KR20120125942A - Novel compound and organic light emitting device containing same - Google Patents

Abstract

PURPOSE: A compound with excellent luminous efficiency and low driving voltage and an organic light-emitting device including the same are provided to enhance stability and light emitting efficiencies. CONSTITUTION: A compound is represented by chemical formula 1. Here, R1-R14 are respectively hydrogen, deuterium, C1-60 substituted or non-substituted alkyl, C2-60 substituted or non-substituted alkenyl, C2-60 substituted or non-substituted alkynyl, C3-60 substituted or non-substituted cycloalkyl, C1-60 substituted or non-substituted alkoxy, C5-60 substituted or non-substituted aryloxy, C5-60 substituted or non-substituted arylthio, C5-60 substituted or non-substituted aryl, C5-60 aryl or C3-60 heteroaryl substituted amino, C3-60 substituted or non-substituted heteroaryl, and C6-60 substituted, non-substituted fused polycyclic group, halogen, cyano, nitro, hydroxy, or carboxy.

Description

Novel compound and organic light emitting device containing same

The present invention relates to a compound represented by Formula 1 and an organic light emitting device including the same.

Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has a merit of being lighter than a conventional cathode ray tube (CRT), but the viewing angle The disadvantage is that the angle is limited and the back light is necessary. In contrast, the organic light emitting diode (OLED), a new flat panel display device, is a display using a self-luminous phenomenon, and has a large viewing angle, can be thinner and shorter than a liquid crystal display, and has a fast response speed. In recent years, the application to full-color display or lighting is expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

An organic light emitting display device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

One aspect of the present invention is to provide a novel compound having a low driving voltage and excellent luminous efficiency.

Another aspect of the present invention is to provide an organic light emitting device comprising the compound.

Another aspect of the present invention is to provide a flat panel display device having the organic light emitting device.

According to one aspect of the invention, there is provided a compound represented by the formula (1):

≪ Formula 1 >

In Formula 1,

R ₁ to R ₁₄ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted group having 2 to 60 carbon atoms Alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or substituted with 5 to 60 carbon atoms, or Unsubstituted arylthio groups, substituted or unsubstituted aryl groups having 5 to 60 carbon atoms, amino groups substituted with aryl groups having 5 to 60 carbon atoms or heteroaryl groups having 3 to 60 carbon atoms, substituted or unsubstituted with 3 to 60 carbon atoms Heteroaryl group, substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, halogen atom, cyano group, nitro group, hydroxyl group or carboxyl group.

According to an embodiment of the present invention, in Formula 1, R ₁ to R ₁₄ are each independently hydrogen, deuterium, cyano group, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, 5 to 30 carbon atoms Substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, amino group substituted with aryl group having 5 to 30 carbon atoms or heteroaryl group having 3 to 30 carbon atoms, or substituted with 6 to 30 carbon atoms Or an unsubstituted condensed polycyclic group.

According to another embodiment of the present invention, in Formula 1, R ₁ to R ₁₄ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or the following formula May be from 2a to 2g:

In Formulas 2a to 2g, Q ₁ and Q ₂ are linking groups represented by —C (R ₂₀ ) (R ₂₁ ) —, —N (R ₂₀ ) —, —S— or —O—; Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =; Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Silyl group, wherein adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond; Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; p is an integer from 1 to 12; r is an integer from 0 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ may be each independently hydrogen or deuterium.

According to another embodiment of the present invention, in Formula 1, R ₂ and R ₁₁ may be the same substituent.

According to another embodiment of the present invention, R ₁ to R ₁₄ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 3 to 30 carbon atoms, or It may be an unsubstituted heteroaryl group, a substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms, or the following Chemical Formulas 3a to 3f:

In Formulas 3a to 3f, Z ₁ is a hydrogen atom, deuterium, or a substituted or unsubstituted aryl group having 5 to 20 carbon atoms; p is an integer from 1 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ may be each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or the following Chemical Formulas 2a to 2g:

In Formulas 2a to 2g, Q ₁ and Q ₂ are linking groups represented by —C (R ₂₀ ) (R ₂₁ ) —, —N (R ₂₀ ) —, —S— or —O—; Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =; Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Silyl group, wherein adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond; Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; p is an integer from 1 to 12; r is an integer from 0 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ may be each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or the following Chemical Formulas 3a to 3f:

In Formulas 3a to 3f, Z ₁ is a hydrogen atom, deuterium or a substituted or unsubstituted aryl group having 5 to 20 carbon atoms; p is an integer from 1 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or the following Chemical Formulas 2a to 2g, R ₂ And R ₁₁ may be the same substituent:

In Formulas 2a to 2g, Q ₁ and Q ₂ are linking groups represented by —C (R ₂₀ ) (R ₂₁ ) —, —N (R ₂₀ ) —, —S— or —O—; Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =; Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Silyl group, wherein adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond; Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; p is an integer from 1 to 12; r is an integer from 0 to 5; * Represents a bond.

According to another embodiment of the present invention, the compound of Formula 1 may be one of the following compounds:

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode; And an organic light emitting device having an organic layer interposed between the first electrode and the second electrode, the organic light emitting device including the compound represented by Formula 1 of claim 1.

According to an embodiment of the present invention, the organic layer is a functional layer having a hole injection layer, a hole transport layer, a hole injection and a hole transport function at the same time, an electron injection layer, an electron transport layer, or an electron injection and electron transport function at the same time Can be.

According to another embodiment of the present invention, the organic light emitting device may include an electron transport layer including an electron transporting organic material and a metal-containing material.

According to another embodiment of the present invention, the organic layer is a light emitting layer and the compound represented by Formula 1 may be used as a fluorescent or phosphorescent host.

According to another embodiment of the present invention, the organic light emitting device includes a light emitting layer, a hole transport layer and an electron transport layer, the light emitting layer may further include an anthracene compound, an arylamine compound or a styryl compound.

According to another embodiment of the present invention, the organic light emitting device includes a light emitting layer, a hole transport layer and an electron transport layer, wherein any one of the red layer, green layer, blue layer or white layer of the light emitting layer further contains a phosphorescent compound. It may include.

According to another embodiment of the present invention, the organic layer may be a red light emitting layer.

According to another embodiment of the present invention, the organic layer is a red light emitting layer, the compound of Formula 1 may be used as a red host.

According to another embodiment of the present invention, the organic layer may be formed by a wet process using the compound of Formula 1.

According to still another aspect of the present invention, there is provided a flat panel display device including the organic light emitting device, wherein the first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of the thin film transistor.

Since the new compound according to an embodiment of the present invention is stable and excellent light emission characteristics compared to the existing material, the organic light emitting device including the same may enable low voltage driving and improve light emission efficiency.

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

The material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order for the organic electroluminescent device to fully exhibit the above-mentioned excellent features, the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. is supported by a stable and efficient material Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Therefore, the development of new materials in the art continues to be required.

Hereinafter, the present invention will be described in detail.

According to one aspect of the invention, there is provided a compound represented by the formula (1):

≪ Formula 1 >

In Formula 1,

R ₁ to R ₁₄ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted group having 2 to 60 carbon atoms Alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or substituted with 5 to 60 carbon atoms, or Unsubstituted arylthio groups, substituted or unsubstituted aryl groups having 5 to 60 carbon atoms, amino groups substituted with aryl groups having 5 to 60 carbon atoms or heteroaryl groups having 3 to 60 carbon atoms, substituted or unsubstituted with 3 to 60 carbon atoms A heteroaryl group, a substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group.

