KR20150117399A - 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 light-emitting efficiency, stability, and lifespan of an element, an organic electronic element using same and an electronic device thereof.

Description

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

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

Flat panel display devices are playing a very important role in supporting a high image information society centered on the Internet, which is experiencing rapid growth in recent years. Particularly, the organic electroluminescent device which can be driven by a low voltage in a self-emission type has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, , And advantageous in terms of power consumption. In addition, the response speed is fast and the color reproduction range is wide, and attention has been paid as a next generation display device.

In general, an organic EL element 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 order. At this time, the organic thin film may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer , EIL). In addition, an electron blocking layer (EBL) or a hole blocking layer (HBL) may be further included in the light emitting layer. When an electric field is applied to the organic EL device having such a structure, holes are injected from the anode and electrons are injected from the cathode. The injected holes and electrons are recombined in the light emitting layer through the hole transporting layer and the electron transporting layer, . The luminescent exciton thus formed emits light while transitioning to ground states. At this time, a luminescent dye (guest) is doped in the luminescent layer (host) to increase the efficiency and stability of the luminescent state.

In order to utilize such an organic electric device in various display media, the lifetime of the device is important, and various studies are currently under way to increase the lifetime of the organic electric device.

An object of the present invention is to provide an amine compound substituted with deuterium which can improve the low driving voltage and lifetime of the device, an organic electric device using the same, and an electronic device therefor.

In one aspect, the invention provides compounds represented by the formula:

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

By using the compound according to the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and lifetime of the device.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference symbols as possible even if they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

Various studies have been conducted on organic materials inserted into a buffer layer such as a hole transporting layer or a light emitting auxiliary layer for an excellent lifetime characteristic of an organic electroluminescent device. For this purpose, a high hole transporting property from an anode to an organic layer is given A hole injecting layer and a hole transporting layer material having high uniformity and low crystallinity when forming a thin film after deposition are required.

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

Particularly, it is urgently needed to overcome the problem of power consumption and lifetime as the panel size of a mobile phone or a tablet PC becomes larger.

However, it is difficult to simultaneously overcome the driving voltage and the lifetime as the hole transporting layer material. The reason is that in order to lower the driving voltage, most of the materials having a high hole transporting ability, that is, a material having a high hole mobility, have a planar structure rich in electrons. For example, naphthyl, fluorene and phenanthrene. However, when a compound having the above structure is introduced into a hole transporting material as a substituent, the hole mobility increases up to a certain number and the lifetime is also affected. However, in order to reach the low voltage driving target required in the present industry, If it is increased, the driving voltage can be lowered while driving at a lower voltage, but the result shows that the lifetime is rapidly deteriorated. The reason for this is that, in the case of molecules in which the electron-rich planar structures are excessively introduced, holes are trapped and stabilized between the plate-like structures when a constant current is continuously supplied during the evaluation of the device life, As the driving voltage increases to apply a constant current, the lifetime of the device is rapidly deteriorated. This is expressed by the following equation.

J = Space Charge limited current

ε = Permittibility

μ = Mobility Coefficient

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

V = Voltage

d = Thickness

When the number of free carriers decreases due to a trap phenomenon, the value of? Decreases. Therefore, in a current driven organic electroluminescent device requiring a constant current, the driving voltage rises, The results can be retrieved. Therefore, as described above, introduction of a certain number or more of the plate-like structure rich in electrons capable of increasing the hole mobility has an unfavorable effect on the lifetime, and thus there is little possibility of lowering the driving voltage by using it.

Therefore, in order to solve such a problem in the present invention, there is a method of using a material having a good lifetime and substituting an appropriate ratio of deuterium by a method capable of lowering a driving voltage without introducing a molecular structure of a plate- A method of lowering the driving voltage by a method is proposed.

According to the results of the present inventors, it was confirmed that the deuterium-substituted compound exhibited much thermodynamic behavior as compared with the unsubstituted compound. Among these thermal properties, when the iridium compound was substituted with deuterium, the characteristics varied depending on the difference in carbon, hydrogen, carbon, and deuterium bond lengths. Compared to the compound in which the deuterium compound was not substituted with deuterium, It is possible to obtain a higher luminous efficiency due to the weakening of the intermolecular Van der Waals force generated in accordance with the present invention.

