KR101986172B1 - Novel compound for organic electronic element, organic electronic element using the same, and a 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

TECHNICAL FIELD [0001] The present invention relates to a novel compound for organic electroluminescent devices, an organic electroluminescent device using the same, and an electronic device using the same. BACKGROUND ART < RTI ID = 0.0 >

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

Mr. Eastman Kodak of the 1980s. W. CW Tang et al. Have made organic electroluminescent devices using organic materials practical by developing a laminated structure device in which various roles are shared among various materials. In order to obtain a high luminance of more than 1000 cd / m ^{2 at} a voltage of 10 V or lower by laminating a phosphor capable of transporting electrons and an organic material capable of transporting holes and injecting both charges into the phosphor layer Respectively.

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.

Particularly, various studies have been conducted on organic materials inserted into a hole transporting layer or a buffer layer for an excellent lifetime characteristic of an organic electric device. To this end, a high hole transporting property from an anode to an organic layer is given, A hole injection layer material having high uniformity and low crystallinity is required.

It is possible to delay penetration and diffusion of the metal oxide from the anode electrode (ITO), which is one of the causes of shortening the lifetime of the organic electronic device, and to stabilize the joule heating caused by driving the device, Lt; RTI ID = 0.0 > layer < / RTI > 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.

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 is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In order to 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 novel compound capable of improving the high luminous efficiency, low driving voltage, color purity, and service life of the device, and an organic electronic device using the novel compound and an electronic device thereof.

In order to accomplish the object of the present invention as described above, the present invention provides a carbazole compound having a substituent group containing a diarylamine group at the 2-position thereof. These compounds include a hole injecting material, a hole transporting material, Emitting material and / or a passivation (keping) material, and is particularly useful alone as a light emitting material, a host, a dopant, a hole injecting layer, and a hole transporting layer.

More particularly, the present invention relates to a compound represented by the following formula (1) for solving the above problems of the prior art and achieving the object of the present invention of improving the luminous efficiency, the driving voltage, the color purity, to provide.

In Formula 1,

1) Ar ₁ Is phenyl; Biphenyl; A 1-naphthyl group; A 2-naphthyl group; An aryl group of C ₆ to C ₆₀ , and a heterocyclic group of C ₅ to C ₂₀ , which is unsubstituted or substituted with at least one substituent selected from the group consisting of Pyridine; A pyrimidine substituted with at least one substituent selected from the group consisting of an aryl group of C ₆ to C _{60 and} a heterocyclic group of C ₅ to C ₂₀ ; An aryl group having ₆ to ₆₀ carbon atoms, a heterocyclic group having ₅ to ₂₀ carbon atoms, or a substituted or unsubstituted triazine group;

2) Ar ₂ To Ar ₄ are the same or different and represents hydrogen, deuterium, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ of the alkyl amine group, alkyl thiophene group of _{C 1 ~ C 20, C 6} ~ C 20 aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C of ₆ ~ C ₆₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, a C ₈ ~ C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, consisting of a heterocycle of the C ₅ ~ C ₂₀ of A C ₆ -C ₆₀ aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of A halogen atom, a halogen atom, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl Membered heterocyclic group, a nitrile group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, substituted with one or more substituents from the group or unsubstituted, and O, N, and optionally substituted with at least one of S or unsubstituted C ₅ ~ C ₆₀ heteroaryl group; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group ; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group substituted or unsubstituted C ₆ ~ C ₃₀ aryloxy group as; A halogen group, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ of the cycloalkyl group, C ₂ ~ C heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ C of the arylamine group with one or more substituents selected from the ₆₀ heteroaryl group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ of _30; C alkyl group of ₁ ~ C _20, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ aryl group of C ₂₀ aryl group, a C ₂ ~ C ₂₀ substituted with deuterium, C ₈ of alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ to be.

Ar ₃ and Ar ₄ may combine with adjacent groups to form a saturated or unsaturated aliphatic ring or a heterocyclic ring.

3) L is nitro, nitrile, a halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and by one or more substituents selected from the group consisting of amino group-substituted or unsubstituted C ₆ ~ C ₆₀ of An arylene group ; A heteroaryl group of nitro, nitrile, halogen, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group and by one or more substituents selected from the group consisting of amino group-substituted or unsubstituted C ₅ ~ C ₆₀ of; And Or a divalent substituted or unsubstituted aliphatic hydrocarbon .

More specifically, the present invention provides a compound represented by any one of the compounds represented by the general formulas (1) to (5). Wherein Ar ₁ to Ar ₄ are the same as defined in Formula 1 above.

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

The term " halo " or " halogen ", as used herein, unless otherwise indicated, includes fluorine, chlorine, bromine, and iodine.

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.

The term " heteroalkyl ", as used herein, unless otherwise indicated, means alkyl having one or more heteroatoms.

