TW201305106A - Compound for organic electronic element, organic electronic element using the same, and electronic device thereof - Google Patents

Abstract

Disclosed is an organic electronic element including the compound or the composition as a material for a hole injection layer or a hole transport layer. By using a material including deuterium, with a high driving characteristic and a long life span, it is possible to reduce a driving voltage, and increase a luminous efficiency and a device life span in an organic electro-luminescence element.

Description

a compound for an organic electronic component, an organic electronic component using the same, Electronic device

The present invention relates to a compound or composition for use in an organic electronic component, an organic electronic component containing the same or the composition, and an electronic device thereof, wherein the compound or the composition requires only a low driving voltage and can improve luminescence Efficiency and device life.

A flat panel display component plays a very important role in supporting the advanced image information community that has recently grown primarily in the Internet space. In particular, an organic electro-luminescence element can be driven at a low voltage in a self-emissive mode compared to a liquid crystal display (LCD) (the most widely used flat panel display element). Excellent performance in contrast. Further, since the organic electroluminescence element does not require a backlight, it can be manufactured in a light weight and a thin thickness. In addition, it is advantageous in terms of power consumption. In addition, due to its high response speed and wide color reproduction range, it has attracted attention as a display device of the next generation. In general, an organic electroluminescent device has an anode including a transparent electrode, an organic material layer including a light-emitting region, and a metal electrode (cathode) which are sequentially formed on a glass substrate.

Here, the organic material layer may include not only an emission layer (EML) but also a hole injection layer (HIL), a hole transport layer (HTL), and an electron transport layer ( Electron Transport Layer (ETL) or Electron Injection Layer (EIL). For light emission of the light-emitting layer, it may further comprise an electron blocking layer (EBL) or a hole blocking layer (HBL). When an electric field is applied to the organic electroluminescent element having the structure, a hole is injected from the anode, and electrons are injected from the cathode. The injected holes and electrons are respectively transmitted from the hole transport layer and the electron transport layer, and are recombined with the light emitting layer to form luminescent excitons. When illuminating, the formed luminescent excitons are Change to the ground state. Here, in order to improve the efficiency and stability of the light emission state, a luminescent pigment (guest) may be incorporated in the light-emitting layer (body). In order to utilize this organic electroluminescent element in various display media, the life of the device is of the utmost importance. At present, much research has been conducted on the improvement of the life of organic electroluminescent elements. In particular, in order to achieve a long life of an organic electronic component, much research has been conducted on the introduction of an organic material into a hole transport layer or a buffer layer. For this reason, it is necessary to develop a hole injection layer material which can increase the mobility of the hole from the anode to the organic layer, and the hole injection layer material has high uniformity and low crystallinity during formation of the film after deposition.

Further, there is a need to develop a hole injection layer material which can delay the penetration/diffusion of metal oxide from an anode electrode (ITO) to an organic layer (one of the causes of a decrease in the life of an organic electronic component), and operates for a device The resulting Joule heating property is that the high glass transition temperature has a phase-resistant stability. Moreover, it has been reported that the low glass transition temperature of the hole transport layer material has a high efficiency in the life of the device in which the uniformity of the film surface is deteriorated according to the operation of the device. Further, in the formation of the organic light emitting diode device, a deposition method is mainly used. Therefore, there is a need to develop a highly heat resistant material that can withstand for a long time in the deposition method.

In particular, among the currently used organic light-emitting elements, it is an urgent problem to be solved in increasing the power consumption and life of a panel size such as a mobile phone or a tablet computer.

However, it is difficult to solve the problem by using the drive voltage and lifetime of the hole transport layer material. This is because the material has high hole transmission capability, that is, high hole mobility, which is used to lower the driving voltage, mainly a planar structure rich in electrons (for example, naphthalene, anthracene, phenanthrene, etc.). When the amount of the compounds reaches a predetermined amount, a compound having the above structure (as a substituent) is introduced into the hole transporting material to increase hole mobility and have a good influence on the life. However, in the case of increasing the amount of such compounds introduced into the molecule in order to achieve the low voltage driving currently required by the industry, when the life characteristics are rapidly degraded, the driving voltage is reduced, thereby allowing low voltage driving to be achieved. This is because in the case where the molecule excessively introduces a planar structure having a rich electron, when a predetermined current is continuously supplied during the life test of the device, the hole is trapped between the sheet structure and the stability, thereby reducing the hole mobility. . Therefore, in order to apply a predetermined amount of current, the driving voltage is increased, resulting in a rapid decline in the life of the device. This is expressed by the following equation:

J = space charge limiting current

ε = dielectric constant

μ = mobility factor

θ = charge trap coefficient (free carrier / total carrier)

V = voltage

d = thickness

When the number of free carriers is reduced by the trap phenomenon, the value of θ is reduced. Therefore, in the case where the current-driven organic electroluminescence element requires a predetermined amount of current, the driving voltage is increased. This can lead to a very fatal result over the life. In other words, as described above, the introduction of the sheet-like structure has an adverse effect on the life, the sheet-like structure having rich electrons for increasing the mobility of the holes larger than a predetermined number. Therefore, the possibility of lowering the driving voltage by such introduction is small.

An object of the present invention is to provide a compound or composition, an organic electronic component containing the same or the composition, and an electronic device thereof, wherein the compound or the composition can achieve high luminous efficiency and low driving voltage of a device, and Can increase color purity and longevity.

In order to achieve this, a compound represented by the following structural formula 1 is provided: <Structure 1>

According to another aspect of the present invention, there is provided a composition comprising a mixture having the compound represented by the above structural formula 1 and a compound represented by the following structural formula 2:

According to another aspect of the present invention, there is provided a composition for an organic electronic component comprising a composition having a mixture comprising two or more different compounds derived from the compound represented by the above structural formula 1. Here, at least one of the different two or more kinds of compounds may be a deuterium-containing compound, and the different two or more kinds of compounds may be contained in any one of the compounds equal to or less than 90. The wt% of the composition (relative to the total weight of the composition) is mixed.

According to still another aspect of the present invention, there is provided an organic electronic component using the compound represented by Structural Formula 1.

According to still another aspect of the present invention, there is provided an organic electronic component utilizing a composition having a mixture comprising two different or more A plurality of kinds of compounds are derived from the compound represented by the above structural formula 1, or/and the organic electronic component has a mixture comprising a compound represented by the above structural formula 1 and the compound represented by the above structural formula 2 by a composition. Here, at least one compound constituting the composition may be a compound substituted with one oxime, and may be mixed at 90 or less.

According to still another aspect of the present invention, an electronic device includes: a display device including an organic electronic component; and a control unit that drives the display device, wherein the organic electronic component comprises: the above structure a compound represented by Formula 1, a composition having a mixture of two or more kinds of compounds different from the compound represented by the above Structural Formula 1, or/and a compound represented by the above Structural Formula 1 and the above structure A composition of a mixture of compounds represented by Formula 2.

When the compound of the present invention and/or the composition is used, it is possible to achieve an increase in luminous efficiency, low driving voltage, high color purity, and longevity in a device.

Exemplary embodiments of the present invention will be described below with reference to the drawings.

In the following description, although the same elements are shown in different drawings, the same elements will be denoted by the same reference numerals. Further, in the following description of the present invention, the detailed description of known functions and configurations incorporated herein may be omitted.

Further, when describing elements of the present invention, terms such as first, second, A, B, (a), (b), and the like may be used. Each of these terms is not used to define the nature, order, or order of the corresponding elements, and is only used to distinguish the corresponding elements from other elements. It is noted that if an element is "connected", "coupled" or "coupled" to another element in the specification, the third element can be "connected", "coupled" and "coupled" in the first Between the second elements, the first element may be directly connected, coupled or coupled to the second element.

In this specification, the so-called "halo" or "halogen" is included Fluorine, chlorine, bromine and iodine.

In the present invention, the term "alkane" or "alkyl group" has 1 to 60 carbon atoms unless otherwise defined, but the present invention is not limited thereto.

In the present invention, the "alkenyl group" or "alkynyl group" referred to has a double bond or a triple bond of 2 to 60 carbon atoms unless specifically defined, but the present invention is not limited thereto.

In the present invention, the term "cycloalkyl" as used herein means an alkyl group having a ring having 3 to 60 carbon atoms, unless otherwise defined, but the invention is not limited thereto.

In the present invention, the term "alkoxy group" has 1 to 60 carbon atoms unless otherwise defined, but the present invention is not limited thereto.

In the present invention, the "aryl group" and the "extended aryl group" each have 6 to 60 carbon atoms unless otherwise defined, but the present invention is not limited thereto.

In the present specification, the term "heteroalkyl" means an alkyl group having one or more hetero atoms unless otherwise defined.

In the present invention, the term "heteroaryl" or "heteroaryl" as used herein means a C ₃ -C ₆₀ aryl or aryl group having one or more hetero atoms, unless otherwise defined. The invention is not limited thereto.

In the present invention, the term "heterocycloalkyl" or "heterocyclic group" includes one or more hetero atoms and has 2 to 60 carbon atoms unless otherwise defined.

In the present specification, the term "hetero atom" means nitrogen, oxygen, sulfur, phosphorus or antimony.

The term "aliphatic" as used in the present invention means an aliphatic hydrocarbon having 1 to 60 carbon atoms, unless otherwise defined, and the term "alicyclic" as used in the present invention means having 3 to An alicyclic hydrocarbon of 60 carbon atoms.

The other hetero compound or the other hetero atom of the above hetero compound contains one or more hetero atoms, but the invention is not limited thereto. In addition, unless otherwise defined, "substituted or unsubstituted" as used in the present invention means that the substitution is substituted with at least one substituent selected from the group consisting of an anthracene, a halogen, an amine group, Nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thienyl group, C ₆ ~ C ₂₀ aryl thienyl, C ₂ ~ C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl, C ₆ ~ C ₆₀ aryl, C ₆ ~ C ₂₀ a group consisting of an aryl group substituted with a C ₈ -C ₂₀ aralkenyl group, a decyl group, a boron group, a fluorenyl group and a C ₅ -C ₂₀ heterocyclic group, but the invention is not limited thereto Substituent.

In the method of the present invention, a material having an excellent lifetime is used, and a sheet-like molecular structure having an adverse effect on the life is not introduced, so that the driving voltage can be reduced. A method of reducing the driving voltage by substituting a suitable ratio of ruthenium or by substituting a compound having a similar structure of ruthenium is provided.

It was found that the compound substituted by hydrazine showed better thermodynamic behavior than the unsubstituted compound. In view of this thermodynamic property, for example, it has been found that high luminescence efficiency can be achieved due to the difference in bond length between carbon-hydrogen and carbon-ruthenium when ruthenium is substituted for ruthenium compound. This is because in compounds containing carbon and ruthenium (having a small bond length), the van der Waals force between the molecules is reduced by the smaller bond length.

In addition, it was found that when hydrazine is substituted for a compound, the zero point energy (i.e., the ground state energy) is lowered, and at the same time, the bond length of the ruthenium-carbon is shortened. Therefore, the molecular hard core volume is reduced, thereby reducing the electron polarizability. This weakens the interaction between the molecules, thus increasing the volume of the film. Due to this property, it may lower the crystallinity of the film. In other words, the amorphous state of the film can be achieved. Therefore, judging this characteristic will be very effective for achieving an amorphous state required for increasing the lifetime of the organic light-emitting diode (OLED) and the popularization of driving characteristics.

However, methods for reducing the driving voltage and increasing the mobility of holes through the holes replaced by germanium have not been fully studied. In the present study, in order to confirm such properties, many experiments were carried out by using various compounds. It has been found that when a film is formed through a composition of a compound having a structure substituted by a similar oxime, an amorphous glass state having a considerable effect on the hole mobility of the film can be achieved. Therefore, this method is very advantageous. Further, it has been found that such an amorphous glass state can reduce the grain boundary by the isotropic and homogeneous characteristics, thereby increasing the flow of charges (i.e., hole mobility).

For further description of the invention, the use of an oxazole-containing amine compound is included as a material for increasing the lifetime. In particular, according to the present study, the carbazolylamine compound was found to have excellent command properties, but increased the driving voltage. However, in the conventional art, the effect of improving such disadvantages has not been proven. In particular, a technique of replacing driving characteristics at a specific position to improve driving characteristics has not been reported.

Through the research and development of the present inventors, the present invention provides a compound having an amine group substituted with hydrazine, which can maintain the above-described excellent characteristics of the organic material layer of the organic electronic component and satisfy the demand of the organic material.

In particular, among the compounds of the examples of the present invention, in the case of linking a carbazole and an arylamine by an aryl group or the like, ruthenium may be introduced into an aryl group bonded to an amine group, thereby improving organic electroluminescence. Device characteristics of the component. For example, in a structure in which an amine group is bonded to biphenyl, it may be introduced into a phenyl group at the end of biphenyl, hydrazine (rather than hydrogen), allowing the organic material layer to be deposited more stably, and improving interface characteristics. Moreover, it is quite easy to accurately control a band gap. Therefore, it is possible to manufacture an organic electronic component having excellent characteristics of an organic electronic component.

