WO2014142467A1 - Compound for organic electronic element, organic electronic element using compound, and electronic device comprising organic electronic element - Google Patents

Abstract

The present invention provides a novel compound which enables an element to have improved luminous efficiency and stability, and an increased lifespan, an organic electronic element using the compound, and an electronic device comprising the organic electronic element.

Description

Compound for organic electric element, organic electric element using same and electronic device thereof

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

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

The material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

On the other hand, it delays the diffusion of metal oxide into the organic layer from the anode electrode (ITO), which is one of the causes of shortening the life of the organic electronic device, and stable characteristics, that is, high glass transition even for Joule heating generated when driving the device. There is a need for development of a hole injection layer material having a temperature. 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.

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, high heat resistance, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by the following formula (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, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and color purity and life of the device can be greatly improved.

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

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings.

In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, in describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

On the other hand, the terms "halo" or "halogen" as used herein include fluorine, chlorine, bromine, and iodine unless otherwise stated.

As used herein, the term "alkyl" or "alkyl group" has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.

As used herein, the term "alkenyl" or "alkynyl" has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.

The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

The term "alkoxy group" used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.

As used herein, the terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.

In the present invention, an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group, a spirobifluorene group.

As used herein, the term “heteroalkyl” means an alkyl including one or more heteroatoms unless otherwise indicated. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or arylene group having 2 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. And not only a single ring but also multiple rings, and adjacent groups may be formed by bonding.

As used herein, the terms "heterocycloalkyl", "heterocyclic group" includes one or more heteroatoms, unless otherwise indicated, having from 2 to 60 carbon atoms, including single rings as well as multiple rings Adjacent groups may be formed in combination. In addition, "heterocyclic group" may mean an alicyclic and / or aromatic including a heteroatom.

As used herein, the term “heteroatom” refers to N, O, S, P, and Si unless otherwise indicated.

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

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

Other heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.

Also, unless stated otherwise, the term "substituted" in the term "substituted or unsubstituted" as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy groups, C ₁ to C ₂₀ alkylamine groups, C ₁ to C ₂₀ alkylthiophene groups, C ₆ to C ₂₀ arylthiophene groups, C ₂ to C ₂₀ alkenyl groups, C ₂ to C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ aryl alkenyl group, silane group, boron Group, germanium group, and C ₂ ~ C _{20 It} is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.

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

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110. ) Is provided with an organic material layer containing a compound according to the present invention. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. The hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.

In addition, although not shown, the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD method. For example, the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on the substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting auxiliary layer 151, and the light emitting layer thereon. After forming the organic material layer including the 150, the electron transport layer 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.

In addition, the organic material layer using a variety of polymer materials is less by a solution process or solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition It can be prepared in a number of layers. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.

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

In addition, the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, 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. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the compound which concerns on one aspect of this invention is demonstrated.

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

<Formula 1>

In the above formula,

A and B are C ₆ ~ C ₃₀ An aromatic ring,

R ₁ to R ₈ are each independently hydrogen; heavy hydrogen; Tritium; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₆₀ aryloxy group; C ₃ -C ₆₀ cycloalkyl group; And -LN (Ar ₃ ) (Ar ₄ ); may be selected from the group consisting of.

In addition, R ₁ to R ₈ may combine with each other to form at least one ring. At this time, the group that does not form a ring may be defined the same as defined above.

Adjacent groups of R ₁ to R ₈ combine with each other to form at least one ring: 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 the adjacent groups are bonded to each other to form a ring, the scope of the present invention is not limited by what substituents and by what reaction the ring is formed.

The ring formed by bonding of neighboring groups to each other among R ₁ to R ₈ may be a heterocyclic ring containing at least one aromatic ring or a heteroatom of a single ring or multiple rings, and may also be a fused form of an aromatic ring and an aliphatic ring. have. For example, neighboring groups of R ₁ to R _{8 may} be bonded to each other to form an aromatic ring such as benzene, naphthalene, phenanthrene, and the like, and the number of nuclear carbons in the aromatic ring 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 are bonded to each other to form a benzene ring, a phenanthrene form may be formed together with the benzene ring of the parent nucleus to which they are bonded.

Ar ₁ and Ar ₂ are each independently a C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; And -LN (Ar ₃ ) (Ar ₄ ); may be selected from the group consisting of.

L is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And divalent aliphatic hydrocarbon group; may be selected from the group consisting of. In addition, each of these (except for a single bond) may be a nitro group, a nitrile group, a halogen group, an alkyl group of C ₁ to C ₂₀ , an aryl group of C ₆ to C ₂₀ , a heterocyclic group of C ₂ to C ₂₀ , and C ₁ to C It may be substituted with one or more substituents selected from the group consisting of ₂₀ alkoxy groups and amino groups.

