KR102381320B1 - Compound for organic electric element, organic electric element comprising the same and electronic device thereof - Google Patents

Abstract

Disclosed are an organic electric device comprising a compound represented by Chemical Formula 1, a first electrode, a second electrode, and an organic material layer between the first and second electrodes, and an electronic device including the same, wherein the organic material layer is a compound represented by Chemical Formula 1 By including this, it is possible to lower the driving voltage of the organic electric device, it is possible to improve the luminous efficiency and lifespan.

Description

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

A material used as an organic layer in an organic electric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.

Currently, the portable display market is a large-area display, and the size thereof is increasing, and thus, more power consumption than the power consumption required by the existing portable display is required. Therefore, power consumption has become an important factor for a portable display having a limited power supply such as a battery, and efficiency and lifespan problems are also important factors that must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan. However, the efficiency cannot be maximized by simply improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.

In addition, in order to solve the light emitting problem and the driving voltage problem in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer (multilayer hole transport layer) should exist between the hole transport layer and the light emitting layer, and different It is time to develop a light emitting auxiliary layer.

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 recombination of electrons and holes occurs in the light emitting layer to form excitons.

However, most materials used for the hole transport layer have a low T1 value because they have to have a low HOMO value. As a result, excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge unbalance in the emission layer. This results in light emission at the hole transport layer interface.

When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are lowered and the lifespan is shortened. Therefore, it should be a material having a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, have a high T1 value, and have hole mobility within an appropriate driving voltage range (within the blue device driving voltage range of a full device) The development of a light emitting auxiliary layer material having hole mobility is urgently required.

However, this cannot be achieved simply with the structural characteristics of the core of the light-emitting auxiliary layer material, and when the characteristics of the core and sub-substituent of the light-emitting auxiliary layer material and the appropriate combination between the light-emitting auxiliary layer and the hole transport layer, and the light-emitting auxiliary layer and the light-emitting layer are achieved A device with high efficiency and long life can be realized.

In order to fully exhibit the excellent characteristics of an organic electric device, materials constituting the organic layer in the device, for example, hole injection material, hole transport material, light emitting material, electron transport material, electron injection material, light emitting auxiliary layer material, etc. are stable and efficient materials. It should be supported by this, and in particular, the development of the material of the light emitting auxiliary layer is urgently required.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency, color purity and lifespan of the 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 an embodiment of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency, color purity, and lifespan of the device can be improved.

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

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

As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise specified.

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

As used herein, the term “haloalkyl group” or “halogenalkyl group” refers to an alkyl group substituted with halogen unless otherwise specified.

The term "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise specified, has a double or triple bond of 2 to 60 carbon atoms, respectively, and includes a straight or branched chain group, and is limited thereto it is not

As used herein, the term “cycloalkyl” refers to an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has 1 to 60 carbon atoms unless otherwise specified, and is limited thereto. it is not

As used herein, the term “aryloxyl group” or “aryloxy group” refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structures, respectively, unless otherwise specified, " A 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 to It includes the case of forming a compound as a spy together.

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto. In the present invention, the aryl group or the arylene group includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.

The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like.

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

As used herein, the term "ring" includes monocyclic and polycyclic rings, and includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.

As used herein, the term "polycyclic" includes ring assemblies such as biphenyl, terphenyl, etc., fused multiple ring systems and spiro compounds, and includes aromatic as well as non-aromatic, hydrocarbon Rings include, of course, heterocycles containing at least one heteroatom.

As used herein, the term "ring assemblies" refers to two or more ring systems (single or fused ring systems) directly connected to each other through a single bond or a double bond, and a direct connection between such rings It means that the number of linkages is one less than the total number of ring systems in the compound. In a ring aggregate, the same or different ring systems may be directly linked to each other through single or double bonds.

As used herein, the term "fused multiple ring system" refers to a fused ring form shared by at least two atoms, and includes a fused ring system of two or more hydrocarbons and at least one heteroatom. and a form in which at least one heterocyclic system is fused. The fused multiple ring system 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 means a connection formed by sharing only one atom in two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

Also, when prefixes are named consecutively, it is meant that the substituents are listed in the order listed first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group, and an arylcarbonylalkenyl group 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 otherwise explicitly stated, in the term "substituted or unsubstituted" as used herein, "substitution" 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 group, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₈ -C ₂₀ arylalkenyl group, silane group, boron group, germanium group, and O, N, S, Si and P containing at least one heteroatom selected from the group consisting of C ₂ -C ₂₀ heterocyclic group means substituted with one or more substituents selected from the group consisting of and is not limited to these substituents.

