KR102163320B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving luminous efficiency, stability, and lifespan of a device, an organic electric device using the same, and an electronic device thereof.

Description

Compound for organic electric device, organic electric device using the same, and electronic device thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}

The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

Flat panel display devices are playing a very important role in supporting a high-level video information society, centering on the Internet, which is showing rapid growth in recent years. In particular, organic electric devices capable of low voltage driving by self-luminous type have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs), which are the mainstream of flat panel display devices, and are lightweight and thin because they do not need a backlight. Also, it has an advantage in terms of power consumption. In addition, the response speed is fast and the color reproduction range is wide, attracting attention as a next-generation display device.

In general, the organic EL device is formed on a glass substrate in the order of an anode made of a transparent electrode, an organic thin film including a light emitting region, and a metal electrode. In this case, the organic thin film is a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer in addition to the emitting layer (EML). , EIL), and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to the light emission characteristics of the emission layer. When an electric field is applied to the organic EL device of this structure, holes are injected from the anode and electrons are injected from the cathode, and the injected holes and electrons are recombined in the emission layer through the hole transport layer and the electron transport layer, respectively, resulting in emission excitons. To form. The formed light-emitting excitons emit light while transitioning to the ground states. At this time, a light-emitting dye (guest) is also doped on the light-emitting layer (host) to increase the efficiency and stability of the light-emitting state.

In order to use these organic electronic devices in various display media, the lifespan of the device is more important than anything else, and several studies are currently being conducted to increase the lifespan of the organic electronic device.

An object of the present invention is to provide an amine-based compound substituted with deuterium capable of improving a low driving voltage and lifespan of a device, an organic electric device using the same, and an electronic device thereof.

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

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

By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and lifetime of the device can be greatly improved.

1 is an exemplary diagram of an organic electroluminescent device according to the present invention.

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

In adding reference numerals to elements of each drawing, it should be noted that the same elements are assigned the same numerals as possible even if they are indicated on different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the subject matter of the present invention, a detailed description thereof will be omitted.

In addition, in describing the constituent elements of the present invention, terms such as first, second, A, B, (a), (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, the component may be directly connected or connected to that other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.

Several studies are being conducted on organic materials inserted into a buffer layer such as a hole transport layer or a light emission auxiliary layer for excellent life characteristics of an organic electroluminescent device, and for this purpose, high hole transfer characteristics from the anode to the organic layer are provided. In addition, there is a demand for a hole injection layer and a hole transport layer material having high uniformity and low crystallinity when forming a thin film after deposition.

It delays penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the life of the organic electroluminescent device, and is stable against Joule heating, that is, high glass. There is a need to develop materials for a hole injection layer and a hole transport layer having a transition temperature. In addition, it is reported that the low glass transition temperature of the material for the hole transport layer has a great influence on the life of the device according to the characteristic of the uniformity of the thin film surface being collapsed when the device is driven. In addition, the deposition method is the mainstream in the formation of OLED devices, and a material that can withstand such a deposition method for a long time, that is, a material having strong heat resistance properties is required.

In particular, as the size of panels for mobile phones and tablet PCs has become larger, the current problem of power consumption and lifespan is urgently needed to overcome the major challenges of organic electroluminescent devices.

However, as a material for the hole transport layer, it is difficult to overcome the driving voltage and lifetime at the same time. The reason for this is that in order to lower the driving voltage, materials having excellent hole transport capabilities, that is, high hole mobility, have a planar structure rich in electrons. For example, naphthyl, fluorene, and phenanthrene. However, when the compound of the above structure is introduced into a hole transport material as a substituent, hole mobility is increased up to a certain number and has a good effect on the lifespan, but the number of introduced molecules is increased to reach the low voltage driving target required in the current industry. If increased, the driving voltage decreases and low voltage driving is possible, but the lifespan is rapidly deteriorated. This is because in the case of molecules in which electron-rich planar structures are introduced excessively, when a constant current is continuously supplied during the device lifetime evaluation, holes are trapped and stabilized between the plate-like structures, which lowers the hole mobility. As the driving voltage increases to apply a constant current, the lifespan of the device rapidly deteriorates. This is represented by the following formula.

