KR20210128617A - Organic Light Emitting Material and Organic Light Emitting Diode Having The Same - Google Patents

Abstract

The present invention relates to a compound derivative used in an organic electroluminescent device and the organic electroluminescent device using the same. More particularly, the present invention relates to an aromatic compound containing an indolocarbazolyl group and a spirobifluorenyl group, and when the compound is used as a light emitting material in an organic layer of the organic electroluminescent device, an effect of exhibiting high luminous efficiency even with a low driving voltage can be provided.

Description

An organic electroluminescent composition and an organic electroluminescent device comprising the same

The present invention relates to an organic electroluminescent device, and more particularly, to an aromatic compound containing an indolocarbazolyl group and a spirobifluorenyl group used as a light emitting material for an organic electroluminescent device, and more particularly, to an indole group based on an amine group An aromatic compound including a locarbazolyl group and a spirobifluorenyl group, an organic electroluminescent composition including the same, and an organic electroluminescent device including the same.

The organic electroluminescent device, which has various advantages such as low voltage driving, self-luminescence, light weight and thinness, wide viewing angle, and fast response speed, is one of the next-generation flat panel displays and is the most actively researched field in recent years.

The organic electroluminescent device is generally composed of a structure in which an organic thin film is disposed between an anode and a cathode. The organic layer adjacent to the anode contains a hole transport material and has a function of mainly transporting only holes to the light emitting layer in the organic electroluminescent device. Similarly, the organic layer adjacent to the cathode contains an electron transport material and has a function of mainly transporting only electrons in the organic electroluminescent device device. After the holes and electrons injected from the anode and the cathode recombine in the light emitting layer, light is emitted from the excited state to the ground state.

The organic film of the organic electroluminescent device is not a simple structure, but a multilayer structure including a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer composed of a host and a dopant. It was possible to improve the performance of the organic electroluminescent device.

In order to improve the light emitting characteristics such as driving voltage and luminous efficiency of the organic electroluminescent device and to extend the lifespan of the device for a long time, it is necessary to continuously research and develop organic thin film materials used in the organic electroluminescent device.

In this regard, the present inventors have disclosed Korean Patent No. 10-1555816 (published on September 25, 2015, title of invention: organic electroluminescent composition and organic electroluminescent device comprising the same), Korean Patent No. 10-1529878 ( Announcement date: June 18, 2015, Title of invention: Organic electroluminescent composition and organic electroluminescent device comprising same), Republic of Korea Patent No. 10-1627211 (Announcement date: June 13, 2016, Title of invention: Containing aromatic compound Through an organic electroluminescent composition and an organic electroluminescent device including the same), various aromatic amine derivative compounds were invented. The compounds described herein have high luminance and luminous efficiency.

However, there is still a need for a new compound having a higher luminous efficiency while operating at a lower driving voltage than before.

Republic of Korea Patent Registration No. 10-1555816 (Announcement date: 2015.09.25.) Republic of Korea Patent Registration No. 10-1529878 (Announcement Date: 2015.06.18.) Republic of Korea Patent Registration No. 10-1627211 (Announcement date: 2016.06.13.)

An object of the present invention for solving the above problems is to provide a compound having high luminous efficiency even at a low driving voltage when used as a light emitting material in an organic layer of an organic electroluminescent device.

Another object of the present invention is to provide a compound having excellent thermal stability, an organic electroluminescent composition comprising the same, and an organic electroluminescent device.

Another object of the present invention is to provide a novel compound capable of improving the luminous efficiency of an organic electroluminescent device and increasing the lifespan of the device, and a method for preparing the same.

Another object of the present invention is to provide an organic electroluminescent device having high luminous efficiency and extended lifetime.

The present invention is a compound represented by the following formula (I).

[Formula I]

In Formula I, L ₁ and L ₂ are each a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted A cyclic alkenylene group, or a linker,

R ₁ is a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted an alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted silyl group, or a cyano group,

R ₂ to R ₈ are each independently a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylox a group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, or a cyano group,

a is an integer from 0 to 2, b to f are each an integer from 0 to 4, g is an integer from 0 to 3, and when a to g is 2 or more, the substituents in parentheses are the same or different.

The details of other embodiments are included in the detailed description and drawings.

When the compound according to the present invention is used as a light emitting material in an organic layer of an organic electroluminescent device, high luminous efficiency can be obtained even with a low driving voltage.

In addition, the compound according to the present invention has excellent thermal stability because it has a high glass transition temperature and thermal decomposition temperature. It exhibited excellent luminous properties in terms of luminance and luminous efficiency.

In addition, when an organic electroluminescent device is manufactured using the compound according to the present invention, the problem of low luminance and luminous efficiency, which are the biggest disadvantages of the existing organic electroluminescent device, can be simultaneously solved, and the glass transition temperature is also high. Therefore, since the organic electroluminescent device has excellent thermal stability, a high-performance organic electroluminescent device can be manufactured, and it can greatly contribute to the commercialization of the organic electroluminescent device requiring high efficiency, high luminance and long life.

1 is a view showing a multilayer structure of an organic electroluminescent device manufactured using an aromatic amine derivative according to an embodiment of the present invention.
2 is a UV/Vis of Compound 2 according to an embodiment of the present invention. Absorbance, fluorescence PL, and low-temperature PL spectral graphs.
3 is a UV/Vis of compound 33 according to an embodiment of the present invention. Absorbance, fluorescence PL, and low-temperature PL spectral graphs.
4 is a UV/Vis of Compound 43 according to an embodiment of the present invention. Absorbance, fluorescence PL, and low-temperature PL spectral graphs.
5 is a differential scanning calorimetry (DSC) curve graph of Compound 2 according to an embodiment of the present invention.
6 is a differential scanning calorimetry (DSC) curve graph of Compound 33 according to an embodiment of the present invention.
7 is a differential scanning calorimetry (DSC) curve graph of Compound 43 according to an embodiment of the present invention.

Since the present invention can apply various transformations and can have various embodiments, specific embodiments are illustrated in the drawings and described in detail in the detailed description. However, this is not intended to limit the present invention to specific embodiments, and it should be understood to include all modifications, equivalents and substitutes included in the spirit and scope of the present invention. In describing the present invention, if it is determined that a detailed description of a related known technology may obscure the gist of the present invention, the detailed description thereof will be omitted.

The terms used in the present application are only used to describe specific embodiments, and are not intended to limit the present invention. The singular expression includes the plural expression unless the context clearly dictates otherwise. In the present application, terms such as “comprise” or “have” are intended to designate that a feature, number, step, operation, component, part, or combination thereof described in the specification exists, but one or more other features It should be understood that this does not preclude the existence or addition of numbers, steps, operations, components, parts, or combinations thereof.

Terms such as first, second, etc. may be used to describe various elements, but the elements should not be limited by the terms. The above terms are used only for the purpose of distinguishing one component from another.

The present invention is a compound represented by the following formula (I). Specifically, the present invention is an aromatic amine derivative useful for use as an organic electroluminescent material in an organic electroluminescent device, particularly an aromatic compound containing an indolocarbazolyl group having an amine substituent and a spirobifluorenyl group. Since the compound according to the present invention has a high glass transition temperature and excellent hole injection and transport ability, when an organic electroluminescent device is manufactured using the compound, the luminous efficiency can be further increased even with a low driving voltage, thereby prolonging the life of the device. can increase

[Formula I]

In Formula I, L ₁ and L ₂ are each a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted A cyclic alkenylene group, or a linker,

R ₁ is a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted an alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted silyl group, or a cyano group,

R ₂ to R ₈ are each independently a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylox a group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, or a cyano group,

a is an integer from 0 to 2, b to f are each an integer from 0 to 4, g is an integer from 0 to 3, and when a to g is 2 or more, the substituents in parentheses are the same or different.