Compound of Formula 1 according to an embodiment of the present invention has a function as a light emitting material for an organic light emitting device. Compounds of the same type as Formula 1 are stable and have excellent luminescent properties. The organic electroluminescent device manufactured using the compound of Formula 1 according to an embodiment of the present invention can be driven at a low voltage and the luminous efficiency is improved.

The substituent of the compound of Formula 1 will be described in more detail.

According to an embodiment of the present invention, in Formula 1, R ₁ to R ₁₄ are each independently hydrogen, deuterium, cyano group, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, 5 to 30 carbon atoms Substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, amino group substituted with aryl group having 5 to 30 carbon atoms or heteroaryl group having 3 to 30 carbon atoms, or substituted with 6 to 30 carbon atoms Or an unsubstituted condensed polycyclic group.

According to another embodiment of the present invention, in Formula 1, R ₁ to R ₁₄ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or the following formula May be from 2a to 2g:

In Formulas 2a to 2g, Q ₁ and Q ₂ are linking groups represented by —C (R ₂₀ ) (R ₂₁ ) —, —N (R ₂₀ ) —, —S— or —O—; Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =; Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Silyl group, wherein adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond; Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; p is an integer from 1 to 12; r is an integer from 0 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ may be each independently hydrogen or deuterium.

According to another embodiment of the present invention, in Formula 1, R ₂ and R ₁₁ may be the same substituent.

According to another embodiment of the present invention, R ₁ to R ₁₄ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 3 to 30 carbon atoms, or It may be an unsubstituted heteroaryl group, a substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms, or the following Chemical Formulas 3a to 3f:

In Formulas 3a to 3f, Z ₁ is a hydrogen atom, deuterium, or a substituted or unsubstituted aryl group having 5 to 20 carbon atoms; p is an integer from 1 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ may be each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or the following Chemical Formulas 2a to 2g:

In Formulas 2a to 2g, Q ₁ and Q ₂ are linking groups represented by —C (R ₂₀ ) (R ₂₁ ) —, —N (R ₂₀ ) —, —S— or —O—; Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =; Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Silyl group, wherein adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond; Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; p is an integer from 1 to 12; r is an integer from 0 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ may be each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or the following Chemical Formulas 3a to 3f:

In Formulas 3a to 3f, Z ₁ is a hydrogen atom, deuterium or a substituted or unsubstituted aryl group having 5 to 20 carbon atoms; p is an integer from 1 to 5; * Represents a bond.

According to another embodiment of the present invention, in Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or the following Chemical Formulas 2a to 2g, R ₂ And R ₁₁ may be the same substituent:

In Formulas 2a to 2g, Q ₁ and Q ₂ are linking groups represented by —C (R ₂₀ ) (R ₂₁ ) —, —N (R ₂₀ ) —, —S— or —O—; Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =; Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Wherein, adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond (eg, in Formula 2c, Q ₁ may be -C (R ₂₀ ) (R ₂₁ )-and R ₂₀ , R ₂₁ Is a phenyl group, R ₂₀ And when R ₂₁ is connected in a single bond, forms a spheroene group as a spy); Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; p is an integer from 1 to 12; r is an integer from 0 to 5; * Represents a bond.

Hereinafter, the definition of a representative group among the groups used in the chemical formulas of the present invention is as follows (the number of carbons defining a substituent is not limited and does not limit the properties of substituents).

In the above formula, unsubstituted carbon of 1 to 60 Alkyl groups may be linear and branched and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, nonanyl, , At least one hydrogen atom of the alkyl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, 1 to 10 carbon atoms Alkyl group, 1 to 10 carbon atoms Alkoxy group, 2 to 10 carbon atoms An alkenyl group having 2 to 10 carbon atoms An alkynyl group, an aryl group having 6 to 16 carbon atoms, or an aryl group having 4 to 16 carbon atoms And may be substituted with a heteroaryl group.

In the above formula, an unsubstituted alkenyl group having 2 to 60 carbon atoms means that the unsubstituted alkyl group contains at least one carbon double bond. Examples include ethenyl, propenyl, butenyl, and the like. At least one hydrogen atom in these unsubstituted alkenyl groups may be substituted with the same substituent as in the case of the substituted alkyl group described above.

In the above formula, an unsubstituted alkynyl group having 2 to 60 carbon atoms means containing at least one carbon triple bond in an alkyl group as defined above. Examples include acetylene, propylene, phenylacetylene, naphthylacetylene, isopropylacetylene, t-butylacetylene, diphenylacetylene, and the like. At least one hydrogen atom in these alkynyl groups may be substituted with the same substituent as in the case of the substituted alkyl group described above.

In the above formula, an unsubstituted cycloalkyl group having 3 to 60 carbon atoms means an alkyl group having 3 to 60 carbon atoms, and at least one hydrogen atom of the cycloalkyl group is the same as the substituent of the alkyl group having 1 to 60 carbon atoms. Substitutable with a substituent.

In the above formula, an unsubstituted alkoxy group having 1 to 60 carbon atoms is -OA, wherein A is an unsubstituted carbon having 1 to 60 carbon atoms as described above. Alkyl group), examples of which include, but are not limited to, methoxy, ethoxy, propoxy, isopropyloxy, butoxy, pentoxy, and the like. At least one hydrogen atom of these alkoxy groups may be substituted with the same substituent as in the alkyl group described above.

In the above formula, an unsubstituted aryl group having 5 to 60 carbon atoms means a carbocycle aromatic system including one or more rings, and when having two or more rings, may be fused to each other or connected through a single bond or the like. The term aryl includes aromatic systems such as phenyl, naphthyl, anthracenyl. At least one of the hydrogen atoms of the aryl group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

Examples of the substituted or unsubstituted aryl group having 5 to 60 carbon atoms include phenyl group and 1 to 10 carbon atoms. (E.g., o-, m- and p-fluorophenyl groups, dichlorophenyl groups), cyanophenyl groups, dicyanophenyl groups, trifluoromethoxyphenyl groups, biphenyl groups , A halobiphenyl group, a cyanobiphenyl group, a group having 1 to 10 carbon atoms An alkylphenyl group, an alkylphenyl group having 1 to 10 carbon atoms M, and p-tolyl groups, o-, m-, and p-cumenyl groups, mesityl groups, phenoxyphenyl groups, (?,? - dimethylbenzene) phenyl groups, Naphthyl group, halonaphthyl group (for example, fluoronaphthyl group) having 1 to 10 carbon atoms, a monovalent group having 1 to 10 carbon atoms Alkyl naphthyl group (for example, methyl naphthyl group), C1-C10 An acenaphthyl group, a phenaranyl group, a fluorenyl group, an anthraquinolyl group, a methylene group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, A phenanthryl group, a triphenylene group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, A phenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, and an obarenyl group.

In the above formula, an unsubstituted heteroaryl group having 4 to 60 carbon atoms includes 1, 2 or 3 heteroatoms selected from N, O, P or S, and when they have two or more rings, they may be fused to each other or a single bond And so on. Unsubstituted 4 to 60 carbon atoms Examples of the heteroaryl group include a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, A benzoyl group, a carbazolyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, and a dibenzothiophen group. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

In the above formula, an unsubstituted aryloxy group having 5 to 60 carbon atoms is a group represented by -OA ₁ , wherein A ₁ is an aryl group having 5 to 60 carbon atoms. Examples of the aryloxy group include a phenoxy group and the like. At least one hydrogen atom of the aryloxy group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms.

In the formula, an unsubstituted arylthio group having 5 to 60 carbon atoms is a group represented by -SA ₁ , where A ₁ is an aryl group having 5 to 60 carbon atoms. Examples of the arylthio group include benzenethio group, naphthylthio group and the like. At least one hydrogen atom of the arylthio group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms described above.

