KR102059957B1 - Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound including an five-membered hetero ring that can improve the luminous efficiency, stability and life of the device, an organic electric device using the same, and an electronic device thereof.

Description

COMPONENT FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A 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.

Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, depending on their functions.

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 lifespan.

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 light emission problem in the hole transport layer in the recent 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) 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, it has a low T1 value because it has to have a low HOMO 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, while delaying the penetration of metal oxides into the organic layer from the anode electrode (ITO), which is one of the causes of the shortening of the life of the organic electric device, stable properties, that is, high glass transition even for Joule heating generated when the device is driven. There is a need for development of a hole injection layer material having a temperature. The low glass transition temperature of the hole transport layer material has a characteristic of lowering the uniformity of the surface of the thin film when the device is driven, which has been reported to have a great effect on device life. In addition, the OLED device is mainly formed by a deposition method, which requires development of a material that can withstand a long time during deposition, that is, a material having strong heat resistance.

That is, in order to fully exhibit the excellent characteristics of the organic electric device, the materials constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc., are stable and efficient. Supported by the material should be preceded, but development of a stable and efficient organic material layer for an organic electric device has not been made yet. Therefore, the development of new materials continues to be required, and in particular, the development of material combinations of the light emitting auxiliary layer and the hole transport layer is urgently 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, the driving voltage of the device can be lowered, and color purity, luminous efficiency and lifetime can be greatly improved.

1 is an exemplary view of an organic electroluminescent device according to an embodiment of 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 specified, but is not limited thereto.

In the present invention, an aryl group or an arylene group means a monocyclic or heterocyclic 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 a single ring but also a heterocycle, and adjacent groups may be formed by bonding.

As used herein, the terms "heterocycloalkyl" and "heterocyclic group" include one or more heteroatoms, unless otherwise indicated, have a carbon number from 2 to 60, and include heterocycles as well as monocycles. 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.

In addition, unless otherwise stated, the term "substituted" in the term "substituted or unsubstituted" is deuterium, halogen, amino group, nitrile group, nitro group, C1-C20 alkyl group, C1-C20 alkoxy group , C1-C20 alkylamine group, C1-C20 alkylthiophene group, C6-C20 arylthiophene group, C2-C20 alkenyl group, C2-C20 alkynyl group, C3-C20 cycloalkyl group, C6- ~ One or more substituents selected from the group consisting of an aryl group of C 60, a C 6 to C 20 aryl group substituted with deuterium, an aryl alkenyl group of C 8 to C 20, a silane group, a boron group, a germanium group, and a heterocyclic group of C 5 to C 20 Substituted with, and are 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. An organic material layer containing a compound represented by the formula (1) between) is provided. 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 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 at least one of the host material, the hole transport layer material and the light emitting auxiliary layer material of the light emitting layer.

On the other hand, even in the same core, the band gap, electrical characteristics, interface characteristics, etc. may vary depending on which substituents are bonded at which positions, so the selection of the cores and the combination of sub-substituents bound thereto are very good. In particular, 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 that a light emitting auxiliary layer be formed between the hole transport layer and the light emitting layer, and the light emitting layer R, G, and B may be formed according to each other. It is time to develop another light emitting auxiliary layer. 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 using the compound represented by the formula (1) as a host material, a hole transport layer material and an auxiliary light emitting layer material of the light emitting layer, the energy level (T1) value and T1 value between each organic material layer (mobility, Interface characteristics, etc.) can be optimized to simultaneously improve the lifespan and efficiency of the organic electronic device.

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 conductive metal oxide or an alloy thereof on the substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer (on the substrate) 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 may be formed by using a variety of polymer materials, but not by a deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. 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 is an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a single color or white

It can be one.

Another embodiment of the present invention may include an electronic device including a display device including the organic electric element of the present invention described above, and 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).

In the above formula, R ₁ to R ₄ ⅰ) at least one of, independently of each other, hydrogen, deuterium, tritium, halogen, C ₆ ~ C ₆₀ aryl group, fluorenyl group, O, N, S, Si and P C ₂ ~ C ₆₀ heterocyclic group containing a hetero atom of, C ₁ ~ C ₅₀ Alkyl group, C ₂ ~ C ₂₀ Alkenyl group, C ₁ ~ C ₃₀ Alkoxyl group and -LN (Ar ₁ ) (Ar ₂ ) or ii) adjacent groups combine with each other to form at least one ring. At this time, the group which does not form a ring is as defined in i).

Here, 'neighboring groups combine with each other to form at least one ring' means that R ₁ and R ₂ , R ₂ and R _3, and / or R ₃ and R ₄ combine with each other and at least one ring. It is meant to form a compound. At this time, since it is important that the adjacent groups are bonded to each other to form a ring, the scope of the present invention is not limited by what substituents and by what reaction the ring is formed. At this time, the ring is a known reaction (Heck reaction or Chem. Eur. J. 2009, 15, 742, Molecules. 2008, 13, 3236-3245, J. Am. Chem. Soc. 2008, 130, 472-480, Tetrahedron Letters. 1997, 38, 4761-4764 and the like).

The ring formed by bonding of adjacent groups among R ₁ to R ₄ may not only be a monocyclic or polycyclic aromatic ring or a hetero ring including at least one hetero atom, but also a fused aromatic ring and an aliphatic ring. For example, neighboring groups of R ₁ and R _{4 may} be bonded to each other to form an aromatic ring such as benzene, naphthalene, phenanthrene, and the like. For example, when R ₁ and R ₂ combine with each other to form a benzene ring, and R ₃ and R ₄ combine with each other to form a benzene ring, a phenanthrene form may be formed together with the benzene ring of the parent nucleus to which they are bonded.

In addition, adjacent groups of R ₁ to R _{4 may} be bonded to each other to form a heterocycle such as thiophene, furan, pyridine, indole, quinoline, and the like, wherein the carbon number may be 2 to 60. In the case of a polycyclic ring, the ring may be fused to each other, a plurality of rings may not be fused to each other, or a ring in which the fused and non-fused forms are mixed.