In addition, when substituted by deuterium, the energy of the zero point energy, that is, the bottom state is lowered. As the bond length of deuterium-carbon is shorter than the bond length of hydrogen-carbon, the molecular hardcore volume It is possible to reduce the electrical polarizability and weaken the intermolecular interaction, thereby increasing the volume of the thin film. These characteristics are considered to be very effective for realizing the necessary amorphous state in order to lower the crystallinity of the thin film, that is, to make the amorphous state and to generally improve the lifetime and drive characteristics of the OLED.

However, a method of lowering the driving voltage by replacing with deuterium, that is, increasing the hole transporting mobility of the hole transporting material, has not been studied at present. In this study, various kinds of compounds are used Therefore, many experiments were carried out. In addition, when a thin film is formed from a compound substituted with deuterium, a film is formed in an amorphous glass state which can greatly affect the hole mobility of the thin film, and the amorphous glass state isotropic and homogeneous It is confirmed that the charge flow, that is, the hole mobility, can be accelerated by reducing the grain boundary through the homogeneous property.

The present invention will be described in more detail. An amine compound is used as a material having excellent lifetime. Particularly noteworthy is that the amine compound has excellent lifetime characteristics according to the present invention, but has a drawback that the driving voltage is increased. However, the prior art has not proved the effect of improvement on such a part, and the prior art which improves the driving characteristic through deuterium substitution at a specific position has not been reported yet.

As a result of research and development of such inventors, the present invention provides a compound having an amine group substituted with deuterium so as to meet the required characteristics of the organic material while maintaining excellent characteristics of the organic material layers of the organic electronic device.

As used in this specification and the appended claims, unless stated otherwise, the following terms have the following meanings:

The term " halo "or" halogen ", as used herein, unless otherwise indicated, is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

As used herein, the term "alkyl" or "alkyl group " refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, 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 stated.

The term "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced by a heteroatom.

The term "alkenyl group" or "alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

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

The term "alkenoyl group "," alkenoyl group ", "alkenyloxy group ", or" alkenyloxy group "as used in the present invention means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.

As used herein, the term "aryloxyl group" or "aryloxy group" refers to an aryl group attached to an oxygen radical and, unless otherwise stated, has a carbon number of 6 to 60, but is not limited thereto.

The terms "aryl group" and "arylene group ", as used in the present invention, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirobifluorene group.

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

Also, if prefixes are named consecutively, it means that the substituents are listed in the order listed first. For example, the arylalkoxy group means an alkoxy group substituted with an aryl group, the alkoxycarbonyl group means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, an alkenyl group substituted with an arylcarbonyl group means Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.

The term "heterocyclic group ", as used herein, unless otherwise specified, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, Aromatic rings. Adjacent functional groups may be combined and formed.

As used herein, the term "heteroatom " refers to N, O, S, P or Si unless otherwise stated.

The "heterocyclic group" may also include a ring containing SO ₂ in place of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

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

Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring of 3 to 60 carbon atoms or an aromatic ring of 6 to 60 carbon atoms or a heterocycle of 2 to 60 carbon atoms, or combinations thereof, Saturated or unsaturated ring.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

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

Unless otherwise indicated, the term "ether" used in the present invention refers to -RO-R 'wherein R or R' are each independently of the other hydrogen, an alkyl group of 1-20 carbon atoms, An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of 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 Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as follows: and wherein R ¹ may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.

1 is an illustration of an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Comprising an organic compound layer comprising a compound according to the present invention. In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, the remaining layers except the light emitting layer 150 may not be formed. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to the present invention may further include a protective layer or a light-efficiency-improving 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 may be a host or a dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, It can be used as a material. Preferably, the compound of the present invention may be used as the light emitting layer 150, the hole transporting layer 140 and / or the light emitting auxiliary layer 151.

On the other hand, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at any position even in the same core, the selection of the core and the combination of the sub- Especially when the optimum combination of energy level and T1 value between the organic layers, intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long lifetime and high efficiency can be achieved at the same time.