Although ruthenium is introduced into the aryl group between the amine group and the terminal aryl group, it is possible to produce an organic electronic component having excellent device characteristics. However, in the aryl group attached to the amine group, when hydrazine is introduced into the terminal aryl group, for example, a terminal phenyl group, it is possible to produce a more excellent device. Also, in the aryl group in which the end of the aryl group attached to the amine group is introduced, for example, a phenyl group, when all of the carbon atoms (except for the substituents bonded to other substituents) are replaced by deuterium (not hydrogen), It is possible to create a more superior device.

The present invention provides a compound represented by the following structural formula 1: In Structural Formula 1, (1) Ar ₁ and Ar _{3 are} each independently the same or different and are selected from the group consisting of C ₆ to C ₆₀ aryl groups which are subjected to at least one substituent. Substituted or unsubstituted, and the substituent is selected from the group consisting of hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, C ₁ ~C ₂₀ alkylamino group, C ₁ ~ C ₂₀ alkyl thienyl group, C ₆ ~ C ₂₀ aryl thienyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ to C ₂₀ cycloalkyl, C ₆ to C ₆₀ aryl, C ₆ to C ₂₀ substituted aryl, C ₈ to C ₂₀ aralkenyl, C ₆ to C ₂₀ arylamine a group consisting of a decyl group, a boron group, a fluorenyl group, and a heterocyclic group of C ₃ to C _{20 ;} a heterocyclic group of C ₂ to C ₆₀ substituted or unsubstituted with at least one substituent, and the substitution The base is selected from the group consisting of hydrogen, hydrazine, halogen, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ arylamine , C ₆ ~ C ₆₀ aryl, C substituted C ₆ ~ C ₂₀ aryl, C ₇ ~ C ₂₀ aralkyl, C ₈ ~ C ₂₀ aralkenyl, C ₃ ~ C ₂₀ miscellaneous Group of cyclic groups, nitrile groups and alkynyl groups And a group comprising at least one of oxygen, nitrogen and sulfur; a C ₁ -C ₃₀ alkoxy group substituted or unsubstituted with at least one substituent selected from hydrogen and hydrazine , halo, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₃ -C ₃₀ cycloalkyl a C ₂ -C ₃₀ heterocycloalkyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₂₀ aryl group substituted by hydrazine, and a C ₂ -C ₂₀ heterocyclic group; C ₆ -C ₃₀ An aryloxy group substituted or unsubstituted with at least one substituent selected from the group consisting of hydrogen, anthracene, halo, an amine group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, C ₂ -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, fluorene a substituted C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heterocyclic group; a C ₆ -C ₆₀ arylamine group substituted or unsubstituted with at least one substituent, and the substituent is selected from the group consisting of halo, amino, nitrile, nitro, C ₁ ~ C ₂₀ alkyl group of, C ₂ ~ C ₂₀ alkenyl group of, C ₁ ~ C ₂₀ of alkoxy, cycloalkyl of C ₃ ~ C ₃₀ alkyl group, C ₂ ~ C ₃₀ Heterocycloalkyl, C ₆ ~ C ₆₀ aryl group and the C ₂ ~ C ₂₀ of the heterocyclyl group; and C ₁ ~ C ₅₀ alkyl group of which is substituted by one substituent or unsubstituted, and the substituent is It is selected from the group consisting of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ aryl, 氘C ₆ ~C ₂₀ a group consisting of an aryl group, a C ₇ -C ₂₀ aralkyl group, a C ₈ -C ₂₀ aralkenyl group, a C ₃ -C ₂₀ heterocyclic group, a nitrile group and an alkynyl group, wherein Ar ₁ to Ar At least one of ₃ contains at least one hydrazine, (2) R ₁ and R _{2 are} each independently the same or different, and are selected from the group consisting of hydrogen; hydrazine; halogen; nitro; nitrile; amine a C ₆ -C ₆₀ aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thienyl group, C ₆ ~ C ₂₀ aryl thienyl group, C ₂ ~ C ₂₀ alkenyl group of, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group of, C ₆ ~ C ₆₀ of the aryl group, C ₆ ~ C ₂₀ of deuterium substituted with the aryl group, C ₈ ~ C ₂₀ a group consisting of an aralkenyl group, a C ₆ -C ₂₀ arylamine group, a decyl group, a boron group, a fluorenyl group, and a C ₃ -C ₂₀ heterocyclic group; a heterocyclic group of C ₂ to C ₆₀ ; Substituted or unsubstituted with at least one substituent selected from hydrogen, hydrazine, halo, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ ~C ₂₀ Alkoxy group, C ₆ ~ C ₂₀ arylamine group, C ₆ ~ C ₆₀ aryl group, 氘 substituted C ₆ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ aralkyl group, C ₈ ~ a group consisting of C ₂₀ aralkenyl groups, C ₃ -C ₂₀ heterocyclic groups, nitrile groups and alkynyl groups, and comprising at least one of oxygen, nitrogen and sulfur; C ₁ to C ₃₀ alkoxy groups, Substituted or unsubstituted with at least one substituent selected from hydrogen, hydrazine, halo, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₂ ~C ₂₀ Alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, C ₂ -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, oxime substituted C ₆ the ~ C ₂₀ aryl group and C ₂ ~ C ₂₀ of the heterocyclyl group; C ₆ ~ C ₃₀ aryloxy group of which at least one substituent by a substituted or unsubstituted, and the substituent is selected from the group consisting of hydrogen, deuterium Halo, amino, nitrile, nitro, C ₁ ~ C ₂₀ alkyl group of, C ₂ ~ C ₂₀ alkenyl group, the alkoxy group of C ₁ ~ C _20, a cycloalkyl group of C ₃ ~ C _30, a heterocycloalkyl group of C ₂ to C ₃₀ , an aryl group of C ₆ to C ₆₀ , an aryl group of C ₆ to C ₂₀ substituted with hydrazine, and a heterocyclic group of C ₂ to C ₂₀ ; and C ₁ to C ₅₀ An alkyl group substituted or unsubstituted with a substituent selected from the group consisting of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy , C ₆ ~ C ₂₀ aryl, C substituted C ₆ ~ C ₂₀ aryl, C ₇ ~ C ₂₀ aralkyl, C ₈ ~ C ₂₀ aralkenyl, C ₃ ~ C ₂₀ miscellaneous a group consisting of a cyclic group, a nitrile group and an alkynyl group, wherein each of R ₁ and R ₂ may be bonded to an adjacent group to form an alicyclic compound, an aromatic compound or a heterocyclic compound, and (3) L represents a C ₆ -C ₆₀ exoaryl group substituted or unsubstituted with at least one substituent selected from the group consisting of a nitro group, a nitrile group, a halogen group, an alkyl group, an alkoxy group, an amine group, the group consisting of an aryl group and a heterocyclic group; or a C ₂ ~ C ₆₀ heterocycloalkyl group of which is unsubstituted or substituted with at least one substituent, and the substituent is selected from And a group consisting of a nitro group, a nitrile group, a halogen group, an alkyl group, an alkoxy group, an amine group, and an aryl group, and (4) a represents an integer of 0 to 4, and b represents an integer of 0 to 3. c represents an integer from 0 to 2.

In another aspect, the present invention provides a composition having a mixture comprising two or more different compounds derived from the compound represented by Structural Formula 1 above. Here, two or more different kinds of compounds may be mixed in such a manner that either compound is contained in a composition equal to or less than 90% by weight based on the total weight of the composition.

In still another aspect, the present invention provides a composition for an organic electronic component, comprising a mixture comprising the compound represented by the above structural formula 1 and a compound represented by the following structural formula 2, wherein the two compounds may be any A compound is mixed in a manner equal to or less than 90% by weight of the composition (relative to the total weight of the composition): [Structure 2] In formula 2, ₍₁₎ Ar 1 to Ar ₃ is the same as the above formula 1 wherein Ar ₁ to Ar ₃ of such substituents are defined, (2) R ₁ to R ₄ are identical to the formula 1 The definition of such substituents in R ₁ or R ₂ , wherein each of R ₁ to R ₄ may be bonded to an adjacent group to form an alicyclic compound, an aromatic compound or a heterocyclic compound, (3) R' And R" are each independently the same or different and are C ₆ -C ₆₀ aryl groups which are substituted or unsubstituted with at least one substituent selected from hydrogen, hydrazine, halogen, amine a group, a nitrile group, a nitro group, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₁ -C ₂₀ alkylamino group, a C ₁ -C ₂₀ alkylthiophenyl group, C ₆ ~ C ₂₀ aryl thienyl, C ₂ ~ C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl, C ₆ ~ C ₆₀ aryl, hydrazine substituted The C ₂ -C ₂₀ aryl group, the C ₈ -C ₂₀ aralkenyl group, the C ₆ -C ₂₀ arylamine group, the decyl group, the boron group, the fluorenyl group and the C ₃ -C ₂₀ heterocyclic group Or a C ₁ -C ₅₀ alkyl group substituted or unsubstituted with at least one substituent, and the substituent is selected from C ₁ to C ₂₀ alkyl, C ₂ ~ C ₂₀ alkenyl, C ₁ ~ C ₂₀ alkoxy, C ₆ ~ C ₂₀ aryl, hydrazine substituted C ₂ ~ C ₂₀ aryl, C ₇ ~ C _a group consisting of ₂₀ aralkyl groups, C ₈ -C ₂₀ aralkenyl groups, C ₃ -C ₂₀ heterocyclic groups, nitrile groups and alkynyl groups, wherein R' and R" may be bonded to each other to form an alicyclic ring a compound, an aromatic compound, a heterocyclic compound or a spiro compound, and (4) a represents an integer of 1 to 3, and each of b, c, and d represents an integer of 1 to 4.

More specifically, in the above structural formula 1, Ar ₂ may be represented by the following structural formula: In the above formula, (1) R ₃ and R ₄ are each independently the same or different and are selected from the group consisting of halogen; nitro; nitrile; amine; C ₆ to C An aryl group of ₆₀ which is substituted or unsubstituted with at least one substituent selected from the group consisting of hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₁ ~ C ₂₀ alkoxy, C ₁ ~ C ₂₀ alkyl amine, C ₁ ~ C ₂₀ alkyl thienyl, C ₆ ~ C ₂₀ aryl thienyl, C ₂ ~ C ₂₀ alkene a group, a C ₂ ~ C ₂₀ alkynyl group, a C ₃ ~ C ₂₀ cycloalkyl group, a C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C ₂₀取代 substituted aryl group, C ₈ ~ C ₂₀ of the aromatic a group consisting of an alkenyl group, a C ₆ -C ₂₀ arylamino group, a decyl group, a boron group, a fluorenyl group, and a C ₃ -C ₂₀ heterocyclic group; a C ₂ -C ₆₀ heterocyclic group having at least a substituent substituted or unsubstituted, and the substituent is selected from the group consisting of hydrogen, hydrazine, halogen, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ ~C ₂₀ alkane An oxy group, an arylamine group of C ₆ to C ₂₀ , an aryl group of C ₆ to C ₆₀ , an aryl group of C ₆ to C ₂₀ substituted by hydrazine, an aralkyl group of C ₈ to C ₂₀ , C ₈ to C ₂₀ Aromatic alkenyl, C _a group consisting of ₃ to C ₂₀ heterocyclic groups, nitrile groups and alkynyl groups, and comprising at least one of oxygen, nitrogen and sulfur; a C ₁ -C ₃₀ alkoxy group substituted by at least one substituent or Unsubstituted, and the substituent is selected from the group consisting of hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ ~C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C ₃₀ heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 氘 substituted C ₆ ~ C ₂₀ aryl group and C _a heterocyclic group of ₂ to C ₂₀ ; an aryloxy group of C ₆ to C ₃₀ which is substituted or unsubstituted with at least one substituent selected from hydrogen, hydrazine, a halogen group, an amine group, Nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C ₃₀ a heterocycloalkyl group, an aryl group of C ₆ -C ₆₀ , a C ₆ -C ₂₀ aryl group substituted by hydrazine, and a C ₂ -C ₂₀ heterocyclic group; and a C ₁ -C ₅₀ alkyl group, The substituent is substituted or unsubstituted, and the substituent is selected from the group consisting of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ Aryl The composition of generations of C ₆ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ aralkyl group of, C ₈ ~ C ₂₀ alkenyl group of aryl, C ₃ ~ C ₂₀ heterocyclic group, the nitrile group, and alkynyl group a group, wherein each of R ₃ and R ₄ may be bonded to an adjacent group to form an alicyclic compound, an aromatic compound or a heterocyclic compound, and (2) R′ and R′′ are each independently the same or different, And is an aryl group of C ₆ -C ₆₀ substituted or unsubstituted with at least one substituent selected from hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thienyl group, C ₆ ~ C ₂₀ aryl thienyl group, C ₂ to C ₂₀ alkenyl group, C ₂ to C ₂₀ alkynyl group, C ₃ to C ₂₀ cycloalkyl group, C ₆ to C ₆₀ aryl group, oxime substituted C ₆ to C ₂₀ aryl group, C _a group consisting of ₈ to C ₂₀ aralkenyl groups, C ₆ to C ₂₀ arylamine groups, decyl groups, boron groups, sulfhydryl groups and C ₃ to C ₂₀ heterocyclic groups; or C ₁ to C ₅₀ An alkyl group substituted or unsubstituted with at least one substituent selected from the group consisting of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkane The substituted group, the C ₆ ~ C ₂₀ aryl group, C ₆ ~ C ₂₀ deuterium of the aryl group, C ₇ ~ C ₂₀ aralkyl group of, C ₈ ~ C ₂₀ alkenyl group of aryl, C ₃ ~ C ₂₀ a group consisting of a heterocyclic group, a nitrile group and an alkynyl group, wherein R' and R" may be bonded to each other to form an alicyclic compound, an aromatic compound, a heterocyclic compound or a spiro compound, and (3) e represents Is an integer from 1 to 4, d represents an integer from 1 to 3, and (4) Ar ₃ contains at least one oxime.

