KR20200095710A - 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 an organic electroluminescent device using the same. More particularly, the present invention relates to an indolocarbazole derivative compound having an amine substituent. When using the indolocarbazole derivative compound as a light emitting material for an organic layer of an organic electroluminescent device, an effect of deriving high luminous efficiency even with a low driving voltage can be provided.

Description

Organic electroluminescent composition and organic electroluminescent device comprising the same

The present invention relates to an organic electroluminescent device, and more particularly, to an indolocarbazole derivative compound used as a light emitting material for an organic electroluminescent device, and more specifically, an indolocarbazole derivative compound having an amine substituent, an organic compound containing the same It relates to an electroluminescent composition, and an organic electroluminescent device comprising the same.

Organic electroluminescent devices, which have several advantages such as low voltage driving, self-emission, light weight, thin viewing angle, and fast response speed, are one of the next-generation flat panel displays and have been actively researched in recent years.

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

The organic film of the organic electroluminescent device is not a simple structure, but by using 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, etc. The performance of the organic electroluminescent device could be improved.

In order to improve light emission characteristics such as driving voltage and luminous efficiency of the organic electroluminescent device and to extend the life 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 relate to Korean Patent Registration No. 10-1555816 (Announcement Date: 2015.09.25., Title of Invention: Organic Electroluminescent Composition and Organic Electroluminescent Device Containing the Same), Korean Patent No. 10-1529878 ( Announcement date: 2015.06.18., Title of invention: organic electroluminescent composition and organic electroluminescent device including the same), Korean Patent Registration No. 10-1627211 (announcement date: 2016.06.13, title of invention: containing aromatic compounds) Through the organic electroluminescent composition and the organic electroluminescent device including the same), various aromatic amine derivative compounds have been invented. The compounds described herein have high luminance and luminous efficiency.

However, there is a need for a new compound that operates at a lower driving voltage than the existing one and has a higher luminous efficiency.

Korean 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.)

The present invention for solving the above problems is to provide a compound having a high luminous efficiency even with a low driving voltage when used as a light emitting material in the organic layer of the 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.

In addition, another object of the present invention is to provide a novel compound and a method for manufacturing the same, which can improve the luminous efficiency of the organic electroluminescent device and increase the life of the device.

In addition, another object of the present invention is to provide an organic electroluminescent device having high luminous efficiency and extended life.

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

[Formula I]

In Formula I, L ₁ is a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, or a linker,

R ₁ is one of the structures represented by Formula II below,

[Formula II]

(In the formula II, R ₁₁ and R ₁₂ are hydrogen atom, deuterium atom, halogen group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkyl group, substituted or unsubstituted An aryloxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted silyl group, or a cyano group,

X is an oxygen atom, a sulfur atom, CY ₂ (Y is a hydrogen atom, an alkyl group, or an aryl group),

d and e are integers from 0 to 4, and when 2 or more, the substituents in parentheses are the same or different, and)

R ₂ to R ₅ 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 aryl group. 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 of 0 to 3, b and c are an integer of 0 to 4, and when a to c is 2 or more, the substituents in parentheses are the same or different.

Specific 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, it is possible to achieve high luminous efficiency even with a low driving voltage.

In addition, since the compound according to the present invention has high glass transition ionicity and thermal decomposition temperature, it is excellent in thermal stability. As a result of evaluating luminescence characteristics using a composition containing this in an organic electroluminescent device, current density, luminance, and maximum It showed excellent luminescence characteristics in terms of luminance and luminous efficiency.

In addition, when an organic electroluminescent device is fabricated 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 solved at the same time, and the glass transition temperature is also high. Therefore, since the organic electroluminescent device is excellent in thermal stability, a high-performance organic electroluminescent device can be manufactured, and it can greatly contribute to the commercialization of an organic electroluminescent device that requires high efficiency, high brightness, and long life.

1 is a diagram 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 MALDI-TOF MS spectrum of Compound 3 according to an embodiment of the present invention.
3 is UV/Vis of Compound 12 according to an embodiment of the present invention. Absorbance, fluorescence PL and low temperature PL spectrum graph.
4 is a differential scanning calorimeter (DSC) curve graph of Compound 12 according to an embodiment of the present invention.

