KR20150133998A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

In the present invention, provided is a compound represented by chemical formula 1. In addition, provided is an organic electric device comprising: a first electrode; a second electrode; and an organic material layer between the first electrode and the second electrode, wherein the organic material layer comprises a compound represented by chemical formula 1. If the compound represented by chemical formula 1 is included in the organic material layer of the organic electric device, driving voltage is reduced and light emitting efficiency, color purity and lifespan can be improved.

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 the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer. 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 moves to the wavelength of the dopant, light of the desired wavelength can be obtained according to the type of the dopant used.

Currently, the portable display market is growing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption becomes a very important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues must be solved.

The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimum combination of the energy level and the T ₁ value and the intrinsic properties (mobility, interfacial characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time .

Therefore, it is necessary to develop a light emitting material having high thermal stability and achieving a charge balance in the light emitting layer efficiently. That is, in order to fully exhibit the excellent characteristics of the organic electronic device, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer for an organic electric device has not yet been sufficiently developed. Particularly, development of a host material for a light emitting layer is urgently required.

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

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 embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency, color purity and lifetime of the device can be greatly improved.

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, the terms first, second, A, B, (a), (b), and the like can 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."

In addition, when an element such as a layer, film, region, plate, or the like is referred to as being "on" or "on" another element, And the like. On the contrary, when an element is referred to as being "directly on " another element, it should be understood that it does not have another element in the middle.

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 "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.

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.

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.

In addition, a no explicit description, the terms used in this invention in the "unsubstituted or substituted", "substituted" is an alkyl group of deuterium, a halogen, an amino group, a nitrile group, a nitro _{group, C 1 -C 20, C 1} -C _20, an alkoxyl group of, 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, C ₂ -C of ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron Group, a germanium group, and a C ₂ -C ₂₀ heterocyclic group, and the substituent is not limited to these substituents.

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

1, an organic electroluminescent device 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180 and a first electrode 110 formed on a substrate 110, And an organic material layer containing a compound according to the present invention is provided between the two electrodes 180. 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 an embodiment of the present invention further includes 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 can do.

The compound according to one embodiment of 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 may be used as a material for the light-efficiency improvement layer.

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 an embodiment of the present invention may be a front 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 an embodiment of the present invention may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochromatic 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 >

이며, X는 O, S 및 Se로 이루어진 군에서 선택될 수 있다.In the above formula (1), A represents

, And X may be selected from the group consisting of O, S and Se.

Z may be selected from the group consisting of NAr ¹ , O, and S.

Ar and Ar ¹ are, independently of each other, a C ₆ -C ₆₀ aryl group; A fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group; ≪ / RTI > For example, Ar and Ar ¹ can be, independently of each other, phenyl, biphenyl, naphthyl, terphenyl, dibenzothiophene, dibenzofuran, 9-phenyl-9H-carbazole and deuterium-substituted phenyl.

R ¹ to R ⁸ independently of one another are hydrogen, deuterium, C ₆ -C ₆₀ aryl; A fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; A C ₆ -C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b );

In addition, R ¹ to R ⁸ may be bonded to each other to form at least one ring, and R ¹ to R ⁸ which do not form a ring may be defined as defined above.

The ring formed by combining adjacent groups may be a fused ring composed of a C ₃ -C ₆₀ aliphatic ring, a C ₆ -C ₆₀ aromatic ring, a C ₂ -C ₆₀ hetero ring, or a combination thereof, May be a single ring or multiple rings, but may also be a saturated or unsaturated ring.

L 'is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And heterocyclic groups of C ₂ -C _60; may be selected from the group consisting of.

R ^a and R ^b are independently of each other a C ₆ -C ₆₀ aryl group; A fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And an aryloxy group of C ₆ -C ₃₀ .

Here, each of the aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxyl group, the aryloxy group, the arylene group and the fluorenylene group may be deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ An aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; And an arylalkenyl group having from _{8 to 20} carbon atoms.

