KR101971877B1 - Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound including an isoindoloindole compound and a derivative thereof, an organic electroluminescent device using the same, and an electronic device using the compound. The present invention can improve the luminous efficiency, color purity and lifetime of the device, .

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for organic electroluminescent devices, an organic electroluminescent device using the same, and an electronic device using the same. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent (EL)

TECHNICAL FIELD [0001] The present invention relates to a compound for an organic electronic device comprising Isoindoloindole and a derivative thereof, an organic electric device including the same, and an electronic device thereof.

Mr. Eastman Kodak of the 1980s. W. C. W. Tang et al. Have made organic electroluminescent devices using organic materials practical by developing laminated structure devices in which various roles are shared among various materials. They emit phosphors capable of transporting electrons and organic materials capable of transporting holes, and both charges are injected into the phosphor layer to emit light, so that a luminance of 1000 cd / m 2 or more can be obtained at a voltage of 10 V or less .

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. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on 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 . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

Particularly, various studies have been conducted on organic materials inserted into a hole transporting layer or a buffer layer for an excellent lifetime characteristic of an organic electric device. To this end, a high hole transporting property from an anode to an organic layer is given, A hole injection layer material having high uniformity and low crystallinity is required.

It is possible to delay penetration and diffusion of the metal oxide from the anode electrode (ITO), which is one of the causes of shortening the lifetime of the organic electronic device, and to stabilize the joule heating caused by driving the device, Lt; RTI ID = 0.0 > layer < / RTI > It is also reported that the low glass transition temperature of the hole transporting layer material significantly affects the lifetime of the device depending on the characteristics of the uniformity of the thin film surface collapsing during device operation. In addition, the deposition method is the mainstream in the formation of OLED devices, and a material that can withstand such a long time, that is, a material having high heat resistance characteristics, is required.

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 a light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. 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 sufficiently exhibit the excellent characteristics of the organic electroluminescent device described above, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material is supported by a stable and efficient material However, stable and efficient development of an organic material layer for an organic electric device has not yet been sufficiently developed, and therefore development of a new material is continuously required.

An object of the present invention is to provide an organic electroluminescent device using an isoindoloindole compound and a derivative thereof, which can improve a high luminous efficiency, a low driving voltage, a high heat resistance, a color purity and a lifetime of the device.

Specifically, the present invention solves the above-mentioned problems of the prior art and provides a light emitting device, a light emitting device, a light emitting device, and a method of manufacturing the same, ≪ / RTI >

In Formula 1,

(1) R ₁ , R ₂ Are each independently of the other hydrogen; heavy hydrogen; Tritium; A halogen group ;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C arylalkyl group of _{7 ~ C 20, C 8 ~} C 20 aryl alkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, the in nitrile group and acetylene group the group consisting of unsubstituted or substituted with substituent C ₁ ~ C ₅₀ An alkyl group;

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and is unsubstituted or substituted with a substituent selected from the group consisting of acetylene, O, N, S, Si , C 2 ~ C ₆₀ heteroaryl rings containing at least one hetero atom of the group P;

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and with a substituent selected from the group consisting of acetylene substituted or unsubstituted C ₂ ~ C ₂₀ alkenyl;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group group substituents a substituted or unsubstituted C ₁ ~ C ₃₀ selected from the consisting of An alkoxy group ; And

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ alkyl group of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ alkyl amine group of the C _20, C ₁ ~ alkyl thiophene group of C _20, C ₆ of ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, a substituted C by deuterium ₆ to C ₂₀ aryl group, a C ₈ - C ₂₀ aryl alkenyl group, a silane group, a boron group, a germanium group, a C ₂ ~ C ₂₀ unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic C ₆ to An aryl group of C ₆₀ ; , ≪ / RTI >

They may be bonded to each other to form a spiro compound.

(2) R ₃ ~ R ₁₀ Are each independently of the other hydrogen; heavy hydrogen; Tritium; A halogen group ;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C arylalkyl group of _{7 ~ C 20, C 8 ~} C 20 aryl alkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, the in nitrile group and acetylene group the group consisting of unsubstituted or substituted with substituent C ₁ ~ C ₅₀ An alkyl group;

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and is unsubstituted or substituted with a substituent selected from the group consisting of acetylene, O, N, S, Si , C 2 ~ C ₆₀ heteroaryl rings containing at least one hetero atom of the group P;

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and with a substituent selected from the group consisting of acetylene substituted or unsubstituted C ₂ ~ C ₂₀ alkenyl;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group group substituents a substituted or unsubstituted C ₁ ~ C ₃₀ selected from the consisting of An alkoxy group ; And