In the above formula, unsubstituted 6 to 60 carbon atoms A condensed polycyclic group means a substituent including two or more rings in which one or more aromatic rings and / or one or more non-aromatic rings are fused to each other, and are distinguished from aral groups or heteroaryl groups in the sense that they do not have an overall aromaticity. At least one hydrogen atom of the condensed polycyclic group may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms described above.

In one embodiment of the present invention, non-limiting examples of the substituted condensed polycyclic group include the following compound structure.

The description of R ₂₀ and * is as described above.

Hereinafter, specific examples of the compound represented by Formula 1 of the present invention include the following compounds 10 to 373. However, the compound represented by Formula 1 of the present invention should not be limited to these compounds.

[Formula 10] [Formula 11] [Formula 12] [Formula 13] [Formula 14]

[Formula 15] [Formula 16] [Formula 17] [Formula 18] [Formula 19]

[Formula 20] [Formula 21] [Formula 22]

[Formula 23] [Formula 24] [Formula 25] [Formula 26] [Formula 27]

[Formula 28] [Formula 29] [Formula 30] [Formula 31] [Formula 32]

[Formula 33] [Formula 34] [Formula 35] [Formula 36] [Formula 37]

[Formula 38] [Formula 39] [Formula 40] [Formula 41] [Formula 42]

[Formula 43] [Formula 44] [Formula 45] [Formula 46] [Formula 47]

[Formula 48] [Formula 49] [Formula 50] [Formula 51] [Formula 52]

[Formula 53] [Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Formula 58] [Formula 59] [Formula 60] [Formula 61] [Formula 62]

[Formula 63] [Formula 64] [Formula 65] [Formula 66] [Formula 67]

[Formula 68] [Formula 69] [Formula 70] [Formula 71]

[Formula 72] [Formula 73] [Formula 74] [Formula 75] [Formula 76]

[Formula 77] [Formula 78] [Formula 79] [Formula 80] [Formula 81]

[Formula 82] [Formula 83] [Formula 84] [Formula 85] [Formula 86]

[Formula 87] [Formula 88] [Formula 89] [Formula 90] [Formula 91]

[Formula 92] [Formula 93] [Formula 94] [Formula 95] [Formula 96]

[Formula 97] [Formula 98] [Formula 99] [Formula 100] [Formula 101]

[Formula 102] [Formula 103] [Formula 104] [Formula 105] [Formula 106]

[Formula 107] [Formula 108] [Formula 109] [Formula 110] [Formula 111]

[Formula 112] [Formula 113] [Formula 114] [Formula 115] [Formula 116]

[Formula 117] [Formula 118] [Formula 119] [Formula 120] [Formula 121]

[Formula 122] [Formula 123] [Formula 124] [Formula 125] [Formula 126]

[Formula 127] [Formula 128] [Formula 129] [Formula 130] [Formula 131]

[Formula 132] [Formula 133] [Formula 134] [Formula 135]

[Formula 136] [Formula 137] [Formula 138] [Formula 139]

[Formula 140] [Formula 141] [Formula 142] [Formula 143]

   [Formula 144] [Formula 145] [Formula 146] [Formula 147]

   [Formula 148] [Formula 149] [Formula 150] [Formula 151]

[Formula 152] [Formula 153] [Formula 154] [Formula 155]

[Formula 156] [Formula 157] [Formula 158] [Formula 159]

[Formula 160] [Formula 161] [Formula 162] [Formula 163]

[Formula 164] [Formula 165] [Formula 166] [Formula 167]

[Formula 168] [Formula 169] [Formula 170] [Formula 171]

[Formula 172] [Formula 173] [Formula 174] [Formula 175]

[Formula 176] [Formula 177] [Formula 178] [Formula 179]

[Formula 180] [Formula 181] [Formula 182] [Formula 183]

[Formula 184] [Formula 185] [Formula 186] [Formula 187]

[Formula 188] [Formula 189] [Formula 190] [Formula 191]

[Formula 192] [Formula 193] [Formula 194] [Formula 195]

[Formula 196] [Formula 197] [Formula 198] [Formula 199]

[Formula 200] [Formula 201] [Formula 202] [Formula 203]

[Formula 204] [Formula 205] [Formula 206] [Formula 207]

[Formula 208] [Formula 209] [Formula 210] [Formula 211]

[Formula 212] [Formula 213] [Formula 214] [Formula 215]

[Formula 216] [Formula 217] [Formula 218] [Formula 219]

[Formula 220] [Formula 221] [Formula 222] [Formula 223]

[Formula 224] [Formula 225] [Formula 226] [Formula 227]

[Formula 228] [Formula 229] [Formula 230] [Formula 231]

[Formula 232] [Formula 233] [Formula 234] [Formula 235]

[Formula 236] [Formula 237] [Formula 238] [Formula 239]

[Formula 240] [Formula 241] [Formula 242] [Formula 243]

[Formula 244] [Formula 245] [Formula 246] [Formula 247]

[Formula 248] [Formula 249] [Formula 250] [Formula 251]

[Formula 252] [Formula 253] [Formula 254] [Formula 255]

[Formula 256] [Formula 257] [Formula 258] [Formula 259]

[Formula 260] [Formula 261] [Formula 262] [Formula 263]

[Formula 264] [Formula 265] [Formula 266] [Formula 267]

[Formula 268] [Formula 269] [Formula 270] [Formula 271]

[Formula 272] [Formula 273] [Formula 274] [Formula 275]

[Formula 276] [Formula 277] [Formula 278] [Formula 279]

[Formula 280] [Formula 281] [Formula 282] [Formula 283]

[Formula 284] [Formula 285] [Formula 286] [Formula 287]

[Formula 288] [Formula 289] [Formula 290] [Formula 291]

[Formula 292] [Formula 293] [Formula 294] [Formula 295]

[Formula 296] [Formula 297] [Formula 298] [Formula 299]

[Formula 300] [Formula 301] [Formula 302] [Formula 303]

[Formula 304] [Formula 305] [Formula 306] [Formula 307]

[Formula 308] [Formula 309] [Formula 310] [Formula 311]

[Formula 312] [Formula 313] [Formula 314] [Formula 315]

[Formula 316] [Formula 317] [Formula 318] [Formula 319]

[Formula 320] [Formula 321] [Formula 322] [Formula 323]

[Formula 324] [Formula 325] [Formula 326] [Formula 327] [Formula 328]

[Formula 329] [Formula 330] [Formula 331] [Formula 332] [Formula 333]

According to another aspect of the invention, the first electrode; A second electrode; And an organic light emitting device having an organic layer interposed between the first electrode and the second electrode, and an organic light emitting device including an organic layer including the compound represented by Formula 1 above.

The organic layer including the compound represented by Chemical Formula 1 may be a functional layer having a hole injection layer, a hole transport layer, a hole injection and a hole transport function at the same time, an electron injection layer, an electron transport layer, or an electron injection and electron transport function simultaneously. Can be.

Alternatively, the organic layer may be a light emitting layer, and the compound represented by Chemical Formula 1 may be used as a fluorescent or phosphorescent host.

According to one embodiment of the present invention, the organic light emitting device includes a light emitting layer, a hole transport layer and an electron transport layer, the light emitting layer may further include a known anthracene compound, arylamine compound or styryl compound.

At least one hydrogen atom of the anthracene compound, arylamine compound or styryl compound may be substituted with the same substituent as the substituent of the alkyl group having 1 to 60 carbon atoms described above. The arylamine means an arylamine group having 5 to 60 carbon atoms.

