KR101876777B1 - Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof - Google Patents

Abstract

The present invention relates to a compound for an organic electroluminescent device including an indole compound and a derivative thereof, an organic electric device using the organic compound, 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 an organic electroluminescent compound including an indole compound and a derivative thereof,

TECHNICAL FIELD [0001] The present invention relates to a compound for an organic electric device including an Indole 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 .

A conventional liquid crystal display, which is a typical flat display device, can be made lighter than a conventional CRT (cathode ray tube), but has a problem that a viewing angle is limited and a back light is necessarily required. However, an organic light emitting diode (OLED), which is a new flat display device, is a display using self-luminescence phenomenon and has advantages such as a large viewing angle, a light weight and a small size compared to a liquid crystal display, In recent years, application to a full-color display or illumination is expected.

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.

Further, when the HOMO (Highest Occupied Molecular Orbital) energy level difference between the hole transporting layer and the light emitting layer is large, it is difficult to transport holes from the hole transporting layer to the light emitting layer. As a result, holes accumulate at the interface between the hole transporting layer and the light emitting layer There has been a demand for a method of minimizing an energy barrier which becomes a hindrance when holes are transported to the light emitting layer to improve the luminous efficiency.

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 Indole 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, and a terminal thereof.

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 to R ₁₁ 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 ;

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 and C ₂ ~ C ₆₀ aryl amine group of the unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic C ₆ ~ C ₆₀ of;

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 ;

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 aryl silyl 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, and 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 ; Lt;

(2) Ar ₁ is substituted with a hydrogen, deuterium, tritium, a halogen group, an aryl group, a heavy hydrogen of C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the C ₆ ~ an aryl group of C _20, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, a nitrile group, and substituted with an acetylene group a substituent selected from the group consisting or unsubstituted of A C ₁ to C ₅₀ 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 A substituted or unsubstituted C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, substituted or unsubstituted with a substituent selected from the group consisting of an acetylene 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 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 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 ;

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 aryl silyl 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, and 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 ; Lt;

(3) A is a group selected from the group consisting of nitro, nitrile, halogen, silane, 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 consisting of and unsubstituted C ₆ ~ C ₆₀ arylene 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 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 ;

A silane group substituted or unsubstituted with an aryl group having ₆ to ₂₀ carbon atoms ; 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 arylalkenyl group, C ₁ ~ C ₅₀ alkyl group, C ₂ ~ C ₂₀ heterocyclic group, a nitrile group, and an acetylene of the of the substituent is selected from the luer binary group A substituted or unsubstituted divalent aliphatic hydrocarbon group; , ≪ / RTI >

(4) R ₁ to R ₁₁ and Ar ₁ Each may combine with or react with adjacent groups to form a substituted or unsubstituted saturated or unsaturated ring.

In order to achieve the above object, the present invention provides a compound represented by any one of the following formulas (2) to (8).

In the above Chemical Formulas 2 to 8,

(1) R ₁₂ to R ₁₅ 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 ;

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 and C ₂ ~ C ₆₀ aryl amine group of the unsubstituted or substituted with a substituent selected from the group consisting of a heterocyclic C ₆ ~ C ₆₀ of;

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 ;

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 aryl silyl 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 ~ C ₂₀ aryl group, a C ₈ ~ C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C ₂ ~ C ₂₀ substituted or unsubstituted with substituents selected from the group consisting of a heterocyclic C ₆ of an aryl group of ₆₀ ~ C; Lt;

(2) R ₁₂ to R ₁₅ may bond to or react with each other adjacent to each other to form a substituted or unsubstituted saturated or unsaturated ring.

(3) R ₁ to R ₁₁ , Ar ₁ and A are the same as R ₁ to R ₁₁ , Ar ₁ and A 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-mentioned formulas (1) to (8) may be one of the following compounds, but is not limited thereto.

The compounds represented by Chemical Formulas 1 to 8 may be one of the compounds shown above, but are not limited thereto. Since representative substituents of the compounds of formulas (1) to (8) are difficult to illustrate all of the compounds in a wide range, representative compounds are 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.