A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ unsubstituted or substituted with a substituent selected from the group yirwojin group heterocyclic C ₆ ~ C ₆₀ arylamine group;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group group substituted with substituted or unsubstituted C ₆ ~ C ₃₀ selected from the consisting of An aryloxy group ; And

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ alkyl group of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ alkyl amine group of the C _20, C ₁ ~ alkyl thiophene group of C _20, C ₆ of ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, a substituted C by deuterium ₆ to C ₂₀ aryl group, a C ₈ - C ₂₀ aryl alkenyl group, a silane group, a boron group, a germanium group, a C ₂ ~ C ₂₀ unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic C ₆ to An aryl group of C ₆₀ ; , ≪ / RTI >

(3) L is a group selected from the group consisting of nitro, nitrile, halogen, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group, a C ₂ to C ₂₀ heterocyclic group, substituted with a substituent selected from the group or unsubstituted arylene group, a C ₆ ~ C _60;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₁ ~ C ₅₀ in the alkyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group substituted or a substituent selected from the group consisting of An unsubstituted fluorenylene group ;

Substituted with a substituent selected from the group consisting of nitro, nitrile, halogen, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group, a C ₂ to C ₂₀ heterocyclic group, Or an unsubstituted C ₃ to C ₆₀ heteroarylene group ; And

A divalent substituted or unsubstituted aliphatic hydrocarbon; , ≪ / RTI >

(4) Ar ₁ , Ar ₂ Are each independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₂₀ alkylamine, C ₁ -C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C of ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl amine , A C ₆ -C ₂₀ aryl group, a C ₆ -C ₂₀ aryl group substituted with deuterium, a C ₈ -C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, a C ₂ -C ₂₀ heterocyclic ring an aryl group unsubstituted or substituted with a substituent selected from the group consisting of a C ₆ ~ C _60;

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and is unsubstituted or substituted with a substituent selected from the group consisting of acetylene, O, N, S, Si , C 2 ~ C ₆₀ heteroaryl rings containing at least one hetero atom of the group P;

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and with a substituent selected from the group consisting of acetylene substituted or unsubstituted C ₂ ~ C ₂₀ alkenyl;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group group substituents a substituted or unsubstituted C ₁ ~ C ₃₀ selected from the consisting of An alkoxy group ;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C arylalkyl group of _{7 ~ C 20, C 8 ~} C 20 aryl alkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, the in nitrile group and acetylene group the group consisting of unsubstituted or substituted with substituent C ₁ ~ C ₅₀ An alkyl group ;

A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ unsubstituted or substituted with a substituent selected from the group yirwojin group heterocyclic C ₆ ~ C ₆₀ arylamine group;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group group substituted with substituted or unsubstituted C ₆ ~ C ₃₀ selected from the consisting of An aryloxy group ; And

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₁ ~ C ₅₀ in the alkyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group substituted or a substituent selected from the group consisting of An unsubstituted fluorene group ; , ≪ / RTI >

(5) R ₁ to R ₁₀ , Ar ₁ and Ar ₂ may react with adjacent groups to form a substituted or unsubstituted saturated or unsaturated ring.

The present invention also provides a compound represented by any one of the following general formulas (2) to (4) to achieve the above object.

In the above Chemical Formulas 2 to 4,

R ₁ to R ₁₀ , Ar ₁ and Ar ₂ are the same as R ₁ to R ₁₀ , Ar ₁ and Ar ₂ defined in the above formula (1).

In the present specification, the term "aryl group" means a single ring or a heterocyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirobifluorene group.

The term "heterocyclic group" refers to an aromatic or alicyclic monocyclic or heterocyclic ring containing a heteroatom in place of the ring forming carbon, and the adjacent substituent is a hetero Aromatic or alicyclic ring.

More specifically, the above Chemical Formulas 1 to 4 may be one of the following compounds, but it is not limited thereto.

The compounds represented by the above Chemical Formulas 1 to 4 may be one of the compounds shown above but are not limited thereto. Since representative substituents of the compounds represented by formulas (1) to (4) are difficult to illustrate all the compounds in a wide range, representative compounds have been exemplarily described, but the compounds represented by formulas (1) to And may constitute a part of this specification.

In another aspect, the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device including the organic electronic device.

By using Isoindoloindole and its derivatives according to the present invention, it is possible to remarkably improve the light emitting efficiency, the low driving voltage, the high heat resistance, the color purity and the lifetime of the device.

1 to 6 show examples of organic electroluminescent devices to which the compounds of the present invention can be applied.

Hereinafter, some embodiments of the present invention will be described in detail with reference to exemplary drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference symbols as possible even if 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 intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. 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."

Hereinafter, preparation examples or synthesis examples of some of the compounds belonging to the general formulas (1) to (4) will be described. However, since the number of compounds belonging to the general formulas (1) to (4) is high, some of them will be exemplarily explained. Those skilled in the art, that is, those skilled in the art, can prepare the compounds belonging to the present invention which are not illustrated through the following production examples.