As used herein, the term " heteroaryl group " or " heteroarylene group " means an aryl or arylene group of 3 to 60 carbon atoms having one or more heteroatoms, respectively, It is not.

The term " heterocycloalkyl ", " heterocyclic group ", as used herein, unless otherwise stated, includes one or more heteroatoms and has from 2 to 60 carbon atoms.

As used herein, the term " heteroatom " means N, O, S, P and 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.

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 halogen atom, a germanium group, and a C ₅ to C ₂₀ heterocyclic group.

More specifically, the compounds represented by the above formulas (1) to (5) are selected from the following compounds (P2-1) to (P5-84), but are not limited thereto.

The compounds represented by Formula 1 may be one of the compounds shown in Formula 6, but are not limited thereto. Here, the substituents of the compounds represented by the formula (1) are exemplified as typical compounds since it is practically difficult to exemplify all the compounds in a wide range of relation. However, the compounds represented by the formula (1) You can configure some.

By using the novel compounds according to the present invention, it is possible to remarkably improve the luminous efficiency, the driving voltage, the color purity, and the lifetime of the device.

1 to 6 show examples of organic electroluminescent devices to which the compounds of the present invention can be applied.

The compounds according to the invention having the above formula can be used in a soluble process. In other words, the above-mentioned combination can form an organic layer of an organic electronic device to be described later by a solution process. That is, when the compound is used as an organic material layer, the organic material layer may be formed by a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Lt; RTI ID = 0.0 > a < / RTI > fewer layers.

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

Example

Hereinafter, the present invention will be described in more detail with reference to Production Examples and Experimental Examples. However, the following Preparation Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Manufacturing example

Hereinafter, preparation examples or synthesis examples of the compounds belonging to the formula 1 will be described. However, since the number of the compounds belonging to the formula (1) is large, some of the compounds belonging to the formula (1) will be exemplarily explained. Those skilled in the art, that is, those skilled in the art, can prepare the compounds belonging to the present invention which are not illustrated through the following production examples.

General synthesis method

The synthesis of the compound was carried out as follows.

Sub 1-1 Synthesis method Example (2- Bromocarbazole )

Synthesis of Intermediate 1 (4-Bromo-2-nitrobiphenyl)

To a 2 L round bottom flask was added toluene (500 mL), phenyl boronic acid (20 g, 164 mmol), 2,5-ibromonitrobenzene (46.2 g, 164.6 mmol), Pd (PPh ₃ ) ₄ (5.6 g, Add Na ₂ CO ₃ aqueous solution (248 mL). Then, the mixture is heated under reflux at 90 DEG C for 6 hours. When the reaction is complete, dilute with distilled water at room temperature. The mixture was extracted with methylene chloride and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting compound was purified by silicagel column (methylene chloride: hexane = 1: 1) to obtain 38.4 g (84.2%) of product.

Synthesis of Sub 1-1 (2-Bromocarbazole)

4-Bromo-2-nitrobenzene (38.4 g, 138.08 mmol) and triethylphosphate (168 mL, 966.56 mmol) were added to a 250 mL round bottom flask and the mixture was refluxed at 160 ° C to 165 ° C for 14 hours. After the reaction is completed, the remaining triethylphosphite is removed by distillation under reduced pressure, diluted with a mixed solvent of MeOH: H ₂ O = 1: 1, and the resulting solid is filtered. The resulting solid is washed with a mixed solvent of MeOH: H ₂ O = 1: 1 and petroleum ether.

The solid is dissolved in methylene chloride, dried over MgSO ₄ , concentrated and silicagel column. (60%) of the product (petroleum ether: methylene chloride = 2: 1).

 Sub 1-2 Synthesis method Example: Ar _One = phenyl when  (2- Bromo -9-phenyl carbazole )

2-Bromocarbazole (18 g, 73.14 mmol), iodobenzene (29.85 g, 146.28 mmol), K ₂ CO ₃ (30.33 g, 219.42 mmol), Cu powder (4.65 g, 73.14 mmol), 18- -6 (9.66 g, 36.57 mmol) and o-dichlorobenzene (450 mL), and the mixture was refluxed for 24 hours. After completion of the reaction, the reaction mixture is extracted with methylene chloride and water, and the obtained organic layer is washed with 5% hydrochloric acid and brine. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give 16.5 g (70%) of the product.

Sub 1-2 illustrate the synthesis method: Ar = ₁ when Biphenyl (9- (biphenyl-4- yl) -2- bromo -9H- carbazole)

2-Bromocarbazole (18 g, 73.14 mmol) in a 2L round bottom flask, 4-iodobiphenyl (40.97 g, 146.28 mmol), K 2 CO 3 (30.33 g, 219.42 mmol), Cu powder (4.65 g, 73.14 mmol), 18 -crown-6 (9.66 g, 36.57 mmol) and o-dichlorobenzene (450 mL), and the mixture is refluxed for 24 hours. After completion of the reaction, the reaction mixture is extracted with methylene chloride and water, and the obtained organic layer is washed with 5% hydrochloric acid and brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give 20.1 g (69%) of the product.

