KR102178087B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

A compound represented by Formula 1 is disclosed. Further, an organic electric device including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode is disclosed, wherein the organic material layer includes a compound represented by Formula 1. When the compound represented by Formula 1 is included in the organic material layer, luminous efficiency, stability, and lifespan may be improved.

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.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electric device using an organic light emission phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electronic device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as an organic material layer in an organic electric device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. And the light-emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and according to the light emitting mechanism, it can be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron. have. In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary to realize better natural colors according to the light-emitting color.

Currently, the portable display market is increasing in size as a large-area display, and for this reason, more power consumption than the power consumption required by the existing portable display is required. Therefore, power consumption has become a very important factor for portable displays that have a limited power supply source such as a battery, and efficiency and life issues must also be solved.

Efficiency, lifespan, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, the crystallization of organic materials caused by Joule heating during driving decreases. It shows a tendency to increase the lifespan.

In general, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated by recombination. However, in a general organic electroluminescent device, since hole mobility is faster than electron mobility, excitons generated in the light emitting layer pass to the electron transport layer, resulting in charge unbalance in the light emitting layer. Resulting in light emission at the interface of the electron transport layer. When light is emitted at the interface of the electron transport layer, there is a problem that the color purity and efficiency of the organic electronic device are deteriorated. In particular, when the organic electronic device is manufactured, the high temperature stability is deteriorated and the life of the organic electronic device is shortened.

Therefore, the electron transport material that has high temperature stability and high electron mobility (within the range of driving voltage of a full device blue device) and improves the hole blocking ability with a high T ₁ value Development is needed. ( Adv. Funct . Mater . 2013, 23 , 1323)

On the other hand, in order to solve the problem of the existing hole transport layer material in the recent organic electroluminescent device, a light emitting auxiliary layer is formed between the hole transport layer and the light emitting layer, and this light emitting auxiliary layer has a hole mobility and high T ₁ to have an appropriate driving voltage. Values and materials with wide bandgap should be used.

However, simply improving each of these organic material layers cannot maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.

In other words, in order to fully exhibit the excellent characteristics of the organic electroluminescent device, materials that make up the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and light-emitting auxiliary layer materials, are stable. Supported by an efficient material must precede, and in particular, there is an urgent need to develop a material capable of effectively achieving charge balance through a combination of materials such as an electron transport layer, a hole transport layer, and a light emission auxiliary layer.

An object of the present invention is to provide a compound capable of improving luminous efficiency, stability, and lifetime 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 and high heat resistance of the device can be achieved, and color purity and lifespan of the device can be 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 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”. In addition, when a component such as a layer, film, region, or plate is said to be "on" or "on" another component, it is not only "directly over" another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is "directly above" another part, it means that there is no other part in the middle.

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 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 term "alkoxy group" or "alkyloxy group" used in the present invention refers to an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and 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 term "fluorenyl group" or "fluorenylene group" as used in the present invention means a monovalent or divalent functional group in which R, R'and R" are all hydrogen in each of the following structures, unless otherwise specified, " Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R'are bonded to each other and the carbon to which they are bonded It includes the case of forming a compound by spy together.

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, the aryl group or the arylene group includes a monocyclic type, a cyclic conjugate, several fused ring systems, and a spiro compound.

The term "heterocyclic group" as used in the present invention includes not only an aromatic ring such as a "heteroaryl group" or a "heteroarylene group", but also a non-aromatic ring, and unless otherwise stated, each carbon number including one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P, or Si unless otherwise specified, and the heterocyclic group is a monocyclic type including a heteroatom, a ring conjugate, a conjugated ring system, spy It means a compound and the like.

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.

The term "ring" as used in the present invention includes monocyclic and polycyclic rings, including hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and non-aromatic rings.

The term "polycyclic" used in the present invention includes ring assemblies such as biphenyl, terphenyl, etc., several fused ring systems, and spiro compounds, and includes not only aromatic but also non-aromatic, hydrocarbon Rings of course include heterocycles containing at least one heteroatom.

The term "ring assemblies" as used in the present invention refers to two or more ring systems (single ring or fused ring system) directly connected to each other through a single bond or a double bond, and direct It means that the number of linkages is one less than the total number of ring systems in this compound. In the ring aggregate, the same or different ring systems may be directly linked to each other through a single bond or a double bond.

The term "conjugated multiple ring systems" as used in the present invention refers to a fused ring form that shares at least two atoms, and includes a form in which a ring system of two or more hydrocarbons is fused and at least one heteroatom And at least one conjugated heterocyclic system. Several such fused ring systems may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings.

The term "spiro compound" used in the present invention has a'spiro union', and the spiro linkage refers to a connection made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It is called a compound.

In addition, when prefixes are named consecutively, it means that 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 alkoxycarbonyl group, it means a carbonyl group substituted with an alkoxy group, and in the case of an arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where The arylcarbonyl group is a carbonyl group substituted with an aryl group.

In addition, unless explicitly stated otherwise, the term "substituted" in the term "substituted or unsubstituted" used in the present invention means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, 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 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. At this time, at least one of these layers may be omitted, or 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. You could do it.

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 light emitting layer 150, a light efficiency improvement layer, a light emission auxiliary layer, etc. It could be used as a material for For example, the compound of the present invention may be used as a material for the hole transport layer 140, the light emission auxiliary layer 151, and/or the electron transport layer 160.

On the other hand, even with the same core, the band gap, electrical properties, and interfacial properties 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 important. Long life and high efficiency can be achieved at the same time when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.

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 emission auxiliary layer between the hole transport layer and the light emitting layer, corresponding to each light emitting layer (R, G, B). Thus, it is necessary to form 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.

Accordingly, by forming an electron transport layer using the compound according to Formula 1 or 1a of the present invention, and/or forming a hole transport layer and/or a light emission auxiliary layer with the compound according to Formula 2 of the present invention, the energy level between each organic material layer (level ) And T ₁ values, and the intrinsic properties (mobility, interfacial properties, etc.) of the material can be optimized to simultaneously improve the life and efficiency of the organic electric device.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a deposition method, and each layer may be formed using a deposition method such as PVD or CVD. The organic electroluminescent device according to the present invention forms an anode 120 by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 130 and a hole transport layer 140 thereon. ), an organic material layer including the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170 may be formed, and then a material that can be used as the cathode 180 may be deposited thereon.

In addition, the organic material layer is a solution process or a solvent process using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, It may be manufactured with fewer layers by a method such as 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 (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a single color or 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, each symbol may be defined as follows.