Typical Synthetic Method Example

Among the general synthesis methods exemplified above, the "Sub 1-3 → Sub 1-4" synthesis method is based on the Miyaura boration reaction. Ishiyama, T., Itoh, Y., Kitano, T., Miyaura, arylboronates via the palladium (0) -catalyzed cross-coupling reaction of tetra (alkoxo) diborons with aryl triflates. Tetrahedron Lett. 1997, 38, 3447-3450. And the like.

In addition, the synthesis method "Sub 1-4 + Sub 1-5 → Sub 1" is based on Suzuki cross-coupling reaction, and Herrmann, WA The Suzuki cross-coupling. Applied Homogeneous Catalysis with Organometallic Compounds (2nd Edition) 2002 , 1, 591-598. And Jones, WD Synthetic chemistry: The key to successful organic synthesis is. Science 2002 , 295, 289-290. And the like.

The synthesis methods of "Ar ₁ -NH ₂ + Br-Ar ₂ → HNAr ₁ Ar ₂ " and "Sub 1 + Sub 2 → Product" are all based on the Buchwald-Hartwig cross coupling reaction. Among them, Hartwig, JF Palladium- catalyzed amination of aryl halides. Mechanism and rational catalyst design. Synlett 1997 , 329-340. And Jiang, L., Buchwald, SL Palladium-catalyzed aromatic carbon-nitrogen bond formation. Metal-Catalyzed Cross-Coupling Reactions (2nd Edition) 2004 , 2, 699-760. And the like.

Sub  1 synthesis method

Sub  1-1 Synthesis

3 ml of THF and NaH (80%, 0.10 g, 2.3 mmol) were added to 5-bromo-1H-indole (0.9 mmol) and the mixture was stirred at 0 ° C. Then, add 1- (bromomethyl) -2-iodobenzene (1.9 mmol) and THF (3 ml) slowly, stir at room temperature for 3 hours, and then add aqueous ammonium chloride. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (2 × 50 mL), and the organic layer was dried with MgSO ₄ and concentrated. Subsequently, the resultant organic material was subjected to silicagel column and recrystallization to obtain Sub 1-1.

Sub  1-2 Synthetic method

Sub 1-1 (0.5 mmol), tetrakis (triphenylphosphine) palladium (0), potassium acetate and dimethylamine obtained in the above synthesis are added and stirred at 160 ° C under nitrogen for 16 hours. Remove the solvent under reduced pressure and add ethyl acetate (50 mL) to the residue. After the reaction was completed, the reaction mixture was extracted with water and ethyl acetate. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain Sub 1-2.

Sub  1-3 Synthetic method

Sub-1-2 in a 250 mL 2-neck round bottom flask and dissolve in DMSO as a solvent. Potassium tert-butoxide and RI were added thereto, followed by stirring at room temperature for 4 hours. After the reaction was completed, 20 mL of water was added, and the mixture was extracted with diethyl ether. The obtained extract was dried with MgSO ₄ and dried under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using ethyl acetate and n-hexane to obtain Sub 1-3.

R in RI is the same as R ₁ and R ₂ described in formula (1), specifically methyl, phenyl and the like. When R is phenyl, a ring can be formed to form a spiro bond.

Sub  1-4 Synthetic methods

After Sub 1-3 obtained in the above synthesis was dissolved in DMF, Bispinacolatodiboron, PdCl ₂ (dppf) catalyst and KOAc were added in order and stirred for 24 hours to synthesize a borate compound. The resulting compound was purified by silicagel column And recrystallized to obtain Sub 1-4.

Sub  1 synthesis method

Sub 1-4 obtained in the above synthesis is dissolved in THF, Sub 1-5, Pd (PPh ₃ ) ₄ , NaOH and water are added, and the mixture is stirred and refluxed. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. Subsequently, the resulting organic material was subjected to silicagel column and recrystallization to obtain Sub 1.

Examples of Sub 1-5 are as follows, but are not limited thereto.

The results of mass spectrometry (HRMS) on the compounds Sub 1-5-1 to Sub 1-5-5 are shown in Table 1 below.

The linking group L of Sub 1-5 may contain bivalent substituted or unsubstituted aliphatic hydrocarbons in addition to the above-mentioned compounds.

On the other hand, in the case of Sub 1-5-1, as the linking group between Br and I, not only the above-mentioned compounds (unsubstituted C ₆ arylene groups) but also nitro, nitrile, halogen, C ₁ to C ₂₀ alkyl groups, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ heterocyclic group and substituted with a substituent selected from the group consisting of an amino group or unsubstituted arylene group, a C ₆ ~ C ₆₀ (where, Except for the unsubstituted C ₆ arylene group).