Sub 1-2 synthesis example: Ar ₁ = 1- naphtyl When (2- bromo -9- (naphthalen -1- yl ) - 9H-carbazole)

2-Bromocarbazole (18 g, 73.14 mmol), 1-iodonaphthalene (37.17 g, 146.28 mmol), K ₂ CO ₃ (30.33 g, 219.42 mmol), Cu powder (4.65 g, 73.14 mmol) -crown-6 (9.66 g, 36.57 mmol) and o-dichlorobenzene (450 mL), and the mixture is refluxed for 24 hours. After completion of the reaction, the reaction mixture is extracted with methylene chloride and water, and the obtained organic layer is washed with 5% hydrochloric acid and brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give 19.33 g (71%) of product.

Sub 1-2 synthesis example: Ar ₁ = 2- naphtyl When (2- bromo -9- (naphthalen -2- yl ) - 9H-carbazole)

2-iodonaphthalene (37.17 g, 146.28 mmol), K ₂ CO ₃ (30.33 g, 219.42 mmol), Cu powder (4.65 g, 73.14 mmol), 18 -crown-6 (9.66 g, 36.57 mmol) and o-dichlorobenzene (450 mL), and the mixture is refluxed for 24 hours. After completion of the reaction, the reaction mixture is extracted with methylene chloride and water, and the obtained organic layer is washed with 5% hydrochloric acid and brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to obtain 18.51 g (68%) of product.

Sub 1-2 illustrate the synthesis method: Ar = ₁ when Pyridine (2- bromo -9- (pyridin -2- yl ) -9H- carbazole)

2-bromocarbazole (18 g, 73.14 mmol), 2-iodopyridine (30 g, 146.28 mmol), K ₂ CO ₃ (30.33 g, 219.42 mmol), Cu powder (4.65 g, 73.14 mmol), 18 -crown-6 (9.66 g, 36.57 mmol) and o-dichlorobenzene (450 mL), and the mixture is refluxed for 24 hours. After completion of the reaction, the reaction mixture is extracted with methylene chloride and water, and the obtained organic layer is washed with 5% hydrochloric acid and brine. The organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give 15.36 g (65%) of the product.

Sub 1-2 illustrate the synthesis method: Ar ₁ = Pyrimidine when (2- bromo -9- (pyrimidin -5- yl ) - 9H-carbazole)

2-Bromocarbazole (18 g, 73.14 mmol), 5-iodopyrimidine (30.13 g, 146.28 mmol), K ₂ CO ₃ (30.33 g, 219.42 mmol), Cu powder (4.65 g, 73.14 mmol) -crown-6 (9.66 g, 36.57 mmol) and o-dichlorobenzene (450 mL), and the mixture is refluxed for 24 hours. After completion of the reaction, the reaction mixture is extracted with methylene chloride and water, and the obtained organic layer is washed with 5% hydrochloric acid and brine. The organic layer was dried over MgSO ₄ and concentrated. The obtained compound was purified by silicagel column (ethyl acetate: hexane = 1: 1) to obtain 15.65 g (66%) of the product

Sub 1-3 compounds

Sub 1-3 synthesis example ( N, 9 - 피덴 -9H- carbazole -2-amine)

Pd ₂ (dba) ₃ (1.28 g, 1.4 mmol), PPh ₃ (1.22 g, 4.7 mmol) and Na ₂ O (0.45 g, t- Bu (13.42 g, 140 mmol) were added, respectively, and the mixture was refluxed with stirring at 100 ° C for 24 hours. 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 11.68 g (75%) of the product.

Sub-1-3-1 ~ 1-3-25 were synthesized by the same method as above, and the product was confirmed by FD-MS as shown in the following table.

Sub 2-1 Compound

Sub 2-1-1 Synthetic method example ( diphenylamine )

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol), PPh ₃ (1.31 g, 5 mmol) and NaO t -butyl alcohol were added to a mixture of aniline (4.66 g, 50 mmol) and bromobenzene Bu (14.42 g, 150 mmol) was added thereto, and the mixture was refluxed with stirring at 100 ° C for 24 hours. 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 6.26 g (74%) of the product.

Sub 2-1-2 Synthetic method example (N- 페 phenylnaphthalen -1-amine)

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol), PPh ₃ (1.31 g, 5 mmol), NaO ₂ (diboronitrile) were added to a mixture of aniline (4.66 g, 50 mmol) and 1-bromonaphthalene t- Bu (14.42 g, 150 mmol), respectively, and the mixture is refluxed at 100 ° C for 24 hours. 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 8.11 g (74%) of the product.