The present invention can be applied to a variety of transformations and may have various embodiments, and specific embodiments will be 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 should be understood to include all conversions, equivalents, and substitutes included in the spirit and scope of the present invention. In the description of the present invention, when it is determined that a detailed description of known technologies related to the present invention may obscure the subject matter of the present invention, the detailed description will be omitted.

The terms used in this application are only used to describe specific embodiments, and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, terms such as “include” or “have” are intended to indicate that a feature, number, step, operation, component, part, or combination thereof described in the specification exists, and that one or more other features are present. It should be understood that the existence or addition possibilities of fields or numbers, steps, operations, components, parts or combinations thereof are not excluded in advance.

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

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, and is an indolocarbazole derivative compound having an amine substituent. Since the compound according to the present invention has a high glass transition temperature, excellent hole injection, and transport ability, when an organic electroluminescent device is manufactured using the compound, the luminous efficiency can be further improved even at a low driving voltage, thereby increasing the life of the device. Can be increased.

[Formula I]

In Formula I, L ₁ is a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, or a linker,

R ₁ is one of the structures represented by Formula II below,

[Formula II]

(In the formula II, R ₁₁ and R ₁₂ are hydrogen atom, deuterium atom, halogen group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkyl group, substituted or unsubstituted An aryloxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted silyl group, or a cyano group,

X is an oxygen atom, a sulfur atom, CY ₂ (Y is a hydrogen atom, an alkyl group, or an aryl group),

d and e are integers from 0 to 4, and when 2 or more, the substituents in parentheses are the same or different, and)

R ₂ to R ₅ 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 aryl group. 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 of 0 to 3, b and c are an integer of 0 to 4, and when a to c 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 not substituted by any functional group, wherein the functional group is a group of organic groups having common chemical properties. It refers to a common atomic group that contributes to its properties in a compound, or a bond form thereof.

In Formula I, L ₁ may be a substituted or unsubstituted arylene group, a heterocyclic group, an alkylene group, an alkenylene group, or a linking group. That is, the present invention is characterized in that a heterocyclic aromatic such as a fluorene group is included in the central structure formed by connecting the indolocarbazole and the amine substituent simply or by an aromatic ring.

The arylene group may be arenediyl groups in which hydrogen atoms are removed one by one from carbon atoms at both ends of the arenes, and the alkylene group is at both ends of the alkane. It is possible to form hydrogen atoms one by one (-CnH2n-) from the carbon atom (for example, propylene), and the alkenylene group may be one in which the hydrogen atom is removed from the carbon atom at both ends of the alkene. Can.

The present inventors have been studying various aromatic amine derivative compounds that exhibit excellent luminescence properties for a long period of time. After confirming that the compound containing an aromatic functional group exhibits more excellent luminescence properties than the conventional one, the present invention was completed.

As can be seen in the 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 a high luminous efficiency even at a lower driving voltage than other conventional compounds.

However, in the present invention, in formula II wherein L ₁ of formula I is a linker, R ₂ is a biphenyl group, a to c are 0, and R ₁ , X is CY ₂ (Y is a hydrogen atom), and d And e is 0 (EHT4, Comparative Example 5), as a result of the confirmation, the driving voltage is high and the luminous efficiency is low, so it is preferable to exclude it from the present invention.

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

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

As an embodiment of the present invention, the formula (I) may be a compound characterized by the following formula (III), formula (IV), or formula (V).

[Formula III] [Formula IV] [Formula V]

In Formula III, Formula IV, and Formula V, R ₂ to R ₅ , R ₁₁ , and a to d are as defined in Formula I, and R ₆ and R ₇ are each independently a hydrogen atom, a deuterium atom, It is a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group.

In addition, as an embodiment of the present invention, L ₁ of formula I is more preferably a linker.

That is, in Formula (I), R ₁ may have a basic structure of a fluorene group such as Formula (II), X in Formula (II) may be an oxygen atom, a sulfur atom, or CY ₂ (Y is a hydrogen atom, an alkyl group, or an aryl group). , Especially, X is more preferably CY ₂ (Y is a hydrogen atom, an alkyl group, or an aryl group).

