WO2015083948A1 - Compound for organic electric element, organic electric element using same, and electronic device thereof - Google Patents

Abstract

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

Description

Compound for organic electric element, organic electric element using same and 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, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, 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, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

The material used as the organic material layer in the organic electric device may be classified into a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material and the like according to a function.

The biggest problem for organic electric devices is life and efficiency. As the display becomes larger, these efficiency and life problems must be solved.

Efficiency, lifespan, and driving voltage are related to each other.As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Jouleheating generated during driving decreases, resulting in a lifetime. This tends to be higher. However, simply improving the organic layer may not maximize the efficiency. Because of the optimal combination of energy level, T ₁ value, and intrinsic properties (mobility, interfacial properties, etc.) between organic layers, long life and high efficiency can be achieved simultaneously. Because.

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 to generate excitons by recombination.

However, holes move faster than electrons, and excitons generated in the emission layer are transferred to the electron transport layer, resulting in charge unbalance in the emission layer, thereby emitting light at the electron transport layer interface.

When emitting light at the electron transport layer interface, there is a problem that the color purity and efficiency of the organic electroluminescent device is deteriorated, and in particular, when the organic electroluminescent device is manufactured, a problem arises that the lifetime of the organic electroluminescent device is shortened due to the high temperature stability. Therefore, it is time to develop an electron transport material that has high temperature stability and high electron mobility and improves hole blocking ability with a high T1 value.

The present invention provides a compound having high electron mobility and high temperature stability and having a more efficient electron transport ability with a high T ₁ value, and using the compound, an organic electric device having improved efficiency, lifetime and color purity, and an electron including the same. It is an object to provide a device.

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

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

According to the present invention, it is possible to provide a compound having high electron mobility and high temperature stability and more efficient electron transport ability with a high T ₁ value, and by using such a compound, it is possible to improve the efficiency, lifespan and color purity of the device.

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

Hereinafter, exemplary 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 reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, in describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

As used in this specification and the appended claims, unless otherwise indicated, the meanings of the following terms are as follows:

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

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

As used herein, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

As used herein, the term "heteroalkyl group" means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.

As used herein, the term "alkenyl group" or "alkynyl group", unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.

The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.

As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.

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

As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto. In the present invention, an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.

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

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

As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.

As used herein, the term “heterocyclic group” includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.

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

"Heterocyclic groups" may also include rings comprising SO ₂ in place of the carbon forming the ring. For example, a "heterocyclic group" includes the following compounds.

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

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

Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.

Unless otherwise stated, the term "carbonyl" used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise specified, the term "ether" as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ arylthiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Group, germanium group, and C ₂ ~ C _{20 It} is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.

Also, unless otherwise stated, the formulas used in the present invention apply equally to the definitions of substituents based on the exponential definition of the following formulas.

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

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

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

The organic layer may 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 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.

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

The compound according to the present invention applied to the organic material layer of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the host of the dopant or light efficiency improvement layer of the light emitting layer 150 Can be used as a material.

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

In addition, the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.

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

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

In addition, the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.

Another embodiment of the present invention may include a display device including the organic electric element 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 or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the compound which concerns on one aspect of this invention is demonstrated.

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

[Formula 1]

In Chemical Formula 1,

R ¹ and R ² independently of each other deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; And C ₆ ~ C ₃₀ An aryloxy group; It is selected from the group consisting of, m is an integer of 0 to 4, n is an integer of 0 to 6.

When n is an integer of 2 or more, a plurality of R ¹ may be the same or different from each other, and a plurality of R ^{2 may} also be the same or different from each other. When R ¹ and R ² are an aryl group, C ₆ ~ C _{60 It} may be an aryl group, preferably C ₆ ~ C _{30 It} may be an aryl group, more preferably C ₆ ~ C _{15 It} may be an aryl group. Further, when R ¹ and R ² are heterocycles, C ₂ ~ C ₆₀ heterocyclic group, preferably C ₂ ~ C ₃₀ heterocyclic group, more preferably C ₂ ~ C ₂₀ heterocyclic group, more Preferably it may be a C ₃ ~ C ₁₅ heterocyclic group. For example, R ¹ and R ² are independently of each other aryl such as phenyl, biphenyl, anthracene, phenanthrene, or the like, or hetero, such as pyridine, quinoline, phenanthroline, dibenzothiophene, dibenzofuran, triazine, quinazoline, or the like. It may be a ring.