The use of the indole and its derivatives according to the present invention can greatly improve the luminous efficiency, the low driving voltage, the high heat resistance, the color purity and the life of the device. Therefore, the display device, the organic electroluminescence device (OLED) Organic solar cells, organic photoconductor (OPC), organic transistors (organic TFT), and illumination.

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 compounds among the compounds belonging to the above Chemical Formulas 1 to 8 will be described. However, since there are a large number of compounds belonging to the general formulas (1) to (8), some of them will be exemplarily described. 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

Sub 2-1 + Sub 2-2 Sub 2 "," Sub 3-1 + Sub 3-2 Sub 3-2 Sub 3-2 " 3 "," Sub 4-3 + Sub 3-2 → Sub 4-4 "," Sub 5-3 + Sub 3-2 → Sub 5-4 "," Sub 6-2 + Sub 3-2 → Sub 6 Sub 3-2, Sub 3-2, Sub 7-3, Sub 8-1 + Sub 5-1 Sub 8-2 and Sub 9-1 + Sub 5-1 Sub 9-2 "synthesis methods are all based on the Buchwald-Hartwig cross coupling reaction, among which 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 3 " + 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) "Sub 4-5 + 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) 5-4 + 4,4,4 ', 5,5,5', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) Sub 5 "," Sub 6- 3, 4, 4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) 4,4,4 ', 5,5,5', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) Sub 7 "," Sub 8-2 + 4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) Sub 8 "and" Sub 9-2 + The synthesis of 4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) → Sub 9 "is based on the Miyaura boration reaction. Ishiyama, T., Itoh, Y., Kitano, T., Miyaura, N. Synthesis of 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.

Sub-4-1? Sub 4-2? Naphthalen-2-ylboronic acid + Sub 5-1? Sub 5-2 ?, Phenanthren-9-ylboronic acid + Sub 5? 1 → Sub 6-1 "," Naphthalen-1-ylboronic acid + Sub 5-1 → Sub 7-1 "and" Final process "are all based on the Suzuki cross-coupling reaction. 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.

Sub  1 synthesis method

To 1 equivalent of Sub 1-1 compound, 1.1 equivalents of Sub 1-2 compound, Pd ₂ (dba) ₃ , (t-Bu) ₃ P, NaO t -Bu and toluene are added and the mixture is refluxed for 24 hours. 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 a product. (In the Sub 1 synthesis method, R and A are R ₁ To R & lt; ₁₁ >

Examples of Sub 1-2 include, but are not limited to, the following.

As a result of performing mass spectrometry (HRMS) on the compounds Sub 1-2-1 to Sub 1-2-8, the results are shown in Table 1 below.

In Sub 1-2, A represents 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 hetero ring And a C ₃ to C ₆₀ heteroarylene group substituted or unsubstituted with a substituent selected from the group consisting of an amino group and an amino group.

On the other hand, in the case of Sub 1-2-1 to Sub 1-2-3, the compound shown above as a linking group between Br and I (unsubstituted C ₆ arylene group, unsubstituted C ₁₀ arylene group and unsubstituted in addition to the aryl group) of the C _12, nitro, nitrile, halogen, silane, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, C ₂ ~ heterocycle of the C ₂₀ of the Substituted or unsubstituted < RTI ID = 0.0 > An aryl group of C ₆ to C ₆₀ (provided that an unsubstituted C ₆ arylene group, an unsubstituted C ₁₀ arylene group, and an unsubstituted C ₁₂ arylene group) may also be included.

Further, in the case of Sub 1-2-4 to Sub 1-2-6, the above-mentioned compound (a fluorenylene group substituted with two alkyl groups of C ₁ , two aryl groups of C ₆ are substituted with a linking group between Br and I) the fluorescein in addition to carbonyl group and a C a group of _12, aryl substituted fluorenyl group), hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ - an alkyl group of C ₂₀ aryl group, of a C ₆ - C ₂₀ substituted with a heavy hydrogen aryl, C ₇ - C ₂₀ aryl group, C ₈ - C ₂₀ arylalkenyl group, C ₁ ~ C ₅₀ of, C ₂ ~ the C ₂₀ heterocyclic group, a nitrile group and a substituent selected from the group consisting of acetylene substituted or unsubstituted fluorenyl group (where, A fluorenylene group substituted with two C ₁ alkyl groups, a fluorenylene group substituted with two C ₆ aryl groups, and a fluorenylene group substituted with C ₁₂ aryl groups).

