KR20110034103A - Compound containing heterocyclic 5-membered ring derivative condensed aryl ring and organic electronic element using the same, terminal thereof - Google Patents

Abstract

PURPOSE: A compound containing heterocyclic 5-membered ring derivative in which an aryl ring is condensed is provided to improve luminous efficiency, stability and lifetime, and to enable use for hole injection, hole transport, electron injection, electron transport, and luminescent material. CONSTITUTION: A compound is represented by chemical formula: Z-(Y)n. In chemical formula, Z is substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group; Y is a radical represented by chemical formula 2, wherein n is an integer of 1-6. In chemical formula 2, R1 ~ R9 are selected from the group consisting of halogen group, C1 ~ C60 alkyl group, alkoxy group, alkylamine group, arylamine group, alkyl thiophene group, C6 ~ C60 aryl thiophene group, C2 ~ C600 alkenyl group, C2 ~ C60 alkynyl group, C3 ~ C60 cycloalkyl group, and C6 ~ C60 aryl group.

Description

Compound Containing Heterocyclic 5-Membered Ring Derivative Condensed Aryl Ring And Organic Electronic Element Using The Same, Terminal Thereof}

The present invention relates to a compound having a heterocyclic 5-membered ring derivative in which an aryl ring is condensed, 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 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 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 having a heterocyclic 5-membered ring derivative condensed with an aryl ring having a novel structure has been found, and also applied to the organic electric device It has been found that the light emitting efficiency, stability and lifetime of the device can be greatly improved.

Accordingly, an object of the present invention is to provide a compound having a heterocyclic 5-membered ring derivative in which a novel aryl ring is condensed, an organic electric device using the same, and a terminal thereof.

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

Z- (Y) n

In the above formula, Z represents a group consisting of a substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group, Y represents a group represented by the following General Formula (2), and n represents an integer of 1 to 6.

The present invention is a compound having a heterocyclic 5-membered ring derivative in which an aryl ring is condensed, and is useful as a hole injection, a hole transport, an electron injection, an electron transport, a light emitting material and / or a passivation (kepping) material, in particular a host or a plate alone Useful as

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 having a heterocyclic 5-membered ring derivative in which an aryl ring is condensed, and is useful as a hole injection, a hole transport, an electron injection, an electron transport, a light emitting material and / or a passivation (kepping) material, in particular a host or a plate alone Useful as

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 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 another component may be It is to be understood that the components may be "connected", "coupled" or "connected".

The present invention provides a compound of Formula 1 below.

In Formula 1, Z represents a group consisting of a substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group, Y represents a group represented by the following formula (2), n represents an integer of 1-6.

R ₁ to R ₉ are the same as or different from each other, and each independently a halogen group, a C ₁ to C ₆₀ alkyl group, a C ₁ to C ₆₀ alkoxy group, a C ₁ to C ₆₀ alkylamine group, C ₁ to C ₆₀ Arylamine group, C ₁ to C ₆₀ alkyl thiophene group, C ₆ to C ₆₀ aryl thiophene group, C ₂ to C ₆₀₀ alkenyl group, C ₂ to C ₆₀ alkynyl group, C ₃ to C ₆₀ a cycloalkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted with a heavy hydrogen aryl, C ₈ ~ C ₆₀ aryl alkenyl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron C ₆ ~ C ₆₀ aryl group which is unsubstituted or substituted with one or more groups selected from the group consisting of a desired group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted heterocyclic group of C ₅ to C ₆₀ halogen, CN, NO _2, C ₁ ~ alkoxy group of C ₆₀ alkyl group, C ₁ ~ C ₆₀ of, C ₁ ~ alkyl amine group of the C _60, C ₁ ~ a C ₆₀ alkylthio group, C of ₂ ~ C ₆₀ alkenyl group, C ₂ of ₆₀ ~ C alkynyl group, C ₃ ~ C ₆₀ of Sickle Alkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and a substituted Or an unsubstituted C ₅ ~ C ₆₀ heterocyclic group or C ₆ ~ C ₆₀ aromatic ring substituted with one or more groups selected from the group consisting of C ₅ ~ C ₆₀ heterocyclic group and C ₄ ~ C ₆₀ An aliphatic ring condensed ring group, each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, a substituted and unsubstituted heteroaryl group, Adjacent positions may be bonded to each other to form a ring, and may be represented by the following Chemical Formula 3 in detail. X represents C, N, O, S, Si, P, Ge. One of R ₁ to R ₉ is Z.