In Formula 1, L ¹ and L ² are each independently a single bond; C ₆ ~ C ₆₀ aromatic ring; Fluorene; C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C ₆₀ fused ring of an aromatic ring; And C ₂ ~ C ₆₀ heterocycle including at least one heteroatom of O, N, S, Si, and P, each of which may be selected from deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C ₁ ~ C ₂₀ of the import alkylthio; C ₁ -C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₆ -C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; It may be substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group.

On the other hand, when L ¹ is a single bond, L ² is bonded to L ¹ , which is a single bond, and thus L ² is the same as that directly bonded to the benzoacridin skeleton. Similarly, L ² is a single bond, the same as the Ar ¹ are the same as those that are directly coupled to L ^1, the case that L ¹ and L ² are both a single bond the Ar ¹ that is directly coupled to Ben Joa acridine skeleton Done.

On the other hand, L ² may vary in valence depending on x. For example, when x is 1, L ² may be bivalent, x is 2, trivalent, and x may be tetravalent. Of course, when L ² is a single bond, L ¹ may also have a different valence depending on x. For example, when x is 1, L ¹ may be bivalent, x is 2, trivalent, and x may be tetravalent. will be. In addition, when L ² is not a single bond, L ¹ may be a single bond or a divalent group.

L ¹ and L ² may be an aromatic ring of C ₆ ~ C ₆₀ , preferably an aromatic ring of C ₆ ~ C ₃₀ , more preferably may be an aromatic ring of C ₆ ~ C ₂₀ .

Further, L ¹ and L ² may be a C ₂ ~ C ₆₀ heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₀ heterocyclic group, more preferably May be a heterocyclic group of C ₃ ~ C ₁₅ .

L ¹ is, for example, a divalent benzene ring, naphthylene, anthracene, phenanthrene, perylene, triphenylene, pyrene, benzophenanthrene, fluorene, pyridine, pyrimidine, pyridazine, triazine, benzoacridine , Quinazoline, quinoline, isoquinoline, quinoxaline, 2,6-naphthyridine, pyrido [2,3- d ] pyrimidine, pyrido [3,4- d ] pyrimidine, phenanthridine, benzo [ h ] Quinazolin, pyrrole, imidazole, triazole, thiophene, isoxazole, 1,3,4-thiadiazole, 1 H -benzo [ d ] imidazole, benzo [ d ] oxazole, benzo [ d ] thiazol or derivatives thereof, and L ² is a divalent to tetravalent benzene ring, naphthalene, anthracene, phenanthrene, perylene, triphenylene, pyrene, benzophenanthrene, Fluorene, pyridine, pyrimidine, pyridazine, triazine, benzoacridine, quinazoline, quinoline, isoquinoline, quinoxaline, 2,6-naphthyridine, pyrido [2,3- d ] pyrimidine, pyridine Degree [3,4- d ] pyrimi Dine, phenanthridine, benzo [ h ] quinazolin, pyrrole, imidazole, triazole, thiophene, isoxazole, 1,3,4-thiadiazole, 1 H − Benzo [ d ] imidazole, benzo [ d ] oxazole, benzo [ d ] thiazol or derivatives thereof and the like.

In Formula 1, Ar ¹ is a C ₆ ~ C ₆₀ An aryl group; Fluorenyl group; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And a C ₂ -C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P. When Ar ¹ is an aryl group, C ₆ ~ C _{60 It} may be an aryl group, preferably C ₆ ~ C _{30 It} may be an aryl group, more preferably C ₆ ~ C ₁₅ aryl group, more preferably C _It may be an aryl group of ₆ ~ C ₁₀ . In addition, when Ar ¹ is a heterocycle, a C ₂ ~ C ₆₀ heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₀ heterocyclic group, more preferably C ₃ ~ C _{15 It} may be a heterocyclic group.

X, which is an index of Ar ¹ , is an integer of 1 to 3. Provided that when L ¹ and L ² are both single bonds, x is an integer of 1. Thus, 1 to 3 Ar ¹ may be bonded to L ² . However, L ² is the case of a single bond, the Ar ¹ is the same as directly bonded to L ^1, the case that L ¹ and L ² are both a single bond, the Ar ¹ is the same as directly bonded to Ben Joa acridine skeleton .