In the present specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'. Similarly, in the case of pyrimidine, regardless of the valence, it can be described as 'pyrimidine' or as the 'name of the group' of the valence, such as a pyrimidinyl group in the case of monovalent or pyrimidinylene in the case of divalent. there is.

In addition, unless there is an explicit explanation, the formula used in the present invention applies the same as the definition of the substituent by the exponential definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring. It can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R ¹ is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same as or different from each other.

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

In adding reference numerals to the components of each drawing, it should be noted that the same components are given the same reference numerals as much as possible even though 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 gist of the present invention, the detailed description thereof will be omitted.

In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the elements from other elements, and the essence, order, or order of the elements are not limited by the terms. When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is between each component. It should be understood that elements may also be “connected,” “coupled,” or “connected.”

Further, when a component, such as a layer, membrane, region, plate, etc., is said to be “on” or “on” another component, this means not only when it is “directly above” another component, but also when another component is in between. It should be understood that cases may be included. Conversely, when it is said that an element is "on top of" another part, it should be understood to mean that there is no other part in the middle.

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

Referring to FIG. 1 , an organic electric device 100 according to an embodiment of the present invention includes a first electrode 120 , a second electrode 180 , and a first electrode 120 formed on a substrate 110 , and the second electrode 120 . An organic material layer including the compound according to the present invention is provided between the two electrodes 180 . 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 sequentially include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , and an electron injection layer 170 on the first electrode 120 . At this time, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc., and the electron transport layer 160, etc. It may also serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to an embodiment of the present invention further includes a protective layer or a light efficiency improving layer (Capping layer) formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer. can do.

The compound according to an embodiment of the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170) and the like, a host or dopant material of the light emitting layer 150, or a material of the light efficiency improving layer. For example, the compound of the present invention may be used as a material for the hole transport layer 140 and/or the light emission auxiliary layer 151 , preferably as a material for the light emission auxiliary layer 151 .

On the other hand, even with the same core, the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, so the selection of the core and the combination of sub-substituents bonded thereto Research is required, and in particular, when the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.

Therefore, in the present invention, by forming the light emission auxiliary layer 151 using the compound represented by Chemical Formula 1, the energy level and T ₁ value between each organic material layer, the intrinsic properties of the material (mobility, interfacial properties, etc.) It is possible to improve the lifetime and efficiency of the electric device at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 120, and the hole injection layer 130 thereon. , after forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon. there is. In addition, an auxiliary light emitting layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150 , and an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160 .

In addition, the organic layer is a solution process or a solvent process rather than a deposition method 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, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

The organic electric device according to an embodiment of the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on a material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and excellent in processability, and can be manufactured using the existing color filter technology of LCD. Various structures for a white organic light emitting diode mainly used as a backlight device have been proposed and patented. Typically, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting units are mutually planar, and a stacking method in which R, G, and B light emitting layers are stacked up and down There is a color conversion material (CCM) method using electroluminescence by the blue (B) organic light emitting layer and photo-luminescence of an inorganic phosphor using the light therefrom. could also be applied to such WOLEDs.

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

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. In this case, the electronic device may be a current or future wired/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 control, a navigation system, a game machine, various TVs, and various computers.

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

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

<Formula 1>

In Formula 1, each symbol may be defined as follows.

X ¹ and X ² are each independently O or S.

R ³ to R ⁵ are each independently i) hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ); or ii) adjacent groups may be bonded to each other to form a ring. A ring formed by bonding neighboring R ³ , neighboring R ⁴ , or neighboring R ⁵ to each other is at least one of C ₆ ~ C ₆₀ aromatic hydrocarbon, fluorene, O, N, S, Si, and P It may be a C ₂ ~ C ₆₀ heterocyclic group containing a hetero atom, a C ₃ ~ C ₆₀ aliphatic ring, or a fused ring group of a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring.

When R ³ to R ⁵ are an aryl group, preferably a C ₆ to C ₃₀ aryl group or a C ₆ to C ₂₀ aryl group, more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, naphthyl , biphenyl, terphenyl, and the like.