As described above, in order to solve the light emission problem in the hole transporting layer in recent organic electroluminescent devices, it is preferable that the light emitting auxiliary layer is formed between the hole transporting layer and the light emitting layer. It is necessary to develop different luminescent auxiliary layers. On the other hand, in the case of the light-emission-assisting layer, it is difficult to deduce the characteristics of the organic layer to be used even if a similar core is used because the relationship between the hole-transport layer and the light-emitting layer (host)

Accordingly, in the present invention, by forming the light emitting layer or the light emitting auxiliary layer using the compound represented by the general formula (1), the energy level and T1 value between each organic material layer, the mobility of the material, It is possible to simultaneously improve the lifetime and efficiency of the electric element.

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

In addition, the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. 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 electroluminescent device according to the present invention may be of a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down , And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light from the electroluminescent material. Can be applied to such WOLED.

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochrome or white illumination.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. The electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

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

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

[Chemical Formula 1]

In Formula 1, Ar ¹ and Ar ² are, independently of each other, a C ₆ to C ₁₈ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and 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 ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R ^a ) (R ^b ); 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- 3,5-triazine, and the like.

m and n are each an integer of 0 to 7, wherein 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, independently of each other, hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and 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 ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R ^a ) (R ^b ); Wherein at least one of R ¹ or R ² is deuterium.

L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A 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 a C ₂ to C ₆₀ heterocyclic group.

R ^a and R ^b are each independently a C ₆ to C ₆₀ aryl group; A 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 a C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P;

The aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxyl group, the aryloxyl group, the arylene group and the fluorenylene group may each be substituted with deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; C ₆ -C ₂₀ An aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ to C ₂₀ ; And an arylalkenyl group having from ₈ to ₂₀ carbon atoms.

Here, the aryl group may be an aryl group having 6 to 60 carbon atoms, preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms,

The heterocyclic group may be a heterocyclic group having 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably 26 to 20 carbon atoms,

The arylene group may be an arylene group having 6 to 60 carbon atoms, preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms,

The alkyl group may be an alkyl group having 1 to 60 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms.

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

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4, Ar ¹ , Ar ² , R ¹ , R ² , m and n may be defined as defined in Formula 1, and D means deuterium.

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

In another embodiment, the present invention provides a compound for an organic electroluminescent device represented by the general formula (1).

In another embodiment, the present invention provides an organic electronic device containing the compound represented by the above formula (1).

The organic electroluminescent device includes a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode. The organic material layer may include a compound represented by Formula 1, wherein Formula 1 is a hole injecting layer, a hole transporting layer, Or the light-emitting layer. That is, the compound represented by the formula (1) can be used as a material for the hole injection layer, the hole transport layer, the light emission assisting layer or the light emitting layer. Specifically, the present invention provides an organic electric device including one of the compounds represented by Chemical Formulas 2 to 4 in the organic material layer, more specifically, an organic electronic device including the compound represented by the individual chemical formula in the organic material layer do.

In another embodiment of the present invention, the light efficiency improving layer is formed on at least one side of the one side of the first electrode opposite to the organic layer, or one side of the one side of the second electrode opposite to the organic layer, And an organic electroluminescent device.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

Illustratively, the compounds according to the invention (Final Products) are prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but are not limited thereto.

<Reaction Scheme 1>

I. Sub  1 of Synthetic example

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

<Reaction Scheme 2>

One. Sub  1-2 Synthetic example

To a round bottom flask Sub 1-2-1 (1 eq.), Sub 1-2-2 (1 _{eq), Pd 2 (dba) 3} (0.05 eq.), PPh ₃ (0.1 equiv), NaO t -Bu (3 , And toluene (10.5 mL / Sub 1-2-1 1 mmol) are added thereto, and the reaction is allowed to proceed at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. Subsequently, the resulting organic material was subjected to silicagel column and recrystallization to obtain Sub 1-2.

(1) 1-2 (1) Synthesis Example

Sub 1-2-1 (1) (3.1 g, 20 mmol), Sub 1-2-2 (1) (2.9 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 3.6 g (yield: 82%) of 1-2 (1).