The aryl group, fluorenyl group, heterocyclic group and fused ring group of R ¹ , R ² and Ar ¹ , and the alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group of R ¹ and R ² are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C ₁ ~ C ₂₀ of the import alkylthio; C ₁ -C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; A C ₆ -C ₂₀ aryl group unsubstituted or substituted with a C ₂ -C ₂₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P; C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A heterocyclic group substituted with a C ₆ ~ C ₂₀ aryl unit or is unsubstituted, O, N, S, Si and C ₂ ~ containing at least one hetero atom in the P C _20; C ₃ -C ₂₀ cycloalkyl group; It may be substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group.

Preferably, Ar ¹ of Formula 1 may be one of those represented by A1 to A52 of Formula 2 below.

[Formula 2]

In A1-A52, a is an integer of 0-5, b is an integer of 0-7, c is an integer of 0-9, d is an integer of 0-6, e is an integer of 0-5, f is 0- An integer of 8, g is an integer of 0-4, h is an integer of 0-3, i is an integer of 0-2, j is an integer of 0 or 1.

In addition, when a to j is 2 or more, a plurality of R ³ are the same as or different from each other, and independently from each other deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; And C ₆ ~ C ₃₀ An aryloxy group; may be selected from one or more groups.

In addition, Q ¹ is N (R ⁴ ), S or O, and Q ² is N (R ⁴ ), C (R ⁵ ) (R ⁶ ), S or O. R ⁴ and R ⁵ are each independently, a C ₆ ~ C ₆₀ An aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And fluorenyl group; It is selected from the group consisting of, R ⁵ and R ⁶ Also C ₆ ~ C ₆₀ An aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And a fluorenyl group; or R ⁵ and R ⁶ may be bonded to each other to form a spiro compound together with the atom C to which they are bonded.

Specifically, the compound represented by the formula may be one of the compounds of the formula (3).

[Formula 3]

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

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

In this case, the organic electric element includes a first electrode; Second electrode; And an organic material layer positioned between the first electrode and the second electrode. The organic material layer may include a compound represented by Chemical Formula 1, and Chemical Formula 1 may be included in the electron transport layer of the organic material layer. That is, the compound represented by Formula 1 may be used as the electron transport layer material. Specifically, it provides an organic electroluminescent device comprising one of the compounds represented by Formula 2 and Formula 3 in the organic material layer, and more specifically, the present invention is an organic electroluminescent device comprising a compound represented by the individual formula in the organic material layer To provide.

In another embodiment of the present invention, the present invention may include at least a light emitting auxiliary layer in the organic material layer.

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

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

In still another embodiment of the present invention, the present invention provides an organic electroluminescent device is formed by any one of the organic coating layer, spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process and roll-to-roll process do.

In another embodiment of the present invention, the present invention provides a display device including an organic electric element including the organic material layer; And a controller for driving the display device.

In another embodiment of the present invention, the organic electroluminescent device according to the present invention is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a device for monochrome or white illumination It can be one.

Hereinafter, the synthesis examples of the compounds represented by the chemical formulas according to the present invention and the production examples of the organic electric device will be described in detail by way of examples, but the present invention is not limited to the following examples.

Synthesis Example

For example, the compound represented by Chemical Formula 3 according to the present invention (Final Product: P-1 to P-120) may be synthesized by reacting Sub 1 with (Ar ¹ ) _x -L ² -Hal ³ as in Scheme 1 below. Can be.

<Scheme 1>

(R ¹ , R ² , L ¹ , L ² , Ar ¹ , m and n are the same as defined in the above formula, Hal ³ is Br or Cl.)

I. Synthesis of Sub 1

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

<Scheme 2>

In Scheme 2, Hal ¹ is Br or I, and Hal ² is Br or Cl. In Scheme 2, the intermediate Sub 1-III is the same as when L ¹ is a single bond in Sub 1, and the intermediate Sub 1-III as shown in the compound belonging to Sub 1 to produce a compound according to the present invention You can also use

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

TABLE 1

On the other hand, the synthesis examples of specific compounds belonging to Sub 1 are as follows.