Ar ₃ and Ar ₄ independently of each other C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And C ₁ ~ C ₅₀ Alkyl group; may be selected from the group consisting of.

Each of the aryl group, heterocyclic group, fluorenyl group, alkyl group, cycloalkyl group, alkenyl group, aryloxy group and alkoxyl group is deuterium; halogen; Silane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ ~ C ₂₀ of the import alkylthio; C ₁ -C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; Alkenyl of C ₂ to C ₂₀ ; C ₂ ~ C ₂₀ Alkynyl (alkynyl); C ₆ -C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₂ ~ C ₂₀ heterocyclic group; C ₃ -C ₂₀ cycloalkyl group; Of C ₇ ~ C ₂₀ Arylalkyl group; And C ₈ ~ C ₂₀ It may be substituted with one or more substituents selected from the group consisting of; arylalkenyl group.

Here, in the case of the aryl group, the carbon number may be 6 to 60, preferably 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms,

When the heterocyclic group has 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably a hetero ring having 2 to 20 carbon atoms,

In the case of the arylene group, the carbon number may be 6 to 60, preferably 6 to 30 carbon atoms, more preferably an arylene group having 6 to 20 carbon atoms,

In the case of the alkyl group, the carbon number is 1 to 50, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably an alkyl group having 1 to 10 carbon atoms.

Formula 1 may be represented by the following formula.

At this time, in the formula, R ₁ to R ₈ , Ar ₁ And Ar ₂ It may be defined the same as defined in the formula (1).

On the other hand, Formula 1 may be one of the following compounds.

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

Synthesis Example

For example, the compounds according to the present invention may be prepared by reacting Sub 1 and Sub 2 as in Scheme 1, but are not limited thereto.

<Scheme 1>

One. Sub  Synthesis Example of 1

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.

<Scheme 2>

Sub  One- 2 synthetic

Sub 1-2 (1 equiv) was dissolved in DMF in a round bottom flask, then Bis (pinacolato) diboron (1.1 equiv), Pd (dppf) Cl ₂ (0.03 equiv) and KOAc (3 equiv) were added at 90 ° C. Stirred at. After completion of the reaction, DMF was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was purified by silicagel column and recrystallized to obtain Sub 1-2.

Sub  One- 3 synthetic

Sub 1-2 (1 equivalent), bromine compound (1 equivalent), Pd (PPh ₃ ) ₄ (0.03 equivalent), and K ₂ CO ₃ (3 equivalent) obtained in the above synthesis were dissolved in anhydrous THF and a small amount of water. It was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. After removing a small amount of water with anhydrous MgSO ₄ and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired Sub 1-3.

Sub  One- 4 synthetic

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

Sub  One- 6 synthetic

Sub 1-4 (1 equivalent) and Sub 1-5 (1.1 equivalent), Pd ₂ (dba) ₃ (0.3 equivalent), 50% P ( t- Bu) ₃ (9 equivalent), NaO t − obtained in the above synthesis Bu (3 equiv) was added and stirred at 40 ° C. After the reaction was completed, 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 purified by silicagel column and recrystallized to obtain Sub 1-6.

Sub  One- 7 synthetic

Sub 1-6 (1 equivalent) obtained in the above synthesis was dissolved in DMF in a round bottom flask, followed by addition of Bis (pinacolato) diboron (1.1 equiv), Pd (dppf) Cl ₂ (0.03 equiv) and KOAc (3 equiv) And stirred at 90 ° C. After the reaction was completed, DMF was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was subjected to silicagel column and recrystallization to obtain Sub 1-7.

Sub  One- 8 synthetic

Anhydrous THF a Sub 1-7 (1 eq.) With the bromine compound (1 _{eq), Pd (PPh 3) 4} (0.03 eq), K ₂ CO _{3 (3} eq) substituted by R _{5 ~ 8} obtained in the above synthesis and After dissolving in a small amount of water, it was refluxed for 24 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, and the organic solvent was concentrated. The resulting product was separated by column chromatography to obtain the desired Sub 1-8.

Sub  1 synthetic

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

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

TABLE 1

2. Sub  Example of 2

Examples of Sub 2 in Scheme 1 are as follows, but are not limited thereto, and their FD-MS are shown in Table 2 below.

TABLE 2

3. Product  Synthesis Example

Sub 1 compound (1.2 equiv), Sub 2 compound (1 equiv), Pd ₂ (dba) ₃ (0.05 equiv), P (t-Bu) ₃ (0.1 equiv), NaO t -Bu (3 equiv) in a round bottom flask ), add toluene (10.5 mL / 1 mmol) and proceed with the reaction at 100 ℃. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was silicagel column and recrystallized to obtain a product product.