In Chemical Formula 3, R ₁₀ to R ₁₅ may independently have the same meaning as R ₁ to R _9, and ring A condensed to indole may be represented by the following Formula 4.

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중 선택된 어느 하나를 포함한다.

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It includes any one selected.

When n is 1 in Z- (Y) n of Chemical Formula 1, it may be represented by Chemical Formula 5.

In Formula 4, any one of R represents Z.

When n is 2 or more in Z- (Y) n of Chemical Formula 1, it may be represented by any one of Chemical Formula 6 below.

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As a specific example of the compound belonging to Formula 1 to 6 which is a compound having a heterocyclic 5-membered ring derivative in which an aryl ring is condensed according to an embodiment of the present invention, the compounds of Formulas 7a to 7d (hereinafter referred to as Formula 7) However, the present invention is not limited to these.

Various organic electric devices exist in which compounds having a heterocyclic 5-membered ring derivative having an aryl ring condensed with reference to Chemical Formulas 1 to 7 are used as the organic material layer. Examples of the organic electroluminescent device in which compounds having a heterocyclic 5-membered ring derivative in which the aryl ring is condensed with reference to Chemical Formulas 1 to 7 may be used include, for example, an organic electroluminescent device (OLED), an organic solar cell, and an organic photoconductor (OPC). ) And organic transistors (organic TFTs).

An organic electroluminescent device (OLED) will be described as an example of an organic electric device to which compounds having a heterocyclic 5-membered ring derivative in which an aryl ring is condensed with reference to Chemical Formulas 1 to 7 can be applied, but the present invention is not limited thereto. And a compound having a heterocyclic 5-membered ring derivative in which the aryl ring is condensed as 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 the electrodes, wherein at least one of the organic material layer of the organic electric field comprising the compounds of Formulas 1 to 7 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 7. 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 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 having a heterocyclic 5-membered ring derivative in which the aryl ring described with reference to Formulas 1 to 7 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 having a heterocyclic 5-membered ring derivative in which the aryl ring is condensed with reference to Formulas 1 to 7 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, It may be used in place of one or more of the protective layers or in combination with them. Of course, the organic layer may be used not only in one layer but also in two or more layers.

In particular, the hole injection material, the hole transport material, the electron injection material, the electron transport material, the light emitting material and the passivation (kepping) material according to the compound having a heterocyclic 5-membered ring derivative condensed with the aryl ring described with reference to the formula (1) It can be used as, and in particular can be used as a light emitting material and a host or dopant alone.

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 light emitting device according to another embodiment of the present invention is a soluble process such as spin coating or ink jet process of a compound having a heterocyclic 5-membered ring derivative condensed with the aryl ring described above May be used.

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 a positive electrode material, a material having a large work function is generally 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 positioned 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 suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, and white, according to the compound having a heterocyclic 5-membered ring derivative in which the aryl ring described with reference to Chemical Formulas 1 to 7 is condensed, holes It can be used as a transport material, a light emitting material, an electron transport material and an electron injection material, and can be used as a host or dopant 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 controller, 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 of the compounds having a heterocyclic 5-membered ring derivative in which the aryl ring belonging to the formula (3) is condensed will be described. However, since the number of compounds having a heterocyclic 5-membered ring derivative in which the aryl ring of Formula 3 is condensed is large, one or two of the compounds having a heterocyclic 5-membered ring derivative in which the aryl ring of Formula 3 is condensed Explain. Those of ordinary skill in the art, that is, those skilled in the art can prepare a compound having a heterocyclic 5-membered ring derivative condensed with an aryl ring belonging to the present invention, which is not illustrated by the preparation examples described below. have.

Synthetic

In the above synthesis, if A is Phenanthrene and Ar is H, Phenyl or Methyl, then Intermediate 3 and Intermediate 7 are Tetrahedron Vol. 30. 2983, (1974).

Intermediate 4 Method when A is Phenanthrene

Add intermediate 3 and NBS to a 250mL 2-neck round flask and stir at 40 ° C for 12 hours. After completion of the reaction, the mixture was extracted with MC and water, dried over MgSO 4, concentrated, and recrystallized with Hexane to give 7 g of a white solid (yield 81%).

Synthesis when A is Phenanthrene and Ar is Phenyl in Intermediate 5

Phenylboronic acid, Intermediate 4 and tetrakis triphenyl phosphine palladium were added to K ₂ CO ₃ in 500 ml of THF and 250 ml of water and heated to reflux for 24 hours. The obtained solid was washed with water and methanol and then separated by silica gel column chromatography to give intermediate 5 (yield 60%).