1.Synthesis of Sub 1-1 (Sub 1-14)

<Scheme 3>

(1) Sub 1-I-1 Synthesis

The starting material 2-bromobenzoic acid (41.69 g, 207.4 mmol) was dissolved in 2-ethoxyethanol in a round bottom flask, followed by naphthalen-1-amine (31.18 g, 217.8 mmol), Cu (1.19 g, 18.7 mmol), Cu ₂ O (1.19 g, 8.3 mmol), K ₂ C0 ₃ (28.66 g, 207.4 mmol) was added and stirred at 130 ° C. When the reaction was completed, the temperature of the reactant was lowered, and charcoal and water were added and filtered through Celite. The filtrate was added hydrochloric acid (diluted HCl) to form a precipitate. The obtained precipitate was again dissolved in 5% Na ₂ CO ₃ aqueous solution, filtered and dried over Celite to give 51.33 g (yield: 94%) of the product.

(2) Sub 1-II-1 Synthesis

Sub 1-I-1 (51.33 g, 195 mmol) obtained in the above synthesis was added to phosphorus oxychloride (430.45 g, 2807.4 mmol) in a round bottom flask and slowly heated to 85-90 ° C. for 15 minutes. After 30 minutes, the boiling had subsided slightly and refluxed and stirred. After the reaction was completed, excess phosphorus oxychloride was removed by distillation and cooled. The obtained reactant was added to a mixture of chloroform-ammonia (ammonia solution, ice, chloroform), stirred for 1 hour, and then extracted with chloroform and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized from a silica gel column to give 42.67 g (yield: 83%) of product.

(3) Sub 1-III-1 (Sub 1-14) Synthesis

Sub 1-II-1 (42.67 g, 161.8 mmol) obtained in the above synthesis was dissolved in DMF in a round bottom flask, followed by Bis (pinacolato) diboron (45.2 g, 178 mmol), Pd (dppf) Cl ₂ (3.96 g, 4.9 mmol), KOAc (47.64 g, 485.4 mmol) was added and stirred at 90 ° C. After the reaction was completed, DMF was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was purified by silica gel column and 41.38 g (yield: 72%) of the product.

(4) Sub 1-IV-1 Synthesis

Sub 1-III-1 (28.27 g, 79.6 mmol) obtained in the above synthesis was dissolved in THF in a round bottom flask, followed by 1-bromo-4-iodobenzene (33.77 g, 119.4 mmol), Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol), K ₂ C0 ₃ (33 g, 238.7 mmol), water were added and stirred at 80 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resultant compound was purified by silica gel column and recrystallized to give a product 24.16 g (yield: 79%).

(5) Sub 1-1 synthesis

Sub 1-IV-1 (24.16 g, 62.9 mmol) obtained in the above synthesis was dissolved in DMF in a round bottom flask, followed by Bis (pinacolato) diboron (17.56 g, 69.2 mmol), Pd (dppf) Cl ₂ (1.54 g, 1.9 mmol), KOAc (18.51 g, 188.6 mmol) was added and stirred at 90 ° C. After the reaction was completed, DMF was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated and the resulting compound was purified by silica gel column and recrystallized to give 22.78 g (yield: 84%) of product.

2. Synthesis of Sub 1-9

<Scheme 4>

(1) Synthesis of Sub 1-IV-9

Sub 1-III-1 (8.92 g, 25.1 mmol) obtained in the synthesis of 2-bromo-7-iodo-9,9-diphenyl-9 H- fluorene (19.71 g, 37.7 mmol), Pd (PPh ₃ ) ₄ (1.45 g, 1.3 mmol), K ₂ CO ₃ (10.41 g, 75.3 mmol), THF, and water were obtained using the Sub 1-IV-1 synthesis method to obtain 10.82 g (yield: 69%) of the product.

(2) Sub 1-9 synthesis

In Sub 1-IV-9 (10.82 g, 17.3 mmol) obtained in the above synthesis, Bis (pinacolato) diboron (4.84 g, 19.1 mmol), Pd (dppf) Cl ₂ (0.42 g, 0.5 mmol), KOAc (5.1 g, 52 mmol) and DMF were obtained using the Sub 1-1 synthesis to yield 9.31 g (yield: 80%) of product.

