KR101822827B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving luminous efficiency, stability and lifetime of a device, an organic electric device using the same, and an electronic device thereof.

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.

On the other hand, the diffusion of metal oxide from the anode electrode (ITO), which is one of the causes of shortening the lifetime of the organic electronic device, is delayed, and stable characteristics such as joule heating generated during driving the device, It is necessary to develop a hole injection layer material having a temperature. It is also reported that the low glass transition temperature of the hole transporting layer material significantly affects the lifetime of the device depending on the characteristics of the uniformity of the thin film surface collapsing during device operation. In addition, the deposition method is the mainstream in the formation of OLED devices, and a material that can withstand such a long time, that is, a material having high heat resistance characteristics, is required.

In order to sufficiently exhibit the excellent characteristics of the organic electroluminescent device described above, 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, stable and efficient development of an organic material layer for an organic electric device has not yet been sufficiently developed, and therefore development of a new material is continuously required.

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

In one aspect, the present invention provides a compound represented by the following general formula (1).

≪ Formula 1 >

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

By using the compound according to the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and lifetime of the device.

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

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

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference symbols as possible even if 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."

The term " halo "or" halogen "as used herein, on the other hand, includes fluorine, chlorine, bromine, and iodine unless otherwise specified.

The term "alkyl" or "alkyl group ", as used herein, unless otherwise specified, has from 1 to 60 carbon atoms, but is not limited thereto.

The term "alkenyl" or "alkynyl ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms,

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 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 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.

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" used in the present invention means an aryl or arylene group having 3 to 60 carbon atoms, each of which contains at least one heteroatom unless otherwise specified, 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, and is not limited to these substituents.

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

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Comprising an organic compound layer comprising a compound according to the present invention. In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to the present invention may further include a protective layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material 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, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode 120, and a hole injecting layer 130, a hole transporting layer 140, a light emitting auxiliary layer 151, An electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used 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 can be formed by various methods, the scope of the present invention is not limited by the forming method.

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

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

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).

In the above formulas,

Wherein A and B are C ₆ to C ₃₀ aromatic rings,

R ₁ to R ₈ are independently selected from the group consisting of i) independently of one another hydrogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ -C ₆₀ ; A C ₃ -C ₆₀ cycloalkyl group; And _{-LN (Ar 3) (Ar 4} ); or selected from the group consisting of, or ⅱ) forms at least one ring in combination with each other between the neighboring group. Here, the group which does not form a ring is the same as defined in (i).

The adjacent groups of R ₁ and R ₈ are bonded to each other to form at least one ring. It is preferable that R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ and / or R ₇ and R ₈ are bonded to each other to form a ring. At this time, since it is important that neighboring groups bond together to form a ring, the scope of the present invention is not limited by what kind of substituent and which reaction forms the ring.

The ring formed by bonding adjacent groups of R ₁ and R ₈ to each other may be a monocyclic or polycyclic aromatic ring or a heterocyclic ring containing at least one heteroatom as well as an aromatic ring and an aliphatic ring fused together. Illustratively, neighboring groups of R ₁ and R _{8 may} be bonded to each other to form an aromatic ring such as benzene, naphthalene, phenanthrene, etc., wherein the number of carbon atoms in the aromatic ring formed is preferably 6 to 60. For example, when R ₅ and R ₆ are bonded to each other to form a benzene ring and R ₇ and R ₈ bond to each other to form a benzene ring, a phenanthrene form may be formed together with a benzene ring of the coupled parent.

Ar ₁ and Ar ₂ are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; And -LN (Ar ₃ ) (Ar ₄ );

L is a direct bond; An arylene group having ₆ to ₆₀ carbon atoms; A fluorenylene group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; And a divalent aliphatic hydrocarbon group; is selected from the group consisting of these (direct negative binding) each of a nitro group, a nitrile group, halogen group, C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₂₀ aryl group, C ₂ - heterocyclic group of C _20, and may be substituted with C ₁ ~ one or more substituents selected from the group consisting of an alkoxy group and an amino group of the C _20,

Ar ₃ and Ar ₄ are each independently a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And a C ₁ to C ₅₀ alkyl group.

