KR20130040133A - Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof - Google Patents

Abstract

PURPOSE: A compound for an organic electronic element and an electronic device thereof are provided to lower driving voltage of the organic electronic element and to largely improve light emitting efficiency, lifetime, and color purity. CONSTITUTION: A compound is denoted by chemical formula 1. An organic electronic element comprises a first electrode, one or more organic layers containing the compound, and a second electrode. The organic layer includes a light emitting layer and/or a hole transport layer. One or more layers among the light emitting layer and the hole transport layer are formed of the compound. An electronic device comprises a display device containing the organic electronic element, and a control unit which drives the display device.

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 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.

Materials used as the organic material layer in the organic electric element 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 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 the triplet excited state of electrons . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

In particular, various studies have been conducted on organic materials inserted into the hole transport layer or the buffer layer for excellent life characteristics of the organic electric device, and for this purpose, a thin film after deposition is provided while providing high hole transport characteristics from the anode to the organic layer. There is a need for a hole injection layer material having high uniformity and low crystallinity in forming.

Delays penetration of metal oxide 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, and stable properties for Joule heating generated when driving the device, that is, high glass transition temperature. There is a need for development of a hole injection layer material having In addition, the low glass transition temperature of the hole transport layer material has been reported to have a significant effect on the device life, depending on the characteristics of the uniformity of the surface of the thin film when driving the device. In addition, the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. In order to increase the light emitting efficiency through the light emitting material, a host / dopant system may be used. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In order to fully exhibit the excellent characteristics of the above-described organic electroluminescent device, a material 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, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.

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

According to one aspect of the present invention, the present invention provides a compound represented by the following formula.

According to another aspect of the invention, the present invention provides an organic electric device comprising the formula (1) and an electronic device using the same.

By using the novel compound according to the present invention, the luminous efficiency, lifetime and color purity can be greatly improved while lowering the driving voltage of the organic electric element.

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

Hereinafter, some embodiments of the present invention will be described in detail through exemplary 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 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 herein, the term "halo" or "halogen" includes fluorine, chlorine, bromine, and iodine unless otherwise noted.

The term "alkyl" or "alkyl group ", as used herein, unless otherwise specified, has from 1 to 60 carbon atoms, 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 specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxy group" as used in the present invention has, unless otherwise stated, 1 to 60 carbon atoms, but is not limited thereto.

The terms "aryl group" and "arylene group ", as used in the present invention, each have 6 to 60 carbon atoms, but are not limited thereto.

In the present invention, an aryl group or an arylene group means an aromatic group having a single ring or a heterocyclic ring, and the neighboring substituent includes an aromatic ring formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirobifluorene group.

As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 3 to 60 carbon atoms each containing at least one heteroatom, But includes a single ring as well as a heterocyclic ring and may be formed by bonding adjacent groups.

The term " heterocycloalkyl ", "heterocyclic group ", as used herein, unless otherwise indicated, includes one or more heteroatoms, has from 2 to 60 carbon atoms, , And neighboring groups may be combined with each other. Furthermore, the "heterocyclic group" may mean an alicyclic group and / or an aromatic group including a hetero atom.

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 an "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise indicated, the term "saturated or unsaturated ring" as used herein refers to a saturated or unsaturated aliphatic ring or an aromatic ring or hetero ring having 6 to 60 carbon atoms.

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

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 alkoxy group, C ₁ ~ C ₂₀ alkyl amine group of _20, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ arylalkenyl group, a silane group, a boron of Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a cyano group, a germanium group, and a C ₅ to C ₂₀ heterocyclic group.

1 is an exemplary view of an organic electric 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, ) Having an organic compound layer containing a compound represented by the general formula (1). In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer 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. 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.

Also, although not shown, the organic electroluminescent device according to the present invention may further include a protective 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 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 according to the present invention may be used as a host material of the light emitting layer 150 or a material for forming the hole transport layer 140.

On the other hand, the organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) 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 can be formed using a variety of polymer materials by a solution process other than a vapor deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, It can be made of a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.

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

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

Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. 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 contained in the organic material layer of the organic electric device according to an aspect of the present invention will be described in detail.

An organic electric device according to an aspect of the present invention includes an anode, a cathode, and an organic material layer formed between the anode and the cathode. In this case, the emission layer may be formed of a compound represented by the following Chemical Formula 1.

≪ Formula 1 >

In Formula 1, A ring is C ₆ ~ C ₆₀ A single or polycyclic aromatic or heterocyclic ring, n is 1 or 2. That is, the A ring may be an aromatic ring such as benzene ring, biphenyl, naphthyl, phenanthrene or the like, or may be a hetero ring such as a carbazolyl group or a pyrrole group. In the case of heterocycles, at least 7 carbon atoms are preferred.

In Formula 1, Y may have a substituent definition depending on n. For example, when n is 1, since Y is monovalent, hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ C ₆₀ aryl group, fluorenyl group It may be selected from a monovalent substituent group consisting of a C ₂ ~ C ₆₀ heterocyclic group, a C ₁ ~ C ₃₀ alkoxy group, a C ₆ ~ C ₃₀ aryloxy group and a C ₁ ~ C ₅₀ alkyl group. And, when n is 2, Y is a direct bond (ie, absent), C ₆ ~ C ₆₀ arylene group, fluorenylene group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ alicyclic It may be selected from the group of divalent substituents consisting of this fused ring, a C ₂ -C ₆₀ heterocyclic group or a divalent aliphatic hydrocarbon group.

R ₁ to R ₁₁ are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ heterocyclic group, C ₁ ~ C ₃₀ Alkoxy group, C ₆ ~ C _{30 It} may be selected from the group consisting of aryloxy group and C ₁ ~ C ₅₀ Alkyl group, X is S, SO or SO ₂ to be.

