green, blue, white, etc. It is useful as a hole injection material, a hole transport material, a light emitting material and / or an electron transport material suitable for color fluorescence and phosphorescent devices, and can be used as a host material for phosphorescent dopants of various colors.

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 by using a variety of polymer materials, and by using a process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.

An organic light emitting display device according to another embodiment of the present invention forms an organic material layer, for example, a light emitting layer, by a soluble process of a compound containing two or more compounds including two or more five-membered heterocycles described above. You may.

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, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.

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.

The hole injection material is a material capable of well injecting holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material 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, applications for vehicle body display require heat resistance to the device, and materials having a glass transition temperature (Tg) of 70 or greater are preferred. Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene and 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. Such an electron transport layer requires a material having high electron injection efficiency and efficiently transporting injected electrons from a cathode positioned thereon. 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 ~ 300.

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 or less can also be used.

As described above, holes suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, and white, depending on the compound including two or more compounds including two or more five-membered heterocycles described with reference to Chemical Formulas 1 to 12 It can be used as an injection material, a hole transport material, a light emitting material, an electron transport material and an electron injection material, and can be used as a host material for phosphorescent dopants 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.

Production Example

Hereinafter, the preparation or synthesis examples for the compounds containing two or more compounds containing two or more five-membered heterocycles belonging to the formula (4). However, a compound containing two or more compounds containing two or more five-membered heterocycles belonging to Formula 4 because the number of compounds including two or more five-membered heterocyclic rings belonging to Formula 4 is large One or two of them will be described by way of example. Those skilled in the art, that is, those skilled in the art through the preparation examples described below, a compound comprising two or more compounds containing two or more five-membered heterocyclic ring belonging to the present invention not illustrated Can be prepared.

Step 1) Synthesis of Intermediate A

Scheme 1

[Revisions under Rule 91 28.04.2011]

Starting materials S, 1,3,5-tribromobenzene, Pd ₂ (dba) ₃ , P ( ^t Bu) ₃ and NaO ^t Bu were dissolved in toluene solvent and then stirred at 110 to 24 hours. After the reaction was completed, the temperature of the reactant was lowered to room temperature, and the resulting solid was filtered under reduced pressure, and then recrystallized with hot toluene solvent to obtain the desired intermediate A (yield: 69%).

Step 2) Synthesis of Intermediate B

Scheme 2

[Revisions under Rule 91 28.04.2011]

The intermediate A obtained in step 1) was dissolved in anhydrous THF, the temperature of the reaction was lowered to 8, n-BuLi (1.6 M in hexane) was slowly added dropwise, and the reaction was stirred at 0 to 1 hour. The temperature of the reaction was lowered to -78, Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added dropwise and stirred at room temperature for 12 hours. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ , water was removed from the reaction with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated to give the resulting product as methyl alcohol.

Recrystallization was used to afford the desired intermediate B (yield: 62%).

Step 3) Synthesis of Intermediate C

Scheme 3

[Revisions under Rule 91 28.04.2011]

Starting materials S, Cyanuric chloride, Pd ₂ (dba) ₃ , P ( ^t Bu) ₃ and NaO ^t Bu were dissolved in toluene solvent and stirred at 110 to 24 hours. After the reaction was completed, the temperature of the reactant was lowered to room temperature, and the resulting solid was filtered under reduced pressure, and then recrystallized with hot toluene solvent to obtain the desired intermediate C (yield: 49%).

Synthesis Example 1 Synthesis of Compound 10

Scheme 4

[Revisions under Rule 91 28.04.2011]

The intermediate A, 9-Anthraceneboronic acid, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ synthesized in step 1) were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 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 organic solvent was concentrated and the resulting product was recrystallized using a toluene solvent to give the desired compound 10 (yield: 71%).

Synthesis Example 2 Synthesis of Compound 26

Scheme 5

[Revisions under Rule 91 28.04.2011]

The intermediate B, 2-Iodo-4,6-diphenylpyrimidine, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ synthesized in step 2) were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 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 organic solvent was concentrated and the resulting product was recrystallized using a toluene solvent to give the desired compound 26 (yield: 54%).

Synthesis Example 3 Synthesis of Compound 38

Scheme 6

[Revisions under Rule 91 28.04.2011]

Intermediate C, 2-Naphthylboronic acid, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ synthesized in step 3) were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 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 organic solvent was concentrated and the resulting product was recrystallized using a toluene solvent to give the desired compound 38 (yield: 77%).

Synthesis Example 4 Synthesis of Compound 56

Scheme 7

[Revisions under Rule 91 28.04.2011]

Intermediate C, Quinolin-3-ylboronic acid, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ synthesized in step 3) were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 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 organic solvent was concentrated and the resulting product was recrystallized using a toluene solvent to give the desired compound 56 (yield: 65%).

In this case, the compounds represented by Formulas 1 to 3 are R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁ ', R ₂ ', R ₃ Substituted or unsubstituted substituents of the substituents of ', R ₄ ', R ₅ ', R ₆ ', R ₇ ', R ₈ ', R ₉ ', and R ₁₀ ' are compounds represented by the general formula (4) in a broad relationship. Synthesis examples of some of the above, but the compounds represented by the formula (1) to 4 not illustratively described as a synthesis example may also form part of the present specification.

Manufacturing Evaluation of Organic Field Devices

Compounds 10, 26, 38, and 56 obtained through synthesis were used as light emitting host materials of the light emitting layer, respectively, to fabricate an organic light emitting diode according to a conventional method.

First, a copper phthalocyanine (hereinafter abbreviated as CuPc) film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a thickness of 10 nm. Subsequently, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as a-NPD) was vacuum-deposited on the membrane as a major transport compound. A hole transport layer was formed.