In the above formula (I), substituted or unsubstituted means substituted by any functional group known in the art or unsubstituted by any functional group, wherein the functional group refers to a group of organic compounds having common chemical properties. A common group of atoms responsible for its properties in a compound or its mode of association.

In Formula I, L ₁ and L ₂ may each be a substituted or unsubstituted arylene group, a heteroarylene group, a heterocyclic group, an alkylene group, an alkenylene group, or a linking group. That is, the present invention is characterized in that it includes a central structure in which an indolocarbazolyl group and a spirobifluorenyl group are connected to both sides around an amine group.

The arylene group may be areenediyl groups in which one hydrogen atom is removed from carbon atoms at both ends of arenes, and the alkylene group is located at both ends of an alkane. A form in which one hydrogen atom is removed from a carbon atom (-CnH2n-) is possible (for example, propylene), and the alkenylene group is a form in which one hydrogen atom is missing from carbon atoms at both ends of the alkene can

The present inventors have studied for a long period of time on various aromatic amine derivative compounds exhibiting excellent luminescent properties, and as a result, the central structure of the compound is an amine group, including an indolocarbazolyl group and a spirobifluorenyl group on both sides. After confirming that the compound exhibits more excellent luminescent properties than before, the present invention was completed.

As can be seen in Examples to be described later, when the compound according to the present invention is used as a light emitting material in an organic layer of an organic electroluminescent device, it is possible to have high luminous efficiency even with a lower driving voltage than other conventional compounds.

The compound according to the present invention is structurally different from other compounds in the prior art, and has excellent thermal stability because it has a high glass transition temperature and a thermal decomposition temperature.

Therefore, the compound according to the present invention may be used as a light emitting material of an organic light emitting diode (Organic Light Emitting Diode). When an organic electroluminescent device is manufactured using the compound according to the present invention, the problems of low luminance and luminous efficiency, which are the biggest disadvantages of the existing organic electroluminescent device, can be simultaneously solved, and the organic electroluminescent device has a high glass transition temperature. Since the electroluminescent device has excellent thermal stability, a high-performance organic electroluminescent device can be manufactured, and it can greatly contribute to the commercialization of an organic electroluminescent device requiring high efficiency, high luminance and long life.

In one embodiment of the present invention, the formula (I) may be a compound characterized in that it is represented by the following formula (II) or formula (III).

[Formula II]

[Formula III]

In Formulas II and III, L ₂ , R ₁ to R ₈ , and a to g are as defined in Formula I, and L3 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group .

That is, in Formula I, L ₁ is more preferably a linking group, an arylene group, or a heterocyclic group. In other words, the present invention is a compound formed by connecting an amine substituent including an indolocarbazolyl group and a spirobifluorenyl group to each other, wherein the indolocarbazolyl group (and spirobifluorenyl group) is directly connected to the amine group It is characterized in that the compound has a central structure consisting of or connected by an aromatic ring, and the aromatic ring may be an arylene group, a heteroarylene group, a heterocyclic group, an alkylene group, or an alkenylene group, among others, an arylene group, or It is more preferably a heterocyclic group.

, In the case where the L ₁ in the formula (I) linking group, or L ₃ is an aryl group or a heterocyclic group of the above formula (I) of L ₁ or the formula (III) As can be seen from the Examples described later, even more superior light emission than a conventional characteristics were shown.

In addition, as an embodiment of the present invention, the formula (I) may be a compound characterized in that it is represented by the following formula (IV) or (V).

[Formula IV]

[Formula V]

In Formula IV and Formula V, L ₁ , L ₂ , R ₁ to R ₈ , and a to g are as defined in Formula I.

As can be seen in Examples to be described later, when R ₂ of Formula I is an aryl group (or biphenyl), when the compound is used in a hole transport layer or an electron blocking layer, the luminous efficiency and lifespan of the device are reduced. further improved.

In addition, as an embodiment of the present invention, the formula (I) may be a compound characterized in that it is represented by the following formula (VI) or formula (VII).

[Formula VI]

[Formula VII]

In Formulas VI and VII, L ₁ , R ₁ to R ₈ , and a to g are as defined in Formula I above, and L ₄ is a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group .

That is, in Formula I, L ₂ is more preferably a linking group as shown in Formula VI, an arylene group or a heterocyclic group as shown in Formula VII, or _{even more preferably L 2} is a linking group as shown in Formula VI.

That is, in Formula I, L ₂ is more preferably a linking group, an arylene group, or a heterocyclic group. In other words, the present invention relates to a compound in which an indolocarbazolyl group and an amine substituent including a spirobifluorenyl group are connected to each other, and the spirobifluorenyl group is directly connected to an amine substituent or connected by an aromatic ring. Characterized in a compound having a central structure consisting of, the aromatic ring may be an arylene group, a heteroarylene group, a heterocyclic group, an alkylene group, or an alkenylene group. It is even more preferable that it is a linking group.

As can be seen in Examples to be described later, when the compound in which L ₂ of Formula I is a linking group is used in the hole transport layer or the electron blocking layer, the luminous efficiency and lifespan of the device are further improved.

As described above, the formula I of the present invention may be characterized in that at least one selected from the group consisting of the following compounds. The present invention is an aromatic amine derivative having the structure of Formula I, and specific examples of enabling an organic electroluminescent device having particularly high luminous efficiency and long life include at least one selected from the following structural formula. However, the present invention is not limited thereto.

The present invention may be an aromatic derivative including an indolocarbazolyl group and a spirobifluorenyl group that can be used as a light emitting material for an organic electroluminescent device as described above, or an organic light emitting composition or organic light emitting material including the same. That is, the present invention may be an organic electroluminescent composition comprising the above compound and used as a light emitting material of an organic light emitting diode. In addition, the present invention may be an organic electroluminescent composition comprising the above compound, characterized in that it is used in a hole transport layer or an electron blocking layer of an organic light emitting diode (Organic Light Emitting Diode).

When the derivative, composition or material according to the present invention is used in an organic electroluminescent device, excellent luminous efficiency can be obtained, and the glass transition temperature of the aromatic derivative compound containing the indolocarbazolyl group and the spirobifluorenyl group is high. A device having excellent durability can be manufactured. Here, the aromatic derivative compound containing the indolocarbazolyl group and the spirobifluorenyl group is a material that can be used as a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer or a light emitting layer or a dopant, preferably For example, it is most effective when used as a hole transport layer or an electron blocking layer.

The organic light emitting composition according to the present invention and an organic electroluminescent device including the same can be applied to not only organic light emitting diodes, but also organic field-effect transistors, organic thin film transistors, organic laser diodes, organic solar cells, organic light emitting electrochemical cells and organic integrated circuits. It can also be used in the field.

In addition, the aromatic amine derivatives according to the present invention may be purified by recrystallization and sublimation due to the characteristics of the organic electroluminescent device requiring high purity.

