KR102389204B1 - Compound for organic electronic element, organic electronic 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, 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 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.

In addition, the light emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the light emission mechanism. can In addition, the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color according to the emission color.

On the other hand, when only one material is used as a light emitting material, the maximum emission wavelength is shifted to a longer wavelength due to intermolecular interaction, and there is a problem in that the color purity is lowered or the efficiency of the device is reduced due to the emission attenuation effect. A host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through the The principle is that when a small amount of a dopant having a smaller energy band gap than that of the host forming the emission layer is mixed in the emission layer, excitons generated in the emission layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

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 between each organic material layer, the T ₁ value, and the intrinsic properties (mobility, interfacial properties, etc.) of the material 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 in the hole transport layer in recent general organic light emitting devices, it is preferable that a light emitting auxiliary layer is present between the hole transport layer and the light emitting layer, and each light emitting layer (R, G, B) according to each other It is time to develop another light emitting auxiliary layer.

In order to fully exhibit the excellent characteristics of an organic electric device, the material constituting the organic layer in the device, for example, a hole injection material, a hole transport material, a light emitting auxiliary layer material, a light emitting layer material, an electron transport material, an electron transport auxiliary material, an electron injection material, etc. It should be supported by stable and efficient materials, but the development of stable and efficient organic material layer materials for organic electric devices has not yet been sufficiently developed. Therefore, the development of new materials is continuously required, in particular, the development of materials for the light-emitting auxiliary layer and the light-emitting layer is urgently required, and in particular, the development of the host material of the light-emitting layer is desperately 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 (1).

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 greatly improved.

1 is an exemplary view 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 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.

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 one or more heteroatoms 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 (monocyclic or fused ring systems) directly connected to each other through single or double bonds, 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.

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 includes 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 sequentially stacked on the first electrode 120 , and these layers At least one layer may be omitted, and 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 , and the like. In this case, the electron transport layer 160 and the like may serve as a hole blocking layer, and the hole transport layer 140 and the electron transport layer 160 may be formed of one or more layers.

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 of the light emitting layer 150, the hole transport layer 140 and/or the light emission auxiliary layer 151, preferably the host material of the light emitting layer 150 or the light emission auxiliary layer 151. can be used as a material for

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 emitting layer 150 or the light emission auxiliary layer 151 using the compound represented by Formula 1, the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) It is possible to simultaneously improve the lifespan and efficiency of the organic electric device by optimizing it.

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.

R ¹ to R ⁵ are each independently 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 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 ); is selected from the group consisting of, and R ¹ and R ² or R ³ and R ⁴ may be bonded to each other to form a ring. A ring formed by bonding R ¹ and R ² or R ³ and R ⁴ to each other may be benzene, naphthalene, phenanthrene, fluorene, or the like.

m and n are each an integer of 1-6.

When m is an integer of 2 or more, each of a plurality of R ¹ to R ⁵ and L ¹ is the same as or different from each other. In addition, when n is an integer of 2 or more, a plurality of R ⁵ are the same as or different from each other, and adjacent R ⁵ may be bonded to each other to form a ring, in this case, the ring formed by bonding adjacent R ⁵ to each other is benzene, It may be naphthalene, phenanthrene, fluorene, or the like.

When R ¹ to R ⁵ are an aryl group, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, for example, phenyl, naphthyl, phenanthrene, triphenyl Ren or the like. When R ¹ to R ⁵ are a heterocyclic group, preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, for example, triazine, dibenzothiophene , benzonaphthofuran, and the like. When R ¹ to R ⁵ is a fluorenyl group, it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9′-spirobifluorene, or the like. When R ¹ to R ⁵ are an alkyl group, it may be preferably a C ₁ -C ₁₀ alkyl group, more preferably a C ₁ -C ₄ alkyl group, for example, a methyl group or a t-butyl group.

L ¹ 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; and a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group; may be selected from the group consisting of.

