KR20190013123A - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present invention relates to a novel bis-biphenylamine derivative compound. When the novel bis-biphenylamine derivative compound is used as a hole transport layer (HTL), hole transport layer (HT prime) or a hole injection layer (HIL), hole injection and transport properties can be increased, thereby providing high efficiency and a long-life effect of a device. The present invention provides a compound represented by chemical formula 1 and an organic electroluminescent device comprising an organic material layer containing the compound between a first electrode and a second electrode.

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 bis-biphenylamine derivative 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.

Japanese Patent Laid-Open No. 10-2015-530735

The present invention is to provide a novel bis-biphenylamine derivative compound, a method for producing the same, and an organic light emitting device including 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,

R ₁ to R ₄ are each independently a substituted or unsubstituted C ₆ to C ₅₀ aryl group or a substituted or unsubstituted C ₅ to C ₅₀ heteroaryl group.

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

The compound of the present invention is a bis-biphenylamine derivative having a bulky form and can bind to two types of biphenyl amines capable of increasing amorphousness to form a HOMO that facilitates hole injection and transport. In addition, various substituents can be bonded to amines connected to ortho to biphenyl interconnection sites, suppression of conjugation expansion, excellent thin film and interfacial alignment of molecules, and rapid roll-off through hole mobility It is possible to inhibit development. At the same time, by using two biphenyl amines, thermal stability, which is a main factor of the hole transport layer, can be ensured and a long-life device can be realized.

When the compound of the present invention is used as a hole transporting layer (HTL), a light emitting auxiliary layer (HT prime) or a hole injecting layer (HIL), hole injecting and transporting properties can be increased, thereby providing a high efficiency and long life effect of the device. The compound of the present invention can maintain a high triplet energy, exhibits high efficiency, and can form a high Tg at a relatively low molecular weight to prevent recrystallization of the thin film, thereby exhibiting thin film stability and long life time effect when the device is driven.

The compound of the present invention has such effects as high luminous efficiency and high color purity, and can contribute greatly to the OLED industry such as flexible display and illumination by applying it to an organic light emitting device, an organic photonic device for solar power generation, and the like.

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 ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazine Means an aromatic 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.

Throughout the specification, the term "alkyl" may be linear or branched, including saturated or unsaturated C ₁ -C ₆ alkyl, such as methyl, ethyl, propyl, butyl, pentyl, But is not limited to, all possible isomers.

The term " optionally substituted "or" substituted "as used throughout this application is intended to encompass a variety of substituents such as deuterium, halogen, amino, nitrile, nitro, silane, alkyl or C ₁ -C ₂₀ alkyl, alkenyl or C ₂ -C ₂₀ An alkoxy group or a C ₁ to C ₂₀ alkoxy group, a cycloalkyl group or a C ₃ to C ₂₀ cycloalkyl group, a heterocycloalkyl group or a C ₃ to C ₂₀ heterocycloalkyl group or a C ₅ to C ₃₀ aryl group or A C ₅ to C ₃₀ heteroaryl group, and the like.

In addition, throughout the present specification, the same symbols may have the same meanings unless otherwise specified.

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

[Chemical Formula 1]

In Formula 1,

R ₁ to R ₄ are each independently a substituted or unsubstituted C ₆ to C ₅₀ aryl group or a substituted or unsubstituted C ₅ to C ₅₀ heteroaryl group.

In one embodiment of the present invention, each of R ₁ to R ₄ may independently be any one of the following structures:

In the above structure, L ₁ is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group.

In one embodiment of the invention, L < ₁ > can be any of the following structures:

In the above structure, * is a bonding position.

In one embodiment of the present invention, at least two of R ₁ to R ₄ may be phenyl, for example, at least one of R ₁ and R ₂ is phenyl, and at least one of R ₃ and R ₄ May be phenyl.

In one embodiment of the present invention, R ₁ to R ₄ may each independently be carbazole, dibenzofuran or fluorene.

In one embodiment of the present invention, the compound represented by Formula 1 may be synthesized by the reaction shown in Reaction Schemes 1 and 2, but not limited thereto:

[Reaction Scheme 1]

[Reaction Scheme 2]

In the above Reaction Schemes 1 and 2,

R ₁ to R ₄ are as defined in Formula 1 above.

In one embodiment of the present invention, the compound represented by Formula 1 may include, but is not limited to, the following compounds:

According to embodiments of the present invention, the compound represented by Formula 1 may include the following compounds. These compounds may have a HOMO energy level suitable for a hole transporting layer and have excellent hole transportability. In addition, it has thermal stability and can realize long lifetime of the device.