3. Synthesis of Sub 1-15

Scheme 5

(1) Sub 1-I-15 Synthesis

In starting material 3-bromo- [1,1'-biphenyl] -4-carboxylic acid (20.56 g, 74.2 mmol), naphthalen-1-amine (11.16 g, 77.9 mmol), Cu (0.42 g, 6.7 mmol) , Cu ₂ O (0.42 g, 3 mmol), K ₂ CO ₃ (10.25 g, 74.2 mmol), and 2-ethoxyethanol were obtained using the above Sub 1-I-1 synthesis to obtain 21.66 g (yield: 86%) of the product. .

(2) Sub 1-II-15 Synthesis

Sub 1-I-15 (21.66 g, 63.8 mmol) obtained in the above synthesis was obtained with phosphorus oxychloride (140.91 g, 919 mmol) using the Sub 1-II-1 synthesis to obtain 16.7 g (yield: 77%) of the product. .

(3) Sub 1-III-15 Synthesis

In Sub 1-II-15 (16.7 g, 49.1 mmol) obtained in the above synthesis, Bis (pinacolato) diboron (13.73 g, 54.1 mmol), Pd (dppf) Cl ₂ (1.2 g, 1.5 mmol), KOAc (14.47 g, 147.4 mmol) and DMF were used to obtain 13.78 g (yield: 65%) of the product using the Sub 1-III-1 synthesis.

(4) Sub 1-IV-15 Synthesis

To Sub 1-III-15 (13.78 g, 31.9 mmol) obtained in the above synthesis, 1-bromo-4-iodobenzene (13.56 g, 47.9 mmol), Pd (PPh ₃ ) ₄ (1.85 g, 1.6 mmol), K ₂ CO ₃ (13.25 g, 95.8 mmol), THF, water was obtained using the Sub 1-IV-1 synthesis method to give 11.18 g (yield: 76%) of the product.

(5) Sub 1-15 synthesis

In Sub 1-IV-15 (11.18 g, 24.3 mmol) obtained in the above synthesis, Bis (pinacolato) diboron (6.78 g, 26.7 mmol), Pd (dppf) Cl ₂ (0.59 g, 0.7 mmol), KOAc (7.15 g, 72.9 mmol), and DMF were used to give the product 10.23 g (yield: 83%) using the Sub 1-1 synthesis method.

4.Synthesis of Sub 1-28

<Scheme 6>

(1) Sub 1-I-28 Synthesis

To starting material 3-bromo- [1,1'-biphenyl] -4-carboxylic acid (24.25 g, 87.5 mmol), 7- (dibenzo [ b , d ] furan-3-yl) naphthalen-1-amine ( 28.43 g, 91.9 mmol), Cu (0.5 g, 7.9 mmol), Cu ₂ O (0.5 g, 3.5 mmol), K ₂ CO ₃ (12.09 g, 87.5 mmol), 2-ethoxyethanol were added to Sub 1-I-1. Synthesis gave 34.95 g (79%) of product.

(2) Sub 1-II-28 Synthesis

Sub 1-I-28 (34.95 g, 69.1 mmol) obtained in the above synthesis was obtained with 21.69 g (yield: 62%) of phosphorus oxychloride (152.64 g, 995.5 mmol) using the Sub 1-II-1 synthesis method. .

(3) Sub 1-28 synthesis

In Sub 1-II-28 (21.69 g, 42.9 mmol) obtained in the above synthesis, Bis (pinacolato) diboron (11.97 g, 47.2 mmol), Pd (dppf) Cl ₂ (1.05 g, 1.3 mmol), KOAc (12.62 g, 128.6 mmol), and DMF were used to give 14.34 g (yield: 56%) of the product using the Sub 1-III-1 synthesis.

II. Product Synthesis

Sub 1 (1 equiv) was dissolved in toluene in a round bottom flask, followed by (Ar ¹ ) _x -L ² -Hal ³ (1.1 equiv), Pd (PPh ₃ ) ₄ ) (0.05 equiv, K ₂ CO ₃ (3 equiv) ) Was added and stirred at 95 ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was subjected to silica gel column and recrystallization to obtain a final product.