[Formula II]

In other words, Formula II may be based on a dibenzofuran group in which X is an oxygen atom, and may be based on a dibenzothiophene group in which X is a sulfur atom, and X is CY ₂ (Y is a hydrogen atom, an alkyl group, or It is also possible that it is a fluorene group which is an aryl group). Among them, X is more preferably CY ₂ (Y is a hydrogen atom, an alkyl group, or an aryl group).

As can be seen in Examples to be described later, in the case where R ₁ in Formula I has the same structure as Formula II (R ₁ is a dibenzofuran group, a dibenzothiophene group, or a fluorene group, in other words, the above When the formula (I) is the formula (III), the formula (IV), and the formula (V), more excellent luminescence properties than the conventional one were shown. Among them, when R ₁ is a fluorene group (when Formula I is Formula III), hole mobility is excellent, and thus even better light emission characteristics are exhibited in all cases used as a hole transport layer or an electron blocking layer.

Further, the compound represented by Formula III was more effective when used as a hole transport layer, and the compounds represented by Formula IV and Formula V were more effective when used as an electron blocking layer.

In addition, as an embodiment of the present invention, the formula I may be a compound characterized in that the formula VI, formula VII, or formula VIII.

[Formula VI] [Formula VII] [Formula VIII]

In Formula VI, Formula VII, and Formula VIII, L ₁ , R ₁ , R ₃ to R ₅ , and a to c are as defined in Formula I.

That is, in the general formula (I), R ₂ is more preferably an aryl group (particularly, a biphenyl group). In other words, in the present invention, the amine substituent has two functional groups (or functional groups), at least one (R ₁ ) has the structure of Formula II as described above, and the other (R ₂ ) is a hydrogen atom, a deuterium atom. , A halogen group, an aryl group, a heteroaryl group, an alkyl group, an aryloxy group, an alkoxy group, an alkoxycarbonyl group, an amino group, a silyl group, or a cyano group, among which the other (R ₂ ) is more preferably an aryl group desirable.

As can be seen in the examples to be described later, in the case where R ₂ in Formula I is an aryl group (or biphenyl), when the compound is used in the hole transport layer or the electron blocking layer, the luminous efficiency and lifetime of the device are reduced. Even more improved.

According to the above, the formula (I) of the present invention may be characterized by being selected from the group consisting of the following compounds. The present invention is an aromatic amine derivative having the structure of Formula I, and a specific example enabling an organic electroluminescent device having a particularly high luminous efficiency and a long life includes at least one selected from the following structural formula. However, the present invention is not limited to these.

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

When a derivative, composition, or material according to the present invention is used in an organic electroluminescent device, excellent luminous efficiency can be obtained, and a device having excellent durability can be manufactured because the glass transition temperature of the indolocarbazole derivative is high. Here, the indolocarbazole derivative compound 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, and preferably, used as a hole transport layer or an electron blocking layer When the most effective.

The organic light emitting composition and the organic electroluminescent device comprising the same according to the present invention include organic light emitting diodes, organic field-effect transistors, organic thin film transistors, organic laser diodes, organic solar cells, organic light emitting electrochemical cells, and organic integrated circuits Can also be used in the field.

In addition, the aromatic amine derivatives according to the present invention can 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 organic electroluminescent composition described above. 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, It is clear to those of ordinary skill in the art that it can be applied in various ways such as diodes.

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

[Example 1] Preparation of compound 1

1-1. Preparation of compound 1-1

To a 500-mL, 3-neck round bottom flask, 9.7 g (0.058 mol) of compound carbazole was added under a nitrogen atmosphere and diluted with 200 mL of dimethyl sulfoxide. To this diluted solution, 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 with 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

3000-mL, 4-neck round bottom flask Compound 1-1 prepared in Example 1-1 22 g (0.069 mol) of palladium acetate (II) 1.6 g, triphenylphosphine 3.6 g, potassium carbonate 43 g tetrabutyl 11 g of ammonium bromide and 2200 mL of dimethylacetamide were added. The reaction solution was stirred at 150° C. for 20 hours, and then dimethylacetamide was concentrated under reduced pressure. The concentrated solution was diluted with dichloromethane and extracted with 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

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

1-4. Preparation of compound 1

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-necked round bottom flask, 9,9-dimethyl- N -phenyl-9 H -fluoren-2-amine 9.2 g , 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl)phosphine, 2.8 g of sodium t-butoxide, and 80 mL of o -xylene were added. The reaction solution was refluxed for 4 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 10.8 g (90% yield) of compound 1 .