In the case of Sub 1-5-2, the linking group between Br and I, as well as the above-mentioned compounds (including one N and unsubstituted C ₅ heteroarylene groups) as well as nitro, nitrile, halogen, C ₁ -C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group of C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ heterocyclic group and with a substituent selected from the group consisting of amino group-substituted or unsubstituted C ₃ ~ C ₆₀ of A heteroarylene group (provided that one N is contained and the unsubstituted C ₅ heteroarylene group is excluded).

In the case of Sub 1-5-3 to Sub 1-5-5, the above-mentioned compound (a fluorenylene group substituted with two alkyl groups of C ₁ , a fluorene group substituted with two C ₆ aryl groups) fluorenyl carbonyl group, C of the group of _12, aryl substituted fluorenyl group), as well as hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ substituted with an aryl group, a heavy hydrogen of C ₂₀ C ₆ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ arylalkenyl group of C _20, C ₁ ~ C ₅₀ alkyl group, C ₂ ~ C _A substituted or unsubstituted fluorenylene group (provided that a fluorenylene group substituted with two alkyl groups of C ₁ , and two aryl groups of C ₆ are substituted with a substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, A substituted fluorenyl group, a substituted fluorenyl group, a substituted fluorenyl group, a substituted fluorenyl group, and a fluorenyl group substituted with a C ₁₂ aryl group).

Sub  2 synthesis method

(1 eq.), Bromine compound (1.1 eq.), Pd ₂ (dba) ₃ (0.05 eq.), P (t-Bu) ₃ (0.1 eq.), NaO t- toluene (10.5 mL / 1 mmol) is added and the reaction proceeds at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. Subsequently, the resulting organic material was subjected to silicagel column and recrystallization to obtain Sub 2.

Examples of Sub 2 are as follows, but are not limited thereto.

The results of mass spectrometry (HRMS) on the compounds Sub 2-1 to Sub 2-52 were as shown in Table 2 below.

Sub 2 represents not only the above-mentioned compounds (Sub 2-1 to Sub 2-52) but also Ar ₁ or Ar ₂ ,

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ alkyl group of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ alkyl amine group of the C _20, C ₁ ~ alkyl thiophene group of C _20, C ₆ of ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl amine group, C ₆ ~ C ₂₀ of the aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, a C ₂ ~ C ₂₀ heterocyclic group selected from the group consisting of an aryl group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the substituents;

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and is unsubstituted or substituted with a substituent selected from the group consisting of acetylene, O, N, S, Si , C 2 ~ C ₆₀ heteroaryl rings containing at least one hetero atom of the group P;

Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and A C ₂ -C ₂₀ alkenyl group substituted or unsubstituted with a substituent selected from the group consisting of an acetylene group;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, Substituted or unsubstituted C ₁ -C ₃₀ alkyl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, a nitrile group and an acetylene group, An alkoxy group;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, A substituted or unsubstituted C ₁ -C ₅₀ alkyl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, a nitrile group and an acetylene group, An alkyl group;

A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ unsubstituted or substituted with a substituent selected from the group yirwojin group heterocyclic C ₆ ~ C ₆₀ arylamine group;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₆ -C ₃₀ substituted or unsubstituted aryl groups substituted with a substituent selected from the group consisting of C ₇ -C ₂₀ arylalkyl groups, C ₈ -C ₂₀ arylalkenyl groups, C ₂ -C ₂₀ heterocyclic groups, nitrile groups and acetylene groups, An aryloxy group; And

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₁ ~ C ₅₀ in the alkyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group substituted or a substituent selected from the group consisting of An unsubstituted fluorene group; ≪ / RTI > and the like.

Product  Synthetic method

(1.1 eq.), Sub 2 compound (1 eq.), Pd ₂ (dba) ₃ (0.05 eq.), P (t-Bu) ₃ (0.1 eq.), NaO t -Bu ) and toluene (10.5 mL / 1 mmol), and the reaction is carried out at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was purified by silicagel column and recrystallization.

Product  Synthetic method example

Product  1-34 Synthetic examples

A solution of 2- (4-bromophenyl) -6,6-dimethyl-6H-isoindolo [2,1-a] indole (9.31 g, 24 mmol), dibiphenyl- 4- ylamine (6.42 g, 20 mmol), Pd ₂ (dba) ₃ proceeds to (0.03 ~ 0.05 mmol), P (t-Bu) 3 (0.1 eq.), the reaction at 100 ℃ after loading of NaO t -Bu (3 eq.), toluene (10.5 mL / 1 mmol) . After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 8.55 g (yield: 68%) of the product.