When neighboring R ³ , neighboring R ⁴ , or neighboring R ⁵ are bonded to each other to form an aromatic hydrocarbon ring, preferably C ₆ to C ₃₀ aromatic hydrocarbon or C ₆ to C ₂₀ aromatic hydrocarbon; More preferably, C ₆ ~ C ₁₄ aromatic hydrocarbons, such as benzene, naphthalene, phenanthrene, and the like may be formed.

c and e are integers from 0 to 3, respectively, and d is an integer from 0 to 2. When c is an integer of 2 or more, a plurality of R ² are the same as or different from each other, when d is 2, a plurality of R ³ are the same or different from each other, and when e is an integer of 2 or more, a plurality of R ⁴ are each the same or different

Ar ¹ and Ar ² are each independently represented by Formula 2 or Formula 3, and preferably, Ar ¹ and Ar ² are different from each other.

<Formula 2> <Formula 3>

In Chemical Formulas 2 and 3, each symbol may be defined as follows.

Ar ³ To Ar ⁵ Are each independently a C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; -L'-N(R _a )(R _b ); and -L′-S(R _a );

When Ar ³ to Ar ⁵ is an aryl group, preferably a C ₆ -C ₃₀ aryl group or a C ₆ -C ₂₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, such as phenyl, biphenyl , triphenylene, naphthyl, terphenyl, phenanthrene, and the like. When Ar ³ To Ar ⁵ is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group or a C ₂ ~ C ₂₀ heterocyclic group, more preferably a C ₂ ~ C ₁₈ heterocyclic group, such as pyridine , pyrimidine, triazine, dibenzothiophene, dibenzofuran, benzonaphthothiophene, carbazole, phenylcarbazole, dibenzothiophene, benzothienodibenzothiophene, benzocarbazole, quinoline, dimethyl It may be dibenzosilol, benzofurodibenzothiophene, or the like. When Ar ³ to Ar ⁵ is a fluorenyl group, it may be, for example, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, 9,9-dimethyl-9H-fluorene, or the like. .

L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; and a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group; is selected from the group consisting of.

When L ¹ and L ² are an aryl group, preferably a C ₆ -C ₃₀ arylene group or a C ₆ -C ₂₀ arylene group, more preferably a C ₆ -C ₁₂ arylene group, such as phenylene, biphenyl , naphthalene, and the like.

R ¹ and R ² are independently of each other i) hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L'-N(R _a )(R _b ); or ii) adjacent groups are bonded to each other to C ₆ to C ₆₀ aromatic hydrocarbons, fluorene, O, N, S, Si And a C ₂ ~ C ₆₀ heterocyclic group comprising at least one heteroatom of P, a C ₃ ~ C ₆₀ aliphatic ring, or a C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ fusion of an aromatic ring may form a cyclic group, each a is an integer of 0 to 3, b is an integer of 0 to 4, and when a and b are each an integer of 2 or more, each of a plurality of R ¹ or a plurality of R ² is the same as each other, or different

When R ¹ and R ² are an aryl group, preferably a C ₆ -C ₃₀ aryl group or a C ₆ -C ₂₀ aryl group, more preferably a C ₆ -C ₁₂ aryl group, such as phenyl, naphthyl, biphenyl and the like.

When adjacent R ¹ or adjacent R ² are bonded to each other to form a ring, preferably C ₆ ~ C ₃₀ aromatic hydrocarbon or C ₆ ~ C ₂₀ aromatic hydrocarbon, more preferably C ₆ ~ C ₁₄ of aromatic hydrocarbons such as benzene, naphthalene, phenanthrene, and the like.

The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; It is selected from the group consisting of a fused ring group of C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring.

When L' is an arylene group, preferably a C ₆ ~ C ₃₀ arylene group or a C ₆ ~ C ₂₀ arylene group, more preferably a C ₆ ~ C ₁₂ arylene group, such as phenylene, biphenyl, naphthalene etc. When L' is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group or a C ₂ ~ C ₂₀ heterocyclic group, more preferably a C ₂ ~ C ₁₂ heterocyclic group, such as pyridine, pyrimidine , triazine, quinoline, quinazoline, dibenzothiophene, dibenzofuran, and the like.

The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; It is selected from the group consisting of a fused ring group of C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring.

When R _a and R _b are aryl groups, preferably a C ₆ -C ₃₀ aryl group or a C ₆ -C ₂₀ aryl group, more preferably a C ₆ -C ₁₂ aryl group, such as phenyl, naphthyl, biphenyl and the like.

