KR20180137203A - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present invention relates to a novel compound and to an organic electroluminescent device including the same, wherein the novel compound according to one embodiment of the present invention is applied to organic light emitting devices to ensure high efficiency, long life, low driving voltage and driving stability of the organic light emitting devices.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound, and an organic light emitting device including the same. BACKGROUND OF THE INVENTION [0002]

The present invention relates to a novel compound and an organic light emitting device comprising the same.

A material used as an organic material layer in an organic light emitting diode can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending largely on functions. The light emitting material may be classified into a polymer and a low molecular weight depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from an electron triplet excited state according to a light emitting mechanism, The light emitting material can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host 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 of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant and the host.

Various compounds have been known as materials for use in such organic light emitting devices. However, in the case of organic light emitting devices using known materials, development of new materials is continuously required due to high driving voltage, low efficiency, and short lifetime. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a material having excellent characteristics.

Korean Patent Publication No. 10-2015-0086721

The present invention provides a novel organic compound and an organic light emitting device containing the same.

However, the problems to be solved by the present invention are not limited to the problems described above, and other problems not described can be clearly understood by those skilled in the art from the following description.

A first aspect of the invention provides a compound represented by formula 1:

[Chemical Formula 1]

In Formula 1,

A, B, C, D and E are each independently hydrogen or represented by the following formula (1-1), and at least two of A, B, C, D and E are represented by the following formula (1-1). Provided that when A is represented by the following formula 1-1, C is hydrogen.

[Formula 1-1]

The second aspect of the present invention provides an organic light emitting device comprising an organic compound layer containing a compound according to the present invention between a first electrode and a second electrode.

The compound according to one embodiment of the present invention has a structure in which biphenyl and biphenylamine are bonded to each other, thereby achieving thin film stability and high efficiency of an organic light emitting device.

The compound according to one embodiment of the present invention can control the HOMO level according to the selection of bonding position of biphenyl and biphenylamine, and two biphenylamines can be bonded to increase the hole transporting property.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.

Hereinafter, embodiments and examples of the present invention will be described in detail with reference to the accompanying drawings, which will be readily apparent to those skilled in the art to which the present invention pertains.

It should be understood, however, that the present invention may be embodied in many different forms and is not limited to the embodiments and examples described herein. In order to clearly illustrate the present invention, parts not related to the description are omitted, and similar parts are denoted by like reference characters throughout the specification.

Throughout this specification, when a member is "on " another member, it includes not only when the member is in contact with the other member, but also when there is another member between the two members.

Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise. The terms "about "," substantially ", etc. used to the extent that they are used throughout the specification are intended to be taken to mean the approximation of the manufacturing and material tolerances inherent in the stated sense, Accurate or absolute numbers are used to help prevent unauthorized exploitation by unauthorized intruders of the referenced disclosure. The word " step (or step) "or" step "used to the extent that it is used throughout the specification does not mean" step for.

Throughout this specification, the term "combination thereof" included in the expression of the machine form means one or more combinations or combinations selected from the group consisting of the constituents described in the expression of the machine form, And the like.

Throughout this specification, the description of "A and / or B" means "A or B, or A and B".

Throughout this specification, the term "aryl" refers to a C _6-30 aromatic hydrocarbon ring group, such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, Means an aromatic ring such as phenyl, naphthyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, Examples of the C _5-30 aromatic ring containing a hetero element include pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Benzothiophenyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine rings, pyrazine rings, pyrimidine rings , Pyridazine ring, triazine ring, indole ring, quinoline ring , Acridine rings, pyrrolidine rings, dioxane rings, piperidine rings, morpholine rings, piperazine rings, carbazole rings, furan rings, thiophene rings, oxazole rings, oxadiazole rings, May include a heterocyclic group formed from a heterocyclic ring, a thiazole ring, a thiadiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring or a dibenzofuran ring .

"Optionally substituted" term throughout the present specification is a deuterium, a halogen, an amino group, a nitrile group, a nitro group or a C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ of the alkoxy group, Means a group selected from the group consisting of a C ₃ to C ₂₀ cycloalkyl group, a C ₃ to C ₂₀ heterocycloalkyl group, a C ₆ to C ₃₀ aryl group, and a C ₃ to C ₃₀ heteroaryl group can do. In addition, throughout the present specification, the same symbols may have the same meanings unless otherwise specified.

The symbol * denotes the joint position.