An organic light emitting device according to an embodiment of the present invention includes a light emitting layer, a hole transport layer and an electron transport layer, any one of the red layer, green layer, blue layer or white layer of the light emitting layer may further include a phosphorescent compound. .

The organic layer of the organic light emitting device according to the embodiment of the present invention may be a red light emitting layer. When the organic layer of the organic light emitting device is a red light emitting layer, the compound of Formula 1 may be used as a red host.

Meanwhile, the first electrode may be an anode and the second electrode may be a cathode, and vice versa.

For example, the organic light emitting device according to the embodiment of the present invention, the first electrode / hole injection layer / light emitting layer / second electrode, the first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / second electrode Or a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode structure. Alternatively, the organic light emitting device may be a single layer / light emitting layer / electron transport layer / second electrode having a first electrode / hole injection function and a hole transport function at the same time, or a single film / light emitting layer having a first electrode / hole injection function and a hole transport function at the same time. / Electron transport layer / electron injection layer / second electrode structure. Alternatively, the organic light emitting device has a single electrode / hole having a first electrode / hole transporting layer / light emitting layer / electron injection and electron transport and electron transport and simultaneously having a first electrode / hole injection layer / light emitting layer / electron injection and electron transport. It can have a single film / second electrode, or a single film / second electrode structure having a first electrode / hole injection layer / hole transport layer / light emitting layer / electron injection and electron transport function at the same time.

The organic light emitting device according to the embodiment of the present invention can be applied in various structures such as a top emission type, a bottom emission type.

The organic layer of the organic light emitting device according to an embodiment of the present invention is a functional layer having a hole injection layer, a hole transport layer, a hole injection layer and a hole transport function at the same time, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer or the It may further include a combination of two or more, but is not limited thereto.

At least one of a hole injection layer, a hole transport layer, or a functional layer having a hole injection function and a hole transport function of an organic light emitting device according to an embodiment of the present invention is a compound according to an embodiment of the present invention, a known hole injection In addition to the materials and known hole transport materials, a charge-generating material may be further included to improve the conductivity of the film and the like.

The charge-generating material may be, for example, a p-dopant. Non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4TCNQ) Quinone derivatives such as these; Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as Compound 100, and the like, but are not limited thereto.

<Compound 100>

When the hole injection layer, the hole transport layer, or the functional layer having the hole injection function and the hole transport function at the same time further include the charge-generating material, the charge-generating material is uniformly dispersed or non-uniform in the layers. Various modifications are possible, such as may be distributed.

The electron transport layer of the organic light emitting device according to the embodiment of the present invention may include an electron transport organic compound and a metal-containing material. Non-limiting examples of the electron transporting organic compound include ADN (9,10-di (naphthalen-2-yl) anthracene); And anthracene-based compounds such as Compounds 101 and 102, but are not limited thereto.

<Compound 101> <Compound 102>

  The metal-containing material may comprise a Li complex. Non-limiting examples of the Li complex include lithium quinolate (LiQ) or the following compound 103:

<Compound 103>

Hereinafter, a method of manufacturing an organic light emitting diode according to the present invention will be described with reference to the organic light emitting diode illustrated in FIG. 1. 1 includes a substrate, a first electrode (anode), a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a second electrode (cathode).

First, the first electrode material having a high work function on the substrate is formed by vapor deposition, sputtering, or the like to form the first electrode. The first electrode may be an anode or a cathode. Herein, a substrate used in a conventional organic light emitting device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the first electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), Al, Ag, Mg and the like having excellent conductivity may be used. Or a reflective electrode.

Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

When the hole injection layer is formed by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable to select suitably in the range of a vacuum degree of 10 ^-8 to 10 ^-3 torr and a deposition rate of 0.01 to 100 kPa / sec.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal characteristics of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. , The heat treatment temperature for removing the solvent after coating is preferably selected in the temperature range of about 80 ℃ to 200 ℃.

As the hole injection material, a well-known hole injection material may be used. For example, a phthalocyanine compound such as copper phthalocyanine, m-MTDATA [4,4 ', 4' '-tris (3-methylphenylphenylamino) triphenylamine], NPB (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine) (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine)), TDATA, 2T-NATA , Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor sulfonicacid: polyaniline / camphorsulfonic acid) or PANI / PSS (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate) ) May be used, but is not limited thereto.

The thickness of the hole injection layer may be about 100 Å to 10000 Å, preferably 100 Å to 1000 Å. When the thickness of the hole injection layer satisfies the above range, excellent hole injection characteristics may be obtained without increasing a driving voltage.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. In the case of forming the hole transport layer by vacuum deposition and spin coating, the deposition conditions and coating conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The hole transport layer material may be a known hole transport layer material, for example, carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, NPB, N, N'-bis (3-methylphenyl) -N Amine derivatives having an aromatic condensed ring such as, N'-diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD) and the like can be used.

The hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. When the thickness of the hole transport layer satisfies the above range, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.

Next, an emission layer (EML) may be formed on the hole transport layer by using a method such as vacuum deposition, spin coating, casting, and LB. When the light emitting layer is formed by a vacuum deposition method or a spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from a range of conditions almost the same as that of forming the hole injection layer.

The emission layer may include a compound represented by Formula 1 as described above. For example, the compound represented by Formula 1 may be used as a host or dopant. In addition to the compound represented by Chemical Formula 1, the light emitting layer may be formed using various known light emitting materials, and may be formed using a known host and a dopant. In the case of the above-mentioned dopant, a known fluorescent dopant and a known phosphorescent dopant can be used.

For example, known hosts include Alq ₃ , CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole)), 9,10-di (naphthalene -2-yl) anthracene (ADN), TPBI (1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene (1,3,5-tris (N-phenylbenzimidazole-2-yl) benzene )), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene) and the like can be used, but is not limited thereto.

             PVK

On the other hand, PtOEP, Ir (piq) ₃ , Btp ₂ Ir (acac), DCJTB and the like can be used as a known red dopant, but is not limited thereto.

Ir (ppy) ₃ (ppy = phenylpyridine), Ir (ppy) ₂ (acac), Ir (mpyp) ₃ and C545T may be used as the known green dopant. However, the present invention is not limited thereto.

              C545T

On the other hand, as a known blue dopant, F ₂ Irpic, (F ₂ ppy) ₂ Ir (tmd), Ir (dfppz) ₃ , ter-fluorene, 4,4'-bis (4-diphenylaminostar Aryl) biphenyl (DPAVBi), 2,5,8,11-tetra- ti -butyl perylene (TBP), and the like, but are not limited thereto.

                   DPAVBi TBP

The content of the dopant is preferably 0.1 to 20 parts by weight, particularly 0.5 to 12 parts by weight, based on 100 parts by weight of the light emitting layer forming material (ie, the total weight of the host and the dopant is 100 parts by weight). When the content of the dopant satisfies the above range, concentration quenching phenomenon can be substantially prevented.

The thickness of the light emitting layer may be about 100 Å to 1000 Å, preferably 200 Å to 600 Å. When the thickness of the light emitting layer satisfies the above range, excellent light emission characteristics may be obtained without a substantial increase in driving voltage.

When the light emitting layer includes a phosphorescent dopant, a hole blocking layer HBL may be formed on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer (not shown in FIG. 1). The hole blocking layer material that can be used at this time is not particularly limited, and may be selected arbitrarily from known hole blocking layer materials. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, Balq, BCP, and the like can be used.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. When the thickness of the hole blocking layer is within the above range, it is possible to prevent diffusion of triplet excitons or holes into the electron transport layer without a substantial increase in driving voltage.