The second aspect of the present invention provides an organic light emitting device comprising the compound represented by Formula 1. The organic light emitting device may include one or more organic layers including 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 at least one of a hole injection layer, a hole transporting layer, and a light-emitting auxiliary layer. For example, the organic material layer may be a hole transporting layer, but the present invention is not limited thereto. The compounds may be used alone or in combination with known organic luminescent compounds.

In the present invention, the light-emission-assisting layer is 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.

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).

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

For example, the organic light emitting device can be manufactured according to the structure 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, the structure and thermal properties of the desired hole injection layer, and the like. In general, the deposition temperature is 50-500 [ A vacuum of 10 < ^-8 > to 10 < ^-3 > torr, a deposition rate of 0.01 to 100 ANGSTROM / sec, and a layer thickness range of 10 ANGSTROM to 5 mu m.

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 may be one or more, for example, two layers of a first hole transport layer and a second hole transport layer (emission auxiliary layer). At least one of the first hole transporting layer and the second hole transporting layer may include the compound of Formula 1 according to the present invention.

Then, the light emitting layer material may be deposited on the hole transport layer 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 evaporation, spin coating, Casting method or 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 device can be formed using the compound according to the present invention or the following compounds, Known materials 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 in accordance with the present invention can be controlled depending on the required degree, specifically 5 to 1,000 nm, more specifically 5 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 ]

Manufacturing example  One

Bis (Biphenyl amine) diphenyl (BBA)  synthesis

Preparation of BBA for synthesis of target compound was synthesized through the above steps.

The synthesis method of the BBA is as follows.

12.0 g of substance A and 15 g of substance B were dissolved in 150 ml of 1,4-dioxane. To the round bottom flask, 30 ml of K ₂ CO ₃ (2M) and 1.5 g of Pd (PPh ₃ ) ₄ were added 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 to obtain 11 g (yield: 70.1%) of intermediate BBA.

BBA - pH  Synthesis of materials

The above BBA and bromo phenyl were synthesized to synthesize the following BBA-ph materials.

Synthesis of OP

For the synthesis of the target compound, the following structure was used for OP materials, some of them were synthesized and some were purchased and used.

Synthesis of OP3

To a round bottom flask Dibenzofuran-4-boronic acid 20.0g, 4-bromo-1-Iodo-benzene is dissolved in 26g, 1,4- dioxane _{200ml K 2 CO 3 (2M)} 40ml and Pd (PPh _{3) 4} 2.5g And the mixture was stirred under reflux. 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 purified to obtain 23 g (yield: 75.7%) of intermediate OP3 (4- (4-bromophenyl) dibenzo [b, d] furan).

m / z: 322.00 (100.0%), 324.00 (97.5%), 323.00 (19.5%), 325.00 (19.1%

Synthesis of OP9

To a round bottom flask was dissolved 20.0 g of 3-bromo-9-phenyl-9H-carbazole, 19.5 g of 4-bromo-1-iodo-benzene and 200 ml of 1,4-dioxane. 40 ml of K ₂ CO ₃ (2M) PPh ₃ ) _{4 (} 2.6 g) were added, and the mixture was stirred under reflux. 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 to obtain 21 g (yield: 77.8%) of intermediate OP9 (3- (4-bromophenyl) -9-phenyl-9H-carbazole).

m / z: 397.05 (100.0%), 399.04 (97.3%), 398.05 (26.1%), 400.05 (25.4%), 399.05 (3.3%

Synthesis of OP10

20.0 g of 9H-carbazole, 33.8 g of 4-bromo-1-iodo-benzene, 18 g of t-BuONa, 1.8 g of Pd ₂ (dba) ₃ and 2.0 ml of (t-Bu) ₃ P were dissolved in 200 ml of toluene Followed by reflux stirring. 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 to obtain 26 g (yield: 68.8%) of intermediate OP10 (9- (4-bromophenyl) -9H-carbazole).

m / z: 321.02 (100.0%), 323.01 (97.3%), 322.02 (19.6%), 324.02 (19.1%), 323.02

Synthetic example  1. Synthesis of Compound 1

20 g of BBA-ph, 8 g of OP1 (4-bromobiphenyl), 18 g of t-BuONa, 1.8 g of Pd ₂ (dba) ₃ and 2.0 ml of t-Bu ₃ P were dissolved in 200 ml of toluene, . 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 17.2 g of Compound 1 (yield: 73%).