Ar ¹ and R ¹ are each independently an aryl group or a fluorenyl group of C ₆ -C ₂₄ , m is an integer of 0-4, and when m is 2 or more, R ¹ is the same as or different from each other.

Preferably, Ar ¹ may be a substituted or unsubstituted C ₆ -C ₁₈ aryl group, and preferably substituted or unsubstituted C ₆ , C ₁₀ , C ₁₂ , C ₁₄ , C ₁₅ , C ₁₆ or It may be a C ₁₈ aryl group, and is preferably a methyl or deuterium substituted or unsubstituted phenyl group, deuterium substituted or unsubstituted biphenylyl group, naphthyl group, m- or p -terphenylyl group, anthryl group, It may be a phenanthryl group, a pyrenyl group, or 9,9-dimethyl-9 H -fluorenyl group.

Preferably m may be 0 to 2, preferably R ¹ may be a phenyl group.

Preferably, when Ar ¹ and R ¹ are an aryl group or a fluorenyl group, they are deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, C ₁ -C ₂₀ alkyl group. Group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₆ -C ₂₀ aryl group, substituted with deuterium C ₆ -C ₂₀ aryl group, fluorenyl group, C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P, C ₃ -C ₂₀ It may be optionally further substituted with one or more substituents selected from the group consisting of a cycloalkyl group of, a C ₇ -C ₂₀ arylalkyl group, and a C ₈ -C ₂₀ arylalkenyl group.

In Formula 1, L ¹ is a single bond, C ₆ -C ₆₀ arylene group, fluorenylene group, C ₂ -including at least one hetero atom selected from the group consisting of O, N, S, Si and P It may be selected from the group consisting of a heterocyclic group of C ₆₀ , a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ , and combinations thereof.

Preferably, L ¹ may be a C ₁ -C ₁₈ aryl group, a C ₅ -C ₁₃ heterocyclic group, or a combination thereof, and preferably among those represented by the following L-1 to L-8 It can be one.

In the L-1 to L-8, Q ¹ to Q ³ are each independently CR ^a or N, and Q ⁴ is S, O or CR ^b R ^c to be. In addition, R ^a , R ^b and R ^c are each independently at least one heteroatom selected from the group consisting of hydrogen, deuterium, C ₆ -C ₆₀ aryl group, fluorenyl group, O, N, S, Si and P C ₂ -C ₆₀ heterocyclic group, C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring fused ring group, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ alkene Diary, it is selected from the group consisting of a C ₂ -C ₂₀ alkynyl group, a C ₁ -C ₃₀ alkoxy group, and a C ₆ -C ₃₀ aryloxy group.

In addition, preferably, L ¹ is a methyl-substituted or unsubstituted phenylene group, naphthylene group, biphenylene group, anthrylene group, phenanthrylene group, triphenylenylene group, pyrenylene group, pyridylene group, quinolylene group , It may be a combination of a quinolylene group and a phenylylene group, a combination of a pyridylene group and a phenylene group, a dibenzothienylene group, a phenanthrolylene group, or a phenanthridylene group.

Preferably, L ¹ is heavy hydrogen, a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, an alkylthio import of C ₁ -C _20, alkoxy group of C ₁ -C _20, C ₁ alkyl group -C _20, C ₂ -C ₂₀ alkene group, an aryl group of C ₆ -C ₂₀ substituted alkynyl, aryl, C ₆ -C ₂₀ heavy hydrogen of the C ₂ -C _20, fluorene group, C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, And it may be optionally further substituted with one or more substituents selected from the group consisting of C ₈ -C ₂₀ arylalkenyl group.

R ² and R ³ are independently of each other C ₆ -C ₆₀ of C ₂ -C ₆₀ containing at least one heteroatom selected from the group consisting of aryl group, fluorenyl group, O, N, S, Si and P It may be selected from the group consisting of a heterocyclic group, a fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring, and combinations thereof.

또는

일 수 있으며, 또한 바람직하게는 하기 A-1 내지 A-23으로 표시되는 것 중 하나일 수 있다.Preferably R ² and R ³ are

or

It may be, and also preferably one of those represented by the following A-1 to A-23.

Meanwhile, the R ¹² and R ¹³ are each independently i) at least one heteroatom selected from the group consisting of deuterium, halogen, C ₆ -C ₆₀ aryl, fluorenyl, O, N, S, Si, and P C ₂ -C ₆₀ heterocyclic group, C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring fused ring group, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ alkene Diary, selected from the group consisting of a C ₂ -C ₂₀ alkynyl group, a C ₁ -C ₃₀ alkoxy group, and a C ₆ -C ₃₀ aryloxy group, or ii) adjacent groups are bonded to each other to at least one ring In this case, R ¹² and R ¹³ that do not form a ring are the same as defined in i) above. The ring formed at this time may be monocyclic or polycyclic.

Further, n and o are each independently an integer of 0 to 5, when n is an integer of 2 or more, R ¹² may be the same as or different from each other, and when o is an integer of 2 or more, R ¹³ may be the same or different from each other.

Preferably, the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group of R ¹² and R ¹³ are each independently deuterium, halogen, silane group, siloxane group, boron group, a germanium group, a cyano group, a nitro group, C ₁ -C ₂₀ coming of the alkylthio, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl group of, C ₂ a -C ₂₀ alkynyl, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, fluorene group, O, N, S, at least one selected from the group consisting of Si and P of At least one selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group including a heteroatom, a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, and a C ₈ -C ₂₀ arylalkenyl group It may be optionally further substituted with a substituent.

Preferably, Formula 1 may be represented by the following Formula 1a.

<Formula 1a>

In Formula 1a, Ar ¹ , R ¹ , L1 and m are the same as defined in Formula 1.

In addition, R ¹² and R ¹³ are each independently i) at least one heteroatom selected from the group consisting of deuterium, halogen, C ₆ -C ₆₀ aryl, fluorenyl, O, N, S, Si and P Containing C ₂ -C ₆₀ heterocyclic group, C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring fused ring group, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ alkenyl group , C ₂ -C ₂₀ alkynyl group, C ₁ -C ₃₀ alkoxy group, and C ₆ -C ₃₀ aryloxy group selected from the group consisting of, or ii) adjacent groups are bonded to each other to at least one monocyclic or Can form a polycyclic ring, wherein R ¹² and R ¹³ which do not form a ring are the same as defined in i) above, n and o are each independently an integer of 0 to 5, n is an integer of 2 or more In case R ¹² is the same as or different from each other, when o is an integer of 2 or more, R ¹³ is the same or different from each other.