When L ¹ is an arylene group, it is preferably a C ₆ -C ₃₀ arylene group, more preferably a C ₆ -C ₁₈ arylene group, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, and triphenylene. When L ¹ is a heterocyclic group, it is preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, illustratively pyridine, pyrimidine, triazine, quinazoline, benzoquinazoline, dibenzoquinazoline, carbazole, benzothienopyrimidine, benzofuropyrimidine, dibenzothiophene, dibenzofuran, or the like. When L ¹ is a fluorenylene group, it may be 9,9-dimethyl-9H-fluorene.

Ar ¹ is 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 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 ); may be selected from the group consisting of.

When Ar ¹ is an aryl group, it may be a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, for example, phenyl, naphthalene, biphenyl, phenanthrene, triphenylene. , terphenyl, and the like. When Ar ¹ is a heterocyclic group, it may be a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, for example, pyridine, pyrimidine, triazine, quinazoline. , benzoquinazoline, dibenzoquinazoline, quinoxaline, isoquinoline, imidazopyridinebazole, benzoimidazole, dibenzothiophene, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, 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; and a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group; may be selected from the group consisting of.

When L' is an arylene group, it is preferably a C ₆ -C ₃₀ arylene group, more preferably a C ₆ -C ₁₈ arylene group, and may be exemplarily phenyl, biphenyl, terphenyl, naphthalene, or 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; and a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group; may be selected from the group consisting of.

When R _a and R _b are an aryl group, they may be preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₂ aryl group, and may be exemplarily phenyl or biphenyl. When R _a and R _b are a heterocyclic group, preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, for example, carbazole, dibenzothiophene , benzonaphthofuran, etc., and may be 9,9-dimethyl-9H-fluorene when R _a and R _b are fluorenyl groups.

The R ¹ to R ⁵ , L ¹ , Ar ¹ , L′, R _a , R _b , R ¹ and R ² are bonded to each other, a ring formed by bonding to each other, R ³ and R ⁴ are bonded to each other, a ring formed, and the neighboring R ⁵ rings formed by bonding to each other are each 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; 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; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof.

Formula 1 may be represented by one of Formulas 2 to 4 below.

<Formula 2> <Formula 3> <Formula 4>

In Formulas 2 to 4, R ⁵ , L ¹ , Ar ¹ , m and n are as defined in Formula 1.

In the above formula, Ar ¹ may be one of the following formulas a to j.

<Formula a> <Formula b> <Formula c> <Formula d> <Formula e>

<Formula f> <Formula g> <Formula h> <Formula i> <Formula j>

In Formulas a to j, X ¹ to X ⁷ are N or C(R′), and Y is O, S or N(Ar ³ ).

Ar ² and Ar ³ 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 heterocyclic group C ₃ ~ C ₆₀ A fused ring group of an 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 Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ); may be selected from the group consisting of.

wherein R' is 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 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 ) ^; as defined

When m=2 in Formula 1, Formula 1 may be represented by Formula 5 below.

<Formula 5>

In Formula 5, R ¹ to R ⁵ , L ¹ , Ar ¹ , m and n are as defined in Formula 1.

In Formula 1, when Ar ¹ is -L′-N(R _a )(R _b ), Formula 1 may be represented by Formula 6 below, and R ⁵ is -L′-N(R _a )(R In the case of _b ), Chemical Formula 1 may be represented by Chemical Formula 7 below.

<Formula 6> <Formula 7>

In Formulas 6 and 7, R ¹ to R ⁵ , L ¹ , Ar ¹ , m , n, L′, R _a and R _b are as defined in Formula 1.

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

.

.

In another aspect of the present invention, the present invention provides an organic electric device comprising 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 is a compound according to the present invention includes

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, in the form of a single compound or a mixture of two or more It may be included, and preferably, the compound represented by Formula 1 may be used as a host material of the light emitting layer and/or a material of the light emission auxiliary layer.

In another aspect of the present invention, the present invention provides an electronic device including a display device including the organic electric device of claim 7 and a control unit for driving the display device.

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

Illustratively, the compound represented by Formula 1 according to the present invention (final product) may be prepared by reacting Sub 1 with Sub 2 or Sub 3 as shown in Scheme 1 below.