R ₁ to R ₈ and Ar ₁ to Ar ₄ may be further substituted with other substituents.

Wherein R ₁ ~ R ₈ and Ar ₁ ~ Ar ₄ is, if an aryl group, which is hydrogen, deuterium, a halogen, a silane group, a boron group, a germanium group, a cyano group, an import nitro group, C ₁ ~ alkylthio of C _20, C an aryl group of ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of alkenyl groups _{(alkenyl), C 2 ~ C} 20 of the alkynyl group _{(alkynyl), C 6 ~ C} 20 of, of a C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ of the substitution with deuterium An arylalkyl group, and an arylalkenyl group having ₈ to ₂₀ carbon atoms,

Wherein R ₁ ~ R ₈ and Ar ₁ ~ Ar ₄ is, if the heterocyclic group, which is hydrogen, deuterium, a halogen, a silane group, a cyano group, an alkyl group of a nitro group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ of A C ₂ to C ₂₀ alkenyl group, a C ₆ to C ₂₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₂ to C ₂₀ heterocyclic group, a C ₃ to C ₂₀ A cycloalkyl group of C ₇ to C ₂₀ An arylalkyl group and an arylalkenyl group having from ₈ to ₂₀ carbon atoms.

When R ₁ to R ₈ and Ar ₁ to Ar ₄ are fluorenyl groups, they may be replaced by hydrogen, deuterium, halogen, a silane group, a cyano group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group ), C aryl group of ₆ ~ C _20, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₂ ~ C ₂₀ of the heterocyclic group and C ₃ ~ one or more substituents selected from the group consisting of a cycloalkyl group of C ₂₀ , ≪ / RTI >

When R ₁ to R ₈ and Ar ₁ to Ar ₄ are an alkyl group or a cycloalkyl group, it is preferably a halogen, a silane group, a boron group, a cyano group, a C ₁ to C ₂₀ alkoxyl group, a C ₁ to C ₂₀ alkyl group, a C of ₂ ~ C ₂₀ alkenyl group a _{(alkenyl), C 6 ~ C} 20 aryl group, a C ₆ ~ C ₂₀ aryl group, C ₂ ~ C ₂₀ heterocyclic group, C ₇ ~ C ₂₀ substituted by deuterium An arylalkyl group and an arylalkenyl group having from ₈ to ₂₀ carbon atoms.

When R ₁ to R ₈ are alkenyl groups, they may be substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, silane, cyano, C ₁ to C ₂₀ alkoxyl, C ₁ to C ₂₀ alkyl, C ₂ to C ₂₀ alkenyl a C ₆ to C ₂₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₂ to C ₂₀ heterocyclic group, a C ₃ to C ₂₀ cycloalkyl group, a C ₇ to C ₂₀ alkenyl group, of An arylalkyl group, and an arylalkenyl group having ₈ to ₂₀ carbon atoms,

Wherein R ₁ ~ R ₈ is aryl case oxy group which of hydrogen, deuterium, a silane group, a cyano group, C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with heavy hydrogen in the Which may be substituted with at least one substituent selected from the group consisting of an aryl group, a C ₂ to C ₂₀ heterocyclic group and a C ₃ to C ₂₀ cycloalkyl group,

When R ₁ to R ₈ are alkoxyl groups, they may be substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, a silane group, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₂₀ aryl group, a C ₆ to C ₂₀ aryl Group, a C ₂ to C ₂₀ heterocyclic group, and a C ₃ to C ₂₀ cycloalkyl group.

The formula (1) may be represented by the following formula.

In the formula, R ₁ to R ₈ , Ar ₁ and Ar ₂ are as defined in Formula 1.

On the other hand, the formula (1) may be one of the following compounds.

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

Synthetic example

Illustratively, the final products of the present invention are prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1 below.