In the above formula, R ₁₁ , R ₁₂ , R ₂₁ and R ₂₂ are each independently hydrogen, deuterium, tritium, halogen, C ₆ ~ C ₆₀ aryl group, fluorenyl group, O, N, S, Si and C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of P, C ₁ ~ C ₅₀ Alkyl group, C ₂ ~ C ₂₀ Alkenyl group, C ₁ ~ C ₃₀ Alkoxyl group and -LN (Ar ₁ ) (Ar ₂ ).

X ₁ and X ₂ are Independently of each other, NR ', O, S, CR'R "or SiR'R", and a and b are integers of 0 or 1. Since a + b must be an integer greater than or equal to ₁ , at least one of X ₁ and X ₂ must exist. In this case, R 'and R "are independently of each other C ₆ ~ C ₆₀ aryl group, fluorenyl group, O, N, S, Si and hetero ring of C ₂ ~ C ₆₀ containing at least one hetero atom of P Group, a C ₁ to C ₅₀ alkyl group and -LN (Ar ₁ ) (Ar ₂ ).

Y is hydrogen, deuterium, tritium, halogen, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P, C ₁ An alkyl group of ˜C _50, an alkenyl group of C ₂ ˜ C ₂₀ , an alkoxyl group of C ₁ ˜C ₃₀ , and —N (Ar ₁ ) (Ar ₂ ), and n is an integer of 0 or 1. If n = 0, Y is absent.

L is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ Heterocyclic group; A C ₃ -C ₆₀ cycloalkylene group; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And divalent aliphatic hydrocarbon groups, each of which (except for a single bond) is a nitro group, a nitrile group, a halogen group, an alkyl group of C ₁ to C ₂₀ , an aryl group of C ₆ to C ₂₀ , and C ₂ to C with one or more substituents selected from the group consisting of heterocyclic groups of _20, an alkoxy group and an amino group of C ₁ ~ C ₂₀ it can be replaced. Herein, 'L' refers to all of L mentioned in the above substituent definition as well as L shown in the above formula (1).

On the other _{hand, -LN (Ar 1) (Ar} 2), -N (Ar 1) (Ar 2) with Ar ₁ and Ar ₂ are independently from each other, such as, an aryl group, a C ₆ ~ C _60, fluorene group, O, It may be selected from the group consisting of a C ₂ ~ C ₆₀ heterocyclic group, a C ₁ ~ C ₅₀ alkyl group and C ₂ ~ C ₂₀ alkenyl group containing at least one hetero atom of N, S, Si and P. .

When R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , R ', R ", Y, Ar ₁ and Ar ₂ are C ₆ -C ₆₀ aryl groups, each of these is deuterium, halogen, silane group, a boron group, a germanium group, a cyano group, a nitro group, C ₁ ~ C ₂₀ coming of the alkylthio, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of the alkenyl group (alkenyl), C ₂ ~ alkynyl group (alkynyl) of C _20, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₂ ~ C ₂₀ heterocyclic group, C of ₃ to C ₂₀ cycloalkyl group, C ₇ to C ₂₀ May be substituted with one or more substituents selected from the group consisting of an arylalkyl group and an arylalkenyl group of C ₈ to C ₂₀ ,

Wherein R ₁ to _{R 4, R 11, R 12} , R 21, R 22, R ', R ", Y, if Ar ₁ and Ar ₂ are C ₂ ~ heterocycle of C _60, each of which is heavy hydrogen, a halogen , Silane group, cyano group, nitro group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₆ ~ C ₂₀ aryl group, deuterium A substituted C ₆ -C ₂₀ aryl group, C ₂ -C ₂₀ heterocyclic group, C ₃ -C ₂₀ cycloalkyl group, C ₇ -C ₂₀ May be substituted with one or more substituents selected from the group consisting of an arylalkyl group and an arylalkenyl group of C ₈ to C ₂₀ ,

When R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , R ', R ″, Y, Ar _1, and Ar ₂ are C ₁ to C ₅₀ alkyl groups, each of them is halogen or silane group. , Boron group, cyano group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₆ ~ C ₂₀ aryl group, deuterium substituted C ₆ to C ₂₀ aryl group, C ₂ to C ₂₀ heterocyclic group, C ₇ to C ₂₀ May be substituted with one or more substituents selected from the group consisting of an arylalkyl group and an arylalkenyl group of C ₈ to C ₂₀ ,

When R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , Y, Ar _1, and Ar ₂ are C ₂ to C ₂₀ alkenyl groups, each of them is a deuterium, a halogen, a silane group, a cyano group , C ₁ ~ C ₂₀ Alkoxy group, C ₁ ~ C ₂₀ Alkyl group, C ₂ ~ C ₂₀ Alkenyl group, C ₆ ~ C ₂₀ Aryl group, C ₆ ~ C ₂₀ aryl substituted with deuterium Group, C ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ May be substituted with one or more substituents selected from the group consisting of an arylalkyl group and an arylalkenyl group of C ₈ to C ₂₀ ,

When R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ and Y are C ₁ to C ₃₀ alkoxy groups, each of these is deuterium, halogen, silane group, C ₁ to C ₂₀ alkyl group, C optionally substituted with one or more substituents selected from the group consisting of ₆ ~ C ₂₀ aryl group, a cycloalkyl group of C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ heterocyclic group and C ₃ ~ C ₂₀ substituted by deuterium Can,

When R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , X ₁ , X ₂ , Ar _1, and Ar ₂ are fluorenyl groups, each of them is deuterium, halogen, silane group, cyano group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of alkenyl groups _{(alkenyl), C 6 ~ C} 20 aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₂ ~ heterocycle of the C ₂₀ And one or more substituents selected from the group consisting of C ₃ to C ₂₀ cycloalkyl groups.

On the other hand, the compound represented by Formula 1 may be represented by one of the following formula. For example, when a = 1 and b = 0, it may be represented by the following Formula 2, and when a = 0 and b = 1, it may be represented by the following Formula 3.

         <Formula 2> <Formula 3>

In addition, the compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulas when adjacent groups of R ₁ to R ₄ combine with each other to form a ring.

          <Formula 4> <Formula 5>

,

,

         <Formula 6> <Formula 7>

        <Formula 8> <Formula 9>

In the above formula, R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , X ₁ , X ₂ , Y, n and L and the like are as defined in formula (1).