The R ¹ to R ⁵ , R _a , R _b , Ar ³ to Ar ⁵ , L ¹ , L ² , L′, and the adjacent R ¹ to the adjacent R ⁵ rings formed by bonding to each other are deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; a phosphine oxide group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl 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; a C ₆ -C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C ₂₀ An aryl alkenyl group; may be further substituted with one or more substituents selected from the group consisting of.

For example, the R ¹ to R ⁵ , R _a , R _b , Ar ³ to Ar ⁵ , L ¹ , L ² , L′, or a ring formed by bonding adjacent R ¹ to adjacent R ⁵ , etc. is aryl When substituted with a group, it may be further substituted with a preferably C ₆ -C ₂₀ aryl group, more preferably a C ₆ -C ₁₂ aryl group, such as phenyl, naphthyl, biphenyl, and the like, and is substituted with a heterocycle. Preferably, a C ₂ -C ₂₀ heterocyclic group, more preferably a C ₂ -C ₁₂ heterocyclic group, such as pyridine, pyrimidine, triazine, quinazoline, dibenzothiophene, etc. may be further substituted. can In addition, R ¹ to R ⁵ , R _a , R _b , Ar ³ to Ar ⁵ , L ¹ , L ² , L′, or a ring formed by bonding between neighboring R ¹ and neighboring R ⁵ is deuterium; It may be further substituted with a silane group substituted with methyl, ethyl, ethene, propene, F, or phenyl.

Formula 1 may be represented by Formula 4 or Formula 5 below.

<Formula 4> <Formula 5>

In Formulas 4 and 5, X ¹ , X ² , R ¹ to R ⁵ , Ar ³ to Ar ⁵ , L ¹ , L ² , a, b, c, d and e are the same as defined in Formula 1.

Specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.

.

.

In another aspect of the present invention, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode. In this case, the organic material layer contains the compound of the present invention represented by the formula (1).

The compound is included in at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer of the organic material layer, the compound is a single compound or a mixture of two or more included as

In another aspect of the present invention, the present invention provides an electronic device including a display device including the organic electric element, and a control unit for driving the display apparatus, wherein the organic electric element is represented by Formula 1 compounds of the invention.

Hereinafter, examples of the synthesis of the compound represented by Formula 1 and the preparation of an organic electric device according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

Synthesis example

The compound represented by Formula 1 according to the present invention (final products) may be synthesized by reacting Sub 1-a or Sub 1-b with Sub 2 as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

I. Sub 1-a and Sub 1-b Synthesis example

Sub 1-a and Sub 1-b of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but are not limited thereto.

<Scheme 2>

1. Sub 1-1 Synthesis example

In (9-Phenyl-9H-carbazol-2-yl)boronic acid (50 g, 174.13 mmol), sub1-I-1 (70 g, 174.13 mmol), Pd ₂ (PPh ₃ ) ₄ (6.03 g, 5.22 mmol) ), NaOH (20.9 g, 522.41 mmol), THF (580 mL) and water (120 mL) were added and reacted for 6 hours. Upon completion of the reaction, extraction was performed with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 87 g of the product Sub1-1. (Yield: 88%)

2. Sub 1-5 Synthesis example

(9-([1,1'-Biphenyl]-3-yl)-9H-carbazol-2-yl)boronic acid (70 g, 192.7 mmol), sub1-I-5 (77.8 g, 192.7 mmol), (Pd ₂ (PPh ₃ ) ₄ (6.68 g, 5.78 mmol), NaOH (23.1 g, 211.1 mmol), THF (385 mL) and water (120 mL) were added, and the product Sub 1- 5 was obtained in 100 g (yield: 80.8%).

3. Sub 1-13 Synthesis example

To (9-(Phenyl-d5)-9H-carbazol-2-yl)boronic acid (50 g, 171.1 mmol), sub1-I-13 (69 g, 171.1 mmol), (Pd ₂ (PPh ₃ ) ₄ ( 6.0 g, 5.13 mmol), NaOH (20.5 g, 513.6 mmol), THF (450 mL), and water (150 mL) were added, and 80 g of the product Sub1-13 was obtained by using the Sub1-1 synthesis method above (Yield: 81.8%). )

4. Sub 1-23 Synthesis example

In (9-(Pyridin-2-yl)-9H-carbazol-2-yl)boronic acid (40 g, 137.3 mmol), sun1-I-23 (64.4 g, 137.3 mmol), (Pd ₂ (PPh ₃ ) ₄ (4.75 g, 4.11 mmol), NaOH (16.5 g, 411.86 mmol), THF (300 mL), and water (100 mL) were added, and 79 g of the product Sub1-23 was obtained by using the Sub1-1 synthesis method above (yield). : 90.7%)