Sub 2-1-3 Synthetic method example ( dinaphthalen -One- ylamine )

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol), PPh ₃ (1.31 g, 5 mmol) was added to a mixture of 480 mL of toluene and then 1-bromonaphthalene (11.39 g, 55 mmol) mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 9.7 g (72%) of the product.

Sub 2-1-4 Synthetic method example (N- ( naphthalen -2- yl ) naphthalen -1-amine)

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol) and PPh ₃ (1.31 g, 5 mmol) were added to a mixture of 480 mL of toluene, followed by the addition of naphthalen-1-amine (7.16 g, 50 mmol) and 2-bromonaphthalene mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 9.7 g (72%) of the product.

Sub 2-1-5 Synthetic method example ( dinaphthalen -2- ylamine )

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol) and PPh ₃ (1.31 g, 5 mmol) were added to a mixture of 480 mL of toluene, followed by the addition of naphthalen-2-amine (7.16 g, 50 mmol) and 2-bromonaphthalene mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 9.56 g (71%) of the product.

Sub 2-1-6 Synthetic method example ( 디ıbiphenyl -4- ylamine )

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol), PPh ₃ (1.31 g, 5 mmol) was added to 480 mL of toluene after biphenyl-4-amine (8.46 g, 50 mmol) and 4-bromobiphenyl mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 12.05 g (75%) of the product.

Sub 2-1-7 illustrates synthesis (N- (biphenyl-4- yl) -9,9- dimethyl -9H- fluoren -2- amine)

biphenyl-4-amine (8.46 g , 50 mmol) and 2-bromo-9,9-dimethyl- 9H-fluorene (15.02 g, 55 mmol) then the mixture in toluene _{480mL Pd 2 (dba) 3 (} 1.37 g, 1.5 mmol), PPh ₃ (1.31 g, 5 mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 12.65 g (70%) of the product.

Sub 2-1-8 illustrates synthesis (N- (biphenyl-4- yl) -9,9- diphenyl -9H- fluoren -2- amine)

biphenyl-4-amine (8.46 g , 50 mmol) and 2-bromo-9,9-diphenyl- 9H-fluorene (21.85 g, 55 mmol) then the mixture in toluene _{480mL Pd 2 (dba) 3 (} 1.37 g, 1.5 mmol), PPh ₃ (1.31 g, 5 mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 16.51 g (68%) of the product.

Sub 2-1-9 Synthetic method example (N- (biphenyl-4-yl) dibenzo [ b, d ] thiophen -2-amine)

(dba) ₃ (1.37 g, 1.5 mmol), PPh (dibutylphosphine) palladium ( _II ), and triethylamine were added to a mixture of 480 mL of toluene, followed by the addition of 3-bromodibenzo [b, d] thiophene (8.46 g, ₃ (1.31 g, 5 mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 12.13 g (69%) of the product.

Sub 2-1-10 Synthetic method example (N- (biphenyl-4- yl ) naphthalen -2-amine)

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol) and PPh ₃ (1.31 g, 5 mmol) were added to a mixture of 480 mL of biphenyl-4-amine (8.46 g, 50 mmol) and 2-bromonaphthalene mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 10.78 g (73%) of the product.

Sub 2-1-11 Synthetic method example (N- (4- ( naphthalen -One- yl ) phenyl) biphenyl-4-amine)

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol) and PPh ₃ (1.5 mmol) were added to a mixture of 480 mL of toluene after adding biphenyl-4-amine (8.46 g, 50 mmol) and 1- (4- bromophenyl) naphthalene (1.31 g, 5 mmol) and NaO t- Bu (14.42 g, 150 mmol), respectively, and the mixture is refluxed at 100 ° C for 24 hours. 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 13 g (70%) of the product.

Sub 2-1-12 Synthesis Example (N- (4- methoxyphenyl ) biphenyl-4-amine)

biphenyl-4-amine (8.46 g , 50 mmol) and 1-bromo-4-methoxybenzene ( 10.29 g, 55 mmol) the later mixed in toluene _{480mL Pd 2 (dba) 3 (} 1.37 g, 1.5 mmol), PPh 3 ( 1.31 g, 5 mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 10.33 g (75%) of the product.

Sub 2-1-13 Synthetic method example (N- (4- fluorophenyl ) biphenyl-4-amine)

biphenyl-4-amine (8.46 g , 50 mmol) and 1-bromo-4-fluorobenzene ( 9.63 g, 55 mmol) the later mixed in toluene _{480mL Pd 2 (dba) 3 (} 1.37 g, 1.5 mmol), PPh 3 ( 1.31 g, 5 mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 8.82 g (67%) of the product.

