KR20150124609A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving light emitting efficiency, stability, and lifespan of an element; an organic electronic element using the same; and an electronic device thereof. The compound is represented by chemical formula 1.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for organic electroluminescent devices, an organic electroluminescent device using the same, and an electronic device using the same. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent (EL)

TECHNICAL FIELD The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device therefor.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from an electron triplet excited state have. Further, the light emitting material can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color.

Currently, the portable display market is increasing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption is an important factor for portable displays, which have a limited power source, such as a battery, and efficiency and longevity are also important factors to be solved.

The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage drops and the driving voltage drops. As a result, crystallization of the organic material due to Joule heating, which occurs during driving, Indicating a tendency for the lifetime to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the material are achieved, long life and high efficiency can be achieved at the same time.

Generally, 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, the holes are moved faster than the electrons, and the excitons generated in the light emitting layer are transferred to the electron transporting layer, resulting in charge unbalance in the light emitting layer and light emission at the electron transporting layer interface. When light is emitted from the interface of the electron transport layer, the color purity and efficiency of the organic electronic device are deteriorated. In particular, when the organic electronic device is manufactured, the stability of the organic electronic device is deteriorated and the lifetime of the organic electronic device is shortened. Therefore, the development of an electron transporting material which has a high temperature stability and a high electron mobility (within a blue device driving voltage range of a full device) while improving a hole blocking ability at a high T1 value This is the point of need.

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

In one aspect, the invention provides compounds represented by the 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, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and lifetime of the device.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference numerals even though they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

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

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

As used herein, the term "alkyl" or "alkyl group " refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, a cycloalkyl-substituted alkyl group.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.

The term "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced by a heteroatom.

The term "alkenyl group" or "alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxyl group "," alkoxy group ", or "alkyloxy group" used in the present invention means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has a carbon number of 1 to 60, It is not.

The term "alkenoyl group "," alkenoyl group ", "alkenyloxy group ", or" alkenyloxy group "as used in the present invention means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.

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

The terms "aryl group" and "arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirobifluorene group, or a spirobifluorene group.

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

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

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.

The term "heterocyclic group ", as used herein, unless otherwise specified, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, Aromatic rings. Adjacent functional groups may be combined and formed.

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

The "heterocyclic group" may also include a ring containing SO ₂ in place of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

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

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

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

Unless otherwise specified, the term "carbonyl" as used herein refers to -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group of 2 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise indicated, the term "ether" used in the present invention refers to -RO-R 'wherein R or R' are each independently of the other hydrogen, an alkyl group having 1 to 20 carbon atoms, An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as follows: and wherein R ¹ may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.

1 is an illustration of an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent 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, ) Comprising an organic compound layer comprising a compound according to the present invention. In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, the remaining layers except the light emitting layer 150 may not be formed. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to the present invention may further include a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer may be a host or a dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, It can be used as a material. Preferably, the compound of the present invention may be used as an electron transporting layer 160 material.

On the other hand, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at any position even in the same core, the selection of the core and the combination of the sub- Especially when the optimum combination of energy level and T1 value between the organic layers, intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long lifetime and high efficiency can be achieved at the same time.

By forming the electron transporting layer 160 using the compound of the present invention, the energy level and T1 value between each organic layer, the mobility, the interface characteristics, and the like of the material are optimized to improve the lifetime and efficiency of the organic electronic device Can be improved at the same time.

The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a physical vapor deposition (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 a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, and an electron transporting layer 160 and an electron injection layer 170, and then depositing a material usable as the cathode 180 on the organic layer.

In addition, the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

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

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down , And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light from the electroluminescent material. Can be applied to such WOLED.

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochrome or white illumination.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. 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 according to one aspect of the present invention will be described.

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

≪ Formula 1 >

In the above formula (1), the definition of each symbol is as follows.

At least one of X ¹ to X ⁴ is N, and the others are independently of each other CH, CR or N. Therefore, X ¹ To X ⁴ May be N, two or three of them may be N, and all of them may be N. [ Wherein R is a C ₆ to C ₆₀ aryl group, a fluorenyl group, a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P, a C ₃ to C ₆₀ A fused ring group of an aliphatic ring of C ₆ to C ₆₀ aromatic ring, a C ₁ to C ₅₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₂ to C ₂₀ alkynyl group, a C ₁ to C ₃₀ alkoxy group And an aryloxy group having ₆ to ₃₀ carbon atoms.

L is a date may aryl group, or a fluorene-ylene a single bond, C ₆ ~ C _60, such as phenyl, naphthyl, biphenyl, 9,9-dimethyl-fluorenyl, 9,9-diphenyl--9 H - Fluorenyl, spirofluorenyl, and the like.

R ¹ and R ⁴ independently of one another may be hydrogen or a C ₆ -C ₆₀ aryl group, for example the aryl group may be phenyl, biphenyl, naphthyl, and the like. R ^{2 may} also be a C ₆ to C ₆₀ aryl group, and specifically may be phenyl, biphenyl, naphthyl, and the like.

R ³ may be a C ₆ to C ₆₀ aryl group or a C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P, Naphthyl, pyridine, pyrimidine, triazine, quinoxaline, quinazoline, benzoimidazole and the like, each of which may further be substituted with an aryl group, a heterocyclic group and the like.

When L is an arylene group or a fluorenylene group and when R, R ¹ , R ^2, and R ³ are independently an aryl group, or when R and R ³ are independently a heterocycle, and when R is A fluorenyl group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group or an aryloxy group, each of these may be independently selected from the group consisting of deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ to C ₂₀ ; And an arylalkenyl group having from ₈ to ₂₀ carbon atoms.

When each symbol of the formula (1) or a group substituted therefor is an aryl group or an arylene group, it may be an aryl group or an arylene group having 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and more preferably 6 to 30 carbon atoms, The heterocyclic group may be a heterocycle having 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms. When the heterocyclic group is an alkyl group, it may have 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, More preferably an alkyl group having 1 to 20 carbon atoms, and particularly preferably an alkyl group having 1 to 10 carbon atoms.

Specifically, the formula (1) may be represented by one of the following formulas (2) to (8).

(2) (3) ≪ Formula 4 > ≪ Formula 5 >

(6) ≪ Formula 7 > (8)

In the above Chemical Formulas 2 to 8, L, R ¹ to R ⁴ are as defined in Chemical Formula (1).

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

In another embodiment, the present invention provides a compound for an organic electroluminescent device represented by the general formula (1).

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

The organic electroluminescent device includes a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode. The organic material layer may include a compound represented by Formula 1, and Formula 1 may be contained in an electron transport layer of the organic material layer.

Specifically, the organic electroluminescent device includes one of the compounds represented by Chemical Formulas (2) to (8) in the organic material layer. More specifically, Organic electroluminescent device.