J = Space Charge limited current

ε = Permittibility

μ = Mobility Coefficient

θ = Charge Trap Coefficient (Free Carrier/total Carrier)

V = Voltage

d = Thickness

As the number of free carriers decreases due to the trap phenomenon, the value of θ decreases. Therefore, in a current-driven organic electroluminescent device that requires a constant current, the driving voltage increases, which is very fatal to the lifespan. It can bring results. Therefore, as described above, the introduction of a plate-like structure rich in electrons that can increase hole mobility more than a certain amount adversely affects the lifespan, and thus the possibility of lowering the driving voltage using this adversely affects the lifespan.

Therefore, in the present invention, in order to solve this part, deuterium is replaced at an appropriate ratio by using a material having a good life, as a method to lower the driving voltage without introducing a plate-like molecular structure that adversely affects the life. A method of lowering the driving voltage by the method is presented.

According to the research results of the present inventors, it was confirmed that the compound substituted with deuterium exhibited many thermodynamic behaviors compared to the unsubstituted compound. Among these thermal properties, when an iridium compound is substituted with deuterium, the properties vary depending on the difference in the bond lengths of carbon, hydrogen and carbon, and deuterium, but the bond length of a compound consisting of deuterium is shorter than that of a compound not substituted with deuterium. It was confirmed that higher luminous efficiency can be obtained due to the weakening of the van der Waals force between molecules generated according to the result.

In addition, when substituted with deuterium, the zero point energy, that is, the energy of the ground state is lowered, and as the bond length of deuterium-carbon is shorter than that of hydrogen-carbon, the molecular hardcore volume is reduced. It was confirmed that the volume of the thin film can be increased by decreasing the amount, thereby reducing the electrical polarizability and weakening the intermolecular interaction. It was judged that this characteristic would be very effective in realizing an amorphous state that is absolutely necessary in order to lower the crystallinity of the thin film, that is, to create an amorphous state, and to increase OLED life and driving characteristics in general.

However, a method of lowering the driving voltage by substituting with deuterium, that is, increasing the mobility of a hole transport material, has not been studied at present, and various types of compounds are used in this study to confirm such characteristics. Thus, many experiments were conducted. In addition, when a thin film is formed with a compound substituted with deuterium, a film is formed in an amorphous glass state that can have a great influence on the hole mobility of the thin film, and this amorphous glass state is isotropic and homogeneous ( It was confirmed that the flow of charge, that is, hole mobility, can be accelerated by reducing the grain boundary through the homogeneous property.

When the present invention is described in more detail, an amine compound was used as a material having excellent life. Of particular note is that amine compounds have excellent lifespan characteristics according to this study, but have a disadvantage of increasing driving voltage. However, in the prior art, there is no evidence of the effect of improvement on this part, and in particular, the prior art in which the driving characteristics are improved through deuterium substitution at a specific position has not yet been reported.

As a result of the research and development of these inventors, the present invention provides a compound in which an amine group substituted with deuterium is bonded in order to meet the required characteristics of an organic material while maintaining the excellent properties of the organic material layers of the organic electronic device described above.

As used in this specification and the appended claims, the meaning of the following terms is as follows, unless stated otherwise.

As used herein, the term "halo" or "halogen" is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise specified.

As used herein, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms unless otherwise specified, and is a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo It means a radical of a saturated aliphatic functional group, including an alkyl group and a cycloalkyl-substituted alkyl group.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise specified.

The term "heteroalkyl group" as used in the present invention means that one or more of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.

The terms "alkenyl group" or "alkynyl group" used in the present invention each have a double bond or triple bond of 2 to 60 carbon atoms, unless otherwise specified, and include a linear or branched chain group, and are limited thereto. It is not.

The term "cycloalkyl" as used in the present invention means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

The terms "alkoxyl group", "alkoxy group", or "alkyloxy group" as used in the present invention means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and is limited thereto. It is not.