A first aspect of the invention provides a compound represented by formula 1:

[Chemical Formula 1]

In Formula 1,

A, B, C, D and E are each independently hydrogen or represented by the following formula (1-1), and at least two of A, B, C, D and E are represented by the following formula (1-1). Provided that when A is represented by the following formula 1-1, C is hydrogen.

[Formula 1-1]

In one embodiment of the present invention, the formula 1-1 may be represented by any one of the following formulas A-1 to A-6.

The compound is a combination of biphenyl and two biphenylamines, which can achieve the thin film stability and high efficiency of the organic light emitting device.

The compound according to one embodiment of the present invention can vary the bonding position of biphenylamine and biphenyl and can adjust the level of HOMO according to the positional selection, thereby achieving high efficiency of the organic light emitting device. In addition, hole transport characteristics including two biphenylamines can be increased, thereby achieving thin film stability and high efficiency of an organic light emitting device.

In one embodiment of the present invention, A is represented by Formula 1-1, and either of D and E may be represented by Formula 1-1.

In one embodiment of the present invention, B is represented by Formula 1-1, and any one of C, D and E may be represented by Formula 1-1.

Further, in one embodiment of the present invention, the compound may be represented by the following formulas (2) to (5).

[Chemical Formula 2] < EMI ID =

[Chemical Formula 4]

Compounds having a bonding structure of the above formulas (2) to (5), as compared with the structure represented by the formula (1-1), have a large steric hindrance So that a wide band gap can be obtained. Accordingly, it is possible to have a deep HOMO energy level, a high LUMO energy level and a high optical energy value. This has the effect of moving electrons and blocking the excitons in the light emitting layer, thereby increasing the light emitting property of the device.

As described above, in Formulas 2 to 5, A, B, C, D, and E may be represented by the following Formula 1-1, 6 < / RTI >

[Formula 1-1]

In the compound represented by Formula 2, A and D, that is, Formula 1-1, may be further specified as shown in Tables 1 and 2 below, but the present invention is not limited thereto.

In addition, in the compound represented by Formula 3, B, C, that is, Formula 1-1 may be further specified as shown in Tables 3 and 4 below, but the present invention is not limited thereto.

In the compound represented by Formula 4, B, D, that is, Formula 1-1 may be further specified as shown in Tables 5 and 6 below, but the present invention is not limited thereto.

In the compounds represented by the above formula (5), B, E, that is, the compound represented by the formula (1-1) may be further specified as shown in the following Tables 7 and 8, but the present invention is not limited thereto.

In one embodiment of the present invention, the compounds represented by Chemical Formulas 1 to 5 may be any one of the compounds shown below, but not limited thereto. In this case, it is easier to control the HOMO and LUMO energy levels, and the luminescence characteristics can be further increased when applied to a device. The numbers indicated in the following compounds are the numbers of the compounds described in Tables 1 to 6 above.

The second aspect of the present invention provides an organic light emitting device comprising the compound represented by any one of Chemical Formulas 1 to 5. The organic light emitting device may include at least one organic compound layer containing a compound according to the present invention between the first electrode and the second electrode.

In one embodiment of the present invention, the organic material layer may be a hole injection layer, a hole transport layer, and a light emission assisting layer, but may not be limited thereto. The compounds of the present invention may be used alone or in combination with known compounds when forming an organic layer.

In one embodiment of the present invention, the organic light emitting device may include, but not limited to, an organic material layer containing a hole transporting material and an organic material layer containing a compound represented by the general formula (1). According to one embodiment of the present invention, as described above, the compound of Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 5.

The organic light emitting device includes an organic layer such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode One or more layers may be included.

For example, the organic light emitting device can be fabricated as shown in FIG. The organic light emitting device includes an anode (hole injection electrode 1000), a hole injection layer 200, a hole transport layer 300, a light emitting layer 400, an electron transport layer 500, an electron injection layer 600, Implantation electrode 2000) may be stacked in this order.

1, the substrate 100 may be a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. have.

The hole injection electrode 1000 is used as an anode for hole injection of the organic light emitting element. A material having a low work function may be used to inject holes and may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene.

A hole injecting layer material may be deposited on the anode electrode by a method such as vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) method. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal properties of the desired hole injection layer, and the like. Generally, Temperature, a degree of vacuum of 10 ^{- 8} to 10 ^{- 3} torr, a deposition rate of 0.01 to 100 Å / sec, and a layer thickness range of 10 Å to 5 탆.