In addition, the compound represented by Chemical Formula 1 is represented by the following Chemical Formulas 10 and 11 when Y is a heterocycle, and when n = 1 and Y is -N (Ar ₁ ) (Ar ₂ ) by the following Chemical Formulas 12 and 13, R ₁ When one of ˜R ₄ is —LN (Ar ₁ ) (Ar ₂ ) and the other is hydrogen, it may be represented by the following Formulas 14 and 15.

        <Formula 10> <Formula 11>

         <Formula 12> <Formula 13>

        <Formula 14> <Formula 15>

In the above formula, R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , X ₁ , X ₂ , L, Y, n, Ar ₁ and Ar ₂ and the like are as defined in formula 1, 10 and 11 Ar ₃ is C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₂₀ alkenyl group, O, N, S, Si and P of the at least one heteroatom heteroaryl of C ₂ ~ C ₆₀ containing And a ring group, a C ₁ to C ₅₀ alkyl group and a fluorenyl group, and Z ₁ to Z ₄ are each independently CR ₃₁ or N. In this case, R ₃₁ is hydrogen, deuterium, halogen, silane group, cyano group, nitro group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C of ₆ ~ C ₂₀ aryl group, fluorenyl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ of the Arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group.

In addition, in Formula 2, when X ₁ is NR ', and R' is -LN (Ar ₁ ) (Ar ₂ ), in Formula 16, X ₁ is NR 'in Formula 3, and R' is -LN (Ar ₁ ) (Ar ₂ ) may be represented by the following Formula 17.

           <Formula 16> <Formula 17>

More specifically, the formula represented by Formula 1 may be one of the following compounds.

Hereinafter, the synthesis examples of the compound represented by the formula (1) and the production examples of the organic electric device according to the present invention 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 according to the present invention may be prepared by Synthesis Example 1 or 2 below, and when neighboring groups of R ₁ to R ₄ combine with each other to form a ring, Synthesis Example 3 or 4 below Could be. At this time, the ring is known in other reactions (Chem. Eur. J. 2009, 15, 742, Molecules. 2008, 13, 3236-3245, J. Am. Chem. Soc. 2008, 130, 472-480, Tetrahedron Letters. Reactions described in 1997, 38, 4761-4764, etc.). In the following Synthesis Examples and Schemes, R ₁ corresponds to R ₁ to R ₄ of Formula 1, and R ₂ and R ₃ correspond to R ₁₁ and R ₁₂ of Formula 1.

Synthesis Example 1

Synthesis Example 2

Synthesis Example 3

Synthesis Example 4

As can be seen in the above synthesis examples, the compounds of the present invention can be prepared using known reaction mechanisms such as boration, Suzuki coupling, Hartwig-Buchwald coupling, Heck reaction and the like.

More specifically, the compounds according to the present invention (final products) Sub 1, Sub 2, Sub 6, Sub 7, Sub 8, Sub 9, Sub 10 or Sub 11, Sub 3, Sub 4 or Sub, as shown in the following scheme It can be prepared by reacting with 5.

<Scheme 1>

One. Sub  1 of Synthesis Example

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.

<Scheme 2>

(One) Sub  1-2 synthetic

Sub 1-1 was dissolved in anhydrous THF, the temperature of the reaction was lowered to −78 ° C., n-BuLi (2.5 M in hexane) was slowly added dropwise, and the reaction was stirred at 0 ° C. for 1 hour. Then, the temperature of the reaction was lowered to -78 ℃, trimethyl borate was added dropwise, and stirred at room temperature for 12 hours. After the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. After removal of water in the reaction with anhydrous MgSO ₄ and filtration under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to obtain the desired Sub 1-2.

(2) Sub  1-3 synthetic

The obtained Sub 1-2 (1 equivalent), 1-bromo-2-nitrobenzene (1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), and K ₂ CO ₃ (3 equivalent) substituted with R ₂ were dried with anhydrous THF. After dissolving in a small amount of water, it was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain desired Sub 1-3.

(3) Sub  1 synthetic

Sub 1-3 (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 by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 1.

An example of Sub 1 is as follows, but is not limited thereto. The FD-MS values for the exemplary compounds of Sub 1 below are shown in Table 1.

TABLE 1

2. Sub  2 of Synthesis Example

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below.

<Scheme 3>

(One) Sub  2-2 Synthesis

Sub 2-1 was dissolved in anhydrous THF, the temperature of the reaction was lowered to -78 ° C, n-BuLi (2.5 M in hexane) was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reaction was lowered to -78 ℃, trimethyl borate was added dropwise, and stirred at room temperature for 12 hours. After the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. After removal of water in the reaction product with anhydrous MgSO ₄ and filtration under reduced pressure, the product produced by concentration of the organic solvent was separated by column chromatography to give the desired Sub 2-2.

(2) Sub  2-3 synthetic

The obtained Sub 2-2 (1 equivalent), 1-bromo-2-nitrobenzene (1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), and K ₂ CO ₃ (3 equivalent) substituted with R ₂ were combined with anhydrous THF. After dissolving in a small amount of water, it was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the resulting product was concentrated using an organic solvent. The product was separated using column chromatography to obtain the desired Sub 2-3.

(3) Sub  2 synthesis

The obtained Sub 2-3 (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 by distillation under reduced pressure, and then the concentrated product was separated using column chromatography to obtain the desired Sub 2.

An example of Sub 2 is as follows, but is not limited thereto. The FD-MS values for the exemplary compounds of Sub 2 below are shown in Table 2.

TABLE 2

3. Sub  3 of Synthesis Example

An example of Sub 3 is as follows, but is not limited thereto. FD-MS values for the exemplary compounds of Sub 3 are shown in Table 3.

TABLE 3

4. Sub  4 of Synthesis Example

An example of Sub 4 is as follows, but is not limited thereto. FD-MS values for the exemplary compounds of Sub 4 are shown in Table 4.

TABLE 4

5. Sub  5 of Synthesis Example

Sub 5 of Scheme 1 may be synthesized by the reaction route of Scheme 4 below.

<Scheme 4>

(One) Sub  5-3 Synthesis

Sub 5-1 (1 equiv) and Sub 5-2 (1.1 equiv) are added to toluene and Pd ₂ (dba) ₃ (0.05 equiv), PPh ₃ (0.1 equiv) and NaO t -Bu (3 equiv) were then added, 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 silicagel column and recrystallized to obtain Sub 5-3.