In the above structural formula 1, at least one of Ar ₁ , Ar ₂ and Ar ₃ may be selected from the group consisting of the compounds of the following structural formula 3: [Structure 3] In the above structural formula 3, D represents 氘, a represents an integer of 1 to 5, a' represents an integer of 1 to 7, b represents an integer of 0 to 4, and b' represents an integer of 0 to 6, c , c', h, j, m, p, s, t, u, s', t', and u' each represent an integer from 0 to 5, and d, e, f, g, and l each represent 0 to 4 The integers, i and k each represent an integer from 0 to 2, and n, o, q, r, q' and r' each represent an integer from 0 to 3. Here, the numbers may be determined in such a manner that at least one of Ar ₁ to Ar ₃ may include 氘.

In the structural formulas listed in Structural Formula 3, for example, when the range is from 0 to 5, Corresponding to the following structural formula: In the same way, this principle is applied to other structural formulas.

More specifically, in Ar ₁ to Ar ₃ of the above structural formulas 1 and 2, Ar ₁ to Ar ₃ contain fluorene, which may be represented by the following structural formula, but the present invention is not limited thereto:

More specifically, the compound represented by Structural Formula 1 may be any of the following P-1 to P-132 compounds, but the present invention is not limited thereto: [Structure 5]

The compound represented by the above structural formula 1 may be any one of the compounds listed in Structural Formula 5, but the present invention is not limited thereto. Here, since the compound represented by each structural formula 1 has a wide variety of substituents, it is actually difficult to exemplify all the compounds. Therefore, the only representative compound is exemplified. However, it should be noted that other compounds represented by Structural Formula 1, although not exemplified in Structural Formula 5, may form part of this specification.

More specifically, the compound represented by the above structural formula 2 may be any one of the following P2-1 to P2-120 compounds, but the present invention is not limited thereto: [Structure 6]

The compound represented by the above Structural Formula 2 may be any one of the compounds listed in Structural Formula 6, but the present invention is not limited thereto. Here, since the compound represented by each structural formula 2 has a wide range of substituents, it is actually difficult to exemplify all the compounds. Therefore, the only representative compound is exemplified. However, it should be noted that other compounds represented by Structural Formula 2, although not exemplified in Structural Formula 6, may form part of this specification.

Meanwhile, a compound having the structural formula or a composition containing a mixture of the compounds can be used in a dissolving procedure. In other words, an organic material layer of an organic electronic component can be formed by a dissolution procedure of a compound or a composition containing a mixture of the compounds, which will be described later. In other words, when using each The composition or each composition as an organic material layer can be used by a dissolving procedure or a solvent procedure instead of deposition (for example, spin coating, dip coating, knife coating, screen printing, inkjet printing or The various polymeric materials of the method of thermal transfer) and the layer of organic material are fabricated in fewer layers.

In another aspect, an organic electronic component is provided comprising a first electrode, a second electrode, and at least one organic material layer comprising the compound of Structural Formula 1. Here, the organic material layer may comprise a composition having a mixture comprising two or more different compounds derived from the compound represented by the above structural formula 1, or a composite having a mixture comprising the above structural formula. A compound represented by 1 and a compound represented by the above structural formula 2. The organic material layer may include at least one of a light emitting layer, a hole injection layer, and a hole transport layer.

The organic electronic component of the present invention may be any one of an organic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor (organic thin film transistor), and a monochromatic or white light illuminating device.

As described below, the composition of the present invention can achieve the maximum characteristics of the organic material layer of the organic electronic component when the material of the hole injection layer is required (i.e., high uniformity and low crystallinity during film formation). . Furthermore, it can satisfy other needs of the material of the hole injection layer, such as delaying the permeation/diffusion of the metal oxide from the anode electrode to the organic layer (one of the causes of the decrease in lifetime), and the Joule heating property caused by the device driving. (that is, high glass transition temperature) the stability of the phase resistance, and can meet the demand of high heat-resistant materials, that is, in the formation of organic electroluminescent elements, against the materials required for long-term deposition methods.

As described above, the inventors have found that a composition containing a mixture of ruthenium-substituted compounds exhibits better thermodynamic behavior than a compound which is not substituted by a ruthenium or osmium substituted compound. Further, it has been found that a high bond efficiency can be achieved because of a small bond length in a compound containing carbon and ruthenium due to a difference in bond length between carbon-hydrogen and carbon-ruthenium. This is because the Van der Waals force between the molecules is reduced by the smaller bond length. In addition, it was found that when hydrazine is substituted for a compound, the zero point energy (i.e., the ground state energy) is lowered, and at the same time, the bond length of the ruthenium-carbon is shortened. Therefore, the molecular hard core volume is reduced, thereby reducing the electron polarizability. This weakens the interaction between the molecules Acting, thus increasing the volume of the film.

Due to this property of the compound of the invention substituted by hydrazine, it may lower the crystallinity of the film. In other words, the amorphous state of the film can be achieved. Therefore, it is judged that this characteristic is very effective for realizing the realization of the amorphous state required for increasing the lifetime of the organic electroluminescence element and the popularization of the driving characteristics.

As a result, the mixture of compounds substituted with hydrazine exhibits lower visible light absorption than the carbon-hydrogen bonded material. It is judged that in a light-emitting device such as an organic electroluminescence element, this property can be advantageous for improving efficiency. Further, the mixture of the compounds substituted by the hydrazine of the present invention is determined to greatly improve the heat resistance.

Preparation example:

Preparation examples or synthetic examples on the compound of Structural Formula 1 or Structural Formula 2 will be described below. However, since there are many compounds represented by Structural Formula 1 or Structural Formula 2, some compounds will be listed among the compounds. Without the enumerated compounds, those skilled in the art will appreciate that other compounds can be prepared by the following preparative examples.

General synthetic methods:

The general synthetic method of the invention is as follows:

i) General synthetic method for compounds of structural formula 1

Ii) a general synthetic method for the compound of structural formula 2

(To simplify the illustration, the reactants or terms used in the synthesis methods herein and below will be directly represented by the English original name or the English acronym in the field. For example, toluene will be represented by toluene, the method will be represented by method, and the final product will be Expressed as final product or product, the example will be represented by example, the intermediate will be Intermediate indicates that pyridine will be represented by pyridine, starting material will be represented by starting material, comparative example will be represented by comp.example, compound will be represented by compound, and so on; the above English or abbreviations are detailed in each synthesis method. The corresponding Chinese name is mentioned in the synthetic text description)

Synthesis of Compounds of Structural Formula 1

1) Example of Sub 1 synthesis method: (Ar ₁ , L = phenyl)

Sub 1-1: Synthesis of 9-phenyl-9H-carbazole

Mix carbazole (50.2 g, 300 mmol) and bromobenzene (56.5 g, 360 mmol) with 2800 mL of toluene and add Pd ₂ (dba) ₃ (8.24 g, 9 mmol), PPh ₃ (7.87 g) 30 mmol) and NaOt-Bu (86.5 g, 900 mmol) were stirred at 100 ° C for 24 hours under reflux. The resulting product was extracted with diethyl ether and water and dried over MgSO ₄ Successively, the resulting organic material was purified and recrystallized from a silica gel column to provide 52.5 g of product (75%).

Sub 1-2: Synthesis of 3-bromo-9-phenyl-9H-carbazole

Sub-1-1 (48.66 g, 200 mmol) obtained via the above synthesis was dissolved in 600 mL of dichloromethane, and NBS was slowly added. (N-bromosuccimide, N-bromosuccinimide) (59.4 g, 210 mmol), followed by stirring at room temperature for 24 hours.

After completion of the reaction, 300 mL of HCl (5% concentration) was added to the resulting product. 300 mL of water was added thereto to remove the remaining NBS. Then, the resulting product was extracted with diethyl ether and water, dried over MgSO ₄ and evaporated. The resulting organic material was purified by silica gel short column and recrystallized to afford 47.7 g of product (74%).

Synthesis of Sub 1-3: 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-9H-carbazole

Sub 1-2 (45.1 g, 140 mmol) obtained by the above synthesis was dissolved in 980 mL of DMF, and bisquinalol borate (39.1 g, 154 mmol), PdCl ₂ (dppf) was sequentially added. The catalyst (3.43 g, 4.2 mmol) and KOAc (41.3 g, 420 mmol) were stirred for 24 hours to synthesize the monoborate compound. The obtained compound was purified by silica gel short column and recrystallized to give 35.2 g of a borate compound (68%).

Synthesis of Sub 1:3-(4-bromophenylhydrazine)-9-phenyl-9H-carbazole

Sub 1-3 (29.5 g, 80 mmol) obtained by the above-mentioned synthesis was dissolved in 360 mL of tetrahydrofuran, and 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh ₃ ) 4 was added. (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water. After completion of the reaction, the resulting product was extracted with diethyl ether and water. Dried over MgSO ₄ and the organic layer was concentrated. The resulting organic material was purified by silica gel short column and recrystallized to afford 22.9 g of product (72%).

2) Examples of R ₁ -substituted synthesis methods: (Ar ₁ , R ₁ , L = phenyl)

Sub 1-1-1: Synthesis of 3,9-diphenyl-9H-carbazole

Sub 1-2 (25.8 g, 80 mmol) obtained in the above Example 1 was dissolved in 360 mL of tetrahydrofuran, then phenylboronic acid (10.7 g, 88 mmol), Pd(PPh ₃ ) 4 (2.8 g, 2.4 mmol) NaOH (9.6 g, 240 mmol) and 180 mL of water were prepared as a 18.9 g product (74%) by an exemplary sub 1 synthesis. In an amplification reaction, the same yield was achieved by the same experimental method.

Synthesis of Sub 1-2: 3-Bromo-6,9-diphenyl-9H-carbazole

600 mL of dichloromethane and NBS (N-bromosuccimide, N-bromosuccinimide) (59.4 g, 210 mmol) were obtained by the above synthesis by the sub 1-2 synthesis method of Example 1. Sub 1-1-1 (63.88 g, 200 mmol) was prepared as 55.8 g of product (70%).

Synthesis of Sub 1-3:3,9-Diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-9H-carbazole

Pass 980 mL of DMF, bisphosphonate borate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol) and KOAc (41.3 g, 420 mmol) through sub 1 of Example 1. 3 Synthesis method, 40.5 g of a product (65%) was prepared from Sub-1-2 (55.8 g, 140 mmol) obtained by the above-mentioned synthesis.

Synthesis of Sub 1:3-(4-bromophenylhydrazine)-6,9-diphenyl-9H-carbazole

Sub-1-3 (35.6 g, 80 mmol) obtained through the above-mentioned synthesis was dissolved in 360 mL of tetrahydrofuran, and 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd (PPh ₃ ) was added. ₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and 180 mL of water, followed by reflux stirring. After completion of the reaction, the resulting product was extracted with diethyl ether and water. Dried over MgSO ₄ and the organic layer was concentrated. The resulting organic material was purified by silica gel short column and recrystallized to afford 27.7 g of product (73%).

3) Examples of synthetic methods for starting materials containing dibenzothiophene

Synthesis of Intermediate A

2-Bromophenylmethyl sulfide was dissolved in glacial acetic acid solvent, and the resulting solution was cooled to 0 ° C, and then hydrogen peroxide was slowly dropped thereinto. After the dropwise addition was terminated, the solution was warmed to room temperature, and stirred for 12 hours. After the reaction was completed, the solvent was removed using a pressure reducing device. Then, the resulting product was extracted with CH ₂ Cl _{2 and} the resulting product was washed with aqueous NaHCO ₃ . Over anhydrous MgSO ₄ to remove a small amount of water. After vacuum filtration, the organic solvent was concentrated, and the obtained product was purified by column chromatography to afford 43 g of the desired intermediate A (yield: 98%).