In the case of Sub 1-2-7, in addition to the above-mentioned compound (a divalent aliphatic hydrocarbon group substituted with two aryl groups of C ₆ ) as a linking group between Br and I, hydrogen, deuterium, tritium, ₂ ~ C ₂₀ alkenyl group, an arylalkyl group of C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ substituted by deuterium, C ₈ ~ C ₂₀ arylalkenyl group, C ₁ ~ C ₅₀ alkyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group substituted or unsubstituted divalent aliphatic hydrocarbon group unsubstituted 2 with a substituent selected from the group consisting of group (provided in, A divalent aliphatic hydrocarbon group substituted with two C ₆ aryl groups) may also be included.

In the case of Sub 1-2-8, in addition to the above-mentioned compound (the silane group substituted with two aryl groups of C ₆ ) as a linking group between Br and I, a silane substituted or unsubstituted with a C ₆ to C ₂₀ aryl group Group (except for the silane group substituted with two C ₆ aryl groups).

On the other hand, examples of Sub 1 are as follows, but are not limited thereto.

The compounds Sub 1 (1) to Sub 1 (9) were subjected to mass spectrometry (HRMS).

Sub  2 synthesis method

To 1 equivalent of Sub 1-1 compound, 1.1 equivalents of Sub 1-2 compound, Pd ₂ (dba) ₃ , (t-Bu) ₃ P, NaO t -Bu and toluene are added and the mixture is refluxed for 24 hours. 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 a product. (In the Sub 2 synthesis method, R and A are R ₁ To R & lt; ₁₁ & gt; and A ).

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

As a result of performing mass spectrometry (HRMS) on the compounds Sub 2 (1) to Sub 2 (8), the results are shown in Table 3 below.

Sub  3 Synthetic method

Sub  3-3 Synthetic method

1.1 equivalents of Sub 3-2 compound, Pd ₂ (dba) ₃ , (t-Bu) ₃ P, NaO t -Bu, and toluene are added to 1 equivalent of Sub 3-1 compound and the mixture is refluxed for 24 hours. 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 the product Sub 3-3.

Examples of Sub 3-2 are as follows, but are not limited thereto.

As a result of performing mass spectrometry (HRMS) on the compounds Sub 3-2-1 to Sub 3-2-6, the results are shown in Table 4 below.

In the case of Sub 3-2-1 to Sub 3-2-4 and Sub 3-2-6, when the Br is substituted with the substituted compound (an unsubstituted C ₆ aryl group, an unsubstituted C ₁₀ aryl group, hwandoen aryl group of C ₁₂ aryl group and a C ₄ C ₆ alkyl group is substituted for a) in addition to, hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, A C ₁ to C ₂₀ alkylamine group, a C ₁ to C ₂₀ alkylthiophene group, a C ₆ to C ₂₀ arylthiophene group, a C ₂ to C ₂₀ alkenyl group, a C ₂ to C ₂₀ alkynyl group, an aryl group of C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ of, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, an arylalkenyl group of C ₈ ~ C _20, a silane group, a boron group, a germanium group, and A C ₆ to C ₆₀ aryl group substituted with a substituent selected from the group consisting of C ₂ to C ₂₀ heterocyclic groups, provided that an unsubstituted C ₆ aryl group, an unsubstituted C ₁₀ aryl group, Except for a substituted C ₁₂ aryl group and a C ₄ alkyl group substituted C ₆ aryl group) .

Further, Sub case of 3-2-5, a Br-substituted compounds wherein the (N is 1 included, a heterocyclic group of the unsubstituted C ₅₎ in addition to, hydrogen, deuterium, tritium, a halogen group, C ₁ ~ the alkyl group of C _20, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl amine group, a C ₆ ~ substituted C aryl group, a heavy hydrogen of C _{60 6} ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ heterocyclic group, a nitrile group and acetylene group a substituent selected from the group consisting of and unsubstituted or substituted with , A substituted or unsubstituted C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si, and P (provided that at least one of N is an unsubstituted C ₅ hetero Except for the annulus).