In this case, in -LN (Ar ₁ ) (Ar ₂ ), L is a direct bond (that is, absent), C ₆ ~ C ₆₀ arylene group, fluorenylene group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ of aliphatic and may be selected from the group consisting of fused rings, C ₂ ~ C ₆₀ heterocyclic group or a divalent aliphatic hydrocarbon group,

Ar ₁ and Ar ₂ are each independently of the C ₆ ~ C ₆₀ aryl group, C ₂ ~ C ₆₀ heterocyclic group, fluorenyl group, C ₁ ~ C ₃₀ alkoxy group, C ₆ ~ C ₃₀ aryloxy group And it is selected from the group consisting of C ₁ ~ C ₅₀ Alkyl group.

Meanwhile, Y, R ₁ to R ₁₁ , L, Ar _1, and Ar ₂ may be further substituted with specific substituents.

By way of example, when Y, R ₁ to R ₁₁ , Ar ₁ and Ar ₂ is a C ₆ ~ C ₆₀ aryl group, and when Y, R ₁ to R ₁₁ , Ar ₁ and Ar ₂ is a fluorenyl group and In the case of the arylene group of the Y and L, and the Y and L is a fluorenylene group, these are deuterium, halogen, silane group, boron group, germanium group, C ₁ ~ C ₂₀ Alkylthio group, C ₆ ~ C ₂₀ arylthio group, C ₁ -C ₂₀ alkoxy group, -N (Ar ₁ ) (Ar ₂ ), C ₁ -C ₂₀ alkyl group, C7-C20 arylalkyl group, C ₂ -C ₂₀ alkenyl group , C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium and C ₂ ~ C ₂₀ heterocyclic ring It may be substituted with one or more substituents selected from the group consisting of groups.

In addition, the C ₆ ~ C ₆₀ heterocyclic group of the Y, R ₁ to R ₁₁ , L, Ar ₁ and Ar ₂ includes at least one hetero atom of O, N, S, Si and P, deuterium, halogen Group, -N (Ar ₁ ) (Ar ₂ ), C ₁ -C ₂₀ alkyl group, C ₇ -C ₂₀ arylalkyl group, C ₂ -C ₂₀ alkenyl group, C ₈ -C ₂₀ arylalkenyl group, C It may be substituted with one or more substituents selected from the group consisting of ₁ to C ₂₀ alkoxy group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, a nitrile group and an acetylene group.

Further, the C ₁ to C ₃₀ alkoxy group and the C ₆ to C ₃₀ aryloxy group of the Y, R ₁ to R ₁₁ , Ar ₁ and Ar ₂ may be deuterium, halogen, amino, nitrile, nitro or C _1. ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, a C ₆ ~ C substituted with deuterium It may be substituted with one or more substituents selected from the group consisting of an aryl group of _{20 and} a heterocyclic group of C ₂ ~ C ₆₀ .

In addition, the C ₁ to C ₅₀ alkyl group of Y, R ₁ to R ₁₁ , r _1, and Ar ₂ may be C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ alkoxy group, C ₆ to C ₂₀ aryl A C ₆ to C ₂₀ aryl group, a C ₇ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₂ to C ₂₀ heterocyclic group, a nitrile group and an acetylene group It may be substituted with one or more substituents selected from the group.

Specifically, Formula 1 may be represented by one of the following formula. Formula 2 corresponds to the case of n = 1 in Formula 1, and Formula 3 corresponds to the case of n = 2. In addition, Formula 4 corresponds to the case where n = 1 in Formula 1 and Y is -L-N (Ar1) (Ar2) among monovalent substituents.

<Formula 2>

<Formula 3>

&Lt; Formula 4 >

In Formula 2 to Formula 4, A ring, R ₁ ~ R ₁₁ and X are as defined in formula (1). In Formula 2, Y is a monovalent substituent group in the definition of Y in Formula 1, that is, Y in Formula 2 is hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ Monovalent consisting of C ₆₀ aryl group, fluorenyl group, C ₂ -C ₆₀ heterocyclic group, C ₁ -C ₃₀ alkoxy group, C ₆ -C ₃₀ aryloxy group and C ₁ -C ₅₀ alkyl group It may be selected from the group of substituents. On the other hand, in Formula 3, Y is a direct bond or a divalent substituent group in the Y definition of Formula 1, that is, C ₆ ~ C ₆₀ arylene group, fluorenylene group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ It may be selected from the group of divalent substituents consisting of an alicyclic fused ring, a C ₂ ~ C ₆₀ heterocyclic group and a divalent aliphatic hydrocarbon group. In addition, in Chemical Formula 4, L, Ar ₁ and Ar ₂ are the same as defined in Chemical Formula 1.

In addition, when A ring is a benzene ring, Formula 1 may be represented by one of the following Formulas 5 to 7.

&Lt; Formula 5 >

(6)

&Lt; Formula 7 >

In Chemical Formulas 5 to 7, R ₁ to R ₈ and X are the same as defined in Chemical Formula 1. In addition, Y in Formula 5 may be selected from the group of monovalent substituents in the Y definition of Formula 1, Y in Formula 6 may be a direct bond, or may be selected from a divalent substituent group in the Y definition of Formula 1, Formula 7 L, Ar ₁ and Ar ₂ are as defined in formula (1).

More specifically, Formula 1 may be one of the following compounds, but is not limited to these compounds, any compound satisfying Formula 1 will belong to the present invention.

Hereinafter, the synthesis examples of the compounds represented by the general formula (1) of the present invention and the production examples of the organic electric device will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

In exemplary embodiments, Chemical Formula 1 may be synthesized by the following Chemical Formula 1.

<Reaction Scheme 1>

In Scheme 1, Sub 1-6 may be synthesized by Scheme 2 below.

<Reaction Scheme 2>

Sub 1-1 to Sub 1-6 of Scheme 2 may be synthesized by the following synthesis method, but is not limited thereto.

Sub 1-1 Synthesis

After dissolving Phenanthrene (35.65 g, 200 mmol) in 600 mL of methylene chloride, 0.05 equivalent of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) were slowly added, followed by stirring at room temperature for 24 hours. . After the reaction was completed, 300 mL of 5% HCl was added, followed by 300 mL of water to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. Thereafter, the resultant organic material was recrystallized from a silicagel column to obtain 38.57 g (75%) of Sub 1-1.