Specifically, the compound represented by Formula 1 may be represented by Formula 2 or Formula 3 below.

         &Lt; Formula 2 > < EMI ID =

In the general formulas (2) and (3), Ar, X, Z and R ¹ to R ⁸ may be defined as defined in the general formula (1).

More specifically, the compound represented by the formula (1) may be represented by the following formulas (4) to (15).

 &Lt; Formula 4 > < EMI ID =

 &Lt; Formula 8 > < EMI ID =

&Lt; Formula 12 > < EMI ID = 13.0 >

In the general formulas (4) to (15), Ar and R ¹ to R ⁸ may be defined as defined in the general formula (1).

More specifically, the compounds represented by the above Chemical Formulas 1 to 15 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, wherein the organic material layer may include a compound represented by Formula 1, wherein Formula 1 is a hole injection layer, a hole transport layer, Layer or at least one of the light-emitting layer. That is, the compound represented by the formula (1) can be used as a material for the hole injection layer, the hole transport layer, the light emission assisting layer or the light emitting layer. Further, the compound represented by the general formula (1) can be used as a phosphorescent host material of the light emitting layer.

Specifically, the organic material layer may include one of the compounds represented by Chemical Formula 2 or Chemical Formula 3, and more specifically, the organic material layer may include one of the compounds represented by Chemical Formulas 4 to 15 Organic electroluminescent device, and more particularly, to the organic material layer, the organic electroluminescent device according to any one of the above-mentioned formulas 2-1 to 2-36, 3-1 to 3-36, 4-1 to 4-36, 5-1 to 5-36, -1 to 6-36, 7-1 to 7-12, 8-1 to 8-12, 9-1 to 9-12, 10-1 to 10-12, 11-1 to 11-12, 12-1 To 12-12 and 13-1 to 13-12.

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 phosphorescent host material of the light emitting layer according to an embodiment of the present invention may contain two different compounds, such as the individual compounds 2-1 and 2-2, and the individual compounds 2-1, 3-1 and 4 -1. &Lt; / RTI &gt;

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

Synthetic example

Illustratively, the compounds according to the present invention (Final Products) are prepared by the synthetic method as shown in Reaction Scheme 1 below, but are not limited thereto.

<Reaction Scheme 1>

I. Sub  1 of Synthetic example

One. Sub  Z of 1 NAr ^One If

In the above Reaction Scheme 1, Sub 1 in the case where Z is NAr ¹ can be synthesized by the reaction path of the following reaction scheme 2-1, but is not limited thereto.

<Reaction Scheme 2-1>

(One) SM Synthesis of -3

(1 eq.), SM-2 (1.1 eq.), Pd ₂ (dba) ₃ (0.05 eq.), P (t-Bu) ₃ (0.1 eq.), T- BuONa , toluene (10 mL / SM-1 1 mmol), and the reaction is allowed to proceed at 100 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain SM-3. (Yield: 60-80%).

(2) Sub  Synthesis of 1-1

After SM-3 (1 eq.) Was dissolved in anhydrous ether, the temperature of the reaction was lowered to -78 ° C and n-BuLi (2.5 M in hexane) (1.1 eq.) Was slowly added dropwise and the reaction was stirred for 30 minutes . The temperature of the reaction was then lowered to -78 ° C and triisopropyl borate (1.5 eq.) Was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain Sub 1-1. (Yield: 70-90%).

(3) Sub  Synthesis of 1-1 (a)

SM Synthesis of -3-1

To a round bottom flask was added SM-1 (4.9g, 20mmol) , SM-2-1 (4.48g, 22mmol), Pd 2 (dba) 3 (0.3g, 0.6mmol), P (t-Bu) 3 (0.2g , T-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were added thereto, and the reaction was allowed to proceed at 100 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried with MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 4.8 g of SM-3-1. (Yield: 75%).