In another embodiment of the present invention, the light efficiency improving layer is formed on at least one side of the one side of the first electrode opposite to the organic layer, or one side of the one side of the second electrode opposite to the organic layer, And an organic electroluminescent device.

On the other hand, the compound contained in the organic material layer may be composed of the same kind of compound, but it may be a mixture of two or more different kinds of compounds represented by the general formula (1). For example, the electron transport layer of the organic material layer according to the present invention may contain two different compounds such as the above-mentioned individual compounds 1-1 and 1-2, May contain more than one species of different compounds.

Hereinafter, synthesis examples of the compound represented by formula (1) according to the present invention and production examples of organic electroluminescent devices will be described in detail with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

The final products according to the present invention can be prepared by reacting Sub A and Sub B as shown in Reaction Scheme 1 below, but are not limited thereto.

<Reaction Scheme 1>

One. Sub  Example of synthesis of A

Sub A of Scheme 1 can be synthesized by way of example as shown in Reaction Scheme 2 below.

<Reaction Scheme 2>

The synthesis examples of specific compounds belonging to Sub A synthesized by the reaction path of the above-mentioned reaction formula 2 are as follows.

(One) Sub  A1- 1 of  synthesis

<Reaction Scheme 3>

Sub  A (3) 1- 1 of  synthesis

Sub A (2) -1 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol) and Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) were added to a round bottom flask, Respectively. After dissolving all the reactants, Sub A (1) -1 (3.57 g, 35 mmol) was slowly added dropwise under nitrogen and the mixture was stirred at room temperature for 4 hours. The reaction solution was filtered through silica gel to remove the catalyst and salts, and washed with normal hexane. The solvent of the filtered solution was all removed to obtain 6.41 g of Sub A (3) 1-1. (Yield: 71%).

Sub  A (4) 1- 1 of  synthesis

(6.94 g, 27.3 mmol), Pd (dppf) Cl ₂ catalyst (0.55 g, 0.75 mmol), and KOAc (3 ml) were dissolved in toluene, (7.31 g, 74.5 mmol) were added in this order, followed by stirring for 24 hours to synthesize a borate compound. Thereafter, the resulting borate compound was separated through a silica gel column and recrystallization to obtain 5.61 g of Sub A (4) 1-1. (Yield: 74%).

Sub  A (6) 1- 1 of  synthesis

Sub A (4) 1-1 (5.61 g, 18.4 mmol), Sub A (5) -1 (3.56 g, 18.4 mmol), Pd (PPh ₃ ) ₄ (0.64, 0.55 mmol), K ₂ CO ₃ g, 55.15 mol) was dissolved in anhydrous THF and a small amount of water, and the mixture was refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ and filtered under reduced pressure. The organic solvent was concentrated and the resulting product was separated by column chromatography to obtain 3.86 g of the desired Sub A (6) 1-1 (Yield: 72 %)

Sub  A (7) 1- 1 of  synthesis

Sub A (6) 1-1 (3.86 g, 13.2 mmol) was dissolved in methylene chloride in a round bottom flask and cooled to -78 ° C. Under nitrogen, a 1.0 M solution of Iodine monochloride (2.15 g, 2.58 mmol) was slowly added dropwise and stirred at room temperature for 4 hours. The reaction was terminated by adding saturated NaHSO ₃ solution, extracted with methylene chloride and water, and then separated by column chromatography to obtain 4.14 g of the desired Sub A (7) 1-1. (Yield: 75%).

Sub  A1- 1 of  synthesis

Sub A (7) 1-1 (4.14 g, 9.9 mmol), Sub A (8) -1 (1.21 g, 9.9 mmol), Pd (PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ 4.11 g, 29.7 mmol) was dissolved in anhydrous THF and a small amount of water, and refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain 2.66 g of desired Sub A1-1. (Yield: 73%)

(2) Sub  A1- 2 of  synthesis

<Reaction Scheme 4>

Sub  A (3) 1- 2 of  synthesis

Sub A (2) -1 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 5.33 g, 35 mmol) was subjected to the synthesis of Sub A (3) 1-1 to obtain 7.87 g of Product Sub A (3) 1-2. (Yield: 73%)

Sub  A (4) 1- 2 of  synthesis

(7.16 g, 28.1 mmol), Pd (dppf) Cl ₂ catalyst (0.56 g, 0.77 mmol) and KOAc (7.52 g, 25.5 mmol) were added to a solution of Sub A 3 1-2 (7.87 g, 25.5 mmol), toluene, bispinacolatodiborone , 76.6 mmol) was obtained 6.44 g of the product Sub A (4) 1-2 using the above Sub A (4) 1-1 synthesis method. (Yield: 71%).

Sub  A (6) 1- 2 of  synthesis

Sub A (4) 1-2 (6.44g , 18.13mmol) and Sub A (5) -1 (3.51g , 18.13mmol), Pd (PPh 3) 4 (0.63g, 0.54mmol), K 2 CO 3 ( 7.5 g, 54.4 mmol) was dissolved in anhydrous THF and a small amount of water, and 4.64 g of product Sub A (6) 1-2 was obtained using Sub A (6) 1-1. (Yield: 75%).

Sub  A (7) 1- 2 of  synthesis

Sub A (6) 1-2 (4.64 g, 13.6 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.64 g, 16.3 mmol) and saturated NaHSO ₃ solution 4.63 g of the product Sub A (7) 1-2 was obtained. (Yield: 73%)

Sub  A1- 2 of  synthesis

Sub A (7) 1-2 (4.63g , 9.9mmol) and Sub A (8) -2 (1.7g , 9.9mmol), Pd (PPh 3) 4 (0.34g, 0.3mmol), K 2 CO 3 ( 8.3 g, 60 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.47 g of the product Sub A1-2 was obtained using the Sub A1-1 synthesis method. (Yield: 75%).

(3) Sub  A2- 1 of  synthesis

<Reaction Scheme 5>

Sub  A (3) 2- 1 of  synthesis

Sub A (2) -2 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 3.57g, 35mmol) was obtained 6.6g of the product Sub A (3) 2-1 using the Sub A (3) 1-1 synthesis method. (Yield: 73%)

Sub  A (4) 2- 1 of  synthesis

Pd (dppf) Cl ₂ catalyst (0.56 g, 0.77 mmol), KOAc (7.53 g, 0.77 mmol), Sub A (3) 2-1 (6.6 g, 25.6 mmol), toluene, bispinacolatodiborone , 76.7 mmol) was subjected to the synthesis of Sub A (4) 1-1 to obtain 5.54 g of the product Sub A (4) 2-1. (Yield: 71%).

Sub  A (6) 2- 1 of  synthesis

Sub A (4) 2-1 (5.54g , 18.15mmol) and Sub A (5) -1 (3.5g , 18.15mmol), Pd (PPh 3) 4 (0.63g, 0.54mmol), K 2 CO 3 ( 7.53 g, 54.5 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.92 g of the product Sub A (6) 2-1 was obtained using the Sub A (6) 1-1 synthesis method. (Yield: 74%).