Sub 1-2 synthesis

Sub 1-1 (36.0 g, 140 mmol) obtained in the above synthesis was dissolved in 980 mL of DMF, followed by bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol), KOAc (41.3 g, 420 mmol) was added sequentially, followed by stirring for 24 hours to synthesize the borate compound. The obtained compound was separated through a silica gel column and recrystallized, and then the borate compound was 29.81 g (70%) of Sub 1-2. Get

Sub 1-3 Synthesis

After dissolving 1 equivalent of Sub 1-2 obtained in the synthesis and 1 equivalent of 2-bromothioanisole in 200 ml of THF, 1.1 equivalent of Tetrakis (triphenylphosphine) palladium and 2M aqueous sodium carbonate solution were added thereto, and the mixture was stirred at 70 ° C for 18 hours. After the reaction was completed, extracted with diethyl ehter and water, the organic layer was dried, silicagel column and recrystallization to obtain Sub 1-3 80%.

Sub 1-4 Synthesis

Sub 1-3 was dissolved in dichloromethane, 30% aqueous hydroxyperoxide solution and acetic acid were added, followed by stirring at 30 ° C. for 4 hours. After the reaction was completed, extracted with chloroform and water, the organic layer was dried, silicagel column and recrystallization to obtain Sub 1-4 76%.

Sub 1-5 Synthesis

Add triflic acid to Sub 1-4 and stir at room temperature for 72 hours. After the reaction was completed, diethyl ehter was added, and the resulting white solid precipitate was filtered and dried to obtain 78% of Sub 1-5.

Sub 1-6 Synthesis

Sub 1-5 was dissolved in 600 mL of methylene chloride, and then 0.05 equivalent of BPO (Benzoyl peroxide) and NBS (N-bromosuccinimide) (35.60 g, 200 mmol) were added slowly, followed by stirring at room temperature for 24 hours. After the reaction was completed, 300 mL of 5% HCl was added, followed by 300 mL of water to remove residual NBS, and extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was silicagel column and recrystallized to obtain Sub 1-6 78%.

Meanwhile, Sub 2 in Scheme 1 may be one of the following compounds, but is not limited thereto.

The FD-MS values of Sub 2-1 to Sub 2-24 are shown in Table 1 below.

compound FD-MS compound FD-MS Sub 2-1 m / z = 122.05 (C ₆ H ₇ BO ₂ = 121.93) Sub 2-2 m / z = 172.07 (C ₁₀ H ₉ BO ₂ = 171.99) Sub 2-3 m / z = 172.07 (C ₁₀ H ₉ BO ₂ = 171.99) Sub 2-4 m / z = 222.09 (C ₁₄ H ₁₁ BO ₂ = 222.05) Sub 2-5 m / z = 222.09 (C ₁₄ H ₁₁ BO ₂ = 222.05) Sub 2-6 m / z = 272.10 (C ₁₈ H ₁₃ BO ₂ = 272.11) Sub 2-7 m / z = 228.04 (C ₁₂ H ₉ BO ₂ S = 228.07) Sub 2-8 m / z = 238.12 (C ₁₅ H ₁₅ BO ₂ = 238.09) Sub 2-9 m / z = 198.09 (C ₁₂ H ₁₁ BO ₂ = 198.03) Sub 2-10 m / z = 248.10 (C ₁₆ H ₁₃ BO ₂ = 248.08) Sub 2-11 m / z = 122.05 (C ₆ H ₇ BO ₂ = 121.93) Sub 2-12 m / z = 298.12 (C ₂₀ H ₁₅ BO ₂ = 298.14) Sub 2-13 m / z = 298.12 (C ₂₀ H ₁₅ BO ₂ = 298.14) Sub 2-14 m / z = 348.13 (C ₂₄ H ₁₇ BO ₂ = 348.20) Sub 2-15 m / z = 304.07 (C ₁₈ H ₁₃ BO ₂ S = 304.17) Sub 2-16 m / z = 314.15 (C ₂₁ H ₁₉ BO ₂ = 314.19) Sub 2-17 m / z = 248.10 (C ₁₆ H ₁₃ BO ₂ = 248.08) Sub 2-18 m / z = 298.12 (C ₂₀ H ₁₅ BO ₂ = 298.14) Sub 2-19 m / z = 298.12 (C ₂₀ H ₁₅ BO ₂ = 298.14) Sub 2-20 m / z = 348.13 (C ₂₄ H ₁₇ BO ₂ = 348.20) Sub 2-21 m / z = 348.13 (C ₂₄ H ₁₇ BO ₂ = 348.20) Sub 2-22 m / z = 398.15 (C ₂₈ H ₁₉ BO ₂ = 398.26) Sub 2-23 m / z = 354.09 (C ₂₂ H ₁₅ BO ₂ S = 354.23) Sub 2-24 m / z = 364.16 (C ₂₅ H ₂₁ BO ₂ = 364.24)

< Example  1> final compound ( Product  Synthesis example of 1)

Compounds of Sub 1-6 (1 equiv), Sub 2 compounds (1 equiv), Pd ₂ (dba) ₃ (0.03-0.5 mmol), PPh ₃ (0.1 equiv), NaO t -Bu (3 equiv. ), add toluene (10.5 mL / 1 mmol) and proceed with the reaction at 100 ° C. After the reaction was completed, the mixture was extracted with ether and water, and the organic layer was dried over MgSO ₄ , concentrated, and the resulting organic material was silicagel column and recrystallized. FD-MS of the resulting final compound is shown in Table 2 below.