Sub  Synthesis of 1-1 (a)

SM-3 (6.4 g, 20 mmol) was dissolved in anhydrous ether, the temperature of the reaction was lowered to -78 캜, n-BuLi (2.5 M in hexane) (8.8 ml, 22 mmol) was slowly added dropwise, Lt; / RTI &gt; The temperature of the reaction was then lowered to -78 ° C and triisopropyl borate (6.9 ml, 30 mmol) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 4 g of Sub 1-1 (a). (Yield: 70%).

2. Sub  When Z of 1 is O or S

In the above Reaction Scheme 1, Sub 1 in the case where Z is O or S can be synthesized by the reaction path of the following reaction formula 2-2, but is not limited thereto.

<Reaction Scheme 2-2>

(One) SM Synthesis of -1-2

SM-1-1 (1 equivalent) was dissolved in CH ₂ Cl ₂ , cooled to 0 ° C, bromine (0.9 equivalent) was slowly added dropwise, then slowly warmed to room temperature, and the reaction was stirred for 10 hours. After completion of the reaction, bromine is removed with an aqueous sodium thiosulfate solution. After extraction with ethyl acetate and water, the organic layer was dried with MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain SM-1-2. (Yield: 70-90%).

(2) Sub  Synthesis of 1-2

SM-1-2 (1 eq.) Was dissolved in anhydrous ether, the temperature of the reaction was lowered to -78 ° C and n-BuLi (2.5 M in hexane) (1.1 eq.) Was slowly added dropwise, Lt; / RTI &gt; The temperature of the reaction was then lowered to -78 ° C and triisopropyl borate (1.5 eq.) Was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over MgSO ₄ and concentrated. Subsequently, the resulting organic material was subjected to silicagel column and recrystallization to obtain Sub 1-2. (Yield: 70-90%).

(3) Sub  Synthesis of 1-2 (a)

SM -1-2 Synthesis of (a)

SM-1-1 (a) (9.2 g, 50 mmol) was dissolved in CH ₂ Cl ₂ , Br ₂ (2.3 ml, 45 mmol) was slowly added dropwise and the reaction was stirred for 10 h. After completion of the reaction, bromine is removed with an aqueous sodium thiosulfate solution. After extraction with ethyl acetate and water, the organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 8.2 g of Sub 1-2 (a). (Yield: 72%).

Sub  Synthesis of 1-2 (a)

SM-1-2 (a) (5.3 g, 20 mmol) was dissolved in anhydrous ether, the temperature of the reaction was lowered to -78 ° C, and n-BuLi (2.5 M in hexane) (8.8 ml, 22 mmol) The reaction was then stirred for 30 minutes. The temperature of the reaction was then lowered to -78 ° C and triisopropyl borate (6.9 ml, 30 mmol) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 3.7 g of Sub 1-2 (a). (Yield: 82%)

(4) Sub  Synthesis of 1-2 (b)

SM -1-2 Synthesis of (b)

SM-1-1 (b) (8.4 g, 50 mmol) was dissolved in CH ₂ Cl ₂ , Br ₂ (0.9 equiv.) Was slowly added dropwise, and the reaction was stirred for 10 hours. The temperature of the reaction was then lowered to -78 ° C and triisopropyl borate (1.5 eq.) Was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 9.5 g of SM-1-2 (b). (Yield: 77%)

Sub  Synthesis of 1-2 (b)

SM-1-2 (b) (4.9 g, 20 mmol) was dissolved in anhydrous ether, the temperature of the reaction was lowered to -78 ° C, and n-BuLi (2.5 M in hexane) (8.8 ml, 22 mmol) The reaction was then stirred for 30 minutes. The temperature of the reaction was then lowered to -78 ° C and triisopropyl borate (6.9 ml, 30 mmol) was added dropwise. After stirring at room temperature, dilute with water and add 2N HCl. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 3.1 g of Sub 1-2 (b). (Yield: 74%).