In addition, another embodiment of the present invention is an organic electroluminescent device comprising at least one organic layer comprising the above-described organic electroluminescent composition. Here, the organic electroluminescent device includes an organic light emitting diode, an organic field-effect transistor, an organic thin film transistor, an organic laser diode, an organic solar cell, an organic light emitting electrochemical cell or an organic integrated circuit, and the present invention relates to the organic light emitting diode. It is clear to those of ordinary skill in the art that it can be variously applied to diodes and the like.

Hereinafter, the present invention may be better understood by the following examples, which are for illustrative purposes of the present invention, and are not intended to limit the scope of protection defined by the appended claims .

[Example 1] Preparation of compound 1

1-1. Preparation of compound 1-1

In a 500-mL, 3-neck round-bottom flask, 9.7 g (0.058 mol) of the compound carbazole was added under a nitrogen atmosphere and diluted with 200 mL of dimethyl sulfoxide. To this dilution, 15 g of 1,2-dibromobenzene, 3.7 g of copper powder, and 12 g of potassium carbonate were added, followed by stirring at room temperature for 30 minutes. The reaction solution was heated to reflux for 20 hours. The reaction solution was cooled to room temperature and extracted using dichloromethane and distilled water. After drying the extract, it was concentrated under reduced pressure to obtain 10.3 g of Compound 1-1 (yield 55%).

1-2. Preparation of compound 1-2

In a 3000-mL, 4-neck round-bottom flask, to 22 g (0.069 mol) of the compound 1-1 prepared in Example 1-1, 1.6 g of palladium acetate (II), 3.6 g of triphenylphosphine, 43 g of potassium carbonate Tetrabutyl 11 g of ammonium bromide and 2200 mL of dimethylacetamide were added. After the reaction solution was stirred at 150° C. for 20 hours, dimethylacetamide was concentrated under reduced pressure. This concentrate was diluted with dichloromethane and extracted using dichloromethane and distilled water. After drying the extract, the crude product obtained by concentration under reduced pressure was separated by column to obtain 7.8 g of Compound 1-2 (yield 47%).

1-3. Preparation of compound 1-3

6.5 g (0.027 mol) of the compound 1-2 prepared in Example 1-2 was added to a 500-mL, 3-neck round-bottom flask, and diluted with 162 mL of chloroform. After cooling the diluted solution to 0° C., 4.8 g of N -bromosuccinimide (NBS) was slowly added thereto, followed by stirring at room temperature for 12 hours. After adding 160 mL of distilled water to the reaction solution, the mixture was stirred for 30 minutes, and then the organic layer was separated. The separated organic layer was dried, concentrated, recrystallized from acetonitrile and ethyl acetate, and dried under vacuum to obtain 5.4 g (yield 63%) of compound 1-3.

1-4. Preparation of compound 1-4

In a 500-mL, 3-neck round-bottom flask, 5.4 g (0.058 mol) of the compound aniline was added under a nitrogen atmosphere and diluted with 250 mL of toluene. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 1 hour, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 19.4 g of Compound 1-4 (yield 82%).

1-5. Preparation of compound 1

In a 250-mL, 3-neck round-bottom flask, to 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3, 9.9 g of the compound 1-4 prepared in Example 1-4, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 80 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 13.5 g of Compound 1 (yield 91%).

[Example 2] Preparation of compound 2

2-1. Preparation of compound 2-1

Compound [1,1`-biphenyl]-4-amine 9.8 g (0.058 mol) was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 250 mL of toluene. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 1 hour, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 23.6 g of Compound 2-1 (yield 84%).

2-2. Preparation of compound 2

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 11.7 g of Compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.8 g of Compound 2 (yield 89%).

[Example 3] Preparation of compound 3

3-1. Preparation of compound 3-1

Compound [1,1`-biphenyl]-3-amine 9.8 g (0.058 mol) was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and diluted with 250 mL of toluene. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 1 hour, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to obtain 21.9 g of Compound 3-1 (yield 78%).

3-2. Preparation of compound 3

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 11.7 g of Compound 3-1 prepared in Example 3-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 13.6 g of compound 3 (yield 82%).

[Example 4] Preparation of compound 4

4-1. Preparation of compound 4-1

Compound [1,1`-biphenyl]-2-amine 9.8 g (0.058 mol) was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 250 mL of toluene. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 1 hour, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 23.0 g of Compound 4-1 (yield 82%).

4-2. Preparation of compound 4

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 11.7 g of Compound 4-1 prepared in Example 4-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.1 g of compound 4 (yield 85%).

[Example 5] Preparation of compound 5

5-1. Preparation of compound 5-1

And it poured fluorene-2-amine 12.1 g (0.058 mol), diluted with toluene 300 mL - 500-mL, 3 gu a nitrogen atmosphere a round bottom flask was added the compound 9,9-dimethyl -9 H. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 3 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 22.5 g of Compound 5-1 (yield 74%).

5-2. Preparation of compound 5

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 12.6 g of Compound 5-1 prepared in Example 5-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.2 g of Compound 5 (yield 81%).

[Example 6] Preparation of compound 6

6-1. Preparation of compound 6-1

10.6 g (0.058 mol) of the compound dibenzo [b, d] furan-4-amine was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 300 mL of toluene. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 17.9 g of Compound 6-1 (yield 62%).

6-2. Preparation of compound 6

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 12.0 g of Compound 6-1 prepared in Example 6-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 12.5 g of compound 6 (yield 74%).

[Example 7] Preparation of compound 7

7-1. Preparation of compound 7-1

15.0 g (0.058 mol) of the compound 6-phenyldibenzo[b,d] furan-4-amine was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and the mixture was diluted with 300 mL of toluene. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 20.0 g of Compound 7-1 (yield 60%).

7-2. Preparation of compound 7

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 13.9 g of Compound 7-1 prepared in Example 7-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 13.3 g of Compound 7 (yield 71%).

[Example 8] Preparation of compound 8

8-1. Preparation of compound 8-1

10.6 g (0.058 mol) of the compound dibenzo[b,d] furan-3-amine was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and the mixture was diluted with 300 mL of toluene. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 19.6 g of Compound 8-1 (yield 68%).

8-2. Preparation of compound 8

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 12.0 g of Compound 8-1 prepared in Example 8-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 12.9 g of Compound 8 (yield 76%).

[Example 9] Preparation of compound 9

9-1. Preparation of compound 9-1

In a 1000-mL, 4-neck round-bottom flask, 13.3 g (0.054 mol) of 4-bromodibenzo[b,d ]furan was added and diluted with 350 mL of tetrahydrofuran. To this dilution, 9.4 g of (4-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 6 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 12.3 g of compound 9-1 (yield 82%).

9-2. Preparation of compound 9-2

16.2 g (0.058 mol) of the compound 9-1 prepared in Example 9-1 was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 300 mL of toluene. In this dilution, 19.2 g of 9,9'-spirobi[fluorene]-2-amine, 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and sodium 7.2 g of t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 25.6 g of compound 9-2 (yield 77%).

9-3. Preparation of compound 9

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 13.9 g of compound 9-2 prepared in Example 9-2, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.0 g of compound 9 (yield 80%).

[Example 10] Preparation of compound 10

10-1. Preparation of compound 10-1

11.6 g (0.058 mol) of the compound dibenzo [b, d] thiophen-4-amine was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and the mixture was diluted with 300 mL of toluene. To this dilution, 22.9 g of 2-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 19.1 g of Compound 10-1 (yield 64%).