1. P-4 Synthesis Example

Scheme 7

Sub 1-1 (4.21 g, 9.8 mmol) obtained in the above synthesis was dissolved in toluene in a round bottom flask, followed by 3,3 '-(5'-chloro- [1,1': 3 ', 1''-terphenyl ] -3,3 ''-diyl) dipyridine (4.5 g, 10.7 mmol), Pd (PPh ₃ ) ₄ (0.56 g, 0.5 mmol), K ₂ CO ₃ (4.05 g, 29.3 mmol), add water and add 95 Stir at ° C. After the reaction was completed, the mixture was extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was purified by silica gel column and recrystallized to give the product 6.04 g (yield: 90%).

2. P-5 Synthesis Example

Scheme 8

Sub 1-1 (4.98 g, 11.5 mmol) obtained in the synthesis of 2-chloro-4,6-diphenylpyrimidine (3.39 g, 12.7 mmol), Pd (PPh ₃ ) ₄ (0.67 g, 0.6 mmol), K ₂ CO ₃ (4.79 g, 34.6 mmol), toluene, and water were obtained using the above P-4 synthesis method to give 5.32 g (yield: 86%) of the product.

3. P-26 Synthesis Example

Scheme 9

To Sub 1-1 (5.06 g, 11.7 mmol) obtained in the above synthesis, 1-bromopyrene (3.63 g, 12.9 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.6 mmol), K ₂ CO ₃ (4.86 g, 35.2 mmol), toluene, and water were obtained using the above P-4 synthesis to give 4.92 g (yield: 83%) of product.

4. P-32 Synthesis Example

Scheme 10

Sub 1-1 (5.27 g, 12.2 mmol) obtained in the synthesis of 2-([1,1'-biphenyl] -3-yl) -4-chloroquinazoline (4.26 g, 13.4 mmol), Pd (PPh ₃ ) ₄ (0.71 g, 0.6 mmol), K ₂ CO ₃ (5.07 g, 36.7 mmol), toluene, water were obtained using the above P-4 synthesis method to give 5.58 g (yield: 78%) of the product.

5. Synthesis Example of P-76

Scheme 11

To Sub 1-14 (2.95 g, 8.3 mmol) obtained in the above synthesis, 5,5 '-(5-chloro-1,3-phenylene) bis (1,2-diphenyl-1 H -indole) (5.91 g, 9.1 mmol), Pd (PPh ₃ ) ₄ (0.48 g, 0.4 mmol), K ₂ CO ₃ (3.44 g, 24.9 mmol), toluene, water 5.93 g (yield: 85%) using the P-4 synthesis Got.

6. Synthesis Example of P-84

Scheme 12

To Sub 1-15 (6.76 g, 13.3 mmol) obtained in the above synthesis, 2-bromobenzo [ d ] thiazole (3.14 g, 14.7 mmol), Pd (PPh ₃ ) ₄ (0.77 g, 0.7 mmol), K ₂ CO ₃ ( 5.52 g, 40 mmol), toluene, and water were used to obtain 5.07 g (yield: 74%) of the product using the above P-4 synthesis.

7. Synthesis Example of P-106

Scheme 13

To Sub 1-9 (8.09 g, 12 mmol) obtained in the above synthesis 4-bromopyridine (2.09 g, 13.2 mmol), Pd (PPh ₃ ) ₄ (0.7 g, 0.6 mmol), K ₂ CO ₃ (4.99 g, 36.1 mmol), toluene and water were obtained using the above P-4 synthesis to give 4.65 g (yield: 62%) of product.

8. P-120 Synthesis Example

Scheme 14

In Sub 1-28 (8.72 g, 14.6 mmol) obtained in the above synthesis, 2-chloropyrido [2,3- d ] pyrimidine (2.66 g, 16.1 mmol), Pd (PPh ₃ ) ₄ (0.84 g, 0.7 mmol), K ₂ CO ₃ (6.05 g, 43.8 mmol), toluene, water was obtained using the P-4 synthesis method to obtain 4.73 g (yield: 54%) of the product.

On the other hand, FD-MS values of the compounds P-1 to P-120 of the present invention prepared according to the synthesis examples as described above are shown in Table 2.

TABLE 2

On the other hand, in the above described exemplary synthetic examples of the present invention represented by the general formula, these are all copper-catalyzed Amination of Bromobenzoic Acids reaction ( J. Org. Chem . 2006, 71, 260.), Cyclization by POCl ₃ reaction ( J. Am. Chem. Soc. , 1946, 68, 1599; Chem Sci Trans ., 2013, 2 , 246), based on the Miyaura boration reaction and Suzuki cross-coupling reaction, etc. Those skilled in the art will readily understand that the reaction proceeds even if other defined substituents (substituents such as R ¹ , R ² , L, Ar ^1, etc.) are combined.

