WO2014058183A1 - Compound for organic electronic device, organic electronic device using same, and electronic apparatus of said organic electronic device - Google Patents

Abstract

The present invention provides a novel compound for an organic electronic device that may improve the light-emitting efficiency, stability and lifespan of the device, an organic electronic device using same, and an electronic apparatus of said organic electronic device.

Description

Compound for organic electric device, organic electric device 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. The organic layer is often made of a multi-layer 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 element 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 and the like according to a function.

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

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

However, simply improving the organic material layer does not maximize the efficiency. This is because a long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

In addition, in order to solve the problem of light emission in the hole transport layer in the organic electroluminescent device, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) is required. It is time to develop the floor.

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, in the case of the material used in the hole transport layer, since it has to have a low HOMO value, most have a low T1 value, which causes the excitons generated in the light emitting layer to pass to the hole transport layer, resulting in charge unbalance in the light emitting layer. This causes light emission at the hole transport layer interface.

When emitting light at the hole transport layer interface, the color purity and efficiency of the organic electric element is reduced and the life is shortened. Therefore, the development of a light emitting auxiliary layer having a high T1 value and a HOMO level between the hole transport layer HOMO energy level and the light emitting layer HOMO energy level is urgently required.

On the other hand, it delays the diffusion of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of shortening the life of the organic electronic device, and stable characteristics, that is, high glass transition even for Joule heating generated when driving the device. There is a need for development of a hole injection layer material having a temperature. In addition, the low glass transition temperature of the hole transport layer material has been reported to have a significant effect on the device life, depending on the characteristics of the uniformity of the surface of the thin film when driving the device. In addition, the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.

In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, materials forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting auxiliary layer material, a light emitting material, an electron transport material, an electron injection material, etc., are stable and efficient. Supported by the material should be preceded, but the development of a stable and efficient organic material layer for an organic electric device has not been made enough, and therefore, the development of a new material is still required.

An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.

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

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

By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and life of the device can be greatly improved.

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".

On the other hand, the terms "halo" or "halogen" as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.

As used herein, the term "alkyl" or "alkyl group" has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.

As used herein, the term "alkenyl" or "alkynyl" has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.

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.

The term "alkoxy group" used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it 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 a monocyclic or polycyclic aromatic, 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.

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 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only single ring but also multiple rings, and adjacent groups may be formed by combining.

As used herein, the terms "heterocycloalkyl", "heterocyclic group" includes one or more heteroatoms, unless otherwise indicated, having from 2 to 60 carbon atoms, including single rings as well as multicycles. Adjacent groups may be formed in combination. In addition, "heterocyclic group" may mean an alicyclic and / or aromatic including a heteroatom.

As used herein, the term “heteroatom” refers to N, O, S, P, and Si unless otherwise indicated.

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 stated, the term "saturated or unsaturated ring" as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.

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

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 alkoxy groups, C ₁ to C ₂₀ alkylamine groups, C ₁ to C ₂₀ alkylthiophene groups, C ₆ to C ₂₀ arylthiophene groups, C ₂ to C ₂₀ alkenyl groups, C ₂ to C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ aryl alkenyl group, silane group, boron Group, germanium group, and C ₅ ~ 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.

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 electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as Preferably, the compound of the present invention may be used as the light emitting layer 150 and / or the light emitting auxiliary layer 151.

Meanwhile, even in the same core, band gaps, electrical characteristics, and interface characteristics may vary depending on which substituents are bonded at which positions. Therefore, the selection of cores and the combination of sub-substituents bound thereto are also very significant. Importantly, long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.

As described above, in order to solve the light emission problem in the hole transport layer in the organic electroluminescent device, it is preferable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each of the light emitting layers R, G, and B, It is time to develop different emission auxiliary layers. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.

Therefore, in the present invention, by forming a light emitting layer or an auxiliary light emitting layer using a compound represented by the formula (1) by optimizing the energy level (level) and T1 value between each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) of the organic material The life and efficiency of the electric device can be improved at the same time.

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 using a variety of polymer materials is less by a solution process or solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition It can be prepared in a number of layers. 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.

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,

The A ring may be an aromatic ring or a heterocycle fused to a pentagram ring containing neighboring N (nitrogen). That is, ring A shares one side with a pentagram ring containing N. In addition, the A ring may be a monocyclic or polycyclic ring. In the case of a polycyclic ring, the ring may be fused to each other, a plurality of rings may be unfused to each other, or a ring in which the fused and non-fused forms are mixed. Herein, the aromatic ring and the hetero ring may have 6 to 60 carbon atoms, and preferably 6 to 14 carbon atoms. That is, A may be benzene, naphthalene, phenanthrene, or the like.