Product  1-40 Synthetic Examples

A solution of 2- (4-bromophenyl) -6,6-dimethyl-6H-isoindolo [2,1-a] indole (9.31 g, 24 mmol), N- (biphenyl- dimethyl-9H-fluoren-2- amine (7.23g, 20mmol), Pd 2 (dba) 3 (0.03 ~ 0.05 mmol), P (t-Bu) 3 (0.1 equiv), NaO t -Bu (3 eq.), toluene (10.5 mL / 1 mmol) is added and the reaction proceeds at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 9.23 g (yield: 69%) of the product.

Product  2-8 Synthetic Examples

2-yl) -6,6-dimethyl-6H-isoindolo [2,1-a] indole (9.34 g, 24 mmol), 4-tert- butyl-N-phenylaniline put _{4.51g, 20mmol), Pd 2 (} dba) 3 (0.03 ~ 0.05 mmol), P (t-Bu) 3 (0.1 equiv), NaO t -Bu (3 eq.), toluene (10.5 mL / 1 mmol) Thereafter, the reaction proceeds at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 6.62 g (yield: 62%) of the product.

Product  2-20 Synthetic Example

2-yl) -6,6-dimethyl-6H-isoindolo [2,1-a] indole (9.34 g, 24 mmol), N1- (naphthalen- N4, N4-diphenylbenzene-1,4- diamine (7.73g, 20mmol), Pd 2 (dba) 3 (0.03 ~ 0.05 mmol), P (t-Bu) 3 (0.1 equiv), NaO t -Bu (3 eq. ) and toluene (10.5 mL / 1 mmol), and the reaction is carried out at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was subjected to silicagel column and recrystallization to obtain 7.34 g (yield: 60%) of the product.

Product  3-1 Synthetic Example

2-yl) -6,6-dimethyl-6H-isoindolo [2,1-a] indole (12.11 g, 24 mmol) in a round bottom flask, Pd ₂ (dba) ₃ (0.03-0.05 mmol), P (t-Bu) ₃ (0.1 eq.), NaO t -Bu (3 eq.), toluene (10.5 mL / And the reaction proceeds at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 6.88 g (yield: 58%) of the product.

Product  3-57 Synthetic Examples

6-dimethyl-8-phenyl-6H-isoindolo [2,1-a] indole (12.21 g, 9.2 mmol) was added to a round bottom flask. Bu ₃ (0.1 eq.), NaO t -Bu (3 eq.), Toluene (10.5 mL), diphenylamine (3.38 g, 20 mmol), Pd ₂ (dba) ₃ (0.03-0.05 mmol) / 1 mmol), and the reaction is allowed to proceed at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.36 g (yield: 55%) of the product.

Compounds 1-1 to 3-60 finally synthesized were subjected to mass spectrometry (HRMS) and the results are shown in Table 3 below.

Meanwhile, although each of the substituents of the compounds represented by the formulas (1) to (4) is broadly related, examples of synthesis of representative compounds have been exemplarily described, but the compounds not exemplarily illustrated in the synthesis examples may also form a part have.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in the production of an organic electronic device including the organic light emitting device into the above structure, Materials can be prepared.

The compounds according to the present invention can be used in various applications in organic electroluminescent devices depending on the kind and nature of substituent groups.

Since the compounds of the present invention are controllable by the core and the substituent, they can act as various layers other than phosphorescent or fluorescent light emitting host hosts.

The organic electroluminescent device of the present invention can be manufactured by a conventional method and material for producing an organic electroluminescent device, except that the above-described compounds are used to form one or more organic substance layers.

It is obvious that the same effects can be obtained even when the compounds of the present invention are used in other organic layers of an organic electroluminescent device, for example, a light-emission assisting layer, an electron injecting layer, an electron transporting layer, and a hole injecting layer.

Meanwhile, the compound of the present invention can be used in a soluble process. That is, the organic compound layer of the organic electronic device described later can be formed by a soluble process of the compound. That is, when the compound is used as an organic material layer, the organic material layer may be formed by a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Lt; RTI ID = 0.0 > a < / RTI > fewer layers.

Organic electric devices in which the compounds of the present invention can be used include, for example, organic electroluminescent devices (OLED), organic solar cells, organic photoconductor (OPC) drums, organic transistors (organic TFT)

The organic electroluminescent device (OLED) will be described as one example of organic electroluminescent devices to which the compounds of the present invention can be applied, but the present invention is not limited thereto and the above-described compounds may be applied to various organic electroluminescent devices.

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode and an organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound of the present invention to provide.

1 to 6 show examples of organic electroluminescent devices to which the compounds of the present invention can be applied.

The organic electroluminescent device according to another embodiment of the present invention can be manufactured by the same method as the organic electroluminescent device except that at least one layer of the organic compound layer including the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, Can be made with a structure known in the art using conventional manufacturing methods and materials in the art.