Synthesis of Intermediate B

Together with the Intermediate A 2-Bromo-carbazole, Pd (PPh _{3) 4} and Na ₂ CO ₃ was dissolved in anhydrous tetrahydrofuran and a small amount of water, the splice reflux for 24 hours. After completion of the reaction, the resulting product was cooled to room temperature, the resulting product was extracted with CH ₂ Cl ₂ and the product formed was washed with water. Over anhydrous MgSO ₄ to remove a small amount of water. After vacuum filtration, the organic solvent was concentrated, and the product was purified by column chromatography to afford 30.6 g of the desired intermediate B (yield: 51%).

Synthesis of Intermediate C

Intermediate B obtained by the above synthesis was carried out by 300 mL of dichloromethane and NBS (Nbromosuccimide, N-bromosuccinimide) (29.7 g, 105 mmol) by the sub 1-2 synthesis method of Example 1. (30.5 g, 100 mmol) was prepared as 28.058 g of product (73%).

Synthesis of intermediate D

Intermediate C was dissolved in trifluoromethanesulfonic acid solvent and stirred at room temperature for 48 hours. After completion of the reaction, a solvent of a water-pyridine mixture was added to the resulting solution, followed by reflux for 20 minutes. The resulting product was cooled to room temperature, and the resulting product was extracted with CH ₂ Cl ₂ and washed with water. A small amount of water was removed with MgSO ₄ . After vacuum filtration, the organic solvent was concentrated and purified to purified crystalljjjjjjjjjj

Synthesis of starting materials

Intermediate D (21.1 g, 60 mmol), iodobenzene (18.4 g, 90 mmol), DMF 300 mL, K ₂ CO ₃ (12.4 g, 90 mmol), copper powder (4.2 g, 66 mmol) and 18- Crown-6 (1.6 g, 6 mmol) was charged to a round bottom flask and refluxed at 170 ° C for 24 hours. After completion of the reaction, the resulting product was extracted with water and CH ₂ Cl ₂ and washed with 5% aqueous HCl. Finally, wash with salt water. The obtained organic layer was dried over MgSO ₄ . After vacuum filtration, the organic solvent was concentrated and the product was purified by column chromatography to afford 19 g of desired starting material (74%).

4) Examples of the synthesis of 3-cyano-9-phenylcarbazole

Synthesis of Intermediate A

DMF (43.4 mL) was loaded into a round bottom flask and placed under a nitrogen atmosphere. The reaction temperature was adjusted to 0 °C. Then, phosphonium chloride was slowly dropped thereinto, and the resultant was warmed to room temperature, followed by stirring for 1 hour. The reaction temperature was adjusted again to 0 °C.

Then, a solution of 9-phenylcarbazole dissolved in 1,2-chloroethane (52 mL) was added dropwise thereto for 1 hour.

The mixture was stirred at a reaction temperature of 90 ° C for 8 hours. After completion of the reaction, the resulting product was extracted with ice water and CH ₂ Cl ₂ . Dried over MgSO _4, and purified by column chromatography using ethanol and hexane to obtain the organic layer was recrystallized to provide 31.4 g of the aldehyde 3- -9-phenyl carbazole (Intermediate A, 75%) of Compound.

Synthesis of Intermediate B

3-aldehyde-9-phenylcarbazole (31.4 g, 116 mmol), hydroxylamine hydrochloride (10 g, 140.4 mmol), acetic acid (25.1 g, 418 mmol), pyridine (16.72 g, 209 mmol) obtained from the above synthesis. And DMF (83 mL) were sequentially charged into a reaction flask and stirred at 140 ° C for 5 hours. After completion of the reaction, the resulting product was extracted with water and CH ₂ Cl ₂ . Dried over MgSO _4, and purified by column chromatography using ethanol and hexane to obtain the organic layer was recrystallized, to provide 23 g of 3-cyano-9-phenyl-carbazole (Intermediate B, 74%) Compound.

Synthesis of Intermediate C

The intermediate B obtained by the above synthesis was obtained by the sub 1-2 synthesis method of Example 1 using 80 mL of dichloromethane and NBS (Nbromosuccimide, N-bromosuccinimide) (25.46 g, 90 mmol). 23 g, 85.72 mmol) was prepared as 20.54 g of product (69%).

5) Examples of Sub 2 synthesis methods

Aniline-d5 (23.56 g, 240 mmol) and bromobenzene-d5 (32.41 g, 200 mmol) were mixed into a flask, and Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g) was added. 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL) were stirred under reflux for 24 hours. After completion of the reaction, the resulting product was extracted with diethyl ether and water. Dried over MgSO ₄ and the organic layer was concentrated. The resulting organic material was purified by silica gel short column and recrystallized to afford 26.17 g of product (73%).

Synthesis of Sub 2-2

26.14 g of the product (68%) was obtained in the same manner as described in the synthesis of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 1-bromo-4-fluorobenzene was used. (35 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-3

26.14 g of the product (75%) was obtained in the same manner as described in the synthesis of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), bromobenzene (31.4 g, 200 mmol) was used. ), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-4

41.24 g of the product (71%) was obtained in the same manner as described in the synthesis of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 2-bromo-9,9- was used. Dimethyl-9H-indole (54.6 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh3 (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-5

57.2 g of the product (69%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that aniline-d5 (23.56 g, 240 mmol), 2-bromo-9,9- was used. Diphenyl-9H-indole (79.5 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and Toluene (1930 mL).

Synthesis of Sub 2-6

57.2 g of the product (69%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that aniline-d5 (23.56 g, 240 mmol), 2-bromo-9,9- was used. Diphenyl-9H-indole (79.5 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and Toluene (1930 mL).

Synthesis of Sub 2-7

44.5 g of the product (74%) was obtained in the same manner as described in the synthesis of Sub 2-1, except that 1-naphthylamine (34.37 g, 240 mmol), 4'-bromo-2 was used. 3,4,5,6-d5-biphenyl (47.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g , 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-8

32.3 g of the product (72%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol) and 2-bromonaphthalene (41.41 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-9

36.55 g of the product (73%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 4-bromobiphenyl (46.62 g) was used. , 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-10

41.46 g of the product (69%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 1-(4-bromophenyl) was used. Naphthalene (56.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL) .

Synthesis of Sub 2-11

40.86 g of the product (68%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 2-(4-bromophenyl) was used. Naphthalene (56.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL) .

Synthesis of Sub 2-12

39.05 g of the product (65%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that aniline-d5 (23.56 g, 240 mmol), 1-bromo-4-phenyl group was used. Naphthalene (56.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-13

39.05 g of the product (65%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 2-bromo-6-phenyl group was used. Naphthalene (56.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-14

44.4 g of the product (68%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that aniline-d5 (23.56 g, 240 mmol) and 3,5-diphenyl bromide were used. Benzene (61.84 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-15

45.76 g of the product (67%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 4-bromo-N, N- was used. Diphenylaniline (64.84 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930) mL).

Synthesis of Sub 2-16

39.82 g of the product (71%) was obtained in the same manner as described in the synthesis of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 2-bromo-dibenzothiophene was used. (52.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-17

37 g of the product (70%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that aniline-d5 (23.56 g, 240 mmol), 2-bromo-dibenzofuran was used. (49.42 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-18

34.24 g of the product (74%) was obtained in the same manner as described in the synthesis of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol) and 1-bromonaphthalene-d7 (42.82) were used. g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-19

33.32 g of the product (72%) was obtained in the same manner as described in the synthesis of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol) and 2-bromonaphthalene-d7 (42.82) were used. g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-20

36.77 g of the product (72%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that aniline-d5 (23.56 g, 240 mmol) and 4'-bromo-2,3 were used. , 4,5,6-d5-biphenyl (47.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-21

43.04 g of the product (70%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that aniline-d5 (23.56 g, 240 mmol), 1-(4-bromobenzene) was used. -2,3,4,5,6,7,8-d7-naphthalene (58.04 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

43.23 g of the product (71%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol) and 2-(4-bromo-2) were used. , 3,5,6-d4-phenyl)naphthalene (57.44 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

42.15 g of the product (69%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 1-bromo-4-(2) was used. ,3,4,5,6-d5-phenyl)naphthalene (57.64 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-24

42.15 g of the product (69%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that aniline-d5 (23.56 g, 240 mmol), 2-bromo-6-(2) was used. ,3,4,5,6-d5-phenyl)naphthalene (57.64 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2-25

43.07 g of the product (64%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that aniline-d5 (23.56 g, 240 mmol), 3,6-diphenyl- D10-bromobenzene (63.85 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930) mL).

Synthesis of Sub 2-26

45.08 g of the product (68%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that 4-phenyl-d5-aniline (41.82 g, 240 mmol), 4'- was used. Bromo-2,3,4,5,6-d5-biphenyl (47.63 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt- Bu (57.7 g, 600 mmol) and toluene (1930 mL).

6) Examples of Sub 3 synthesis methods

Synthesis of Sub 3-1

30.92 g of the product (67%) was obtained in the same manner as described in the synthesis method of Sub 2-1 except that Sub 2-7 (30.04 g, 100 mmol), 2,5-dibromothiophene was used. (26.61 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Synthesis of Sub 3-2

33.80 g of the product (63%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that N-(2,3,5,6-d4-biphenyl-4-yl group was used. Naphthyl-1-amine (29.94 g, 100 mmol), 2-bromo-5-(4-iodophenyl)thiophene (40.15 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Synthesis of Sub 3-3

31.68 g of the product (65%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that double (2', 3', 4', 5', 6'-d5- was used. Biphenyl-4-yl)amine (33.15 g, 100 mmol), 2,6-dibromopyridine (26.06 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g) , 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Synthesis of Sub 3-4

34.19 g of the product (69%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that N-benzene-d5-naphthalen-1-amine (22.43 g, 100 mmol) was used. 2,7-Dibromo-9,9-dimethylhydrazine (38.73 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Synthesis of Sub 3-5

41.51 g of the product (67%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that N-benzene-d5-naphthalen-2-amine (22.43 g, 100 mmol) was used. 2,7-Dibromo-9,9-diphenylfluorene (52.38 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Synthesis of Sub 3-6

38.02 g of the product (67%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that Sub 2-3 (17.43 g, 100 mmol), 2,7-dibromo- 9,9'-spirobis[芴] (52.16 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 Methyl) and toluene (970 mL).

Synthesis of Sub 3-7

29.53 g of the product (66%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that Sub 2-2 (19.22 g, 100 mmol), 2,7-dibromophenanthrene was used. (36.96 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Synthesis of Sub 3-8

27.97 g of the product (69%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that Sub 2-3 (17.43 g, 100 mmol), 4,4'-dibromo was used. Biphenyl (34.32 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL) .

Synthesis of Sub 3-9

26.17 g of the product (69%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that Sub 2-3 (17.43 g, 100 mmol), 2,6-dibromonaphthalene was used. (31.46 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Synthesis of Sub 3-10

25.79 g of the product (68%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that Sub 2-3 (17.43 g, 100 mmol), 1,4-dibromonaphthalene was used. (31.46 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Synthesis of Sub 3-11

25.41 g of the product (67%) was obtained in the same manner as described in the synthesis method of Sub 2-1, except that Sub 2-3 (17.43 g, 100 mmol), 1,5-dibromonaphthalene was used. (31.46 g, 110 mmol), Pd ₂ (dba) ₃ (2.75 g, 3 mmol), PPh ₃ (2.63 g, 10 mmol), NaOt-Bu (28.9 g, 300 mmol) and toluene (970 mL).

Method for synthesizing the final product

Method 1 synthesis method

In a round bottom flask, Sub 1 (1 equivalent), Sub 2 (1 equivalent), Pd ₂ (dba) ₃ (0.05 mol%), PPh ₃ (0.1 equivalent), NaOt-Bu (3 equivalents) and Toluene (10.5 mL / 1 mmol) was reacted at 100 °C. After completion of the reaction, the resulting product was extracted with diethyl ether and water. Dried over MgSO ₄ and the organic layer was concentrated. The resulting organic material is purified by a silica gel short column and recrystallized to provide a product.

Method 2 synthesis method

In a round bottom flask, fill in Sub 1-3 (1 eq.), Sub 3 (1.1 eq.), Pd (PPh ₃ ) ₄ (0.05 eq.), NaOH (3 eq.), tetrahydrofuran (3 mL / 1 mmol) And water (1.5 mL / 1 mmol).

Then, the mixture was heated under reflux at 80 ° C to 90 ° C. After the completion of the reaction, the resulting product was diluted with distilled water at room temperature. Then, the product was extracted with dichloromethane and water. Dried over MgSO ₄ and the organic layer was concentrated. The resulting compound is purified by a short column of silica gel and recrystallized to provide a product.