Next, the electron transport layer (ETL) is formed by various methods such as vacuum deposition, spin coating, casting or the like. In the case of forming the electron transporting layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound to be used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The electron transport layer material may be arbitrarily selected from known electron transport layer forming materials. For example, a quinoline derivative, in particular, a known material such as tris (8-quinolinorate) aluminum (Alq ₃ ), TAZ, Balq and the like may be used, but is not limited thereto.

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 100 kPa to 500 kPa. When the thickness of the electron transport layer satisfies the above range, excellent electron transport characteristics can be obtained without a substantial increase in driving voltage.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer.

As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li ₂ O, BaO or the like can be used. Although the deposition conditions and coating conditions of the electron injection layer vary depending on the compound used, they are generally selected from the range of conditions almost the same as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 90 kPa. When the thickness of the electron injection layer satisfies the above range, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.

Finally, the second electrode can be formed on the electron injection layer by using a method such as vacuum deposition or sputtering. The second electrode may be used as a cathode or an anode. As the material for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, or a mixture thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- . In addition, it is also possible to use a transparent cathode using ITO, IZO to obtain a top light emitting device.

The organic light emitting device according to the present invention may be provided in various types of flat panel display devices, for example, a passive matrix organic light emitting display device and an active matrix organic light emitting display device. In particular, when provided in the active matrix organic light emitting display device, the first electrode provided on the substrate side may be electrically connected to the source electrode or the drain electrode of the thin film transistor as the pixel electrode. In addition, the organic light emitting device may be provided in a flat panel display device capable of displaying a screen on both sides.

In addition, when the organic layer of the organic light emitting device according to an embodiment of the present invention consists of a plurality of organic layers, at least one layer of the organic layer may be formed by a deposition method using a compound represented by the formula (1), or as a solution It may also be formed by a wet method of coating the prepared compound of formula (1).

Hereinafter, the specific synthesis examples and examples of the compounds 10, 24, 28, 29, 83, 144, 231 and 330 of the present invention are specifically illustrated, but the present invention is not meant to be limited to the following examples. .

[Example]

Synthetic example  1.Synthesis of Formula 28

1-1. Synthesis of 1-a

<1-a> was synthesized according to Scheme 1 below.

[Reaction Scheme 1]

                                                   <1-a>

In 250 ml round bottom flask was added 1-bromo-2-iodo-benzene 30.0 g (0.106 mol) and copper (I) iodide 1.01 g (0.0005 mol) and _{Pd (pph 3) 4 2.45 g} (0.002 mol) and tri Add 180 ml of ethylamine and stir. Lower the temperature of the reaction to 0 degrees and slowly add dropwise 11.9 g (0.117 mol) of phenyl acetylene. The reaction is terminated after stirring for 1 hour. Add 1 L of normal-hexane, stir and filter to remove impurities and rinse thoroughly. The filtrate was concentrated and dried to give 25.0 g (85.8%) of <1-a>.

1-2. Synthesis of 1-b

<1-b> was synthesized by the following Scheme 2.

Scheme 2

                                                 <1-b>

Dissolve 25.0 g (0.097 mol) of <1-a> obtained in Scheme 1 in 250 ml of tetrahydrofuran in a 500 ml round bottom flask, stir for 30 minutes under nitrogen, lower the temperature of the reaction to -78 ° C, and prepare 1.6 mol hexane solution. 79 ml of normal butyllithium is added dropwise for 30 minutes. After stirring for 2 hours at the same temperature, 83.3 ml (0.194 mol) of trimethylborate are added dropwise for 30 minutes. After dropping, the temperature was increased to room temperature, followed by stirring for 3 hours, and then adjusted to pH 2 using 2N aqueous hydrochloric acid solution. The organic layer was separated using ethyl ether and water, concentrated under reduced pressure, poured into normal-hexane, stirred for 1 hour, and filtered to obtain 18.00 g (83.5%) of solid <1-b>.

1-3. Synthesis of 1-c

&Lt; 1-c > was synthesized by the following Reaction Scheme 3.

Scheme 3

                                                             <1-c>

121.8 g (0.446 mol) of 2-bromo-9,9'-dimethyl florene was dissolved in 800 ml of tetrahydrofuran in a 2000 ml round-bottom flask, stirred for 20 minutes under nitrogen, and the reaction temperature reached -78 ° C. 263 ml of normal butyllithium in 1.6 mol hexane solution is added dropwise. After stirring for 2 hours at the same temperature 40 g (0.139 mol) of 2-bromo anthraquinone was added. After stirring for 30 minutes at the same temperature, the temperature is raised to room temperature, and after stirring for 3 hours, the pH is adjusted to 2 using aqueous 2N hydrochloric acid solution. The organic layer is separated using ethyl ether and water, concentrated under reduced pressure and dried. The dried material is dispersed in 600 ml of acetic acid, and 69.38 g (0.418 mol) of potassium iodide and 88.60 g (0.836 mol) of sodium hypophosphite are refluxed for 2 hours. The resulting solid was filtered under reduced pressure, washed with water and ethanol, recrystallized with toluene, and dried to obtain 64.0 g (71.9%) of <1-c>.

1-4. Synthesis of 1-d

<1-d> was synthesized according to Scheme 4 below.

[Reaction Scheme 4]

                                                   <1-d>

In a 500 ml round bottom flask, <1-c> from reaction 1-3 and <1-b> from reaction 1-2, 1.44 g (0.001 mol) of Pd (pph ₃ ) ₄ and 17.23 g of potassium carbonate ( 0.125 mol), add 200 ml of toluene, 200 ml of dioxane and 80 ml of water and reflux for 12 hours. At the end of the reaction the reaction is depressurized to give a solid. The organic layer was separated using ethyl ether and water, concentrated under reduced pressure, hexane and methylene chloride were used as a developing solvent, separated by column chromatography, and the solid was dried to give 25.0 g (54.8%) of <1-d>.

1-5. Synthesis of Formula 28

Formula 28 was synthesized according to Scheme 5 below.

Scheme 5

                                        (28)

Into a 2000 ml round bottom flask, <1-e> obtained from Reaction 1-4 was added and 800 ml of dichloroethane was added to the flask and stirred. Add 17.0 g (0.034 mol) of iron (II) trichloromethane sulfonate and reflux for 12 hours. At the end of the reaction, hot methylene chloride is poured to reduce the pressure. The filtrate was concentrated, separated by column chromatography using hexane and methylene chloride as a developing solvent, recrystallized with tetrahydrofuran and dried to give 6.1 g (23.5%) of the formula (28).

MS (MALDI-TOF): m / z = 738.33 [M] ⁺

Elemental Analysis (EA): Theoretical-C. 94.27%; H. 5.73%

                         Found-C. 95.35%; H. 4.65%

1 H NMR (CDCl ₃ ): δ 8.71 (d, 1H, Ar- H ), δ 8.3 (s, 2H, Ar- H ), δ 8.12 (d, 1H, Ar- H ), δ 7.91 ~ 7.69 (m, 10H, Ar- H ), δ 7.59-7.32 (m, 16H, Ar- H ), δ 1.59 (d, 12H, -C H ₃ )

Synthetic example  2. Synthesis of Chemical Formula 24

2-1. Synthesis of 2-a

<2-a> was synthesized according to Scheme 6 below.

[Reaction Scheme 6]

                                                        <2-a>

6.5 g (38.0%) of <2-a> was synthesized in the same manner except that 2-bromonaphthalene was used instead of 2-bromo-9,9'-dimethylfluorene used in the synthesis of Scheme 3. )

2-2. Synthesis of 2-b

<2-b> was synthesized by the following Scheme 7.