In addition, when A is a hetero ring, it may be a hetero ring having 2 to 60 carbon atoms, for example, thiophene, furan, pyridine, indole, quinoline and the like.

In Formula 1, X is CR'R ", NR ', or S and O, where R' and R" are independently an aryl group of C ₆ ~ C ₆₀ to each other; C ₂ ~ C ₆₀ Heterocyclic group; Or C ₁ -C ₅₀ alkyl group.

In addition, in Formula 1, R ₁

It may be represented as.

L and o are integers of 0 or 1, and l + o may be 1 or more. When l is 0, L means absence (also called direct bond or single bond).

In the above formula, L may be monovalent or divalent depending on the value of o. For example, when o is 0 and l is 1, L may be monovalent, and when o = l = 1, L may be bivalent. Thus L is selected from the group of monovalent substituents consisting of i) a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ monocyclic heterocyclic group and a fluorenyl group, or ii) a C ₆ -C ₆₀ aryl It may be selected from the group of divalent substituents consisting of a ylene group, a divalent heterocyclic group of C ₂ to C ₆₀ and a fluorenylene group.

In the above formula, Y is hydrogen, deuterium, tritium, halogen group, -N (Ar ₃ ) (Ar ₄ ), nitro group, nitrile group, amide group, silane group, C ₁ ~ C ₅₀ alkyl group, C ₆ ~ In the group consisting of C ₆₀ aryl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₆₀ heterocyclic group, and C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ alicyclic ring group Can be selected.

And p of R <_1> is an integer of 1 or more. In this case, p may be determined according to the A ring. For example, when A ring is a benzene ring, p may be an integer of 1 to 4 since the benzene ring may have 4 carbon atoms, and when A ring is naphthyl, 1 to 6 may be used.

In this case, when p is 2 or more, a plurality of R ₁ may be the same as or different from each other. When p is 2 or more, adjacent R ₁ may be bonded to each other to form one or more rings. That is, when p is 2 or more, adjacent R ₁ may be bonded to each other to form a fused form with A ring. Thus, although A ring itself may be a polycyclic ring, even if A ring is a monocyclic ring, substituents R ₁ may be bonded to each other to form a polycyclic ring fused to A ring.

R ₂ to R ₅ may be defined to be the same as R ₁ . That is, they

It may be represented by, wherein L, Y, l, o and the like may be defined the same as defined in R ₁ .

Meanwhile, in Formula 1, m and n may be 0 or 1, respectively, and m + n is preferably 1 or more. That is, at least one of Ar ₁ and Ar ₂ should be present.

Meanwhile, Ar ₁ may have different substituent definitions depending on m and n. For example, when m = 0, Ar _{1 corresponds} to a direct bond (that is, Ar ₁ does not exist), and m = 1 and n = 0. Ar ₁ is a C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₆₀ heterocyclic group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ aliphatic ring It is selected from the group consisting of monovalent substituents such as condensed ring group, C ₁ ~ C ₅₀ Alkyl group and fluorenyl group, when m = n = 1 Ar ₁ is an arylene group of C ₆ ~ C ₆₀ , C ₂ ~ C ₂₀ alkenylene group, C ₂ to C ₆₀ divalent heterocyclic group, C ₆ to C ₆₀ aromatic ring and C ₃ to C ₆₀ alicyclic ring, C ₂ to C ₂₀ alkylene group and flu It may be selected from the group consisting of a divalent substituent, such as an orylene monomer.

In Formula 1, Ar ₂ is not present when n = 0, and when n = 1, Ar ₂ is a halogen group; Cyano group; Nitro group; Nitrile group; Amide group; Silane group; C ₆ ~ C ₆₀ Aryl group; C ₂ -C ₂₀ alkenyl group; C ₂ ~ C ₆₀ Heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; It may be selected from the group of monovalent substituents consisting of a condensed ring group of -N (Ar ₃ ) (Ar ₄ ) and C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ aliphatic ring.

In this case, Ar ₃ and Ar ₄ are independently of each other C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ heterocyclic group, fluorenyl group, C ₁ ~ C ₅₀ Alkyl group and C ₂ ~ C ₂₀ Al It may be selected from the group consisting of a kenyl group, or Ar ₃ and Ar ₄ may combine with each other to form a heterocycle with N.

Meanwhile, the aromatic ring of A, R ₁ to R ₅ , and R ′, R ″ of X, and Ar ₁ to Ar ₄ may be further substituted with other substituents.