The terms "alkenyl group", "alkenoxy group", "alkenyloxy group", or "alkenyloxy group" as used in the present invention mean an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 It has a carbon number of, but is not limited thereto.

The term "aryloxyl group" or "aryloxy group" used in the present invention refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms, and is not limited thereto.

The terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto, unless otherwise specified. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatics, and includes an aromatic ring formed by neighboring substituents participating in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and a radical substituted with an aryl group has the number of carbon atoms described herein.

In addition, when prefixes are named consecutively, it means that the substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group. And the arylcarbonyl group is a carbonyl group substituted with an aryl group.

As used herein, the term “heteroalkyl” refers to an alkyl containing one or more heteroatoms unless otherwise specified. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl group or arylene group having 2 to 60 carbon atoms each including one or more heteroatoms, unless otherwise specified, and is limited thereto No, it includes at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.

The term "heterocyclic group" as used herein, unless otherwise specified, includes one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, and includes heteroaliphatic rings and heterocyclic rings. It contains an aromatic ring. It may be formed by combining adjacent functional groups.

The term "heteroatom" as used herein refers to N, O, S, P, or Si unless otherwise specified.

In addition, the "heterocyclic group" may also include a ring including SO ₂ instead of carbon forming a ring. For example, "heterocyclic group" includes the following compounds.

Unless otherwise specified, the term "aliphatic" as used herein refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" used in the present invention refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof, It contains saturated or unsaturated rings.

Other hetero compounds or hetero radicals other than the aforementioned hetero compounds include one or more heteroatoms, but are not limited thereto.

Unless otherwise specified, the term "carbonyl" as used herein is represented by -COR', where R'is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. A cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise specified, the term "ether" used in the present invention is represented by -RO-R', wherein R or R'are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, and 6 to 30 carbon atoms. An aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

In addition, unless explicitly stated, the term "substituted or unsubstituted" used in the present invention means "substituted" deuterium, halogen, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl group, C ₁ to C ₂₀ alkoxyl group, C ₁ to C ₂₀ alkylamine group, C ₁ to C ₂₀ alkylthiophene group, C ₆ to C ₂₀ arylthiophene group, C ₂ to C ₂₀ alkenyl group, C ₂ to C ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron It means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ ~ C ₂₀ heterocyclic group, and is not limited to these substituents.

In addition, unless there is an explicit explanation, the formula used in the present invention is applied in the same manner as the definition of the substituent group defined by the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and a is an integer of 2 or 3. Each is bonded as follows, wherein R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the hydrogen bonded to the carbon forming the benzene ring is indicated. Is omitted.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, and a first electrode 110 and a second electrode 180 formed on a substrate 110. ) Between the organic material layer including the compound according to the present invention. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, a hole transport layer 140, an emission layer 150, an electron transport layer 160, and an electron injection layer 170 sequentially on the first electrode 120. In this case, other layers other than the emission layer 150 may not be formed. A hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151, a buffer layer 141, etc. may be further included, and the electron transport layer 160 may serve as a hole blocking layer.

Further, although not shown, the organic electric device according to the present invention may further include a protective layer or a capping layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a host of the light emitting layer 150, or a dopant or a light efficiency improvement layer. It could be used as a material. Preferably, the compound of the present invention may be used as the light emitting layer 150, the hole transport layer 140 and/or the light emitting auxiliary layer 151.

On the other hand, even with the same core, the band gap, electrical characteristics, and interfacial characteristics may vary depending on which substituent is bonded to any position, so the selection of the core and the combination of sub-substituents bonded thereto are also very It is important, and in particular, long life and high efficiency can be achieved at the same time when the optimum combination of the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) is achieved.

As described above, in order to solve the problem of light emission in the hole transport layer in recent organic electroluminescent devices, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and each light emitting layer (R, G, B) It is the time when it is necessary to develop different light emitting auxiliary layers. On the other hand, in the case of the light-emitting auxiliary layer, since the correlation between the hole transport layer and the light-emitting layer (host) must be grasped, even if a similar core is used, it will be very difficult to infer its characteristics if the used organic material layer is different.