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

Sub 1-2-1 (2) (4.7 g, 20 mmol), Sub 1-2-2 (2) (3.0 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 4.4 g (yield: 72%) of 1-2 (12).

(3) Synthesis of 1-2 (19)

Sub 1-2-1 (3) (4.1 g, 20 mmol), Sub 1-2-2 (3) (2.9 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 4.6 g (yield: 85%) of 1-2 (19).

(4) Synthesis of 1-2 (29)

Sub 1-2-1 (4) (5.4 g, 20 mmol), Sub 1-2-2 (4) (3.0 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol), NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 4.7 g (yield: 70%) of 1-2 (29).

Examples of Sub 1-2 are shown below, but the present invention is not limited thereto, and their FD-MSs are shown in Table 1 below.

[Table 1]

2. Sub  1 of Synthetic example

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

(1) Synthesis Example of Sub 1 (1)

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 (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 6.8 g (yield: 76%) of Sub 1 (1).

(2) Synthesis Example of Sub 1 (15)

Sub-1-1 (6.2 g, 20 mmol), Sub 1-2 (15) (4.5 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) , NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 6.7 g (yield: 73%) of Sub 1 (1).

(3) Synthesis Example of Sub 1 (20)

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 (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.9 g of Sub 1 (20) (yield: 75%).

(4) Synthesis Example of Sub 1 (25)

Sub 1-1 (6.2 g, 20 mmol), Sub 1-2 (25) (4.5 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) , NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 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-MSs are shown in Table 2 below.

[Table 2]

II . Sub  2 of Synthetic example

Sub 2 of Reaction Scheme 1 can be synthesized by the reaction path of Reaction Scheme 3 below, but is not limited thereto.

<Reaction Scheme 3>

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

1. Synthesis Example of Sub 2 (4)

Sub 2-1 (1) (4.7 g, 20 mmol), Sub 2-2 (1) (4.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ , NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 6.2 g (yield: 83%) of Sub 2 (4).

2. Synthesis Example of Sub 2 (22)

Sub 2-1 (2) (4.9 g, 20 mmol), Sub 2-2 (2) (4.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ , NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 6.0 g (yield: 78%) of Sub 2 (22).

3. Synthesis Example of Sub 2 (25)

Sub 2-1 (3) (3.1 g, 20 mmol), Sub 2-2 (3) (4.5 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ , NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 4.7 g (yield: 78%) of Sub 2 (25).

4. Synthesis Example of Sub 2 (44)

Sub 2-1 (4) (5.7 g, 20 mmol), Sub 2-2 (4) (4.5 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ , NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 6.6 g (yield: 77%) of Sub 2 (44).

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

[Table 3]

III . The final product ( Final Product )of Synthetic example

Pd ₂ (dba) ₃ (0.05 eq.), PPh ₃ (0.1 eq.), NaO t- Bu (3 eq.), Toluene (10.5 mL / Sub 1mmol) was added thereto, and the reaction was allowed to proceed at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain final product.

1. Synthesis Example 1-4

Sub 9 (9.1 g, 20 mmol), Sub 2 (4) (7.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 11.7 g (yield: 78%) of 1-4.

2. Synthesis Example of 2-4

Sub 1 (1) (9.0 g, 20 mmol), Sub 2 (28) (7.6 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 11.8 g (yield: 79%) of 2-4.

3. Synthesis Example of 2-41

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

4. Synthesis Example of 3-4

Sub 9 (9.1 g, 20 mmol), Sub 2 (28) (7.6 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 11.9 g (yield: 79%) of 3-4.

5. Synthesis Example of 3-55

(9.2 g, 20 mmol), Sub 2 (39) (7.0 g, 20 mmol), Pd ₂ (dba) ₃ (0.9 g, 1 mmol), PPh ₃ (0.5 g, NaO t- Bu (5.8 g, 60 mmol) and toluene (210 mL) were added, and the mixture was refluxed at 100 ° C for 24 hours. ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 10.8 g (yield: 75%) of 3-55.