Preferably, the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group of R ¹² and R ¹³ are each independently deuterium, halogen, silane group, siloxane group, boron group, a germanium group, a cyano group, a nitro group, C ₁ -C ₂₀ coming of the alkylthio, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl group of, C ₂ a -C ₂₀ alkynyl, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, fluorene group, O, N, S, at least one selected from the group consisting of Si and P of At least one selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group including a heteroatom, a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, and a C ₈ -C ₂₀ arylalkenyl group It may be optionally further substituted with a substituent.

또는

는 상기 A-1 내지 A-23으로 표시되는 것 중 하나일 수 있다.In addition, preferably, in Formula 2,

or

May be one of those represented by A-1 to A-23.

Specifically, the compound represented by Formula 1 or 1a 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 or 1a.

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

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 or Formula 1a, and the compound represented by Formula 1 or Formula 1a is the organic material layer. It may be contained in at least one of the electron transport layer and the light emitting layer. That is, the compound represented by Formula 1 or 1a may be used as a material for an electron transport layer or a light emitting layer.

Preferably, an organic electric device including one of Compounds 1-1 to 1-84 is provided in the organic material layer.

Preferably, the compound contained in the organic material layer may be one type alone or a mixture of two or more represented by Chemical Formula 1 or 1a. For example, of the organic material layer, the electron transport layer or the light emitting layer may be formed of compound 1-1 alone, or may be formed of a mixture of compound 1-1 and compound 1-2.

In another embodiment, the organic material layer of the present invention includes an electron transport layer, an emission layer, an emission auxiliary layer, and a hole transport layer, the emission auxiliary layer is formed between the hole transport layer and the emission layer, and the electron transport layer is represented by Formula 1 or 1a. It contains a compound represented by, and at least one of the hole transport layer and the light emission auxiliary layer contains a compound represented by the following formula (2) independently of each other.

<Formula 2>

In Formula 2, Ar ² and Ar ³ are C ₆ -C ₆₀ independently of each other including at least one heteroatom selected from the group consisting of aryl group, fluorenyl group, O, N, S, Si and P ₂ -C ₆₀ heterocyclic group, C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring fused ring group, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ It is selected from the group consisting of an alkynyl group of -C ₂₀ , an alkoxy group of C ₁ -C ₃₀ , and an aryloxy group of C ₆ -C ₃₀ .

In addition, Ar ⁴ is the following formula 2a or 2b.

<Formula 2a> <Formula 2b>

In Formulas 2a and 2b, X is NR ^d , O, S, or CR ^e R ^f , wherein R ^d to R ^f are independently of each other C ₆ -C ₆₀ aryl group, fluorenyl group, O, N, S, Si, and group of C ₂ -C ₆₀ containing at least one heteroatom selected from the group consisting of P heterocycle groups fused ring of an aromatic ring of C ₃ -C ₆₀ aliphatic ring with C ₆ -C _60, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₃₀ alkoxy group, and C ₆ -C ₃₀ aryloxy group selected from the group consisting of , R ^e and R ^f may combine with each other to form a spy compound.

In addition, C ₂ -C ₆₀ hetero containing at least one hetero atom selected from the group consisting of L ² single bond, C ₆ -C ₆₀ arylene group, fluorenylene group, O, N, S, Si, and P It may be selected from the group consisting of a cyclic group, a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ , and combinations thereof, L ³ is an arylene group of C ₆ -C ₆₀ , Fluorenylene group, C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P, C ₃ -C ₆₀ aliphatic ring and C ₆ -C It may be selected from the group consisting of a fused ring group of ₆₀ aromatic rings, and combinations thereof.

Preferably, L ² and L ³ are independently of each other deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, C ₁ -C ₂₀ alkylthio group, C ₁ -C ₂₀ Alkoxy group of, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ aryl substituted with deuterium Group, a fluorenyl group, a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C ₃ -C ₂₀ cycloalkyl group, C _7- It may be optionally further substituted with one or more substituents selected from the group consisting of C ₂₀ arylalkyl group, and C ₈ -C ₂₀ arylalkenyl group,

In addition, in Formulas 2a and 2b, R ⁴ to R ⁷ are i) independently of each other as deuterium, tritium, halogen, C ₆ -C ₆₀ aryl group, fluorenyl group, O, N, S, Si and P C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of, a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ , C ₁ -C ₅₀ Alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₃₀ alkoxy group, and C ₆ -C ₃₀ aryloxy group selected from the group consisting of, or ii) neighboring Groups are bonded to each other to form at least one ring, wherein the group not forming a ring is the same as defined in i), p, r, and s are each an integer of 0 to 4, and q is of 0 to 3 Is an integer, and when each of them is an integer of 2 or more, each of R ⁴ to R ⁷ is the same as or different from each other.

Preferably, Ar ² , Ar ³ , R ⁴ to R ⁷ In the case of each of an aryl group, a fluorenyl group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group or an aryloxy group, each of them is independently of each other deuterium, halogen, silane group, siloxane group, boron group, a germanium group, a cyano group, a nitro group, C ₁ -C ₂₀ coming of the alkylthio, C ₁ -C ₂₀ alkoxy group, an alkenyl group, a C ₂ C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ a- for C ₂₀ alkynyl, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, fluorene group, O, N, S, at least one heteroatom selected from the group consisting of Si and P One or more substituents selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group containing an atom, a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, and a C ₈ -C ₂₀ arylalkenyl group Can be substituted with

Specifically, Formula 2 may be one of the following compounds.

Meanwhile, the organic material layer may be 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.

In another embodiment of the present invention, the present invention provides a display device including an organic electric device including an organic material layer containing a compound according to the present invention, and an electronic device including a controller for controlling the display device. In this case, the organic electric device may be one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a single color or white lighting device.

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

Synthesis example

The compound (final product) represented by Formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

I. Synthesis of Formula 1

The compound (final product) represented by Formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

<Reaction Scheme 1>

(R ¹ to R ³ , Ar ¹ , L ¹ , m, n and o are the same as defined in Formula 1a.)

One. Sub Synthesis of 1

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

<Reaction Scheme 2>

Synthesis examples of specific compounds belonging to Sub 1 are as follows.

(One) Sub 1-1 Synthesis example

<Reaction Scheme 3>

Sub 1-I-1 synthesis

The starting material 2-aminobenzoic acid (101.51 g, 0.7402 mol) was added to a round bottom flask with urea (311.19 g, 5.1813 mol) and stirred at 160 °C. After confirming the reaction by TLC, it was cooled to 100 °C, H ₂ O (500ml) was added, and the mixture was stirred for 1 hour. When the reaction was completed, the resulting solid was filtered under reduced pressure, washed with water, and dried to obtain 97.22 g (yield: 81%) of the product.