[Reaction Scheme 7]

                                                           <2-b>

Except for using <2-a> instead of <1-d> used in the synthesis of Scheme 4 it was synthesized in the same manner to obtain 8.8 g (44.1%) of <2-b>.

2-2. Synthesis of Formula 27

Formula 24 was synthesized according to Scheme 8 below.

[Reaction Scheme 8]

                                                 <Formula 24>

Synthesis was carried out in the same manner, except that <2-b> was used instead of <1-e> used in the synthesis of Scheme 5 to obtain 1.3 g (13.3%).

MS (MALDI-TOF): m / z = 606.23 [M] ⁺

Elemental Analysis (EA): Theoretical-C. 95.02%; H. 4.98%

                         Found-C. 94.68%; H. 5.32%

1 H NMR (CDCl ₃ ): δ 8.85 (d, 1H, Ar- H ), δ 8.28 (s, 2H, Ar- H ), δ 8.11 (d, 1H, Ar- H ), δ 7.96 ~ 7.72 (m, 8H, Ar- H ), δ 7.61-7.36 (m, 14H, Ar- H )

Synthetic example  3. Synthesis of Chemical Formula 83

3-1. Synthesis of Formula 3-a

<3-a> was synthesized by the following Scheme 9.

Scheme 9

                                                    <3-a>

Synthesis was carried out in the same manner, except that 3-ethynyl pyridine was used instead of phenyl acetylene used in the synthesis of Scheme 1, to obtain 10.4 g (95.0%) of <3-a>.

3-2. Synthesis of Formula 3-b

<3-b> was synthesized by the following Scheme 10.

[Reaction Scheme 10]

                                                  <3-b>

Synthesis was carried out in the same manner, except that <3-a> was used instead of <2-a> used in the synthesis of Scheme 2 to obtain 6.0 g (66.8%) of <3-b>.

3-3. Synthesis of Formula 3-c

<3-c> was synthesized by the following Scheme 11.

[Reaction Scheme 11]

                                                        <3-c>

Except for using <3-b> instead of <1-d> used in the synthesis of Scheme 4 it was synthesized in the same manner to give <0.01, 10.0 g, (64.5%).

3-4. Synthesis of Formula 83

Formula 83 was synthesized according to Scheme 12 below.

[Reaction Scheme 12]

                                      <Formula 83>

Except for using <3-c> instead of <1-d> used in the synthesis of Scheme 5 it was synthesized in the same manner to obtain 1.5 g, (25.0%) of the formula 83.

MS (MALDI-TOF): m / z = 607.23 [M] ⁺

Elemental Analysis (EA): Theoretical-C. 92.89%; H. 4.81%; N. 2.30

                         Found-C. 93.15%; H. 4.74%; N. 2.11

1 H NMR (CDCl ₃ ): δ 8.92 (s, 1H, Ar- H ), δ 8.83 (d, 1H, Ar- H ), δ 8.66 (d, 1H, Ar- H ), δ 8.30 (s, 2H, Ar- H ), δ 8.11 (d, 1H, Ar- H ), δ 8.00-7.80 (m, 10H, Ar- H ), δ 7.65-7.43 (m, 13H, Ar- H )

Synthetic example  4. Synthesis of Chemical Formula 330

4-1. Synthesis of 4-a

<4-a> was synthesized by the following Scheme 13.

[Reaction Scheme 13]

                                     <4-a>

In a 1000 ml round bottom flask, 54.0 g (0.21 mol) of 3-bromo-4-aminobiphenyl and 300 ml of hydrochloric acid are added and the temperature is reduced to 0 degrees. 24.4 g (0.21 mol) of sodium nitrite solution are slowly added dropwise. Stir at the same temperature for 1 hour, raise the temperature to 100 degrees, reflux for 1 hour and terminate the reaction. The organics are separated by chloroform and water and concentrated under reduced pressure. Hexane was separated by column chromatography with a developing solvent, concentrated and dried to give 34.5 g (47.0%) of <4-a>.

4-2. Synthesis of Formula 4-b

<4-b> was synthesized by the following Scheme 14.

[Reaction Scheme 14]

                                                <4-b>

Synthesis was carried out in the same manner, except that 3-bromo-4-iodobiphenyl was used instead of 1-bromo-2-iodobenzene used in the synthesis of Scheme 1, and 26.3 g ( 82.0%).

4-3. Synthesis of Formula 4-c

<4-c> was synthesized by the following Scheme 15.

[Reaction Scheme 15]

                                                <4-c>

Except for using <4-b> instead of <2-a> used in the synthesis of Scheme 2, it was synthesized in the same manner to give 12.1 g, (51.3%).

4-4. Synthesis of Formula 4-d

<4-d> was synthesized according to Scheme 16 below.

[Reaction Scheme 16]

                                                <4-d>

Except for using 4-bromo biphenyl instead of 2-bromo-9,9-dimethylfluorene used in the synthesis of Scheme 3, 36.2 g (60.0%) of <4-d> in the same manner )

4-5. Synthesis of Formula 4-e

Formula 4-e was synthesized according to Scheme 17 below.

[Reaction Scheme 17]

                                                    <Formula 4-e>

Except for using <4-c> instead of <1-b> used in the synthesis of Scheme 4 it was synthesized in the same manner to obtain the formula 4-e 16.1 g, (34.1%).

4-6. Synthesis of Chemical Formula 330

Formula 330 was synthesized according to Scheme 18 below.

[Reaction Scheme 18]

                                        <Formula 330>

Except for using <4-e> instead of <1-d> synthesized in Scheme 4 it was synthesized in the same manner to obtain 3.38 g, (21.0%) of the formula 330.

MS (MALDI-TOF): m / z = 734.30 [M] ⁺

Elemental Analysis (EA): Theoretical-C. 94.79%; H. 5.21%

                        Found-C. 95.24%; H. 4.76%

1 H NMR (CDCl ₃ ): δ 8.79 (d, 1H, Ar- H ), δ 8.31 (s, 2H, Ar- H ), δ 8.20 (d, 1H, Ar- H ), δ 8.04 (d, 1H, Ar- H ), δ 7.88-7.70 (m, 12H, Ar- H ), δ 7.56-7.21 (m, 21H, Ar- H )

Synthetic example  5. Synthesis of Chemical Formula 29

5-1. Synthesis of 5-a

&Lt; 5-a > was synthesized according to the following Reaction Scheme 19.

Scheme 19

                                                      <5-a>

Synthesis was carried out in the same manner, except that 9,10-biphenyl-2-bromo anthracene was used instead of <1-e> used in the synthesis of Scheme 5 to obtain 16 g (57.8%) of 5-a.

5-2. Synthesis of 5-b

Formula 29 was synthesized according to Scheme 20 below.

[Reaction Scheme 20]

                                 (29)

Except for using <5-a> instead of <1-e> used in the synthesis of Scheme 5, 4.5 g (13.3%) was obtained by the same method.

MS (MALDI-TOF): m / z = 658.27 [M] ⁺

Elemental Analysis (EA): Theoretical-C. 94.80%; H. 5.20%

                         Found-C. 94.99%; H. 5.01%

1 H NMR (CDCl ₃ ): δ 8.74 (d, 1H, Ar- H ), δ 8.32 (s, 2H, Ar- H ), δ 8.16 (d, 1H, Ar- H ), δ 7.94 ~ 7.76 (m, 12H, Ar- H ), δ 7.54-7.21 (m, 18H, Ar- H )

Synthetic example  6. Synthesis of Chemical Formula 10

6-1. Synthesis of 6-a

&Lt; 6-a > was synthesized according to the following Reaction Formula 21.