compound FD-MS compound FD-MS 2-1 m / z = 360.10 (C ₂₆ H ₁₆ S = 360.47) 2-2 m / z = 410.11 (C ₃₀ H ₁₈ S = 410.53) 2-3 m / z = 410.11 (C ₃₀ H ₁₈ S = 410.53) 2-4 m / z = 460.13 (C ₃₄ H ₂₀ S = 460.59) 2-5 m / z = 460.13 (C ₃₄ H ₂₀ S = 460.59) 2-6 m / z = 510.14 (C ₃₈ H ₂₂ S = 510.65) 2-7 m / z = 466.08 (C ₃₂ H ₁₈ S ₂ = 466.62) 2-8 m / z = 476.16 (C ₃₅ H ₂₄ S = 476.63) 2-9 m / z = 452.12 (C ₃₂ H ₂₀ OS = 452.57) 2-10 m / z = 502.14 (C ₃₆ H ₂₂ OS = 502.62) 2-11 m / z = 502.14 (C ₃₆ H ₂₂ OS = 502.62) 2-12 m / z = 536.16 (C ₄₀ H ₂₄ S = 536.68) 2-13 m / z = 536.16 (C ₄₀ H ₂₄ S = 536.68) 2-14 m / z = 586.18 (C ₄₄ H ₂₆ S = 586.74) 2-15 m / z = 542.12 (C ₃₈ H ₂₂ S ₂ = 542.71) 2-16 m / z = 552.19 (C ₄₁ H ₂₈ S = 552.73) 2-17 m / z = 518.13 (C ₃₆ H ₂₂ O ₂ S = 518.62) 2-18 m / z = 568.15 (C ₄₀ H ₂₄ O ₂ S = 568.68) 2-19 m / z = 568.15 (C ₄₀ H ₂₄ O ₂ S = 568.68) 2-20 m / z = 586..18 (C ₄₄ H ₂₆ S = 586.74) 2-21 m / z = 586.18 (C ₄₄ H ₂₆ S = 586.74) 2-22 m / z = 636.19 (C ₄₈ H ₂₈ S = 636.80) 2-23 m / z = 592.13 (C ₄₂ H ₂₄ S ₂ = 592.77) 2-24 m / z = 602.21 (C ₄₅ H ₃₀ S = 602.78) 2-25 m / z = 376.09 (C ₂₆ H ₁₆ OS = 376.47) 2-26 m / z = 426.11 (C ₃₀ H ₁₈ OS = 426.53) 2-27 m / z = 426.11 (C ₃₀ H ₁₈ OS = 426.53) 2-28 m / z = 460.13 (C ₃₄ H ₂₀ S = 460.59) 2-29 m / z = 460.13 (C ₃₄ H ₂₀ S = 460.59) 2-30 m / z = 510.14 (C ₃₈ H ₂₂ S = 510.65) 2-31 m / z = 466.08 (C ₃₂ H ₁₈ S ₂ = 466.62) 2-32 m / z = 476.16 (C ₃₅ H ₂₄ S = 476.63) 2-33 m / z = 468.12 (C ₃₂ H ₂₀ O ₂ S = 468.57) 2-34 m / z = 518.13 (C ₃₆ H ₂₂ O ₂ S = 518.62) 2-35 m / z = 518.13 (C ₃₆ H ₂₂ O ₂ S = 518.62) 2-36 m / z = 536.16 (C ₄₀ H ₂₄ S = 536.68) 2-37 m / z = 536.16 (C ₄₀ H ₂₄ S = 536.68) 2-38 m / z = 586.18 (C ₄₄ H ₂₆ S = 586.74) 2-39 m / z = 542.12 (C ₃₈ H ₂₂ S ₂ = 542.71) 2-40 m / z = 552.19 (C ₄₁ H ₂₈ S = 552.73) 2-41 m / z = 502.14 (C ₃₆ H ₂₂ OS = 502.62) 2-42 m / z = 552.15 (C ₄₀ H ₂₄ OS = 552.68) 2-43 m / z = 552.15 (C ₄₀ H ₂₄ OS = 552.68) 2-44 m / z = 586.18 (C ₄₄ H ₂₆ S = 586.74) 2-45 m / z = 586.18 (C ₄₄ H ₂₆ S = 586.74) 2-46 m / z = 636.19 (C ₄₈ H ₂₈ S = 636.80) 2-47 m / z = 624.12 (C ₄₂ H ₂₄ O ₂ S ₂ = 624.77) 2-48 m / z = 634.20 (C ₄₅ H ₃₀ O ₂ S = 634.78) 2-49 m / z = 642.15 (C ₄₆ H ₂₆ S ₂ = 642.83) 2-50 m / z = 692.16 (C ₅₀ H ₂₈ S ₂ = 692.89) 2-51 m / z = 692.16 (C ₅₀ H ₂₈ S ₂ = 692.89)

As another example, the final compound of the present invention can be prepared by the following scheme 3.

<Reaction Scheme 3>

In Scheme 3, Sub 3 may be one of the following compounds, but is not necessarily limited thereto.

The FD-MS of Sub 3-1 to Sub 3-66 is shown in Table 3 below.