Method for synthesizing compound B-4 (substance 6 in the above synthesis)

Two equivalents of Intermediate 5, 1,4-Dibromobiphenyl, Pd2 (dba) 3, Triphenylphosphine, and Sodium tert-butoxide were added to a toluene solvent and stirred under reflux for 24 hours at 130 ° C. After completion of the reaction, the mixture was extracted with MC, water, dried over MgSO 4, concentrated, and the resulting compound was separated using column chromatography to obtain the desired compound B-4. (Yield 36%)

Synthesis when A is Phenanthrene and Ar is Phenyl in Intermediate 8

It is the same as the synthesis method of intermediate 4, except that intermediate 7 is substituted for intermediate 3.

Synthesis when A is Phenanthrene and Ar is Phenyl in Intermediate 9

After dissolving intermediate 8 in THF, n-BuLi was slowly added dropwise at -78 degrees, followed by stirring for a minute. Triisopropylborate was then slowly added dropwise at -78 ° C, stirred, acidified with 1N HCl, extracted with water and EA, dried over MgSO4 and recrystallized with Hexane (yield 52%).

Method for synthesizing compound B-2 (Substance No. 10 in the above synthesis)

Dissolve 2 equivalents of Intermediate 9 and 1,4-Dibromobiphenyl in THF, add NaOH and H2O and stir to reflux. After completion of the reaction, the mixture was extracted with water and MC, dried over MgSO 4, column was purified by silica gel chromatography, and then recrystallized with Hexane to give a product (yield 84%).

Method for synthesizing compound A-14 (substrate 11 in the above synthesis)

The same procedure as for the synthesis of Compound B-2 was carried out except that 2-equivalent intermediate 9 instead of 1 equivalent intermediate 9 and 1,4-Dibromobiphenyl were added 2-chloro-4,6-diphenyl-1,3,5-Triazine.

Thianthrene was dissolved in anhydrous THF and n- BuLi (1.6 M in hexane) was added dropwise at -78 ° C, followed by stirring at room temperature for 1 hour. The temperature of the reaction was lowered to 78 ° C and Chlorotrimethylsilane was added dropwise, followed by stirring at room temperature for 12 hours. At the end of the reaction, extracted with Ethyl acetate 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. (Yield 95%).

abandonment Field  Manufacturing evaluation of the device

Various compounds obtained through synthesis were used as light emitting host materials or hole transporting layers of the light emitting layer, respectively, to fabricate an organic light emitting device 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, when measured with a green host, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (abbreviated as a-NPD) was used as the major transport compound on this membrane. Vacuum deposition to a thickness of nm to form a hole transport layer. After the formation of the hole transport layer, when measuring the hole transport layer, an emission layer doped with BD-052X (Idemitus) having a 45 nm thickness of 7% on the hole transport layer (where BD-052X is a blue fluorescent dopant, is a light emitting host material) As the furnace, 9,10-di (naphthalene-2-anthracene (AND)) was used.

When measuring with a phosphorescent host material, a phosphorescent material was deposited to form a light emitting layer, and tris (2-phenylpyridine) iridium (hereinafter abbreviated as I r (ppy) ₃ ) 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 10% by weight. (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolinoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a hole blocking layer to a thickness of 10 nm. Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was formed into an electron injection layer to a thickness of 40 nm. Subsequently, 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 prepare an organic light emitting device by using this Al / LiF as a cathode.

Comparative Experimental Example

For comparison, an organic electroluminescent device having the same structure as the test example was manufactured using a compound represented by Formula 8 (hereinafter abbreviated as CBP) as a light emitting host material instead of the compound of the present invention.

Emitting layer
Host material Voltage
(V) Current density
(mA / cm ² ) Luminous efficiency
(cd / A) Chromaticity coordinates
(x, y) Example 1 Compound a-12 5.4 0.31 47.3 (0.31, 0.60) Example 2 Compound a-13 5.6 0.32 46.2 (0.31, 0.60) Example 3 Compound a-14 5.2 0.31 45.2 (0.29, 0.60) Example 4 Compound b-3 5.8 0.32 42.4 (0.32, 0.63) Comparative Example 1 CBP 6.1 0.31 32.6 (0.33, 0.61)

Also, when the compounds of the present invention were measured by the hole transport layer, NPB was used as the hole transport material instead of the compound of the present invention to prepare an organic light emitting display device having the same structure as the test example.