<Reaction Scheme 1>

One. Sub  1 Synthetic Example

Sub 1 of Scheme 1 can be synthesized by the reaction path of Scheme 2 below.

<Reaction Scheme 2>

Sub  One- 2 synthesis

Sub 1-2 (1 eq.) Was dissolved in DMF in a round bottom flask followed by Bis (pinacolato) diboron (1.1 eq.), Pd (dppf) Cl ₂ (0.03 eq.) And KOAc Lt; / RTI &gt; After completion of the reaction, DMF was removed by distillation, and the mixture was extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was subjected to silicagel column and recrystallization to obtain Sub 1-2.

Sub  One- 3 synthesis

Sub 1 -2 (1 equivalent), bromine compound (1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent) and K ₂ CO ₃ (3 eq.) Obtained in the above synthesis were dissolved in anhydrous THF and a small amount of water , And refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain the desired Sub 1-3

Sub  One- 4 Synthesis

Sub 1-3 obtained in the above synthesis and triphenylphosphine were o-dichlorobenzene enoch and refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain desired Sub 1-4.

Sub  One- 6 synthesis

Sub 1-4 (1 eq.) And Sub 1-5 (1.1 _{equiv), Pd 2 (dba) 3} (0.3 eq.) Obtained in the synthesis, 50% P (t -Bu) 3 (9 eq.), NaO t - Bu (3 eq) was added and stirred at 40 [deg.] 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. Subsequently, the resulting compound was subjected to silicagel column and recrystallization to obtain Sub 1-6.

Sub  One- 7 synthesis

Sub 1-6 (1 eq.) Obtained in the above synthesis was dissolved in DMF in a round bottom flask followed by the addition of Bis (pinacolato) diboron (1.1 eq), Pd (dppf) Cl ₂ (0.03 eq) and KOAc And stirred at 90 [deg.] C. When the reaction was complete, DMF was removed by distillation and extracted 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 1-7.

Sub  One- 8 synthesis

Pd (PPh ₃ ) ₄ (0.03 eq.) And K ₂ CO ₃ (3 eq.) Were reacted with anhydrous THF and a mixture of Sub 1-7 (1 eq.) And R _{5 ~8} Dissolved in a small amount of water, and refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain the desired Sub 1-8.

Sub  1 synthesis

Sub 1-8 and triphenylphosphine obtained in the above synthesis were o-dichlorobenzene enoch and refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired Sub 1.

Examples of Sub 1 include, but are not limited to, the following, and their FD-MSs are shown in Table 1 below.

[Table 1]

2. Sub  Example of 2

Examples of Sub 2 include, but are not limited to, the following FD-MSs.

[Table 2]

3. Product  Synthetic example

To a round bottom flask was added Sub 1 compound (1.2 eq), Sub 2 compound (1 eq), Pd ₂ (dba) ₃ (0.05 eq), P (t-Bu) ₃ (0.1 eq.), NaO t- ) and toluene (10.5 mL / 1 mmol), and the reaction is carried out at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether 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 a product.

Synthetic examples of 1-25

A mixture of 6- (4,6-diphenyl-1,3,5-triazin-2-yl) -5,6-dihydrobenzo [4,5] thieno [2,3- a] carbazole (11.9g, 20mmol) , bromobenzene (3.8g, 24mmol), Pd 2 (dba) 3 (0.03 ~ 0.05 mmol), P (t-Bu) 3 (0.1 equiv), NaO t -Bu (3 eq. ) and toluene (10.5 mL / 1 mmol), and the reaction is carried out at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether 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 9.1 g (yield: 68%) of the product.

Synthetic examples of 1-26

To a round bottom flask was added a solution of 7- (4,6-diphenyl-1,3,5-triazin-2-yl) -7,9-dihydrobenzo [4,5] thieno [2,3- b] carbazole (11.9g, 20mmol) , bromobenzene (3.8g, 24mmol), Pd 2 (dba) 3 (0.03 ~ 0.05 mmol), P (t-Bu) 3 (0.1 equiv), NaO t -Bu (3 eq. ) and toluene (10.5 mL / 1 mmol), and the reaction is carried out at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether 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 9.4 g (yield: 70%) of the product.