Sub  A (7) 2- 1 of  synthesis

Sub A (6) 2-1 (3.92 g, 13.4 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.62 g, 16.1 mmol) and saturated NaHSO ₃ solution 3.98 g of the product Sub A (7) 2-1 was obtained. (Yield: 71%).

Sub  Synthesis of A2-1

Sub A (7) 2-1 (3.98g , 9.53mmol) and Sub A (8) -1 (1.16g , 9.53mmol), Pd (PPh 3) 4 (0.33g, 0.29mmol), K 2 CO 3 ( 3.95 g, 28.6 mmol) was dissolved in anhydrous THF and a small amount of water, and 2.63 g of the product Sub A2-1 was obtained using the Sub A1-1 synthesis method. (Yield: 75%).

(4) Sub  A2- 8 of  synthesis

<Reaction Scheme 6>

Sub  A (3) 2- 1 of  synthesis

Sub A (2) -2 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 3.57 g, 35 mmol) was obtained in the same manner as in Sub A (3) 1-1, except that 6.5 g of the product Sub A (3) 2-1 was obtained. (Yield: 72%).

Sub  A (4) 2- 1 of  synthesis

Sub A (3) 2-1 (6.5g , 34.3mmol), toluene, bis pinacolato Todai boron (7.03g, 27.7mmol), Pd ( dppf) Cl 2 catalyst (0.55g, 0.76mmol), KOAc ( 7.41g , 75.55 mmol) was obtained 5.69 g of the product Sub A (4) 2-1 using the Sub A (4) 1-1 synthesis method. (Yield: 74%).

Sub  A (6) 2- 8 of  synthesis

Sub A (4) 2-1 (5.69g , 18.6mmol) and Sub A (5) 2-3 (5.96g , 18.6mmol), Pd (PPh 3) 4 (0.65g, 0.56mmol), K 2 CO 3 (7.7 g, 55.9 mmol) was dissolved in anhydrous THF and a small amount of water to obtain 5.61 g of the product Sub A (6) 2-8 using Sub A (6) 1-8 synthesis method. (Yield: 72%).

Sub  A (7) 2- 8 of  synthesis

Sub A (6) 2-8 (5.61 g, 13.4 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.62 g, 16.1 mmol) and saturated NaHSO ₃ solution 5.18 g of the product Sub A (7) 2-8 was obtained. (Yield: 71%).

Sub  A2- 8 of  synthesis

Sub A (7) 2-8 (5.18g , 9.53mmol) and Sub A (8) -1 (1.16g , 9.53mmol), Pd (PPh 3) 4 (0.33g, 0.29mmol), K 2 CO 3 ( 3.95 g, 28.6 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.48 g of the product Sub A2-8 was obtained using the Sub A1-1 synthesis method. (Yield: 74%).

(5) Sub  A3- 1 of  synthesis

<Reaction Scheme 7>

Sub  A (3) 3- 1 of  synthesis

Sub A (2) -3 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 3.57 g, 35 mmol) was obtained 6.6 g of the product Sub A (3) 3-1 using the Sub A (3) 1-1 synthesis method described above. (Yield: 73%)

Sub  A (4) 3- 1 of  synthesis

Pd (dppf) Cl ₂ catalyst (0.56 g, 0.77 mmol), KOAc (7.53 g, 0.77 mmol), Sub A (3) 3-1 (6.6 g, 25.6 mmol), toluene, bispinacolatodiborone , 76.7 mmol) was used to obtain 5.54 g of the product A (4) 3-1 using the Sub A (4) 1-1 synthesis method. (Yield: 71%).

Sub  A (6) 3- 1 of  synthesis

Sub A (4) 3-1 (5.54g , 18.15mmol) and Sub A (5) -1 (3.5g , 18.15mmol), Pd (PPh 3) 4 (0.63g, 0.54mmol), K 2 CO 3 ( 7.53 g, 54.5 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.92 g of the product Sub A (6) 3-1 was obtained using the Sub A (6) 1-1 synthesis method described above. (Yield: 74%).

Sub  A (7) 3- 1 of  synthesis

Sub A (6) 3-1 (3.92 g, 13.44 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.62 g, 16.1 mmol) and saturated NaHSO ₃ solution 4.04 g of the product Sub A (7) 3-1 was obtained. (Yield: 72%).

Sub  A3- 1 of  synthesis

Sub A (7) 3-1 (4.04 g, 14 mmol), Sub A (8) -1 (1.78 g, 14 mmol), Pd (PPh ₃ ) ₄ (0.34 g, 0.29 mmol), K ₂ CO ₃ , 29 mmol) was dissolved in anhydrous THF and a small amount of water, and 2.6 g of the product Sub A3-1 was obtained using the Sub A1-1 synthesis method. (Yield: 73%)

(6) Sub  A3- 5 of  synthesis

<Reaction Scheme 8>

Sub  A (3) 3- 5 of  synthesis

Sub A (2) -3 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 6.24 g, 35 mmol) was used to obtain 8.54 g of the product Sub A (3) 3-5 using the above Sub A (3) 1-1 synthesis method. (Yield: 73%)

Sub  A (4) 3- 5 of  synthesis

Sub A (3) 3-5 (8.54g , 25.5mmol), toluene, bis pinacolato Todai boron (7.14g, 28.1mmol), Pd ( dppf) Cl 2 catalyst (0.56g, 0.77mmol), KOAc ( 7.52g , 76.66 mmol) was obtained 6.92 g of the product Sub A (4) 3-5 using the Sub A (4) 1-1 synthesis method. (Yield: 71%).

Sub  A (6) 3- 5 of  synthesis

Sub A (4) 3-5 (6.92g , 18.15mmol) and Sub A (5) -1 (3.51g , 18.15mmol), Pd (PPh 3) 4 (0.63g, 0.54mmol), K 2 CO 3 ( 7.53 g, 54.4 mmol) was dissolved in anhydrous THF and a small amount of water, and 5 g of product Sub A (6) 3-5 was obtained using Sub A (6) 1-1. (Yield: 75%).

Sub  A (7) 3- 5 of  synthesis

Sub A (6) 3-5 (5 g, 13.6 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.65 g, 16.3 mmol) and saturated NaHSO ₃ solution were added to the product 4.9 g of Sub A (7) 3-5 was obtained. (Yield: 73%)

Sub  A3- 5 of  synthesis

Sub A (7) 3-5 (4.9 g, 9.9 mmol), Sub A (8) -4 (1.97 g, 9.9 mmol), Pd (PPh ₃ ) ₄ (0.34 g, 0.3 mmol), K ₂ CO ₃ 4.11 g, 29.8 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.82 g of the product Sub A3-5 was obtained using the Sub A1-1 synthesis method. (Yield: 74%).