10-2. Preparation of compound 10

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 11.8 g of Compound 10-1 prepared in Example 10-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 12.3 g of Compound 10 (yield 71%).

[Example 11] Preparation of compound 11

11-1. Preparation of compound 11-1

16.2 g (0.058 mol) of the compound 9-1 prepared in Example 9-1 was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 300 mL of toluene. In this dilution, 19.2 g of 9,9'-spirobi[fluorene]-4-amine, 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and sodium 7.2 g of t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 24.6 g of Compound 11-1 (yield 74%).

11-2. Preparation of compound 11

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 13.9 g of Compound 11-1 prepared in Example 11-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.1 g of Compound 11 (yield 75%).

[Example 12] Preparation of compound 12

12-1. Preparation of compound 12-1

10.6 g (0.058 mol) of the compound 4-bromobenzonitrile was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and the mixture was diluted with 300 mL of toluene. In this dilution, 19.2 g of 9,9'-spirobi[fluorene]-2-amine, 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and sodium 7.2 g of t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.5 g of Compound 12-1 (yield 58%).

12-2. Preparation of compound 12

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 9.9 g of Compound 12-1 prepared in Example 12-1, Palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 11.1 g of Compound 12 (yield 72%).

[Example 13] Preparation of compound 13

13-1. Preparation of compound 13-1

1000-mL, 4-bromo-9,9-dimethyl-2-gu -9 H To a round bottom flask was added the fluorene 14.7 g (0.054 mol), diluted with 350 mL of tetrahydrofuran. To this dilution, 9.4 g of (4-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 6 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum-dried to obtain 14.0 g of compound 13-1 (yield 85%).

13-2. Preparation of compound 13-2

17.7 g (0.058 mol) of the compound 13-1 prepared in Example 13-1 was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 300 mL of toluene. In this dilution, 19.2 g of 9,9'-spirobi[fluorene]-2-amine, 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and sodium 7.2 g of t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 29.9 g of compound 13-2 (yield 86%).

13-3. Preparation of compound 13

In a 250-mL, 3-neck round-bottom flask, to 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3, 13.8 g of the compound 13-2 prepared in Example 13-2, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 16.2 g of compound 13 (yield 84%).

[Example 14] Preparation of compound 14

14-1. Preparation of compound 14-1

In a 1000-mL, 4-neck round-bottom flask, 21.3 g (0.054 mol) of 2-bromo-9,9'-spiroby[fluorene] was added and diluted with 400 mL of tetrahydrofuran. To this dilution, 9.4 g of (4-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 6 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 18.7 g of compound 14-1 (yield 81%).

14-2. Preparation of compound 14-2

24.8 g (0.058 mol) of the compound 14-1 prepared in Example 14-1 was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 300 mL of toluene. To this dilution, 9.8 g of [1,1`-biphenyl]-4-amine, 0.27 g of tris(dibenzylideneacetone)dipalladium (0), 0.12 g of tri-(t-butyl)phosphine, and sodium t-butoxy 7.2 g of seeds were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 23.7 g of compound 14-2 (yield 73%).

14-3. Preparation of compound 14

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 12.9 g of compound 14-2 prepared in Example 14-2, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.3 g of Compound 14 (yield 78%).

[Example 15] Preparation of compound 15

15-1. Preparation of compound 15-1

Compound [1,1`-biphenyl]-4-amine 9.8 g (0.058 mol) was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 250 mL of toluene. In this dilution, 22.9 g of 4-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 1 hour, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 22.2 g of compound 15-1 (yield 79%).

15-2. Preparation of compound 15

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 11.7 g of compound 15-1 prepared in Example 15-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.1 g of compound 15 (yield 85%).

[Example 16] Preparation of compound 16

16-1. Preparation of compound 16-1

Compound [1,1`-biphenyl]-3-amine 9.8 g (0.058 mol) was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and diluted with 250 mL of toluene. In this dilution, 22.9 g of 4-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 1 hour, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 19.9 g of compound 16-1 (yield 71%).

16-2. Preparation of compound 16

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 11.7 g of compound 16-1 prepared in Example 16-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 12.8 g of Compound 16 (yield 77%).

[Example 17] Preparation of compound 17

17-1. Preparation of compound 17-1

Compound [1,1`-biphenyl]-2-amine 9.8 g (0.058 mol) was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 250 mL of toluene. In this dilution, 22.9 g of 4-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 2 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to obtain 20.5 g of compound 17-1 (yield 73%).

17-2. Preparation of compound 17

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 11.7 g of compound 17-1 prepared in Example 17-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 13.3 g of Compound 17 (yield 80%).

[Example 18] Preparation of compound 18

18-1. Preparation of compound 18-1

10.6 g (0.058 mol) of the compound dibenzo [b, d] furan-4-amine was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 300 mL of toluene. In this dilution, 22.9 g of 4-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 18.8 g of compound 18-1 (yield 65%).

18-2. Preparation of compound 18

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 12.0 g of compound 18-1 prepared in Example 18-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 12.2 g of Compound 18 (yield 72%).

[Example 19] Preparation of compound 19

19-1. Preparation of compound 19-1

15.0 g (0.058 mol) of the compound 6-phenyldibenzo[b,d] furan-4-amine was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and the mixture was diluted with 300 mL of toluene. In this dilution, 22.9 g of 4-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 18.3 g of compound 19-1 (yield 55%).

19-2. Preparation of compound 19

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 13.9 g of compound 19-1 prepared in Example 19-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 12.9 g of Compound 19 (yield 69%).

[Example 20] Preparation of compound 20

20-1. Preparation of compound 20-1

11.6 g (0.058 mol) of the compound dibenzo [b, d] thiophen-4-amine was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and the mixture was diluted with 300 mL of toluene. In this dilution, 22.9 g of 4-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 18.2 g of compound 20-1 (yield 61%).

20-2. Preparation of compound 20

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 11.8 g of Compound 20-1 prepared in Example 20-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 11.6 g of compound 20 (yield 67%).

[Example 21] Preparation of compound 21

21-1. Preparation of compound 21-1

19.7 g (0.058 mol) of the compound 4-bromo-6-phenyldibenzo[b,d] thiophene was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere, and the mixture was diluted with 300 mL of toluene. In this dilution, 19.2 g of 9,9'-spirobi[fluorene]-4-amine, 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and sodium 7.2 g of t-butoxide was added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 20.5 g of compound 21-1 (yield 60%).

21-2. Preparation of compound 21

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 13.6 g of compound 21-1 prepared in Example 21-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 12.8 g of Compound 21 (yield 67%).

[Example 22] Preparation of compound 22

22-1. Preparation of compound 22-1

Compound [1,1`-biphenyl]-2-amine 9.8 g (0.058 mol) was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 250 mL of toluene. In this dilution, 22.9 g of 1-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 5 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to obtain 16.3 g of Compound 22-1 (yield 58%).

22-2. Preparation of compound 22

In a 250-mL, 3-neck round-bottom flask, to 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3, 11.7 g of the compound 22-1 prepared in Example 22-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 11.6 g of Compound 22 (yield 70%).

[Example 23] Preparation of compound 23

23-1. Preparation of compound 23-1

And it poured fluorene-2-amine 12.1 g (0.058 mol), diluted with toluene 300 mL - 500-mL, 3 gu a nitrogen atmosphere a round bottom flask was added the compound 9,9-dimethyl -9 H. In this dilution, 22.9 g of 4-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 3 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 23.4 g of compound 23-1 (yield 77%).