Synthetic example of 2-24

To a round bottom flask was added N, N-diphenyl-4- (7-phenyl-7,15-dihydrobenzo [4,5] thieno [2,3- b] indolo [2,3-g] carbazol- (13.6g, 20mmol), bromobenzene ( 3.8g, 24mmol), Pd 2 (dba) 3 (0.03 ~ 0.05 mmol), P (t-Bu) 3 (0.1 equiv), NaO t -Bu (3 eq.), toluene (10.5 mL / 1 mmol), and the reaction is allowed to proceed at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether 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 10.0 g (yield: 66%) of the product.

Synthetic examples of 2-43

A round bottom flask was charged with 8-phenyl-5,8-dihydroindolo [3,2-g] naphtho [1 ', 2': 4,5] thieno [3,2- b] carbazole (9.8 g, 20 mmol), bromobenzene put _{3.8g, 24mmol), Pd 2 (} dba) 3 (0.03 ~ 0.05 mmol), P (t-Bu) 3 (0.1 equiv), NaO t -Bu (3 eq.), toluene (10.5 mL / 1 mmol) Thereafter, the reaction proceeds at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether 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 7.9 g (yield: 70%) of the product.

Synthetic examples of 3-9

A solution of 8-phenyl-8,10-dihydrobenzo [4,5] thieno [3,2-g] indolo [2,3- b] carbazole (8.8 g, 20 mmol), 5-bromo- Pd ₂ (dba) ₃ (0.03-0.05 mmol), P (t-Bu) ₃ (0.1 eq.), NaO t -Bu (3 eq.), toluene (10.5 mL / 1 mmol), diphenylpyrimidine And the reaction proceeds at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether 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 9.1 g (yield: 68%) of the product.

The FD-MS values of the compounds 1-1 to 2-20 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Evaluation of manufacturing of organic electric device

[ Experimental Example  1] Green organic electroluminescent device ( The light-  Phosphorescent host)

An organic electroluminescent device was fabricated according to a conventional method using the compound of the present invention obtained through synthesis as a luminescent host material of a light emitting layer.

First, 4,4 ', 4''- Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited on the ITO layer (anode) Thereby forming a hole injection layer. Subsequently, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as NPD) was vacuum deposited on the hole injection layer to a thickness of 20 nm to form a hole transport layer. Next, a compound of the present invention was doped as a host material on the hole transporting layer and Ir (ppy) 3 [tris (2-phenylpyridine) -iridium] was doped as a dopant in a weight ratio of 95: 5. (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer. Thereafter, LiF as an alkali metal halide was deposited to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode. Thus, an organic electroluminescent device was manufactured.

[ Comparative Example  1] to [ Comparative Example  3]

In Comparative Examples 1 to 3, an organic electroluminescent device was prepared in the same manner as in Experimental Example 1. In Comparative Example 1, Comparative Compound 1 was used instead of the compound of the present invention as a host material of the light emitting layer, Comparative Compound 3 was used instead of the compound of the present invention, and Comparative Example 3 was used in place of the compound of the present invention.

 &Lt; Comparative Compound 1 > CBP < Comparative Compound 2 > < Comparative Compound 3 &

In the embodiment, prepared as examples and comparative examples the organic was applied with a forward bias DC voltage to the electroluminescent device Photo Research (photoresearch) 's were measured and electroluminescence (EL) properties by PR-650, from the measurement result 300cd / m ² based on the luminance The T90 lifetime was measured using a life-time instrument manufactured by McAfee.

Table 4 below shows device fabrication and evaluation results for Experimental Example 1 and Comparative Examples 1 to 3 to which the inventive compound was applied.