Meanwhile, the FD-MSs of the present invention compounds 1-1 to 1-56, 2-1 to 2-56, and 3-1 to 3-56 according to the above Synthesis Examples are shown in Table 4 below.

[Table 4]

Evaluation of manufacturing of organic electric device

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

An organic electroluminescent device was prepared according to a conventional method using the compound of the present invention as a hole transport layer material. First, N ¹ on the ITO layer (anode) formed on an organic substrate - (naphthalen-2-yl) -N 4, N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1 (hereinafter abbreviated as " 2-TNATA ") was vacuum-deposited to a thickness of 60 nm to form a hole injecting layer, and Compound 1-1 of the present invention was coated on the hole injecting layer to a thickness of 60 nm To form a hole transporting layer. Subsequently, tris (2-phenylpyridine) -iridium (hereinafter referred to as "Ir (ppy) ₃ ") was added to the hole transport layer as a host material, and 4,4'-N, N'-dicarbazole- Quot; as a dopant material) was doped in a weight ratio of 90:10, and vacuum evaporated to a thickness of 30 nm to form a light emitting layer. Subsequently, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as "BAlq") was vacuum deposited on the light emitting layer to a thickness of 10 nm (8-quinolinol) aluminum (hereinafter abbreviated as "Alq ₃ &quot;) was vacuum deposited on the hole blocking layer to a thickness of 40 nm 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. Thus, an organic electroluminescent device was manufactured.

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

The compounds 1-2 to 1-56, 2-1 to 2-56 and 3-1 to 3-56 of the present invention described in the following Table 5 were used instead of the compound 1-1 of the present invention as the hole transport layer material An organic electroluminescence device was prepared in the same manner as in Example 1.

[ Comparative Example  One]

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

&Lt; Comparative Compound A >

[ Comparative Example  2]

An organic electroluminescence device was prepared in the same manner as in Example 1, except that the following compound B was used instead of the compound 1-1 of the present invention as the hole transport layer material.

&Lt; Comparative Compound B >

A forward bias DC voltage was applied to the organic electroluminescent devices prepared in Examples 1 to 168 and Comparative Example 1 and Comparative Example 2 of the present invention, and electroluminescence (EL) characteristics were measured with a photoresearch PR-650 And T95 lifetime was measured by a life measuring device manufactured by Mac Science Inc. 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 confirmed that the organic electroluminescence device using the compound of the present invention as a material of the hole transport layer exhibits relatively high efficiency and long lifetime.

In other words, the comparative compound B having a structure similar to the compound of the present invention exhibited better device voltage in terms of driving voltage, efficiency and lifetime than the comparative compound A which is NPB, and the compound of the present invention This shows excellent device results in terms of driving voltage, efficiency and lifetime. That is, the compound of the present invention exhibited an improved efficiency and a longer lifetime while the driving voltage was lower.

In the case of substitution with deuterium, the zero point energy, that is, the energy of the bottom state is lowered, and as the bond length of deuterium-carbon is shorter than the bond length of hydrogen-carbon, the molecular hardcore volume Can be reduced, thereby reducing the electric polarizability and weakening the intermolecular interaction, so that the film volume can be increased. These characteristics can produce the effect of lowering the crystallinity of the thin film, that is, an amorphous state. The amorphous state reduces the grain boundaries through isotropic and homogeneous characteristics, That is, the hole mobility can be increased. Therefore, it is considered that the substitution of deuterium plays a very effective role in realizing the necessary amorphous state in order to improve OLED lifetime and driving characteristics.

This suggests that the properties of the compounds may vary significantly with deuterium substitution even though they have similar structures.

[ Example  167] Red organic light emitting device ( The light- )

Organic electroluminescent devices were prepared according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material. First, 2-TNATA was vacuum deposited on the ITO layer (anode) formed on the organic substrate to a thickness of 60 nm to form a hole injection layer, and 4,4-bis [N- (1-naphthyl ) -N-phenylamino] biphenyl (hereinafter abbreviated as "NPD") was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Subsequently, Compound 1-1 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light-emission-assisting layer, and bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter abbreviated as "(piq) ₂ Ir (acac)") as a dopant was doped at a weight ratio of 95: 5 and vacuum evaporated to a thickness of 30 nm to form a light emitting layer. Subsequently, BAlq was vacuum deposited on the light emitting layer to form a hole blocking 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 transporting 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. Thus, an organic electroluminescent device was manufactured.