(7) Sub  Synthesis of A4-1

<Reaction Scheme 9>

Sub  A (3) 4- 1 of  synthesis

Sub A (2) -4 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 3.57 g, 35 mmol) was obtained 6.6 g of the product Sub A (3) 4-1 using the above Sub A (3) 1-1 synthesis method. (Yield: 73%)

Sub  A (4) 4- 1 of  synthesis

Sub A (3) 4-1 (6.6g , 25.6mmol), toluene, bis pinacolato Todai boron (7.1g, 28.1mmol), Pd ( dppf) Cl 2 catalyst (0.56g, 0.77mmol), KOAc ( 7.53g , 76.7 mmol) was subjected to the synthesis of Sub A (4) 1-1 to obtain 5.54 g of the product Sub A (4) 4-1. (Yield: 71%).

Sub  A (6) 4- 1 of  synthesis

Sub A (4) 4-1 (5.54g , 18.15mmol) and Sub A (5) -1 (3.51g , 18.15mmol), Pd (PPh 3) 4 (0.63g, 0.54mmol), K 2 CO 3 ( 7.53 g, 54.5 mmol) was dissolved in anhydrous THF and a small amount of water, and 4.02 g of the product Sub A (6) 4-1 was obtained using the Sub A (6) 1-1 synthesis method. (Yield: 76%).

Sub  A (7) 4- 1 of  synthesis

A solution of SubA (6) 4-1 (4.02 g, 13.8 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.68 g, 16.54 mmol) and saturated NaHSO ₃ solution was obtained using the Sub A 4.2 g of the product Sub A (7) 4-1 was obtained. (Yield: 73%)

Sub  A4- 1 of  synthesis

Sub A (7) 4-1 (4.2g , 10.06mmol) and Sub A (8) -1 (1.23g , 10.06mmol), Pd (PPh 3) 4 (0.35g, 0.3mmol), K 2 CO 3 ( 4.17 g, 30.2 mmol) was dissolved in anhydrous THF and a small amount of water, and 2.74 g of the product Sub A4-1 was obtained using the Sub A1-1 synthesis method described above. (Yield: 74%).

(8) Sub  Synthesis of A4-8

<Reaction formula 10>

Sub  Synthesis of A (3) 4-1

Sub A (2) -4 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 3.57 g, 35 mmol) was obtained 6.6 g of the product Sub A (3) 4-1 using the above Sub A (3) 1-1 synthesis method. (Yield: 73%)

Sub  Synthesis of A (4) 4-1

Sub A (3) 4-1 (6.6g , 25.6mmol), toluene, bis pinacolato Todai boron (7.1g, 28.1mmol), Pd ( dppf) Cl 2 catalyst (0.56g, 0.77mmol), KOAc ( 7.53g , 76.7 mmol) was subjected to the synthesis of Sub A (4) 1-1 to obtain 5.54 g of the product Sub A (4) 4-1. (Yield: 71%).

Sub  A (6) 4-8 Synthesis

Sub A (4) 4-1 (5.54g , 18.15mmol) and Sub A (5) -3 (5.8g , 18.15mmol), Pd (PPh 3) 4 (0.63g, 0.54mmol), K 2 CO 3 ( 7.53 g, 54.5 mmol) was dissolved in anhydrous THF and a small amount of water, and 5.6 g of the product Sub A (6) 4-8 was obtained using the Sub A (6) synthesis method. (Yield: 74%).

Sub  A (7) 4- 8 of  synthesis

Sub A (6) 4-8 (5.6 g, 13.4 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.61 g, 16.1 mmol) and saturated NaHSO ₃ solution 5.17 g of the product Sub A (7) 4-8 was obtained. (Yield: 71%).

Sub  Synthesis of A4-8

Sub A (7) 4-8 (5.17 g, 9.51 mmol), Sub A (8) -1 (1.16 g, 9.51 mmol), Pd (PPh ₃ ) ₄ (0.33 g, 0.29 mmol), K ₂ CO ₃ 3.94 g, 28.5 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.5 g of the product Sub A4-8 was obtained using the Sub A1-1 synthesis method. (Yield: 75%).

(9) Sub  A5- 1 of  synthesis

<Reaction Scheme 11>

Sub  A (3) 5- 1 of  synthesis

Sub A (2) -5 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 3.57 g, 35 mmol) was used to obtain 6.6 g of the product Sub A (3) 5-1 using the Sub A (3) 1-1 synthesis method. (Yield: 73%)

Sub  A (4) 5- 1 of  synthesis

Sub A (3) 5-1 (6.6g , 25.6mmol), toluene, bis pinacolato Todai boron (7.1g, 28.1mmol), Pd ( dppf) Cl 2 catalyst (0.56g, 0.77mmol), KOAc ( 7.53g , 76.7 mmol) was subjected to the synthesis of Sub A (4) 1-1 to obtain 5.54 g of the product Sub A (4) 5-1. (Yield: 71%).

Sub  A (6) 5- 1 of  synthesis

Sub A (5) -1 (3.5 g, 18.15 mmol), Pd (PPh ₃ ) ₄ (0.63 g, 0.54 mmol), K ₂ CO ₃ 7.53 g, 54.5 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.92 g of the product Sub A (6) 5-1 was obtained using the Sub A (6) 1-1 synthesis method. (Yield: 74%).

Sub  A (7) 5- 1 of  synthesis

Sub A (6) 5-1 (5.54 g, 18.15 mmol), methylene chloride, a 1.0 M solution of Iodine monochloride (2.62 g, 16.1 mmol) and a saturated NaHSO ₃ solution 3.98 g of the product Sub A (7) 5-1 was obtained. (Yield: 71%).

Sub  A5- 1 of  synthesis

Sub A (7) 5-1 (3.98g , 9.53mmol) and Sub A (8) -1 (1.16g , 9.53mmol), Pd (PPh 3) 4 (0.33g, 0.29mmol), K 2 CO 3 ( 3.95 g, 28.6 mmol) was dissolved in anhydrous THF and a small amount of water, and 2.63 g of the product Sub A5-1 was obtained using the Sub A1-1 synthesis method. (Yield: 75)

(10) Sub  A5- 4 of  synthesis

<Reaction Scheme 12>

Sub  A (3) 5- 4 of  synthesis

Sub A (2) -5 (8.32 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 6.24 g, 35 mmol) was subjected to synthesis of Sub A (3) 1-1 to obtain 8.33 g of the product Sub A (3) 5-4. (Yield: 71%).