5. Sub 1- 40 Synthesis Example

In (6,9-Diphenyl-9H-carbazol-2-yl)boronic acid (20 g, 55.1 mmol), sub1-I-40 (20.4 g, 55.1 mmol), (Pd ₂ (PPh ₃ ) ₄ (1.9 g , 1.65 mmol), NaOH (6.6 g, 165.5 mmol), THF (120 mL), and water (40 mL) were added, and 20 g of the product Sub1-40 was obtained by using the Sub1-1 synthesis method (Yield: 59.5%).

On the other hand, the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto, and Table 1 shows the FD-MS values of the compound belonging to Sub 1.

[Table 1]

II. Synthesis of Sub 2

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

<Scheme 3>

1. Sub 2-1 Synthesis example

Bromobenzene (40.68 g, 259.09 mmol) was placed in a round-bottom flask and dissolved in toluene (1360ml), aniline (26.54 g, 285.00 mmol), Pd ₂ (dba) ₃ (7.12 g, 7.77 mmol), 50% P ( t ) -Bu) ₃ (10.1 ml, 20.73 mmol), and NaO t -Bu (74.70 g, 777.28 mmol) were added and stirred at 80°C. Upon completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 32.88 g (yield: 75%) of the product Sub2-1.

2. Sub 2-2 Synthesis example

4-bromo-1,1'-biphenyl (23.65 g, 101.46 mmol) in aniline (10.39 g, 111.60 mmol), Pd ₂ (dba) ₃ (2.79 g, 3.04 mmol), 50% P( t -Bu) ₃ (4.0ml, 8.12 mmol), NaO t -Bu (29.25 g, 304.38 mmol), and toluene (710ml) were added, and 20.66 g (yield: 83%) of the product Sub2-2 using the Sub 2-1 synthesis method. ) was obtained.

3. Sub 2-9 Synthesis example

2-bromodibenzo[b,d]thiophene (38.11 g, 144.82 mmol) in aniline (14.84 g, 159.30 mmol), Pd ₂ (dba) ₃ (3.98 g, 4.34 mmol), 50% P( t -Bu) ₃ ( 5.6ml, 11.59 mmol), NaO t -Bu (41.76 g, 434.47 mmol), and toluene (760ml) were added, and 30.7 g (yield: 77%) of the product Sub2-9 was obtained by using the Sub 2-1 synthesis method. .

4. Sub 2-12 Synthesis example

(One) Sub2 -I-12 synthesis

Diphenylamine (50 g, 295.46 mmol) was placed in a round bottom flask and dissolved in toluene (985ml), 1-bromo-4-chlorobenzene (68 g, 354.54 mmol), Pd ₂ (dba) ₃ (8.12 g, 8.86 mmol) , 50% P( t -Bu) ₃ (7.1 ml, 17.72 mmol), NaO t -Bu (85.3 g, 886.36 mmol) were added and stirred at 80°C. Upon completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 75 g (yield: 90.7%) of the product Sub2-I-12.

(2) Sub2 -12 synthesis

In Sub-I-1 (75 g, 268.08 mmol), aniline (37.5 g, 402.11 mmol), Pd ₂ (dba) ₃ (7.4 g, 8.04 mmol), 50% P( t -Bu) ₃ (6.5 ml, 16.08 mmol) and NaO t -Bu (77.35 g, 804.23 mmol) were added, and after stirring at 130° C., 77.6 g (yield: 77.6%) of the product Sub2-12 was obtained using the Sub2-1 synthesis method.

5. Sub 2-16 Synthesis example

2-bromo-9-phenyl-9H-carbazole (14.71 g, 45.65 mmol) in aniline (4.68 g, 50.22 mmol), Pd ₂ (dba) ₃ (1.25 g, 1.37 mmol), 50% P( t -Bu) ₃ (1.8ml, 3.65 mmol), NaO t -Bu (13.16 g, 136.96 mmol), and toluene (320ml) were added, and 10.99 g (yield: 72%) of the product Sub2-16 using the above Sub2-1 synthesis method. got it

6. Sub 2-17 Synthesis example

2-(4-bromophenyl)pyridine (10.53 g, 44.98 mmol) in aniline (4.61 g, 49.48 mmol), Pd ₂ (dba) ₃ (1.24 g, 1.35 mmol), 50% P( t -Bu) ₃ (1.8 ml, 3.60 mmol), NaO t -Bu (12.97 g, 134.95 mmol), and toluene (315 ml) were added, and 7.87 g (yield: 71%) of the product Sb2-17 was obtained by using the Sub2-1 synthesis method.