Next, a hole transporting layer material may be deposited on the hole injection layer 200 by a method such as vacuum deposition, spin coating, casting, or LB method to form the hole transporting layer 300. When the hole transporting layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer.

The hole transport layer 300 may be made of the compound according to the present invention. As described above, the compound according to the present invention may be used alone or a known compound may be used together. In addition, according to one embodiment of the present invention, the hole transport layer 300 may have one or more layers, and may include a hole transport layer formed only of a known material. In addition, according to an embodiment of the present invention, a light emitting auxiliary layer may be formed on the hole transport layer 300. In the present invention, the light-emission-assisting layer means a layer formed between the hole transporting layer and the light emitting layer, and may be referred to as a second hole transporting layer or a third hole transporting layer depending on the number of the hole transporting layers.

The light emitting layer material may be deposited on the hole transport layer 300 or the light emitting auxiliary layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. When the light emitting layer is formed by the vacuum vapor deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer. The light emitting layer material may be a known compound as a host or a dopant.

When the phosphorescent dopant is used together with the phosphorescent dopant, a hole blocking material (HBL) may be further deposited by vacuum evaporation or spin coating to prevent triplet excitons or holes from diffusing into the electron transport layer. The hole blocking material that can be used at this time is not particularly limited, but any known hole blocking material may be used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open Publication No. 11-329734 (A1) can be exemplified. Typically, Balq (bis Phenanthrolines based compounds such as UDC company BCP (bassocouroin), and the like can be used.

An electron transport layer 500 is formed on the light emitting layer 400 formed as described above. The electron transport layer may be formed by vacuum deposition, spin coating, casting, or the like. The deposition conditions of the electron transporting layer depend on the compound used, but it is generally preferable to select the conditions within the same range as the formation of the hole injection layer.

Then, an electron injection layer material may be deposited on the electron transport layer 500 to form an electron injection layer 600. The electron injection layer may be formed by vacuum deposition, spin coating, casting, And the like.

The hole injecting layer 200, the hole transporting layer 300, the light emitting layer 400 and the electron transporting layer 500 of the organic light emitting diode can be formed using the compound according to the present invention or the following materials. The compound and a known substance can be used together.

A cathode 2000 for electron injection is formed on the electron injection layer 600 by a vacuum evaporation method or a sputtering method. As the cathode, various metals may be used. Specific examples thereof include aluminum, gold, and silver.

The organic light emitting device of the present invention can have an organic light emitting device having various structures as well as an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode structure, Layer or an intermediate layer of two layers may be further formed.

As described above, the thickness of each organic material layer formed according to the present invention can be controlled according to the required degree, specifically 10 to 1,000 nm, and more specifically, 20 to 150 nm.

In addition, since the organic material layer containing the compound represented by the formula (1) can control the thickness of the organic material layer in the molecular unit, the present invention has advantages of uniform surface and excellent shape stability.

The organic light emitting compound according to the present invention may be applied to the first aspect of the present invention, but the present invention is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited by these Examples.

[Example]

The following reactants were used for the synthesis of the desired compounds.

Compound synthesis

Synthesis of Compound 16

Reaction product-2 (15.0 g, reactant-6 (12.0 g), (PPh ₃ ) ₄ Pd 1.1 g and K ₂ CO 38.3 g were dissolved in 350 ml of dioxane, and the mixture was refluxed and stirred.

 After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 14 g (yield 74%) of Compound 16. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 17

Compound 17 was synthesized (yield 68%) in the same manner as compound 16, using reactant-8 instead of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of compound 18

Compound 18 was synthesized (yield 71%) in the same manner as compound 16 by using Reaction product-7 instead of Reaction product-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 22

Compound 22 was synthesized (yield 69%) in the same manner as compound 16 by using Reaction-1 instead of Reaction-2. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 23

Compound 23 was synthesized (yield 65%) in the same manner as compound 16 by using reactant-1 instead of reactant-2 and reactant-8 instead of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 24

Compound 24 was synthesized (yield 76%) in the same manner as compound 16 by using Reactant-1 instead of Reactant-2 and Reactant-7 instead of Reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 29

Compound 29 was synthesized (yield 71%) in the same manner as compound 16 by using Reaction product-4 instead of Reaction product-2 and Reaction product-8 instead of Reaction product-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 30