Sub 2-1-14 Synthesis Example (N1- (biphenyl-4- yl ) -N4, N4 - diphenylbenzene- 1,4- diamine)

Pd ₂ (dba) ₃ (1.37 g, 1.5 mmol), PPh (dibenzylideneacetone) and diisopropylethylamine were added to a solution of 4-bromo-N, N-diphenylaniline (17.83 g, 55 mmol) ₃ (1.31 g, 5 mmol) and NaO t- Bu (14.42 g, 150 mmol) were added, and the mixture was refluxed at 100 ° C for 24 hours. 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 14.64 g (71%) of the product.

Sub 2-1-1 ~ 2-1-14 were synthesized by the same method as above, and the product was confirmed by FD-MS as shown in the following table.

Sub 2-2 Compound Synthesis Example

Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol) and PPh ₃ (1.05 g, 4 mmol) were added to 385 mL of toluene after diphenylamine (6.77 g, 40 mmol) and 4,4'-dibromobiphenyl ) And NaO t- Bu (11.53 g, 150 mmol) were added, respectively, and the mixture was refluxed at 100 ° C for 24 hours. 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 11.69 g (73%) of the product.

Sub 2-2 to Sub 2-5

Sub 2-2 to Sub 2-5 and Sub 2-1-1 to 2-1-14 were synthesized in the same manner as described above, and the product was confirmed by FD-MS as follows.

Example of Final Product Synthesis

(1 eq.), Sub 2-2 (1.2 eq.), Pd ₂ (dba) ₃ (0.03 mmol), PPh ₃ (0.1 eq.), NaO t- Bu ) and toluene (10 mL / 1 mmol), 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 recrystallization.

Example of P2-6 synthesis

Sub-1-3-1 (10.03 g, 30 mmol), Sub2-2-6 (19.9 g, 36 mmol), Pd ₂ (dba) ₃ (0.83 g, 0.9 mmol), PPh ₃ (0.8 g, 3 mmol), NaO t- Bu (8.65 g, 90 mmol) and 300 mL of toluene. 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 16.44 g (68%) of the product.

After completion of the synthesis of the final product by the above-mentioned experimental method, the product was confirmed by FD-MS as follows.

In the meantime, although each of the substituents of the compounds represented by the formula (1) is broadly related, examples of synthesis of representative compounds have been exemplarily described, but the compounds represented by the formula (1), which are not exemplarily shown in the synthesis examples, Can be configured.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in the production of an organic electronic device including the organic light emitting device into the above structure, Materials can be prepared.

The compounds according to the present invention can be used in various applications in organic electroluminescent devices depending on the kind and nature of substituent groups.

Since the compounds of the present invention are controllable by the core and the substituent, they can act as various layers other than phosphorescent or fluorescent light emitting host hosts.

The organic electroluminescent device of the present invention can be manufactured by a conventional method and material for producing an organic electroluminescent device, except that the above-described compounds are used to form one or more organic substance layers.

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 light-emission assisting layer, an electron injecting layer, an electron transporting layer, and a hole injecting layer.

Meanwhile, the compound of the present invention can be used in a soluble process. That is, the organic compound layer of the organic electronic device described later can be formed by a soluble process of the compound. That is, when the compound is used as an organic material layer, the organic material layer may be formed by a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Lt; RTI ID = 0.0 > a < / RTI > fewer layers.

Organic electric devices in which the compounds of the present invention can be used include, for example, organic electroluminescent devices (OLED), organic solar cells, organic photoconductor (OPC) drums, organic transistors (organic TFT)

The organic electroluminescent device (OLED) will be described as one example of organic electroluminescent devices to which the compounds of the present invention can be applied, but the present invention is not limited thereto and the above-described compounds may be applied to various organic electroluminescent devices.

According to another embodiment of the present invention, there is provided 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 at least one of the organic material layers comprises the compound of the present invention to provide.

1 to 6 show examples of organic electroluminescent devices to which the compounds of the present invention can be applied.

The organic electroluminescent device according to another embodiment of the present invention can be manufactured by the same method as the organic electroluminescent device except that at least one layer of the organic compound layer including the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, Can be made with a structure known in the art using conventional manufacturing methods and materials in the art.

The structure of an organic electroluminescent device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited to these structures. Reference numeral 101 denotes a substrate, 102 denotes an anode, 103 denotes a hole injection layer (HIL), 104 denotes a hole transport layer (HTL), 105 denotes a light emitting layer (EML), 106 denotes an electron injection layer (EIL) ETL), and 108 denotes a cathode.

The organic electroluminescent device has a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for blocking the movement of electrons, a luminescent auxiliary layer for assisting or assisting luminescence and a protective layer It may be located. In the case of the protective layer, it may be formed to protect the organic layer at the uppermost layer or to protect the cathode.