compound FD-MS compound FD-MS Sub 3-1 m / z = 166.09 (C ₁₂ H ₁₁ N = 169.22) Sub 3-2 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub 3-3 m / z = 219.10 (C ₁₆ H ₁₃ N = 219.28) Sub 3-4 m / z = 245.12 (C ₁₈ H ₁₅ N = 245.32) Sub 3-5 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub 3-6 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub 3-7 m / z = 319.14 (C ₂₄ H ₁₇ N = 319.40) Sub 3-8 m / z = 275.08 (C ₁₈ H ₁₃ NS = 275.37) Sub 3-9 m / z = 187.08 (C ₁₂ H ₁₀ FN = 187.21) Sub 3-10 m / z = 225.15 (C ₁₆ H ₁₉ N = 225.33) Sub 3-11 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub 3-12 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub 3-13 m / z = 319.14 (C ₂₄ H ₁₇ N = 319.40) Sub 3-14 m / z = 319.14 (C ₂₄ H ₁₇ N = 319.40) Sub 3-15 m / z = 369.15 (C ₂₈ H ₁₉ N = 369.46) Sub 3-16 m / z = 325.09 (C ₂₂ H ₁₅ NS = 325.43) Sub 3-17 m / z = 237.10 (C ₁₆ H ₁₂ FN = 237.27) Sub 3-18 m / z = 275.17 (C ₂₀ H ₂₁ N = 275.39) Sub 3-19 m / z = 269.12 (C ₂₀ H ₁₅ N = 269.34) Sub 3-20 m / z = 295.14 (C ₂₂ H ₁₇ N = 295.38) Sub 3-21 m / z = 319.14 (C ₂₄ H ₁₇ N = 319.40) Sub 3-22 m / z = 319.14 (C ₂₄ H ₁₇ N = 319.40) Sub 3-23 m / z = 369.15 (C ₂₈ H ₁₉ N = 369.46) Sub 3-24 m / z = 325.09 (C ₂₂ H ₁₅ NS = 325.43) Sub 3-25 m / z = 237.10 (C ₁₆ H ₁₂ FN = 237.27) Sub 3-26 m / z = 275.17 (C ₂₀ H ₂₁ N = 275.39) Sub 3-27 m / z = 321.15 (C ₂₄ H ₁₉ N = 321.41) Sub 3-28 m / z = 345.15 (C ₂₆ H ₁₉ N = 345.44) Sub 3-29 m / z = 345.15 (C ₂₆ H ₁₉ N = 345.44) Sub 3-30 m / z = 395.17 (C ₃₀ H ₂₁ N = 395.49) Sub 3-31 m / z = 351.11 (C ₂₄ H ₁₇ NS = 351.46) Sub 3-32 m / z = 263.11 (C ₁₈ H ₁₄ FN = 263.31) Sub 3-33 m / z = 301.18 (C ₂₂ H ₂₃ N = 301.42) Sub 3-34 m / z = 369.15 (C ₂₈ H ₁₉ N = 369.46) Sub 3-35 m / z = 369.15 (C ₂₈ H ₁₉ N = 369.46) Sub 3-36 m / z = 419.17 (C ₃₂ H ₂₁ N = 419.52) Sub 3-37 m / z = 375.11 (C ₂₆ H ₁₇ NS = 375.48) Sub 3-38 m / z = 287.11 (C ₂₀ H ₁₄ FN = 287.33) Sub 3-39 m / z = 325.18 (C ₂₄ H ₂₃ N = 325.45) Sub 3-40 m / z = 369.15 (C ₂₈ H ₁₉ N = 369.46) Sub 3-41 m / z = 419.17 (C ₃₂ H ₂₁ N = 419.52) Sub 3-42 m / z = 375.11 (C ₂₆ H ₁₇ NS = 375.48) Sub 3-43 m / z = 287.11 (C ₂₀ H ₁₄ FN = 287.33) Sub 3-44 m / z = 325.18 (C ₂₄ H ₂₃ N = 325.45) Sub 3-45 m / z = 469.18 (C ₃₆ H ₂₃ N = 469.57) Sub 3-46 m / z = 425.12 (C ₃₀ H ₁₉ NS = 425.54) Sub 3-47 m / z = 337.13 (C ₂₄ H ₁₆ FN = 337.39) Sub 3-48 m / z = 375.20 (C ₂₈ H ₂₅ N = 375.50) Sub 3-49 m / z = 381.06 (C ₂₄ H ₁₅ NS ₂ = 381.51) Sub 3-50 m / z = 293.07 (C ₁₈ H ₁₂ FNS = 293.36) Sub 3-51 m / z = 331.14 (C ₂₂ H ₂₁ NS = 331.47) Sub 3-52 m / z = 205.07 (C ₁₂ H ₉ F ₂ N = 205.20) Sub 3-53 m / z = 243.14 (C ₁₆ H ₁₈ FN = 243.32) Sub 3-54 m / z = 243.14 (C ₁₆ H ₁₈ FN = 243.32) Sub 3-55 m / z = 281.21 (C ₂₀ H ₂₇ N = 281.44) Sub 3-56 m / z = 285.15 (C ₂₁ H ₁₉ N = 285.38) Sub 3-57 m / z = 335.17 (C ₂₅ H ₂₁ N = 335.44) Sub 3-58 m / z = 335.17 (C ₂₅ H ₂₁ N = 335.44) Sub 3-59 m / z = 361.18 (C ₂₇ H ₂₃ N = 361.48) Sub 3-60 m / z = 385.18 (C ₂₉ H ₂₃ N = 385.50) Sub 3-61 m / z = 385.18 (C ₂₉ H ₂₃ N = 385.50) Sub 3-62 m / z = 435.20 (C ₃₃ H ₂₅ N = 435.56) Sub 3-63 m / z = 391.14 (C ₂₇ H ₂₁ NS = 391.53) Sub 3-64 m / z = 303.14 (C ₂₁ H ₁₈ FN = 303.37) Sub 3-65 m / z = 341.21 (C ₂₅ H ₂₇ N = 341.49) Sub 3-66 m / z = 401.21 (C ₃₀ H ₂₇ N = 401.54)

< Example  2> final compound ( Product  2) Synthesis Example

Sub 1-7 compound (1 equivalent) was added to a round bottom flask, and the amine compound Sub 3 (1.1 equivalent), Pd (PPh ₃ ) ₄ (0.03 to 0.05 equivalent), NaOH (3 equivalent), THF (3 mL / 1 mmol), water (1.5 mL / 1 mmol) is added. Thereafter, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was recrystallized from a silicagel column. FD-MS of the final compound thus synthesized is shown in Table 4 below.

