KR20190011090A - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present invention relates to a novel arylamine compound, which facilitates hole injection and hole transport, thereby exhibiting effects of low voltage and low power consumption. In addition, the novel arlyamine compound exhibits high efficiency by having high LUMO, which enables electronic blocking, due to a wide band gap and can increase thermal stability through Tg rise by increasing robustness in a molecule, thereby stabilizing the life of a device.

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 novel arylamine compounds and organic light emitting devices 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 seeks to provide a novel arylamine 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,

R ₁ to R ₄ are each independently a C ₁ to C ₃₀ alkyl group or a C _{6 to} C ₃₀ aryl group,

L ₁ and L ₂ are each independently a direct bond, a C ₆ -C ₃₀ arylene group which may be substituted or a C ₅ -C ₃₀ heteroarylene group which may be substituted,

B is a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

m and n are each independently an integer of 0 or 1;

A second aspect of the present invention provides an organic light emitting device comprising a compound according to the present invention.

The present invention relates to a novel arylamine compound, which facilitates hole injection and hole transport, thereby exhibiting low voltage and low power consumption. In addition, since it has a wide bandgap, it has a high LUMO that can cut off electrons and shows high efficiency. It can increase the intrinsic rigidity and increase the thermal stability by increasing the Tg, thereby stabilizing the lifetime of the device.

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.

* Denotes the joint position.

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 C ₁ to C ₃₀ alkyl group or a C _{6 to} C ₃₀ aryl group,

L ₁ and L ₂ are each independently a direct bond, a C ₆ -C ₃₀ arylene group which may be substituted, or a C ₅ -C ₃₀ heteroarylene group which may be substituted,

B is a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,

m and n are each independently an integer of 0 or 1;

In one embodiment of the present invention, R ₁ to R ₄ may each independently be methyl or phenyl.

In one embodiment of the present invention, R ₁ and R ₂ are the same as each other, and R ₃ and R ₄ may be the same as each other.

In one embodiment of the present invention, B may comprise the following structure:

For example, but not limited to, B may be expressed as:

In one embodiment of the present invention, L ₁ and L ₂ are each independently a direct bond or may include the following structure.

For example, L < _{1 >} and L < _{2 >} may be a direct bond or include any of the following formulas:

The compound represented by the above formula (1) wherein B is phenyl, wherein R ₁ to R ₄ is methyl or phenyl, R ₁ and R ₂ are the same and are identical to each other R ₃ and R _4, wherein L ₁ and to each other L ₂ may each independently be a direct bond, any one of the following formulas (11), (12), and (21)

According to one embodiment of the present invention, B, R ₁ , R ₂ , R ₃ , R _4, m, n, L ₁ and L ₂ in the definition of Formula 1 may be formulated as shown in Tables 1 to 6 And may not be limited thereto.

The compounds of the formula (1) wherein B is to a formula 4-1 or formula 4-2, wherein R ₁ to R ₄ is methyl or phenyl, R ₁ and R ₂ are the same, and wherein R ₃ and R ₄ together They are identical, and to the L ₁ and L ₂ is a bond, each independently, may comprise any one of the compounds of formula 11, formula 12, and formula 21 to formula 25 with each other:

According to one embodiment of the present invention, B, R ₁ , R ₂ , R ₃ , R _4, m, n, L ₁ and L ₂ in the definition of Formula 1 may be formulated as shown in Tables 7 to 18 below And may not be limited thereto.

R ₁ and R ₄ are methyl or phenyl, R ₁ and R ₂ are the same as each other, and R ₃ and R ₄ are the same as each other, They are identical, and to the L ₁ and L ₂ is a bond, each independently, may comprise any one of the compounds of formula 11, formula 12, and formula 21 to formula 25 with each other:

According to one embodiment of the present invention, B, R ₁ , R ₂ , R ₃ , R _4, m, n, L ₁ and L ₂ in the definition of Formula 1 may be formulated as shown in Tables 19 to 30 below And may not be limited thereto.

The compounds of the formula (1) wherein B is to a formula 6-1 or formula 6-2, wherein R ₁ to R ₄ is methyl or phenyl, R ₁ and R ₂ are the same, and wherein R ₃ and R ₄ together are the same to each other, wherein L ₁ and L ₂ include any one compound of each directly bonded independently to formula 11, formula 12, and formula 21) to (25:

According to one embodiment of the present invention, B, R ₁ , R ₂ , R ₃ , R _4, m, n, L ₁ and L ₂ in the definition of Formula 1 may be formulated as shown in Tables 31 to 42 below And may not be limited thereto.