[Example 2] Preparation of Compound 2

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-3-yl)-9,9 -dimethyl -9 H-fluorene-2-amine 9.2 g, palladium acetate (II) 0.03 g, tree - (t- butyl) phosphine 0.05 g, sodium t- butoxide, and 2.8 g o-xylene the alkylene 80 mL Was put in. The reaction solution was refluxed for 4 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to give 7.7 g (yield 56%) of compound 2 .

[Example 3] Preparation of compound 3

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-2-yl)-9,9 -dimethyl -9 H-fluorene-2-amine 9.1 g, palladium acetate (II) 0.03 g, tree - (t- butyl) phosphine 0.05 g, sodium t- butoxide, and 2.8 g o-xylene the alkylene 80 mL Was put in. The reaction solution was refluxed for 4 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to obtain 8.4 g of compound 3 (yield 61%).

[Example 4] Preparation of compound 4

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-4-yl)-9,9 - diphenyl -9 H-fluorene-2-amine 12.2 g, palladium acetate (II) 0.03 g, tree - (t- butyl) phosphine 0.05 g, sodium t- butoxide, and 2.8 g o-xylene and 80 mL Was put in. The reaction solution was refluxed for 5 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 10.6 g (64% yield) of compound 4 .

[Example 5] Preparation of compound 5

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-2-yl)-9,9 - diphenyl -9 H-fluorene-2-amine 12.2 g, palladium acetate (II) 0.03 g, tree - (t- butyl) phosphine 0.05 g, sodium t- butoxide, and 2.8 g o-xylene and 80 mL Was put in. The reaction solution was refluxed for 5 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 9.9 g (yield 60%) of compound 5 .

[Example 6] Preparation of compound 6

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to 6.5 g of N -phenyldibenzo[b,d]-furan-4-amine, and 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 1 hour, cooled, and poured into an excess of methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 8.5 g (yield 75%) of compound 6 .

[Example 7] Preparation of compound 7

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-4-yl)dibenzo[b , d]-furan-4-amine 8.4 g, 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 1 hour, cooled, and poured into an excess of methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 8.0 g (yield 61%) of compound 7 .

[Example 8] Preparation of compound 8

In a 250-mL, 3-neck round bottom flask, 8.4 g of N ,6-diphenyldibenzo[b,d]-furan-4-amine in 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 , 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl)phosphine, 2.8 g of sodium t-butoxide, and 80 mL of o -xylene were added. The reaction solution was refluxed for 3 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to give 7.7 g (59% yield) of compound 8 .

[Example 9] Preparation of compound 9

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of compound 1-3 prepared in Example 1-3 was added to N -phenyldibenzo[b,d]-furan-3-amine 6.5 g, 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 3 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 9.2 g (89% yield) of compound 9 .

[Example 10] Preparation of compound 10

In a 250-mL, 3-neck round bottom flask, 8.4 g of N ,6-diphenyldibenzo[b,d]furan-3-amine in 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3, 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl)phosphine, 2.8 g of sodium t-butoxide, and 80 mL of o -xylene were added. The reaction solution was refluxed for 3 hours, then 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 7.8 g (yield 60%) of compound 10 .

[Example 11] Preparation of compound 11

In a 250-mL, 3-necked round-bottom flask, 8.4 g of N ,6-diphenyldibenzo[b,d]furan-2-amine in 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3, 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl)phosphine, 2.8 g of sodium t-butoxide, and 80 mL of o -xylene were added. The reaction solution was refluxed for 3 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to give 9.3 g (71% yield) of compound 11 .

[Example 12] Preparation of compound 12

250-mL, 3-neck round 4 in Example 1-3 7.3 g of the compound 1-3 (0.023 mol) prepared in the bottom flask ((9,9-dimethyl -9 H-fluoren-fruit-yl) amino ) 7.8 g of benzonitrile, 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl) phosphine, 2.8 g of sodium t-butoxide, and 80 mL of o -xylene were added. The reaction solution was refluxed for 3 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to give 4.5 g (yield 36%) of compound 12 .