m / z: 716.32 (100.0%), 717.32 (59.1%), 718.33 (17.0%), 719.33

Synthetic example  2. Synthesis of Compound 2

Compound 2 was synthesized by the same method as Compound 1 using OP2 (4-bromobiphenyl) instead of OP1 (yield 69%).

m / z: 716.32 (100.0%), 717.32 (59.1%), 718.33 (17.0%), 719.33

Synthetic example  3. Synthesis of Compound 3

To a round bottom flask were dissolved 20.0 g of BBA, 14 g of OP1, 14 g of t-BuONa, 1.4 g of Pd ₂ (dba) ₃ and 1.7 ml of (t-Bu) ₃ P in 200 ml of toluene and the mixture was stirred under reflux. 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 16.90 g (yield: 71%) of Compound 3.

m / z: 792.35 (100.0%), 793.35 (65.6%), 794.36 (21.0%), 795.36

Synthetic example  4. Synthesis of Compound 4

Compound 4 was synthesized in the same manner as Compound 3 using OP2 instead of OP1 (Yield: 76%).

m / z: 792.35 (100.0%), 793.35 (65.6%), 794.36 (21.0%), 795.36

Synthetic example  5. Synthesis of Compound 5

Compound 5 was synthesized in the same manner as Compound 1 using OP3 instead of OP1. (Yield 64%)

m / z: 806.33 (100.0%), 807.33 (65.7%), 808.34 (21.0%), 809.34 (4.6%

Synthetic example  6. Synthesis of Compound 6

Compound 6 was synthesized by the same method as Compound 1 using OP4 (2-bromo-9,9-diphenylfluorene) instead of OP1. (Yield: 68%)

m / z: 756.35 (100.0%), 757.35 (62.4%), 758.36 (19.0%), 759.36 (3.8%

Synthetic example  7. Synthesis of Compound 7

Compound 7 was synthesized by the same method as Compound 1 using OP5 (2-bromo-9,9-diphenylfluorene) instead of OP1. (Yield: 71%)

m / z: 880.38 (100.0%), 881.39 (73.0%), 882.39 (26.3%), 883.39 (6.4%

Synthetic example  8. Synthesis of Compound 8

Compound 8 was synthesized by the same method as Compound 1 using OP6 (2-bromo-9,9'-spiro [9H-fluorene]) instead of OP1. (70% yield)

m / z: 878.37 (100.0%), 879.37 (73.0%), 880.37 (26.4%), 881.38 (6.2%), 882.38

Synthetic example  9. Synthesis of Compound 9

Compound 9 was synthesized in the same manner as Compound 1 using OP7 (3-bromo-9-phenylcarbazole) instead of OP1. (Yield: 68%)

m / z: 805.35 (100.0%), 806.35 (65.4%), 807.35 (21.4%), 808.36 (4.4%

Synthetic example  10. Synthesis of Compound 10

Compound 10 was synthesized by the same method as Compound 1 using OP8 (2-Bromo-9-phenyl-9H-carbazole) instead of OP1. (Yield: 61%)

m / z: 805.35 (100.0%), 806.35 (65.4%), 807.35 (21.4%), 808.36 (4.4%

Synthetic example  11. Synthesis of Compound 11

Compound 11 was synthesized in the same manner as Compound 1 using OP9 instead of OP1. (Yield: 65%)

m / z: 881.38 (100.0%), 882.38 (71.9%), 883.38 (25.9%), 884.39 (5.9%), 882.37 (1.1%), 885.39

Synthetic example  12. Synthesis of Compound 12

Compound 12 was synthesized in the same manner as Compound 1 using OP10 instead of OP1. (Yield 66%)

m / z: 805.35 (100.0%), 806.35 (65.4%), 807.35 (21.4%), 808.36 (4.4%

Synthetic example  13. Synthesis of Compound 13

Compound 13 was synthesized by the same method as Compound 3 using OP11 instead of OP1. (Yield: 75%)

m / z: 740.32 (100.0%), 741.32 (61.3%), 742.33 (18.3%), 743.33 (3.6%

Synthetic example  14. Synthesis of Compound 14

Compound 14 was synthesized in the same manner as Compound 3 using OP12 instead of OP1. (Yield: 79%)

m / z: 740.32 (100.0%), 741.32 (61.3%), 742.33 (18.3%), 743.33 (3.6%

Example 1: Preparation of organic light emitting device

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 prepare a hole injection layer HI01 of 600 Å, HATCN of 50 Å, a hole transport layer of compound 1 600 Å, and a light emitting layer of BH01: BD01 doped with 3% to form 250 Å. Next, ET01: Liq (1: 1) 300 Å was formed as an electron transport layer, LiF 10 Å and aluminum (Al) 1000 Å were prepared, and the device was encapsulated in a glove box to prepare an organic light emitting device.