23-2. Preparation of compound 23

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 12.6 g of Compound 23-1 prepared in Example 23-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 100 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 13.5 g of compound 23 (yield 77%).

[Example 24] Preparation of compound 24

24-1. Preparation of compound 24-1

In a 2000-mL, 4-neck round-bottom flask, 19.5 g (0.027 mol) of the compound 2 prepared in Example 2-2 was added and diluted with 600 mL of chloroform. After cooling the diluted solution to 0°C, 19.2 g of N -bromosuccinimide (NBS) was slowly added thereto, followed by stirring at 45°C for 15 hours. After adding 600 mL of distilled water to the reaction solution, the mixture was stirred for 30 minutes, and then the organic layer was separated. The separated organic layer was dried, concentrated, and separated by column to obtain 12.1 g of Compound 24-1 (yield 51%).

24-1. Preparation of compound 24

23.8 g (0.027 mol) of the compound 24-1 prepared in Example 24-1 was added to a 1000-mL, 4-neck round-bottom flask and diluted with 500 mL of tetrahydrofuran. To this dilution, 7.3 g of phenylboronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 7 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The obtained solid was dried in vacuo and separated by a column to obtain 19.4 g of Compound 24 (yield 82%).

[Example 25] Preparation of compound 25

25-1. Preparation of compound 25-1

And diluted with 370 mL of dimethylformamide-500-mL, 3-bromo-2-gu compound -9 H in a nitrogen atmosphere in a round bottom flask In the carbazole 24.6 g (0.100 mol) and N, N. To this dilution, 14.6 g of potassium t-butoxide was added, and after refluxing for 20 minutes, 24.4 g of 1-fluoro-2-iodobenzene was added. The reaction solution was refluxed for 8 hours, cooled to room temperature, and extracted using ethyl acetate and distilled water. The extract was dried and concentrated under reduced pressure to obtain 30.9 g of compound 25-1 (yield 69%) by column separation of the obtained crude product.

25-2. Preparation of compound 25-2

To 23.7 g (0.053 mol) of compound 25-1 prepared in Example 25-1 in a 1000-mL, 4-neck round-bottom flask, 0.12 g of palladium acetate (II), 0.22 g of tri-(t-butyl)phosphine, and carbonic acid 14.7 g of potassium and 380 mL of dimethylacetamide were added. After refluxing the reaction solution for 4 hours, dimethylacetamide was concentrated under reduced pressure. This concentrate was extracted using ethyl acetate and distilled water. The extract was dried and concentrated under reduced pressure, and the obtained crude product was separated by column to obtain 6.4 g of Compound 25-2 (yield 38%).

25-3. Preparation of compound 25

To 7.3 g (0.023 mol) of the compound 25-2 prepared in Example 25-2 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.0 g of compound 25 (yield 84%).

[Example 26] Preparation of compound 26

In a 250-mL, 3-neck round-bottom flask, to 7.3 g (0.023 mol) of the compound 25-2 prepared in Example 25-2, 11.7 g of the compound 3-1 prepared in Example 3-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.7 g of compound 26 (yield 88%).

[Example 27] Preparation of compound 27

In a 250-mL, 3-neck round-bottom flask, to 7.3 g (0.023 mol) of the compound 25-2 prepared in Example 25-2, 11.7 g of the compound 4-1 prepared in Example 4-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.0 g of Compound 27 (yield 84).

[Example 28] Preparation of compound 28

In a 250-mL, 3-neck round-bottom flask, to 7.3 g (0.023 mol) of the compound 25-2 prepared in Example 25-2, 11.7 g of the compound 15-1 prepared in Example 15-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.5 g of compound 28 (yield 87%).

[Example 29] Preparation of compound 29

In a 250-mL, 3-neck round bottom flask, to 7.3 g (0.023 mol) of the compound 25-2 prepared in Example 25-2, 11.7 g of the compound 16-1 prepared in Example 16-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 13.0 g of Compound 29 (yield 78%).

[Example 30] Preparation of compound 30

To 7.3 g (0.023 mol) of the compound 25-2 prepared in Example 25-2 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 17-1 prepared in Example 17-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 120 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 13.5 g of compound 30 (yield 78%).

[Example 31] Preparation of compound 31

31-1. Preparation of compound 31-1

In a 1000-mL, 4-neck round-bottom flask, 11.2 g (0.054 mol) of 2-bromonaphthalene was added and diluted with 270 mL of tetrahydrofuran. To this dilution, 9.4 g of (4-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 3 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 11.5 g of compound 31-1 (yield 89%).

31-2. Preparation of compound 31-2

13.8 g (0.058 mol) of the compound 31-1 prepared in Example 31-1 was added to a 500-mL, 3-neck round-bottom flask under a nitrogen atmosphere and diluted with 300 mL of toluene. In this dilution, 19.2 g of 9,9'-spirobi[fluorene]-2-amine, 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and sodium 7.2 g of t-butoxide was added. The reaction solution was refluxed for 3 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 27.2 g of compound 31-2 (yield 88%).

31-3. Preparation of compound 31

To 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 in a 250-mL, 3-neck round-bottom flask, 12.9 g of compound 31-2 prepared in Example 31-2, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.6 g of compound 31 (yield 82%).

[Example 32] Preparation of compound 32

32-1. Preparation of compound 32-1

17.3 g (0.054 mol) of the compound 1-3 prepared in Example 1-3 was added to a 1000-mL, 4-neck round-bottom flask, and diluted with 350 mL of tetrahydrofuran. To this dilution, 9.4 g of (4-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 3 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 16.1 g of compound 32-1 (yield 85%).

32-2. Preparation of compound 32

In a 250-mL, 3-neck round-bottom flask, to 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1, 9.9 g of the compound 1-4 prepared in Example 1-4, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.6 g of compound 32 (yield 88%).

[Example 33] Preparation of compound 33

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.4 g of compound 33 (yield 84%).

[Example 34] Preparation of compound 34

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 3-1 prepared in Example 3-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.7 g of Compound 34 (yield 80%).

[Example 35] Preparation of compound 35

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 4-1 prepared in Example 4-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.1 g of compound 35 (yield 82%).

[Example 36] Preparation of compound 36

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 12.6 g of the compound 5-1 prepared in Example 5-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.9 g of compound 36 (yield 77%).

[Example 37] Preparation of compound 37

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 12.0 g of the compound 6-1 prepared in Example 6-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.1 g of compound 37 (yield 81%).

[Example 38] Preparation of compound 38

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 13.9 g of the compound 7-1 prepared in Example 7-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.7 g of compound 38 (yield 72%).

[Example 39] Preparation of compound 39

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 12.4 g of the compound 10-1 prepared in Example 10-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.1 g of compound 39 (yield 79%).

[Example 40] Preparation of compound 40

In a 250-mL, 3-neck round-bottom flask, to 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1, 14.5 g of the compound 13-2 prepared in Example 13-2, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.8 g of compound 40 (yield 75%).

[Example 41] Preparation of compound 41

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 12.9 g of the compound 31-2 prepared in Example 31-2, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.8 g of compound 41 (yield 76%).