Examples of Sub 1 include, but are not limited to, the following Table 1, FD-MS values of compounds belonging to Sub 1.

[Table 1]

II . Sub  3 of Synthetic example

One. Sub  Z of 3 NAr ^One If

In the above Reaction Scheme 1, Sub 3 in the case where Z is NAr ¹ can be synthesized by the reaction path of the following reaction scheme 3-1, but is not limited thereto.

<Reaction Scheme 3-1>

Sub 1-1 (1.2 eq.), Pd (PPh ₃ ) ₄ (0.03 eq.), NaOH (3 eq.), THF and water (2: 1) are added to a round bottom flask with SM-1 . Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain Sub 3-1. (Yield: 80-90%)

(One) SM  3-1 Synthesis of (a)

Into the SM-1 (4.9g, 20mmol) in a round bottom flask, Sub 1-1 (a) (6.9g , 24mmol), Pd (PPh 3) 4 (0.7g, 0.6mmol), NaOH (2.4g, 60mmol ), THF (60 mL) and water (30 mL). Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to give 6.5 g of Sub 3-1 (a) . (Yield: 80%).

2. Sub  When Z of 3 is O or S

In the above Reaction Scheme 1, Sub 3 in the case where Z is O or S can be synthesized by the reaction path of the following reaction scheme 3-2, but is not limited thereto.

<Reaction Scheme 3-2>

Sub 1-1 (1.2 eq.), Pd (PPh ₃ ) ₄ (0.03 eq.), NaOH (3 eq.), THF and water (2: 1) are added to a round bottom flask with SM-1 . Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain Sub 3-2. (Yield: 70-80%).

(One) SM  3-2 Synthesis of (a)

Into the SM-1 (4.9g, 20mmol) in a round bottom flask, Sub 1-2 (a) (5.5g , 24mmol), Pd (PPh 3) 4 (0.7g, 0.6mmol), NaOH (2.4g, 60mmol ), THF (60 mL) and water (30 mL). Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to give 5.1 g of Sub 3-1 (a) . (Yield: 73%)

(2) SM  3-2 Synthesis of (b)

Sub-1-2 (b) (5.1 g, 24 mmol), Pd (PPh ₃ ) ₄ (0.7 g, 0.6 mmol) and NaOH (2.4 g, 60 mmol) were added to a round bottom flask. ), THF (60 mL) and water (30 mL). Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to give 4.7 g of Sub 3-1 (a) . (Yield: 71%).

Examples of Sub 3 include, but are not limited to, the following Table 2, FD-MS values of compounds belonging to Sub 3.

[Table 2]

III . Sub  4 of Synthetic example

In Scheme 1, Sub 4 can be synthesized by the reaction path of the following reaction scheme 4, but is not limited thereto.

<Reaction Scheme 4>

Add SM-5 (1.2 eq.), Pd (PPh ₃ ) ₄ (0.03 eq.), NaOH (3 eq.) And THF and water (2: 1) into a round bottom flask. Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain Sub 4. (Yield: 80-90%)

(One) Sub  Synthesis of 4-1 (a)

To a round bottom flask was added SM-4-1 (5.1g, 20mmol) were dissolved, SM-5-1 (2.9g, 24mmol ), Pd (PPh 3) 4 (0.7g, 0.6mmol), NaOH (2.4g, 60mmol ), THF (60 mL) and water (30 mL). Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 4.8 g of Sub 4-1 (a). (Yield: 81%).

(2) Sub  Synthesis of 4-2 (a)

To a round bottom flask was added SM-4-2 (5.1g, 20mmol) were dissolved, SM-5-1 (2.9g, 24mmol ), Pd (PPh 3) 4 (0.7g, 0.6mmol), NaOH (2.4g, 60mmol ), THF (60 mL) and water (30 mL). Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 5.0 g of Sub 4-2 (a). (Yield: 85%).