(2) Sub  5, Synthesis

Sub 5-3 (1 equiv) and Sub 5-4 (1.1 equiv) were added to toluene and Pd ₂ (dba) ₃ (0.05 equiv), PPh ₃ (0.1 equiv) and NaO t -Bu (3 equiv) were then added, 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 silicagel column and recrystallized to obtain Sub 5.

An example of Sub 5 is as follows, but is not limited thereto. FD-MS values for the exemplary compounds of Sub 5 are shown in Table 5.

TABLE 5

6. Sub  6 of Synthesis Example

Sub 5 of Scheme 5 may be synthesized by the reaction route of Scheme 4 below.

Scheme 5

(One) Sub  Synthesis of 6-1

Sub 1-3 (1 equiv) and Sub 4 (1.1 equiv) were added to toluene and Pd ₂ (dba) ₃ (0.05 equiv), PPh ₃ (0.1 equiv) and NaO t -Bu (3 equiv) respectively 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 silicagel column and recrystallized to obtain Sub 6-1.

(2) Sub  6 synthetic

The obtained Sub 6-1 (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 by distillation under reduced pressure, and then the concentrated product was separated using column chromatography to obtain the desired Sub 6.

An example of Sub 6 is as follows, but is not limited thereto. FD-MS values for the exemplary compounds of Sub 6 are shown in Table 6.

TABLE 6

7. Sub  7's Synthesis Example

Sub 5 of Scheme 6 may be synthesized by the reaction route of Scheme 4 below.

<Scheme 6>

(One) Sub  Synthesis of 7-1

Sub 2-3 (1 equiv) and Sub 4 (1.1 equiv) were added to toluene and Pd ₂ (dba) ₃ (0.05 equiv), PPh ₃ (0.1 equiv) and NaO t -Bu (3 equiv) 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 silicagel column and recrystallized to obtain Sub 7-1.

(2) Sub  7 synthetic

The obtained Sub 7-1 (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 by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 7.

Examples of Sub 7 are as follows, but are not limited thereto. FD-MS values for the exemplary compounds of Sub 7 are shown in Table 7.

TABLE 7

8. Sub  8's Synthesis Example

Sub 8 of Scheme 7 may be synthesized by the reaction route of Scheme 4 below.

Scheme 7

(One) Sub  8-1 Synthesis

Sub 1-2 with (1 equiv) 1-bromo-2-nitronaphthalene (1 equiv), Pd (PPh ₃ ) ₄ (0.03 equiv), K ₂ CO ₃ (3 equiv) was dissolved in anhydrous THF and a small amount of water and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and then the organic solvent was concentrated, and the resulting product was separated using column chromatography to obtain the desired Sub 8-1.

(2) Sub  8 Synthesis

Sub 3-2 (1 equivalent) and triphenylphosphine (2.5 equivalent) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 8.

An example of Sub 8 is as follows, but is not limited thereto. FD-MS values for the exemplary compounds of Sub 8 are shown in Table 8.

TABLE 8

9. Sub  9, synthesis

Sub 9 of Scheme 1 may be synthesized by the reaction route of Scheme 8 below.

Scheme 8

(One) Sub  9-1 Synthesis

Sub 2-2 and (1 equivalent) 1-bromo-2-nitronaphthalene (1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), K ₂ CO ₃ (3 equiv) was dissolved in anhydrous THF and a small amount of water and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated using column chromatography to obtain the desired Sub 9-1.

(2) Sub  9 synthetic

Sub 9-1 (1 equivalent) and triphenylphosphine (2.5 equivalent) were dissolved in o-dichlorobenzene and refluxed for 24 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 8.

Examples of Sub 9 are as follows, but are not limited thereto. FD-MS values for the exemplary compounds of Sub 9 are shown in Table 9.

TABLE 9

10. Sub  10 Synthesis Example

Sub 10 of Scheme 1 may be synthesized by the reaction pathway of Scheme 9 below.

Scheme 9

(One) Sub  10-1 synthesis

Sub 1-2 with (1 equiv) 9-bromo-10-nitrophenanthrene (1 equiv), Pd (PPh ₃ ) ₄ (0.03 equiv), K ₂ CO ₃ (3 equiv) was dissolved in anhydrous THF and a small amount of water and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated using column chromatography to obtain the desired Sub 10-1.

(2) Sub  10 synthetic

Sub 10-1 (1 equivalent) and triphenylphosphine (2.5 equivalent) were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction was complete, the solvent was removed by distillation under reduced pressure, and then the concentrated product was separated using column chromatography to obtain the desired Sub 10.

Examples of Sub 10 are as follows, but are not limited thereto. FD-MS values for the exemplary compounds of Sub 10 are shown in Table 10.

TABLE 10

11. Sub  Of 11 Synthesis Example

Sub 11 of Scheme 1 may be synthesized by the reaction pathway of Scheme 10 below.

Scheme 10

(One) Sub  11-1 Synthesis

Sub 2-2 with (1 equivalent) 9-bromo-10-nitrophenanthrene (1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), K ₂ CO ₃ (3 equiv) was dissolved in anhydrous THF and a small amount of water and then refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated using column chromatography to obtain the desired Sub 11-1.

(2) Sub  11 Synthesis

Sub 11-1 (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 by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 11.

Examples of Sub 11 are as follows, but are not limited thereto. FD-MS values for the exemplary compounds of Sub 11 are shown in Table 11.

TABLE 11

Products Synthesis of

Sub 1 or Sub 2 or Sub 6 or Sub 7 or Sub 8 or Sub 9 or Sub 10 or Sub 11 (1 equiv) and Sub 3 or Sub 4 or Sub 5 (1.1 equiv) are added to toluene and Pd ₂ (dba) ₃ (0.05 equiv), PPh ₃ (0.1 equiv) and NaO t -Bu (3 equiv) were then added, 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 silicagel column and recrystallized to obtain products.

(1) Synthesis Example of 1-20

1-phenyl-1,5-dihydropyrrolo [3,2-b] carbazole (5.7 g, 20 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (9.3 g, 24 mmol) ) In toluene, 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 silicagel column and recrystallized to obtain the final product 7.9g (68% yield).