Therefore, in the present invention, by forming a light emitting layer or a light emitting auxiliary layer using the compound represented by Formula 1, the energy level and T1 value between each organic material layer, the intrinsic properties of the material (mobility, interface properties, etc.) It is possible to improve the life and efficiency of the electric device at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a physical vapor deposition (PVD) method. For example, an anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer ( After forming an organic material layer including 160) and the electron injection layer 170, it may be manufactured by depositing a material that can be used as the cathode 180 thereon.

In addition, the organic material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blaze. It can be manufactured with fewer layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electric device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

WOLED (White Organic Light Emitting Device) is easy to realize high resolution and excellent processability, while there is an advantage that can be manufactured using the existing LCD color filter technology. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Typically, R(Red), G(Green), B(Blue) light emitting parts are arranged side-by-side in a mutually planar way, and R, G, B light emitting layers are stacked up and down. In addition, there is a color conversion material (CCM) method that uses electroluminescence by the blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom. May be applied to such WOLED.

In addition, the organic electric device according to the present invention may be one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a single color or a white lighting device.

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.

Hereinafter, a compound according to an aspect of the present invention will be described.

A compound according to an aspect of the present invention is represented by the following formula (1).

[Formula 1]

In Formula 1, Ar ¹ and Ar ² are each independently a C ₆ ~C ₁₈ aryl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); may be selected from the group consisting of. For example, Ar ¹ and Ar ² are independently of each other, phenyl, naphthyl, biphenyl, 1-phenylnaphthalene, 2-phenylnaphthalene, dibenzothiophene, dibenzofuran, pyridine or 2,4-diphenyl-1, It may be 3,5-triazine and the like.

m and n are each an integer of 0 to 7, where m+n is 1 or more. That is, the case where both m and n are 0 is excluded.

R ¹ and R ² are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl group; O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; An alkoxyl group of C ₁ to C ₃₀ ; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); may be selected from the group consisting of. Here, at least one of R ¹ or R ² is deuterium.

L'is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And C ₂ ~ C ₆₀ of the heterocyclic group; may be selected from the group consisting of.

R ^a and R ^b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl group; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And O, N, S, Si, and a C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of P; It may be selected from the group consisting of.

Meanwhile, each of the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group and fluorenylene group is deuterium; halogen; Silane group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ ~ C ₂₀ alkylthio group; An alkoxyl group of C ₁ to C ₂₀ ; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl group of C ₂ ~ C ₂₀ ; Of C ₆ ~ C ₂₀ Aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ Heterocyclic group; A C ₃ ~C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; And C ₈ ~ C ₂₀ arylalkenyl group; may be substituted with one or more substituents selected from the group consisting of.

Here, in the case of the aryl group, the number of carbon atoms may be 6 to 60, preferably 6 to 30, more preferably an aryl group having 6 to 20 carbon atoms,

In the case of the heterocyclic group, the carbon number may be a heterocyclic group having 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms,

In the case of the arylene group, the number of carbon atoms may be 6 to 60, preferably 6 to 30, more preferably an arylene group having 6 to 20 carbon atoms,

In the case of the alkyl group, the number of carbon atoms may be 1 to 60, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably an alkyl group having 1 to 10 carbon atoms.

Specifically, the compound represented by Formula 1 may be represented by one of the following formulas.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4, Ar ¹ , Ar ² , R ¹ , R ² , m and n may be defined the same as those defined in Formula 1, and D refers to deuterium.

More specifically, the compound represented by Chemical Formulas 1 to 4 may be one of the following compounds.

As another embodiment, the present invention provides a compound for an organic electric device represented by Formula 1 above.

In another embodiment, the present invention provides an organic electric device containing the compound represented by Formula 1.