Compound 30 was synthesized (yield 70%) in the same manner as compound 16 by using Reaction product-4 in place of Reaction product-2 and Reaction product-7 in place of Reaction product-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 33

Compound 33 was synthesized (yield 68%) in the same manner as compound 16 by using Reaction-3 instead of Reactant-2. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 34

Compound 34 was synthesized (yield 70%) in the same manner as compound 16 by using Reaction product-3 instead of Reaction product-2 and Reaction product-5 instead of Reaction product-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 35

Compound 35 was synthesized (yield 74%) in the same manner as compound 16 by using reactant-3 instead of reactant-2 and reactant-8 instead of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 36

Compound 36 was synthesized (yield 77%) in the same manner as compound 16 by using Reaction product-3 instead of Reaction product-2 and Reaction product-7 instead of Reaction product-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 54

Compound 54 was synthesized (yield 62%) in the same manner as compound 16 by using Reactant-18 instead of Reactant-2 and Reactant-15 instead of Reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 60

Compound 60 was synthesized (yield 63%) in the same manner as compound 16 by using reactant-17 instead of reactant-2 and reactant-15 instead of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 66

Compound 66 was synthesized (yield 60%) in the same manner as compound 16 by using Reaction product-20 instead of Reaction product-2 and Reaction product-15 instead of Reaction product-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 72

Compound 72 was synthesized (yield 68%) in the same manner as compound 16 by using reactant-19 in place of reactant-2 and reactant-15 in place of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 90

Compound 90 was synthesized (yield 65%) in the same manner as compound 16 by using reactant-18 instead of reactant-2 and reactant-7 instead of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 96

Compound 96 was synthesized (yield 60%) in the same manner as compound 16 by using reactant-17 in place of reactant-2 and reactant-7 in place of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 102

Compound 102 was synthesized (yield 64%) in the same manner as compound 16 by using reactant-20 instead of reactant-2 and reactant-7 instead of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 108

Compound 108 was synthesized (yield 60%) in the same manner as compound 16 by using reactant-19 in place of reactant-2 and reactant-7 in place of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 126

Compound 126 was synthesized (yield 65%) in the same manner as compound 16 by using reactant-18 instead of reactant-2 and reactant-23 instead of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 132

Compound 132 was synthesized (yield 60%) in the same manner as compound 16 by using reactant-17 in place of reactant-2 and reactant-23 in place of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 138

Compound 138 was synthesized (yield 64%) in the same manner as compound 16 by using reactant-20 instead of reactant-2 and reactant-23 instead of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Synthesis of Compound 144

Compound 144 was synthesized (yield 68%) in the same manner as compound 16 by using reactant-19 in place of reactant-2 and reactant-23 in place of reactant-6. m / z: 792 (100.0%), 793 (65.6%), 794 (21.0%

Organic Light Emitting Device Manufacturing

Example 1 (used as a hole transport layer)

A thin glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was cleaned, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator evaporator to form a hole injection layer HI01 of 600 angstroms, HATCN of 50 angstroms, and a hole transport layer of 600 angstroms. The light emitting layer was doped with BH01: BD01 of 3% to form 250 angstroms. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transport layer, LiF 10 Å and aluminum (Al) 1000 Å were formed, and the device was encapsulated in a glove box to produce an organic light emitting device.

Examples 2 to 24

The same procedure as in Example 1 was used except that the compound 16 was used instead of the compound 17, 18, 22, 23, 24, 29, 30, 33, 34, 35, 36, 54, 60, 66, 72, 90, 96, 108, 126, 132, 138, and 144, respectively.

Comparative Examples 1 to 5

Using the same method as in Example 1, instead of Compound 16, the following Ref.1 to Ref.5 were used to form an organic light emitting device.

 [Evaluation of performance of organic light emitting device]

A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). The performance of the organic light-emitting device of Examples and Comparative Examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under atmospheric pressure. The results are shown in Table 7 below.