(2) Synthesis Example of 1-3

6-phenyl-9H-thieno [2,3-b] carbazole (6.0 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 respectively, followed by stirring 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 the final product 5.1g (66% yield).

(3) Synthesis Example of 2-15

1-([1,1'-biphenyl] -4-yl) -1,5-dihydropyrrolo [3,2-b] carbazole (7.2 g, 20 mmol) and 2- (4-bromophenyl) -4-phenylquinazoline (8.7 g, 24 mmol) in toluene, 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, followed by stirring 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 8.7 g (69% yield) of the final product.

(4) Synthesis Example of 2-3

9H-furo [2,3-b] carbazole (4.1 g, 20 mmol) and 2-bromo-4-phenylquinazoline (6.8 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 respectively, followed by stirring 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 purified by silicagel column and recrystallized to obtain 5.2g (yield 63%) of the final product.

(5) Synthesis Example of 3-66

1-([1,1'-biphenyl] -4-yl) -1,5-dihydropyrrolo [3,2-b] carbazole (7.2 g, 20 mmol) and N-([1,1'-biphenyl] -4 -yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -4-amine (11.4 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 respectively, followed by stirring 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 the final product 10.5g (yield 70%).

(6) Synthesis Example of 3-16

9H-thieno [2,3-b] carbazole (4.5 g, 20 mmol) and N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N- (naphthalen-1-yl)- 9,9-diphenyl-9H-fluoren-2-amine (16.6 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 respectively, followed by stirring 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 purified by silicagel column and recrystallized to obtain 11.3 g (67% yield) of the final product.

(7) Synthesis Example of 4-95

1,5-diphenyl-8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,5-dihydropyrrolo [3,2-b] carbazole (9.7 g, 20 mmol ) In THF, then N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -4-amine (11.4 g, 24 mmol) , Pd (PPh ₃ ) ₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol) and water were added, followed by stirring 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 material was purified by silicagel column and recrystallized to obtain a final product of 9.7g (65% yield).

(8) Synthesis Example of 4-68

1,9-diphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,9-dihydropyrrolo [2,3-b] carbazole (9.7 g, 20 mmol ) In THF, then N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -9,9- Dimethyl-9H-fluoren-2-amine (14.2 g, 24 mmol), Pd (PPh ₃ ) ₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), 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 material was purified by silicagel column and recrystallized to obtain 11.3 g (66% yield) of the final product.

(9) Synthesis Example of 5-115

5-phenyl-1,5-dihydropyrrolo [3,2-b] carbazole (5.6 g, 20 mmol) and N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [ 1,1'-biphenyl] -4-amine (13.3 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 respectively, followed by stirring 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 the final product 10.3g (68% yield).

(10) Synthesis Example of 5-28

9-phenyl-1,9-dihydropyrrolo [2,3-b] carbazole (5.6 g, 20 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9 , 9-dimethyl-9H-fluoren-2-amine (12.4g, 24mmol) was added to toluene and Pd ₂ (dba) ₃ (1.0g, 1mmol), PPh ₃ (0.5 g, 2 mmol) and NaO t -Bu (5.8 g, 60 mmol) were added respectively, followed by stirring 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 9.1g (64% yield) of the final product.

(11) Synthesis Example of 8-9

7H-benzo [g] thieno [3,2-b] carbazole (5.5g, 20mmol), substituted pyridine compound (7.5g, 24mmol), Pd ₂ (dba) ₃ (0.06 ~ 0.1mmol) in a round bottom flask, PPh ₃ (0.2 equiv), NaO t -Bu (6 equiv) and toluene (10.5 mL / 1 mmol) were added and the reaction was carried out at 100 ° C. 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 7.4 g (yield: 67%) of the final product.

(12) Example 9-13 Synthesis

9H-dibenzo [a, c] thieno [2,3-h] carbazole (6.5g, 20mmol), 5-bromo-2,4-diphenylpyrimidine (7.5g, 24mmol), Pd ₂ (dba) _{3 in} a round bottom flask (0.06 ~ 0.1 mmol), PPh ₃ (0.2 equiv), NaO t -Bu (6 equiv) and toluene (10.5 mL / 1 mmol) were added and the reaction was carried out at 100 ° C. 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 final product 7.0g (yield: 65%).

(13) 10-21 Synthesis Example

9- (pyridin-2-yl) -7,9-dihydrobenzo [g] pyrrolo [2,3-b] carbazole (6.7g, 20mmol), bromobenzene (3.8g, 24mmol), Pd ₂ (dba) ) ₃ (0.06 ~ 0.1 mmol), PPh ₃ (0.2 equiv), NaO t -Bu (6 equiv) and toluene (10.5 mL / 1 mmol) were added and the reaction was carried out at 100 ° C. 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 6.2g (yield: 55%) of the final product.

(14) 11-8 Synthesis Example

9H-dibenzo [a, c] thieno [3,2-h] carbazole (6.5g, 20mmol), 4-bromobiphenyl (5.6g, 24mmol), Pd ₂ (dba) ₃ (0.06 ~ 0.1 mmol) in a round bottom flask , PPh ₃ (0.2 equiv), NaO t -Bu (6 equiv) and toluene (10.5 mL / 1 mmol) were added and the reaction was carried out at 100 ° C. 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 material was purified by silicagel column and recrystallization to obtain 6.3 g (yield: 67%) of the final product.

The FD-MS values of the final compound obtained by the above scheme are shown in Table 12.

TABLE 12

Manufacturing Evaluation of Organic Electrical Device

[ Experimental Example  1] Fabrication and test of green organic light emitting device (phosphorescent host)

An organic light emitting diode was manufactured according to a conventional method using the compound of the present invention (1-1 to 1-34) obtained through synthesis as a light emitting host material.

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 (hereinafter abbreviated as 2-TNATA) membrane was vacuum deposited to form a hole injection layer having a thickness of 60 nm. Subsequently, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (abbreviated as -NPD) is vacuum deposited to a thickness of 20 nm on the hole injection layer to form a hole transport layer. It was. Next, a light emitting layer having a thickness of 30 nm was deposited by doping at 95: 5 weight using the compound of the present invention as a host material and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] as a dopant material on the hole transport layer. It was. And (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) on the light emitting layer by vacuum deposition to a thickness of 10 nm A layer was formed, and tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm to form an electron transport layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm 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 light emitting device.