The structure of an organic electroluminescent device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited to these structures.

1 to 6, an organic electroluminescent device includes substrates 101, 201, 301, 401, 501 and 601, anodes 102, 202, 302, 402, 502 and 602, a hole injection layer 103, Emitting layers 105, 205, 305, 405, 505 and 605, electron transporting layers 106, 206, 406 and 506, an electron injection layer 107, And at least one layer of the organic material layers excluding the light emitting layer may be omitted.

The organic electroluminescent device has a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for blocking the movement of electrons, a luminescent auxiliary layer for assisting or assisting luminescence and a protective layer It may be located. In the case of the protective layer, it may be formed to protect the organic layer at the uppermost layer or to protect the cathode.

At this time, the compound of the present invention may be included in at least one of organic compound layers including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

Specifically, the compound of the present invention may be used as a substitute for one or more of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, May be used. Of course, it can be used for more than two layers, not only one layer of the organic material layer.

In particular, it can be used as a hole injecting material, a hole transporting material, an electron injecting material, an electron transporting material, a light emitting material and a passivation (keping) material according to the compound of the present invention, It can be used as a dopant, and can be used as a hole injecting and hole transporting layer.

For example, the organic electroluminescent device according to another embodiment of the present invention may be formed by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, Oxide or an alloy thereof to form an anode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer on the anode, depositing a material usable as a cathode thereon .

In addition to such a method, the organic material may be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate. The organic material layer may have a multi-layer 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, not by vapor deposition, but by a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, It can be manufactured in a small number of layers.

The organic electroluminescent device according to another embodiment of the present invention may be used in a soluble process such as a spin coating process or an ink jet process.

The substrate may be a silicon wafer, a quartz or glass plate, a metal plate, a plastic film, or a sheet.

An anode is placed on the substrate. Such an anode injects holes into the hole injection layer located thereon. The anode material may be a material having a large work function so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; 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.

A hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are that the hole injection efficiency from the anode is high and the injected holes must be efficiently transported. For this purpose, the ionization potential is small, the transparency to visible light is high, and the stability against holes is excellent.

As the hole injecting material, a hole can be injected from the anode at a low voltage. The highest occupied molecular orbital (HOMO) of the hole injecting material may be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

A hole transport layer is disposed on the hole injection layer. The hole transport layer transports holes from the hole injection layer to an organic light emitting layer disposed thereon, and has high hole mobility, stability to holes, and electrons. In addition to these general requirements, heat resistance to a device is required when it is applied for vehicle display, and it may be a material having a glass transition temperature (Tg) of 70 DEG C or more.

Materials satisfying such conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium oxide Compounds, silicone-based arylamine compounds, and the like.

An organic light emitting layer is disposed on the hole transporting layer. The organic light emitting layer is a layer in which holes and electrons injected from the anode and the cathode respectively recombine to emit light, and the organic light emitting layer is made of a material having high quantum efficiency. The light emitting material may be a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and may be a material having good quantum efficiency for fluorescence or phosphorescence.

Materials or compounds that satisfy these conditions include Alq3 in the case of green, Balq (8-hydroxyquinoline beryllium salt) in the case of blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) biphenyl series, Spiro material, Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenolithium salt ), Bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complexes, imidazoles, thiazole and oxazole metal complexes, and perylene and BczVBi (3,3 ' (1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine). In the case of red, the green luminescent material was doped with DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl- -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile).

Polymers such as a polyphenylene vinylene (PPV) -based polymer and polyfluorene may be used for the organic light emitting layer when the light emitting layer is formed using processes such as inkjet printing, roll coating and spin coating .

An electron transporting layer is disposed on the organic light emitting layer. Such an electron transporting layer requires a material capable of efficiently injecting electrons with a high electron injection efficiency from a cathode disposed thereon. For this purpose, it is required to be made of a material having high electron affinity, high electron transfer rate and excellent stability against electrons.

Specific examples of the electron transporting material satisfying such conditions include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

An electron injection layer is deposited on the electron transport layer. The electron injection layer may be a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI or Tf-6P, boron compounds, and the like. At this time, the electron injection layer may be formed in a thickness range of 100 ANGSTROM to 300 ANGSTROM.

On the electron injection layer, a cathode is positioned. These cathodes serve to inject electrons. The material used for the cathode may be the material used for the anode and may be a metal having a low work function for efficient electron injection. Particularly suitable metals such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or their alloys may be used. Also, an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum, etc., having a thickness of 100 μm or less may be used.

As described above, the compound of the present invention can be used as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are suitable for the fluorescence of all colors such as red, green, It can be used as a host or dopant material of various colors.

The organic electroluminescent device according to the present invention may be of a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

Meanwhile, the present invention includes a display device including the above-described organic electronic device 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 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, and various computers.