For example, the starting material-> Sub 1-I reaction in Scheme 2 is based on the Copper-Catalyzed Amination of Bromobenzoic Acids reaction, and the Sub 1-I-> Sub 1-II reaction in Scheme 2 is Cyclization by POCl _3. The reaction is based on the reaction, and the reaction of Sub 1-II-> Sub 1-III, Sub 1-IV-> Sub 1 in Scheme 2 is based on Miyaura boration reaction. Sub 1-III-> Sub 1-IV and <Scheme 7> to <Scheme 14> in Scheme 2 are based on the Suzuki cross-coupling reaction. It is clear that the reactions can proceed even if substituents not specifically specified in these are attached.

Manufacturing Evaluation of Organic Electrical Device

Example 1 Green Organic Electroluminescent Device (electron transport layer)

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as an electron transport layer material.

First, 4,4 ', 4''-Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited on an ITO layer (anode) formed on a glass substrate. After the hole injection layer was formed, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as NPD) was vacuum deposited to a thickness of 60 nm on the hole injection layer. Was formed. Next, CBP [4,4'-N, N'-dicarbazole-biphenyl] as a host material on the hole transport layer and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] as a dopant material were 95: A light emitting layer having a thickness of 30 nm was deposited by doping at a weight ratio of 5 nm. Subsequently, (1,1'bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer by hole blocking. A layer was formed, and the electron transport layer was formed by vacuum depositing the compound P-1 of the present invention on the hole blocking layer to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[Example 2] to [Example 120] Green organic electroluminescent device (electron transport layer)

An organic electroluminescent device was manufactured according to the same method as Example 1 except for using the compounds P-2 to P-120 of the present invention shown in Table 3 below instead of the compound P-1 of the present invention as the electron transporting material.

Comparative Example 1

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

<Comparative Compound 1> Alq ₃

Comparative Example 2

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

Comparative Compound 2

Electroluminescence (EL) characteristics by PR-650 of photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices prepared by Examples 1 to 120, Comparative Examples 1 and 2 of the present invention The T95 lifetime was measured using a lifespan measuring instrument manufactured by McScience Inc. at 5000 cd / m ² reference luminance. The measurement results are shown in Table 3 below.

TABLE 3

As can be seen from the results of Table 3, the organic electroluminescent device using the compound of the present invention as the material of the electron transport layer has a driving voltage compared to the organic electroluminescent device using the comparative compound 1 and the comparative compound 2 as the material of the electron transport layer. It was low, and not only the luminous efficiency was improved but also the life and the like markedly improved.

This result shows that the comparative compound 2 shows a significantly lower T ₁ value (2.0 eV) similar to that of the comparative compound 1 of Alq ₃ , whereas the compounds of the present invention show a relatively high T ₁ value (2.1 eV to 2.3 eV). In other words, it is considered that the reason is that the probability of the exciton staying well in the light emitting layer is relatively increased.

Also, when I was the same Ben Joa acridine (benzo [c] acridine) -L more alkyl group (Comparative compound 2) has, even if the core ¹ -L ² -Ar ¹ (compound of the invention), the main (main) substituents, It shows relatively high electron mobility and high thermal stability, and as a result, charge and balance of holes and electrons in the light emitting layer can be achieved to realize the optimum luminous efficiency through efficient recombination.

Taken together, the characteristics described above (high T1 values, fast electron mobility and high thermal stability) suggest that the -L ¹ -L ² -Ar ¹ main substituents in the benzo [ c ] acridine core It can be seen that the band gap, electrical characteristics, and interface characteristics can be greatly changed according to the introduction, which is a major factor in improving the device performance.

In addition, the evaluation results of the above-described device fabrication described the device characteristics from the viewpoint of the electron transport layer, but the materials used as the electron transport layer are generally organic electron, such as the electron injection layer, hole injection layer, hole transport layer, light emitting auxiliary layer, light emitting layer, etc. The organic layer of the device can be used in combination with a single or other material. Therefore, the compounds of the present invention may be used in combination with a single or other materials in addition to the electron transport layer, for example, other organic material layers, for example, an electron injection layer, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe 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 interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority under Patent Application No. 10-2013-0149182, filed in Korea on December 03, 2013, pursuant to Article 119 (a) (35 USC § 119 (a)). All content is incorporated by reference in this patent application. In addition, if this patent application claims priority for the same reason for countries other than the United States, all its contents are incorporated into this patent application by reference.