Comparative Example 1

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

<Comparative Compound 1>

Comparative Example 2

An organic light emitting display device was manufactured in the same manner as in Experiment 1, except that Comparative Compound 2 was used as a light emitting layer host material instead of the compound of the present invention.

<Comparative Compound 2>

Comparative Example 3

An organic light emitting display device was manufactured in the same manner as in Experiment 1, except that Comparative Compound 3 was used as a light emitting layer host material instead of the compound of the present invention.

Comparative Compound 3

The electroluminescent (EL) characteristics of the organic light emitting diodes prepared by Experimental Example 1 and Comparative Examples were measured by applying a positive bias DC voltage to the photoresearch company PR-650. . At this time, the life was measured T90 life through the life measurement equipment manufactured by McScience Inc. at 300 cd / m ² reference luminance.

As can be seen from the results of Table 13, the organic electroluminescent device using the organic electroluminescent device material of the present invention has significantly improved luminous efficiency, lifetime, color purity and the like compared to the comparative example. In particular, when comparing the results of the electrical properties when using Comparative Compound 2, Comparative Compound 3 and the compounds of the present invention (1-1 to 34, 6-1 to 11-24), the structure is not bonded to the core ( It can be seen that the luminous efficiency and lifespan of the device to which the compound of the present invention to which the pentagonal ring containing a hetero atom is bonded are significantly improved compared to the structure of Comparative Compound 2) or the benzene ring bonded to the core (Comparative Compound 3). .

[ Experimental Example  2] Red  Fabrication and test of organic light emitting device (phosphorescent host)

An organic light emitting diode was manufactured according to a conventional method using the compound (2-1 to 2-20) of the present invention obtained through synthesis as a light emitting host material. First, a 2-TNATA film is vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, and then a NPD is vacuum-deposited at a thickness of 20 nm on the hole injection layer to form a hole transport layer. It was. Subsequently, the compound of the present invention is doped in a weight ratio of 95: 5 by using a compound of the present invention as a light emitting host material and (piq) ₂ Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] as a dopant material. By depositing a light emitting layer to a thickness of 30nm. Thereafter, BAlq was vacuum deposited to a thickness of 10 nm to form a holdoff layer, and Alq ₃ was formed to a thickness of 40 nm to form a hole transport layer. Subsequently, LiF, which is a halogenated alkali metal, was deposited to a thickness of 0.2 nm on the hole transport layer to form a hole injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting display device.

[Comparative Example 4]

An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that Comparative Compound 1 was used as a light emitting layer host material instead of the compound of the present invention.

[Comparative Example 5]

An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that Comparative Compound 2 was used as a light emitting layer host material instead of the compound of the present invention.

Comparative Example 6

An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that Comparative Compound 3 was used as a light emitting layer host material instead of the compound of the present invention.

The electroluminescent (EL) characteristics of the organic light emitting diodes prepared by Experimental Example 2 and Comparative Examples were measured by applying a positive bias DC voltage to the photoresearch company PR-650. . At this time, the life was measured T90 life through the life measurement equipment manufactured by McScience Inc. at 300 cd / m ² reference luminance.

As can be seen from the results of Table 14, when the compound of the present invention is used as a red light emitting layer material, it is possible to remarkably improve the luminous efficiency, lifetime and color purity of the organic electric device. In particular, when comparing Comparative Compound 2, Comparative Compound 3 and the compound of the present invention, the core is less than the structure in which the ring is not bonded to the core (Comparative Compound 2) or the structure in which the benzene ring is bonded to the Core (Comparative Compound 3). It was confirmed that the efficiency and lifespan of the device to which the compound of the present invention to which the pentagonal ring containing a hetero atom is bonded and the quinazoline derivatives are connected is significantly improved.

[ Experimental Example  3] green organic light emitting element ( Hole transport layer )

An organic light emitting diode was manufactured according to a conventional method using the compound (3-1 to 5-120) of the present invention obtained through synthesis as a hole transport layer material. First, a 2-TNATA film was vacuum deposited on an ITO layer (anode) formed on an organic substrate to form a hole injection layer having a thickness of 60 nm, and then a compound of the present invention was vacuum deposited to a thickness of 20 nm to form a hole transport layer. Next, CBP [4,4'-N, N'-dicarbazole-biphenyl] was used as a host material on the hole transport layer, and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] was used as a dopant material. A light emitting layer of 30 nm thickness was deposited by doping at 10 weights. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm to form a holdoff layer, and Alq ₃ was formed to a thickness of 40 nm to form an electron transport layer. 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 light emitting device.

Comparative Example 7

An organic light emitting display device was manufactured in the same manner as in Experiment 3, except that Comparative Compound 4 was used as a hole transport layer instead of the compound of the present invention.

<Comparative Compound 4>

Comparative Example 8

An organic light emitting display device was manufactured in the same manner as in Experiment 3, except that Comparative Compound 5 was used as a hole transport layer instead of the compound of the present invention.

Comparative Compound 5

Comparative Example 9

An organic light emitting display device was manufactured in the same manner as in Experiment 3, except that Comparative Compound 6 was used as a hole transport layer instead of the compound of the present invention.

Comparative Compound 6

The electroluminescent (EL) characteristics of the organic light emitting diodes prepared by Experimental Example 3 and Comparative Examples were measured by applying a positive bias DC voltage to the photoresearch company PR-650, and the results are shown in Table 15 below. . At this time, the life was measured T90 life through the life measurement equipment manufactured by McScience Inc. at 300 cd / m ² reference luminance.

As can be seen from the results of Table 15, when the compound of the present invention is used as a hole transport layer material, the driving voltage can be lowered, and the luminous efficiency, lifespan, and color purity can be significantly improved compared to the comparative examples. In particular, the compound of the present invention, in which a pentagonal ring containing hetero atoms is bonded to the core, as compared with a compound in which the ring is not bonded to the core as in Comparative Compound 8, or a compound in which the benzene ring is bonded to the core as in Comparative Compound 9 It was confirmed that this exhibits higher efficiency, higher lifetime and lower driving voltage.