In this case, the organic electric device includes a first electrode; A second electrode; And an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer may include a compound represented by Formula 1, wherein Formula 1 is a hole injection layer, a hole transport layer, and a light emission auxiliary layer of the organic material layer. Or it may be contained in at least one of the light emitting layers. That is, the compound represented by Formula 1 may be used as a material for a hole injection layer, a hole transport layer, a light emission auxiliary layer, or a light emission layer. Specifically, an organic electric device including one of the compounds represented by Formulas 2 to 4 is provided in the organic material layer, and more specifically, an organic electrical device including a compound represented by the individual formula in the organic material layer is provided. do.

In another embodiment of the present invention, the present invention provides a light efficiency improvement layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric device further comprising.

Hereinafter, examples for synthesizing the compound represented by Formula 1 according to the present invention and an example for preparing an organic electric device will be described in detail, but the present invention is not limited to the following examples.

Synthesis example

Exemplarily, the compound (Final Products) according to the present invention is prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

<Reaction Scheme 1>

I. Sub Of 1 Synthesis example

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.

<Reaction Scheme 2>

One. Sub 1-2 of Synthesis example

In a round bottom flask, Sub 1-2-1 (1 equivalent), Sub 1-2-2 (1 equivalent), Pd ₂ (dba) ₃ (0.05 equivalent), PPh ₃ (0.1 equivalent), NaO t -Bu (3 Equivalent), toluene (10.5mL / Sub 1-2-1 1mmol) was added and the reaction was proceeded at 100℃. When the reaction was completed, the reaction was completed, extracted with ether and water, the organic layer was dried with MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain Sub 1-2.

(1) 1-2 (1) Synthesis Example

In a round bottom flask, Sub 1-2-1(1) (3.1g, 20mmol), Sub 1-2-2(1) (2.9g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 3.6 g (yield: 82%) of 1-2(1).

(2) Synthesis example of 1-2 (12)

In a round bottom flask, Sub 1-2-1(2) (4.7g, 20mmol), Sub 1-2-2(2) (3.0g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 4.4 g (yield: 72%) of 1-2 (12).

(3) Synthesis example of 1-2 (19)

In a round bottom flask, Sub 1-2-1(3) (4.1g, 20mmol), Sub 1-2-2(3) (2.9g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 4.6 g (yield: 85%) of 1-2 (19).

(4) Synthesis example of 1-2(29)

In a round bottom flask, Sub 1-2-1(4) (5.4g, 20mmol), Sub 1-2-2(4) (3.0g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 4.7 g (yield: 70%) of 1-2 (29).

Meanwhile, examples of Sub 1-2 are as follows, but are not limited thereto, and their FD-MS is shown in Table 1 below.

[Table 1]

2. Sub Of 1 Synthesis example

In a round bottom flask, Sub 1-1 (1 equivalent), Sub 1-2 (1 equivalent), Pd ₂ (dba) ₃ (0.05 equivalent), PPh ₃ (0.1 equivalent), NaO t -Bu (3 equivalent), toluene After adding (10.5mL / Sub 1-1 1mmol), the reaction proceeds at 100℃. When the reaction was completed, the reaction was completed, extracted with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain Sub 1.

(1) Synthesis Example of Sub 1 (1)

In a round bottom flask, Sub 1-1 (6.2g, 20mmol), Sub 1-2(1) (4.4g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol) , NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 6.8 g (yield: 76%) of Sub 1(1).

(2) Synthesis Example of Sub 1 (15)

In a round bottom flask, Sub 1-1 (6.2g, 20mmol), Sub 1-2(15) (4.5g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol) , NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 6.7 g (yield: 73%) of Sub 1(1).

(3) Synthesis Example of Sub 1 (20)

In a round bottom flask, Sub 1-1 (6.2g, 20mmol), Sub 1-2(20) (5.9g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol) , NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 7.9 g (yield: 75%) of Sub 1 (20).

(4) Synthesis Example of Sub 1 (25)

In round bottom flask, Sub 1-1 (6.2g, 20mmol), Sub 1-2(25) (4.5g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol) , NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 6.7 g (yield: 73%) of Sub 1 (25).