compound FD-MS compound FD-MS 3-1 m / z = 451.14 (C ₃₂ H ₂₁ NS = 451.58) 3-2 m / z = 501.16 (C ₃₆ H ₂₃ NS = 501.64) 3-3 m / z = 501.16 (C ₃₆ H ₂₃ NS = 501.64) 3-4 m / z = 527.17 (C ₃₈ H ₂₅ NS = 527.68) 3-5 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-6 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-7 m / z = 601.19 (C ₄₄ H ₂₇ NS = 601.76) 3-8 m / z = 557.13 (C ₃₈ H ₂₃ NS ₂ = 557.73) 3-9 m / z = 469.13 (C ₃₂ H ₂₀ FNS = 469.57) 3-10 m / z = 507.20 (C ₃₆ H ₂₉ NS = 507.69) 3-11 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-12 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-13 m / z = 601.19 (C ₄₄ H ₂₇ NS = 601.76) 3-14 m / z = 601.19 (C ₄₄ H ₂₇ NS = 601.76) 3-15 m / z = 651.20 (C ₄₈ H ₂₉ NS = 651.82) 3-16 m / z = 607.14 (C ₄₂ H ₂₅ NS ₂ = 607.78) 3-17 m / z = 519.15 (C ₃₆ H ₂₂ FNS = 519.63) 3-18 m / z = 557.22 (C ₄₀ H ₃₁ NS = 557.75) 3-19 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-20 m / z = 577.19 (C ₄₂ H ₂₇ NS = 577.74) 3-21 m / z = 601.19 (C ₄₄ H ₂₇ NS = 601.76) 3-22 m / z = 601.19 (C ₄₄ H ₂₇ NS = 601.76) 3-23 m / z = 651.20 (C ₄₈ H ₂₉ NS = 651.82) 3-24 m / z = 607.14 (C ₄₂ H ₂₅ NS ₂ = 607.78) 3-25 m / z = 519.15 (C ₃₆ H ₂₂ FNS = 519.63) 3-26 m / z = 557.22 (C ₄₀ H ₃₁ NS = 557.75) 3-27 m / z = 603.20 (C ₄₄ H ₂₉ NS = 603.77) 3-28 m / z = 627.20 (C ₄₆ H ₂₉ NS = 627.79) 3-29 m / z = 627.20 (C ₄₆ H ₂₉ NS = 627.79) 3-30 m / z = 677.22 (C ₅₀ H ₃₁ NS = 677.85) 3-31 m / z = 633.16 (C ₄₄ H ₂₇ NS ₂ = 633.82) 3-32 m / z = 545.16 (C ₃₈ H ₂₄ FNS = 545.67) 3-33 m / z = 583.23 (C ₄₂ H ₃₃ NS = 583.78) 3-34 m / z = 651.20 (C ₄₈ H ₂₉ NS = 651.82) 3-35 m / z = 651.20 (C ₄₈ H ₂₉ NS = 651.82) 3-36 m / z = 701.22 (C ₅₂ H ₃₁ NS = 701.87) 3-37 m / z = 657.16 (C ₄₆ H ₂₇ NS ₂ = 657.84) 3-38 m / z = 569.16 (C ₄₀ H ₂₄ FNS = 569.69) 3-39 m / z = 607.23 (C ₄₄ H ₃₃ NS = 607.80) 3-40 m / z = 651.20 (C ₄₈ H ₂₉ NS = 651.82) 3-41 m / z = 701.22 (C ₅₂ H ₃₁ NS = 701.87) 3-42 m / z = 657.16 (C ₄₆ H ₂₇ NS ₂ = 657.84) 3-43 m / z = 569.16 (C ₄₀ H ₂₄ FNS = 569.69) 3-44 m / z = 607.23 (C ₄₄ H ₃₃ NS = 607.80) 3-45 m / z = 751.23 (C ₅₆ H ₃₃ NS = 751.93) 3-46 m / z = 723.17 (C ₅₀ H ₂₉ NOS ₂ = 723.90) 3-47 m / z = 635.17 (C ₄₄ H ₂₆ FNOS = 635.75) 3-48 m / z = 673.24 (C ₄₈ H ₃₅ NOS = 673.86) 3-49 m / z = 679.11 (C ₄₄ H ₂₅ NOS ₃ = 679.87) 3-50 m / z = 591.11 (C ₃₈ H ₂₂ FNOS ₂ = 591.72) 3-51 m / z = 629.18 (C ₄₂ H ₃₁ NOS ₂ = 629.83) 3-52 m / z = 503.12 (C ₃₂ H ₁₉ F ₂ NOS = 503.56) 3-53 m / z = 557.18 (C ₃₆ H ₂₈ FNO ₂ S = 557.68) 3-54 m / z = 557.18 (C ₃₆ H ₂₈ FNO ₂ S = 557.68) 3-55 m / z = 451.14 (C ₃₂ H ₂₁ NS = 451.58) 3-56 m / z = 451.14 (C ₃₂ H ₂₁ NS = 451.58) 3-57 m / z = 617.22 (C ₄₅ H ₃₁ NS = 617.80) 3-58 m / z = 4617.22 (C ₄₅ H ₃₁ NS = 617.80) 3-59 m / z = 643.23 (C ₄₇ H ₃₃ NS = 643.84) 3-60 m / z = 667.23 (C ₄₉ H ₃₃ NS = 667.86) 3-61 m / z = 667.23 (C ₄₉ H ₃₃ NS = 667.86) 3-62 m / z = 717.25 (C ₅₃ H ₃₅ NS = 717.92) 3-63 m / z = 673.19 (C ₄₇ H ₃₁ NS ₂ = 673.89) 3-64 m / z = 585.19 (C ₄₁ H ₂₈ FNS = 585.73) 3-65 m / z = 623.26 (C ₄₅ H ₃₇ NS = 623.85) 3-66 m / z = 683.26 (C ₅₀ H ₃₇ NS = 683.90) 3-67 m / z = 451.14 (C ₃₂ H ₂₁ NS = 451.58) 3-68 m / z = 501.16 (C ₃₆ H ₂₃ NS = 501.64) 3-69 m / z = 501.16 (C ₃₆ H ₂₃ NS = 501.64) 3-70 m / z = 527.17 (C ₃₈ H ₂₅ NS = 527.68) 3-71 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-72 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-73 m / z = 601.19 (C ₄₄ H ₂₇ NS = 601.76) 3-74 m / z = 557.13 (C ₃₈ H ₂₃ NS ₂ = 557.73) 3-75 m / z = 469.13 (C ₃₂ H ₂₀ FNS = 469.57) 3-76 m / z = 507.20 (C ₃₆ H ₂₉ NS = 507.69) 3-77 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-78 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-79 m / z = 601.19 (C ₄₄ H ₂₇ NS = 601.76) 3-80 m / z = 601.19 (C ₄₄ H ₂₇ NS = 601.76) 3-81 m / z = 651.20 (C ₄₈ H ₂₉ NS = 651.82) 3-82 m / z = 607.14 (C ₄₂ H ₂₅ NS ₂ = 607.78) 3-83 m / z = 519.15 (C ₃₆ H ₂₂ FNS = 519.63) 3-84 m / z = 557.22 (C ₄₀ H ₃₁ NS = 557.75) 3-85 m / z = 551.17 (C ₄₀ H ₂₅ NS = 551.70) 3-86 m / z = 577.19 (C ₄₂ H ₂₇ NS = 557.74) 3-87 m / z = 677.22 (C ₅₀ H ₃₁ NS = 677.85) 3-88 m / z = 727.23 (C ₅₄ H ₃₃ NS = 727.91) 3-89 m / z = 727.23 (C ₅₄ H ₃₃ NS = 727.91) 3-90 m / z = 683.17 (C ₄₈ H ₂₉ NS ₂ = 683.88) 3-91 m / z = 595.18 (C ₄₂ H ₂₆ FNS = 595.73) 3-92 m / z = 633.25 (C ₄₆ H ₃₅ NS = 633.84) 3-93 m / z = 679.23 (C ₅₀ H ₃₃ NS = 679.87) 3-94 m / z = 703.23 (C ₅₂ H ₃₃ NS = 703.89)