Claims (10)

1. Compound represented by the following formula.

   

   [In the above formula,

   R ¹ and R ² independently of each other deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; And C ₆ ~ C ₃₀ An aryloxy group; It is selected from the group consisting of m is an integer of 0 to 4, n is an integer of 0 to 6;

   L ¹ and L ² are independently of each other a single bond; C ₆ ~ C ₆₀ aromatic ring; Fluorene; C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C ₆₀ fused ring of an aromatic ring; And C ₂ -C ₆₀ heterocycle including at least one heteroatom of O, N, S, Si, and P, each of which is deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C ₁ ~ C ₂₀ of the import alkylthio; C ₁ -C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₆ -C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; It may be substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group,

   Ar ¹ is a C ₆ ~ C ₆₀ An aryl group; Fluorenyl group; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And a C ₂ -C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P, wherein x is an integer of 1 to 3, provided that L ¹ and L X is an integer of 1 when ² is a single bond,

   The aryl group, fluorenyl group, heterocyclic group and fused ring group of R ¹ , R ² and Ar ¹ , and the alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group of R ¹ and R ² are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C ₁ ~ C ₂₀ of the import alkylthio; C ₁ -C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; A C ₆ -C ₂₀ aryl group unsubstituted or substituted with a C ₂ -C ₂₀ heterocyclic group including at least one heteroatom of O, N, S, Si, and P; C ₆ ~ C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A heterocyclic group substituted with a C ₆ ~ C ₂₀ aryl unit or is unsubstituted, O, N, S, Si and C ₂ ~ containing at least one hetero atom in the P C _20; C ₃ -C ₂₀ cycloalkyl group; It may be substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group.]
2. The method of claim 1,

   Ar ¹ is one of the compounds represented by A1 to A52.

   

   

   

   

   [In the above A1 to A52,

   a is an integer of 0 to 5, b is an integer of 0 to 7, c is an integer of 0 to 9, d is an integer of 0 to 6, e is an integer of 0 to 5, f is an integer of 0 to 8, g is An integer of 0 to 4, h is an integer of 0 to 3, i is an integer of 0 to 2, j is an integer of 0 or 1,

   R ³ is the same as or different from each other when a to j are 2 or more, and independently from each other deuterium; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ -C ₃₀ alkoxyl group; And C ₆ ~ C ₃₀ An aryloxy group; at least one selected from the group consisting of,

   Q ¹ is N (R ⁴ ), S or O, Q ² is N (R ⁴ ), C (R ⁵ ) (R ⁶ ), S or O, and R ⁴ to R ⁶ are each C ₆ to C ₆₀ Aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ ~ C ₃₀ Alkoxy group; And a fluorenyl group; and R ⁵ and R ⁶ may be bonded to each other to form a spiro compound together with the atom C to which they are bonded.]
3. The method of claim 1,

   The compound represented by the formula is one of the following compounds.

   

   

   

   

   
4. A first electrode; Second electrode; And an organic material layer positioned between the first electrode and the second electrode.

   An organic electric device, characterized in that the compound according to claim 1 or 2 is contained in the organic material layer.
5. The method of claim 4, wherein

   The organic material layer includes a light emitting layer and an electron transport layer,

   An organic electric device, characterized in that the compound is contained in at least one of the light emitting layer and the electron transport layer.
6. The method of claim 4, wherein

   The organic material layer further comprises an emission layer, and an emission auxiliary layer formed between the emission layer and the first electrode or the emission layer and the second electrode.
7. The method of claim 4, wherein

   And an optical efficiency improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
8. The method of claim 4, wherein

   The organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process.
9. Claim 4 display device comprising the organic electroluminescent element; And

   And a controller for driving the display device.
10. The method of claim 10,

    The organic electronic device is at least one of an organic electroluminescent device, an organic solar cell, an organic photosensitive member, an organic transistor, and a device for monochrome or white illumination.

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