Sub  A (4) 5- 4 of  synthesis

Sub A (3) 5-4 (8.33g , 24.9mmol), toluene, bis pinacolato Todai boron (6.9g, 27.3mmol), Pd ( dppf) Cl 2 catalyst (0.55g, 0.75mmol), KOAc ( 7.32g , 74.6 mmol) was obtained 6.93 g of the product Sub A (4) 5-4 using the Sub A (4) 1-1 synthesis method. (Yield: 73%)

Sub  A (6) 5- 4 of  synthesis

Sub A (5) -1 (3.5 g, 18.1 mmol), Pd (PPh ₃ ) ₄ (0.63 g, 0.54 mmol), K ₂ CO ₃ 7.52 g, 54.4 mmol) was dissolved in anhydrous THF and a small amount of water, and 5 g of the product Sub A (6) 5-4 was obtained using Sub A (6) 1-1. (Yield: 74%).

Sub  A (7) 5- 4 of  synthesis

Sub A (6) 5-4 (5 g, 13.6 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.64 g, 16.3 mmol) and saturated NaHSO ₃ solution were added to the product 4.83 g of Sub A (7) 5-4 was obtained. (Yield: 72%).

Sub  A5- 4 of  synthesis

Sub A (7) 5-4 (4.83 g, 9.76 mmol), Sub A (8) -5 (2.67 g, 9.76 mmol), Pd (PPh ₃ ) ₄ (0.34 g, 0.29 mmol), K ₂ CO ₃ 4.05 g, 29.3 mmol) was dissolved in anhydrous THF and a small amount of water, and 4.31 g of Sub A5-4 was obtained using the Sub A1-1 synthesis method. (Yield: 74%).

(11) Sub  A6- 1 of  synthesis

<Reaction Scheme 13>

Sub  A (3) 6- 1 of  synthesis

Sub A (2) -6 (8.29 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 3.57 g, 35 mmol) was obtained in the same manner as in Sub A (3) 1-1, except that 6.5 g of the product Sub A (3) 6-1 was obtained. (Yield: 72%).

Sub  A (4) 6- 1 of  synthesis

Pd (dppf) Cl ₂ catalyst (0.55 g, 0.76 mmol), KOAc (7.4 g, 27.7 mmol), toluene, bispinacolatodiborone (7.03 g, 27.7 mmol) , 75.5 mmol) was subjected to the synthesis of Sub A (4) 1-1 to obtain 5.38 g of the product Sub A (4) 6-1. (Yield: 70%).

Sub  A (6) 6- 1 of  synthesis

Sub A (4) 6-1 (5.38g , 12.9mmol) and Sub A (5) -1 (1.57g , 12.9mmol), Pd (PPh 3) 4 (0.45g, 0.39mmol), K 2 CO 3 ( 5.34 g, 38.6 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.5 g of the product Sub A (6) 6-1 was obtained using Sub A (6) 1-1. (Yield: 74%).

Sub  A (7) 6- 1 of  synthesis

Sub A (6) 6-1 (3.5 g, 11.5 mmol), methylene chloride, 1.0 M solution of Iodine monochloride (2.34 g, 14.4 mmol) and saturated NaHSO ₃ solution To obtain 3.66 g of the product Sub A (7) 6-1. (Yield: 73%)

Sub  A6- 1 of  synthesis

Sub A (7) 6-1 (3.66g , 8.76mmol) and Sub A (8) -1 (1.07g , 8.76mmol), Pd (PPh 3) 4 (0.3g, 0.26mmol), K 2 CO 3 ( 3.63 g, 26.3 mmol) was dissolved in anhydrous THF and a small amount of water, and 2.39 g of the product Sub A6-1 was obtained using the above Sub A1-1 synthesis method. (Yield: 74%).

(12) Sub  A6- 5 of  synthesis

<Reaction Scheme 14>

Sub  A (3) 6- 5 of  synthesis

Sub A (2) -6 (8.32 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 6.24 g, 35 mmol) was subjected to synthesis of Sub A (3) 1-1 to obtain 8.45 g of product Sub A (3) 6-51. (Yield: 72%).

Sub  A (4) 6- 5 of  synthesis

Sub A (3) 6-5 (8.44g , 25.2mmol), toluene, bis pinacolato Todai boron (7g, 27.7mmol), Pd ( dppf) Cl 2 catalyst (0.55g, 0.76mmol), KOAc ( 7.4g, 75.5 mmol) was obtained in the same manner as in Sub A (4) 1-1, except that 7 g of the product Sub A (4) 6-5 was obtained. (Yield: 73%)

Sub  A (6) 6- 5 of  synthesis

Sub A (4) 6-5 (7 g, 18.3 mmol), Sub A (5) -1 (3.54 g, 18.3 mmol), Pd (PPh ₃ ) ₄ (0.63 g, 0.55 mmol), K ₂ CO ₃ g, 54.9 mmol) was dissolved in anhydrous THF and a small amount of water, and 4.8 g of product Sub A (6) 6-5 was obtained using Sub A (6) 1-1. (Yield: 71%).

Sub  A (7) 6- 5 of  synthesis

Sub A (6) 6-5 (4.8 g, 13 mmol), methylene chloride, a 1.0 M solution of Iodine monochloride (2.5 g, 15.6 mmol) and a saturated NaHSO ₃ solution were added to the product 4.7 g of Sub A (7) 6-5 was obtained. (Yield: 73%)

Sub  A6- 5 of  synthesis

Sub A (7) 6-5 (4.7 g, 9.5 mmol), Sub A (8) -4 (1.88 g, 9.5 mmol), Pd (PPh ₃ ) ₄ (0.33 g, 0.29 mmol), K ₂ CO ₃ 3.94 g, 28.5 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.17 g of the product Sub A6-5 was obtained using the Sub A1-1 synthesis method. (Yield: 75%).

Sub  A7- 1 of  synthesis

<Reaction Scheme 15>

Sub  A (3) 7- 1 of  synthesis

Sub A (2) -7 (8.32 g, 29.2 mmol), copper (I) iodide (0.28 g, 1.46 mmol), Pd (PPh ₃ ) ₄ (0.68 g, 0.58 mmol) 3.57 g, 35 mmol) was obtained 6.62 g of the product Sub A (3) 7-1 using the above Sub A (3) 1-1 synthesis method. (Yield: 73%)

Sub  A (4) 7- 1 of  synthesis

(7.16 g, 28.1 mmol), Pd (dppf) Cl ₂ catalyst (0.56 g, 0.77 mmol), KOAc (7.5 g, , 76.6 mmol) was used to obtain 5.7 g of the product Sub A (4) 7-1 using the Sub A (4) 1-1 synthesis method. (Yield: 73%)

Sub  A (6) 7- 1 of  synthesis

Sub A (4) 7-1 (5.7g , 18.6mmol) and Sub A (5) -1 (3.6g , 18.6mmol), Pd (PPh 3) 4 (0.65g, 0.56mmol), K 2 CO 3 ( 7.72 g, 55.8 mmol) was dissolved in anhydrous THF and a small amount of water, and 4 g of the product Sub A (6) 7-1 was obtained using Sub A (6) 1-1. (Yield: 74%).