Structural analysis of a final synthetic compound was performed by HRMS (mass spectrometry) as described below. Further, the purity was measured by HPLC (using tetrahydrofuran as a flow washing solvent) manufactured by Shimatzu.

Synthesis of Compound of Structure 2

1) Example of Sub 1b synthesis method:

Synthesis of Sub 1b-1

Filled with aniline-d5 (19.63 g, 200 mmol), bromobenzene (37.68 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt- Bu (57.7 g, 600 mmol) and toluene (1930 mL) were stirred under reflux for 24 hours. After completion of the reaction, the obtained product was extracted with diethyl ether and water, dried over MgSO ₄ and concentrated. The column was purified and the crystallized organic material was recrystallized to afford 26.14 g of product (75%).

Synthesis of Sub 1b-2

32.3 g of the product (72%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that aniline-d5 (19.63 g, 200 mmol) and 1-bromonaphthalene (49.70 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 1b-3

32.3 g of the product (72%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that aniline-d5 (19.63 g, 200 mmol) and 2-bromonaphthalene (49.70 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 1b-4

36.55 g of the product (73%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that aniline-d5 (19.63 g, 200 mmol), 4-bromobiphenyl (55.94 g) was used. , 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 1b-5

35.89 g of the product (70%) was obtained in the same manner as described in the synthesis method of Sub 1b-1, except that aniline-d5 (19.63 g, 200 mmol), 2-bromo-5-phenylthiophene was used. (57.39 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 1b-6

29.42 g of the product (72%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that aniline-d5 (19.63 g, 200 mmol), 1-bromo-4-methoxy Benzobenzene (44.89 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL) .

Synthesis of Sub 1b-7

35.95 g of the product (68%) was obtained in the same manner as described in the synthesis method of Sub 1b-1, except that aniline-d5 (19.63 g, 200 mmol), 2-bromodibenzo[b] was used. , d] furan (59.30 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930) mL).

Synthesis of Sub 1b-8

23.84 g of the product (62%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that aniline-d5 (19.63 g, 200 mmol), 1-bromo-4-fluorobenzene was used. (42 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 1b-9

26.30 g of the product (66%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that aniline-d5 (19.63 g, 200 mmol) and 4-bromobenzonitrile (43.68) were used. g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

2) Example of the synthesis method of Sub 2b:

Synthesis of Sub 2b-1

55.13 g of the product (68%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that phenylaniline-d5 (34.85 g, 200 mmol), 4-bromo-4' was used. -Iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930) mL).

Synthesis of Sub 2b-2

62.85 g of the product (69%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that N-phenyl-d5-naphthalen-1-amine (44.86 g, 200 mmol) was used. 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2b-3

61.93 g of the product (68%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that N-phenyl-d5-naphthalen-2-amine (44.86 g, 200 mmol) was used. 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2b-4

65.48 g of the product (68%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that N-phenyl-d5-biphenyl-4-amine (50.07 g, 200 mmol) was used. ), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g) , 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2b-5

63.37 g of the product (65%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that N-phenyl-d5-phenylthiophene-2-amine (51.28 g, 200 mmol) was used. ), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g) , 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2b-6

59.21 g of the product (68%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that N-(4-methoxyphenyl)-aniline-2,3,4 was used. 5,6-d5 (40.86 g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g) , 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2b-7

64.40 g of the product (65%) was obtained in the same manner as described in the synthesis method of Sub 1b-1, except that N-phenyl-d5-dibenzo[b,d]furan-2- was used. Amine (52.87 g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol) NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2b-8

56.73 g of the product (67%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that N-phenyl-d5-4-fluorophenyl-1-amine (38.45 g, 200 mmol), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu ( 57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 2b-9

59.39 g of the product (69%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 4-(phenyl-d5-amine) benzonitrile (39.85 g, 200 mmol) was used. ), 4-bromo-4'-iodobiphenyl (86.16 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g) , 600 mmol) and toluene (1930 mL).

3) Example of Sub 3b synthesis method:

Synthesis of Sub 3b-1

38.81 g of the product (68%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that aniline (18.63 g, 200 mmol), 2-bromo-9,9-dimethyl was used. -9H-oxime (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene ( 1930 mL).

Synthesis of Sub 3b-2

45.62 g of the product (68%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that naphthalen-2-amine (28.64 g, 200 mmol), 2-bromo-9 was used. 9-Dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol And toluene (1930 mL).

Synthesis of Sub 3b-3

44.95 g of the product (67%) was obtained in the same manner as described in the synthesis method of Sub 1b-1, except that naphthalen-1-amine (28.64 g, 200 mmol), 2-bromo-9 was used. 9-Dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol And toluene (1930 mL).

Synthesis of Sub 3b-4

49.88 g of the product (69%) was obtained in the same manner as described in the synthesis of Sub 1b-1 except that biphenyl-4-amine (33.84 g, 200 mmol), 2-bromo-9 was used. , 9-dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 Methyl) and toluene (1930 mL).

Synthesis of Sub 3b-5

47.78 g of the product (65%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 9,9-dimethyl-9H-indole-2-amine (41.86 g, 200 mmol), 2-bromo-5-phenylthiophene (57.39 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g , 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-6

43.53 g of the product (69%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 4-methoxyaniline (24.63 g, 200 mmol), 2-bromo-9 was used. , 9-dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 Methyl) and toluene (1930 mL).

Synthesis of Sub 3b-7

47.31 g of the product (63%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 9,9-dimethyl-9H-indole-2-amine (41.86 g, 200 mmol), 2-bromodibenzo[b,d]furan (59.3 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt- Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-8

38.91 g of the product (67%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that d5-aniline (32.65 g, 200 mmol), 2-bromo-9,9- was used. Dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and Toluene (1930 mL).

Synthesis of Sub 3b-9

50.58 g of the product (69%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 4-benzene-d5-phenyl-1-amine (34.85 g, 200 mmol) was used. 2-Bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-10

45.89 g of the product (67%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 2-bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), 2-naphthylamine-d7 (30.05 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 Methyl) and toluene (1930 mL).

Synthesis of Sub 3b-11

48.91 g of the product (66%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 2-bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), biphenyl-d9-4-amine (35.66 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g , 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-12

53.45 g of the product (64%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 1-amine-4-phenyl-naphthalene-d6 (45.06 g, 200 mmol) was used. 2-Bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-13

54.28 g of the product (65%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 2-amine-6-phenyl-naphthalene-d6 (45.06 g, 200 mmol) was used. 2-Bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-14

51.90 g of the product (62%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 4-(naphthalen-1-yl-d7)aniline (45.26 g, 200 mmol) was used. , 2-bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt- Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-15

53.25 g of the product (63%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 2-bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), 4-(naphthalen-2-yl)aniline-d11 (46.07 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt- Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-16

56.28 g of the product (63%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 4-(biphenyl-4-yl-d9)-aniline (50.87 g, 200) was used. Methyl), 2-bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-17

54.49 g of the product (61%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 9,9-dimethyl-9H-indole-2-amine (41.86 g, 200 mmol), 4'-bromo-3-phenyl-d5-biphenyl-d4 (76.38 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol) NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-18

47.69 g of the product (64%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 9-dimethyl-9H-indole-2-amine (41.86 g, 200 mmol) was used. ), 2-bromo-5-benzene-d5-thiophene (57.39 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7) g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-19

64.68 g of the product (67%) was obtained in the same manner as described in the synthesis method of Sub 1b-1, except that 9,9-dimethyl-7-benzene-d5-9H-indole-2 was used. -amine (58.08 g, 200 mmol), 2-bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ ( 5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-20

78.88 g of the product (65%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 2-bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), 7-(phenyl-d5)-9,9-diphenyl-9H-indol-2-amine (82.91 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ (5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

Synthesis of Sub 3b-21

72.57 g of the product (60%) was obtained in the same manner as described in the synthesis of Sub 1b-1, except that 2-bromo-9,9-dimethyl-9H-indole (65.56 g, 240 mmol), 7-(phenyl-d5)-9,9' spirobis[芴]-2-amine (82.51 g, 200 mmol), Pd ₂ (dba) ₃ (5.5 g, 6 mmol), PPh ₃ ( 5.25 g, 20 mmol), NaOt-Bu (57.7 g, 600 mmol) and toluene (1930 mL).

[Table 6]

Example of a final product synthesis method

In a round bottom flask, a compound of Sub 2b (1.2 equivalents), a compound of Sub 3b (1 equivalent), Pd ₂ (dba) ₃ (0.06 to 0.1 mmol), PPh ₃ (0.2 equivalent), NaOt-Bu were charged. (6 equivalents) and toluene (10.5 mL / 1 mmol), and the reaction was carried out at 100 °C. After completion of the reaction, the resulting product was extracted with diethyl ether and water. Dried over MgSO ₄ and the organic layer was concentrated. The resulting organic material is purified by a silica gel short column and recrystallized to provide a product.

[Table 7]

Meanwhile, since the compound represented by each structural formula 1 or structural formula 2 has a wide variety of substituents, a synthetic example of the only representative compound is exemplified. However, it should be noted that other compounds represented by Structural Formula 1 or Structural Formula 2, although in combination It is not exemplified in the examples and may form part of this specification.

Further, in the core structure in the above structure, various substituents may be employed in order to synthesize a compound having the uniqueness of the substituent employed. For example, in the manufacture of an organic electronic component such as an organic light-emitting element, a substituent for a hole injection layer material, a hole transport layer material, a light-emitting layer material, and an electron transport layer material may be employed in the structure to enable preparation. Meet the needs of each organic material layer.

The compounds of the present invention can be used for various purposes in organic electroluminescent electronic devices depending on the kind and nature of the substituents.

The compounds of the present invention can be optionally modified with a central core and a substituent, and thus can be used in each layer, and can be used in the body of a phosphorescent or fluorescent light-emitting layer.

The organic electronic component of the present invention can be produced by a conventional method and a conventional material for producing an organic electronic component, in addition to forming at least one organic material layer using the above compound.

Of course, even when the compound of the present invention is used for other organic material layers of an organic electroluminescence element such as a light-emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, the same effect can be achieved.

At the same time, the compounds of the invention can be used in a soluble procedure. In other words, an organic material layer of an organic electronic component (which will be described later) can be formed by a dissolving procedure of the compound. In other words, when the compound is used as an organic material layer, it can be used by a dissolving procedure or a solvent procedure instead of deposition (for example, spin coating, dip coating, knife coating, screen printing, inkjet printing or heat). The various polymeric materials of the method of transfer) and the layer of organic material are fabricated in fewer layers.

The compound of the present invention can be used for the organic electronic components, including, for example, an organic light emitting diode (OLED), an organic solar cell, an organic photo conductor (OPC) drum. And organic transistors (organic thin film transistors) and the like.

As an example of an organic electronic component using a compound of the invention, the following An organic light emitting diode (OLED) is described, but the invention is not limited thereto. The above compounds can be used in various organic electronic components.

In another embodiment of the present invention, there is provided an organic electronic component (organic electroluminescent device) comprising a first electrode, a second electrode, and an organic material layer interposed between the electrodes, wherein at least one organic material The layer comprises a compound of the invention.

Figures 1 through 6 show an example of the use of a compound of the invention for an organic electroluminescent element.

In addition to forming at least one organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer in a manner including the compound of the present invention, the field can be known in the art by a conventionally known structure. A conventionally known manufacturing method and material are used to manufacture an organic electroluminescent device according to another embodiment of the present invention.

The structure of the organic electroluminescence element according to another embodiment of the present invention is shown in Figs. 1 to 6, but the present invention is not limited to this structure. Here, the reference numeral 101 represents a substrate, the reference numeral 102 represents an anode, the reference numeral 103 represents a hole injection layer (HIL), the reference numeral 104 represents a hole transport layer (HTL), and the reference numeral 105 represents an illuminating layer (EML). Reference numeral 106 denotes an electron injection layer (EIL), reference numeral 107 denotes an electron transport layer (ETL), and reference numeral 108 denotes a cathode.

Although not shown, the organic electroluminescent device may further comprise a hole blocking layer (HBL) for blocking hole movement, an electron blocking layer (EBL) for blocking electron movement, and a support or auxiliary light. The emitted light emitting auxiliary layer and a protective layer. The protective layer may be formed on the uppermost layer (protecting the organic material layer or the cathode 108).

Here, the compound of the present invention includes at least one organic material layer including a hole injection layer 103, a hole transport layer 104, a light-emitting layer 105, and an electron transport layer 107.

Specifically, the compound of the present invention can replace the hole injection layer 103, the hole transport layer 104, the light emitting layer 105, the electron transport layer 107, the electron injection layer 106, the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer, and the protective layer. At least one of them may be used in combination to form a multilayer structure. Of course, the compound can be used not only for one layer of organic material but also for two or more Floor.