[Example 42] Preparation of compound 42

42-1. Preparation of compound 42-1

In a 500-mL, 3-neck round-bottom flask, 5.4 g (0.058 mol) of the compound aniline was added under a nitrogen atmosphere and diluted with 250 mL of toluene. In this dilution, 22.9 g of 4-bromo-9,9'-spirobi[fluorene], 0.27 g of tris(dibenzylideneacetone)dipalladium(0), 0.12 g of tri-(t-butyl)phosphine, and 7.2 g of sodium t-butoxide was added. The reaction solution was refluxed for 1 hour, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 18.9 g of compound 42-1 (yield 82%).

42-2. Preparation of compound 42

In a 250-mL, 3-neck round-bottom flask, to 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1, 9.9 g of the compound 42-1 prepared in Example 42-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.5 g of compound 42 (yield 87%).

[Example 43] Preparation of compound 43

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 15-1 prepared in Example 15-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 16.5 g of compound 43 (yield 90%).

[Example 44] Preparation of compound 44

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 16-1 prepared in Example 16-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.7 g of Compound 44 (yield 80%).

[Example 45] Preparation of compound 45

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 17-1 prepared in Example 15-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.4 g of compound 45 (yield 84%).

[Example 46] Preparation of compound 46

46-1. Preparation of compound 46-1

17.3 g (0.054 mol) of the compound 1-3 prepared in Example 1-3 was added to a 1000-mL, 4-neck round-bottom flask, and diluted with 350 mL of tetrahydrofuran. In this dilution, 13.2 g of (4-chloro(1,1`-biphenyl)-4-yl)phenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and tetrakis(triphenylphosphine)palladium(0) After adding 1.0 g, the reaction solution was refluxed for 3 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 23.4 g of compound 46-1 (yield 83%).

46-2. Preparation of compound 46

To 9.8 g (0.023 mol) of Compound 46-1 prepared in Example 46-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of Compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 16.5 g of compound 46 (yield 82%).

[Example 47] Preparation of compound 47

47-1. Preparation of compound 47-1

17.3 g (0.054 mol) of the compound 1-3 prepared in Example 1-3 was added to a 1000-mL, 4-neck round-bottom flask, and diluted with 350 mL of tetrahydrofuran. To this dilution, 9.4 g of (3-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 3 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 15.2 g (yield 80%) of compound 47-1.

47-2. Preparation of compound 47

In a 250-mL, 3-neck round-bottom flask, to 8.1 g (0.023 mol) of the compound 47-1 prepared in Example 47-1, 11.7 g of the compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 16.0 g of compound 47 (yield 87%).

[Example 48] Preparation of compound 48

To 8.1 g (0.023 mol) of the compound 47-1 prepared in Example 47-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 15-1 prepared in Example 15-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.5 g of Compound 48 (yield 79%).

[Example 49] Preparation of compound 49

49-1. Preparation of compound 49-1

17.3 g (0.054 mol) of the compound 25-2 prepared in Example 25-2 was added to a 1000-mL, 4-neck round-bottom flask, and diluted with 350 mL of tetrahydrofuran. To this dilution, 9.4 g of (4-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 3 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 16.2 g (yield 85%) of compound 49-1.

49-2. Preparation of compound 49

In a 250-mL, 3-neck round-bottom flask, to 8.1 g (0.023 mol) of the compound 49-1 prepared in Example 49-1, 11.7 g of the compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.8 g of compound 49 (yield 86%).

[Example 50] Preparation of compound 50

50-1. Preparation of compound 50-1

17.3 g (0.054 mol) of the compound 1-3 prepared in Example 1-3 was added to a 1000-mL, 4-neck round-bottom flask, and diluted with 350 mL of tetrahydrofuran. To this dilution, 9.4 g of (2-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 3 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 15.3 g of compound 50-1 (yield 81%).

50-2. Preparation of compound 50

To 8.1 g (0.023 mol) of the compound 50-1 prepared in Example 50-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.9 g of Compound 50 (yield 81%).

[Example 51] Preparation of compound 51

In a 250-mL, 3-neck round-bottom flask, to 8.1 g (0.023 mol) of the compound 49-1 prepared in Example 49-1, 12.0 g of the compound 6-1 prepared in Example 6-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.0 g of compound 51 (yield 75%).

[Example 52] Preparation of compound 52

In a 250-mL, 3-neck round-bottom flask, to 8.1 g (0.023 mol) of the compound 49-1 prepared in Example 49-1, 11.7 g of the compound 17-1 prepared in Example 17-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.5 g of compound 52 (yield 79%).

[Example 53] Preparation of compound 53

In a 250-mL, 3-neck round-bottom flask, to 8.1 g (0.023 mol) of the compound 49-1 prepared in Example 49-1, 11.7 g of the compound 15-1 prepared in Example 15-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.5 g of compound 53 (yield 84%).

[Example 54] Preparation of compound 54

54-1. Preparation of compound 54-1

17.3 g (0.054 mol) of the compound 25-2 prepared in Example 25-2 was added to a 1000-mL, 4-neck round-bottom flask, and diluted with 350 mL of tetrahydrofuran. To this dilution, 9.4 g of (3-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 3 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 14.8 g of compound 54-1 (yield 78%).

54-2. Preparation of compound 54

To 8.1 g (0.023 mol) of compound 54-1 prepared in Example 54-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 14.9 g of compound 54 (yield 81%).

[Example 55] Preparation of compound 55

55-1. Preparation of compound 55-1

17.3 g (0.054 mol) of the compound 25-2 prepared in Example 25-2 was added to a 1000-mL, 4-neck round-bottom flask, and diluted with 350 mL of tetrahydrofuran. To this dilution, 9.4 g of (3-chlorophenyl)boronic acid, 54 mL of 3M-potassium carbonate aqueous solution, and 1.0 g of tetrakis(triphenylphosphine)palladium (0) were added, and the reaction solution was refluxed for 3 hours. After the reaction solution was cooled to room temperature, tetrahydrofuran was concentrated, methanol was added, and the precipitated solid was vacuum filtered. The collected solid compounds were vacuum dried to obtain 13.3 g of compound 55-1 (yield 70%).

55-2. Preparation of compound 55

To 8.1 g (0.023 mol) of the compound 55-1 prepared in Example 55-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of the compound 2-1 prepared in Example 2-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.3 g of compound 55 (yield 83%).

[Example 56] Preparation of compound 56

To 8.1 g (0.023 mol) of compound 55-1 prepared in Example 55-1 in a 250-mL, 3-neck round-bottom flask, 11.7 g of compound 15-1 prepared in Example 15-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 13.6 g of compound 56 (yield 74%).

[Example 57] Preparation of compound 57

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 13.9 g of the compound 11-1 prepared in Example 11-1, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 16.4 g of compound 57 (yield 80%).

[Example 58] Preparation of compound 58

To 8.1 g (0.023 mol) of the compound 32-1 prepared in Example 32-1 in a 250-mL, 3-neck round-bottom flask, 13.9 g of the compound 9-2 prepared in Example 9-2, palladium acetate (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 150 mL were added. The reaction solution was refluxed for 4 hours, cooled, and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by column to obtain 15.8 g of compound 58 (yield 77%).