Sub One- II -1 synthesis

Sub 1-I-1 (97.22 g, 0.5996 mol) obtained in the above synthesis was added to a round bottom flask and dissolved in POCl ₃ (400ml) at room temperature, and then N , N- Diisopropylethylamine (193.72 g, 1.4989 mol) was slowly added dropwise. Then, it was stirred at 90 °C. After the reaction was completed, ice water (1000ml) was added and then stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to obtain 102.63 g (yield: 86%) of the product.

Sub One- III -1 synthesis

Sub 1-II-1 (69.13 g, 0.3473 mol) and 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (70.88 g, 0.3473 mol) obtained in the above synthesis were added to a round bottom flask. And dissolve in THF (770ml) and H ₂ O (385ml), and then K ₂ CO ₃ (144.01 g, 1.042 mol), Pd(PPh ₃ ) ₄ (16.05 g, 0.0139 mol) was added and stirred at 90 ^° C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 55.17 g (yield: 66%) of the product.

Sub 1-1 synthesis

Sub 1-III-1 (25.02 g, 0.104 mol) and 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (34.31 g) obtained in the above synthesis , 0.104 mol) in a round bottom flask and dissolved in THF (230ml) and H ₂ O (115ml), and then K ₂ CO ₃ (43.1 g, 0.3119 mol), Pd(PPh ₃ ) ₄ (4.8 g, 0.0042 mol) And stirred at 70 ^o C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 19.52 g (yield: 46%) of the product.

(2) Sub 1-20 Synthesis example

<Reaction Scheme 4>

Sub One- III -20 synthesis

Sub 1-II-1 (29.99 g, 0.1507 mol) obtained in the above synthesis 4,4,5,5-tetramethyl-2-(phenanthren-9-yl)-1,3,2-dioxaborolane (45.83 g, 0.1507 mol) mol), K ₂ CO ₃ (62.47 g, 0.452 mol), Pd(PPh ₃ ) ₄ (6.96 g, 0.006 mol), THF (340 ml), H ₂ O (170 ml) were prepared by using the Sub 1-III-1 synthesis method, 35.95 g (yield: 70%) of the product. Got it.

Sub 1-20 synthesis

1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (34.81 g) in Sub 1-III-20 (35.95 g, 0.1055 mol) obtained in the above synthesis. , 0.1055 mol), K ₂ CO ₃ (43.74 g, 0.317 mol), Pd(PPh ₃ ) ₄ (4.88 g, 0.0042 mol), THF (230ml), H ₂ O (115ml) by the Sub 1-1 synthesis method Using the product, 28.42 g (yield: 53%) was obtained.

(3) Sub 1-32 Synthesis example

<Reaction Scheme 5>

3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (38.56 g) in Sub 1-III-1 (28.04 g, 0.1165 mol) obtained in the above synthesis. , 0.1165 mol), K ₂ CO ₃ (48.3 g, 0.3495 mol), Pd(PPh ₃ ) ₄ (5.38 g, 0.0047 mol), THF (260ml), H ₂ O (130ml) was added to the Sub 1-1 synthesis method. Using the product, 20.03 g (yield: 42%) was obtained.

(4) Sub 1-46 Synthesis example

<Reaction Scheme 6>

Sub 1-I-46 synthesis

The starting material, 3-amino-[1,1'-biphenyl]-4-carboxylic acid (19.46 g, 0.0913 mol), urea (38.37 g, 0.6388 mol), H ₂ O (46 ml) was added to the Sub 1-I- One Product 16.96 g (yield: 78%) was obtained using a synthetic method.

Sub One- II -46 synthesis

POCl ₃ (50ml), N,N-Diisopropylethylamine (23 g, 0.178 mol) in Sub 1-I-46 (16.96 g, 0.0712 mol) obtained in the above synthesis was added to the product 17.43 using the Sub 1-II-1 synthesis method. g (yield: 89%) was obtained.

Sub One- III -46 synthesis

Sub 1-II-46 (17.43 g, 0.0634 mol) obtained in the above synthesis 4,4,5,5-tetramethyl-2-(phenanthren-9-yl)-1,3,2-dioxaborolane (19.27 g, 0.0634 mol), K ₂ CO ₃ (26.27 g, 0.1901 mol), Pd(PPh ₃ ) ₄ (2.93 g, 0.0025 mol), THF (140ml), H ₂ O (70ml) was added to the product 17.7 g (yield: 67%) using the Sub 1-III-1 synthesis method Got it.

Sub 1-46 synthesis

Sub 1-III-46 (17.21 g, 0.0413 mol) and 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (13.62 g) obtained in the above synthesis , 0.0413 mol), THF (90ml) and H ₂ O (45ml) dissolved in K ₂ CO ₃ (17.12 g, 0.1238 mol), Pd(PPh ₃ ) ₄ (1.91 g, 0.0017 mol) was obtained by using the Sub 1-1 synthesis method to obtain 13.99 g (yield: 58%) of the product.

Meanwhile, the compound belonging to Sub 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS values of the compound belonging to Sub 1.

[Table 1]

2. Sub Synthesis of 2

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 7 below, but is not limited thereto.

<Reaction Scheme 7>

Synthesis examples of specific compounds belonging to Sub 2 are as follows.

(One) Sub 2-1 Synthesis example

<Reaction Scheme 8>

Sub 2-I-1 synthesis

Put the starting material benzonitrile (40 g, 0.3879 mol) in a round bottom flask and dissolve with benzene (1300 ml), potassium t- butoxide (152.34 g, 1.3576 mol), acetonitrile (47.77 g, 1.1637 mmol) was added and stirred at 20 °C. When the reaction was completed, ether and 2% NaHCO ₃ were added. After concentration, the resulting compound was recrystallized to obtain 29.08 g (yield: 52%) of the product.

Sub 2-1 synthesis

After the Sub 2-I-1 (29.08 g, 0.2017 mol) obtained in the above synthesis was added to a round bottom flask, N,N-dimethylbenzamide (33.10 g, 0.2219 mol) and POCl ₃ (380 ml) were added and refluxed. When the reaction was completed, the reactant was added to ice water and ammonium hydroxide (pH=7) was added. After extraction with chloroform and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized to obtain 33.89 g (yield: 63%) of the product.

(2) Sub 2-3 Synthesis example

<Reaction Scheme 9>

Sub 2-I-3 synthesis

Potassium t- butoxide (45.25 g, 0.4033 mmol), acetonitrile in the starting material [1,1'-biphenyl]-4-carbonitrile (20.65 g, 0.1152 mol) (14.19 g, 0.3457 mmol) and benzene (380ml) were used to obtain 11.93 g (yield: 47%) of the product using the Sub 2-I-1 synthesis method.