<Scheme 1>

Sub 1 Synthesis example

Sub 1 of Scheme 1 may be synthesized by the reaction routes of Schemes 2 to 4, but is not limited thereto.

<Scheme 2>

Sub 1-1-1 Synthesis Example

After dissolving 2-Bromo-1,1'-biphenyl (177.32 g, 760.7 mmol) in THF (2,500 mL), the temperature of the reaction mass was lowered to -78 ° C., and n-BuLi (324.56 mL, 2.5M in hexane) was added. After the slow dropwise addition, the reaction was stirred for 1 hour. 1,8-naphthalimide (100.0 g, 507.1 mmol) was dissolved in THF and then injected into the reaction mixture and stirred at room temperature for 4 hours. When the reaction was completed, water was added to the reactant to quench it, then water in the reactant was removed, filtered under reduced pressure, the organic layer was dried over MgSO ₄ , and concentrated to obtain 160.39 g of a product (yield: 90%).

Sub 1-2-1 Synthesis Example

Sub 1-1-1 (160.39 g, 456.4 mmol) obtained in the above synthesis was placed in a round-bottom flask and dissolved with acetic acid (2,000 mL), conc. A few drops of HCl were added slowly and stirred at 80°C. When the reaction was completed, the reaction was neutralized with an aqueous solution of Na ₂ SO ₄ , extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 132.38 g (yield: 87%) of the product.

Sub 1-3-1 Synthesis Example

Sub 1-2-1 (132.38g, 397.1 mmol) obtained in the above synthesis was dissolved in THF (2,000 mL), the temperature of the reaction product was lowered to -78°C, and 2-biphenylmagnesium bromide solution (122.65g, 476.5 mmol) was added. After the slow dropwise addition, the reaction mixture was stirred for 1 hour and stirred at room temperature for 4 hours. When the reaction was completed, water was added to the reactant to quench it, and then water in the reactant was removed, filtered under reduced pressure, dried over MgSO4 and concentrated to obtain 162.63 g (yield: 84%) of a product.

Sub 1(21) synthesis example

Sub 1-3-1 (162.63 g, 333.5 mmol) obtained in the above synthesis was placed in a round-bottom flask and dissolved with acetic acid (1,500 mL), conc. A few drops of HCl were added slowly and stirred at 80°C. When the reaction was completed, the reaction was neutralized with an aqueous solution of Na ₂ SO ₄ , extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 126.86 g (yield: 81%) of the product.

<Scheme 3>

Sub 1-1-2 Synthesis Example

1,8-naphthalimide (100.0g, 507.1 mmol), Potassium hydroxide (142.27g, 2,535.6 mmol), hydrazine monohydrate (761.60g, 15,213.8 mmol), and ethylene glycol (2,500 mL) were placed in a round-bottom flask and heated to 180℃. was raised and stirred for 24 hours. When the reaction was completed, water was added to the reactant to quench it, and then water in the reactant was removed, filtered under reduced pressure, and the compound was recrystallized using silicagel column to obtain 52.35 g (yield: 61%) of the product.

Sub 1(1) synthesis example

Sub 1-1-2 (52.35 g, 309.3 mmol) obtained in the above synthesis was placed in a round bottom flask, iodomethane (263.43 g, 1,856.1 mmol), KO(t-Bu) (208.27 g, 1,856.1 mmol), dimethylsulfoxide (1,500) mL), the temperature was raised to 140 °C, and the mixture was stirred for 24 hours. When the reaction is completed, 3L of water is added to each of the two 5L beakers, and the reactant is solidified while stirring. Thereafter, the precipitated reactant was filtered, and only the filtered solid was collected and recrystallized by silicagel column to obtain 89.72 g (yield: 87%) of the product.