Sub  A (7) 7- 1 of  synthesis

Sub A (6) 7-1 (4 g, 13.7 mmol), methylene chloride, a 1.0 M solution of Iodine monochloride (2.66 g, 16.4 mmol) and a saturated NaHSO ₃ solution were added to the product Sub A (7) 7-1 was obtained in an amount of 4.06 g. (Yield: 71%).

Sub  A7- 1 of  synthesis

Sub A (7) 7-1 (4.06 g, 9.7 mmol), Sub A (8) -1 (1.18 g, 9.7 mmol), Pd (PPh ₃ ) ₄ (0.34 g, 0.29 mmol), K ₂ CO ₃ 4g, 29.1 mmol) was dissolved in anhydrous THF and a small amount of water, and 2.61 g of the product Sub A7-1 was obtained using the Sub A1-1 synthesis method. (Yield: 73%)

(14) Sub  A7- Ten  synthesis

<Reaction Scheme 16>

Sub  A (3) 7- Ten  synthesis

Sub A (2) -7 (9.5 g, 33.36 mmol), copper (I) iodide (0.32 g, 1.67 mmol), Pd (PPh ₃ ) ₄ (0.77 g, 0.67 mmol) 1.04 g, 40 mmol) was obtained in the same manner as in Sub A (3) 1-1. 5.2 g of the product Sub A (3) 7-10 was obtained. (Yield: 71%).

Sub  A (4) 7- Ten  synthesis

Sub A (3) 7-10 (5.2g , 28.4mmol), toluene, bis pinacolato Todai boron (7.94g, 31.3mmol), Pd ( dppf) Cl 2 catalyst (0.62g, 0.85mmol), KOAc ( 8.4g , 85.2 mmol) was subjected to the synthesis of Sub A (4) 1-1 to obtain 4.77 g of the product Sub A (4) 7-10. (Yield: 73%)

Sub  A (6) 7- Ten  synthesis

Sub A (4) 7-10 (4.77g , 20.7mmol) and Sub A (5) -4 (7.16g , 20.7mmol), Pd (PPh 3) 4 (0.72g, 0.62mmol), K 2 CO 3 ( 8.6 g, 62.2 mmol) was dissolved in anhydrous THF and a small amount of water, and then 5.6 g of the product Sub A (6) 7-10 was obtained using Sub A (6) 1-1. (Yield: 73%)

Sub  A (7) 7- Ten  synthesis

Sub A (6) 7-10 (5.6 g, 15.2 mmol), methylene chloride, a 1.0 M solution of Iodine monochloride (3 g, 18.2 mmol) and a saturated NaHSO ₃ solution were added to the product 5.4 g of Sub A (7) 7-10 was obtained. (Yield: 72%).

Sub  A7- Ten  synthesis

Sub A (7) 7-10 (5.41g , 10.9mmol) and Sub A (8) -1 (1.33g , 10.9mmol), Pd (PPh 3) 4 (0.38g, 0.33mmol), K 2 CO 3 ( 4.53 g, 32.7 mmol) was dissolved in anhydrous THF and a small amount of water, and 3.64 g of the product Sub A7-10 was obtained using the Sub A1-1 synthesis method. (Yield: 75%).

Sub Of A  example

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

[Table 1]

2. Sub Of B  Synthetic example

Sub B of Scheme 1 can be synthesized by the reaction path of Scheme 17 below.

<Reaction Scheme 17>

A synthesis example of a specific compound belonging to Sub B synthesized by the reaction path of the above reaction scheme 17 is as follows.

(One) Sub  B- 3 of  synthesis

<Reaction Scheme 18>

(5.58 g, 22 mmol), Pd (dppf) Cl ₂ catalyst (0.44 g, 0.6 mmol), KOAc (5.89 g, 60 mmol) in toluene after dissolving Sub B (3) ) Were added in this order, followed by stirring for 24 hours to synthesize a borate compound. The resulting compound was separated through a silicagel column and recrystallization to obtain 3.8 g of Sub B-3. (Yield: 75%).

(2) Sub  B- 6 of  synthesis

<Reaction Scheme 19>

Pd (dppf) Cl ₂ catalyst (0.44 g, 0.6 mmol) and KOAc (5.89 g, 60 mmol) were added to a reaction vessel equipped with a stirrer, Sub B-3 synthesis method was used to obtain 5.32 g of the product Sub B-6. (Yield: 74%).

(3) Sub  B- Of 36  synthesis

<Reaction Scheme 20>

(5.59 g, 22 mmol), Pd (dppf) Cl ₂ catalyst (0.44 g, 0.6 mmol) and KOAc (5.89 g, 60 mmol) were added to a solution of Sub B 36 (7.99 g, 20 mmol), toluene, bispinacolatodiborone Sub B-3 synthesis method was used to obtain 6.7 g of the product Sub B-36. (Yield: 75%).

(4) Sub  B- 42  synthesis

<Reaction Scheme 21>

Pd (dppf) Cl ₂ catalyst (0.44 g, 0.6 mmol) and KOAc (5.89 g, 60 mmol) were added to a solution of Sub B (42) (13.6 g, 20 mmol), toluene, bispinacolatodiborone Sub B-3 synthesis method was used to obtain 10.9 g of the product Sub B-42. (Yield: 75%).

(5) Sub  B- 46 of  synthesis

<Reaction Formula 22>

Pd (dppf) Cl ₂ catalyst (0.44 g, 0.6 mmol) and KOAc (5.89 g, 60 mmol) were added to a solution of Sub B-3 synthesis method was used to obtain 7.675.32 g of product Sub B-46. (Yield: 74%).

Sub Of B  example

Examples of Sub B are as follows, but are not limited thereto, and their FD-MSs are shown in Table 2 below.

[Table 2]

Product  Synthetic example

The final compound synthesized by the following Reaction Scheme 1 will be described with specific examples.

(One) Product  One- 5 of  synthesis

<Reaction Scheme 23>

Sub B-6 (7.18 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF Dissolved in water, and refluxed for 4 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain 8.47 g of Product 1-5. (Yield: 75%).

(2) Product  One- 38 of  synthesis

<Reaction Scheme 24>

The Sub A1-1 (7.36g, 20mmol) and Sub B-36 (8.93g, 20mmol ), Pd (PPh 3) 4 (0.69g, 0.6mmol), K 2 CO 3 (8.29g, 60mmol) in anhydrous THF and After dissolving in water, 9.39 g of the product 1-38 was obtained using the synthesis method of Product 1-5 above. (Yield: 72%).

(3) Product  One- 56  synthesis

<Reaction Scheme 25>

The Sub A1-10 (8.88g, 20mmol) and Sub B-16 (8.17g, 20mmol ), Pd (PPh 3) 4 (0.69g, 0.6mmol), K 2 CO 3 (8.29g, 60mmol) in anhydrous THF and After dissolving in water, 10.2 g of the product 1-56 was obtained using the synthesis method of Product 1-5 above. (Yield: 74%).