Synthesis Example of 1-25

6- (4,6-diphenyl-1,3,5-triazin-2-yl) -5,6-dihydrobenzo [4,5] thieno [2,3-g] indolo [2,3- in a round bottom flask 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 equiv ), add toluene (10.5 mL / 1 mmol) and proceed with the reaction at 100 ℃. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 9.1g (yield: 68%).

Synthesis Example of 1-26

7- (4,6-diphenyl-1,3,5-triazin-2-yl) -7,9-dihydrobenzo [4,5] thieno [2,3-g] indolo [2,3- in a round bottom flask 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 equiv ), add toluene (10.5 mL / 1 mmol) and proceed with the reaction at 100 ℃. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 9.4 g (yield: 70%) of the product.

Synthesis Example of 2-24

N, N-diphenyl-4- (7-phenyl-7,15-dihydrobenzo [4,5] thieno [2,3-b] indolo [2,3-g] carbazol-3-yl) aniline in a round bottom flask (13.6 g, 20 mmol), bromobenzene (3.8 g, 24 mmol), Pd ₂ (dba) ₃ (0.03-0.05 mmol), P (t-Bu) ₃ (0.1 equiv), NaO t -Bu (3 equiv), toluene (10.5 mL / 1 mmol) was added and the reaction was performed at 100 ° C. After completion of the reaction, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 10.0 g (yield: 66%) of the product.

Synthesis Example of 2-43

8-phenyl-5,8-dihydroindolo [3,2-g] naphtho [1 ', 2': 4,5] thieno [3,2-b] carbazole (9.8 g, 20 mmol), bromobenzene ( 3.8 g, 24 mmol), Pd ₂ (dba) ₃ (0.03-0.05 mmol), P (t-Bu) ₃ (0.1 equiv), NaO t -Bu (3 equiv), toluene (10.5 mL / 1 mmol) After the reaction proceeds at 100 ℃. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic substance was purified by silicagel column and recrystallized to obtain the product 7.9g (yield: 70%).

Synthesis Example of 3-9

8-phenyl-8,10-dihydrobenzo [4,5] thieno [3,2-g] indolo [2,3-b] carbazole (8.8 g, 20 mmol), 5-bromo-2,4- in a round bottom flask diphenylpyrimidine (7.5 g, 24 mmol), Pd ₂ (dba) ₃ (0.03-0.05 mmol), P (t-Bu) ₃ (0.1 equiv), NaO t -Bu (3 equiv), toluene (10.5 mL / 1 mmol) After the reaction proceeds at 100 ℃. After the reaction was completed, the mixture was extracted with ether and water, the organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was purified by silicagel column and recrystallized to obtain 9.1g (yield: 68%).

On the other hand, FD-MS values of the compounds 1-1 to 1-48, 2-1 to 2-48 and 3-1 to 3-48 of the present invention prepared according to the synthesis examples as described above are shown in Table 3.

TABLE 3

Manufacturing Evaluation of Organic Electrical Device

[ Example  1] Green organic light emitting device Light emitting layer  Phosphorescent host)

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

First, 4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as" 2-TNATA ") was vacuum deposited on an ITO layer (anode) formed on an organic substrate. A hole injection layer was formed, and then 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as "NPD") was vacuumed to a thickness of 20 nm on the hole injection layer. And deposited to form a hole transport layer Next, the compound 1-1 of the present invention was used as a host material on the hole transport layer and tris (2-phenylpyridine) -iridium (hereinafter referred to as "Ir (ppy) ₃ ") as a dopant material. And a light emitting layer deposited at a thickness of 30 nm by doping at a weight ratio of 95: 5, followed by (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) on the light emitting layer. Aluminum (hereinafter abbreviated as "BAlq") is vacuum deposited to a thickness of 10 nm to form a hole blocking layer, and abbreviated as tris (8-quinolinol) aluminum (hereinafter referred to as "Alq ₃ ") on the hole blocking layer. 40nm two Then, an electron transport layer was formed, and then an organic electroluminescent device was manufactured by depositing LiF, which is a halogenated alkali metal, to a thickness of 0.2 nm to form an electron injection layer, and then depositing Al to a thickness of 150 nm to form a cathode. .

[Example 2] to [Example 144] green organic electroluminescent device (light emitting layer phosphorescent host)

Use of one of compounds 1-2 to 1-48, 2-1 to 2-48, and 3-1 to 3-48 of the present invention shown in Table 4 below as a host material of the light emitting layer. An organic electroluminescent device was manufactured in the same manner as in Example 1 except for the above.

Comparative Example 1

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used instead of Compound 1-1 of the present invention as a host material of the emission layer.

<Comparative Compound 1>

Comparative Example 2

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used instead of Compound 1-1 of the present invention as a host material of the emission layer.