[ Example  168] to [ Example  180] red organic light emitting device The light- )

Instead of Compound 1-1 of the present invention as the luminescent auxiliary layer material, 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 was used , An organic electroluminescent device was prepared in the same manner as in Example 167. [

[ Comparative Example  3]

An organic EL device was prepared in the same manner as in Example 167 except that no light-emitting auxiliary layer was formed.

[ Comparative Example  4]

An organic EL device was prepared in the same manner as in Example 167, except that the compound A was used in place of the compound 1-1 of the present invention as the luminescent auxiliary layer material.

[ Comparative Example  5]

An organic EL device was prepared in the same manner as in Example 167, except that the compound B was used instead of the compound 1-1 of the present invention as the luminescent auxiliary layer material.

Electroluminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 167 to 180 and Comparative Examples 3 to 5 of the present invention And the T95 lifetime was measured using a life measuring device manufactured by Mac Science Inc. 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 shown in Table 6, the organic electroluminescence device using the compound of the present invention as the material of the light-emitting auxiliary layer remarkably improves the luminous efficiency and lifetime.

In other words, it can be seen that the efficiency and lifetime are improved when the luminescent auxiliary layer is used as compared with the case where the luminescent auxiliary layer is not used. It can be confirmed that the compounds of the present invention in which deuterium is substituted for the compounds A and B, It was confirmed that the device used as the material of the light emission assisting layer exhibited higher efficiency and a longer lifetime. This results from the substitution of deuterium as described in the results of Table 5, suggesting that the characteristics of the compound may be significantly changed as deuterium is substituted even though it has a similar structure.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

100: organic electric element 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)

A compound represented by the following formula (1).
&Lt; Formula 1 >

[In the above formula (1)
Ar ¹ and Ar ² are, independently of each other, a C ₆ to C ₁₈ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and 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 ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R ^a ) (R ^b );
m and n are each an integer of 0 to 7, wherein m + n is 1 or more,
R ¹ and R ² are, independently of each other, hydrogen; heavy hydrogen; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and 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 ; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ ; And -L'-N (R ^a ) (R ^b ), wherein at least one of R ¹ or R ² is deuterium,
L 'is a single bond; An arylene group having ₆ to ₆₀ carbon atoms; A 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 a C ₂ to C ₆₀ heterocyclic group,
R ^a and R ^b are each independently a C ₆ to C ₆₀ aryl group; A 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 ; Is selected from the group consisting of; and O, N, S, Si, and a heterocyclic group of C ₂ ~ C ₆₀ containing at least one hetero atom of the P
Each of the aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxyl group, the aryloxy group, the arylene group and the fluorenylene group may be substituted with deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; C ₆ -C ₂₀ An aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ to C ₂₀ ; And an arylalkenyl group having from ₈ to ₂₀ carbon atoms. The method according to claim 1,
Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;
(2)

(3)

&Lt; Formula 4 &gt;

(Wherein Ar ¹ , Ar ² , R ¹ , R ² , m and n are as defined in claim 1, and D is deuterium) The method according to claim 1,
Lt; / RTI &gt; is one of the following compounds.

An organic electric device comprising a compound according to any one of claims 1 to 3. 5. The method of claim 4,
A first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode and containing the compound. 6. The method of claim 5,
Wherein the compound is contained in at least one of the hole injection layer, the hole transport layer, the light emission assisting layer and the light emitting layer of the organic material layer. 6. The method of claim 5,
Further comprising a light-efficiency-improvement layer formed on at least one side of the one surface of the first electrode and the second electrode opposite to the organic material layer. 6. The method of claim 5,
Wherein 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 including the organic electroluminescent device of claim 4; And
And a control unit for driving the display device. 10. The method of claim 9,
Wherein the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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