(4) Product  2- 8 of  synthesis

<Reaction Scheme 26>

Sub B-9 (7.16 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 8.45 g of the product 2-8 was obtained using the synthesis method of Product 1-5 above. (Yield: 75%).

(5) Product  2- 49 of  synthesis

<Reaction Scheme 27>

Sub B-13 (8.69 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 10.95 g of the product 2-49 was obtained using the synthesis method of Product 1-5 above. (Yield: 74%).

(6) Product  2- 56  synthesis

<Reaction Scheme 28>

The Sub A2-10 (8.88g, 20mmol) and Sub B-38 (9.45g, 20mmol ), Pd (PPh 3) 4 (0.69g, 0.6mmol), K 2 CO 3 (8.29g, 60mmol) in anhydrous THF and After dissolving in water, 11 g of the product 2-56 was obtained using the synthesis method of Product 1-5 above. (Yield: 73%)

(7) Product  3- 9 of  synthesis

<Reaction Scheme 29>

Sub B-5 (6.64 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 8.06 g of the product 3-9 was obtained using the synthesis method of Product 1-5 described above. (Yield: 75%).

(8) Product  3- Fifty  synthesis

<Reaction Scheme 30>

The Sub A3-4 (11.9g, 20mmol) and Sub B-16 (8.17g, 20mmol ), Pd (PPh 3) 4 (0.69g, 0.6mmol), K 2 CO 3 (8.29g, 60mmol) in anhydrous THF and After dissolving in water, 12.46 g of the product 3-50 was obtained using the method of Product 1-5 described above. (Yield: 74%).

(9) Product  3- 56  synthesis

<Reaction Scheme 31>

Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 6.88 g of the product 3-56 was obtained using the synthesis method of Product 1-5 described above. (Yield: 72%).

(10) Product  Synthesis of 4-3

<Reaction equation 32>

Sub B-3 (5.08 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 6.8 g of the product 4-3 was obtained by using the synthetic method of Product 1-5 described above. (Yield: 74%).

(11) Product  Synthesis of 4-44

<Reaction Scheme 33>

Sub B-46 (10.37 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 10.3 g of the product 4-44 was obtained using the synthesis method of Product 1-5 described above. (Yield: 71%).

(12) Product  Synthesis of 4-52

<Reaction formula 34>

Sub B-12 (9.69 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 11.34 g of the product 4-52 was obtained using the synthesis method of Product 1-5 above. (Yield: 74%).

(13) Product  5- 7's  synthesis

<Reaction Scheme 35>

Sub B-13 (8.69 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 9.23 g of the product 5-7 was obtained using the synthesis method of Product 1-5 described above. (Yield: 72%).

(14) Product  Synthesis of 5-34

<Reaction Formula 36>

Sub B-23 (6.6 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 10.6 g of the product 5-34 was obtained using the synthesis method of Product 1-5 above. (Yield: 74%).

(15) Product  Synthesis of 5-43

(Reaction Scheme 37)

Sub B-41 (10.5 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 12.54 g of the product 5-43 was obtained using the synthesis method of Product 1-5 above. (Yield: 71%).

(16) Product  6- 4 of  synthesis

<Reaction Formula 38>

Sub A6-1 (7.38g, 20mmol) and Sub B-4 (8.17g, 20mmol ), Pd (PPh 3) 4 (0.69g, 0.6mmol), K 2 CO 3 (8.29g, 60mmol) in anhydrous THF and water 9.1 g of the product 6-4 was obtained using the Product synthesis method of Example 3 above. (Yield: 74%).

(17) Product  6- 28 of  synthesis

<Reaction Scheme 39>

Sub A-6 (8.9 g, 20 mmol), Sub B-27 (10.7 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol), K ₂ CO ₃ (8.29 g, 60 mmol) 11.9 g of the product 6-28 was obtained using the Product synthesis method of Example 3 above. (Yield: 73%)

(18) Product  6- 42  synthesis

<Reaction formula 40>

Sub A6-9 (10.42g, 20mmol) and Sub B-40 (11g, 20mmol ), Pd (PPh 3) 4 (0.69g, 0.6mmol), K 2 CO 3 (8.29g, 60mmol) in anhydrous THF and water And 13.45 g of the product 6-42 was obtained using the synthesis method of Product 1-5 described above. (Yield: 74%).

(19) Product  7- 3 of  synthesis

<Reaction Scheme 41>

Sub B-3 (5.1 g, 20 mmol), Pd (PPh ₃ ) ₄ (0.69 g, 0.6 mmol) and K ₂ CO ₃ (8.29 g, 60 mmol) were dissolved in anhydrous THF After dissolving in water, 6.63 g of the product 7-3 was obtained using the synthesis method of Product 1-5 described above. (Yield: 72%).

(20) Product  7- 19's  synthesis

<Reaction Scheme 42>

The Sub A7-1 (7.38g, 20mmol) and Sub B-18 (7.61g, 20mmol ), Pd (PPh 3) 4 (0.69g, 0.6mmol), K 2 CO 3 (8.29g, 60mmol) in anhydrous THF and After dissolving in water, 8.68 g of the product 7-19 was obtained using the synthesis method of Product 1-5 above. (Yield: 74%).

(22) Product  7- 56  synthesis

<Reaction Scheme 43>

The Sub A7-10 (8.9g, 20mmol) and Sub B-38 (9.45g, 20mmol ), Pd (PPh 3) 4 (0.69g, 0.6mmol), K 2 CO 3 (8.29g, 60mmol) in anhydrous THF and After dissolving in water, 10.7 g of the product 7-56 was obtained using the synthesis method of Product 1-5 above. (Yield: 71%).

[Table 3]

Evaluation of manufacturing of organic electric device

[ Experimental Example  1] Blue organic electroluminescent device ( Electron transport layer )

An organic electroluminescent device was fabricated according to a conventional method using a compound obtained through synthesis as an electron transport layer. First, ITO layer (anode) formed on the glass substrate over the N ¹ - (naphthalen-2-yl) -N 4, N 4 -bis (4- (amino naphthalen-2-yl (phenyl)) phenyl) -N 1 - phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer. Subsequently, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as NPD) was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Next, a light emitting layer with a thickness of 30 nm was deposited on the hole transport layer by doping a 9,10-di (naphthalen-2-yl) anthracene host material and a BD-052X (Idemitsu kosan) dopant material at a weight ratio of 93: 7. Then, aluminum (1,1'bisphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum deposited on the light emitting layer to a thickness of 10 nm, Layer, and the compound of the present invention was vacuum deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescence device was manufactured.

[ Comparative Example  One]

An organic electroluminescent device was fabricated in the same manner as in Experimental Example 1, except that the following Comparative Compound 1 was used in place of the compound according to the present invention as the electron transport layer material.