Meanwhile, examples of Sub 1 are as follows, but are not limited thereto, and their FD-MS is shown in Table 2 below.

[Table 2]

II . Sub Of 2 Synthesis example

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but is not limited thereto.

<Reaction Scheme 3>

In a round bottom flask, Sub 2-1 (1 equivalent), Sub 2-2 (1 equivalent), Pd ₂ (dba) ₃ (0.05 equivalent), PPh ₃ (0.1 equivalent), NaO t -Bu (3 equivalent), toluene After adding (10.5mL / Sub 2-1 1mmol), the reaction proceeds at 100℃. When the reaction was complete, the reaction was completed, extracted with ether and water, the organic layer was dried with MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain Sub 2.

1. Synthesis Example of Sub 2(4)

In a round bottom flask, Sub 2-1(1) (4.7g, 20mmol), Sub 2-2(1) (4.4g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g) , 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 6.2 g (yield: 83%) of Sub 2 (4).

2. Synthesis Example of Sub 2 (22)

In a round bottom flask, Sub 2-1(2) (4.9g, 20mmol), Sub 2-2(2) (4.4g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g) , 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 6.0 g (yield: 78%) of Sub 2 (22).

3. Synthesis Example of Sub 2 (25)

In a round bottom flask, Sub 2-1(3) (3.1g, 20mmol), Sub 2-2(3) (4.5g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g) , 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 4.7 g (yield: 78%) of Sub 2 (25).

4. Synthesis Example of Sub 2 (44)

In a round bottom flask, Sub 2-1(4) (5.7g, 20mmol), Sub 2-2(4) (4.5g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g) , 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 6.6 g (yield: 77%) of Sub 2 (44).

Meanwhile, examples of Sub 2 are as follows, but are not limited thereto, and their FD-MS is shown in Table 3 below.

[Table 3]

III . Final product ( Final Product )of Synthesis example

In a round bottom flask, Sub 1 (1 equivalent), Sub 2 (1 equivalent), Pd ₂ (dba) ₃ (0.05 equivalent), PPh ₃ (0.1 equivalent), NaO t -Bu (3 equivalent), toluene (10.5 mL / Sub 1 1mmol) is added and the reaction proceeds at 100°C. When the reaction was completed, the organic layer was extracted with ether and water, dried with MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain a final product.

1. Synthesis Example of 1-4

In a round bottom flask, Sub 1(9) (9.1g, 20mmol), Sub 2(4) (7.4g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 11.7 g (yield: 78%) of 1-4.

2. Synthesis Example of 2-4

In a round bottom flask, Sub 1(1) (9.0g, 20mmol), Sub 2(28) (7.6g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 11.8 g (yield: 79%) of 2-4.

3. Synthesis Example of 2-41

In a round bottom flask, Sub 1(3) (10.0g, 20mmol), Sub 2(25) (6.0g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 11.0 g (yield: 76%) of 2-41.

4. Synthesis Example of 3-4

In a round bottom flask, Sub 1(9) (9.1g, 20mmol), Sub 2(28) (7.6g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 11.9 g (yield: 79%) of 3-4.

5. Synthesis Example of 3-55

In a round bottom flask, Sub 1(31) (9.2g, 20mmol), Sub 2(39) (7.0g, 20mmol), Pd ₂ (dba) ₃ (0.9g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol) and toluene (210mL) were added respectively, followed by stirring at 100°C for 24 hours to reflux. After extraction with ether and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was recrystallized with a silicagel column to obtain 10.8 g (yield: 75%) of 3-55.

On the other hand, FD-MS of compounds 1-1 to 1-56, 2-1 to 2-56, and 3-1 to 3-56 of the present invention according to the Synthesis Example above are shown in Table 4 below.