[ Experimental Example  4] Green Organic Light Emitting Diode ( Luminous auxiliary 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 auxiliary layer material. First, a 2-TNATA film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60 nm, and NPD was then vacuum-deposited to a thickness of 20 nm on the hole injection layer to form a hole transport layer. . Thereafter, 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. After the emission auxiliary layer was formed, CBP [4,4'-N, N'-dicarbazole-biphenyl] was used as a host material and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] was formed on the emission auxiliary layer. A 30 nm thick light emitting layer was deposited by doping at 95: 5 weight using the dopant material. Subsequently, BAlq was vacuum deposited to a thickness of 10 nm on the light emitting layer to form a holdoff layer, and Alq ₃ was formed to a thickness of 40 nm to form an electron transport layer. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm 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 light emitting device.

Comparative Example 10

An organic light emitting diode was manufactured in the same manner as in Experiment 4, except that the emission auxiliary layer was not formed.

Comparative Example 11

An organic light emitting display device was manufactured in the same manner as in Experiment 4, except that Comparative Compound 5 was used as a light-emitting auxiliary layer instead of the compound of the present invention.

Comparative Example 12

An organic light emitting display device was manufactured in the same manner as in Experiment 4, except that Comparative Compound 6 was used as the light-emitting auxiliary layer instead of the compound of the present invention.

The electroluminescent (EL) characteristics of the organic light emitting diodes prepared by Experimental Example 4 and Comparative Examples were measured by applying a positive bias DC voltage to the photoresearch company PR-650, and the results are shown in Table 15 below. . At this time, the life was measured T90 life through the life measurement equipment manufactured by McScience Inc. at 300 cd / m ² reference luminance.

As can be seen from the results of Table 16, the device in which the compound of the present invention is used as the light emitting auxiliary layer material as compared to the case where the light emitting auxiliary layer is not used, Comparative Compound 5, Comparative Compound 6 as the light emitting auxiliary layer material, It was possible to lower the driving voltage of, and to significantly improve the luminous efficiency and lifetime. It has a high T1 energy level when the compound of the present invention having a pentagonal ring containing heteroatoms bonded to the core alone is used as a light emitting auxiliary layer, and lowers the driving voltage of the organic electroluminescent device due to the deep HOMO energy level. It can be explained by improving luminous efficiency and element lifetime.

It is apparent that similar effects can be obtained when the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, a hole injection layer, an electron injection layer, an electron transport layer and the like.

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 thereto. 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.

110 substrate 120 anode
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: cathode

Claims (13)

Compound represented by the following formula.
<Formula 1>

In Chemical Formula 1,
R ₁ to R ₄ are independently of each other iii) hydrogen, deuterium, halogen, C ₆ -C ₆₀ aryl group, fluorenyl group, C containing at least one hetero atom of O, N, S, Si and P ₂ to C ₆₀ heterocyclic group, C ₁ to C ₅₀ alkyl group, C ₂ to C ₂₀ alkenyl group and C ₁ to C ₃₀ alkoxyl group, or ii) R ₁ and R ₂ Or R ₃ and R ₄ combine with each other to form at least one ring (where a group that does not form a ring is as defined in iii),
R ₁₁ , R ₁₂ , R ₂₁ and R ₂₂ are each independently of the other hydrogen, deuterium, C ₆ ~ C ₆₀ aryl group, C ₂ ~ containing at least one hetero atom of O, N, S, Si and P It is selected from the group consisting of C ₆₀ heterocyclic group and C ₁ ~ C ₅₀ Alkyl group,
X ₁ and X ₂ are Independently of each other, NR ', O, S, CR'R "or SiR'R", a and b are integers of 0 or 1 (where a + b must be an integer of 1 or more), where R' and R "Is independently of each other C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P, C ₁ ~ C Selected from the group consisting of ₅₀ alkyl groups,
Y is selected from the group consisting of hydrogen, a C ₆ -C ₆₀ aryl group and a C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P, n is 0 or Is an integer of 1,
L is a single bond; C ₆ ~ C ₆₀ arylene group; Selected from the group consisting of a fluorenylene group and a heterocyclic group of C ₂ to C ₆₀ , each of these (except for a single bond) each of which is an alkyl group of C ₁ to C ₂₀ , an aryl group of C ₆ to C ₂₀ , and C ₂ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group of,
-L- (Y) _n comprises at least one C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si, and P.
(The above R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , R ', R "and Y Each, with one or more substituents selected from the group consisting of a heterocyclic group of C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ aryl group and C ₂ ~ C ₂₀ substituted with heavy hydrogen in the Can be substituted) The method of claim 1,
Compound represented by one of the following formula.
<Formula 2><Formula3>

(In the above formula, R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , X ₁ , X ₂ , Y, n and L are the same as defined in formula 1) The method of claim 1,
Compound represented by one of the following formula.
<Formula 4><Formula5>

,

<Formula 6><Formula7>

<Formula 8><Formula9>

(Wherein R ₁ , R ₂ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , X ₁ , X ₂ , L, Y and n are the same as defined in Formula 1) The method of claim 1,
Compound represented by one of the following formula.
<Formula 10><Formula11>

(In the above formula, R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , X ₁ , X ₂ , L, Ar ₁ and Ar ₂ are the same as defined in formula 1, Ar ₃ is C ₆ C ₂ ~ C ₆₀ heterocyclic group, C ₁ ~ C ₅₀ of the aryl group of ~ C ₆₀ , C ₂ ~ C ₂₀ alkenyl group, containing at least one hetero atom of O, N, S, Si and P Selected from the group consisting of an alkyl group and a fluorenyl group, Z ₁ to Z ₄ are each independently CR ₃₁ or N, wherein R ₃₁ is hydrogen, deuterium, halogen, silane group, cyano group, nitro group, C ₁ ~ an aryl group of C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group _{(alkenyl), C 6 ~ C} 20 of the, fluorene group, an aryl of C ₆ ~ C ₂₀ substituted with deuterium Group, C ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ Arylalkyl group and C ₈ ~ C ₂₀ arylalkenyl group) Compounds characterized in that represented by one of the following formula:
<Formula 12><Formula13>