[Example 13] Preparation of compound 13

13-1. Preparation of compound 13-1

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-4-yl)-9,9 -dimethyl -9 H-fluorene-2-amine 9.2 g, palladium acetate (II) 0.03 g, tree - (t- butyl) phosphine 0.05 g, sodium t- butoxide, and 2.8 g o-xylene the alkylene 80 mL Was put in. The reaction solution was refluxed for 4 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to give 10.3 g (75% yield) of compound 13-1 .

13-2. Preparation of compound 13-2

Into a 1000-mL, 4-neck round bottom flask, 16.2 g (0.027 mol) of compound 13-1 prepared in Example 13-1 was added and diluted with 320 mL of chloroform. 14.4 g of N -bromosuccinimide (NBS) was slowly added to this dilution and refluxed for 15 hours. After adding 320 mL of distilled water to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The separated organic layer was dried, concentrated, recrystallized with acetonitrile and ethyl acetate, and dried in vacuo to give 9.2 g (yield 45%) of compound 13-2 .

13-3. Preparation compound 13

Into a 1000-mL, 4-neck round bottom flask, 10.2 g (0.014 mol) of compound 13-2 prepared in Example 13-2 was added and diluted with 250 mL of tetrahydrofuran. To this diluted solution, 3.8 g of phenylboronic acid, 27 mL of 3M-potassium carbonate aqueous solution, and 0.5 g of tetrakis (triphenylphosphine) palladium (0) were added, and the reaction solution was refluxed for 4 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 compound was filtered, dried in vacuo, and separated by a column to give 7.3 g (72% yield) of compound 13 .

[Example 14] Preparation of compound 14

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-2-yl)-9,9 -dimethyl -9 H-fluoren-l-amine 9.1 g, palladium acetate (II) 0.03 g, tree - (t- butyl) phosphine 0.05 g, sodium t- butoxide, and 2.8 g o-xylene the alkylene 80 mL Was put in. The reaction solution was refluxed for 4 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 7.1 g (yield 52%) of compound 14 .

[Example 15] Preparation of compound 15

In a 250-mL, 3-neck round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-4-yl)-9,9 -dimethyl -9 H-fluoren-4-amine 9.1 g, palladium acetate (II) 0.03 g, tree - (t- butyl) phosphine 0.05 g, sodium t- butoxide, and 2.8 g o-xylene the alkylene 80 mL Was put in. The reaction solution was refluxed for 4 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 7.9 g (yield 58%) of compound 15 .

[Example 16] Preparation of compound 16

In a 250-mL, 3-neck round-bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added N- (4-fluorophenyl) -9,9-dimethyl-9 H -fluorene 7.3 g of -2-amine, 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl)phosphine, 2.8 g of sodium t-butoxide, and 80 mL of o -xylene were added. The reaction solution was refluxed for 5 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 7.4 g (yield 60%) of compound 16 .

[Example 17] Preparation of compound 17

17-1. Preparation of compound 17-1

In a 500-mL, 3-neck round bottom flask, 9.8 g (0.058 mol) of the compound (1,1`-biphenyl)-4-amine was added in a nitrogen atmosphere and diluted with 300 mL of toluene. To the diluted solution of 2,7-dibromo-9,9-dimethyl -9 H - 20.4 g fluorene, tris (dibenzylideneacetone) di-palladium (0), 0.27 g, tree - (t- butyl) phosphine 0.12 g and 7.2 g of sodium t-butoxide were added. The reaction solution was refluxed for 2 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried under vacuum, and then separated by a column to give 12.0 g (yield 47%) of compound 17-1 .

17-2. Preparation compound 17-2

To a 1000-mL, 4-neck round bottom flask, 12 g (0.027 mol) of the compound 17-1 prepared in Example 17-1 was added and diluted with 240 mL of tetrahydrofuran. To this dilution, 3.7 g of phenylboronic acid, 27 mL of 3M-potassium carbonate aqueous solution, and 0.5 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 compound was vacuum-dried to obtain 10.1 g of compound 17-2 (yield 85%).