[Table 4]

Manufacturing evaluation of organic electric devices

[ Example 1] Green organic light emitting device ( Hole transport layer )

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a material for the hole transport layer. First, on the ITO layer (anode) formed on the organic substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ After vacuum deposition of -phenylbenzene-1,4-diamine (hereinafter abbreviated as "2-TNATA") to a thickness of 60 nm to form a hole injection layer, compound 1-1 of the present invention was added to the hole injection layer to a thickness of 60 nm A hole transport layer was formed by vacuum deposition with a furnace. Then, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as "CBP") as a host material on the hole transport layer, tris(2-phenylpyridine)-iridium (hereinafter "Ir(ppy) ₃ Abbreviated as ") was doped with a weight of 90:10 as a dopant material and vacuum deposited to a thickness of 30 nm to form a light emitting layer. Then, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinoleato)aluminum (hereinafter abbreviated as "BAlq") was vacuum deposited to a thickness of 10 nm on the light emitting layer. A hole blocking layer was formed, and tris(8-quinolinol) aluminum (hereinafter abbreviated as "Alq ₃ ") was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ Example 2] to [ Example 168] Green organic light emitting device ( Hole transport layer )

The point of using one of the compounds 1-2 to 1-56, 2-1 to 2-56, and 3-1 to 3-56 of the present invention described in Table 5 below instead of the compound 1-1 of the present invention as the hole transport layer material. Except for, an organic electroluminescent device was manufactured in the same manner as in Example 1.

[ Comparative example One]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound A was used instead of Compound 1-1 of the present invention as a material for the hole transport layer.

<Comparative compound A>

[ Comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound B was used instead of Compound 1-1 of the present invention as a material for the hole transport layer.

<Comparative compound B>

Electroluminescence (EL) characteristics by applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples 1 to 168 and Comparative Example 1 and Comparative Example 2 of the present invention with PR-650 of photoresearch Was measured, and the T95 life was measured using a life measurement equipment manufactured by McScience at a luminance of 5000 cd/m 2. The measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results of Table 5, it can be seen that the organic electroluminescent device using the compound of the present invention as a material for the hole transport layer exhibits relatively high efficiency and long life.

In other words, Comparative Compound B having a structure similar to the compound of the present invention than Comparative Compound A, which is NPB, exhibited superior device results in terms of driving voltage, efficiency and life, and the compound of the present invention substituted with deuterium rather than Comparative Compound B. Excellent device results were shown in terms of driving voltage, efficiency, and life. That is, the compound of the present invention exhibited a result of a device having a lower driving voltage, higher efficiency, and longer lifespan.

When substituted with deuterium, the zero point energy, that is, the energy of the ground state is lowered, and as the bond length of deuterium-carbon becomes shorter than that of hydrogen-carbon, the molecular hardcore volume Is reduced, thereby reducing electrical polarizability, and weakening intermolecular interaction, thereby increasing the volume of the thin film. These characteristics can create an amorphous state, that is, the effect of lowering the crystallinity of the thin film, and such amorphous state can reduce the grain boundary through isotropic and homogeneous properties, thereby reducing the electric charge. It was confirmed that the flow of, that is, the hole mobility, can be accelerated. Therefore, it is judged that the substitution of deuterium played a very effective role in realizing an amorphous state, which is absolutely necessary in order to increase the OLED lifetime and driving characteristics.

This suggests that even though they have a similar structure, the properties of the compound may change significantly as deuterium is substituted.

[ Example 167] Red organic light emitting device ( Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material. First, a hole injection layer was formed by vacuum depositing 2-TNATA to a thickness of 60 nm on an ITO layer (anode) formed on an organic substrate, and then 4,4-bis[N-(1-naphthyl) on the hole injection layer. )-N-phenylamino]biphenyl (hereinafter abbreviated as “NPD”) was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, after vacuum deposition of Compound 1-1 of the present invention to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer, CBP as a host material on the light emission auxiliary layer, bis-(1-phenylisoquinolyl)iridium ( Ⅲ) Acetylacetonate (hereinafter abbreviated as "(piq) ₂ Ir(acac)") as a dopant material was doped with a weight of 95:5 and vacuum deposited to a thickness of 30 nm to form a light emitting layer. Subsequently, BAlq was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer, and Alq ₃ was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[ Example 168] to [ Example 180] Red organic light emitting device ( Light-emitting auxiliary layer )

The point of using one of the compounds 1-2 to 1-4, 2-5 to 2-8, and 3-41 to 3-44 of the present invention described in Table 6 below instead of the compound 1-1 of the present invention as the light-emitting auxiliary layer material Except for, an organic electroluminescent device was manufactured in the same manner as in Example 167.