On the other hand, the Ar ₁ of Sub 3-2 are set forth above compound (the alkyl group of the unsubstituted C ₆ aryl group, an unsubstituted C ₁₀ aryl group, an unsubstituted ring of the ring C ₁₂ aryl group, C ₄ substituted C An aryl group having 1 to ₆ carbon atoms, and an unsubstituted C ₅ heterocyclic group containing one N,

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 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, 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;

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, Arylsilyl group; May also be included.

Sub  3 Synthetic method

A round flask was charged with Sub 3-3 (1 equivalent), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) 1.3 equiv) were mixed in _{DMF, PdCl 2 (dppf) (} 0.03 eq), AcOK (3 eq) then were added, then from 130 to reflux the reaction mixture was stirred for 3 hours, MgSO and the organic layer was extracted MC and water ₄ Dried and concentrated, and the resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Examples of Sub 3 include, but are not limited to, the following.

The compounds Sub 3 (1) to Sub 3 (6) were subjected to mass spectrometry (HRMS) as shown in Table 5 below.

Sub  4 Synthetic method

Sub  4-2 Synthesis

Pd (PPh ₃ ) ₄ (0.05 eq.) And NaOH aqueous solution were added to the round flask after mixing with naphthalen-2-ylboronic acid (1 eq.) And Sub 4-1 And the mixture was extracted with MC 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 a product.

Sub  4-3 Synthesis

Subsequently, dichlorobenzene was removed by reduced pressure, and the mixture was extracted with MC and water. Then, the organic layer was washed with MgSO 4 (1 eq.) And dichloropentane ₄ , and the resulting organic material is purified by silicagel column and recrystallized to obtain a product.

Sub  4-4 Synthesis

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) Were added to the corresponding amounts of Sub 4-3 (1 eq.) And Sub 3-2 NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. After extraction with MC and water, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallization to obtain the product.

Sub  4-5 Synthesis

Subsequently, dichlorobenzene was removed by reduced pressure, and the mixture was extracted with MC and water, and the organic layer was washed with MgSO ₄ (1 eq.), Dried and concentrated, and the resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Sub  4 Synthesis

In the round flask, Sub 4-5 (1 equivalent), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane 1.3 equiv) were mixed in _{DMF, PdCl 2 (dppf) (} 0.03 eq), AcOK (3 eq) then were added, then from 130 to reflux the reaction mixture was stirred for 3 hours, MgSO and the organic layer was extracted MC and water ₄ Dried and concentrated, and the resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Examples of Sub 4 are as follows, but are not limited thereto.

As a result of mass spectrometry (HRMS) on the compounds Sub 4 (1) to Sub 4 (6), the results are shown in Table 6 below.

Sub  5 Synthetic method

Sub  5-2 Synthesis

Pd (PPh ₃ ) ₄ (0.05 eq.) And NaOH aqueous solution were added to the round flask in an amount corresponding to naphthalen-2-ylboronic acid (1 equivalent) and Sub 5-1 And the mixture was extracted with MC 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 a product.

Sub  5-3 Synthesis

Subsequently, dichlorobenzene was removed by reduced pressure, and the mixture was extracted with MC and water. Then, the organic layer was washed with MgSO 4 (2 equivalents) and dichlorobenzene ₄ , and the resulting organic material is purified by silicagel column and recrystallized to obtain a product.

Sub  5-4 Synthesis

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) Were added to the round flask after the addition of Sub 5-3 (1 eq.) And Sub 3-2 NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. After extraction with MC and water, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallization to obtain the product.

Sub  5 Synthesis

A round flask was charged with Sub 5-4 (1 equivalent), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) 1.3 equiv) were mixed in _{DMF, PdCl 2 (dppf) (} 0.03 eq), AcOK (3 eq) then were added, then from 130 to reflux the reaction mixture was stirred for 3 hours, MgSO and the organic layer was extracted MC and water ₄ Dried and concentrated, and the resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Examples of Sub 5 include, but are not limited to, the following.