For example, the compound represented by Formula 1 may include the following compounds.

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 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. For example, the hole injection layer may comprise a compound according to the present invention.

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). Any 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.

Thereafter, the light emitting layer material may be deposited on the hole transporting layer by vacuum evaporation, spin coating, casting, LB method, or the like to form the light emitting layer 400. 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

The RM-1 to RM-10 used for the synthesis of the objective compound are as follows:

RM Synthesis of -11

For the synthesis of the target compound, RM-11 was synthesized by the above reaction scheme.

15.0 g of 2,6-dibromo-4-chloroaniline and 13.5 g of phenylboronic acid (RM-1) were dissolved in 200 ml of 1,4-dioxane in a round bottom flask, and 60 ml of K ₂ CO ₃ (2M) PPh ₃ ) _{4 (} 3.64 g) was added thereto, followed by stirring under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. Then, 13.5 g of phenylboronic acid (RM-1) was dissolved in 200 ml of 1,4-dioxane, and 60 ml of K ₂ CO ₃ (2M) and 1.6 g of Pd (PPh ₃ ) ₄ were further added thereto and 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 8 g of intermediate RM-11 (yield 70%).

m / z: 321.15 (100.0%), 322.16 (26.2%), 323.16 (3.3%)

RM-12 to RM-17 were synthesized using RM-2 to RM-7 instead of RM-1 using the same method as RM-11.

Synthetic example  One: Compound 1  synthesis

In a round bottom flask, 4.2 g of RM-11, 10 g of RM-10, 5 g of t-BuONa, 1.3 g of Pd ₂ (dba) ₃ and 1.5 ml of (t-Bu) ₃ P were dissolved in 200 ml of toluene and 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 Compound 1 (7.01 g, yield 70%).

m / z: 953.40 (100.0%), 954.41 (80.6%), 955.41 (32.1%), 956.41 (8.3%), 957.42

Synthetic example  2: Compound 55  synthesis

Compound 55 was synthesized by the same method as Compound 1 using RM-8 instead of RM-10 (yield: 74%).

m / z: 705.34 (100.0%), 706.34 (58.8%), 707.35 (17.0%), 708.35

Synthetic example  3: Compound 56  synthesis

4.2 g of RM-11, 5 g of RM-8, 2.5 g of t-BuONa, 0.65 g of Pd ₂ (dba) ₃ and 1 ml of (t-Bu) ₃ P were dissolved in 100 ml of toluene and 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 5.01 g (yield: 74%) of IM-001.

Then, 5 g of IM-001, 6 g of RM-9, 3 g of t-BuONa, 0.6 g of Pd ₂ (dba) ₃ and 1.5 ml of (t-Bu) ₃ P were dissolved in 100 ml of toluene and 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 4.01 g (yield: 53%) of Compound 56.

m / z: 781.37 (100.0%), 782.37 (65.3%), 783.38 (21.1%), 784.38

Synthetic example  4: Compound 63  synthesis

Compound 63 was synthesized in the same manner as Compound 1 using RM-9 instead of RM-10 (yield: 64%).

m / z: 857.40 (100.0%), 858.41 (72.0%), 859.41 (25.5%), 860.41 (5.9%), 861.42

Synthetic example  5: Compound 163  synthesis

Compound 163 was synthesized in the same manner as Compound 1 using RM-8 instead of RM-10 and RM-13 instead of RM-11 (yield: 64%).

m / z: 795.35 (100.0%), 796.35 (65.3%), 797.36 (21.1%), 798.36

Synthetic example  6: Compound 271  synthesis

Compound 271 was synthesized by the same method as Compound 1 using RM-8 instead of RM-10 and RM-12 instead of RM-11 (yield 60%).

m / z: 795.35 (100.0%), 796.35 (65.3%), 797.36 (21.1%), 798.36

Synthetic example  7: Compound 379  synthesis

Compound 379 was synthesized by the same method as Compound 1 using RM-8 instead of RM-10 and RM-15 instead of RM-11 (Yield: 61%).

m / z: 811.33 (100.0%), 812.33 (66.2%), 813.33 (21.5%), 813.32 (4.5%), 814.34 (4.4%

Synthetic example  8: Compound 595  synthesis

Compound 595 was synthesized by the same method as Compound 1 using RM-8 instead of RM-10 and RM-17 instead of RM-11 (yield: 61%).