On the other hand, each of the substituents of the compounds represented by the formula (1) has a broad relationship, exemplarily described the synthesis examples of the representative compounds, the compounds represented by the formula (1) not illustrated by way of example as a synthesis example Can be configured.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic electric device, including the organic light emitting device to satisfy the conditions required for each organic material layer Materials can be prepared.

The compound according to the present invention may be used in various applications in the organic electroluminescent device according to the type and nature of the substituent. That is, the compound of the present invention can be applied to various layers other than the host of the phosphorescent or fluorescent light emitting layer because it is free to be controlled by the core and the substituent.

Manufacturing Evaluation of Organic Electrical Device

< Experimental Example  1>

First, a copper phthalocyanine (CuPc) film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 10 nm. Subsequently, 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl was vacuum deposited to a thickness of 30 nm on the hole injection layer to form a hole transport layer. In addition, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer by doping at 95: 5 weight using a compound of the present invention as a host material and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] as a dopant material. . Subsequently, ((1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.

< Comparative example  1>

An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that the compound represented by Comparative Compound 2 was used as a host material instead of the compound of the present invention when forming the emission layer.

          <Comparative Compound 1>

Measurement results of device performance, that is, driving voltage, current density, brightness, efficiency, lifetime, and color coordinates of the organic light emitting diodes manufactured by Experimental Example 1 and Comparative Example 1 of the present invention are shown in Table 5 below. In Table 5, the organic light emitting display device manufactured according to the experimental example of the present invention is represented by Examples 1 to 145.

< Experimental Example  2>

First, a 4,4'4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (hereinafter abbreviated as 2T-NATA) film was formed on an ITO layer (anode) formed on a glass substrate. Vacuum deposition was performed to form a 10 nm thick hole injection layer. Subsequently, the compound of the present invention was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm. In addition, a 45 nm-thick light emitting layer doped with BD-052X (Idemitus) 7% doped was formed on the hole transport layer (where BD-052X is a blue fluorescent dopant, and 9,10-die (naphthalene-) as a light emitting host material. 2-anthracene (AND))). Subsequently, ((1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, Tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm on the hole blocking layer to form an electron injection layer. Subsequently, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting diode was manufactured by forming an Al / LiF cathode.

< Comparative example  2>

An organic light emitting display device was manufactured in the same manner as in Experiment 2, except that the compound represented by Comparative Compound 2 was used instead of the compound of the present invention when forming the hole injection layer.

&Lt; Comparative Compound 2 >

Measurement results of device performance, that is, driving voltage, current density, brightness, efficiency, lifespan, and color coordinates of the organic light emitting diodes manufactured by Experimental Example 2 and Comparative Example 2 of the present invention are shown in Table 6 below. In Table 6 below, the organic light emitting display device manufactured according to Experimental Example 2 of the present invention is represented by Examples 146 to 157.

compound Voltage Current density Brightness
(cd / m &lt; 2 & Efficiency Lifetime
T (90) CIE
(x, y) Comparative Example (2) Comparative compound 2 6.6 7.5 300.0 4.0 57.4 (0.15, 0.15) Example (146) Compound (3-4) 6.0 5.2 300.0 5.7 102.8 (0.15, 0.14) Example (147) Compound (3-20) 5.2 5.9 300.0 5.1 147.8 (0.15, 0.14) Example (148) Compound (3-28) 5.9 5.2 300.0 5.8 121.9 (0.14, 0.14) Example 149 Compound (3-29) 4.8 5.8 300.0 5.2 135.4 (0.15, 0.14) Example (150) Compound (3-30) 5.2 4.8 300.0 6.2 104.5 (0.14, 0.14) Example 151 Compound (3-31) 5.9 5.4 300.0 5.5 101.2 (0.15, 0.15) Example 152 Compound (3-32) 5.3 5.2 300.0 5.8 147.4 (0.15, 0.13) Example 153 Compound (3-33) 5.2 5.4 300.0 5.5 142.6 (0.15, 0.14) Example 154 Compound (3-70) 4.8 5.0 300.0 6.0 112.1 (0.15, 0.16) Example (155) Compound (3-86) 5.8 5.9 300.0 5.0 94.3 (0.15, 0.14) Example 156 Compound (3-93) 5.0 4.9 300.0 6.1 145.0 (0.14, 0.14) Example (157) Compound (4-94) 5.2 6.2 300.0 4.9 94.8 (0.14, 0.14)

As can be seen in Table 5 and Table 6, when the compound according to the present invention is used as a light emitting host or hole transport layer material, the driving voltage of the organic light emitting device can be lowered, and color purity, luminous efficiency and lifespan can be remarkably improved. Can be. Even if the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a light emitting auxiliary layer, an electron injection layer, an electron transport layer, and a hole injection layer, it is obvious that the same effect can be obtained.

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 not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of equivalents should be construed as falling within the scope of the present invention.