Evaluation of manufacturing of organic electric device

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention obtained through synthesis as a hole transport layer. First, 4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (hereinafter referred to as 2T-NATA) was formed on the ITO layer (anode) ) Was formed by vacuum evaporation to a thickness of 10 nm. Then, a compound according to an embodiment of the present invention was vacuum-deposited as a hole transporting compound to a thickness of 30 nm to form a hole transporting layer. After forming a hole transporting layer, a light-emitting layer doped with 7% of BD-052X (Idemitus Co., Ltd.) having a thickness of 45 nm was formed on the top of the hole transport layer. In this case, BD-052X was a blue fluorescent dopant and 9,10- - anthracene (AND)) was used). (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, and then (1,1'- Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm as an electron injecting layer. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and this Al / LiF was used as a cathode. Thus, an organic electroluminescent device was fabricated.

   Comparative Example 1 - NPB Comparative Example 2 Comparative Example 3

For comparison, the compound represented by the above formula (Comparative Example 1 (abbreviated as NBP), Comparative Example 2 and Comparative Example 3) was used in place of the compound according to the example of the present invention as the hole transport layer material, An organic electroluminescent device having the structure shown in FIG.

Electroluminescence (EL) characteristics were measured by PR-650 of a photoresearch company by applying a forward bias DC voltage to the organic electroluminescent devices thus manufactured and the comparative organic electroluminescent devices. The measurement results showed that at a luminance of 300 cd / m 2 The T90 lifetime was measured using a life-time instrument manufactured by McAfee.

Table 4 below shows device fabrication and evaluation results for Examples and Comparative Examples to which the compounds according to the invention were applied.

As can be seen from the results of Table 4, the organic electroluminescent device using the material for an organic electroluminescent device of the present invention was used as a hole transporting material, and Comparative Example 1 (NPB), Comparative Example 2 in which fluorene was substituted, It is possible to remarkably improve the driving voltage, color purity, high luminous efficiency and life span lower than that of the substituted Comparative Example 3. [

It is obvious that the same effects can be obtained even when the compounds of the present invention are used in other organic layers of an organic electroluminescent device, for example, a light emitting layer, a light emitting auxiliary layer, an electron injecting layer and an electron transporting layer.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments.

The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

Claims (11)