In particular, the compounds of the present invention can be used as materials for hole injection, hole transport, electron injection, electron transport, light emission, and protection (cover layer). In particular, it may be used alone as a luminescent material, a host or a dopant in the host/dopant, and may be used as the hole injection layer 103 or the hole transport layer 104.

For example, in the manufacture of the organic electroluminescent device according to another embodiment of the present invention, physical vapor deposition (PVD), such as sputtering or electron beam evaporation, can be performed on a substrate 101. A metal, a conductive metal oxide or an alloy thereof is deposited to form an anode 102, and then a hole injection layer 103, a hole transport layer 104, a light emitting layer 105, an electron transport layer 107, and an electron injection layer 106 may be formed thereon. A layer of organic material, and a material that can serve as the anode 102 can be deposited thereon.

Further, on a substrate 101, a cathode material, an organic material layer and an anode material may be sequentially deposited to provide an organic electronic component. The organic material layer may be formed as a multilayer structure including the hole injection layer 103, the hole transport layer 104, the light emitting layer 105, the electron transport layer 107, and the electron injection layer 106, but the present invention is not limited thereto. It can be formed into a single layer structure.

Furthermore, various polymers can be used by methods that use a dissolvable procedure or a solvent procedure rather than deposition (eg, spin coating, dip coating, knife coating, screen printing, inkjet printing, or thermal transfer). The material and the layer of organic material are made in fewer layers.

In the organic electroluminescent element of another embodiment of the present invention, the above compound can be used in a dissolving procedure such as a spin coating process or an ink jet process.

The substrate 101 is a carrier for an organic electroluminescence element, and a germanium wafer, a quartz or glass plate, a metal plate, a plastic film or a sheet can be used.

On the substrate 101, an anode 102 is disposed. This anode 102 allows holes to be injected into the hole injection layer 103 provided thereon. A material having a high work function can be used as the anode material so that hole injection into the organic material layer can be smoothly performed. Specific examples of the anode material used in the present invention may include: a metal (for example, vanadium, chromium, copper, zinc, gold) or an alloy thereof; such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) Metal oxide; metal-oxide composition such as ZnO:Al or SnO ₂ :Sb; and poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene Conductive polymer of (PEDT), polypyrrole and polyaniline, but the invention is not limited thereto.

On the anode 102, a hole injection layer 103 is provided. The material of the hole injection layer 103 needs to have high efficiency for injecting holes from the anode 102, and can efficiently transport the injected holes. To this end, the material must have low ionization potential, high transparency (visible against visible ray) and high hole stability.

A material which is effective for injecting a hole from the anode 102 at a low voltage is used as a hole injecting material. The Highest Occuppied Molecular Orbital (HOMO) of the hole injection material can be from the work function of the anode material to the highest occupied molecular orbital of the adjacent organic material layer. Specific examples of the hole injecting material may include a metal porphyrin-based organic material, an oligothiophene-based organic material, an arylamine-based organic material, a hexaonitrile hexaazabenzophenanthrene-based organic material, a quinacridone-based organic material, and an anthracene. The organic material, the ruthenium-based conductive polymer, the polyaniline-based conductive polymer, and the polythiophene-based conductive polymer, but the invention is not limited thereto.

On the hole injection layer 103, a hole transport layer 104 is provided. The hole transport layer 104 receives the holes transmitted from the hole injection layer 103 and transmits them to the organic light-emitting layer 105 disposed thereon. Moreover, the hole transport layer 104 has high hole mobility and high hole stability, and plays the role of blocking electrons. In addition to these general needs, when used in a car display, the heat resistance of the device is required for the device, and thus it can be made of a material having a glass transition temperature (Tg) of 70 ° C or higher.

Examples of materials satisfying these conditions may include NPD (or NPB), a spirocyclic arylamine-based compound, a fluorene-arylamine compound, a nitrogen cycloheptatriene compound, bis(diphenylvinylphenyl) onion, and hydrazine. An cerium oxide compound, a aryl aromatic compound, and the like.

On the hole transport layer 104, an organic light emitting layer 105 is disposed. The organic The light-emitting layer 105 is made of a material having high quantum efficiency, in which holes and electrons are respectively injected from the anode 102 and the cathode 108, and recombined to emit a light source. A material is used as the light-emitting material, which allows the holes respectively transmitted from the hole transport layer 104 and the electron transport layer 107 to combine with electrons to emit light in the visible light range. Preferably, materials having high quantum efficiency for fluorescence or phosphorescence can be used.

As a material or compound satisfying these conditions, Alq3 can be used for green, while Balq (8-hydroxyquinolinium salt), DPVBi (4,4'-bis(2,2-distyryl)-1,1'- Biphenyl) based material, spiro material, spiro ring containing DPVBi (spiro-4,4'-bis(2,2-distyryl)-1,1'-biphenyl), LiPBO (2-(2) -benzoxazole)-phenoxy lithium), bis(diphenylvinylphenylvinyl)benzene, aluminum-quinoline metal complex, imidazole, thiazole and oxazole-metal complex, etc. In blue. In order to increase the luminous efficiency of blue, a small amount of cerium and BczVBi (3,3'[(1,1'-biphenyl)-4,4'-diyldi-2,1-ethylenediyl] double may be doped. (9-ethyl)-9H-carbazole; stilbene aromatic (DSA). In the case of red, the green light-emitting material can be incorporated with a small amount of DCJTB ([2-(1,1-dimethyl) -6-[2-(2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H-benzo(ij)quinolin-9-yl)vinyl ]-4H-pyran-4-ylidene]-malononitrile).

When a light-emitting layer 105 is formed using a procedure such as inkjet printing, roll coating, spin coating, a polymer such as polyphenylethylene (PPV)-based polymer or polyfluorene may be used for an organic light-emitting layer 105. .

On the organic light-emitting layer 105, an electron transport layer 107 is provided. The electron transport layer 107 requires a material having high efficiency of electrons injected from the cathode 108 provided thereon, and the injected electrons can be efficiently transported. To this end, a material having high electron affinity, high electron mobility, and high electron stability is required.

Specific examples of the electron transporting material satisfying these conditions may include an aluminum complex of 8-hydroxyquinoline, a complex containing Alq3, an organic radical compound, and a hydroxyflavone-metal complex, but the present invention is not limited thereto. this.

On the electron transport layer 107, an electron injection layer 106 is stacked. By using a metal complex compound (for example, Balq, Alq3, Be(bq) ₂ , Zn(BTZ) ₂ , Zn(phq) ₂ , PBD, containing spiro PBD, TPBI and Tf-6P) or having an imidazole ring The electron injecting layer 106 is made of a low molecular material containing an aromatic compound of a boron compound. Here, the electron injection layer 106 having a thickness ranging from 100 Å to 300 Å can be formed.

On the electron injection layer 106, an anode 102 is disposed. This cathode 108 acts to inject electrons into the electron injection layer 106. The same material as used for the anode 102 can be used as the material of the cathode 108. In order to achieve efficient electron injection, a metal having a low work function can be used. In particular, metals such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver or alloys thereof may be used. In addition, a two-layer electrode having a thickness of less than or equal to 100 μm (for example, lithium fluoride and aluminum, lithium oxide and aluminum, and lanthanum oxide and aluminum) 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 is suitable for fluorescence of all colors (for example, red, green, blue, white) and Phosphorescent element. Also, the compound can be used as a material for a host (or dopant) of various colors.

The organic electroluminescence device of the present invention can be manufactured as a front emission type, a rear emission type or a double-sided emission type depending on the material thereof.

Meanwhile, the present invention provides a terminal device comprising a display device and a control portion for driving the display device, the display device comprising the organic electronic component described above. The terminal device means a wired/wireless communication terminal device that is currently in use or will be used in the future. The above terminal device of the present invention may be a mobile communication terminal device such as a mobile phone, and may include various terminal devices, such as a personal digital assistant, an electronic dictionary, a personal multimedia player, a remote control, a navigation unit, and a game. Machines, various TVs and various computers.

Manufacturing and testing of organic electronic components

Then, an organic electroluminescent element is manufactured by a conventional method by using the compound synthesized by the invention as a light-emitting host material of a light-emitting layer 105 (or as a hole transport layer 104). First, a 2-TNATA film having a thickness of 10 nm was vacuum-deposited on a layer of indium tin oxide (anode 102) formed on a glass substrate 101 as a hole injection layer 103. Continued, will each hair The compound of the formula (compounds of Structural Formula 1 and Structural Formula 2) was vacuum deposited on the film at a thickness of 20 nm as a hole transport layer 104. Then, a comparative test was conducted. Next, in the comparative test, BD-052X (Idemitsu) was used as a luminescent dopant, and 9,10-di-(naphthalene-2-onion)=AND] was used as a host material, and the fixed doping concentration was 4%. Then, a 40-nano (8-quinoline) aluminum having a thickness of 40 nm was formed as an electron injecting layer 106. Then, a LiF (alkali metal halide) having a thickness of 0.2 nm was deposited, and aluminum (Al) having a thickness of 150 nm was deposited. When the organic electroluminescent element is assembled, Al/LiF is used as the cathode 108.

Comparative example:

An organic electronic component was fabricated in the same manner as described above except that the hole transport layer material used the following compounds.

Meanwhile, when the electroluminescence (EL) characteristic is measured by PR-650 (Photoresearch), the forward bias voltage DC voltage is applied to the organic electroluminescence element of the present invention manufactured by the above method and the comparative example is manufactured. Electroluminescent element. Therefore, the lifetime of the T90 was measured by a life measuring machine (Mcscience) at a reference luminance of 300 cd/m ² . The measurement results are recorded in the table below.

In the case of the results of the examples and comparative examples, the following Table 8 and Table are recorded. In 9, comparing with each other, the compound substituted by ruthenium showed a reduced driving voltage as compared with Comparative Examples 1, 2 and 3. In addition, it not only shows a drop in the driving voltage, but also has high luminous efficiency and long life.

Also, in order to determine the efficacy of hydrazine substitution, a test was performed on the following three compounds. As a result, the results shown in Figures 7 to 9 were obtained.

Meanwhile, in order to compare the device characteristics between the introduction and the introduction, a test was performed on the following compounds. As a result, the results shown in Figures 7 to 9 were obtained. Fig. 7 to Fig. 9 are graphs showing comparisons of compounds which are not used in the compounds used in the present invention in terms of luminance, current density and efficiency.

Referring to Figures 7 to 9, in the introduction of an aryl group, it can be seen that when ruthenium is introduced into the terminal aryl group (P-71 compound), the compound has the most excellent luminance, current density and efficiency. Therefore, the ruthenium introduced compound (P-71, sample A) showed better device characteristics with respect to one unincorporated compound (sample B). Furthermore, the introduction of ruthenium into the terminal aryl group results in the most excellent device characteristics.

At the same time, the materials of [Table 9] were mixed in a ratio of 50:50 with examples of relatively high heat resistance, low driving voltage and long life (70), examples (71) and examples (72). Then, in the same manner as described above, the hole transport layer is used to fabricate a device. The test results on the device are as follows.

The compound of Comparative Example (1) (i.e., NPB) in [Table 8] and the compound showing the most excellent results of Example 70, Example 71, and Example 72 were set as Comparative Examples in [Table 10]. Then, each mixture obtained by mixing P-70, P-71 and P-72 with the other compounds in [Table 9] in a ratio of 50:50 was used for a hole transport layer. Then, through a device test, it was found that the hole transport layer using the mixtures has better characteristics such as low driving voltage, high efficiency, and long life than the use of a single compound.

This is because the mixture of the hydrazine-substituted compounds shows a preferred form compared to the single compound. Specifically, the ruthenium-substituted compound has a high interfacial adhesion, thereby increasing energy transfer between the layers, and then reducing the driving voltage.

Therefore, determining the drop in the driving voltage results in high efficiency and long life. Then, it is expected that the compound can solve the recent problems of the OLED device, for example, a short life caused by a high driving voltage.

Of course, even when the compound of the present invention is used for other organic material layers of an organic electroluminescence element such as a light-emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, the same effect can be achieved.

While the preferred embodiment of the present invention has been described for the purposes of illustration, it will be understood by those skilled in the art The scope and spirit of the invention. Therefore, the embodiments disclosed in the present invention are intended to exemplify the scope of the technical idea of the present invention, and the scope of the present invention is not limited to the embodiments. The scope of the present invention is to be construed as being limited by the scope of the appended claims.