The compounds Sub 5 (1) to Sub 5 (6) were subjected to mass spectrometry (HRMS).

Sub  6 Synthetic method

Sub  6-1 Synthesis

Pd (PPh ₃ ) ₄ (0.05 eq.) And NaOH aqueous solution were added to the round flask in an amount corresponding to phenanthren-9-ylboronic acid (1 eq.) And Sub 5-1 And the mixture was extracted with MC 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 a product.

Sub  6-2 synthesis

Subsequently, dichlorobenzene was removed by reduced pressure, and the mixture was extracted with MC and water. Then, the organic layer was washed with MgSO 4 (1 eq.) And dichloropentane ₄ , and the resulting organic material is purified by silicagel column and recrystallized to obtain a product.

Sub  6-3 synthesis

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) After mixing with the corresponding amount of Sub 6-2 (1 eq.) And Sub 3-2 NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. After extraction with MC and water, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallization to obtain the product.

Sub  6 synthesis

Sub-6-3 (1 equivalent), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) 1.3 equiv) were mixed in _{DMF, PdCl 2 (dppf) (} 0.03 eq), AcOK (3 eq) then were added, then from 130 to reflux the reaction mixture was stirred for 3 hours, MgSO and the organic layer was extracted MC and water ₄ Dried and concentrated, and the resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Examples of Sub 6 include, but are not limited to, the following.

As a result of performing mass spectrometry (HRMS) on the compounds Sub 6 (1) to Sub 6 (6), the results are shown in Table 8 below.

Sub  7 Synthetic method

Sub  7-1 Synthesis

Pd (PPh ₃ ) ₄ (0.05 eq.) And NaOH aqueous solution were added to the round flask after mixing with naphthalen-1-ylboronic acid (1 eq.) And Sub 5-1 And the mixture was extracted with MC 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 a product.

Sub  7-2 synthesis

Subsequently, dichlorobenzene was removed by reduced pressure, and the mixture was extracted with MC and water, and the organic layer was washed with MgSO 4 (1 eq.) And TPP (3 eq.) In a round flask. ₄ , and the resulting organic material is purified by silicagel column and recrystallized to obtain a product.

Sub  7-3 synthesis

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) After mixing with the corresponding amount of Sub 7-2 (1 eq.) And Sub 3-2 NaO t- Bu (3 eq.), Respectively, and the mixture was refluxed at 100 ° C for 8 hours. After extraction with MC and water, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallization to obtain the product.

Sub  7 synthesis

A round flask was charged with Sub 7-3 (1 equivalent), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) 1.3 equiv) were mixed in _{DMF, PdCl 2 (dppf) (} 0.03 eq), AcOK (3 eq) then were added, then from 130 to reflux the reaction mixture was stirred for 3 hours, MgSO and the organic layer was extracted MC and water ₄ Dried and concentrated, and the resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Examples of Sub 7 include, but are not limited to, the following.

As a result of performing mass spectrometry (HRMS) on the compounds Sub 7 (1) to Sub 7 (6), the results are shown in Table 9 below.

Sub  8 Synthetic method

Sub  8-2 synthesis

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) After mixing with the corresponding amount of Sub 8-1 (1 eq.) And Sub 5-1 NaO t -Bu (3 eq.) Was added. The mixture was refluxed at 100 ° C for 8 hours, extracted with MC and water. The organic layer was dried over MgSO ₄ and concentrated. The product is recrystallized.

Sub  8 synthesis

A round flask was charged with Sub 8-2 (1 equivalent), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane 1.3 equivalents) were added to DMF, PdCl ₂ (dppf) (0.03 eq.) And AcOK (3 eq.) Were added. The mixture was refluxed at 130 ° C for 3 hours with MC and water. The organic layer was then washed with MgSO ₄ After drying and concentration, the resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Examples of Sub 8 are as follows, but are not limited thereto.

The compounds 8 (1) to 8 (6) were subjected to mass spectrometry (HRMS). The results are shown in Table 10 below.