Examples 2 to 14: Preparation of organic light emitting device

An organic light emitting device having a hole transport layer formed by using the same method as Example 1, but using Compound (2) to (14) instead of Compound (1) was prepared.

Comparative Examples 1 to 7

Using the same method as in Example 1, instead of compound 1, the following Ref.1 to Ref.7 were respectively used to prepare an organic light emitting device.

Experimental Example  1: Performance evaluation 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 devices of the examples and comparative examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under the atmospheric pressure condition, and the results are shown in Table 1.

Op. V mA / cm2 Cd / A lm / W CIEx CIEy LT95 Example 1 3.60 10 6.48 5.84 0.139 0.120 110 Example 2 3.55 10 6.50 5.77 0.140 0.120 100 Example 3 3.52 10 6.72 6.01 0.140 0.120 115 Example 4 3.50 10 6.61 5.95 0.140 0.120 108 Example 5 3.65 10 6.99 6.02 0.140 0.120 125 Example 6 3.36 10 7.38 6.92 0.139 0.121 140 Example 7 3.42 10 7.15 6.59 0.140 0.121 134 Example 8 3.45 10 7.07 6.46 0.143 0.123 125 Example 9 3.22 10 7.23 7.07 0.141 0.123 142 Example 10 3.35 10 7.36 6.92 0.141 0.122 151 Example 11 3.32 10 7.55 7.16 0.142 0.121 169 Example 12 3.71 10 6.32 5.36 0.142 0.122 102 Example 13 3.64 10 6.42 5.55 0.141 0.123 105 Example 14 3.61 10 6.33 5.52 0.141 0.123 105 Comparative Example 1 3.80 10 6.24 5.17 0.140 0.125 95 Comparative Example 2 4.25 10 5.32 3.94 0.141 0.123 83 Comparative Example 3 3.94 10 5.72 4.57 0.140 0.125 75 Comparative Example 4 3.78 10 6.04 5.03 0.141 0.120 77 Comparative Example 5 3.96 10 6.10 4.85 0.139 0.120 78 Comparative Example 6 3.81 10 6.17 5.10 0.138 0.120 90 Comparative Example 7 3.85 10 6.03 4.93 0.140 0.120 83

As shown in Table 1, it can be seen that the embodiments of the present invention are superior in the efficiency and the life time as compared with Comparative Examples 1 to 7.

More specifically, when compared with Comparative Examples 1, 2 and 6, which have a quarter phenyl moiety but their bonding positions are different from those of the present invention, embodiments of the present invention inhibit conjugation expansion and exhibit fast hole mobility, And the efficiency and lifetime effect are greatly improved. Compared with Comparative Examples 3, 4, 5 and 7 having no quaternary phenyl moieties, Examples 1, 2, 3 and 4 of the present invention show that the driving voltage is low and the efficiency and lifetime are greatly improved. Particularly, when dibenzofuran is substituted as in Example 5 and when fluorene is substituted as in Examples 6, 7, and 8, or when carbazole is substituted as in Examples 9, 10, and 11, a simple resonance structure It is confirmed that the driving voltage is lower than that in the case of replacing the aryl having a substituent, and the efficiency and lifetime are improved.

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 formula (1):
[Chemical Formula 1]

In Formula 1,
R ₁ to R ₄ are each independently a substituted or unsubstituted C ₆ to C ₅₀ aryl group or a substituted or unsubstituted C ₅ to C ₅₀ heteroaryl group. The method according to claim 1,
Each of R ₁ to R ₄ is independently any one of the following structures:

L ₁ is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group. 3. The method of claim 2,
Wherein L < ₁ > is any one of the following structures:

The method according to claim 1,
Wherein at least two of R &_lt; ₁ > to R &_lt; ₄ &_gt; are phenyl. The method according to claim 1,
Wherein at least one of R ₁ and R ₂ is phenyl and at least one of R ₃ and R ₄ is phenyl. The method according to claim 1,
Wherein R ₁ to R ₄ are each independently carbazole, dibenzofuran or fluorene. The method according to claim 1,
Wherein the compound represented by Formula 1 comprises any one of the following compounds:

An organic light-emitting device comprising an organic material layer containing a compound of any one of claims 1 to 7 between a first electrode and a second electrode. 9. The method of claim 8,
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.

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