Specifically, when the aromatic ring of A, L, Y, Ar ₁ to Ar ₄ , R ′ and R ″ are C ₆ to C ₆₀ aryl groups, and when Y, Ar ₁ and Ar ₂ are condensed ring groups; When C ₆ to C ₆₀ of L and Ar ₁ are an arylene group, these are deuterium; Halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₁ ~ C ₂₀ Alkoxy group; An amine group substituted with a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group; C ₁ ~ C ₂₀ Alkylamine group; C ₁ ~ C ₂₀ alkyl group of the import; C ₆ -C ₂₀ arylthio group; C ₂ -C ₂₀ alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₃ -C ₂₀ cycloalkyl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₈ -C ₂₀ aryl alkenyl group; Silane group; Boron group; Germanium group; And it may be substituted with one or more substituents selected from the group consisting of C ₂ ~ C ₂₀ heterocyclic group.

In addition, the heterocyclic groups of C ₂ to C ₆₀ of A, L, Y, Ar ₁ to Ar ₄ , R ′, and R ″ may include a halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₁ ~ C ₂₀ Alkoxy group; An amine group substituted with a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group; C ₆ ~ C ₆₀ Aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ aryl alkenyl group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of acetylene groups.

In addition, the fluorenyl group of L, Ar ₁ , Ar ₃ and Ar _4, the fluorenylene group of L and Ar ₁ is a deuterium, a halogen group, a C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ Alkoxy group, C ₆ -C ₂₀ aryl group, C ₇ -C ₂₀ arylalkyl group, C ₈ -C ₂₀ arylalkenyl group, C ₁ -C ₅₀ alkyl group, C ₂ -C ₂₀ heterocyclic group, nitrile It may be substituted with one or more substituents selected from the group consisting of a group and an acetylene group.

Further, the alkenyl group of the Y, Ar ₁ to Ar _4, R 'and R "of the C ₁ ~ C ₅₀ alkyl group, and a group of C ₂ ~ C ₂₀ alkylene group of said Ar _1, C ₂ ~ C ₂₀ of; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ aryl alkenyl group; C ₂ -C ₂₀ heterocyclic group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of acetylene groups.

Also, the Y, Ar ₁ to alkenylene group, heavy hydrogen of Ar ₄ of C ₂ ~ C ₂₀ alkenyl group, said Ar ₁ of C ₂ ~ C ₂₀ of; Halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₁ ~ C ₂₀ Alkoxy group; An amine group substituted with a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group; C ₆ ~ C ₆₀ Aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ aryl alkenyl group; C ₃ ~ C ₂₀ Heterocyclic group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of acetylene groups.

On the other hand, Formula 1 may be represented by one of the following formula.

<Formula 2>

<Formula 3>

<Formula 4>

In Formula 1, when A ring is a benzene ring, it may be represented by the above formula (2), and when at least one of R ₂ to R ₅ and the ring A in the formula 1 is -LN (Ar ₃ ) (Ar ₄ ) In Formula 1, when A ring is benzene ring and (Ar ₂ ) m is —N (Ar ₃ ) (Ar ₄ ) in Formula 1, it may be represented by Formula 4.

In Formulas 2 to 4, R ₁₁ to R ₁₄ may be defined as i) R ₁ of Formula 1, or ii) adjacent R ₁₁ and R ₁₂ , adjacent R ₁₂ and R _13, and / or neighbor One R ₁₃ and R _{14 may} combine with each other to form at least one ring. At this time, the adjacent pairs of R ₁₁ to R ₁₄ may be bonded to each other, or only some pairs or only one pair may be bonded to each other to form at least one ring, wherein a group not forming a ring is defined in i) Likewise it can be defined the same as R ₁ .

Meanwhile, in Chemical Formulas 2 to 4, X, Ar ₁ to Ar ₄ , m, n, R ₂ to R ₅ , L may be defined in the same manner as defined in Chemical Formula 1.

For example, in Formula 3, L is a single bond; C ₆ ~ C ₆₀ arylene group; C ₂ ~ C ₆₀ Heterocyclic group; And it may be selected from the group consisting of divalent aliphatic hydrocarbon, Ar ₃ and Ar ₄ are independently of each other i) a C ₆ ~ C ₆₀ aryl group; C ₂ ~ C ₆₀ Heterocyclic group; Fluorenyl groups; An alkyl group of C ₁ to C ₅₀ ; and an alkenyl group of C ₂ to C ₂₀ , or ii) Ar ₃ and Ar ₄ may combine with each other to form a heterocycle with N.