Comparative Compound 2

Comparative Example 3

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 3 was used instead of Compound 1-1 of the present invention as a host material of the emission layer.

Comparative Compound 3

The electroluminescence (EL) characteristics of the organic electroluminescent devices of Examples 1 to 144 and Comparative Examples 1 to 3 thus prepared were subjected to a forward bias DC voltage to the photoresearch company, PR-650, to measure electroluminescence (EL) characteristics. , T90 life was measured using a life-time measuring instrument manufactured by McScience Inc. at 300 cd / m ² reference luminance. The measurement results are shown in Table 4 below.

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 light emitting layer material can significantly improve the high luminous efficiency, low driving voltage and lifespan.

This can be explained that the compound of the present invention has a high thermal stability and bipolar (bipolar) system is formed to increase the driving, efficiency, life.

Even if the compounds of the present invention are used in other organic material layers of the organic electroluminescent device, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, it is obvious that the same effect can be obtained.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains may various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments.

The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.

[Description of the code]

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

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority under No. 10-2013-0025511 of Patent Application No. 10-2013-0025511, filed in Korea on March 11, 2013, pursuant to section 35 of US Patent § 119 (a). All content is incorporated by reference in this patent application. In addition, if this patent application claims priority for the same reason for countries other than the United States, all its contents are incorporated into this patent application by reference.

Claims (9)

1. A compound represented by the following formula (1).

   <Formula 1>

   

   [In the above formula,

   A and B are C ₆ ~ C ₃₀ An aromatic ring,

   R ₁ to R ₈ are, independently from each other, i) hydrogen; heavy hydrogen; Tritium; C ₆ ~ C ₆₀ Aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₁ -C ₃₀ alkoxyl group; C ₆ -C ₆₀ aryloxy group; C ₃ -C ₆₀ cycloalkyl group; And -LN (Ar ₃ ) (Ar ₄ ); or ii) neighboring groups may combine with each other to form at least one ring (wherein the group that does not form a ring is in i) As defined),

   Ar ₁ and Ar ₂ are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; C ₁ ~ C ₅₀ Alkyl group; And -LN (Ar ₃ ) (Ar ₄ ); It can be selected from the group consisting of,

   L is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And divalent aliphatic hydrocarbon group; may be selected from the group consisting of, each of these (except a single bond) is a nitro group, a nitrile group, a halogen group, a C ₁ ~ C ₂₀ alkyl group, C ₆ ~ C ₂₀ aryl group, It may be substituted with one or more substituents selected from the group consisting of C ₂ ~ C ₂₀ heterocyclic group, C ₁ ~ C ₂₀ Alkoxy group and amino group,

   Ar ₃ and Ar ₄ independently of each other C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And it may be selected from the group consisting of; C ₁ ~ C ₅₀ Alkyl group,

   Each of the aryl group, heterocyclic group, fluorenyl group, alkyl group, cycloalkyl group, alkenyl group, aryloxy group and alkoxyl group is deuterium; halogen; Silane group; Boron group; Germanium group; Cyano group; Nitro group; C ₁ ~ C ₂₀ of the import alkylthio; C ₁ -C ₂₀ alkoxyl group; C ₁ ~ C ₂₀ Alkyl group; Alkenyl of C ₂ to C ₂₀ ; C ₂ ~ C ₂₀ Alkynyl (alkynyl); C ₆ -C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₂ ~ C ₂₀ heterocyclic group; C ₃ -C ₂₀ cycloalkyl group; Of C ₇ ~ C ₂₀ Arylalkyl group; And C ₈ ~ C ₂₀ An arylalkenyl group; may be substituted with one or more substituents selected from the group consisting of.]
2. The method of claim 1,

   Compound represented by one of the following formula.

   

   

   (In the above formula, R ₁ to R ₈ , Ar ₁ and Ar ₂ may be defined the same as defined in claim 1.)
3. The method of claim 1,

   Compounds, characterized in that one of the formula.

   

   

   

   

   

   
4. In an organic electric device comprising a first electrode, a second electrode, and an organic material layer positioned between the first electrode and the second electrode,

   The organic material layer comprises an organic electroluminescent device comprising the compound of claim 1.
5. The method of claim 4, wherein

   And forming the compound into the organic material layer by a soluble process.
6. The method of claim 4, wherein

   The organic material layer comprises at least one of a light emitting layer, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, an electron injection layer and an electron transport layer.
7. The method of claim 6,

   The light emitting layer is an organic electroluminescent device comprising the compound.
8. Claim 4 display device comprising the organic electroluminescent element; And

   A controller for driving the display device; Electronic device comprising a.
9. The method of claim 8,

   The organic electronic device is at least one of an organic electroluminescent device, an organic solar cell, an organic photosensitive member, an organic transistor, and a device for monochrome or white illumination.

Images