7. Sub 2-32 Synthesis example

4-bromo-1,1'-biphenyl-2',3',4',5',6'-d5 (10 g, 42 mmol) in aniline (8.05 g, 86.48 mmol), Pd ₂ (dba) ₃ (2.16 g, 2.36 mmol), 50% P( t -Bu) ₃ (3.1ml, 6.29 mmol), NaO t -Bu (22.67 g, 235.87 mmol), and toluene (550ml) were added, and the above method for synthesizing Sub2-1 was used to obtain 8.1 g (yield: 77%) of the product Sub2-32.

8. Sub 2-52 Synthesis example

(One) Sub2 -I-52 synthesis

In N-phenyl-[1,2'-biphenyl]-3-amine (100 g, 407.6 mmol), 1-bromo-3-chlorobenzene (93.6 g, 489.14 mmol), Pd ₂ (dba) ₃ (14.1 g, 12.23 mmol), 50% P( t -Bu) ₃ (10 ml, 24.46 mmol), NaO t -Bu (117.6 g, 1222.8 mmol), and toluene (1300 ml) were added, and after stirring at 80° C., the 113 g (yield: 79.9%) of the product Sub2-I-52 was obtained by using the Sub2-I-12 synthesis method.

(2) Sub2 -52 synthesis

Sub-I-10 (100 g, 281 mmol), in aniline (31.4 g, 337.2 mmol), Pd ₂ (dba) ₃ (9.74 g, 8.43 mmol), 50% P( t -Bu) ₃ (6.8 ml, 16.86 mmol), NaO t -Bu (81 g, 843 mmol) were added, and the mixture was stirred at 130° C., and then 92 g (yield: 79.4%) of the product Sub2-52 was obtained by using the Sub2-1 synthesis method.

On the other hand, the compound belonging to Sub 2 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS values of the compound belonging to Sub 2 .

[Table 2]

Ⅲ. Product synthesis

1. P-1 Synthesis example

Sub1-1 (20 g, 35.3 mmol) was placed in a round-bottom flask and dissolved with toluene (80ml), followed by Sub2-1 (6.0 g, 35.3 mmol), Pd ₂ (dba) ₃ (1.0 g, 0.1 mmol), 50 % P( t -Bu) ₃ (0.85ml, 0.2 mmol), NaO t -Bu (10 g, 106.3 mmol) was added and stirred at 120°C. After the reaction was completed, the organic layer was dried over MgSO ₄ and concentrated after extraction with toluene and water. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 20 g of product P-1 (yield: 81%).

2. P-12 Synthesis example

Sub1-5 (25 g, 38.9 mmol) was placed in a round-bottom flask and dissolved in toluene (80ml), followed by Sub2-11 (13 g, 38.9 mmol), Pd ₂ (dba) ₃ (1.1 g, 0.11 mmol), 50 % P( t -Bu) ₃ (0.9ml, 0.23 mmol), NaO t -Bu (11.2 g, 116.8 mmol) was added and stirred at 120°C. Then, 35 g (yield: 95.5%) of the product P-12 was obtained by using the separation method of P-1.

3. P-14 Synthesis example

Sub1-1 (20 g, 35.3 mmol) was placed in a round-bottom flask and dissolved in toluene (80ml), followed by Sub2-13 (14.5 g, 35.3 mmol), Pd ₂ (dba) ₃ (1.0 g, 0.1 mmol), 50 % P( t -Bu) ₃ (0.85ml, 0.2 mmol), NaO t -Bu (10 g, 106.3 mmol) was added and stirred at 120°C. Then, 30 g (yield: 90%) of the product P-14 was obtained by using the separation method of P-1.

4. P-33 Synthesis example

Sub1-16 (30 g, 48.7 mmol) was placed in a round-bottom flask and dissolved in toluene (100ml), then Sub2-22 (15.8 g, 48.7 mmol), Pd ₂ (dba) ₃ (1.4 g, 0.15 mmol), 50 % P( t -Bu) ₃ (1.1 ml, 0.3 mmol), NaO t -Bu (14 g, 146.1 mmol) was added and stirred at 120°C. Then, 35 g (yield: 79.4%) of the product P-33 was obtained by using the separation method of P-1.