At this time, the compound of the present invention may be included in at least one of organic compound layers including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

Specifically, the compound of the present invention may be used as a substitute for one or more of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, May be used. Of course, it can be used for more than two layers, not only one layer of the organic material layer.

In particular, it can be used as a hole injecting material, a hole transporting material, an electron injecting material, an electron transporting material, a light emitting material and a passivation (keping) material according to the compound of the present invention, It can be used as a dopant, and can be used as a hole injecting and hole transporting layer.

For example, the organic electroluminescent device according to another embodiment of the present invention may be formed by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, Oxide or an alloy thereof to form an anode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer on the anode, depositing a material usable as a cathode thereon .

In addition to such a method, the organic material may be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, but is not limited thereto and may have a single layer structure.

In addition, the organic material layer may be formed by using a variety of polymer materials, not by vapor deposition, but by a solution process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, It can be manufactured in a small number of layers.

The organic electroluminescent device according to another embodiment of the present invention may be used in a soluble process such as a spin coating process or an ink jet process.

The substrate may be a silicon wafer, a quartz or glass plate, a metal plate, a plastic film, or a sheet.

An anode is placed on the substrate. Such an anode injects holes into the hole injection layer located thereon. The anode material may be a material having a large work function so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

A hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are that the hole injection efficiency from the anode is high and the injected holes must be efficiently transported. For this purpose, the ionization potential is small, the transparency to visible light is high, and the stability against holes is excellent.

As the hole injecting material, a hole can be injected from the anode at a low voltage. The highest occupied molecular orbital (HOMO) of the hole injecting material may be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

A hole transport layer is disposed on the hole injection layer. The hole transport layer transports holes from the hole injection layer to an organic light emitting layer disposed thereon, and has high hole mobility, stability to holes, and electrons. In addition to these general requirements, heat resistance to a device is required when it is applied for vehicle display, and it may be a material having a glass transition temperature (Tg) of 70 DEG C or more.

Materials satisfying such conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium oxide Compounds, silicone-based arylamine compounds, and the like.

An organic light emitting layer is disposed on the hole transporting layer. The organic light emitting layer is a layer in which holes and electrons injected from the anode and the cathode respectively recombine to emit light, and the organic light emitting layer is made of a material having high quantum efficiency. The light emitting material may be a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and may be a material having good quantum efficiency for fluorescence or phosphorescence.

Materials or compounds that satisfy these conditions include Alq3 in the case of green, Balq (8-hydroxyquinoline beryllium salt) in the case of blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) biphenyl series, Spiro material, Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenolithium salt ), Bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complexes, imidazoles, thiazole and oxazole metal complexes, and perylene and BczVBi (3,3 ' (1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine). In the case of red, the green luminescent material was doped with DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl- -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile).

Polymers such as a polyphenylene vinylene (PPV) -based polymer and polyfluorene may be used for the organic light emitting layer when the light emitting layer is formed using processes such as inkjet printing, roll coating and spin coating .

An electron transporting layer is disposed on the organic light emitting layer. Such an electron transporting layer requires a material capable of efficiently injecting electrons with a high electron injection efficiency from a cathode disposed thereon. For this purpose, it is required to be made of a material having high electron affinity, high electron transfer rate and excellent stability against electrons.

Specific examples of the electron transporting material satisfying such conditions include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

An electron injection layer is deposited on the electron transport layer. The electron injection layer may be a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI or Tf-6P, boron compounds, and the like. At this time, the electron injection layer may be formed in a thickness range of 100 ANGSTROM to 300 ANGSTROM.

On the electron injection layer, a cathode is positioned. These cathodes serve to inject electrons. The material used for the cathode may be the material used for the anode and may be a metal having a low work function for efficient electron injection. Particularly suitable metals such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or their alloys may be used. Also, an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum, etc., having a thickness of 100 μm or less may be used.

As described above, the compound of the present invention can be used as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are suitable for the fluorescence of all colors such as red, green, It can be used as a host or dopant material of various colors.

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.

Meanwhile, the present invention includes a display device including the above-described organic electronic device and a terminal including a control unit for driving the display device. This terminal means a current or future wired or wireless communication terminal. The terminal according to the present invention may be a mobile communication terminal such as a mobile phone and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Evaluation of manufacturing of organic electric device

Comparative experiment Example 1

Organic electroluminescent devices were fabricated according to a conventional method by using various compounds obtained through synthesis as a luminescent host material or a hole transport layer of a luminescent layer. First, a 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the organic substrate as a hole injection layer to form a 10 nm thick film. Subsequently, the inventive compounds (Formula 1 to Formula 5) and Comparative Example were vacuum-deposited to a thickness of 20 nm using a hole transport layer. Vacuum deposition was carried out for comparative experiments. Thereafter, BD-052X (Idemitsu) was used as a luminescent dopant and 9,10-di- (naphthalene-2-anthracene) = AND] was used as a host material. The doping concentration was fixed at 4% Respectively. Subsequently, tris (8-quinolinol) aluminum was deposited to a thickness of 40 nm as an electron injecting layer. Thereafter, LiF as a halogenated alkyl metal was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and the Al / LiF was used as a cathode. Thus, an organic electroluminescent device was manufactured.