In this case, the arylene group, heterocyclic group, aliphatic hydrocarbon group of L, the aryl group, heterocyclic group, pulluorenyl group, alkyl group and alkenyl group of Ar ₃ and Ar ₄ may be further substituted with a substituent. For example, they may be a deuterium, a halogen group, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group or a C ₂ to C ₂₀ heterocyclic group substituted with an amine group, C ₁ ~ C ₂₀ coming of the alkyl amine group, C ₁ ~ alkyl group of C _20, C ₆ ~ of the C ₂₀ arylthio group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C of ₂₀ cycloalkyl group, C ₆ -C ₆₀ aryl group; One or more substituents selected from the group consisting of C ₆ to C ₂₀ aryl groups, C ₈ to C ₂₀ arylalkenyl groups, silane groups, boron groups, germanium groups, and C ₃ to C ₂₀ heterocyclic groups substituted with deuterium; It may be substituted by.

In addition, the formula represented by Formula 1 may be represented by one of the following formula.

In Formulas 5 to 15, Ar ₁ to Ar ₄ , m, n, X, R ₂ to R ₅ and L are the same as defined in Formula 1.

In addition, Formula 1 may be represented by one of the following formula.

In Formulas 16 to 51, Ar ₁ to Ar ₄ , R ′, R ″, m, n, R ₂ to R ₅ and L are the same as defined in Formula 1.

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

Hereinafter, the synthesis examples of the compounds of the present invention represented by the above formula and the preparation examples of the organic electric device will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

Synthesis Example

By way of example, the compound according to the present invention is prepared by reacting one of Sub 1 or Sub 3 with Sub 2, or by reacting Sub 1 with Sub 4, as in Scheme 1 below.

<Scheme 1>

One. Sub 1 Synthesis Example

<Scheme 2-a>

(One) Example of Sub 1-1-1

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

TABLE 1

(2) Synthesis of Sub 1-1-2

Sub 1-1-1 (1 equiv) was dissolved in anhydrous Ether, the temperature of the reactant was lowered to -78 ° C, n-BuLi (2.5 M in hexane) (1.1 equiv) was slowly added dropwise, and then the reaction was carried out for 30 minutes. Was stirred. Then the temperature of the reaction was lowered to -78 ℃ and Triisopropylborate (1.5 equiv) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the mixture was extracted with ethyl acetate and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain Sub1-1-2.

(3) Synthesis of Sub 1-1-4

Sub 1-1-2 (1 equivalent) obtained in the synthesis was dissolved in THF, and then Sub 1-1-3 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was refluxed with stirring. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 1-1-4.

(4) Sub 1-1 Synthesis

The obtained Sub 1-1-4 (1 equivalent) and triphenylphosphine (2.5 equivalents) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After completion of the reaction, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-1.

Examples of Sub 1-1 are as follows, FD-MS values are shown in Table 2, but is not limited thereto.

TABLE 2

<Scheme 2-b>

(One) Synthesis of Sub 1-2-2

Sub 1-1-2 (1 equivalent) obtained in the synthesis was dissolved in THF, and then Sub 1-2-1 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was refluxed with stirring. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 1-2-2.

(2) Sub 1-2 synthesis

The obtained Sub 1-2-2 and (1 equivalent) and triphenylphosphine (2.5 equivalents) were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction was terminated, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-2.

Examples of Sub 1-2 are as follows, and FD-MS values are shown in Table 3, but are not limited thereto.

TABLE 3

<Scheme 2-c>

(One) Synthesis of Sub 1-3-2

Sub 1-1-2 (1 equivalent) obtained in the synthesis was dissolved in THF, and then Sub 1-3-1 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was stirred under reflux. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product Sub 1-3-2.

(2) Sub 1-3 Synthesis

The obtained Sub 1-3-2 and (1 equivalent) and triphenylphosphine (2.5 equivalents) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-3.

Examples of Sub 1-3 are as follows, and the FD-MS values are shown in Table 4, but are not limited thereto.

TABLE 4

<Scheme 2-d>

(One) Synthesis of Sub 1-4-2

Sub 1-1-2 (1 equivalent) obtained in the synthesis was dissolved in THF, and then Sub 1-4-1 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), NaOH (3 equivalent), and water After addition, the mixture was refluxed with stirring. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain the product Sub 1-4-2.

(2) Synthesis of Sub 1-4

Sub 1-4-2 and (1 equivalent) and triphenylphosphine (2.5 equivalent) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated using column chromatography to obtain the desired Sub 1-4.

Examples of Sub 1-4 are as follows, FD-MS values are shown in Table 5, but is not limited thereto.