Compound No. Op. V Cd / A CIEx CIEy LT97 Example 1 16 4.10 6.54 0.140 0.131 75 Example 2 17 4.09 6.90 0.139 0.138 70 Example 3 18 4.19 7.27 0.138 0.144 80 Example 4 22 4.14 6.49 0.140 0.123 65 Example 5 23 4.06 6.69 0.139 0.129 75 Example 6 24 4.09 6.90 0.140 0.125 70 Example 7 29 4.07 6.73 0.140 0.127 80 Example 8 30 4.08 7.07 0.139 0.134 80 Example 9 33 4.04 6.72 0.140 0.135 73 Example 10 34 4.14 7.09 0.139 0.141 75 Example 11 35 4.17 6.78 0.140 0.134 70 Example 12 36 3.98 6.99 0.140 0.126 70 Example 13 54 4.03 6.80 0.140 0.127 60 Example 14 60 4.03 6.90 0.140 0.131 80 Example 15 66 4.08 7.07 0.139 0.134 80 Example 16 72 4.04 6.72 0.140 0.135 75 Example 17 90 4.06 6.82 0.140 0.132 70 Example 18 96 4.06 6.69 0.139 0.129 75 Example 19 102 4.09 6.90 0.140 0.123 80 Example 20 108 4.07 7.04 0.140 0.123 70 Example 21 126 4.03 7.41 0.139 0.129 70 Example 22 132 4.07 6.73 0.140 0.127 75 Example 23 138 4.11 6.56 0.139 0.133 73 Example 24 144 3.99 6.86 0.140 0.129 70 Comparative Example 1 Ref.1 4.23 6.51 0.139 0.134 35 Comparative Example 2 Ref.2 4.21 6.17 0.140 0.134 40 Comparative Example 3 Ref.3 4.45      6.16 0.140 0.134 30 Comparative Example 4 Ref.4 4.23 6.49 0.139 0.139 45 Comparative Example 5 Ref.5 4.23 6.38 0.139 0.139 40

As shown in Table 7, in Examples 1 to 24 of the present invention, the compound according to the present invention was used as a hole transport layer to fabricate an organic light emitting device. Compared with Comparative Examples 1 to 5, the driving voltage was low , The efficiency and the lifetime were increased.

More specifically, the compounds of Examples 1 to 24 having two aryl amines in comparison with Comparative Examples 1 and 4 which do not have the structure of biphenyl and two aryl amines have increased hole transporting properties by arylamine A lower driving voltage and a higher efficiency. Compared with Comparative Example 2, which has biphenyl and two arylamine structures but has amines respectively of biphenyl and phenyl substituents, the compounds of Examples 1 to 24 having two biphenyl substituents have relatively high thermal properties It has excellent resonance structure and it has a possibility of stabilization of cation.

Comparative Example 3 in which two arylamines are bonded to biphenyl at all para positions, and two arylamines having a structure in which biphenyl and two arylamines are bonded, ) Compared to Comparative Example 5, the compounds of Examples 1 to 24 had low HOMO energy levels due to the specific bonding positions of the two aryl amines, and the holes were smoothly moved, resulting in lower driving voltage and high efficiency .

It will be understood by those of ordinary skill in the art that the foregoing description of the embodiments is for illustrative purposes and that those skilled in the art can easily modify the invention without departing from the spirit or essential characteristics thereof. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.

The scope of the present invention is defined by the appended claims rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be interpreted as being included in the scope of the present invention .

100: substrate
200: Hole injection layer
300: hole transport layer
400: light emitting layer
500: electron transport layer
600: electron injection layer
1000: anode
2000: cathode

Claims (9)

A compound represented by the following general formula (1)
[Chemical Formula 1]

In Formula 1,
A, B, C, D and E are each independently hydrogen or represented by the following formula (1-1), and at least two of A, B, C, D and E are represented by the following formula (1-1). Provided that when A is represented by the following formula 1-1, C is hydrogen.
[Formula 1-1]

The method according to claim 1,
The compound represented by Formula 1-1 is represented by any one of the following Formulas A-1 to A-6:

The method according to claim 1,
Wherein A is represented by Formula 1-1, and either of D and E is represented by Formula 1-1.
The method according to claim 1,
B is a group represented by the formula (1-1), and any one of C, D and E is represented by the formula (1-1).
The method according to claim 1,
The compound is a compound represented by the following Chemical Formulas 2 to 5:
[Chemical Formula 2] < EMI ID =

[Chemical Formula 4]

The method according to claim 1,
Wherein said compound is any one of the following compounds:

An organic light emitting device comprising an organic material layer containing a compound according to any one of claims 1 to 6 between a first electrode and a second electrode. 8. The method of claim 7,
Wherein the organic material layer is one or more layers of a hole injecting layer, a hole transporting layer, and a light emitting auxiliary layer. 9. The method of claim 8,
Wherein the organic material layer is a hole transporting layer.

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