[Table 4]

As can be seen from the results of Table 4, the organic electroluminescent device using the organic electroluminescent device material of the present invention can be used as a material for a light emitting layer, thereby remarkably improving high luminous efficiency, low driving voltage and long life.

It can be explained that the chitosan heterocycle compound of the present invention in which the carbazole is fused to the pentasubstituted heterocyclic core has a high thermal stability and a bipolar system, have.

It is obvious that the same effects can be obtained even when the compounds of the present invention are used in other organic layers of an organic electroluminescent device, for example, a hole injecting layer, a hole transporting layer, an electron injecting layer and an electron transporting layer.

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 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.

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 (9)

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

In the above formulas,
Wherein A and B are C ₆ to C ₃₀ aromatic rings,
R ₁ to R ₈ are independently selected from the group consisting of: i) independently of each other hydrogen or -LN (Ar ₃ ) (Ar ₄ ), or ii) R ₁ to R ₈ are adjacent to each other to form at least one C ₆ -C ₆ Or a C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom selected from the group consisting of N, O, S, P and Si (wherein the group which does not form a ring is the same as defined in (i)), ),
Ar ₁ and Ar ₂ are each independently a C ₆ to C ₆₀ aryl group; Or O, N, S, a heterocyclic group of C ₂ ~ containing at least one hetero atom of Si and P C _60,
L is a direct bond; An arylene group having ₆ to ₆₀ carbon atoms; Or O, N, S, Si and P, at least one hetero atom C ₂ ~ of the C ₆₀ heterocyclic ring containing a group of; and, these (direct negative binding) each of a nitro group, a nitrile group, halogen group, C ₁ - an aryl group of C ₂₀ alkyl group, C ₆ ~ C ₂₀ of, C ₂ ~ C heterocyclic group of _20, C ₁ ~ C ₂₀ alkoxy group and amino group may be substituted with one or more substituents selected from the group consisting of and the ,
Ar ₃ and Ar ₄ are each independently a C ₆ to C ₆₀ aryl group; , And; or O, N, S, Si and P, at least one heteroatom of the heterocyclic C ₂ ~ C ₆₀ containing a group
When the Ar ₁ ~ Ar ₄ an aryl group, which is hydrogen, deuterium, a halogen, a silane group, a boron group, a germanium group, a cyano group, a nitro group, C ₁ ~ C ₂₀ coming of the alkylthio, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of alkenyl groups _{(alkenyl), C 2 ~ C} 20 of the alkynyl group (alkynyl), a C ₆ substituted with an aryl group, a heavy hydrogen of C ₆ ~ C ₂₀ of - of C ₂₀ aryl group, C ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ of the An arylalkyl group, and an arylalkenyl group having ₈ to ₂₀ carbon atoms,
Wherein Ar ₁ ~ Ar ₄ is, if the heterocyclic group, which is hydrogen, deuterium, a halogen, a silane group, a cyano group, an alkyl group of a nitro group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ of, C ₂ ~ C ₂₀ A C ₆ to C ₂₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₂ to C ₂₀ heterocyclic group, a C ₃ to C ₂₀ cycloalkyl group, a C ₇ to C ₂₀ aralkyl group, ~ C ₂₀ An arylalkyl group and an arylalkenyl group having from ₈ to ₂₀ carbon atoms. The method according to claim 1,
Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;

(Wherein R ₁ to R ₈ , Ar ₁ and Ar ₂ are the same as defined in Formula 1) The method according to claim 1,
Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;

An organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode,
Wherein the organic material layer contains the compound of any one of claims 1 to 3. 5. The method of claim 4,
Wherein said compound is formed into said organic material layer by a soluble process. 5. The method of claim 4,
Wherein the organic material layer includes at least one of a light emitting layer, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, an electron injecting layer, and an electron transporting layer. The method according to claim 6,
Wherein the light emitting layer comprises the compound. A display device including the organic electroluminescent device of claim 4; And
A controller for driving the display device; &Lt; / RTI &gt; 9. The method of claim 8,
Wherein the organic electronic device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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