Sub 2-3 synthesis

N,N-dimethylbenzamide (8.89 g, 0.0596 mol), POCl ₃ (100ml) in Sub 2-I-3 (11.93 g, 0.0542 mol) obtained in the above synthesis was added to the product 10.58 g ( Yield: 57%).

Meanwhile, the compound belonging to Sub 2 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS values of the compound belonging to Sub 2.

[Table 2]

3. Product synthesis

Sub 1 (1 equivalent) is put in a round bottom flask and dissolved in THF, then Sub 2 (1 equivalent), Pd (PPh ₃ ) ₄ (0.04 equivalent), NaOH (3 equivalent), and water are added and stirred at 80°C. I did. When the reaction was completed, CH ₂ Cl ₂ and water were extracted, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain a final product.

(One) Product 1-1 Synthesis example

<Reaction Scheme 10>

Sub 1-1 (10 g, 0.0245 mol) obtained in the above synthesis was put in a round bottom flask and dissolved in THF (120 ml), and then Sub 2-1 (6.53 g, 0.0245 mmol), Pd(PPh ₃ ) ₄ (1.13 g , 0.001 mol), NaOH (2.94 g, 0.0735 mol), H ₂ O (60ml) was added and stirred at 80 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 8.79 g (yield: 70%) of the product.

(2) Product 1-32 Synthesis example

<Reaction Scheme 11>

Sub 1-20 (13 g, 0.0256 mol) obtained in the above synthesis Sub 2-1 (6.82 g, 0.0256 mmol), Pd(PPh ₃ ) ₄ (1.18 g, 0.001 mol), NaOH (3.07 g, 0.0767 mol) , THF (120ml), H ₂ O (60ml) was obtained by using the above Product 1-1 synthesis method to obtain 10.18 g (yield: 65%) of the product.

(3) Product 1-72 Synthesis example

<Reaction Scheme 12>

Sub 1-46 (8 g, 0.0137 mol) obtained in the above synthesis Sub 2-3 (4.69 g, 0.0137 mmol), Pd (PPh ₃ ) ₄ (0.63 g, 0.0005 mol), NaOH (1.64 g, 0.0411 mol) , THF (80ml), H ₂ O (40ml) was used to obtain a product of 6.7 g (yield: 64%) using the Product 1-1 synthesis method.

(4) Product 1-76 Synthesis example

<Reaction Scheme 13>

Sub 2-1 (6.54 g, 0.0245 mmol), Pd(PPh ₃ ) ₄ (1.13 g, 0.001 mol), NaOH (2.94 g, 0.0735 mol) in Sub 1-32 (10.03 g, 0.0245 mol) obtained in the above synthesis , THF (120ml), H ₂ O (60ml) was obtained by using the above Product 1-1 synthesis method to obtain a product 8.94 g (yield: 71%).

Meanwhile, the FD-MS values of compounds 1-1 to 1-84 of the present invention prepared according to the synthesis example as described above are shown in Table 3 below.

[Table 3]

II . Synthesis of Formula 2

Compounds represented by Chemical Formula 2 according to the present invention (final products) are synthesized as shown in Scheme 14 below.

<Reaction Scheme 14>

(Ar ² to Ar ⁴ are the same as defined in Formula 2.)

1. Synthesis of intermediates of formula 2

The synthesis method disclosed in the applicant's Korean Patent Registration No. 10-1251451 (registered on April 5, 2013) and No. 10-1298483 (registered on August 21, 2013) were used.

2. Product synthesis

After dissolving HNAr ³ Ar ⁴ (1 equivalent) in toluene in a round bottom flask, Ar ² -Br (1.2 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P( t -Bu) ₃ (0.08 equivalent), NaO t -Bu (3 eq) was added and stirred at 100 °C. When the reaction was completed, CH ₂ Cl ₂ and water were extracted, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain a final product.

(One) Product 2-5 Synthesis example

<Reaction Scheme 15>

N -([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9 H -fluoren-2-amine (16.32 g, 45.1 mmol) was added to a round bottom flask and dissolved with toluene (500ml). Later, 3-(4-bromophenyl)-9-phenyl-9 H- carbazole (21.58 g, 54.2 mmol), Pd ₂ (dba) ₃ (1.24 g, 1.4 mmol), 50% P( t- Bu) ₃ ( 1.8ml, 3.6 mmol), NaO t -Bu (13.02 g, 135.4 mmol) was added and stirred at 100 °C. When the reaction was completed, the product was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 26.36 g (yield: 86%) of the product.

(2) Product 2-46 Synthesis example

<Reaction Scheme 16>

N ,9,9-triphenyl-9 H -fluoren-2-amine (17.93 g, 43.8 mmol) to 2-(3-bromophenyl)-9-phenyl-9 H -carbazole (20.93 g, 52.5 mmol), Pd ₂ (dba) ₃ (1.2 g, 1.3 mmol), 50% P( t -Bu) ₃ (1.7ml, 3.5 mmol), NaO t -Bu (12.62 g, 131.3 mmol), toluene (480ml) were added to Product 2- 5 Using a synthesis method, the product 23.87 g (yield: 75%) was obtained.

(3) Product 2-49 Synthesis example

<Scheme 17>

N -([1,1'-biphenyl]-4-yl)dibenzo[ b , d ]thiophen-2-amine (17.07 g, 48.6 mmol) in 3-(3-bromophenyl)-9-phenyl-9 H- carbazole (23.21 g, 58.3 mmol), Pd ₂ (dba) ₃ (1.33 g, 1.5 mmol), 50% P( t -Bu) ₃ (1.9ml, 3.9 mmol), NaO t -Bu (14 g, 145.7 mmol) ), toluene (530ml) was obtained by using the Product 2-5 synthesis method to obtain a product 26.31 g (yield: 81%).

(4) Product 2-102 Synthesis example

<Reaction Scheme 18>

N -([1,1'-biphenyl]-4-yl)-9,9'-spirobi[fluoren]-2-amine (21.65 g, 44.8 mmol) in 4-(4-bromophenyl)dibenzo[ b , d ]thiophene (18.23 g, 53.7 mmol), Pd ₂ (dba) ₃ (1.23 g, 1.3 mmol), 50% P( t -Bu) ₃ (1.7ml, 3.6 mmol), NaO t -Bu (12.91 g, 134.3 mmol) mmol), toluene (490ml) was used to obtain a product 25.58 g (yield: 77%) using the synthesis method of Product 2-5.