For the purpose of comparison of the compounds of the present invention, in order to confirm the effect of substituting the substituent of the carbazole with the compound represented by the following formula (hereinafter abbreviated as NPB) instead of the compound of the present invention, 3) was used as a hole transporting layer material to fabricate an organic electroluminescent device having the same structure as that of the test example.

For the purpose of comparison of the compounds of the present invention, in order to confirm the effect of substituting the substituent of the carbazole with the compound represented by the following formula (hereinafter abbreviated as NPB) instead of the compound of the present invention, 3) was used as a hole transporting layer material to fabricate an organic electroluminescent device having the same structure as in the test example

Comparative Example Compound (2) and Comparative Example Compound (3) in which a diarylamine group is connected at the 3-position of NPB and Carbazole of Comparative Example Compound (1) are shown in Table 6 as the inventive compounds P2-1 to P5-84 (2) and Comparative Example (3) in which carbazole was substituted with a diarylamine group at the 3-position of the carbazole, and Comparative Example (3) And Example 6 and Example 7. As a result, it was confirmed that the driving voltage and efficiency are improved as in the case of NPB.

Accordingly, it is considered that the driving voltage is lowered and thus the OLED has high efficiency and long life. In recent years,

It is expected to solve the problem of the number of problems due to the high driving voltage which is a problem in the device.

Comparative Experimental Example 2

An organic electroluminescent device was fabricated by a conventional method using a compound obtained through synthesis as a luminescent host material in a light emitting layer. First, a film of copper phthalocyanine (hereinafter referred to as CuPc) was vacuum deposited on the ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 10 nm. Subsequently, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vapor-deposited as a hole transport compound on the film to a thickness of 30 nm to form a hole transport layer . (2-phenylpyridine) iridium (hereinafter referred to as " Ir (ppy) ₃ ") as a phosphorescent Ir metal complex dopant was formed by depositing the above-described compound as a phosphorescent host material to form a hole transport layer, Flask). At this time, the concentration of Ir (ppy) _{3 in} the light emitting layer was 5 wt%. (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, and electron injection Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm. Then, an organic electroluminescence device was prepared by depositing LiF, which is an alkali metal halide, to a thickness of 0.2 nm, followed by depositing Al to a thickness of 150 nm and using this Al / LiF as a cathode.

For comparison of the compound of the present invention, in order to confirm the substituent effect of the compound of Comparative Example (4) (hereinafter abbreviated as CBP) represented by the following formula instead of the compound of the present invention and N of carbazole, ), (6), (7), and (8) were used as a light emitting host material to fabricate an organic electroluminescent device having the same structure as in the test example

Table 7 shows the comparison of the luminous efficiency and color purity with Comparative Example (4) using the present invention product as a phosphorescent host, and also to compare the difference in luminous efficiency depending on the position when a substituent is connected to the carbazole. The results of Table 7 show that the luminous efficiency of the present invention is higher than that of Comparative Example (4), and the diarylamine group, which is a substituent of the carbazole, Respectively.

Therefore, as can be seen from the results of Tables 6 and 7, the organic electroluminescent device using the material for the organic electroluminescence device having the diarylamine group connected to the position 2 of carbazole, High color purity, high efficiency and long life.

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.

Claims (10)

An organic electronic device comprising a compound represented by any one of the following formulas (3) and (4):