[Example 59]

The Li substrate on which a transparent anode of indium tin oxide (ITO) having a film thickness of 1200 Å was formed was thoroughly washed and then placed in a vacuum deposition apparatus, and the pressure was reduced to ^{about 10 -7 torr.} Then, the following compound RHI was deposited to a thickness of 50 Å to form a hole injection layer. Then, the compound 1 of the present invention was deposited to a thickness of 800 Å to form a hole transport layer. Then, the following compound RHT2 was deposited to a thickness of 150 Å to form an electron blocking layer. Subsequently, the following compound BH1 as a blue host and the following compound BD1 as a blue dopant were simultaneously deposited at a weight ratio of 97:3 to form an emission layer having a thickness of 250 Å. Then, the EET1 compound manufactured by ELM was deposited to a thickness of 200 Å to form an electron transport layer 1. Next, EET2, a compound manufactured by ELM, was deposited to a thickness of 50 Å to form an electron transport layer 2. Then, lithium fluoride (LiF) was deposited to a thickness of 15 Å to form an electron injection layer. Finally, aluminum was deposited to a thickness of 2000 Å to form a cathode. A light emission test was performed by applying a voltage to the organic electroluminescent device fabricated as described above. Table 1 shows the measured applied voltage, luminous efficiency, and luminous color at a luminance of 500 cd/m ^{2 .}

[Example 60] to [Example 98]

In Example 59, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 59, except that the compound of the present invention described in Table 1 was used instead of Compound 1 as the hole transport layer.

Example hole transport layer
ingredient electronic barrier layer
ingredient drive voltage
(V) Luminous Efficiency
(cd/A) luminous color Example 59 compound 1 RHT2 4.3 7.0 blue Example 60 compound 2 RHT2 3.9 7.8 blue Example 61 compound 3 RHT2 4.2 7.3 blue Example 62 compound 4 RHT2 3.8 7.8 blue Example 63 compound 5 RHT2 4.2 7.4 blue Example 64 compound 6 RHT2 4.2 7.1 blue Example 65 compound 7 RHT2 4.3 7.2 blue Example 66 compound 8 RHT2 4.5 7.4 blue Example 67 compound 10 RHT2 4.4 6.9 blue Example 68 compound 11 RHT2 4.5 6.8 blue Example 69 compound 13 RHT2 4.3 7.0 blue Example 70 compound 14 RHT2 4.2 7.0 blue Example 71 compound 15 RHT2 4.4 7.1 blue Example 72 compound 16 RHT2 4.4 7.0 blue Example 73 compound 17 RHT2 4.4 7.3 blue Example 74 compound 18 RHT2 4.5 6.8 blue Example 75 compound 20 RHT2 4.5 6.8 blue Example 76 compound 22 RHT2 4.5 7.3 blue Example 77 compound 24 RHT2 4.3 7.5 blue Example 78 compound 25 RHT2 4.0 7.6 blue Example 79 compound 26 RHT2 4.2 7.3 blue Example 80 compound 27 RHT2 4.1 7.8 blue Example 81 compound 28 RHT2 4.3 7.0 blue Example 82 compound 30 RHT2 4.4 6.8 blue Example 83 compound 31 RHT2 3.9 7.4 blue Example 84 compound 32 RHT2 4.0 7.4 blue Example 85 compound 33 RHT2 3.8 7.9 blue Example 86 compound 34 RHT2 4.0 7.8 blue Example 87 compound 35 RHT2 3.9 7.9 blue Example 88 compound 36 RHT2 4.0 7.6 blue Example 89 compound 37 RHT2 4.4 7.5 blue Example 90 compound 38 RHT2 4.5 7.2 blue Example 91 compound 40 RHT2 4.0 7.6 blue Example 92 compound 41 RHT2 3.9 7.5 blue Example 93 compound 46 RHT2 4.5 6.9 blue Example 94 compound 47 RHT2 3.9 7.7 blue Example 95 compound 49 RHT2 3.8 7.7 blue Example 96 compound 50 RHT2 4.0 7.5 blue Example 97 compound 54 RHT2 4.0 7.5 blue Example 98 compound 55 RHT2 4.1 7.7 blue

[Example 99]

The Li substrate on which a transparent anode of indium tin oxide (ITO) having a film thickness of 1200 Å was formed was thoroughly washed and then placed in a vacuum deposition apparatus, and the pressure was reduced to ^{about 10 -7 torr.} Then, the following compound RHI was deposited to a thickness of 50 Å to form a hole injection layer. Then, the compound RHT1 was deposited to a thickness of 800 Å to form a hole transport layer. Then, the compound 2 of the present invention was deposited to a thickness of 150 Å to form an electron blocking layer. Subsequently, the following compound BH1 as a blue host and the following compound BD1 as a blue dopant were simultaneously deposited at a weight ratio of 97:3 to form an emission layer having a thickness of 250 Å. Then, the EET1 compound manufactured by ELM was deposited to a thickness of 200 Å to form an electron transport layer 1. Next, EET2, a compound manufactured by ELM, was deposited to a thickness of 50 Å to form an electron transport layer 2. Then, lithium fluoride (LiF) was deposited to a thickness of 15 Å to form an electron injection layer. Finally, aluminum was deposited to a thickness of 2000 Å to form a cathode. A light emission test was performed by applying a voltage to the organic electroluminescent device fabricated as described above. Table 2 shows the measured applied voltage, luminous efficiency, and luminous color at a luminance of 500 cd/m ^{2 .}

[Example 100] to [Example 136]

In Example 99, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 99, except that the compound of the present invention described in Table 2 was used instead of Compound 2 as the electron blocking layer.

Example hole transport layer
ingredient electronic barrier layer
ingredient drive voltage
(V) Luminous Efficiency
(cd/A) luminous color Example 99 RHT1 compound 2 4.3 7.4 blue Example 100 RHT1 compound 4 4.3 7.3 blue Example 101 RHT1 compound 6 4.1 7.6 blue Example 102 RHT1 compound 7 4.2 7.6 blue Example 103 RHT1 compound 8 4.2 7.2 blue Example 104 RHT1 compound 9 4.1 7.8 blue Example 105 RHT1 compound 10 4.2 7.2 blue Example 106 RHT1 compound 11 4.1 7.7 blue Example 107 RHT1 compound 12 4.5 6.7 blue Example 108 RHT1 compound 15 4.0 7.5 blue Example 109 RHT1 compound 16 4.1 7.2 blue Example 110 RHT1 compound 17 4.0 7.5 blue Example 111 RHT1 compound 18 4.1 7.6 blue Example 112 RHT1 compound 19 4.2 7.4 blue Example 113 RHT1 compound 20 4.1 7.5 blue Example 114 RHT1 compound 21 4.2 7.5 blue Example 115 RHT1 compound 22 4.5 7.0 blue Example 116 RHT1 compound 23 4.0 7.3 blue Example 117 RHT1 compound 28 4.0 7.6 blue Example 118 RHT1 compound 29 4.0 7.5 blue Example 119 RHT1 compound 30 4.0 7.6 blue Example 120 RHT1 compound 33 4.3 7.5 blue Example 121 RHT1 compound 34 4.3 7.3 blue Example 123 RHT1 compound 37 4.2 7.4 blue Example 124 RHT1 compound 38 4.2 7.4 blue Example 125 RHT1 compound 39 4.1 7.5 blue Example 126 RHT1 compound 42 4.1 7.4 blue Example 127 RHT1 compound 43 3.8 7.9 blue Example 128 RHT1 compound 44 3.9 7.6 blue Example 129 RHT1 compound 45 3.7 7.8 blue Example 130 RHT1 compound 48 4.0 7.8 blue Example 131 RHT1 compound 51 4.2 7.5 blue Example 132 RHT1 compound 52 4.0 7.7 blue Example 133 RHT1 compound 53 3.9 7.6 blue Example 134 RHT1 compound 56 3.8 7.9 blue Example 135 RHT1 compound 57 4.0 7.8 blue Example 136 RHT1 compound 58 3.9 7.9 blue