(3) Sub  4-3 Synthesis of (a)

To a round bottom flask was added SM-4-3 (4.8g, 20mmol) were dissolved, SM-5-1 (2.9g, 24mmol ), Pd (PPh 3) 4 (0.7g, 0.6mmol), NaOH (2.4g, 60mmol ), THF (60 mL) and water (30 mL). Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 4.9 g of Sub 4-3 (a). (Yield: 87%).

(4) Sub  4-4 Synthesis of (a)

Into the SM-4-4 (4.8g, 20mmol) in a round bottom flask, Sub 5-1 (2.9g, 24mmol) , Pd (PPh 3) 4 (0.7g, 0.6mmol), NaOH (2.4g, 60mmol) , THF (60 mL) and water (30 mL). Then, the mixture is heated to reflux at 80 ° C to 90 ° C. When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 5.0 g of Sub 4-4 (a). (Yield: 89%).

Examples of Sub 4 include, but are not limited to, the FD-MS values of compounds belonging to Sub 4 in Table 3 below.

[Table 3]

IV . The final product ( Final products )of Synthetic example

To a round bottom flask Sub 3 (1 eq.), Sub 4 (1.2 _{eq), Pd 2 (dba) 3} (0.03 eq.), P (t-Bu) 3 (0.1 equiv), t-BuONa (3 equiv.), Toluene And the reaction proceeds at 100 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized.

1. 2-1 Synthetic example

Sub-3-1 (a) (8.2 g, 20 mmol), Sub 4-1 (a) (7.1 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 10.5 g of 2-1. (Yield: 78%).

2. 2-7 Synthetic example

Sub-3-1 (a) (8.2 g, 20 mmol), Sub 4-1 (g) (9.6 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 12.3 g of 2-7. (Yield: 79%).

3. 2-9 Synthetic example

Sub-3-1 (a) (8.2 g, 20 mmol), Sub 4-1 (g) (9.3 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 13.1 g of 2-9 . (Yield: 86%)

4. 2-13 Synthetic example

Sub-3-1 (b) (9.7 g, 20 mmol), Sub 4-1 (a) (7.1 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 12.1 g of 2-13. (Yield: 81%).

5. 2-25 Synthetic example

Sub-3-1 (b) (9.7 g, 20 mmol), Sub 4-1 (a) (7.1 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 2.25 g of 2-25. (Yield: 72%).

6. 3-1 Synthetic example

Sub-3-1 (a) (8.2 g, 20 mmol), Sub 4-1 (a) (9.6 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 11.5 g of 3-1. (Yield: 86%)

7. 4-1 Synthetic example

Sub-3-1 (a) (8.2 g, 20 mmol), Sub 4-3 (a) (6.7 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 9.3 g of 4-1. (Yield: 71%).

8. 5-1 Synthetic example

Sub-3-1 (a) (8.2 g, 20 mmol), Sub 4-4 (a) (6.7 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The organic matter was purified by silicagel column and recrystallized to obtain 9.8 g of 5-1. (Yield: 75%).

9. 6-1 Synthetic example

Sub-3-2 (a) (6.9 g, 20 mmol), Sub 4-1 (a) (7.1 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 6.7 g of 6-1. (Yield: 88%).

10. 7-1 Synthetic example

Sub-2-2 (a) (6.9 g, 20 mmol), Sub 4-2 (a) (9.6 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was recrystallized from silicagel column to obtain 9.1 g of 7-1. (Yield: 75%).

11. 8-1 Synthetic example

Sub-3-2 (a) (6.9 g, 20 mmol), Sub 4-3 (a) (6.7 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol) Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 8.3 g of 8-1. (Yield: 70%).

12. 9-1 Synthetic example

(6.9 g, 20 mmol), Sub 4-4 (a) (6.7 g, 24 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.6 mmol), P (t- Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL). After completion of the reaction, the reaction mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 8.5 g of 9-1. (Yield: 72%).