[ Comparative example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 167, except that the light emission auxiliary layer was not formed.

[ Comparative example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 167, except that Comparative Compound A was used instead of Compound 1-1 of the present invention as a light emitting auxiliary layer material.

[ Comparative example 5]

An organic electroluminescent device was manufactured in the same manner as in Example 167, except that Comparative Compound B was used instead of Compound 1-1 of the present invention as a light emitting auxiliary layer material.

Electroluminescence (EL) characteristics by applying a forward bias direct current voltage to the organic electroluminescent devices manufactured according to Examples 167 to 180 and Comparative Examples 3 to 5 of the present invention with PR-650 of photoresearch Was measured, and the T95 life was measured using a life measuring equipment manufactured by McScience at a luminance of 2500 cd/m 2. The measurement results are shown in Table 6 below.

[Table 6]

As can be seen from the results of Table 6, it can be seen that the organic electroluminescent device using the compound of the present invention as a material for the light emission auxiliary layer significantly improves the light emission efficiency and lifespan.

In other words, it can be seen that the efficiency and lifespan are improved when the light emission auxiliary layer is used than when the light emission auxiliary layer is not used, and the compound of the present invention in which deuterium is substituted rather than the comparative compounds A and B not substituted with deuterium is used. It was confirmed that the device used as the material for the auxiliary light emitting layer exhibited higher efficiency and lifetime. This is a result shown by substitution of deuterium as described in the results of Table 5, and this suggests that even though it has a similar structure, the properties of the compound may be remarkably changed as deuterium is substituted.

The above description is only illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100: organic electric device 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (10)

Compound represented by the following formula (1):
<Formula 1>

In Formula 1,
Ar ¹ and Ar ² are each independently a C ₆ ~ C ₁₈ aryl group; And O, N, S, Si and P is selected from the group consisting of a C ₂ ~ C ₃₀ heterocyclic group containing at least one heteroatom, wherein the aryl group does not include a fluorenyl group,
m and n are each an integer of 0 to 7, m+n is an integer of 1 or more,
R ¹ and R ² are each independently hydrogen or deuterium, wherein at least one of R ¹ or R ² is deuterium, and when R ¹ is deuterium, m is an integer of 1 or more, and when R ² is deuterium, n is 1 or more Is an integer,
The aryl group and the heterocyclic group are each deuterium; Of C ₆ ~ C ₂₀ Aryl group; A C ₆ ~ C ₂₀ aryl group substituted with deuterium; And C ₂ ~ C ₂₀ It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group. The method of claim 1,
Formula 1 is a compound characterized in that represented by one of the following Formulas 2 to 4:
<Formula 2>

<Formula 3>

<Formula 4>

In Formulas 2 to 4, Ar ¹ , Ar ² , R ¹ , R ² , m and n are the same as those defined in claim 1, and D represents deuterium. The method of claim 1,
The compound represented by Formula 1 is a compound characterized in that one of the following compounds:

. delete In the organic electric device comprising a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode,
The organic electroluminescent device, characterized in that the organic material layer comprises the compound of any one of claims 1 to 3. The method of claim 5,
The compound is an organic electric device, characterized in that included in at least one of the hole injection layer, the hole transport layer, the light emission auxiliary layer and the light emitting layer of the organic material layer. The method of claim 5,
An organic electric device further comprising a light efficiency improvement layer formed on one surface of the first electrode opposite to the organic material layer or on one surface of the second electrode opposite to the organic material layer. The method of claim 5,
The organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process. A display device comprising the organic electric device of claim 5; And
Electronic device comprising a; a control unit for driving the display device. The method of claim 9,
The organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a single color or white lighting device.

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