Sub  9 Synthetic method

Sub  9-2 synthesis

Pd ₂ (dba) ₃ (0.05 eq.), (T-Bu) ₃ P (0.1 eq.) Were added to the round flask following the addition of Sub 9-1 (1 eq.) And Sub 5-1 NaO t -Bu (3 eq.) Was added. The mixture was refluxed at 100 ° C for 8 hours, extracted with MC and water. The organic layer was dried over MgSO ₄ and concentrated. The product is recrystallized.

Sub  9 synthesis

A round flask was charged with Sub 9-2 (1 equivalent), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane 1.3 equiv) were mixed in _{DMF, PdCl 2 (dppf) (} 0.03 eq), AcOK (3 eq) then were added, then from 130 to reflux the reaction mixture was stirred for 3 hours, MgSO and the organic layer was extracted MC and water ₄ Dried and concentrated, and the resulting organic material is purified by silicagel column and recrystallized to obtain the product.

Examples of Sub 9 include, but are not limited to, the following.

The compounds Sub 9 (1) to Sub 9 (6) were subjected to mass spectrometry (HRMS).

Final compound  Synthetic method

One equivalent of Sub1, Sub4, Sub5, Sub6, Sub7, Sub8, Sub9 derivative of each Sub1 or Sub2 derivative synthesized in the above method was added to THF After mixing, Pd (PPh ₃ ) ₄ (0.03 eq.) And NaOH aqueous solution were added, and the mixture was refluxed at 70 ° C for 12 hours. After the mixture was extracted with MC and water, the organic layer was dried with MgSO ₄ and concentrated. column and recrystallization to obtain the product.

Final compound  Synthetic method example

1-9 Synthetic Examples

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (6.4 g, 20 mmol) and 1- (7-bromo- 9,9-dimethyl-9H-fluoren- 2-yl) -1H-indole (7.8g, 20mmol) after the mixture in _{THF Pd (PPh 3) 4 (} 0.03 eq.), then addition of aqueous NaOH solution, at 70 After 12 hours of stirring and refluxing, the mixture was extracted with MC 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 5.5 g of the product (yield: 55%).

2-4 Synthetic Examples

A solution of 9 - ([1,1'-biphenyl] -4-yl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole Pd (PPh ₃ ) ₄ (0.03 eq.) And NaOH aqueous solution were added to the mixture, and then the mixture was stirred at 70 ° C for 12 hours. After the mixture was stirred under refluxing, the mixture was extracted with MC 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 6.1 g (yield: 60%) of the product.

3-1 Synthetic Example

A round bottom flask was charged with 11-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -11H- 4-bromophenyl) -1H-indole (5.4 g, 20 mmol) was mixed with THF, Pd (PPh ₃ ) ₄ (0.03 eq.) And NaOH aqueous solution were added thereto. The mixture was refluxed at 70 ° C. for 12 hours, After extraction, the organic layer is dried with MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain 6.0 g (yield: 62%) of the product.

4-1 Synthetic Example

A round bottom flask was charged with 11-phenyl-8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -11H- 4-bromophenyl) -1H-indole (5.4 g, 20 mmol) was mixed with THF, Pd (PPh ₃ ) ₄ (0.03 eq.) And NaOH aqueous solution were added thereto. The mixture was refluxed at 70 ° C. for 12 hours, After extraction, the organic layer is dried over MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain 5.8 g (yield: 60%) of the product.

5-8 Synthetic Examples

A round bottom flask was charged with 9-phenyl-12- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-dibenzo [a, - addition of (4'-bromo- [1,1'-biphenyl ] -4-yl) -1H-indole (7.0g, 20mmol) of Pd (PPh _{3) 4} (0.03 equiv.), NaOH solution were mixed in THF After the mixture was stirred at 70 ° C for 12 hours, the mixture was refluxed and extracted with MC 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 7.1 g of the product (yield: 58%).

6-1 Synthetic Example

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -7H-benzo [c] carbazole (8.4 g, 20 mmol) and 1- 4-bromophenyl) -1H-indole (5.4 g, 20 mmol) was mixed with THF, Pd (PPh ₃ ) ₄ (0.03 eq.) And NaOH aqueous solution were added thereto. The mixture was refluxed at 70 ° C. for 12 hours, After extraction, the organic layer is dried over MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain 5.8 g (yield: 60%) of the product.