On the other hand, the compounds 2-1 to 2-36, 3-1 to 3-36, 4-1 to 4-36, 5-1 to 5-36 and 6-1 according to the present invention, To 6-36, 7-1 to 7-12, 8-1 to 8-12, 9-1 to 9-12, 10-1 to 10-12, 11-1 to 11-12, 12-1 to 12-12 The FD-MS values of -12 and 13-1 to 13-12 are shown in Table 4 below.

[Table 4]

Evaluation of manufacturing of organic electric device

[ Example  One] Red organic electroluminescent water tank (Phosphorescent host)

An organic electroluminescent device was fabricated according to a conventional method using a compound according to an embodiment of the present invention as a light emitting host material of a light emitting 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 (hereinafter abbreviated as "2-TNATA") was vacuum-deposited to form a 60 nm thick hole injection layer. Subsequently, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl (abbreviated as "NPD" hereinafter) was vacuum deposited on the hole injection layer to a thickness of 20 nm to form a hole transport layer Respectively. The compound 2-1 of the present invention is represented by bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter referred to as "(piq) ₂ Ir (acac)") as a dopant material on the hole transport layer To a weight ratio of 95: 5, and vacuum-deposited to a thickness of 30 nm to form a light emitting layer. Next, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as "BAlq") was vacuum- (8-quinolinol) aluminum (hereinafter abbreviated as "Alq ₃ &quot;) was vacuum deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer. Thereafter, an electron injection layer was formed by depositing LiF, which is an alkali metal halide, to a thickness of 0.2 nm on the electron transport layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Example  2] to [ Example  100] Red organic electroluminescent device (Phosphorescent host)

An organic electroluminescent device was prepared in the same manner as in Example 1 except that one of the compounds of the present invention described in Table 5 was used instead of the compound 2-1 of the present invention as a host material of the emitting layer.

[ Comparative Example  One]

An organic EL device was prepared in the same manner as in Example 1, except that the following compound A was used instead of the compound 2-1 of the present invention as a host material in the light emitting layer.

          &Lt; Comparative Compound A >

[ Comparative Example  2]

An organic electroluminescence device was prepared in the same manner as in Example 1, except that the following compound (B) was used instead of the compound (2-1) of the present invention as a host material in the light emitting layer.

    &Lt; Comparative Compound B >

[ Comparative Example  3]

An organic electroluminescence device was prepared in the same manner as in Example 1, except that the following compound C was used instead of the compound 2-1 of the present invention as a host material in the light emitting layer.

          <Comparative compound C>

[ Comparative Example  4]

An organic EL device was prepared in the same manner as in Example 1, except that the following compound D was used instead of the compound 2-1 of the present invention as a host material in the light emitting layer.

          <Comparative compound D>

[ Comparative Example  5]

An organic EL device was prepared in the same manner as in Example 1, except that the following compound E was used instead of the compound 2-1 of the present invention as a host material in the light emitting layer.

          &Lt; Comparative Compound E >

Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 100 and Comparative Examples 1 to 5 of the present invention And the T95 lifetime was measured using a life measuring device manufactured by Mac Science Inc. at a luminance of 2500 cd / m 2. The measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results shown in Table 5, the organic electroluminescent device using the compound of the present invention as a material of the phosphorescent host has remarkably improved luminous efficiency while lowering the driving voltage.

In other words, generally CBP of Comparative Compound A, Bebq ₂ in comparison to the bis-carbazole (Bis-Carbazole) or carbazole than the device using the compound B dibenzothiophene (Dibenzothiophen) or dibenzo used as a host material furan ( Dibenzofuran was substituted, and had a lower driving voltage and higher efficiency than the device using Comparative Compounds C to E, and had the same core as Comparative Compounds C to E, but did not have benzothienopyrimidine or benzo The device using the compound of the present invention substituted with a specific substituent such as benzofuropyrimidine showed the best results.