In the above formulas (3) and (4)
1) Ar ₁ is phenyl; Biphenyl; A 1-naphthyl group; A 2-naphthyl group; Pyridines substituted with at least one substituent selected from the group consisting of C ₆ to C ₆₀ aryl groups and C ₅ to C ₂₀ heterocyclic groups; A pyrimidine substituted with at least one substituent selected from the group consisting of an aryl group of C ₆ to C _{60 and} a heterocyclic group of C ₅ to C ₂₀ ; An aryl group having ₆ to ₆₀ carbon atoms, a heterocyclic group having ₅ to ₂₀ carbon atoms, or a substituted or unsubstituted triazine group;
₂₎ Ar 2 to Ar ₄ is a nitro group, C ₁ ~ C alkoxy group ₂₀ alkyl, C ₁ ~ C ₂₀ of, C ₁ ~ C _20, the same or different, hydrogen, deuterium, a halogen, an amino group, a nitrile group, and each of alkyl amine group, C ₁ ~ alkyl group of C ₂₀ 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 of a cycloalkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, an arylalkenyl group of C ₈ ~ C _20, a silane group, a boron group, a germanium group, a C ₅ ~ C ₂₀ of a C ₆ ~ C ₆₀ substituted or unsubstituted with one or more substituents selected from the group consisting of a hetero ring with an aryl group; A halogen atom, a halogen atom, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl Membered heterocyclic group, a nitrile group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, substituted with one or more substituents from the group or unsubstituted, and O, and optionally substituted with at least one of S or unsubstituted C ₅ ~ C ₆₀ heteroaryl group; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group substituted or unsubstituted C ₆ ~ C ₃₀ aryloxy group as; A halogen group, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ of the cycloalkyl group, C ₂ ~ C heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ C of the arylamine group with one or more substituents selected from the ₆₀ heteroaryl group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ of _30; C alkyl group of ₁ ~ C _20, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ aryl group of C ₂₀ aryl group, a C ₂ ~ C ₂₀ substituted with deuterium, C ₈ of alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ And Ar ₃ and Ar ₄ may combine with adjacent groups to form a saturated or unsaturated aliphatic ring or a heterocyclic ring. delete The organic electroluminescent device according to claim 1, wherein the compound represented by any one of the formulas (3) and (4) is selected from the following compounds:

Wherein the organic electroluminescent device comprises a first electrode, at least one organic material layer containing any one of the compounds described in any one of claims 1 to 3, and a second electrode sequentially stacked. The organic electroluminescent device according to claim 4, wherein the organic compound layer is formed by a soluble process. The organic electroluminescent device according to claim 4, wherein the organic material layer is used as a light emitting layer, a hole injecting layer, or a hole transporting layer. The electronic device according to claim 6, wherein the organic electroluminescent device is one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), and an organic transistor (organic TFT). A compound represented by any one of the following formulas (3) and (4):

In the above formulas (3) and (4)
1) Ar ₁ is phenyl; Biphenyl; A 1-naphthyl group; A 2-naphthyl group; Pyridines substituted with at least one substituent selected from the group consisting of C ₆ to C ₆₀ aryl groups and C ₅ to C ₂₀ heterocyclic groups; A pyrimidine substituted with at least one substituent selected from the group consisting of an aryl group of C ₆ to C _{60 and} a heterocyclic group of C ₅ to C ₂₀ ; An aryl group having ₆ to ₆₀ carbon atoms, a heterocyclic group having ₅ to ₂₀ carbon atoms, or a substituted or unsubstituted triazine group;
₂₎ Ar 2 to Ar ₄ is a nitro group, C ₁ ~ C alkoxy group ₂₀ alkyl, C ₁ ~ C ₂₀ of, C ₁ ~ C _20, the same or different, hydrogen, deuterium, a halogen, an amino group, a nitrile group, and each of alkyl amine group, C ₁ ~ alkyl group of C ₂₀ 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 of a cycloalkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, an arylalkenyl group of C ₈ ~ C _20, a silane group, a boron group, a germanium group, a C ₅ ~ C ₂₀ of a C ₆ ~ C ₆₀ substituted or unsubstituted with one or more substituents selected from the group consisting of a hetero ring with an aryl group; A halogen atom, a halogen atom, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₈ to C ₂₀ arylamine group, a C ₆ to C ₆₀ aryl Membered heterocyclic group, a nitrile group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, a C ₆ to C ₂₀ aryl group substituted with deuterium, a C ₈ to C ₂₀ arylalkyl group, a C ₈ to C ₂₀ arylalkenyl group, a C ₅ to C ₂₀ heterocyclic group, substituted with one or more substituents from the group or unsubstituted, and O, and optionally substituted with at least one of S or unsubstituted C ₅ ~ C ₆₀ heteroaryl group; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group A substituted or unsubstituted C ₁ to C ₃₀ alkoxy group; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ cycloalkyl group, At least one substituent selected from the group consisting of a C ₂ to C ₃₀ heterocycloalkyl group, a C ₆ to C ₆₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, and a C ₃ to C ₆₀ heteroaryl group substituted or unsubstituted C ₆ ~ C ₃₀ aryloxy group as; A halogen group, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₃₀ of the cycloalkyl group, C ₂ ~ C heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₃ ~ C of the arylamine group with one or more substituents selected from the ₆₀ heteroaryl group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ of _30; C alkyl group of ₁ ~ C _20, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ aryl group of C ₂₀ aryl group, a C ₂ ~ C ₂₀ substituted with deuterium, C ₈ of alkyl ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₅ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group unsubstituted or substituted with a substituent selected from the group consisting of C ₁ ~ C ₅₀ And Ar ₃ and Ar ₄ may combine with adjacent groups to form a saturated or unsaturated aliphatic ring or a heterocyclic ring. delete 9. The compound according to claim 8, wherein the compound represented by any one of the formulas (3) and (4) is selected from the following compounds:

Images