7-1 Synthetic examples

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole (6.4 g, 20 mmol) and 3- (4-bromophenyl) -3H-benzo [e] indole ( 6.4g, 20mmol) after the mixture in _{THF Pd (PPh 3) 4 (} 0.03 eq.), then added to aqueous NaOH, then stirred for 12 hours under reflux at 70 °, MC and water After extraction, the organic layer is dried over MgSO ₄ and concentrated. The resulting organic material is subjected to silicagel column and recrystallization to obtain 5.6 g (yield: 64%) of the product.

8-1 Synthetic Example

A solution of 7-phenyl-10- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -7H-benzo [c] carbazole (7.4 g, 20 mmol) 4-bromophenyl) -1H-indole (5.4 g, 20 mmol) was mixed with THF, Pd (PPh ₃ ) ₄ (0.03 eq.) And NaOH aqueous solution were added thereto. The mixture was refluxed at 70 ° C. for 12 hours, After extraction, the organic layer is dried over MgSO ₄ and concentrated. The resulting organic material is purified by silicagel column and recrystallized to obtain 5.3 g (yield: 61%) of the product.

Compounds 1-1 to 8-15 finally synthesized were subjected to mass spectrometry (HRMS) and the results are shown in Table 12 below.

Meanwhile, although each of the substituents of the compounds represented by the formulas (1) to (8) is broadly related, examples of synthesis of representative compounds have been exemplarily described, but compounds not exemplarily illustrated in the synthesis examples may also form part of the present specification 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 electronic devices in which the compounds of the invention may be used include, for example, display devices, organic electroluminescent devices (OLEDs), organic solar cells, organophotoreceptor (OPC) drums, organic transistors Devices.

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. The protective layer may be formed to protect the organic layer at the uppermost layer or to protect the cathode, and may be positioned between the hole transporting layer and the light emitting layer in the case of the light emitting auxiliary layer.

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 auxiliary 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 and forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and an electron injecting layer on the anode, ≪ / RTI >

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 emission auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

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.

A light-emitting auxiliary layer may be disposed on the hole transport layer. The light-emission-assisting layer is a layer that prevents light leakage by confining excitons in the light-emitting layer, and the triplet energy band gap of the light-emission-assisting layer is preferably larger than the triplet energy band gap of the light-emitting layer. The light-emission-assisting layer may include a green phosphor or a phosphor when the light-emitting layer emits blue and red light so as to obtain a hue that does not appear in the light-emitting layer, and may include a red phosphor or a phosphor when the light- do.

The organic light emitting layer is disposed on the light emitting auxiliary layer, but if there is no light emitting auxiliary layer, the organic light emitting layer is positioned 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 Manufacture of Organic Electric Device - 1

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention obtained through synthesis as a light emitting auxiliary layer material. First, a film of copper phthalocyanine (hereinafter referred to as CuPc) as a hole injection layer was vacuum deposited on the ITO layer (anode) formed on the glass substrate to form a 70 nm thick film. Subsequently, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as NPD) was vapor-deposited as a hole transport compound on the film to a thickness of 70 nm to form a hole transport layer . Subsequently, the developed material was vacuum-deposited as a light-emission-assisting layer material to a thickness of 25 nm to form a light-emission-assisting layer. (2-phenylpyridine) iridium (hereinafter referred to as " Ir (ppy) ₃ ") as a phosphorescent Ir metal complex dopant after depositing CBP as a phosphorescent host material on the hole transport layer, ≪ / RTI > At this time, the concentration of Ir (ppy) _{3 in} the light emitting layer was 10 wt%. Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 30 nm as an electron transport layer. Then, LiF as an electron injection layer was vapor-deposited to a thickness of 0.5 nm, Al was deposited to a thickness of 120 nm, and the Al / LiF was used as a cathode. Thus, an organic electroluminescent device was fabricated.

Comparative Example  One

An organic electroluminescent device fabricated with the same structure as in the above embodiment without using a light-emission-assisting layer material.