<Scheme 4>

Sub 1-1-3 Synthesis Example

After 1,8-napthalimide (100g, 507.1 mmol) was dissolved in THF (2,500 mL), the temperature of the reaction mass was lowered to -78°C, phenylmagnesium bromide solution (183.89 g, 1,014.3 mmol) was slowly added dropwise, and the reaction mass was allowed to stand for 1 hour. After stirring for 4 hours at room temperature. When the reaction was completed, water was added to the reactant to quench it, then water in the reactant was removed, filtered under reduced pressure, the organic layer was dried over MgSO ₄ , and concentrated to obtain 128.45 g of a product (yield: 92%).

Sub 1-2-2 Synthesis Example

After dissolving Sub 1-1-3 (128.45 g, 466.6 mmol) obtained in the above synthesis in THF (2,000 mL), the temperature of the reaction product was lowered to -78°C, and phenylmagnesium bromide solution (169.19 g, 933.1 mmol) was slowly added dropwise. After the reaction was stirred for 1 hour, the mixture was stirred at room temperature for 4 hours. When the reaction was completed, water was added to the reactant to quench it, and then water in the reactant was removed, filtered under reduced pressure, the organic layer was dried over MgSO ₄ , and concentrated to obtain 145.11 g of a product (yield: 88%).

Sub 1(11) synthesis example

Sub 1-2-2 (145.11g, 410.6 mmol) obtained in the above synthesis is placed in a round-bottom flask, Benzene (1,500 mL) is added, and heated to 50° C. to dissolve. Trifluoromethanesulfonic acid (67.78 g, 451.6 mmol) was slowly added, followed by stirring for 2 hours. When the reaction was completed, the reactant was poured into an aqueous sodium bicarbonate solution for neutralization, and then the organic layer was separated, and through the column, 138.07 g of Sub 3 product (yield: 71%) was obtained.

Examples of Sub 1 are as follows, but are not limited thereto, and FD-MS values for these compounds are shown in Table 1.

[Table 1]

Sub 2 example

Examples of compounds belonging to Sub 2 are as follows, but are not limited thereto, and FD-MS values for these compounds are shown in Table 2 below.

[Table 2]

Sub 3's Synthesis example

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

<Scheme 3>

Sub 3(2) Synthesis example

Sub 1(21) (22.2g, 47.3 mmol) was placed in a round-bottom flask and dissolved in toluene (500 mL), 1-bromo-4-iodobenzene (14.7g, 52.0 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol), P( t -Bu) ₃ (1.1 g, 5.2 mmol), NaO t -Bu (15 g, 156.1 mmol) were added and stirred at 100°C. Upon completion of the reaction, the reaction was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 19.5 g (yield: 66%) of the product.

Sub 3's Synthesis example

Examples of compounds belonging to Sub 3 are as follows, but are not limited thereto, and FD-MS values for these compounds are shown in Table 3 below.

[Table 3]

final compound Synthesis example

Compound 1-1 Synthesis Example

Sub 1(2) (14.3 g, 47.3 mmol) was placed in a round-bottom flask and dissolved in toluene (500 mL), Sub 2-1 (8.2 g, 52.0 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6) mmol), P( t -Bu) ₃ (1.1 g, 5.2 mmol), and NaO t -Bu (15 g, 156.1 mmol) were added and stirred at 100°C. After completion of the reaction, extraction with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized by silicagel column to obtain 11.7 g (yield: 65%) of the product.

Compound 1-11 Synthesis Example

Using Sub 1(4) (21.6 g, 47.3 mmol) and Sub 2-63 (18.3 g, 52.0 mmol), 24.1 g (yield: 66%) of the product was obtained in the same manner as in Synthesis Example 1-1.

Compound 1-18 Synthesis Example

17.3 g (yield: 69%) of the product was obtained by the same synthesis method as in Synthesis Example 1-1, using Sub 1(1) (10.7 g, 47.3 mmol) and Sub 2-54 (17.7 g, 52.0 mmol).

Compound 1-36 Synthesis Example

Using Sub 1(1) (10.7 g, 47.3 mmol) and Sub 2-58 (26.9 g, 52.0 mmol), 21.3 g (yield: 68%) of the product was obtained in the same manner as in Synthesis Example 1-1.