101‧‧‧Substrate

102‧‧‧Anode

103‧‧‧ hole injection layer

104‧‧‧ hole transport layer

105‧‧‧Lighting layer

106‧‧‧Electronic transport layer

107‧‧‧Electronic injection layer

108‧‧‧ cathode

201‧‧‧Substrate

202‧‧‧Anode

203‧‧‧ hole injection layer

204‧‧‧ hole transport layer

205‧‧‧Lighting layer

206‧‧‧Electronic transport layer

208‧‧‧ cathode

301‧‧‧Substrate

302‧‧‧Anode

303‧‧‧ hole injection layer

304‧‧‧ hole transport layer

305‧‧‧Lighting layer

308‧‧‧ cathode

401‧‧‧Substrate

402‧‧‧Anode

404‧‧‧ hole transport layer

405‧‧‧Lighting layer

406‧‧‧Electronic transport layer

408‧‧‧ cathode

501‧‧‧Substrate

502‧‧‧Anode

505‧‧‧Lighting layer

506‧‧‧Electronic transport layer

508‧‧‧ cathode

601‧‧‧Substrate

602‧‧‧Anode

605‧‧‧Lighting layer

608‧‧‧ cathode

1 to 6 show an organic electroluminescent element using the present invention An example of things.

Fig. 7 to Fig. 9 are graphs showing comparisons of compounds which are not used in the compounds used in the present invention in terms of luminance, current density and efficiency.

101‧‧‧Substrate

102‧‧‧Anode

103‧‧‧ hole injection layer

104‧‧‧ hole transport layer

105‧‧‧Lighting layer

106‧‧‧Electronic transport layer

107‧‧‧Electronic injection layer

108‧‧‧ cathode

Claims (16)