TABLE 5

2. Sub 2 Synthesis Example

Examples of Sub 2 are as follows, and FD-MS values are shown in Table 6, but are not limited thereto.

TABLE 6

3. Sub 3 Synthesis Example

Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below.

<Scheme 3>

After Sub 3-1 (1 equiv) was dissolved in THF, Sub 3-2 (1.1 equiv), Pd (PPh ₃ ) ₄ (0.03 equiv), NaOH (3 equiv) and water were added, followed by stirring under reflux. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain product Sub 3.

Examples of Sub 3 are as follows, FD-MS values are shown in Table 7, but is not limited thereto.

TABLE 7

4. Sub 4 Synthesis Example

Examples of Sub 4 are as follows, and FD-MS values are shown in Table 8, but are not limited thereto.

TABLE 8

5. Product Synthesis Example

Sub 1 or Sub 3 (1 equiv) and Sub 2 or Sub 4 (1.1 equiv) are added to toluene and Pd ₂ (dba) ₃ (0.05 equiv), PPh ₃ (0.1 equiv), NaO t -Bu (3 equiv) After each addition, the mixture was stirred under reflux for 24 hours at 100 ° C. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain a final product.

Synthesis Example of 1-9

7,7-dimethyl-7,12-dihydrobenzo [g] indeno [1,2-b] indole (5.7 g, 20 mmol) and 5-bromo-2,4-diphenylpyrimidine (7.5 g, 24 mmol) were added to toluene and Pd ₂ (dba) ₃ (1.0g, 1mmol), PPh ₃ (0.5g, 2mmol) and NaO t -Bu (5.8g, 60mmol) were added, respectively, and the mixture was refluxed at 100 ° C for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 7.2g (70% yield) of the final product.

Synthesis Example of 2-24

12-phenyl-7,12-dihydrobenzo [e] indolo [3,2-b] indole (6.4 g, 20 mmol) and 4-bromo-1,1'-biphenyl (5.6 g, 24 mmol) were added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, respectively, and the mixture was stirred and refluxed at 100 ° C for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 7.2g (74% yield) of the final product.

Synthesis Example of 3-56

14H-dibenzo [e, g] benzo [4,5] thieno [3,2-b] indole (6.5 g, 20 mmol) and 2-bromo-4-phenylquinazoline (6.8 g, 24 mmol) were added to toluene and Pd ₂ ( dba) ₃ (1.0g, 1mmol), PPh ₃ (0.5g, 2mmol), NaO t -Bu (5.8g, 60mmol) were added, and the mixture was stirred under reflux at 100 ° C for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallization to obtain 7.5g (71% yield) of the final product.

Synthesis Example of 4-94

10 H-benzofuro [3,2-b] indole (4.1 g, 20 mmol) and 2- (4-bromophenyl) triphenylene (9.2 g, 24 mmol) were added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added thereto, followed by stirring under reflux at 100 ° C for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 6.6 g (65% yield) of the final product.

Synthesis Example of 1-61

N-([1,1'-biphenyl] -4-yl) -N- (4- (7,7-dimethyl-7,12-dihydrobenzo [g] indeno [1,2-b] indol-9-yl ) phenyl)-[1,1'-biphenyl] -4-amine (13.6 g, 20 mmol) and bromobenzene (3.8 g, 24 mmol) were added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ ( 0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added thereto, followed by stirring under reflux at 100 ° C for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain the final product 11.5g (76% yield).

Synthesis Example of 2-67

N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4 '-(12-phenyl-7,12-dihydrobenzo [e] indolo [3,2-b] indol-9-yl)-[1,1'-biphenyl] -4-yl) -9H-fluoren-2-amine (16.9 g, 20 mmol) and bromobenzene (3.8 g, 24 mmol) were added to toluene and Pd ₂ (dba ) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, and the mixture was stirred under reflux for 24 hours at 100 ° C. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain 13.8g (75% yield) of the final product.

Synthesis Example of 3-85

14H-dibenzo [e, g] benzo [4,5] thieno [3,2-b] indole (6.5 g, 20 mmol) and N-([1,1'-biphenyl] -4-yl) -7-bromo -N- (9,9-diphenyl-9H-fluoren-2-yl) -9,9-dimethyl-9H-fluoren-2-amine (18.2 g, 24 mmol) was added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added, and the mixture was stirred under reflux at 100 ° C. for 24 hours. After extraction with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 12.8 g (64% yield) of the final product.