(5) Product 2-129 Synthesis example

<Reaction Scheme 19>

N -([1,1'-biphenyl]-4-yl)naphthalen-2-amine (14.32 g, 48.5 mmol) to 9-(4'-bromo-[1,1'-biphenyl]-4-yl) -9 H -carbazole (23.17 g, 58.2 mmol), Pd ₂ (dba) ₃ (1.33 g, 1.5 mmol), 50% P( t -Bu) ₃ (1.9ml, 3.9 mmol), NaO t -Bu (13.98 g, 145.4 mmol), and toluene (530ml) were obtained by using the Product 2-5 synthesis method to obtain 24.66 g (yield: 83%) of the product.

(6) Product 2-130 Synthesis example

<Reaction Scheme 20>

N -([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-3-amine (16.83 g, 52.4 mmol) in 9-(4'-bromo-[1,1' -biphenyl]-4-yl)-9 H -carbazole (25.03 g, 62.8 mmol), Pd ₂ (dba) ₃ (1.44 g, 1.6 mmol), 50% P( t -Bu) ₃ (2ml, 4.2 mmol) , NaO t -Bu (15.1 g, 157.1 mmol), toluene (580ml) was obtained by using the above Product 2-5 synthesis method to give a product 26.76 g (yield: 80%).

Meanwhile, FD-MS values of compounds 2-1 to 2-156 of the present invention prepared according to the synthesis example as described above are shown in Table 4 below.

[Table 4]

Manufacturing evaluation of organic electric devices

[ Example I-1] Red organic electroluminescent device ( Electron transport layer )

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as an electron transport layer material. First, vacuum deposition of 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as "2-TNATA") to a thickness of 60 nm on the ITO layer (anode) formed on a glass substrate To form a hole injection layer, vacuum 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as “NPD”) to a thickness of 60 nm on the hole injection layer. By evaporation, a hole transport layer was formed. Next, CBP [4,4'-N,N'-dicarbazole-biphenyl] as a host material on the hole transport layer, bis-(1-phenylisoquinolyl) iridium(III)acetylacetonate as a dopant material (hereinafter "(piq) ₂ Ir(acac)") was doped in a weight ratio of 95:5 to deposit a light emitting layer having a thickness of 30 nm. 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 the compound 1-1 of the present invention was vacuum deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer. Thereafter, LiF, an alkali metal halide, was deposited on the electron transport layer 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 I-2] to [ Example I-74] Red organic electroluminescent device ( Electron transport layer )

An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that the compound of the present invention described in Table 5 was used instead of the compound 1-1 of the present invention as an electron transport layer material.

[ Comparative example I-1]

An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that Comparative Compound 1 below was used instead of Compound 1-1 of the present invention as an electron transport layer material.

<Comparative compound 1> Alq ₃

[ Comparative example I-2]

An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that Comparative Compound 2 below was used instead of Compound 1-1 of the present invention as an electron transport layer material.

<Comparative compound 2>

[ Comparative example I-3]

An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that Comparative Compound 3 below was used instead of Compound 1-1 of the present invention as an electron transport layer material.

<Comparative compound 3>

Electroluminescence by applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples I-1 to I-74 and Comparative Examples 1 to 3 of the present invention with the PR-650 of photoresearch (EL) characteristics were measured, and T95 life was measured through a life measurement equipment manufactured by McScience at a reference luminance of 2500 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 was confirmed that when the material for an organic electroluminescent device of the present invention was used as an electron transport layer, it exhibited higher luminous efficiency and higher lifetime than Comparative Compound 1 to Comparative Compound 3.

These results, the comparative compound 1 in the case of the present invention for Alq ₃ gatneunde low T ₁ than T ₁ value of Ir (ppy) ₃ was used as the dopant in the light emitting layer, whereas compound than T ₁ value of Ir (ppy) ₃ generally It seems to be because it shows a high T ₁ value.

When the compound of the present invention is used as an electron transport layer, it is judged that the efficiency is increased because it has a higher T ₁ value than the dopant, so that the probability that excitons can stay in the emission layer is relatively increased, and the efficiency in the emission layer is increased. Accordingly, it is determined that the driving voltage is lowered and the life of the hole can be reduced due to the high T ₁ value.

In addition, Comparative Compound 2 and Comparative Compound 3 containing quinazoline similar to the compounds of the present invention appear to have lower LUMO values than the compounds of the present invention. This means that the inventive compound can transfer electrons into the light emitting layer more easily and faster than the comparative compounds 2 and 3, and this increases the charge balance in the light emitting layer, resulting in increased efficiency.

In addition, it was confirmed that the compound of the present invention used as the electron transport layer became a more twisted structure when introducing a meta-broken phenyl group to the linking group L ¹ and had a higher T ₁ value.

[ Example II -One] Red organic electroluminescent device ( Electron transport layer , Hole transport layer )

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as an electron transport layer material. First, on the ITO layer (anode) formed on the glass substrate, 2-TNATA was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then the compound 2-5 of the present invention was vacuum deposited on the hole injection layer to a thickness of 60 nm. A hole transport layer was formed. Next, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping CBP as a host material and (piq) ₂ Ir(acac) as a dopant material at a weight ratio of 95:5. Subsequently, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Compound 1-1 of the present invention was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, an alkali metal halide, was deposited on the electron transport layer 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 II -2] to [ Example II -6] Red organic electroluminescent device ( Electron transport layer , Hole transport layer )

An organic electroluminescent device was manufactured in the same manner as in Example II-1, except that the compound of the present invention described in Table 6 was used instead of the compound 1-1 of the present invention as the electron transport layer material.

[ Example II -7] Red organic electroluminescent device ( Electron transport layer , Hole transport layer )

An organic electroluminescent device was manufactured in the same manner as in Example II-1, except that the compound 2-102 of the present invention described in Table 6 was used instead of the compound 2-5 of the present invention as a material for the hole transport layer.

[ Example II -8] to [ Example II -12] Red organic electroluminescent device ( Electron transport layer , Hole transport layer )

An organic electroluminescent device was manufactured in the same manner as in Example II-7, except that the compound of the present invention shown in Table 6 was used instead of the compound 1-1 of the present invention as the electron transport layer material.

[ Example II -13] Red organic electroluminescent device ( Electron transport layer , Hole transport layer )

An organic electroluminescent device was manufactured in the same manner as in Example II-1, except that the compound 2-129 of the present invention described in Table 6 was used instead of the compound 2-5 of the present invention as a material for the hole transport layer.

[ Example II -14] to [ Example II -18] Red organic electroluminescent device ( Electron transport layer , Hole transport layer )

An organic electroluminescent device was manufactured in the same manner as in Example II-13, except that the compound of the present invention described in Table 6 was used instead of the compound 1-1 of the present invention as the electron transport layer material.

By applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples II-1 to II-18 of the present invention, electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and 2500 cd The T95 life was measured using a life measurement equipment manufactured by McScience at the standard luminance of /m ² , and the measurement results are shown in Table 6 below.

[Table 6]

[ Example III -One] Red organic electroluminescent device ( Electron transport layer , Hole transport layer , Light-emitting auxiliary layer )

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention as an electron transport layer material. First, on the ITO layer (anode) formed on the glass substrate, 2-TNATA was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then the compound 2-5 of the present invention was vacuum deposited on the hole injection layer to a thickness of 60 nm. A hole transport layer was formed. Subsequently, after vacuum deposition of the compound 2-46 of the present invention to a thickness of 20 nm on the hole transport layer to form an emission auxiliary layer, CBP as a host material and a dopant material (piq) on the emission auxiliary layer ₂ Ir(acac) was doped at a weight ratio of 95:5 to deposit a light emitting layer having a thickness of 30 nm. Subsequently, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Compound 1-1 of the present invention was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, an alkali metal halide, was deposited on the electron transport layer 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 III -2] to [ Example III -6] Red organic electroluminescent device ( Electron transport layer , Hole transport layer , Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured in the same manner as in Example III-1, except that the compound of the present invention described in Table 7 was used instead of the compound 1-1 of the present invention as the electron transport layer material.

[ Example III -7] Red organic electroluminescent device ( Electron transport layer , Hole transport layer , Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured in the same manner as in Example III-1, except for using the compound 2-49 of the present invention shown in Table 7 below instead of the compound 2-46 of the present invention as the light emitting auxiliary layer material.

[ Example III -8] to [ Example III -12] Red organic electroluminescent device ( Electron transport layer , Hole transport layer , Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured in the same manner as in Example III-7, except that the compound of the present invention described in Table 7 below was used instead of the compound 1-1 of the present invention as the electron transport layer material.

[ Example III -13] Red organic electroluminescent device ( Electron transport layer , Hole transport layer , Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured in the same manner as in Example III-1, except for using the compound 2-130 of the present invention shown in Table 7 below instead of the compound 2-46 of the present invention as the light emitting auxiliary layer material.

[ Example III -14] to [ Example III -18] Red organic electroluminescent device ( Electron transport layer , Hole transport layer , Light-emitting auxiliary layer )

An organic electroluminescent device was manufactured in the same manner as in Example III-13, except that the compound of the present invention described in Table 7 was used instead of the compound 1-1 of the present invention as the electron transport layer material.

By applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples III-1 to III-18 of the present invention, electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and 2500 cd The T95 life was measured through a life measurement equipment manufactured by McScience at the standard luminance of /m ² , and the measurement results are shown in Table 7 below.

[Table 7]

As can be seen from the results of Tables 5 to 7 above, Example III than Example I (Example I-1 to Example I-74) and Example II (Example II-1 to Example II-18) (Example III-1 to Example III-18) The luminous efficiency and lifetime are improved.

In addition, as can be seen in Tables 5 and 6, in the case of Example II in which the compound of Formula 2 was used as the hole transport layer material than when NPB was used as the hole transport layer, lower driving voltage and lower driving voltage than when using NPB Represents a high service life.

In particular, in Tables 5 and 6, the device characteristics of an embodiment in which a material having a high T ₁ value and a wide band gap among the compounds represented by Formula 2 between the hole transport layer and the light emitting layer is additionally applied as a light emitting auxiliary layer in order to further improve the lifespan. The measurement results are shown in Table 7 above.

Referring to Table 7 above, when the material of Formula 2 is used as the hole transport layer and the light emission auxiliary layer, and the compound of Formula 1 or 1a, which is the compound of the present invention, is used for the electron transport layer, it shows a low driving voltage and high luminous efficiency. It can be seen that the lifespan is greatly increased. It is judged that the efficiency increased by increasing the charge balance in the emission layer as the holes transferred from the hole transport layer became somewhat stagnant in the light emitting auxiliary layer having a low HOMO value. In addition, it is considered that the decrease in color purity is reduced by preventing light emission at the hole transport layer interface by reducing electrons passing through the emission layer due to the high T ₁ value of the emission auxiliary layer.

A device having high luminous efficiency and high lifetime by using the compound represented by Formula 1 or 1a of the present invention as an electron transport layer material and the compound represented by Formula 2 as a hole transport layer and/or a light emission auxiliary layer as shown in Table 7 above. The combination will be difficult to infer its performance easily even for those of ordinary skill in the art to which the present invention belongs.

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 interpreted 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 R ¹ are each independently an aryl group or fluorenyl group of C ₆ -C ₂₄ , m is an integer of 0 to 4, and when m is 2 or more, R ¹ is the same or different from each other,
L ¹ is a single bond, a C ₂ -C ₆₀ heterocycle containing at least one hetero atom selected from the group consisting of a C ₆ -C ₆₀ arylene group, a fluorenylene group, O, N, S, Si and P Group, selected from the group consisting of a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ , and combinations thereof, each of which is deuterium, halogen, silane group, siloxane group, boron group , a germanium group, a cyano group, a nitro group, C ₁ -C ₂₀ coming of the alkylthio, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ in the alkyl group, C ₂ -C ₂₀ alkenyl group of, C ₂ -C alkynyl, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, fluorene group, O, N, S, at least one heteroatom selected from the group consisting of Si and P of ₂₀ At least one substituent selected from the group consisting of C ₂ -C ₂₀ heterocyclic group, C ₃ -C ₂₀ cycloalkyl group, C ₇ -C ₂₀ arylalkyl group, and C ₈ -C ₂₀ arylalkenyl group Can be optionally substituted,
R ² and R ³ are independently of each other C ₆ -C ₆₀ of C ₂ -C ₆₀ containing at least one heteroatom selected from the group consisting of aryl group, fluorenyl group, O, N, S, Si and P It is selected from the group consisting of a heterocyclic group, a fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring, and combinations thereof,
The aryl group and fluorenyl group of Ar ¹ are selected from the group consisting of deuterium, C ₁ -C ₂₀ alkyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ aryl group and fluorenyl group substituted with deuterium May be optionally substituted with one or more substituents,
The aryl and fluorenyl groups of R ¹ , R ² and R ³ , the heterocyclic group and the fused ring group of R ² and R ³ , independently of each other, are deuterium, halogen, silane group, siloxane group, boron group, germanium group, a cyano group, a nitro group, an alkylthio import of C ₁ -C _20, alkynyl of C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂₀ of the , C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, fluorene group, O, N, S, C, comprising at least one heteroatom selected from the group consisting of Si and P _To be optionally substituted with one or more substituents selected from the group consisting of ₂ -C ₂₀ heterocyclic group, C ₃ -C ₂₀ cycloalkyl group, C ₇ -C ₂₀ arylalkyl group, and C ₈ -C ₂₀ arylalkenyl group I can. The method of claim 1,
Formula 1 is a compound characterized in that represented by the following formula 1a:
<Formula 1a>