Emitting layer
Host material Voltage
(V) Current density
(mA / cm ² ) Luminous efficiency
(cd / A) Chromaticity coordinates
(x, y) Example 1 Compound A-25 6.7 13.01 8.6 (0.15, 0.14) Example 2 Compound a-26 5.8 13.11 8.2 (0.15, 0.15) Example 3 Compound A-35 6.2 12.98 8.5 (0.15, 0.14) Example 4 Compound a-37 5.9 12.77 8.3 (0.15, 0.14) Comparative Example 1 NPB 7.2 13.35 7.5 (0.15, 0.15)

As can be seen from the results of Table 1 and Table 2, the organic electroluminescent device using the organic electroluminescent device material of the present invention has high efficiency and color purity as well as green light emission of long life is obtained, so that the green of the organic light emitting device It can be used as a phosphorescent host material to significantly improve luminous efficiency and lifetime.

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 light emitting layer, as well as an electron injection layer, an electron transport layer, a hole injection layer and a hole transport layer.

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. Therefore, the embodiments described above are to be understood as illustrative and not restrictive in all aspects. In addition, the scope of the present invention is shown by the claims below, rather than the above 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.

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

Claims (10)

Compound represented by the following formula. Z- (Y) n (One) In the formula (1), Z represents a group consisting of a substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group, Y represents a group represented by the following General Formula (2), and n represents an integer of 1 to 6.

(2) In the general formula (2), R ₁ to R ₉ are the same as or different from each other, and each independently a halogen group, a C ₁ to C ₆₀ alkyl group, a C ₁ to C ₆₀ alkoxy group, and a C ₁ to C ₆₀ alkyl Amine group, C ₁ to C ₆₀ arylamine group, C ₁ to C ₆₀ alkyl thiophene group, C ₆ to C ₆₀ aryl thiophene group, C ₂ to C ₆₀₀ alkenyl group, C ₂ to C ₆₀ alkynyl, C cycloalkyl group of _{3 ~ C 60, C 6 ~} C ₆₀ aryl group, of a C ₆ ~ C ₆₀ substituted by deuterium aryl group, an arylalkenyl group of C ₈ ~ C _60, a substituted or unsubstituted silane C ₆ -C unsubstituted or substituted with one or more groups selected from the group consisting of a group, a substituted or unsubstituted boron group, a substituted or unsubstituted germanium group, and a substituted or unsubstituted C ₅ -C ₆₀ heterocyclic group ₆₀ aryl group, _{halogen, CN, NO 2, C 1} ~ alkoxy group of C ₆₀ alkyl group, C ₁ ~ C ₆₀ of, C ₁ ~ alkyl amine group of the C _60, coming C ₁ ~ C ₆₀ alkyl group, C ₂ Alkenyl group of C ₆₀ , C _{2 of} C ₆₀ An alkynyl group, a C ₃ to C ₆₀ cycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₆₀ aryl group substituted with deuterium, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, C ₅ ~ C ₆₀ heterocyclic group or C ₆ ~ C ₆₀ substituted or unsubstituted or substituted with one or more groups selected from the group consisting of a substituted or unsubstituted germanium group, and a substituted or unsubstituted C ₅ ~ C ₆₀ heterocyclic group A condensed ring group of an aromatic ring and a C ₄ to C ₆₀ aliphatic ring, each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, a substituted and unsubstituted hetero Arbitrary groups selected from an aryl group, adjacent positions may be bonded to each other to form a ring, represented by the following general formula (3), X represents C, N, O, S, Si, P, Ge, Any one of R ₁ to R ₉ is Z.

       (3) In the general formula (3), R ₁₀ to R ₁₅ independently have the same meanings as R ₁ to R ₉ , Ring A condensed to indole is

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It includes any one selected. The method of claim 1, In the formula (1), when n is 1, It is represented by the following formula,

Any one of said R represents said Z. The method of claim 1, In the formula (1), when n is 2 or more, Compound represented by the following formula.

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An organic electroluminescent device comprising at least one organic layer comprising the compound of claim 1. The method of claim 4, wherein The organic electroluminescent device according to claim 1, wherein the organic layer is formed by a solution process. The method of claim 4, wherein 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 6, The organic material layer is an organic electric element, characterized in that any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. The method of claim 6, The organic material layer includes a light emitting layer, In the light emitting layer, the compound is used as a host or a dopant material. 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 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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