Compound 1-41 Synthesis Example

Sub 1 (31) (26.4 g, 47.3 mmol) and Sub 2-2 (10.8 g, 52.0 mmol) were synthesized in the same manner as in Synthesis Example 1-1 to obtain 20.4 g (yield: 63%) of the product.

Compound 2-4 Synthesis Example

Sub 1 (11) (22.4 g, 47.3 mmol) and Sub 2-4 (12.1 g, 52.0 mmol) were synthesized in the same manner as in Synthesis Example 1-1 to obtain 20.1 g (yield: 68%) of the product.

Compound 2-10 Synthesis Example

Using Sub 1(11) (22.4 g, 47.3 mmol) and Sub 2-64 (14.2 g, 52.0 mmol), 21.1 g (yield: 67%) of the product was obtained in the same manner as in Synthesis Example 1-1.

Compound 2-25 Synthesis Example

Using Sub 1 (19) (22.7 g, 47.3 mmol) and Sub 2-10 (10.2 g, 52.0 mmol), 23.1 g (yield: 62%) of the product was obtained in the same manner as in Synthesis Example 1-1.

Compound 2-39 Synthesis Example

Sub 1 (11) (22.4 g, 47.3 mmol) and Sub 2-61 (28.1 g, 52.0 mmol) were used to obtain 28.2 g (yield: 64%) of the product in the same manner as in Synthesis Example 1-1.

Compound 2-43 Synthesis Example

Sub 1 (32) (31.7 g, 47.3 mmol) and Sub 2-65 (18.2 g, 52.0 mmol) were used to obtain 27.9 g (yield: 60%) of the product in the same manner as in Synthesis Example 1-1.

Compound 3-3 Synthesis Example

19.4 g (yield: 69%) of the product was obtained in the same manner as in Synthesis Example 1-1, using Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-3 (10.8 g, 52.0 mmol).

Compound 3-7 Synthesis Example

Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-66 (16.8 g, 52.0 mmol) were used to obtain 22.9 g (yield: 65%) of the product in the same manner as in Synthesis Example 1-1.

Compound 3-13 Synthesis Example

Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-15 (14.8 g, 52.0 mmol) were used to obtain 22.0 g (yield: 69%) of the product in the same manner as in Synthesis Example 1-1.

Compound 3-16 Synthesis Example

Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-67 (15.4 g, 52.0 mmol) were used to obtain 23.1 g (yield: 67%) of the product in the same manner as in Synthesis Example 1-1.

Compound 3-36 Synthesis Example

Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-58 (26.9 g, 52.0 mmol) were used to obtain 27.8 g (yield: 65%) of the product in the same manner as in Synthesis Example 1-1.

Compound 3-44 Synthesis Example

Sub 1 (33) (38.5 g, 47.3 mmol) and Sub 2-4 (12.1 g, 52.0 mmol) were used to obtain 28.8 g (yield: 63%) of the product in the same manner as in Synthesis Example 1-1.

Compound 4-4 Synthesis Example

Using Sub 1 (21) (22.2 g, 47.3 mmol) and Sub 2-68 (36.4 g, 52.0 mmol), 30.4 g (yield: 59%) of the product was obtained in the same manner as in Synthesis Example 1-1.

FD-MS values of compounds 1-1 to 4-12 of the present invention prepared according to the above synthesis examples are shown in Table 4 below.

[Table 4]

Manufacturing evaluation of organic electric devices

[ Example 1] Green organic electroluminescent device (phosphorescent host)

First, on an ITO layer (anode) formed on a glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ - A phenylbenzene-1,4-diamine (hereinafter abbreviated as '2-TNATA') film was vacuum-deposited to form a hole injection layer with a thickness of 60 nm.

Thereafter, a 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as 'NPD') film on the hole injection layer was vacuum deposited to a thickness of 60 nm to form a hole transport layer. formed.

Next, using compound 1-6 of the present invention as a host material and tris(2-phenylpyridine)-iridium (hereinafter abbreviated as “Ir(ppy) ₃ ”) as a dopant material on the hole transport layer 95 A light emitting layer with a thickness of 30 nm was deposited by doping at a weight ratio of :5.