Synthesis Example of 4-90

10H-benzofuro [3,2-b] indole (4.1 g, 20 mmol) and N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl ] -4-amine (13.3 g, 24 mmol) is added to toluene and Pd ₂ (dba) ₃ (1.0 g, 1 mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) are added, respectively. After stirring, the mixture was refluxed at 100 ° C. for 24 hours. After extracting with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain the final product 9.0g (66% yield).

The FD-MS values of the compounds according to the present invention prepared in the same or similar manner as in the above preparation method are shown in Table 9 below.

TABLE 9

Manufacturing Evaluation of Organic Electrical Device

Experimental Example 1 (light emitting layer)

An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention obtained through synthesis as a light emitting host material of a light emitting layer. First, on the ITO layer (anode) formed on the 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 (abbreviated as 2-TNATA) film was formed by vacuum deposition to a thickness of 60 nm to form a hole injection layer, followed by 4,4-bis [ N- (1-nap) on the hole injection layer. Til) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vacuum deposited to a thickness of 20 nm to form a hole transport layer. In addition, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer by doping at 95: 5 weight using a compound of the present invention as a host material and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] as a dopant material. . 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. A blocking layer was formed and tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.

Comparative Example 1

An organic light emitting display device was manufactured in the same manner as in Experiment 1, except that Comparative Compound 1 (CBP) was used instead of the compound of the present invention as a host material in forming the emission layer.

<Comparative Compound 1>

Comparative Example 2

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except that Comparative Compound 2 was used instead of the compound of the present invention as a host material in forming the emission layer.

<Comparative Compound 2>

The electroluminescent (EL) characteristics of the organic electroluminescent devices prepared by Experimental Example 1, Comparative Example 1 and Comparative Example 2 of the present invention were subjected to a forward bias DC voltage and measured by the photoresearch company PR-650. Is shown in Table 10 below. At this time, the T90 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.

On the other hand, the organic electroluminescent device manufactured according to Experimental Example 1 of the present invention is shown in Table 10 Examples 1 to 269.

TABLE 10

As can be seen from the above results, the organic electroluminescent device using the compound according to the present invention as the light emitting layer material not only significantly improved the luminous efficiency and lifespan, but also the color purity. In particular, the organic light emitting display device according to Examples 134 to 201, where X is S, exhibits low driving voltage, high efficiency, and high lifetime, and has the best results as a phosphorescent host.

In addition, when comparing the device results of Examples (69) to (133) which are the compounds of the present invention, the compound of the present invention having a structure in which a ring is bonded to the core has a higher efficiency than that of Comparative Example 2. It was confirmed that high lifetime was shown.

This can be confirmed that even in the case of applying the same or similar substituents in the case of the polycyclic heterocyclic core as in the present invention and Comparative Example 2 as shown in Table 10 shows a large difference in efficiency and lifespan by the structure of the core core. This is a result showing that the efficiency and life is determined by the band gap of the core, rather than LUMO, HOMO control by the substituent effect. Therefore, the similarity between the substituent effect and the core alone may not easily predict the result shown in Table 10.

Experimental Example 2 (light emitting auxiliary layer)

First, a 2-TNATA film is vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer by forming a hole injection layer, and then a NPD is vacuum deposited on the hole injection layer by 20 nm thickness to form a hole transport layer. Formed. The compound of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer. Subsequently, CBP [4,4'-N, N'-dicarbazole-biphenyl], Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] is used as a dopant as a host on top of the emission auxiliary layer. A 30 nm thick light emitting layer was deposited by doping by weight. Subsequently, 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 deposited to a thickness of 40 nm to form an electron injection layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.

Comparative Example 3

An organic light emitting diode was manufactured in the same manner as in Experiment 2, except that the light emitting auxiliary layer was not formed in Experimental Example 2.

[Comparative Example 4]

An organic light emitting display device was manufactured in the same manner as in Experimental Example 2, except that Comparative Compound 3 was used instead of the compound of the present invention when forming the emission auxiliary layer.

Comparative Compound 3

[Comparative Example 5]

An organic light emitting display device was manufactured in the same manner as in Experimental Example 2, except that Comparative Compound 4 was used instead of the compound of the present invention when forming the emission auxiliary layer.

<Comparative Compound 4>

The electroluminescence (EL) characteristics of the organic electroluminescent devices prepared according to Experimental Example 2 and Comparative Examples 3 to 5 were prepared by applying a forward bias DC voltage to PR-650 of photoresearch. The results are shown in Table 11 below. At this time, the T90 life was measured through the life measurement equipment manufactured by McScience Inc. at 300 cd / m 2 reference luminance.

On the other hand, the organic light emitting device manufactured according to Experimental Example 2 of the present invention is shown in Table 11 to Examples 270 to 385.