In Formula 1a,
Ar ¹ , R ¹ , L ¹ and m are the same as defined in claim 1,
R ¹² and R ¹³ are each independently i) containing at least one heteroatom selected from the group consisting of deuterium, halogen, C ₆ -C ₂₀ aryl, fluorenyl group, O, N, S, Si and P C ₂ -C ₂₀ heterocyclic group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group and C ₁ -C ₂₀ selected from the group consisting of an alkoxy group, or Or ii) adjacent groups may be bonded to each other to form at least one ring, wherein R ¹² and R ¹³ not forming a ring are the same as defined in i) above, and n and o are independently 0 Is an integer of 5, when n is an integer of 2 or more, R ¹² is the same as or different from each other, and when o is an integer of 2 or more, R ¹³ is the same or different from each other,
The aryl group, fluorenyl group, heterocyclic group, alkyl group, alkenyl group, and alkoxy group of R ¹² and R ¹³ are each independently deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, Import alkylthio of C ₁ -C _20, alkynyl, C ₆ -C ₂₀ of a C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂₀ of the C ₂ -C ₂₀ hetero containing at least one heteroatom selected from the group consisting of an aryl group of, C ₆ -C ₂₀ aryl group substituted with deuterium, fluorenyl group, O, N, S, Si and P It may be optionally substituted with one or more substituents selected from the group consisting of a cyclic group, a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ arylalkyl group, and a C ₈ -C ₂₀ arylalkenyl group. The method of claim 1,
The compound represented by Formula 1 is a compound characterized in that one of the following compounds:

. A first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode,
An organic electric device, wherein the organic material layer contains the compound of claim 1. The method of claim 4,
The compound is an organic electric device, characterized in that contained in at least one of the electron transport layer and the light emitting layer of the organic material layer. The method of claim 4,
The organic material layer includes an electron transport layer, an emission layer, an emission auxiliary layer, and a hole transport layer, and the emission auxiliary layer is formed between the hole transport layer and the emission layer,
The electron transport layer contains the compound represented by Formula 1,
At least one layer of the hole transport layer and the light-emitting auxiliary layer independently of each other comprises a compound represented by the following formula (2):
<Formula 2>

In Chemical Formula 2,
Ar ² and Ar ³ are independently of each other C ₂ -C ₆₀ containing at least one heteroatom selected from the group consisting of C ₆ -C ₆₀ aryl group, fluorenyl group, O, N, S, Si and P Heterocyclic group, fused ring group of C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkyne It is selected from the group consisting of diary, a C ₁ -C ₃₀ alkoxy group, and a C ₆ -C ₃₀ aryloxy group,
Ar ⁴ is the following formula 2a or 2b,
<Formula 2a><Formula2b>

In Formulas 2a and 2b,
X is NR ^d , O, S, or CR ^e R ^f , wherein R ^d to R ^f are independently of each other C ₆ -C ₆₀ aryl group, fluorenyl group, O, N, S, Si and P C ₂ -C ₆₀ heterocyclic group including at least one heteroatom selected from the group, a fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring, a C ₁ -C ₅₀ alkyl group , C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₃₀ alkoxy group, and C ₆ -C ₃₀ selected from the group consisting of aryloxy group, R ^e and R ^f Combine with each other to form a compound with a spy,
L ² and L ³ are a single bond, C ₆ -C ₆₀ arylene group, fluorenylene group, C ₂ -C ₆₀ containing at least one hetero atom selected from the group consisting of O, N, S, Si and P It is selected from the group consisting of a heterocyclic group of, a fused ring group of an aliphatic ring of C ₃ -C ₆₀ and an aromatic ring of C ₆ -C ₆₀ , and combinations thereof, except for the case where L ³ is a single bond,
L ² and L ³ are independently of each other deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, C ₁ -C ₂₀ alkylthio group, C ₁ -C ₂₀ alkoxy group, an aryl group of C ₁ -C ₂₀ alkyl, C ₂ -C ₂₀ alkenyl, C ₂ -C ₂₀ alkynyl, C ₆ -C ₂₀ substituted with a C ₆ aryl group, a heavy hydrogen of -C ₂₀ of the, fluorene Diary, a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C ₃ -C ₂₀ cycloalkyl group, a C ₇ -C ₂₀ aryl It may be optionally substituted with one or more substituents selected from the group consisting of an alkyl group and a C ₈ -C ₂₀ arylalkenyl group,
R ⁴ to R ⁷ are i) at least one heteroatom independently selected from the group consisting of deuterium, tritium, halogen, C ₆ -C ₆₀ aryl group, fluorenyl group, O, N, S, Si and P C ₂ -C ₆₀ heterocyclic group, C ₃ -C ₆₀ aliphatic ring and C ₆ -C ₆₀ aromatic ring fused ring group, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ alkene Diary, selected from the group consisting of an alkynyl group of C ₂ -C ₂₀ , an alkoxy group of C ₁ -C ₃₀ , and an aryloxy group of C ₆ -C ₃₀ , or ii) adjacent groups are bonded to each other to at least one ring To form, wherein the group that does not form a ring is the same as defined in i) above,
p, r and s are each an integer of 0 to 4, q is an integer of 0 to 3, and when each of them is an integer of 2 or more, each of R ⁴ to R ⁷ is the same as or different from each other,
When Ar ² , Ar ³ , R ⁴ to R ⁷ are each an aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group or aryloxy group, each of them is independently alkyl group of deuterium, a halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, C ₁ -C ₂₀ coming of the alkylthio, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ a, C of ₂ -C ₂₀ alkenyl, C ₂ -C ₂₀ alkynyl, C ₆ -C ₂₀ substituted with a C ₆ aryl group, a heavy hydrogen of -C ₂₀ aryl group, fluorenyl group, O, N, S, Si And C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of P, C ₃ -C ₂₀ cycloalkyl group, C ₇ -C ₂₀ arylalkyl group, and C ₈ -C ₂₀ It may be substituted with one or more substituents selected from the group consisting of arylalkenyl groups. The method of claim 6,
An organic electric device, characterized in that the compound represented by Formula 2 is one of the following compounds:

The method of claim 4,
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 4; And
Electronic device including; a control unit for controlling 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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