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

Thereafter, LiF 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 on the electron injection layer to a thickness of 150 nm to form a cathode.

[ Example 2] to [ Example 8] Green organic electroluminescent device

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

[ comparative example One]

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

<Comparative compound 1>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 8 and Comparative Example 1 of the present invention, the electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch company, The T95 lifetime was measured using a lifetime measuring device manufactured by McScience at 5000cd/m ² standard luminance, and the measurement results are shown in Table 5 below.

[Table 5]

[ Example 9] Red Organic electroluminescent device (phosphorescent host)

After vacuum deposition of 2-TNATA on the ITO layer (anode) formed on the glass substrate to form a 60 nm-thick hole injection layer, 4,4-bis[ N -(1-naphthyl)- N -phenylamino]biphenyl (hereinafter abbreviated as 'NPB') was vacuum-deposited to a thickness of 60 nm to form a hole transport layer, and then compound 1-14 of the present invention as a host material on the hole transport layer, bis- ( 1-phenylisoquinoline)iridium(III)acetylacetonate (hereinafter, “(piq) ₂ Ir(acac)”) was used as a dopant material and doped at a 95:5 weight ratio to form a 30 nm thick light emitting layer.

Next, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was formed on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

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

[ Example 10] to [ Example 19] Green organic electroluminescent device

An organic electroluminescent device was manufactured in the same manner as in Example 9, except that the compound of the present invention shown in Table 6 was used instead of the compound 1-14 of the present invention as the host material of the light emitting layer.

[ comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 9, except that Comparative Compound 1 was used instead of Compound 1-14 of the present invention as a host material for the emission layer.

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 9 to 19 and Comparative Example 2 of the present invention, the electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, At 2500cd/m ² standard luminance, the T95 lifetime was measured using a lifetime measuring device manufactured by McScience, and the measurement results are shown in Table 6 below.

[Table 6]

[ Example 20] Green organic electroluminescent device ( light emitting layer )

After vacuum deposition of 2-TNATA on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 60 nm, vacuum deposition of NPD to a thickness of 60 nm on the hole injection layer to form a hole transport layer, Then, the compound 1-33 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light emitting auxiliary layer.

Next, on the light emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as 'CBP') as a host material and Ir(ppy) ₃ as a dopant material were used as 95 A light emitting layer with a thickness of 30 nm was formed by doping at a weight ratio of :5.

Next, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq ₃ was formed on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

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

[ Example 21] to [ Example 31] Green organic electroluminescent device ( light emitting layer )

An organic electroluminescent device was manufactured in the same manner as in Example 20, except that the compound of the present invention shown in Table 7 was used instead of compound 1-33 of the present invention as a material of the light emitting auxiliary layer.

[ comparative example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 20, except that the light-emitting auxiliary layer was not formed.

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 20 to 31 and Comparative Example 3 of the present invention, the electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, At 5000cd/m ² standard luminance, T95 lifetime was measured using a lifetime measuring device manufactured by McScience, and the measurement results are shown in Table 7 below.

[Table 7]

From Tables 5 to 7, the luminous efficiency and lifespan of the organic electroluminescent device according to the embodiment of the present invention using the material for an organic light emitting device of the present invention as a phosphorescent host or a light emitting auxiliary layer material is an organic electroluminescent device of Comparative Example. It can be seen that the improvement is significantly improved and the driving voltage is lowered.

This is because the compound of the present invention having a wide band gap has suitable physical properties as a phosphorescent host or light emitting auxiliary layer material, that is, an appropriate energy level (eg, HOMO, LUMO, T1). It seems to be because it acts as a major factor (eg energy balance, hole mobility, electron mobility).