Scheme 21

                                                   <6-a>

Except for using 1-naphthalene boronic acid in place of 2-bromo-9,9-dimethylfluorene used in the synthesis of Scheme 3 it was synthesized in the same manner to give 17.3 g (26.1%) of 6-a.

6-2. Synthesis of 6-b

<6-b> was synthesized according to Scheme 22 below.

[Reaction Scheme 22]

                                               <6-b>

Except for using <6-a> instead of <1-c> used in the synthesis of Scheme 4 it was synthesized in the same manner to give 8.8 g (42.7%) of 6-b.

6-3. Synthesis of Formula 10

Formula 10 was synthesized according to Scheme 23 below.

[Reaction Scheme 23]

                                                  <Formula 10>

Synthesis was carried out in the same manner, except that <6-b> was used instead of <1-d> of Scheme 5 to obtain 1.4 g (16.5%) of Chemical Formula 10.

MS (MALDI-TOF): m / z = 606.23 [M] ⁺

Elemental Analysis (EA): Theoretical-C. 95.02%; H. 4.98%

                         Found-C. 94.99%; H. 5.01%

1 H NMR (CDCl ₃ ): δ 8.81 (d, 1H, Ar- H ), δ 8.34-8.28 (m, 4H, Ar- H ), δ 8.22 (s, 2H, Ar- H ), δ 7.94 ~ 7.76 ( m, 14H, Ar- H ), δ 7.54-7.21 (m, 9H, Ar- H )

Synthetic example  7. Synthesis of Chemical Formula 144

7-1. Synthesis of 7-a

&Lt; 7-a > was synthesized by the following Reaction Scheme 24.

Scheme 24

                                                            <7-a>

25.3 g (42.5%) of <7-a> was synthesized in the same manner except that 9-bromo phenanthrene was used instead of 2-bromo-9,9-dimethylfluorene used in the synthesis of Scheme 3. Got it.

7-2. Synthesis of 7-b

<7-b> was synthesized by the following Reaction Scheme 25.

[Reaction Scheme 25]

                                                           <7-b>

Except for using <7-a> instead of <1-c> used in the synthesis of Scheme 4 it was synthesized in the same manner to give 12.3 g (41.7%) of 7-b.

7-3. Synthesis of 7-c

<7-c> was synthesized by the following Reaction Formula 26.

[Reaction Scheme 26]

                                                  <7-c>

In a 250 ml round bottom flask, add <7-b> under nitrogen flow and 120 ml of dichloromethane. After the temperature of the reaction is lowered to -78 degrees, 34 ml (0.034 mol) of 1.0 mole dichloromethane of iodo monochloride are slowly added dropwise.

Stir for 4 hours and complete the reaction. The organic layer was separated using dichloromethane and water, the filtrate was concentrated, separated by column chromatography using hexane and methylene chloride as a developing solvent, recrystallized from hexane and dried to give 11.5 g (79.3%) of <7-c>. )

7-3. Synthesis of Chemical Formula 143

Formula 144 was synthesized according to Scheme 27 below.

[Reaction Scheme 27]

                                                  <Formula 144>

<7-c> in a 500 ml round bottom flask, 3.5 g (0.021 mol) diphenyl amine, Pd (OAc) ₂ , 0.062 g (0.00028 mol), BINAP 0.17 g (0.00038 mol), sodium tert-butoxide 3.94 g (0.041 mol) is added. Add 300 ml of toluene and reflux for 12 hours.

Filtered with hot toluene, concentrated the filtrate was separated by column chromatography using hexane and methylene chloride as a developing solvent, and recrystallized with hexane to dry solid to give 5.3 g (43.3%) of the general formula (144).

MS (MALDI-TOF): m / z = 873.4 [M] ⁺

Elemental Analysis (EA): Theoretical-C. 93.44%; H. 4.96%; N 1.60%

                         Found-C. 93.42%; H. 5.01%; N 1.57%

1 H NMR (CDCl ₃ ): δ 8.90 (d, 1H, Ar- H ), δ 8.24 (s, 2H, Ar- H ), δ 8.04-7.82 (m, 20H, Ar- H ), δ 7.64-7.21 ( m, 16H, Ar- H ), δ 7.19 ~ 7.08 (m, 4H, Ar- H )

Synthetic example  8. Synthesis of Chemical Formula 231

8-1. Synthesis of 8-a

&Lt; 8-a > was synthesized according to Reaction Scheme 28 below.

[Reaction Scheme 28]

                                                            <8-a>

In a 2000 ml round bottom flask, 100 g (0.27 mol) of 2,6-dibromo anthraquinone, 28.32 g (0.23 mol) of phenyl boronic acid, 6.31 g (0.0055 mol) of Pd (PPh ₃ ) ₄ , 75.52 g of potassium carbonate ( 0.55 mol). Add 500 ml of toluene, 500 ml of 1,4-dioxane and 200 ml of water and reflux for 12 hours. The reactant is cooled and the organic layer is separated using ethyl ether and water, concentrated under reduced pressure and dried. Hexane and methylene chloride were used as a developing solvent, and the residue was separated by column chromatography, and recrystallized with hexane to dry the solid to give 50.2 g (51.0%) of <8-a>.

8-2. Synthesis of 8-b

<8-b> was synthesized by the following Reaction Scheme 29.

[Reaction Scheme 29]

                                                        <8-b>

Synthesis was carried out in the same manner, except that 3-bromo phenyl-1-naphthalene was used instead of 2-bromo-9,9-dimethylfluorene, which was used in the Scheme 3, and 51.0 g (49.0) of <8-b> was obtained. %) Obtained.

8-3. Synthesis of 8-c

<8-c> was synthesized by the following Scheme 30.

Scheme 30

                                                            <8-c>

Except for using <8-b> instead of <1-c> used in the synthesis of Scheme 4 it was synthesized in the same manner to give 31.2 g (53.6%) of 8-b.

8-4. Synthesis of 8-d

<8-d> was synthesized according to Scheme 31 below.

Scheme 31

                                                <8-d>

Except for using <8-c> instead of <7-b> used in the synthesis of Scheme 26 it was synthesized in the same manner to give 12.8 g (35.9%) of 8-d.

8-5. Synthesis of Chemical Formula 231

Formula 231 was synthesized according to Scheme 32 below.

Scheme 32

                                                  <Formula 231>

In a 250 ml round-bottom flask, 2.92 g (0.017 mol) of <8-d> and 2-naphthyl boronic acid from reaction 31, 0.64 g (0.005 mol) of Pd (pph ₃ ) ₄ and 5.52 g (0.040 mol) of potassium carbonate ), Add 60 ml of toluene, 60 ml of dioxane, 40 ml of water, and reflux for 12 hours. At the end of the reaction the reaction is depressurized to give a solid. The organic layer was separated using ethyl ether and water, concentrated under reduced pressure, hexane and methylene chloride were used as a developing solvent, separated by column chromatography, and the solid was dried to give 2.6 g (66.6%) of Chemical Formula 231.