1. An organic electroluminescent compound represented by the following formula (1).
≪ Formula 1 >

In Formula 1,
(1) R ₁ and R ₂ are each independently of the other hydrogen; heavy hydrogen; Tritium; A halogen group;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, A substituted or unsubstituted C ₁ -C ₅₀ alkyl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, a nitrile group and an acetylene group, An alkyl group;
Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and is unsubstituted or substituted with a substituent selected from the group consisting of acetylene, O, N, S, Si , C 2 ~ C ₆₀ heteroaryl rings containing at least one hetero atom of the group P;
Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and A C ₂ -C ₂₀ alkenyl group substituted or unsubstituted with a substituent selected from the group consisting of an acetylene group ;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, Substituted or unsubstituted C ₁ -C ₃₀ alkyl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, a nitrile group and an acetylene group, An alkoxy group ; And
Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ alkyl group of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ alkyl amine group of the C _20, C ₁ ~ alkyl thiophene group of C _20, C ₆ of ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, a substituted C by deuterium ₆ to C ₂₀ aryl group, a C ₈ - C ₂₀ aryl alkenyl group, a silane group, a boron group, a germanium group, a C ₂ ~ C ₂₀ unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic C ₆ to An aryl group of C ₆₀ ; , ≪ / RTI >
They may be bonded to each other to form a spiro compound.
(2) R ₃ to R ₁₀ are each independently of the other hydrogen; heavy hydrogen; Tritium; A halogen group;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, A substituted or unsubstituted C ₁ -C ₅₀ alkyl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, a nitrile group and an acetylene group, An alkyl group;
Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and is unsubstituted or substituted with a substituent selected from the group consisting of acetylene, O, N, S, Si , C 2 ~ C ₆₀ heteroaryl rings containing at least one hetero atom of the group P;
Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and A C ₂ -C ₂₀ alkenyl group substituted or unsubstituted with a substituent selected from the group consisting of an acetylene group ;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, Substituted or unsubstituted C ₁ -C ₃₀ alkyl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, a nitrile group and an acetylene group, An alkoxy group ; And
A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ unsubstituted or substituted with a substituent selected from the group yirwojin group heterocyclic C ₆ ~ C ₆₀ arylamine group;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₆ -C ₃₀ substituted or unsubstituted aryl groups substituted with a substituent selected from the group consisting of C ₇ -C ₂₀ arylalkyl groups, C ₈ -C ₂₀ arylalkenyl groups, C ₂ -C ₂₀ heterocyclic groups, nitrile groups and acetylene groups, An aryloxy group; And
Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ alkyl group of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ alkyl amine group of the C _20, C ₁ ~ alkyl thiophene group of C _20, C ₆ of ~ C ₂₀ aryl thiophene group, a C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, a substituted C by deuterium ₆ to C ₂₀ aryl group, a C ₈ - C ₂₀ aryl alkenyl group, a silane group, a boron group, a germanium group, a C ₂ ~ C ₂₀ unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic C ₆ to An aryl group of C ₆₀ ; , ≪ / RTI >
(3) L is a group selected from the group consisting of nitro, nitrile, halogen, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group, a C ₂ to C ₂₀ heterocyclic group, substituted with a substituent selected from the group or unsubstituted arylene group, a C ₆ ~ C _60;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₁ ~ C ₅₀ in the alkyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group substituted or a substituent selected from the group consisting of An unsubstituted fluorenylene group;
Substituted with a substituent selected from the group consisting of nitro, nitrile, halogen, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group, a C ₂ to C ₂₀ heterocyclic group, Or an unsubstituted C ₃ to C ₆₀ heteroarylene group; And
A divalent substituted or unsubstituted aliphatic hydrocarbon; , ≪ / RTI >
(4) Ar ₁ and Ar ₂ each independently represent hydrogen, deuterium, tritium, a halogen group, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₁ to C ₂₀ alkylamine group, alkyl thiophene group of _{C 1 ~ C 20, C 6} ~ C 20 aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C _A C ₆ -C ₂₀ arylamine group, a C ₆ -C ₂₀ aryl group, a C ₆ -C ₂₀ aryl group substituted with deuterium, a C ₈ -C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, A C ₆ to C ₆₀ aryl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₂ to C ₂₀ heterocyclic group ;
Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and is unsubstituted or substituted with a substituent selected from the group consisting of acetylene, O, N, S, Si , C 2 ~ C ₆₀ heteroaryl rings containing at least one hetero atom of the group P;
Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and A C ₂ -C ₂₀ alkenyl group substituted or unsubstituted with a substituent selected from the group consisting of an acetylene group ;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, Substituted or unsubstituted C ₁ -C ₃₀ alkyl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, a nitrile group and an acetylene group, An alkoxy group ;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, A substituted or unsubstituted C ₁ -C ₅₀ alkyl group substituted or unsubstituted with a substituent selected from the group consisting of a C ₇ -C ₂₀ arylalkyl group, a C ₈ -C ₂₀ arylalkenyl group, a C ₂ -C ₂₀ heterocyclic group, a nitrile group and an acetylene group, An alkyl group ;
A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ unsubstituted or substituted with a substituent selected from the group yirwojin group heterocyclic C ₆ ~ C ₆₀ arylamine group;
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₆ -C ₃₀ substituted or unsubstituted aryl groups substituted with a substituent selected from the group consisting of C ₇ -C ₂₀ arylalkyl groups, C ₈ -C ₂₀ arylalkenyl groups, C ₂ -C ₂₀ heterocyclic groups, nitrile groups and acetylene groups, An aryloxy group; And
Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₁ ~ C ₅₀ in the alkyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group substituted or a substituent selected from the group consisting of An unsubstituted fluorene group ; , ≪ / RTI >
(5) R ₁ to R ₁₀ , Ar ₁ and Ar ₂ may react with adjacent groups to form a substituted or unsubstituted saturated or unsaturated ring. The method according to claim 1,
remind R ₁ to R ₁₀ , Ar ₁ and Ar ₂ are bonded to or react with each other to form a saturated or unsaturated ring. The method according to claim 1,
Wherein the compound is represented by any one of the following Chemical Formulas 2 and 3:
(2)

(3)

In the general formulas (2) and (3), R ₁ to R ₁₀ , Ar ₁ and Ar ₂ are the same as defined in the general formula (1). The method according to claim 1,
A compound for an organic electroluminescent device, characterized in that it is one of the following compounds.

An organic electroluminescent device comprising at least one organic layer comprising the compound of claim 1. 6. The method of claim 5,
Wherein said compound is formed into said organic material layer by a solution process. 6. The method of claim 5,
An organic electroluminescent device comprising a first electrode, an organic material layer and a second electrode sequentially laminated. 6. The method of claim 5,
Wherein the organic material layer comprises at least one of a light emitting layer, a hole injecting layer, a hole transporting layer, an electron injecting layer, and an electron transporting layer. 9. The method of claim 8,
Wherein the compound is used as the hole transport layer material. A display device comprising the organic electroluminescent device of claim 5; And
A controller for driving the display device; ≪ / RTI > 11. The method of claim 10,
Wherein the organic electronic device is one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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