TABLE 11

As can be seen from the above results, in the case of the organic electroluminescent device using the compound according to the present invention as a material of the light emitting auxiliary layer, it can be seen that the luminous efficiency and life is improved while the driving voltage is lower than in Comparative Examples 3 to 5. That is, it can be seen that the device characteristics are improved in the case of the organic electric device to which the compound according to the present invention is applied.

In particular, in the case of Examples 328 to 356 where X is S, the driving voltage was remarkably low, and the efficiency and lifespan were remarkably improved. Thus, the device characteristics were excellent.

In addition, comparing the results of the devices of Examples (299) to (327) of Inventive Compounds similar to Comparative Example 4, it was confirmed that the compound of the present invention having a structure in which the core is bonded to the ring exhibits higher efficiency and higher lifetime. It was.

This can be explained as having a high T1 energy level when the compound of the present invention is used as a light emitting auxiliary layer alone, and improving the low voltage, high luminous efficiency, and device life of the organic electroluminescent device due to the deep HOMO energy level. .

Even if the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, the same effect can be obtained.

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.

[Description of the code]

100: organic electric element 110: substrate

120: first electrode 130: hole injection layer

140: hole transport layer 141: buffer layer

150: light emitting layer 151: light emitting auxiliary layer

160: electron transport layer 170: electron injection layer

180: second electrode

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority pursuant to United States Patent Act section 119 (a) (35 USC § 119 (a)) with respect to patent application No. 10-2012-0112838, filed in South Korea on October 11, 2012. 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 (12)

1. Compound represented by one of the following formula.

   <Formula 2>

   

   <Formula 3>

   

   <Formula 4>

   

   [In Formula 2 to Formula 4,

   X is CR′R ″, NR ′, S or O (where R ′ and R ″ are independently of each other an aryl group of C ₆ to C ₆₀ , a heterocyclic group of C ₂ to C ₆₀ or C ₁ to C ₅₀ Is an alkyl group),

   R ₂ to R ₅ is

   

   Displayed,

   R ₁₁ to R ₁₄ are i) hydrogen; heavy hydrogen; or

   

   Or ii) R ₁₁ and R ₁₂ , R ₁₂ and R _13, and / or R ₁₃ and R ₁₄ combine with each other to form at least one ring (wherein X is NR ′, S or If O, R ₁₁ and R ₁₂ , R ₁₂ and R _13, and / or R ₁₃ and R ₁₄ combine with each other to form at least two rings (but do not form a ring among R ₁₁ to R ₁₄₎ . The group is the same as defined in i)),

   l and o are integers of 0 or 1, l + o is 1 or more,

   L is selected from i) a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ monovalent heterocyclic group and a fluorenyl group, or ii) a C ₆ -C ₆₀ arylene group, C ₂ ~ C ₆₀ divalent heterocyclic group and fluorenylene group,

   Y is hydrogen, deuterium, tritium, halogen group, -N (Ar ₃ ) (Ar ₄ ), nitro group, nitrile group, amide group, silane group, C ₁ ~ C ₅₀ alkyl group, C ₆ ~ C ₆₀ aryl Group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₆₀ heterocyclic group, and C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ alicyclic ring group selected from the group consisting of,

   m and n are each 0 or 1, where m + n is 1 or more,

   Ar ₁ is i) C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₆₀ monovalent heterocyclic group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ An aliphatic ring monovalent condensed ring group, a C ₁ to C ₅₀ alkyl group and a fluorenyl group, or ii) a C ₆ to C ₆₀ arylene group, a C ₂ to C ₂₀ alkenylene group, C group ₂ ~ C _2-valent heterocyclic group in _60, C ₆ ~ C ₆₀ of the ring with C ₃ ~ C 2 monovalent condensed ring of an aliphatic ring group of _60, C ₂ ~ C ₂₀ alkylene group, and fluorene-ylene group the group consisting of Is selected from

   Ar ₂ is a halogen group; Cyano group; Nitro group; Nitrile group; Amide group; Silane group; C ₆ ~ C ₆₀ Aryl group; C ₂ -C ₂₀ alkenyl group; C ₂ ~ C ₆₀ Heterocyclic group; C ₁ ~ C ₅₀ Alkyl group; -N (Ar ₃ ) (Ar ₄ ); And it is selected from the group consisting of a condensed ring of C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ Aliphatic ring,

   Ar ₃ and Ar ₄ are each independently a C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ heterocyclic group, fluorenyl group, C ₁ ~ C ₅₀ Alkyl group and C ₂ ~ C ₂₀ Alkenyl group It is selected from the group consisting of.