This is because the compound having dibenzothiophene or dibenzofuran core in biscarbazole or carbazole has a high HOMO value and energy gap with the dopant becomes small, thereby improving the injection characteristics of holes, As shown in Fig. In addition, the hole trap generated according to the energy barrier is reduced, and holes are more easily transferred to the light emitting layer, resulting in an improved energy balance, resulting in high efficiency.

Compounds of the present invention in which substituents such as benzothienopyrimidine or benzofurpyrimidine are substituted in such cores have a higher HOMO value than comparative compounds C to E and have a smaller energy gap than the dopant As a result, it can be explained that the injection characteristics and the energy balance of the hole are further improved and the device characteristics are the most excellent.

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 (11)

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

In Formula 1,
A is

X is selected from the group consisting of O, S and Se,
Z is selected from the group consisting of NAr ¹ , O and S,
Ar and Ar ¹ are, independently of each other, a C ₆ -C ₆₀ aryl group; A fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And a C ₆ -C ₃₀ aryloxy group; , &Lt; / RTI &gt;
R ¹ to R ⁸ are, independently of each other, i) hydrogen, deuterium, C ₆ -C ₆₀ aryl; A fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; A C ₆ -C ₃₀ aryloxy group; And -L'-N (R ^a ) (R ^b ); or ii) adjacent groups may combine with each other to form at least one ring, wherein R ¹ To R &lt; ⁸ &gt; are defined the same as those defined in i) above,
L 'is a single bond; C ₆ -C ₆₀ arylene groups; A fluorenylene group; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; And heterocyclic groups of C ₂ -C _60; is selected from the group consisting of,
R ^a and R ^b are independently of each other a C ₆ -C ₆₀ aryl group; A fluorenyl group; A C ₂ -C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C ₃ -C ₆₀ aliphatic ring and a C ₆ -C ₆₀ aromatic ring; A C ₁ -C ₅₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; A C ₁ -C ₃₀ alkoxyl group; And an aryloxy group having from _{6 to 30} carbon atoms,
Here, each of the aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxyl group, the aryloxy group, the arylene group and the fluorenylene group may be deuterium; halogen; A silane group; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C ₁ -C ₂₀ ; A C ₁ -C ₂₀ alkoxyl group; A C ₁ -C ₂₀ alkyl group; An alkenyl group of C ₂ -C ₂₀ ; A C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ An aryl group; A C ₆ -C ₂₀ aryl group substituted by deuterium; A fluorenyl group; A C ₂ -C ₂₀ heterocyclic group; A C ₃ -C ₂₀ cycloalkyl group; An arylalkyl group of C ₇ -C ₂₀ ; And an arylalkenyl group having from _{8 to 20} carbon atoms. The method according to claim 1,
A compound represented by one of the following formulas:
&Lt; Formula 2 >< EMI ID =

In the general formulas (2) and (3), Ar, X, Z and R ¹ to R ⁸ are defined as defined in claim 1. The method according to claim 1,
A compound represented by one of the following formulas:
&Lt; Formula 4 >< EMI ID =

&Lt; Formula 8 &gt;&lt; EMI ID =

&Lt; Formula 12 >< EMI ID = 13.0 >

In the general formulas (4) to (15), Ar and R ¹ to R ⁸ are defined as defined in claim 1. The method according to claim 1,
Lt; / RTI &gt; 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 4. 6. The method of claim 5,
The compound is contained in the light-emitting layer of the organic material layer,
Wherein the compound is a homologous compound or two or more different kinds of compounds. The method according to claim 6,
Wherein the compound is used as a phosphorescent host material of the light emitting layer. 6. The method of claim 5,
Further comprising a light-efficiency-improvement layer formed on at least one side of the one surface of the first electrode and the second electrode opposite to the organic material layer. 6. The method of claim 5,
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 comprising the organic electroluminescent device of claim 5; And
And a control unit for driving the display device. 11. The electronic device according to claim 10, wherein the organic electroluminescent device is at least 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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