MS (MALDI-TOF): m / z = 884.3 [M] ⁺

Elemental Analysis (EA): Theoretical-C. 94.99%; H. 5.01%

                         Found-C. 94.97%; H. 5.03%

1 H NMR (CDCl ₃ ): δ 8.78 (d, 1H, Ar- H ), δ 8.40 to 8.34 (m, 3H, Ar- H ), δ 8.22 (s, 2H, Ar- H ), δ 8.1 to 7.7 ( m, 14H, Ar- H ), δ 7.6 to 7.2 (m, 24H, Ar- H )

Example

Fabrication of Organic Light Emitting Diode

The light emitting area of the ITO glass was patterned to have a size of 2 mm x 2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure is 1x10 ^-6 torr and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), the compound 10, 24, 28, 29, 83, 144 according to the present invention , 231 and 330 + RD (1.0%) (400 mW), Alq3 (300 mW), LiF (5 mW), Al (1,000 mW) were formed in this order and measured at 0.4 mA. The structure of the RD is as follows.

[RD]

      DCJTB

Comparative example

An organic light emitting diode device for a comparative example was manufactured in the same manner except for using rubrene, a compound 500, instead of the compound prepared by the invention in the device structure of the above embodiment. The structure of the rubrene and the compound 500 is as follows.

             [rubrene] [Compound 500]

division Chemical formula Dopant Doping
density% V EL Eff.
(cd / A) CIEx CIEy Example 1 28 RD 1.0% 3.8 6.33 0.63 0.36 Example 2 24 4.3 6.33 0.65 0.35 Example 3 83 4.1 7.78 0.63 0.36 Example 4 330 3.9 10.01 0.64 0.36 Example 5 29 3.7 8.01 0.64 0.36 Example 6 10 3.8 11.2 0.65 0.36 Example 7 144 4.1 12.5 0.63 0.35 Example 8 231 3.9 11.8 0.65 0.36 Comparative Example 1 rubrene 4.5 2.98 0.65 0.34 Comparative Example 2 Compound 500 4.3 5.76 0.64 0.36

As shown in Table 1, the compound according to the exemplary embodiment of the present invention exhibits a low driving voltage and excellent luminous efficiency as compared with rubrene, which is commonly used as a host material, and the compound 500.

Although the present invention has been described with reference to the synthesis examples and examples, this is merely illustrative, and those skilled in the art to which the present invention pertains various modifications and equivalent other embodiments. Will understand. Accordingly, the true scope of the present invention should be determined by the technical idea of the appended claims.

Claims (20)

A compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
R ₁ to R ₁₄ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted group having 2 to 60 carbon atoms Alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or substituted with 5 to 60 carbon atoms, or Unsubstituted arylthio groups, substituted or unsubstituted aryl groups having 5 to 60 carbon atoms, amino groups substituted with aryl groups having 5 to 60 carbon atoms or heteroaryl groups having 3 to 60 carbon atoms, substituted or unsubstituted with 3 to 60 carbon atoms A heteroaryl group, a substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group. The method of claim 1,
In Formula 1, R ₁ to R ₁₄ are each independently hydrogen, deuterium, cyano group, halogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, A compound which is an amino group substituted with a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, an aryl group having 5 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms . The method of claim 1,
In Formula 1, R ₁ to R ₁₄ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a compound represented by the following Formula 2a to 2g:

Among the above formulas (2a) to (2g)
Q ₁ and Q ₂ are linking groups represented by -C (R ₂₀ ) (R ₂₁ )-, -N (R ₂₀ )-, -S- or -O-;
Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =;
Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Silyl group, wherein adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond;
Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
p is an integer from 1 to 12;
r is an integer from 0 to 5;
* Represents a bond. The method of claim 1,
In Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium. The method of claim 1,
In Formula 1, R ₂ and R ₁₁ are the same substituent. The method of claim 1,
R ₁ to R ₁₄ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and 6 to 30 carbon atoms A substituted or unsubstituted condensed polycyclic group of, or a compound of Formulas 3a to 3f:

In Formulas 3a to 3f,
Z ₁ is a hydrogen atom, deuterium, or a substituted or unsubstituted aryl group having 5 to 20 carbon atoms;
p is an integer from 1 to 5;
* Represents a bond. The method of claim 1,
In Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ is independently of each other hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a compound represented by Formula 2a to 2g:

Among the above formulas (2a) to (2g)
Q ₁ and Q ₂ are linking groups represented by -C (R ₂₀ ) (R ₂₁ )-, -N (R ₂₀ )-, -S- or -O-;
Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =;
Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Silyl group, wherein adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond;
Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
p is an integer from 1 to 12;
r is an integer from 0 to 5;
* Represents a bond. The method of claim 1,
In Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ is independently of each other hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a compound of Formulas 3a to 3f:

In Formulas 3a to 3f,
Z ₁ is a hydrogen atom, deuterium or a substituted or unsubstituted aryl group having 5 to 20 carbon atoms;
p is an integer from 1 to 5;
* Represents a bond. The method of claim 1,
In Formula 1, R ₁ , R ₃ , R ₄ , R ₇ , R ₁₀ , R ₁₂ to R ₁₄ are each independently hydrogen or deuterium, R ₂ , R ₅ , R ₆ , R ₈ , R ₉ and R ₁₁ is independently of each other hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a compound of Formulas 2a to 2g, wherein R ₂ and R ₁₁ are the same substituent:

Among the above formulas (2a) to (2g)
Q ₁ and Q ₂ are linking groups represented by -C (R ₂₀ ) (R ₂₁ )-, -N (R ₂₀ )-, -S- or -O-;
Y ₁ , Y ₂ and Y ₃ are independently of each other a linking group represented by -N = or -C (R ₂₂ ) =;
Z ₁ , Z ₂ , Ar ₁₂ , Ar ₁₃ , R ₂₀ , R ₂₁ , and R ₂₂ are each independently a hydrogen atom, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted 5 to 20 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted condensed polycyclic group having 6 to 20 carbon atoms, halogen atom, cyano group, nitro group, hydroxy group, carboxyl group or substituted Silyl group, wherein adjacent Ar ₁₂ and Ar ₁₃ or adjacent R ₂₀ and R ₂₁ may be fused to each other or connected with a single bond;
Ar ₁₁ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 5 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
p is an integer from 1 to 12;
r is an integer from 0 to 5;
* Represents a bond. The method of claim 1,
Compound wherein the compound of Formula 1 is one of the following compounds:

A first electrode;
A second electrode; And
An organic layer interposed between the first electrode and the second electrode,
The organic light emitting device of claim 1, wherein the organic layer comprises a compound represented by Chemical Formula 1. The method of claim 11,
The organic light emitting device is a functional layer having a hole injection layer, a hole transport layer, a hole injection and a hole transport function at the same time, an electron injection layer, an electron transport layer, or a functional layer having an electron injection and electron transport function at the same time. The method of claim 11,
And the organic light emitting device comprises an electron transporting layer including an electron transporting organic material and a metal-containing material. The method of claim 11,
An organic light emitting device in which the organic layer is a light emitting layer and the compound represented by Chemical Formula 1 is used as a fluorescent or phosphorescent host. The method of claim 11,
The organic light emitting device includes a light emitting layer, a hole transport layer and an electron transport layer,
The emission layer further comprises an anthracene compound, an arylamine compound or a styryl compound. The method of claim 11,
The organic light emitting device includes a light emitting layer, a hole transport layer and an electron transport layer,
The organic light emitting device of any one of the red layer, green layer, blue layer or white layer of the light emitting layer further comprises a phosphorescent compound. The method of claim 11,
The organic light emitting device of the organic layer is a red light emitting layer. The method of claim 11,
The organic layer is a red light emitting layer,
An organic light emitting device in which the compound of Formula 1 is used as a red host. The method of claim 11,
An organic light emitting device in which the organic layer is formed by a wet process using the compound of claim 1. The organic light-emitting device of claim 11,
And a first electrode of the organic light emitting element is electrically connected to a source electrode or a drain electrode of the thin film transistor.

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