   (At this time, the C ₆ ~ C ₆₀ aryl group of L, Y, Ar ₁ to Ar ₄ , R 'and R ″, the condensed ring of Y, Ar ₁ and Ar ₂ , and C ₆ of L and Ar ₁ The arylene group of ~ C ₆₀ is substituted with deuterium; halogen group; C ₁ ~ C ₂₀ alkyl group; C ₁ ~ C ₂₀ alkoxy group; C ₆ ~ C ₂₀ aryl group or C ₂ ~ C ₂₀ heterocyclic group amine group; C ₁ ~ alkyl amine group of the C _20; C ₁ ~ alkylthio C _20; C ₆ ~ C ₂₀ coming aryl tea; C ₂ ~ alkenyl group of C _20; C ₂ ~ alkynyl group of C ₂₀ C ₃ ~ C ₂₀ cycloalkyl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₈ ~ C ₂₀ aryl alkenyl group; Silane group; Boron group; Germanium group; and C ₂ ~ C ₂₀ hetero May be substituted with one or more substituents selected from the group consisting of a ring group,

   The heterocyclic group of C ₂ to C ₆₀ of L, Y, Ar ₁ to Ar ₄ , R ′, and R ″ may be a halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₁ ~ C ₂₀ Alkoxy group; An amine group substituted with a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group; C ₆ ~ C ₆₀ Aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ aryl alkenyl group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of acetylene group,

   The fluorenyl group of L, Ar ₁ , Ar _3, and Ar ₄ , and the fluorenylene group of L and Ar _{1 include} a deuterium, a halogen group, an alkenyl group of C ₂ to C _{20, and} an alkoxy group of C ₁ to C ₂₀ . , C ₆ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₁ ~ C ₅₀ alkyl group, C ₂ ~ C ₂₀ heterocyclic group, nitrile group and May be substituted with one or more substituents selected from the group consisting of acetylene groups,

   An alkenyl group of the Y, Ar ₁ to Ar _4, R 'and R "of the C ₁ ~ C ₅₀ alkyl group, and a group of C ₂ ~ C ₂₀ alkylene group of said Ar _1, C ₂ ~ C ₂₀ of; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ aryl alkenyl group; C ₂ -C ₂₀ heterocyclic group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of acetylene group,

   Wherein Y, Ar ₁ to Ar ₄ of C ₂ ~ C ₂₀ alkenyl group, a group of C ₂ ~ C ₂₀ alkenylene group of said Ar _1, heavy hydrogen; Halogen group; C ₁ ~ C ₂₀ Alkyl group; C ₁ ~ C ₂₀ Alkoxy group; An amine group substituted with a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heterocyclic group; C ₆ ~ C ₆₀ Aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₇ -C ₂₀ arylalkyl group; C ₈ -C ₂₀ aryl alkenyl group; C ₃ ~ C ₂₀ Heterocyclic group; Nitrile group; And it may be substituted with one or more substituents selected from the group consisting of acetylene group)]
2. The method of claim 1,

   Compound represented by one of the following formula.

   

   

   

   (In the above formula, Ar ₁ to Ar ₄ , m, n, X, R ₂ to R ₅ and L are the same as defined in claim 1)
3. The method of claim 1,

   Compounds, characterized in that one of the formula.

   

   (In the above formula, Ar ₁ , Ar ₂ , R ′, R ″, m, n and R ₂ to R ₅ are the same as defined in claim 1).
4. The method of claim 1,

   Compound represented by one of the following formula.

   

   

   (Wherein Ar ₁ to Ar ₄ , m, n, R ′, R ″ and L are the same as defined in claim 1)
5. The method of claim 1,

   Compound represented by one of the following formula.

   

   

   (In the above formula, Ar_One, m, R ′, R ″, R₂ To R₅, Ar₃ And Ar₄Is the same as defined in paragraph 1)
6. The method of claim 1,

   Compound which is one of the following compounds.

   

   

   

   

   

   

   

   

   

   

   

   
7. In 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,

   The organic material layer is characterized in that it contains a compound of any one of claims 1 to 6.
8. The method of claim 7, wherein

   And forming the compound into the organic material layer by a soluble process.
9. The method of claim 7, wherein

   The organic material layer comprises at least one of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer and a light emitting auxiliary layer.
10. The method of claim 9,

    The compound is an organic electric device, characterized in that used as the material of the light emitting layer or the material of the light emitting auxiliary layer.
11. A display device comprising the organic electronic device of claim 7; And

    And a controller for driving the display device.
12. The method of claim 11,

    The organic electroluminescent device 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.

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