5. P-45 Synthesis example

Sub1-22 (10 g, 18.1 mmol) was put in a round-bottom flask and dissolved with toluene (40ml), Sub2-32 (4.5 g, 18.1 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.05 mmol), 50 % P( t -Bu) ₃ (0.4ml, 0.1 mmol), NaO t -Bu (5.2 g, 54.5 mmol) was added and stirred at 120°C. Then, 10 g (yield: 72.1%) of the product P-45 was obtained by using the separation method of P-1.

6. P-73 Synthesis example

Sub1-35 (10 g, 18.7 mmol) was placed in a round-bottom flask and dissolved with toluene (40ml), Sub2-2 (4.6 g, 18.7 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.05 mmol), 50 % P( t -Bu) ₃ (0.4ml, 0.1 mmol), NaO t -Bu (5.4 g, 56.8 mmol) was added and stirred at 120°C. Then, 11 g (yield: 79.1%) of the product P-73 was obtained by using the separation method of P-1.

Meanwhile, the FD-MS values of the compounds P-1 to P-76 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Manufacturing and evaluation of organic electric devices

[ Example One] Red organic electroluminescent device ( light emitting layer )

N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene on the ITO layer (anode) formed on the glass substrate After vacuum deposition of -1,4-diamine (hereinafter, 2-TNATA) to a thickness of 60 nm to form a hole injection layer, 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.

Next, after vacuum deposition of the compound P-1 of the present invention to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer, 4,4'-N,N'- as a host material on the light emission auxiliary layer 95:5 weight ratio of dicarbazole-biphenyl (hereinafter abbreviated as “CBP”) and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as “(piq) ₂ Ir(acac)”) as a dopant material was used to form a light emitting layer with a thickness of 30 nm.

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") on the light emitting layer was vacuum deposited to a thickness of 10 nm to form a hole blocking layer. and tris(8-quinolinol)aluminum (hereinafter abbreviated as "Alq ₃ ") was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.

Next, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[ Example 2] to [ Example 21]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 was used instead of the compound P-1 of the present invention as a light emitting auxiliary layer material.

[ comparative example One]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light-emitting auxiliary layer was not formed.

[ comparative example 2] to [ comparative example 4]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the following Comparative Compounds A to C were used instead of Compound P-1 of the present invention as a light emitting auxiliary layer material.

<Comparative compound A> <Comparative compound B> <Comparative compound C>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 21 and Comparative Examples 1 to 4, electroluminescence (EL) characteristics and The T95 lifespan was measured using a lifespan measuring device of McScience at 2500cd/m ² standard luminance, and the measurement results are shown in Table 4 below.

[Table 4]

From Table 4, when the compound of the present invention is used as a material of the light-emitting auxiliary layer, compared to Comparative Examples 1 to 4 in which the light-emitting auxiliary layer is not formed or Comparative Compounds A to C are used as the light-emitting auxiliary layer material, It can be seen that the driving voltage of the organic light emitting diode can be lowered, and the luminous efficiency and lifespan can be significantly improved.

Comparing Comparative Examples 1 to 4, the device characteristics of the organic electroluminescent device were improved when the light emitting layer was formed with the comparative compound compared to the organic electroluminescent device in which the light emitting layer was not formed.

Comparative Compounds A to C used in Comparative Examples 2 to 4 have a skeleton similar to that of the present invention. However, in Comparative Compound A, the same amine derivative is bonded to the outer benzene ring of the 5-ring heterocycle, and Comparative Compound B is the compound of the present invention in that each carbazole derivative is bonded to the outer benzene ring of the heterocyclic ring. There is a difference. In addition, Comparative Compound C is the same as the compound of the present invention in that an amine derivative and a carbazole derivative are bonded to the outer benzene ring of the 5-ring heterocycle, respectively, but the compound of the present invention has a 2-carbazole derivative bonded thereto. On the other hand, Comparative Compound C is different in that a 3-carbazole derivative is bound.

Therefore, due to the difference in the structure of these compounds, the characteristics of the organic electroluminescent device are different when these compounds are used as the light emitting auxiliary layer material, respectively. That is, when Comparative Compound C was used, compared to when Comparative Compound A or Comparative Compound C was used as a light emitting auxiliary layer material, the driving voltage was lowered, luminous efficiency and lifespan were improved, and compared with the case of using Comparative Compound C, When the compound was used, the device characteristics were the best.