The above description is merely illustrative of the present invention, and various modifications will be possible without departing from the essential characteristics of the present invention by those skilled in the art to which the present invention pertains. 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 (13)

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

In Formula 1,
R ¹ To R ⁴ Are each independently a C ₆ ~ C ₃₀ Aryl group; fluorenyl group; and C ₁ to C ₁₀ selected from the group consisting of an alkyl group, and R ¹ and R ² or R ³ and R ⁴ may be bonded to each other to form a ring,
R ⁵ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₃₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₃₀ A heterocyclic group; C ₁ ~ C ₁₀ Alkyl group; and -L′-N(R _a )(R _b ),
m and n are each an integer of 1 to 2, and when R ⁵ is deuterium, n is an integer of 1 to 6,
When m is an integer of 2 or more, each of a plurality of R ¹ to R ⁵ and L ¹ is the same as or different from each other,
When n is an integer of 2 or more, a plurality of R ⁵ may be the same as or different from each other, and adjacent R ⁵ may be bonded to each other to form a ring,
L ¹ is a single bond; C ₆ ~ C ₃₀ Arylene group; fluorenylene group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C ₃₀ It is selected from the group consisting of a heterocyclic group,
Ar ¹ is a C ₆ ~ C ₃₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₃₀ A heterocyclic group; And -L'-N(R _a ) (R _b ) is selected from the group consisting of,
Wherein L 'is a single bond or C ₆ ~ C ₃₀ Arylene group,
The R _a and R _b are each independently a C ₆ ~ C ₃₀ aryl group; fluorenyl group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C ₃₀ It is selected from the group consisting of a heterocyclic group,
The R ¹ to R ⁵ , L ¹ , Ar ¹ , L′, R _a , R _b , R ¹ and R ² are bonded to each other to form a ring, R ³ and R ⁴ are bonded to each other to form a ring, and the neighboring R ⁵ rings formed by bonding to each other are each deuterium; halogen; cyano group; nitro group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl 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; And it may be substituted with one or more substituents selected from the group consisting of a C ₃ -C ₂₀ cycloalkyl group. The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 2 to 4:
<Formula 2><Formula3><Formula4>

In Formulas 2 to 4, R ⁵ , L ¹ , Ar ¹ , m and n are the same as defined in claim 1. The method of claim 1,
Wherein Ar ¹ is a compound characterized in that one of the following formulas a to j:
<Formula a><Formulab><Formulac><Formulad><Formulae>

<Formula f><Formulag><Formulah><Formulai><Formulaj>

In the above formulas a to j,
X ¹ To X ⁷ are N or C (R '), Y is O, S or N (Ar ³ ),
Ar ² and Ar ³ are each independently a C ₆ -C ₂₀ aryl group; fluorenyl group; And it is selected from the group consisting of a C ₂ -C ₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P,
wherein R' is hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₂₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₂₀ A heterocyclic group; C ₁ ~ C ₂₀ Alkyl group; and C ₁ to C ₂₀ selected from the group consisting of an alkoxyl group, and adjacent R′ may be bonded to each other to form a ring. The method of claim 1,
Formula 1 is a compound, characterized in that represented by the following formula 5:
<Formula 5>

In Formula 5, R ¹ to R ⁵ , L ¹ , Ar ¹ , and n are the same as defined in claim 1. The method of claim 1,
Formula 1 is a compound, characterized in that represented by Formula 6 or Formula 7:
<Formula 6><Formula7>

In Formulas 6 and 7, R ¹ to R ⁵ , L ¹ , Ar ¹ , m , n, L′, R _a and R _b are as defined in claim 1 . The method of claim 1,
Formula 1 is a compound, characterized in that one of the following compounds:

. a first electrode; a second electrode; and an organic material layer formed 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 6. 8. The method of claim 7,
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 two or more types An organic electric device, characterized in that it is included as a mixture. 9. The method of claim 8,
The compound is an organic electric device, characterized in that used as a host material of the light emitting layer or a material of the light emitting auxiliary layer. 8. The method of claim 7,
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. 8. The method of claim 7,
The organic electric device further comprising a light efficiency improving layer formed on at least one surface opposite to the organic material layer of one surface of the first electrode and the second electrode. A display device comprising the organic electric device of claim 7; and
An electronic device comprising a; a control unit for driving the display device. 13. The method of claim 12,
The organic electric device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and an electronic device, characterized in that one of a monochromatic lighting device.

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