[Example 137]

The Li substrate on which a transparent anode of indium tin oxide (ITO) having a film thickness of 1200 Å was formed was thoroughly washed and then placed in a vacuum deposition apparatus, and the pressure was reduced to ^{about 10 -7 torr.} Then, the following compound RHI was deposited to a thickness of 50 Å to form a hole injection layer. Then, the compound 2 of the present invention was deposited to a thickness of 800 Å to form a hole transport layer. Then, the compound 6 of the present invention was deposited to a thickness of 150 Å to form an electron blocking layer. Subsequently, the following compound BH1 as a blue host and the following compound BD1 as a blue dopant were simultaneously deposited at a weight ratio of 97:3 to form an emission layer having a thickness of 250 Å. Then, the EET1 compound manufactured by ELM was deposited to a thickness of 200 Å to form an electron transport layer 1. Next, EET2, a compound manufactured by ELM, was deposited to a thickness of 50 Å to form an electron transport layer 2. Then, lithium fluoride (LiF) was deposited to a thickness of 15 Å to form an electron injection layer. Finally, aluminum was deposited to a thickness of 2000 Å to form a cathode. A light emission test was performed by applying a voltage to the organic electroluminescent device fabricated as described above. Table 3 shows the measured applied voltage, luminous efficiency, and luminous color at a luminance of 500 cd/m ^{2 .}

[Example 138] to [Example 156]

In Example 137, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 137, except that the compound of the present invention described in Table 3 was used for the hole transport layer and the electron blocking layer, respectively.

[Comparative Example 1] to [Comparative Example 8]

In Example 137, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 137, except that the following compounds described in Table 3 were used for the hole transport layer and the electron blocking layer, respectively.

Example hole transport layer
ingredient electronic barrier layer
ingredient drive voltage
(V) Luminous Efficiency
(cd/A) luminous color Example 137 compound 2 compound 6 3.9 7.9 blue Example 138 compound 2 compound 15 3.8 8.0 blue Example 139 compound 2 compound 17 3.8 8.0 blue Example 140 compound 2 compound 18 3.8 8.1 blue Example 141 compound 25 compound 15 3.9 7.9 blue Example 142 compound 25 compound 17 3.9 7.8 blue Example 143 compound 25 compound 28 3.9 7.8 blue Example 144 compound 27 compound 30 3.8 7.8 blue Example 145 compound 33 compound 7 3.7 8.0 blue Example 146 compound 33 compound 15 3.8 8.0 blue Example 147 compound 33 compound 18 3.8 8.0 blue Example 148 compound 33 compound 28 3.7 8.0 blue Example 149 compound 33 compound 43 3.7 8.2 blue Example 150 compound 33 compound 56 3.7 8.1 blue Example 151 compound 35 compound 43 3.8 8.1 blue Example 152 compound 35 compound 45 3.8 8.0 blue Example 153 compound 47 compound 48 3.8 7.9 blue Example 154 compound 49 compound 53 3.7 7.9 blue Example 155 compound 50 compound 53 3.7 8.1 blue Example 156 compound 50 compound 56 3.8 8.1 blue Comparative Example 1 RHT1 RHT2 5.6 5.5 blue Comparative Example 2 EHT1 RHT2 4.9 6.6 blue Comparative Example 3 EHT2 RHT2 5.2 6.2 blue Comparative Example 4 EHT3 RHT2 5.3 6.0 blue Comparative Example 5 EHT4 RHT2 4.7 6.6 blue Comparative Example 6 RHT1 EHT5 5.1 6.3 blue Comparative Example 7 RHT1 EHT6 5.3 6.0 blue Comparative Example 8 RHT1 EHT7 5.3 5.7 blue

As described above, organic electroluminescent devices of Examples 59 to 156 and Comparative Examples 1 to 8 were manufactured using the compounds prepared according to Examples 1 to 58. The hole transport layer material, the electron blocking layer material, the driving voltage, the luminous efficiency and the luminous color are summarized in Tables 1 to 3 above.

As can be seen from Tables 1 to 3, the organic electroluminescent devices according to Examples 59 to 156 of the present invention can operate at a lower driving voltage than Comparative Examples 1 to 8, and exhibit higher luminous efficiency. It can be seen that you have

Specifically, compounds 1 to 58 according to the above Examples are all aromatic compounds including an indolocarbazolyl group and a spirobifluorenyl group, and compared to the case where they are not (Comparative Examples 1 to 8), the driving voltage is lower and The luminous efficiency has a higher effect.

In addition, when the present invention is L ₁ of the formula (I) linking group according to, or L ₁ or L _3, or an arylene group, a heterocyclic group of the formula (III) of the formula (I), exhibited a still more excellent light emitting property than before.

In addition, when R2 of Formula I is an aryl group (or biphenyl), when the compound is used in a hole transport layer or an electron blocking layer, the luminous efficiency and lifespan of the device are further improved.

In addition, when the compound in which L ₂ of Formula I is a linking group was used for the hole transport layer or the electron blocking layer, the luminous efficiency and lifespan of the device were further improved.

Although the present invention has been shown and described in relation to specific preferred embodiments, the present invention may be modified and changed in various ways without departing from the technical features or fields of the present invention provided by the following claims. It will be apparent to those of ordinary skill in the art.

Claims (9)

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

In Formula I, L ₁ and L ₂ are each a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted A cyclic alkenylene group, or a linker,
R ₁ is a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted an alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted silyl group, or a cyano group,
R ₂ to R ₈ are each independently a hydrogen atom, a deuterium atom, a halogen group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylox a group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, or a cyano group,
a is an integer from 0 to 2, b to f are each an integer from 0 to 4, g is an integer from 0 to 3, and when a to g is 2 or more, the substituents in parentheses are the same or different.
According to claim 1,
A compound, characterized in that it is used as a light emitting material of an organic light emitting diode (Organic Light Emitting Diode).
According to claim 1,
The formula (I) is a compound characterized in that the formula (II) or formula (III):
[Formula II]

[Formula III]

In Formulas II and III, L ₂ , R ₁ to R ₈ , and a to g are as defined in Formula I, and L ₃ is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group am.
According to claim 1,
The formula (I) is a compound characterized in that the formula (IV) or formula (V):
[Formula IV]

[Formula V]

In Formula IV and Formula V, L ₁ , L ₂ , R ₁ to R ₈ , and a to g are as defined in Formula I.
According to claim 1,
The formula (I) is a compound characterized in that the formula (VI), or formula (VII):
[Formula VI]

[Formula VII]

In Formulas VI and VII, L ₁ , R ₁ to R ₈ , and a to g are as defined in Formula I above, and L ₄ is a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group .
According to claim 1,
Formula I is a compound characterized in that it is selected from the group consisting of:

A compound according to any one of claims 1 to 6,
An organic electroluminescent composition, characterized in that it is used as a light emitting material of an organic electroluminescent device (Organic Light Emitting Diode).
A compound according to any one of claims 1 to 6,
An organic electroluminescent composition, characterized in that it is used for a hole transport layer or an electron blocking layer of an organic light emitting diode (Organic Light Emitting Diode).
An organic electroluminescent device comprising at least one organic layer comprising the composition according to claim 7 .

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