The reason that the device characteristics of the example using the compound of the present invention are improved compared to Comparative Example 4 using Comparative Compound C as a light emitting auxiliary layer material is that when the 2-carbazole derivative is bonded to the 5-ring heterocyclic core, 3-carbazole It is considered that this is because the conjugation length becomes shorter than when the sol derivative is bound, and as a result, the bandgap is widened, the T1 value is increased, and energy levels such as HOMO and LUMO are different.

Therefore, the changed physical properties of the compound of the present invention act as a major factor (eg, energy balance, hole mobility, electron mobility) to improve the performance of the device when the compound is deposited in the device manufacturing process, resulting in improved driving voltage, efficiency, and lifespan. seems to derive

The above description is merely 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 intended to illustrate, not to limit the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

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

Claims (10)

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

In Formula 1,
X ¹ and X ² are each independently O or S,
R ³ to R ⁵ are each independently i) hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L'-N(R _a )(R _b ); or ii) adjacent groups are bonded to each other to C ₆ to C ₆₀ aromatic hydrocarbons, fluorene, O, N, S, Si And a C ₂ ~ C ₆₀ heterocyclic group comprising at least one heteroatom of P, a C ₃ ~ C ₆₀ aliphatic ring, or a C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ fusion of an aromatic ring can form a ring,
c and e are each an integer of 0-3, d is an integer of 0-2, and when c, d, and e are each an integer of 2 or more, a plurality of R ² , a plurality of R ³ , a plurality of R ⁴ , or a plurality of R ⁵ are each the same as or different from each other,
Ar ¹ and Ar ² are each independently represented by Formula 2 or Formula 3, provided that Ar ¹ and Ar ² are different from each other,
<Formula 2><Formula3>

In Formula 2 and Formula 3,
Ar ³ To Ar ⁵ Are each independently a C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; -L'-N(R _a )(R _b ); And -L'-S (R _a ) is selected from the group consisting of,
L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; and C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring is selected from the group consisting of,
R ¹ and R ² are independently of each other i) hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L'-N(R _a )(R _b ); or ii) adjacent groups are bonded to each other to C ₆ to C ₆₀ aromatic hydrocarbons, fluorene, O, N, S, Si And a C ₂ ~ C ₆₀ heterocyclic group comprising at least one heteroatom of P, a C ₃ ~ C ₆₀ aliphatic ring, or a C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ fusion of an aromatic ring may form a cyclic group, each a is an integer of 0 to 3, b is an integer of 0 to 4, and when a and b are each an integer of 2 or more, each of a plurality of R ¹ or a plurality of R ² is the same as each other, or different,
The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; It is selected from the group consisting of a fused ring group of C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring,
The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; It is selected from the group consisting of a fused ring group of C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring,
The R ¹ to R ⁵ , R _a , R _b , Ar ³ to Ar ⁵ , L ¹ , L ² , L′, and the adjacent R ¹ to the adjacent R ⁵ rings formed by bonding to each other are deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; a phosphine oxide group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl 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; a C ₆ -C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C ₂₀ An aryl alkenyl group; may be further substituted with one or more substituents selected from the group consisting of. The method of claim 1,
Formula 1 is a compound, characterized in that represented by Formula 4 or Formula 5:
<Formula 4><Formula5>

In Chemical Formulas 4 and 5,
X ¹ , X ² , R ¹ to R ⁵ , Ar ³ to Ar ⁵ , L ¹ , L ² , a, b, c, d and e are as defined in claim 1 . 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 positioned between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising the compound of any one of claims 1 to 3. 5. The method of claim 4,
The compound is included in at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer of the organic material layer,
The compound is an organic electric device, characterized in that it is included as a single compound or a mixture of two or more. 6. The method of claim 5,
The compound is an organic electric device, characterized in that included in the light emitting auxiliary layer. 5. The method of claim 4,
The organic electric device further comprising a light efficiency improving layer formed on at least one surface opposite to the organic material layer among one surface of the first electrode and the second electrode. 5. The method of claim 4,
The organic material layer is an organic electric device, characterized in that 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
An electronic device comprising a; a control unit for driving the display device. 10. The method of claim 9,
The organic electroluminescent device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and an electronic device, characterized in that at least one of a single color or white lighting device.

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