An organic electronic component comprising a first electrode, a second electrode and at least one organic material layer, the organic material layer comprising a compound represented by the following structural formula 1: In the above structural formula 1, (1) Ar ₁ and Ar ₃ are the same or different, and each independently is selected from the group consisting of C ₆ to C ₆₀ aryl groups which have at least one substituent. Unsubstituted or substituted, and the substituent is selected from hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₁ ~ C ₂₀ alkoxy, C ₁ to C ₂₀ alkylamino group, C ₁ to C ₂₀ alkylthiophenyl group, C ₆ to C ₂₀ aryl thienyl group, C ₂ to C ₂₀ alkenyl group, C ₂ to C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl, C ₆ ~ C ₆₀ aryl, C ₆ ~ C ₂₀取代 substituted aryl, C ₈ ~ C ₂₀ aralkenyl, C ₆ ~ C ₂₀ aromatic amine a group consisting of a heterocyclic group of a decyl group, a decyl group, a boron group, a fluorenyl group and a C ₃ to C ₂₀ group; a heterocyclic group of C ₂ to C ₆₀ which is unsubstituted or substituted with at least one substituent, and The substituent is selected from the group consisting of hydrogen, hydrazine, halogen, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ aromatic amine a aryl group of C ₆ -C ₆₀ , an aryl group of C ₆ -C ₂₀ substituted by hydrazine, an aralkyl group of C ₇ -C ₂₀ , an alkenyl group of C ₈ -C ₂₀ , C ₃ -C ₂₀ Heterocyclyl, nitrile and alkynyl The composition of the group, and contains oxygen, nitrogen and sulfur, at least one; C ₁ ~ C ₃₀ alkoxy group of which is unsubstituted or substituted by at least one substituent, and the substituent is selected from the group consisting of hydrogen, deuterium , halo, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₃ -C ₃₀ cycloalkyl a C ₂ -C ₃₀ heterocycloalkyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₂₀ aryl group substituted by hydrazine, and a C ₂ -C ₂₀ heterocyclic group; C ₆ -C ₃₀ An aryloxy group which is unsubstituted or substituted with at least one substituent selected from the group consisting of hydrogen, anthracene, halo, an amine group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, C ₂ -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, fluorene a substituted C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heterocyclic group; a C ₆ -C ₆₀ arylamino group which is unsubstituted or substituted with at least one substituent, and the substituent is selected from the group consisting of halo, amino, nitrile, nitro, C ₁ ~ C ₂₀ alkyl group of, C ₂ ~ C ₂₀ alkenyl group of, C ₁ ~ C ₂₀ of alkoxy, cycloalkyl of C ₃ ~ C ₃₀ Alkyl, C ₂ a heterocycloalkyl group of -C ₃₀ , an aryl group of C ₆ -C ₆₀ and a heterocyclic group of C ₂ to C ₂₀ ; and a C ₁ -C ₅₀ alkyl group which is unsubstituted or substituted by a substituent, and The substituent is selected from the group consisting of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ aryl, hydrazine _{a group of 6} to C ₂₀ aryl groups, C ₇ to C ₂₀ aralkyl groups, C ₈ to C ₂₀ aralkenyl groups, C ₃ to C ₂₀ heterocyclic groups, nitrile groups and alkynyl groups, wherein At least one of Ar ₁ to Ar ₃ comprises at least one fluorene, (2) R ₁ and R _{2 are} each independently the same or different, and are selected from the group consisting of hydrogen; hydrazine; halogen; nitro; a nitrile group; an amine group; a C ₆ -C ₆₀ aryl group which is unsubstituted or substituted with at least one substituent selected from hydrogen, hydrazine, halogen, amine group, nitrile group, nitro group , C ₁ ~ C ₂₀ alkyl, C ₁ ~ C ₂₀ alkoxy, C ₁ ~ C ₂₀ alkyl amine, C ₁ ~ C ₂₀ alkyl thienyl, C ₆ ~ C ₂₀ aryl Substituted by thienyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl, C ₆ -C ₆₀ aryl, C ₆ -C ₂₀ Aryl, C ₈ a group consisting of a C ₂₀ aralkenyl group, a C ₆ -C ₂₀ arylamine group, a decyl group, a boron group, a fluorenyl group, and a C ₃ -C ₂₀ heterocyclic group; a heterocyclic group of C ₂ to C ₆₀ a group which is unsubstituted or substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, halo, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ a C ₂₀ alkoxy group, a C ₆ -C ₂₀ arylamine group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₂₀ aryl group substituted by hydrazine, a C ₇ ~C ₂₀ aralkyl group, a group consisting of C ₈ to C ₂₀ aralkenyl groups, C ₃ to C ₂₀ heterocyclic groups, nitrile groups and alkynyl groups, and containing at least one of oxygen, nitrogen and sulfur; C ₁ to C ₃₀ alkoxylates a group which is unsubstituted or substituted with at least one substituent selected from the group consisting of hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, C ₂ -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, hydrazine substituted a C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heterocyclic group; a C ₆ -C ₃₀ aryloxy group which is unsubstituted or substituted with at least one substituent, and the substituent is selected from Hydrogen Deuterium, halo, amino, nitrile, nitro, C ₁ ~ C ₂₀ alkyl group of, C ₂ ~ C ₂₀ alkenyl group of, C ₁ ~ C ₂₀ of alkoxy, cycloalkoxy of C ₃ ~ C ₃₀ a C ₂ -C ₃₀ heterocycloalkyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₂₀ aryl group substituted by hydrazine, and a C ₂ -C ₂₀ heterocyclic group; and C ₁ -C An alkyl group of ₅₀ , which is unsubstituted or substituted by a substituent selected from the group consisting of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkane the substituted group, the C ₆ ~ C ₂₀ aryl group, C ₆ ~ C ₂₀ deuterium of the aryl group, C ₇ ~ C ₂₀ aralkyl group of, C ₈ ~ C ₂₀ alkenyl group of aryl, C ₃ ~ C ₂₀ a group consisting of a heterocyclic group, a nitrile group and an alkynyl group, wherein each of R ₁ and R ₂ is bonded to an adjacent group to form an alicyclic compound, an aromatic compound or a heterocyclic compound, (3) L An extended aryl group representing C ₆ to C ₆₀ which is unsubstituted or substituted with at least one substituent selected from the group consisting of a nitro group, a nitrile group, a halogen group, an alkyl group, an alkoxy group, and an amine group. , the group consisting of an aryl group and a heterocyclic group; or a C ₂ ~ C ₆₀ heterocycloalkyl group of which is unsubstituted or substituted with at least one substituent, and the substituent is From the group consisting of nitro, nitrile, halogen, alkyl, alkoxy, amine and aryl, and (4) a represents an integer from 0 to 4, and b represents an integer from 0 to 3. , c represents an integer from 0 to 2. The organic electronic component according to claim 1, wherein the organic material layer comprises a composition having a mixture comprising two or more different compounds derived from the compound represented by the above structural formula 1. The organic electronic component according to claim 1, wherein the organic material layer comprises a composition having a mixture comprising the compound represented by the above structural formula 1 and the compound represented by the following structural formula 2: In the above structural formula 2, (1) Ar ₁ to Ar ₃ are the same as those of the substituents of Ar ₁ to Ar ₃ in the above structural formula 1, and (2) R ₁ to R ₄ are the same as the above structural formula. The definition of the substituents of R ₁ or R ₂ wherein each of R ₁ to R ₄ is bonded to an adjacent group to form an alicyclic compound, an aromatic compound or a heterocyclic compound, and (3) R' And R" are the same or different, and each independently is a C ₆ -C ₆₀ aryl group which is unsubstituted or substituted with at least one substituent, and the substituent is selected from hydrogen, hydrazine, halogen, amine group , nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thienyl group, C ₆ ~C ₂₀ aryl thienyl, C ₂ ~ C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl, C ₆ ~ C ₆₀ aryl, hydrazine substituted a C ₂ -C ₂₀ aryl group, a C ₈ -C ₂₀ aralkenyl group, a C ₆ -C ₂₀ arylamine group, a decyl group, a boron group, a fluorenyl group and a C ₃ -C ₂₀ heterocyclic group a group; or a C ₁ -C ₅₀ alkyl group substituted or unsubstituted with at least one substituent, and the substituent is selected from C ₁ to C ₂₀ Alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group, oxime substituted C ₂ ~C ₂₀ aryl group, C ₇ ~C ₂₀ a group consisting of an aralkyl group, a C ₈ -C ₂₀ aralkenyl group, a C ₃ -C ₂₀ heterocyclic group, a nitrile group, and an alkynyl group, wherein R' and R" are bonded to each other to form an alicyclic compound An aromatic compound, a heterocyclic compound or a spiro compound, and (4) a represents an integer of 1 to 3, and each of b, c, and d represents an integer of 1 to 4. The organic electronic component according to claim 1, wherein Ar ₂ is represented by the following structural formula: In the above formula, (1) R ₃ and R ₄ are the same or different and each independently is selected from the group consisting of halogen; nitro; nitrile; amine; C ₆ to C ₆₀ An aryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C of ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl group of the amino, C alkyl thiophene group of ₁ ~ C _20, C aryl thiophene group of ₆ ~ C _20, C ₂ ~ C ₂₀ alkenyl group of , C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀取代 substituted aryl group, C ₈ ~ C ₂₀ a olefin a group consisting of a C ₆ -C ₂₀ arylamino group, a decyl group, a boron group, a fluorenyl group, and a C ₃ -C ₂₀ heterocyclic group; a C ₂ -C ₆₀ heterocyclic group having at least one The substituent is unsubstituted or substituted, and the substituent is selected from the group consisting of hydrogen, hydrazine, a halogen group, a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, and a C ₁ -C ₂₀ alkoxy group. a C ₆ -C ₂₀ arylamine group, a C ₆ -C ₆₀ aryl group, a C6-C ₂₀ aryl group substituted by hydrazine, a C ₈ -C ₂₀ aralkyl group, a C ₈ ~C ₂₀ aryl group Alkenyl, C ₃ ~C _{2 a} group consisting of a heterocyclic group, a nitrile group and an alkynyl group of ₀ , and comprising at least one of oxygen, nitrogen and sulfur; a C ₁ -C ₃₀ alkoxy group which is unsubstituted or substituted with at least one substituent, And the substituent is selected from the group consisting of hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ ~C ₂₀ alkane An oxy group, a C ₃ -C ₃₀ cycloalkyl group, a C ₂ -C ₃₀ heterocycloalkyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₂₀ aryl group substituted by hydrazine, and a C ₂ -C _a heterocyclic group of ₂₀ ; an aryloxy group of C ₆ to C ₃₀ which is unsubstituted or substituted with at least one substituent selected from hydrogen, hydrazine, a halogen group, an amine group, a nitrile group, Nitro, C ₁ ~ C ₂₀ alkyl, C ₂ ~ C ₂₀ alkenyl, C ₁ ~ C ₂₀ alkoxy, C ₃ ~ C ₃₀ cycloalkyl, C ₂ ~ C ₃₀ heterocycloalkane a C ₆ -C ₆₀ aryl group, a C ₆ -C ₂₀ aryl group substituted by hydrazine, and a C ₂ -C ₂₀ heterocyclic group; and a C ₁ -C ₅₀ alkyl group which is substituted by a substituent an unsubstituted or substituted, and the substituent is selected from the group consisting of C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group of, C ₁ ~ C ₂₀ alkoxy group of, C ₆ ~ C ₂₀ aryl group of Replaced by a group consisting of a C ₆ -C ₂₀ aryl group, a C ₇ -C ₂₀ aralkyl group, a C ₈ -C ₂₀ aralkenyl group, a C ₃ -C ₂₀ heterocyclic group, a nitrile group, and an alkynyl group, Wherein R ₃ and R _{4 are} each bonded to an adjacent group to form an alicyclic compound, an aromatic compound or a heterocyclic compound, and (2) R' and R" are the same or different and each independently is C ₆ An aryl group of -C ₆₀ which is unsubstituted or substituted with at least one substituent selected from hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkane group, C ₁ ~ C ₂₀ alkyl group of, C ₁ ~ C ₂₀ alkyl group of the amino, C ₁ ~ C ₂₀ alkyl group of thienyl, C ₆ ~ C ₂₀ aryl group of thienyl group, C ₂ ~ C ₂₀ Alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, 氘 substituted C ₆ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ a group consisting of an aralkenyl group, a C ₆ -C ₂₀ arylamine group, a decyl group, a boron group, a fluorenyl group, and a C ₃ -C ₂₀ heterocyclic group; or a C ₁ -C ₅₀ alkyl group; Substituted or unsubstituted with at least one substituent selected from the group consisting of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₆ ~ C An aryl group of ₂₀ , a C ₆ -C ₂₀ aryl group substituted by a hydrazine, a C ₇ -C ₂₀ aralkyl group, a C ₈ -C ₂₀ aralkenyl group, a C ₃ -C ₂₀ heterocyclic group, a nitrile group And a group consisting of alkynyl groups, wherein R' and R" are bonded to each other to form an alicyclic compound, an aromatic compound, a heterocyclic compound or a spiro compound, and (3)e represents an integer of 1 to 4, d represents an integer from 1 to 3, and (4) Ar ₃ contains at least one oxime. The organic electronic component according to claim 1 or 2, wherein at least one of Ar ₁ , Ar ₂ and Ar ₃ is selected from the group consisting of the following compounds: Wherein D represents 氘, a represents an integer from 0 to 5, a' represents an integer from 0 to 7, b represents an integer from 0 to 4, b' represents an integer from 0 to 6, c, c', h, j, m, p, s, t, u, s', t', and u' each represent an integer of 0 to 5, and d, e, f, g, and l each represent an integer of 0 to 4, i and k Each represents an integer of 0 to 2, and n, o, q, r, q', and r' each represent an integer of 0 to 3. The organic electronic component according to claim 1 or 2, wherein at least one of Ar ₁ , Ar ₂ and Ar ₃ is selected from the group consisting of the following compounds: The organic electronic component according to claim 1, wherein the compound represented by the above structural formula 1 is selected from the group consisting of the following compounds: The organic electronic component according to claim 3, wherein the compound represented by the above structural formula 2 is selected from the group consisting of the following compounds: The organic electronic component according to any one of claims 1 to 3, wherein the organic material layer is formed by a soluble procedure of the compound or the composition. The organic electronic component according to any one of claims 1 to 3, wherein the organic electronic component is an organic electroluminescent component, which sequentially stacks the first electrode, the organic material layer, and the second electrode. The organic electronic component according to any one of claims 1 to 3, wherein the organic material layer comprises a light-emitting layer, a hole injection layer, and a hole transmission At least one layer of the layer. The organic electronic component according to claim 2, wherein in the composition, any one of the compounds is mixed in a composition equal to or less than 90% by weight based on the total weight of the composition. An electronic device comprising: a display device comprising the organic electronic component of any one of claims 1 to 3; and a control portion designed to drive the display device. The electronic device of claim 12, wherein the organic electronic component is an organic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor (organic thin film transistor), and a monochromatic or white light illumination device. any type. A compound represented by the following structural formula 3: In the above structural formula 3, (1) Ar ₁ and Ar ₃ are the same or different, and each independently is selected from the group consisting of C ₆ to C ₆₀ aryl groups having at least one substituent. Unsubstituted or substituted, and the substituent is selected from hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ ~ C ₂₀ alkyl, C ₁ ~ C ₂₀ alkoxy, C ₁ to C ₂₀ alkylamino group, C ₁ to C ₂₀ alkylthiophenyl group, C ₆ to C ₂₀ aryl thienyl group, C ₂ to C ₂₀ alkenyl group, C ₂ to C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl, C ₆ ~ C ₆₀ aryl, C ₆ ~ C ₂₀取代 substituted aryl, C ₈ ~ C ₂₀ aralkenyl, C ₆ ~ C ₂₀ aromatic amine a group consisting of a heterocyclic group of a decyl group, a decyl group, a boron group, a fluorenyl group and a C ₃ to C ₂₀ group; a heterocyclic group of C ₂ to C ₆₀ which is unsubstituted or substituted with at least one substituent, and The substituent is selected from the group consisting of hydrogen, hydrazine, halogen, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ aromatic amine a aryl group of C ₆ -C ₆₀ , an aryl group of C ₆ -C ₂₀ substituted by hydrazine, an aralkyl group of C ₇ -C ₂₀ , an alkenyl group of C ₈ -C ₂₀ , C ₃ -C ₂₀ Heterocyclyl, nitrile and alkynyl a group comprising at least one of oxygen, nitrogen and sulfur; a C ₁ -C ₃₀ alkoxy group which is unsubstituted or substituted with at least one substituent, and the substituent is selected from hydrogen, Anthracene, halo, amine, nitrile, nitro, C ₁ to C ₂₀ alkyl, C ₂ to C ₂₀ alkenyl, C ₁ to C ₂₀ alkoxy, C ₃ to C ₃₀ naphthenic a C ₂ -C ₃₀ heterocycloalkyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₂₀ aryl group substituted by hydrazine, and a C ₂ -C ₂₀ heterocyclic group; C ₆ -C ₃₀ An aryloxy group which is unsubstituted or substituted with at least one substituent selected from the group consisting of hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl , C ₂ -C ₂₀ alkenyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₃₀ cycloalkyl group, C ₂ -C ₃₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, a C ₆ -C ₂₀ aryl group substituted with hydrazine and a C ₂ -C ₂₀ heterocyclic group; a C ₆ -C ₆₀ arylamino group which is unsubstituted or substituted with at least one substituent, and the substituent is selected from the group consisting of halo, amino, nitrile, nitro, C ₁ ~ C ₂₀ alkyl group of, C ₂ ~ C ₂₀ alkenyl group of, C ₁ ~ C ₂₀ of alkoxy, C ₃ ~ C ₃₀ of Cycloalkyl, C ₂ a heterocycloalkyl group of -C ₃₀ , an aryl group of C ₆ -C ₆₀ and a heterocyclic group of C ₂ to C ₂₀ ; and a C ₁ -C ₅₀ alkyl group which is unsubstituted or substituted by a substituent, and The substituent is selected from the group consisting of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ aryl, hydrazine _{a group of 6} to C ₂₀ aryl groups, C ₇ to C ₂₀ aralkyl groups, C ₈ to C ₂₀ aralkenyl groups, C ₃ to C ₂₀ heterocyclic groups, nitrile groups and alkynyl groups, wherein At least one of Ar ₁ to Ar ₃ comprises at least one fluorene, (2) R ₁ and R ₂ are the same or different, and each independently is selected from the group consisting of hydrogen; hydrazine; halogen; nitro; a nitrile group; an amine group; an aryl group of C6 to C60 which is unsubstituted or substituted with at least one substituent selected from hydrogen, hydrazine, halogen, amine group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl, C ₁ to C ₂₀ alkoxy, C ₁ to C ₂₀ alkyl amine, C ₁ to C ₂₀ alkyl thienyl, C ₆ to C ₂₀ aryl thienyl , the substituted C ₂ ~ C ₂₀ alkenyl group, the C ₂ ~ C ₂₀ alkynyl group, the cycloalkyl group of C ₃ ~ C _20, C ₆ ~ C ₆₀ aryl group of deuterium of C ₆ ~ C ₂₀ aryl group , C ₈ ~ C _a group consisting of a _20- aryl group, a C ₆ -C ₂₀ arylamine group, a decyl group, a boron group, a fluorenyl group, and a C ₃ -C ₂₀ heterocyclic group; a C ₂ -C ₆₀ heterocyclic group; It is unsubstituted or substituted with at least one substituent selected from hydrogen, hydrazine, halogen, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₁ ~C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl amine group, C ₆ ~ C ₆₀ aryl group, 氘 substituted C ₆ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ aralkyl group, C ₈ - the group consisting of C ₂₀ arylalkenyl group, a heterocyclic group of C ₃ ~ C _20, a nitrile group, and an alkynyl group, and contains oxygen, nitrogen and sulfur, at least one; C ₁ ~ C ₃₀ alkoxy group, the It is unsubstituted or substituted with at least one substituent selected from hydrogen, hydrazine, halogen, amine, nitrile, nitro, C ₁ -C ₂₀ alkyl, C ₂ ~C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₂ ~ C ₃₀ heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 氘 substituted C _{a 6} -C ₂₀ aryl group and a C ₂ -C ₂₀ heterocyclic group; a C ₆ -C ₃₀ aryloxy group which is unsubstituted or substituted with at least one substituent, and the substituent is selected from hydrogen , , Halo, amino, nitrile, nitro, C ₁ ~ C of ₂₀ -alkyl, C ₂ ~ C ₂₀ alkenyl group of, C ₁ ~ C ₂₀ alkoxy group, the cycloalkyl group of C ₃ ~ C ₃₀ a heterocycloalkyl group of C ₂ to C ₃₀ , an aryl group of C ₆ to C ₆₀ , an aryl group of C ₆ to C ₂₀ substituted with hydrazine, and a heterocyclic group of C ₂ to C ₂₀ ; and C ₁ to C ₅₀ An alkyl group which is unsubstituted or substituted with a substituent selected from the group consisting of a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, and a C ₁ -C ₂₀ alkoxy group. a aryl group of C ₆ -C ₂₀ , an aryl group of C ₆ -C ₂₀ substituted by hydrazine, an aralkyl group of C ₇ -C ₂₀ , an alkenyl group of C ₈ -C ₂₀ , C ₃ -C ₂₀ a group consisting of a heterocyclic group, a nitrile group and an alkynyl group, wherein each of R ₁ and R ₂ is bonded to an adjacent group to form an alicyclic compound, an aromatic compound or a heterocyclic compound, and (3) L represents a C ₆ -C ₆₀ exoaryl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a nitro group, a nitrile group, a halogen group, an alkyl group, an alkoxy group, an amine group, the group consisting of an aryl group and a heterocyclic group; or a C ₂ ~ C ₆₀ heterocycloalkyl group of which is unsubstituted or substituted with at least one substituent, and the substituent is selected from And a group consisting of a nitro group, a nitrile group, a halogen group, an alkyl group, an alkoxy group, an amine group, and an aryl group, and (4) a represents an integer of 0 to 4, and b represents an integer of 0 to 3. c represents an integer from 0 to 2. A composition for an organic electronic component comprising a mixture having a compound represented by Structural Formula 3 as described in claim 15 of the above-mentioned patent application and a compound represented by the following Structural Formula 4: In the above structural formula 4, (1) Ar ₁ to Ar ₃ are the same as those of the substituents of Ar ₁ to Ar ₃ in the above structural formula 1, and (2) R ₁ to R ₄ are the same as the above structural formula. The definition of the substituents of R ₁ or R ₂ wherein each of R ₁ to R ₄ is bonded to an adjacent group to form an alicyclic compound, an aromatic compound or a heterocyclic compound, and (3) R' And R" are the same or different, and each independently is a C ₆ -C ₆₀ aryl group which is unsubstituted or substituted with at least one substituent, and the substituent is selected from hydrogen, hydrazine, halogen, amine group , nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thienyl group, C ₆ ~C ₂₀ aryl thienyl, C ₂ ~ C ₂₀ alkenyl, C ₂ ~ C ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl, C ₆ ~ C ₆₀ aryl, hydrazine substituted a C ₂ -C ₂₀ aryl group, a C ₈ -C ₂₀ aralkenyl group, a C ₆ -C ₂₀ arylamine group, a decyl group, a boron group, a fluorenyl group and a C ₃ -C ₂₀ heterocyclic group group; or a C ₁ ~ C ₅₀ alkyl group of which is substituted by at least one substituent group or unsubstituted, and the substituent is selected from the group consisting of C ₁ ~ C ₂₀ Alkyl, the substituted C ₂ ~ C ₂₀ alkenyl group of, C ₁ ~ C ₂₀ alkoxy group of, C ₆ ~ C ₂₀ aryl group of deuterium of C ₂ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ of a group consisting of an aralkyl group, a C ₈ -C ₂₀ aralkenyl group, a C ₃ -C ₂₀ heterocyclic group, a nitrile group, and an alkynyl group, wherein R' and R" are bonded to each other to form an alicyclic compound An aromatic compound, a heterocyclic compound or a spiro compound, and (4) a represents an integer of 1 to 3, and each of b, c, and d represents an integer of 1 to 4.