In Chemical Formula 12 and Chemical Formula 13,
R ₁ to R ₄ are independently of each other iii) hydrogen, deuterium, halogen, C ₆ -C ₆₀ aryl group, fluorenyl group, C containing at least one hetero atom of O, N, S, Si and P ₂ to C ₆₀ heterocyclic group, C ₁ to C ₅₀ alkyl group, C ₂ to C ₂₀ alkenyl group and C ₁ to C ₃₀ alkoxyl group, or ii) R ₁ and R ₂ Or R ₃ and R ₄ combine with each other to form at least one ring (where a group that does not form a ring is as defined in iii),
R ₁₁ , R ₁₂ , R ₂₁ and R ₂₂ are each independently of the other hydrogen, deuterium, C ₆ ~ C ₆₀ aryl group, C ₂ ~ containing at least one hetero atom of O, N, S, Si and P It is selected from the group consisting of C ₆₀ heterocyclic group and C ₁ ~ C ₅₀ Alkyl group,
X ₁ and X ₂ are Independently of each other, NR ', O, S, CR'R "or SiR'R", a and b are integers of 0 or 1 (where a + b must be an integer of 1 or more), where R' and R "Is independently of each other C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P, C ₁ ~ C Selected from the group consisting of ₅₀ alkyl groups,
L is a single bond; C ₆ ~ C ₆₀ arylene group; Selected from the group consisting of a fluorenylene group and a heterocyclic group of C ₂ to C ₆₀ , each of these (except for a single bond) each of which is an alkyl group of C ₁ to C ₂₀ , an aryl group of C ₆ to C ₂₀ , and C ₂ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group of,
Ar ₁ and Ar ₂ are each independently a C ₆ ~ C ₆₀ aryl group, a fluorenyl group and a C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P It is selected from the group consisting of.
(The above R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , Ar ₁ and Ar ₂ are each C ₁ to C ₂₀ alkyl group, C ₆ to C ₂₀ aryl group, deuterated C ₆ to C ₂₀ aryl group and C ₂ ~ C ₂₀ It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group) Compounds characterized in that represented by one of the following formula:
<Formula 14><Formula15>

In Formula 14 and Formula 15,
R ₁₁ , R ₁₂ , R ₂₁ and R ₂₂ are each independently of the other hydrogen, deuterium, C ₆ ~ C ₆₀ aryl group, C ₂ ~ containing at least one hetero atom of O, N, S, Si and P It is selected from the group consisting of C ₆₀ heterocyclic group and C ₁ ~ C ₅₀ Alkyl group,
X ₁ and X ₂ are Independently of each other, NR ', O, S, CR'R "or SiR'R", a and b are integers of 0 or 1 (where a + b must be an integer of 1 or more), where R' and R "Is independently of each other C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P, C ₁ ~ C ₅₀ alkyl group and -LN (Ar ₁ ) (Ar ₂ );
Y is selected from the group consisting of hydrogen, a C ₆ -C ₆₀ aryl group and a C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P, n is 0 or Is an integer of 1,
L is a single bond; C ₆ ~ C ₆₀ arylene group; Selected from the group consisting of a fluorenylene group and a heterocyclic group of C ₂ to C ₆₀ , each of these (except for a single bond) each of which is an alkyl group of C ₁ to C ₂₀ , an aryl group of C ₆ to C ₂₀ , and C ₂ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group of,
Ar ₁ and Ar ₂ are each independently a C ₆ ~ C ₆₀ aryl group, fluorenyl group and C ₂ ~ C ₆₀ heterocyclic ring containing at least one hetero atom of O, N, S, Si and P It is selected from the group consisting of groups.
(The above R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , R ′, R ″, Y, Ar ₁ and Ar ₂ are each an alkyl group of C ₁ to C ₂₀ , C ₆ to C ₂₀ An aryl group, a C ₆ ~ C ₂₀ aryl group substituted with deuterium, and a C ₂ ~ C ₂₀ heterocyclic group may be substituted with one or more substituents selected from the group) Compounds characterized in that represented by one of the following formula:
<Formula 16><Formula17>

In Chemical Formulas 16 and 17,
R ₁ to R ₄ are independently of each other iii) hydrogen, deuterium, halogen, C ₆ -C ₆₀ aryl group, fluorenyl group, C containing at least one hetero atom of O, N, S, Si and P ₂ to C ₆₀ heterocyclic group, C ₁ to C ₅₀ alkyl group, C ₂ to C ₂₀ alkenyl group and C ₁ to C ₃₀ alkoxyl group, or ii) R ₁ and R ₂ Or R ₃ and R ₄ combine with each other to form at least one ring (where a group that does not form a ring is as defined in iii),
R ₁₁ , R ₁₂ , R ₂₁ and R ₂₂ are each independently of the other hydrogen, deuterium, C ₆ ~ C ₆₀ aryl group, C ₂ ~ containing at least one hetero atom of O, N, S, Si and P It is selected from the group consisting of C ₆₀ heterocyclic group and C ₁ ~ C ₅₀ Alkyl group,
Y is selected from the group consisting of hydrogen, a C ₆ -C ₆₀ aryl group and a C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P, n is 0 or Is an integer of 1,
L is a single bond; C ₆ ~ C ₆₀ arylene group; Selected from the group consisting of a fluorenylene group and a heterocyclic group of C ₂ to C ₆₀ , each of these (except for a single bond) each of which is an alkyl group of C ₁ to C ₂₀ , an aryl group of C ₆ to C ₂₀ , and C ₂ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of a heterocyclic group of,
Ar ₁ and Ar ₂ are each independently a C ₆ ~ C ₆₀ aryl group, a fluorenyl group and a C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P It is selected from the group consisting of.
(The above R ₁ to R ₄ , R ₁₁ , R ₁₂ , R ₂₁ , R ₂₂ , R ', R "and Y Each, with one or more substituents selected from the group consisting of a heterocyclic group of C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ aryl group and C ₂ ~ C ₂₀ substituted with heavy hydrogen in the Can be substituted) Compound which is one of the following compounds.

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 an organic electric device, characterized in that containing the compound of any one of claims 1 to 8. The method of claim 9,
An organic electric device, wherein the compound is formed into the organic material layer by a soluble process. The method of claim 9,
The organic material layer comprising the compound is an organic electroluminescent device, characterized in that the light emitting layer, hole transport layer or light emitting auxiliary layer. A display device comprising the organic electroluminescent element of claim 9; And
And a controller for controlling the display device. The method of claim 12,
The organic electronic 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 monochrome or white illumination device.

Images