m / z: 870.40 (100.0%), 871.40 (72.0%), 872.40 (25.6%), 873.41 (5.9%), 874.41

Synthetic example  9: Compound 703  synthesis

Compound 703 was synthesized by the same method as Compound 1 using RM-8 instead of RM-10 and RM-16 instead of RM-11 (yield: 52%).

m / z: 870.40 (100.0%), 871.40 (72.0%), 872.40 (25.6%), 873.41 (5.9%), 874.41

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 washed 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 was formed as a hole injection layer HI01 600 Å, HATCN 50 Å, a hole transport layer 1 600 Å, and then doped with 3% BH01: BDO1 as the light emitting layer 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 film-formed and the device was encapsulated in a glove box, ).

Examples 2 to 9: Preparation of organic light emitting device

(Examples 2 to 9) in which a hole transporting layer was formed by using compounds 55, 56, 63, 163, 271, 379, 595, and 703 instead of Compound 1 using the same method as in Example 1 .

Comparative Example  1 to 9

Using the same method as in Example 1, instead of Compound 1, the following Ref.1 to Ref.9 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 device of 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 43. [

As can be seen from Table 43, the compounds of Examples 1 to 9 of the present invention were used as a hole transport layer, and it was confirmed that the efficiency and lifetime were increased as compared with Comparative Examples 1 to 8. [

More specifically, unlike Comparative Examples 1 to 5 and 7 in which only one fluorene is contained, the compound of the present invention containing two or more fluorenes has a low driving voltage, and increased efficiency and lifetime. Further, in the case of a device using a compound including terphenyl, dibenzofuran, dibenzothiophene and the like in addition to two fluorenes, the driving voltage was low, and the efficiency and lifetime increased. In particular, when compared with Comparative Example 9 which does not contain terphenyl, it was confirmed that the compound of the present invention has excellent thermal properties.

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 (15)

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

In Formula 1,
R ₁ to R ₄ are each independently a C ₁ to C ₃₀ alkyl group or a C _{6 to} C ₃₀ aryl group,
L ₁ and L ₂ are each independently a direct bond, a C ₆ -C ₃₀ arylene group which may be substituted, or a C ₅ -C ₃₀ heteroarylene group which may be substituted,
B is a C ₆ -C ₃₀ aryl group which may be substituted or a C ₅ -C ₃₀ heteroaryl group which may be substituted,
m and n are each independently an integer of 0 or 1; The method according to claim 1,
Wherein R ₁ to R ₄ are each independently methyl or phenyl. 3. The method according to claim 1 or 2,
Wherein R ₁ and R ₂ are the same as each other, and R ₃ and R ₄ are the same as each other. The method according to claim 1,
Wherein B is any one of the following formulas:

. The method according to claim 1,
Wherein L < _{1 >} and L < ₂ > are each independently any of the following formulas:

. 6. The method of claim 5,
Wherein L ₁ and L ₂ are each independently any one of the following formulas:

The method according to claim 1,
Wherein B is phenyl, and wherein R ₁ to R ₄ is methyl or phenyl, R ₁ and R ₂ are identical, R ₃ and R ₄ are the same with each other, wherein L ₁ and L ₂ is a bond, each independently from each other , The following formula (11), (12), and (21) to (25)

The method according to claim 1,
Wherein B is to a formula 4-1 or formula 4-2, wherein R ₁ to R ₄ is methyl or phenyl, R ₁ and R ₂ are the same and are the same each other, the R ₃ and R _4, wherein each L ₁ and L ₂ are each independently a direct bond, a compound represented by the following general formula (11), (12), and (21)

The method according to claim 1,
Wherein B is to a formula 5-1 or formula 5-2, wherein R ₁ to R ₄ is methyl or phenyl, R ₁ and R ₂ are the same and are the same each other, the R ₃ and R _4, wherein each L ₁ and L ₂ are each independently a direct bond, a compound represented by the following general formula (11), (12), and (21)

The method according to claim 1,
Wherein B is to a formula 6-1 or formula 6-2, wherein R ₁ to R ₄ is methyl or phenyl, R ₁ and R ₂ are the same and are the same each other, the R ₃ and R _4, wherein each L ₁ and L ₂ are each independently a direct bond, a compound represented by the following general formula (11), (12), and (21)

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 11 between a first electrode and a second electrode. 13. The method of claim 12,
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. 14. The method of claim 13,
Wherein the organic layer is a hole transport layer. 14. The method of claim 13,
Wherein the organic layer is a light emission-assisting layer.

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