Comparative Example  2

An organic electroluminescent device fabricated with the same structure as that of the above example, except that the compound represented by the above formula was used as a luminescent auxiliary layer.

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 13 below shows device fabrication and evaluation results for the examples and comparative examples to which the compounds according to the invention were applied.

As can be seen from the results of Table 13, the organic electroluminescent device using the material for an organic electroluminescent device of the present invention is not limited to the device (Comparative Example 1) or the Comparative Example 2 It can be seen that the compound can significantly improve the driving voltage, the high luminous efficiency and the lifetime of the device used as the light-emitting auxiliary layer (Comparative Example 2). This is because when the compound of the present invention is used alone as a light emitting auxiliary layer, it has a high T1 energy level and improves the low voltage and device lifetime of the organic electroluminescence device due to the deep HOMO energy level. Further, since the hole is more smoothly transported from the hole transporting layer to the light emitting layer by the light emission assisting layer formed between the hole transporting layer and the light emission assisting layer, the exciton is confined in the light emitting layer to prevent light leakage, It can be implemented.

On the other hand, it can be used not only for an organic electroluminescent device (OLED) but also for a display device, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT) .

Evaluation of Manufacture of Organic Electric Device - 2

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 3 -NPB

For comparison, an organic electroluminescent device having the same structure as the example was fabricated using the compound represented by the above formula (Comparative Example 3 (abbreviated as NBP)) instead of the compound according to the present invention as a hole transport layer material Respectively.

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 14 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 14, the organic electroluminescent device using the material for an organic electroluminescent device of the present invention is used as a hole transporting material and has lower driving voltage, color purity, (OPC), organic transistors (organic TFTs), organic electroluminescent devices (OLEDs) as well as organic electroluminescent devices (OLEDs) as well as display devices, organic solar cells, It can also be used for monochromatic or white illumination devices.

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 hole injecting layer, a light emitting 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 (12)

A compound for an organic electroluminescent device comprising a compound represented by the following formula (1).
≪ Formula 1 >

In Formula 1,
(1) R ₁ to R ₁₁ are each independently of the other hydrogen; 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; And
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 ; ≪ / RTI > and < RTI ID = 0.0 >

(2) Ar ₁ represents hydrogen, deuterium, tritium, a halogen 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 ₆ to C ₂₀ arylamine An aryl group of C ₆ to C ₆₀ substituted with deuterium, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₇ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₂ to C ₂₀ hetero A substituted or unsubstituted C ₂ to C ₆₀ heteroatom which is substituted or unsubstituted with a substituent selected from the group consisting of a halogen group, a nitrile group and an acetylene group and at least one hetero atom selected from O, N, S, Si and P, Ring 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, and 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 > and < RTI ID = 0.0 >
(3) A is a group selected from the group consisting of nitro, nitrile, halogen, silane, 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 consisting of and unsubstituted C ₆ ~ C ₆₀ arylene 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 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;
A silane group substituted or unsubstituted with an aryl group having ₆ to ₂₀ carbon atoms; 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 bivalent aliphatic hydrocarbon group; ≪ / RTI > and < RTI ID = 0.0 >
(4) R ₁ and R ₂ adjacent to each other , R ₅ and R ₆ adjacent to each other, and at least one pair of R ₁₀ and R ₁₁ adjacent to each other may bond or react to form an aromatic ring. delete The method according to claim 1,
Wherein the compound is represented by any one of the following Chemical Formulas (2) to (8).
&Lt; Formula 2 >< EMI ID =

&Lt; Formula 6 &gt;&lt; EMI ID =

In the above Chemical Formulas 2 to 8,
(1) R ₁₂ to R ₁₅ are each independently of the other hydrogen; 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; And
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 ; &Lt; / RTI > and < RTI ID = 0.0 >
(2) R ₁₂ to R ₁₅ may bond or react with each other to form an aromatic ring,
(3) R ₁ to R ₁₁ , Ar ₁ and A are the same as R ₁ to R ₁₁ , Ar ₁ and A defined in the above 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 includes at least one of a light emitting layer, a light emitting auxiliary 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 light-emitting auxiliary layer material. 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; &Lt; / RTI &gt; 12. The method of claim 11,
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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