Claims (9)

A compound represented by the formula:

In the above formulas,
A ring is a C ₆ ~ C ₆₀ single or polycyclic aromatic or heterocyclic ring, X is S, SO or SO ₂ , n is 1 or 2,
R ₁ to R ₁₁ are each independently hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ Heterocyclic group, C ₁ ~ C ₃₀ Alkoxy group, C ₆ ~ C _{30 It} is selected from the group consisting of aryloxy group and C ₁ ~ C ₅₀ Alkyl group,
Y is a direct bond, provided that n = 2; Hydrogen, deuterium, halogen, nitrile group, nitro group, -LN (Ar ₁ ) (Ar ₂ ), C ₆ ~ C ₆₀ aryl group, fluorenyl group, C ₂ ~ C ₆₀ heterocyclic group, C ₁ ~ C ₃₀ alkoxy group, C ₆ ~ C ₃₀ aryloxy and C ₁ ~ C ₅₀ monovalent substituent selected from the group consisting of an alkyl group or a; Or a C ₆ to C ₆₀ arylene group, a fluorenylene group, a C ₆ to C ₆₀ aromatic ring and a C ₃ to C ₆₀ alicyclic fused ring, a C ₂ to C ₆₀ heterocyclic group or a divalent aliphatic hydrocarbon Is selected from the group of divalent substituents consisting of groups,
L is a direct bond, C ₆ ~ C ₆₀ arylene group, fluorenylene group, C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ alicyclic fused ring, C ₂ ~ C ₆₀ heterocyclic group Or divalent aliphatic hydrocarbon, wherein Ar ₁ and Ar ₂ are each independently C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heterocyclic group, fluorenyl group, C ₁ -C ₃₀ Is selected from the group consisting of an alkoxy group, a C ₆ -C ₃₀ aryloxy group and a C ₁ -C ₅₀ alkyl group.
(In the Y, R ₁ to R _11, Ar ₁ and Ar ₂ of C ₆ ~ C ₆₀ aryl group, wherein Y, R ₁ to R _11, a fluorene group, and the Y and L of Ar ₁ and Ar ₂ The arylene group and the Y and L fluorenylene groups are deuterium, halogen, silane group, boron group, germanium group, C ₁ ~ C ₂₀ alkylthio group, C ₆ ~ C ₂₀ arylthio group, C ₁ ~ C ₂₀ alkoxy group, -N (Ar ₁ ) (Ar ₂ ), C ₁ -C ₂₀ alkyl group, C7-C20 arylalkyl group, C ₂ -C ₂₀ alkenyl group, C ₈ -C ₂₀ arylalkenyl group Substituted by at least one substituent selected from the group consisting of C ₂ ~ C ₂₀ Alkynyl group, C ₃ ~ C ₂₀ Cycloalkyl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium and C ₂ ~ C ₂₀ heterocyclic group Can be,
Wherein Y, R ₁ to R _11, L, Ar ₁ and a heterocyclic group of C ₂ ~ C ₆₀ of the Ar ₂ groups include at least one heteroatom of O, N, S, Si and P, heavy hydrogen, a halogen group, -N (Ar ₁ ) (Ar ₂ ), C ₁ -C ₂₀ alkyl group, C ₇ -C ₂₀ arylalkyl group, C ₂ -C ₂₀ alkenyl group, C ₈ -C ₂₀ arylalkenyl group, C _1- It may be substituted with one or more substituents selected from the group consisting of C ₂₀ alkoxy group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, a nitrile group and an acetylene group,
The C ₁ to C ₃₀ alkoxy group and C ₆ to C ₃₀ aryloxy group of Y, R ₁ to R ₁₁ , Ar ₁ and Ar ₂ are deuterium, halogen, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl groups, C ₂ to C ₂₀ alkenyl groups, C ₁ to C ₂₀ alkoxy groups, C ₃ to C ₃₀ cycloalkyl groups, C ₆ to C ₆₀ aryl groups, deuterium substituted with C ₆ to C ₂₀ It may be substituted with one or more substituents selected from the group consisting of an aryl group and a C ₂ ~ C ₆₀ heterocyclic group,
The C ₁ to C ₅₀ alkyl group of Y, R ₁ to R ₁₁ , r _1, and Ar ₂ may be a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group, In the group consisting of C ₆ ~ C ₂₀ aryl group, C ₇ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ heterocyclic group, nitrile group and acetylene group May be substituted with one or more substituents selected) The method of claim 1,
Compound represented by one of the following formula.
(2)

(3)

&Lt; Formula 4 >

(A in Formula 2 to Formula 4, R ₁ to R ₁₁ and X are the same as defined in Formula 1, Y in Formula 2 is selected from the group of monovalent substituents in the Y definition of Formula 1, Y is a direct bond or is selected from the group of divalent substituents in the definition of Y in Formula 1, and L, Ar ₁ and Ar ₂ in Formula 4 are as defined in Formula 1) The method of claim 1,
Compound represented by one of the following formula.
&Lt; Formula 5 >

(6)

&Lt; Formula 7 >

(R ₁ to R ₈ and X in Formula 5 to Formula 7 are the same as defined in Formula 1, Y in Formula 5 is selected from the monovalent substituent group in the definition of Y in Formula 1, Y in Formula 6 is Or a divalent substituent in the definition of Y in Formula 1, wherein L, Ar ₁ and Ar ₂ in Formula 7 are as defined in Formula 1) The method of claim 1,
Lt; / RTI &gt; is one of the following compounds.

In an organic electric device comprising a first electrode, one or more organic material layers and a second electrode sequentially stacked,
The organic material layer is an organic electroluminescent device comprising the compound of claim 1. 6. The method of claim 5,
Characterized in that said compound is formed into said organic material layer by a soluble process. 6. The method of claim 5,
The organic material layer includes a light emitting layer and / or a hole transport layer,
At least one of the light emitting layer and the hole transport layer is formed of the compound. A display device comprising the organic electroluminescent device of claim 5; And
A controller for driving the display device; &Lt; / RTI &gt; The electronic device of claim 8, wherein the organic electronic device is one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a single color or white light emitting device.

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