[ Comparative Example  2]

An organic electroluminescent device was fabricated in the same manner as in Experimental Example 1, except that the following compound 2 was used in place of the compound according to the present invention as the electron transport layer material.

[ Comparative Example  3]

An organic electroluminescent device was fabricated in the same manner as in Experimental Example 1, except that the following Comparative Compound 3 was used instead of the compound according to the present invention as the electron transport layer material.

&Lt; Comparative Compound 1 > Alq₃ &Lt; Comparative Compound 2 > &Lt; Comparative Compound 3 >

Electroluminescence (EL) characteristics were measured by photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Experimental Example 1 and Comparative Examples 1 to 3, and 5000 cd / The T95 lifetime was measured using a lifetime measuring instrument manufactured by McAfee Inc. at a reference brightness of m ² . Table 4 shows the electronic characteristics of the organic electroluminescence devices of Experimental Example 1 (Examples 1 to 392) and Comparative Examples 1 to 3.

[Table 4]

As can be seen from the results of Table 4, the organic electroluminescence device (OLED) using the compounds of the invention are used as electron transport materials well Alq ₃ Comparative Compound a low driving voltage and high efficiency, and higher than the one used from existing Respectively.

This is the case of a dopant Ir (ppy) of the present invention, while indicate _three of the Alq ₃ used as the electron transport layer than the T ₁ value (2.4 eV) T ₁ value (2.0 eV) is low, the compound used in the light emitting layer, Ir (ppy) ₃ the T ₁ value shows a generally high T ₁ value (2.5 eV ~ 2.6 eV) than that (2.4 eV), Thus the compounds according to the invention to the host (host) having a high T ₁ value than the emission layer dopant (dopant) It is possible to transfer electrons easily and quickly than the comparative compound 1, and as a result, it is judged that the driving voltage is lowered. In addition, since electrons can be easily transferred into the light emitting layer, the charge balance in the light emitting layer is improved and the efficiency and lifetime are increased.

Specifically, comparing the results of organic electroluminescent devices using the compounds of the present invention with those of the comparative compounds, the inventive compounds are superior to the comparative compounds, in particular, the comparative compounds 2 and 3 are phenanthrene ) Type, but it shows different results depending on the kind of substituent, the presence or absence of N, and the number.

Comparing the results of the device of Comparison Compound 2 where X ¹ to X ⁴ are all carbon and X ² and X ⁴ are N based on Formula 1 of the present invention, , High efficiency and long life.

It can be explained that Comparative Compound 3 has electron mobility faster than Comparative Compound 2 due to the addition of a nitrogen atom having an electron transfer (ET) tendency. When the organic electroluminescent device is driven, holes having a higher mobility than electrons act as majority carriers, and holes are accumulated in the light emitting layer, which adversely affects the device results. Therefore, in order to control the balance of holes and electrons, materials of electron transport layer having fast electron mobility are required.

Therefore, the comparative compound 3 having a higher electron mobility than that of the comparative compound 2 was found to exhibit more excellent results. As a result of the inventive compound, the compound of 5-1 to 7-56 in which two N's are substituted than the compounds 1-1 to 4-56 in which one of N ¹ is substituted in X ¹ to X ⁴ is It can be confirmed that it shows excellent device characteristics.

In addition, there are substituted more than N of the X ¹ to X ⁴ based one the general formula (I) of the present invention, R ¹ and R, and ² are all substituted one or more of the comparative compound 3 and X ¹ to X ⁴ hydrogen N, R ¹ and R ² The compounds of the present invention have the lowest driving voltage, the highest efficiency, and the highest lifetime in comparison with the compound of the present invention in which the aryl group is substituted. When at least one of R ¹ and R ² is substituted with an aryl group, the HOMO value is similar but the LUMO value is increased, resulting in a wider band gap. As a result, It seems to be possible to display the low driving voltage and high efficiency by making the mobility fast. Further, when the compound of the present invention in which at least one aryl group is substituted with the compound of Comparative Example 3 in which R ¹ and R ² are all hydrogen is used, the thermal stability is further improved, and the compound exhibits a longer lifetime.

While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the same should be construed as being included in the scope of the present invention.

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

Claims (8)

A compound represented by the following formula (1).
&Lt; Formula 1 >

[In the above formula (1)
L is a single bond, a C ₆ to C ₆₀ arylene group, or a fluorenylene group,
R ¹ and R ⁴ are independently hydrogen or a C ₆ to C ₆₀ aryl group, R ² is a C ₆ to C ₆₀ aryl group, R ³ is a C ₆ to C ₆₀ aryl group, or O, N , A C ₂ to C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of S, Si and P,
At least one of X ¹ to X ⁴ is N and the others are independently of each other CH, CR or N, wherein R is a C ₆ to C ₆₀ aryl group, a fluorenyl group, O, N, S, Si and P at least one hetero atom C ₂ ~ of the C ₆₀ heterocyclic ring containing group, C ₃ ~ group fused ring of an aromatic ring of C ₆₀ of aliphatic rings and _{C 6 ~ C 60, C 1} ~ alkyl group of C _50, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl, C ₁ ~ C ₃₀ alkoxy group and a C ₆ ~ is selected from the group consisting of aryloxy groups of C ₃₀ for,
The case where L is an arylene group or a fluorenylene group and the case where R, R ¹ , R ² and R ³ are independently of each other an aryl group and the case where R and R ³ are independently a heterocyclic ring and the case where R is a fluorene A fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group or an aryloxy group, each of these may be independently selected from the group consisting of deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ to C ₂₀ ; A C ₁ to C ₂₀ alkoxyl group; An alkyl group having ₁ to ₂₀ carbon atoms; An alkenyl group having ₂ to ₂₀ carbon atoms; An alkynyl group having ₂ to ₂₀ carbon atoms; A C ₆ to C ₂₀ aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A heterocyclic group of C ₂ ~ C _20; A C ₃ to C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ to C ₂₀ ; And an arylalkenyl group having from ₈ to ₂₀ carbon atoms. The method according to claim 1,
(1) is one of the following formulas (2) to (8).
&Lt; Formula 2 >< EMI ID =

&Lt; Formula 6 &gt;&lt; EMI ID =

(In the above formulas (2) to (8), L, R ¹ to R ⁴ are the same as defined in claim 1) The method according to claim 1,
The compound of formula (I) is one of the following compounds.

A first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode,
Wherein the organic material layer contains the compound of any one of claims 1 to 3. 5. The method of claim 4,
The compound is contained in the electron injection layer of the organic material layer,
Wherein the compound is a homologous compound or two or more different kinds of compounds. 5. The method of claim 4,
Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device including the organic electroluminescent device of claim 4; And
And a control unit for driving the display device. 8. The method of claim 7,
Wherein the organic electroluminescent device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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