After the hole transport layer was formed, compounds 10, 26, 38, and 56 were deposited on the hole transport layer as phosphorescent host materials to form a light emitting layer.

At the same time, tris (2-phenylpyridine) iridium (abbreviated as I r (ppy) ₃ hereinafter) was added as a phosphorescent Ir metal complex dopant. At this time, the concentration of I r (ppy) _{3 in} the light emitting layer was 5% by weight. (1,1-bisphenyl) -4-oleato) bis (2-methyl-8-quinolinoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, followed by electrons. Tris (8-quinolinol) aluminum (hereinafter abbreviated to Alq ₃ ) was formed into an injection layer to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to use an Al / LiF as a cathode to prepare an organic light emitting device.

Comparative Example 1

For comparison, an organic electroluminescent device having the same structure as the test example was manufactured using a compound represented by Chemical Formula 13 (hereinafter abbreviated as CBP) as a light emitting host material instead of the compound of the present invention.

[Formula 5]

Table 1

	Host material of emitting layer	Voltage (V)	Current density (mA / cm ² )	Luminance (cd / m ² )	Luminous Efficiency (cd / A)	Chromaticity coordinates (x, y)
Example 1	Compound 10	5.1	0.31	107	62.3	(0.30, 0.60)
Example 2	Compound 26	4.9	0.30	105	68.2	(0.32, 0.61)
Example 3	Compound 38	5.2	0.33	107	58.3	(0.30, 0.60)
Example 4	Compound 56	5.0	0.32	107	65.3	(0.30, 0.60)
Comparative Example 1	CBP	6.1	0.31	101	32.6	(0.33, 0.61)

As can be seen from the results of Table 1, as can be seen from the results of the table, the organic electroluminescent device using the organic electroluminescent device material of the present invention is not only excellent in the luminous efficiency compared to the CBP used as a comparative example, Since green light emission is obtained in which color purity is remarkably improved, it is used as a phosphorescent host material of an organic light emitting display device, and thus light emission efficiency and color purity may be remarkably improved.

It is apparent that the same effect can be obtained even when the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, the host material of the light emitting layer, as well as the electron injection layer, the electron transport layer, the hole injection layer and the hole transport layer.

In this case, the compounds represented by Formulas 1 to 4 are R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁ ', R ₂ ', R ₃ Substituted or unsubstituted substituents of ', R ₄ ', R ₅ ', R ₆ ', R ₇ ', R ₈ ', R ₉ ', and R ₁₀ ' are some of the compounds represented by the formula (4) in a broad relationship. Compounds represented by the formulas (1) to (3), which have been described by way of example but not described by way of example, are also the same as the aforementioned comparative examples because of the above-described parent nucleus structure of the formulas (1) to (3). It can be confirmed that the effect and the results may form part of the present specification.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments.

The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application is filed in Korea on March 5, 2010. Patent Application No. 10-2010-

0019950 claims priority under U.S. Patent Act Article 119 (a) (35 U.S.C § 119 (a)), all of which is incorporated herein by reference. In addition, if this patent application claims priority for the same reason as above for a country other than the United States, all the contents thereof are incorporated into this patent application by reference.

Claims

A compound represented by the following formula.

In the above formula,

(1) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 1 ', R 2 ', R 3 ', R 4 ', R 5 ′, R 6 ′, R 7 ′, R 8 ′, R 9 ′, and R 10 ′ each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted carbon number 1 An alkyl group of 50 to 50, a substituted or unsubstituted alkoxy group of 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group of 1 to 50 carbon atoms, a substituted or unsubstituted arylene group of 5 to 60 carbon atoms, a substituted or unsubstituted carbon number 5 to Substitutes containing at least one aryl group of 60, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Or a substituted or unsubstituted C 5 to 60 carbon atoms containing at least one unsubstituted alkyl group having 1 to 50 carbon atoms or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si). Heteroaryl group or sulfur (S), nitrogen (N), oxygen (O), (P) and a silicon (Si) substituted or unsubstituted hetero aryloxy group having 5 to 60 ring containing at least one,

(2) X is carbon (C) or nitrogen (N),

(3) Ar is a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 To 60 arylene group, substituted or unsubstituted aryl group having 5 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N), oxygen (O), phosphorus ( A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or at least one of P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si); Substituted or unsubstituted C 5 to 60 containing at least one or more

Heteroaryl group or substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms containing at least one or more sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si).
[Revisions under Rule 91 28.04.2011]

The compound according to claim 1, wherein the compound is a compound represented by the following formula.
[Revisions under Rule 91 28.04.2011]

The compound according to claim 1, wherein the compound is a compound represented by the following formula.
The method of claim 1,

R 1 to R 10 and R 1 ′ to R 10 ′ combine with adjacent groups to form a saturated or unsaturated ring.
[Revisions under Rule 91 28.04.2011]

The method of claim 1,

The compound is,

Compounds, characterized in that one selected from the group consisting of.
An organic electric device comprising at least one organic material layer comprising a compound of any one of claims 1 to 5.
The method of claim 6,

The organic electroluminescent device according to claim 1, wherein the organic layer is formed by a solution process.
The method of claim 6,

The organic electroluminescent device is an organic electroluminescent device comprising a first electrode, the at least one organic material layer and the second electrode in a stacked form sequentially.
The method of claim 8,

The organic material layer includes a light emitting layer,

The organic electroluminescent device according to claim 1, wherein the compound is used as a host material in the emission layer.
A display device comprising the organic electric element of claim 6;

And a control unit for driving the display device.
The method of claim 10,

The organic electroluminescent device includes an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC) drum, an organic transistor (organic TFT), a photodiode, an organic laser, and a laser diode. Terminal) characterized in that one of.