17-3. Preparation compound 17

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, 3-necked round bottom flask, 11.0 g of Compound 17-2 prepared in Example 17-2, 0.03 palladium acetate (II) g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 90 mL were added. The reaction solution was refluxed for 3 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 11.1 g (72% yield) of compound 17 .

[Example 18] Preparation of compound 18

250-mL, 3 gu a solution of the compound prepared in Example 1-3 in a round bottom flask 1-3 7.3 g (0.023 mol) in bis (9,9-dimethyl -9 H - fruit fluoren-2-yl) amine 10.1 g , 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl)phosphine, 2.8 g of sodium t-butoxide, and 100 mL of o -xylene were added. The reaction solution was refluxed for 2 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to give 11.2 g of compound 18 (yield 77%).

[Example 19] Preparation of compound 19

In a 250-mL, 3-necked round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to 6.9 g of N -phenyldibenzo[b,d]thiophen-4-amine, palladium acetate. (II) 0.03 g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 70 mL were added. The reaction solution was refluxed for 1 hour, cooled, and poured into an excess of methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to give 8.3 g (yield 71%) of compound 19 .

[Example 20] Preparation of compound 20

In a 250-mL, 3-neck round bottom flask, 8.4 g of N ,6-diphenyldibenzo[b,d]thiophen-4-amine in 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 , 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl) phosphine, 2.8 g of sodium t-butoxide, and 70 mL of o -xylene were added. The reaction solution was refluxed for 3 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 8.8 g (yield 65%) of compound 20 .

[Example 21] Preparation of compound 21

In a 250-mL, 3-necked round bottom flask, 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 was added to N -((1,1`-biphenyl)-4-yl)-6-phenyl. 10.2 g of dibenzo[b,d]thiophen-4-amine, 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl)phosphine, 2.8 g of sodium t-butoxide and 70 mL of o -xylene Was put in. The reaction solution was refluxed for 5 hours, then 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 9.4 g (62% yield) of compound 21 .

[Example 22] Preparation of compound 22

22-1. Preparation compound 22-1

In a 500-mL, 3-neck round bottom flask, 9.8 g (0.058 mol) of the compound (1,1`-biphenyl)-4-amine was added in a nitrogen atmosphere and diluted with 300 mL of toluene. To this diluent, 20.3 g of 2-(4-bromophenyl)-9,9-dimethyl-9 H -fluorene, tris(dibenzylideneacetone)dipalladium(0) 0.27 g, tri-(t-butyl)phos 0.12 g of pin and 7.2 g of sodium t-butoxide were added. The reaction solution was refluxed for 1 hour, cooled, and poured into an excess of methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to obtain 20.1 g (79% yield) of compound 22-1 .

22-2. Preparation compound 22

To 7.3 g (0.023 mol) of Compound 1-3 prepared in Example 1-3 in a 250-mL, three-necked round bottom flask, 11.0 g of Compound 22-1 prepared in Example 22-1, and 0.03 palladium acetate (II) g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 90 mL were added. The reaction solution was refluxed for 2 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to give 11.6 g (75% yield) of compound 22 .

[Example 23] Preparation of compound 23

23-1. Preparation of compound 23-1

In a 500-mL, 3-neck round bottom flask, 9.8 g (0.058 mol) of compound (1,1`-biphenyl)-2-amine was added in a nitrogen atmosphere, and then diluted with 300 mL of toluene. To this diluent, 20.3 g of 2-(4-bromophenyl)-9,9-dimethyl-9 H -fluorene, tris(dibenzylideneacetone)dipalladium(0) 0.27 g, tri-(t-butyl)phos 0.12 g of pin and 7.2 g of sodium t-butoxide were added. The reaction solution was refluxed for 1 hour, cooled, and poured into an excess of methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and then separated by a column to obtain 18.8 g (yield 74%) of compound 23-1 .

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-necked round bottom flask, 11.0 g of Compound 23-1 prepared in Example 23-1, 0.03 palladium acetate (II) g, tri-(t-butyl)phosphine 0.05 g, sodium t-butoxide 2.8 g, and o -xylene 90 mL were added. The reaction solution was refluxed for 2 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 10.3 g (yield 67%) of compound 23 .

[Example 24] Preparation of Compound 24

In a 250-mL, 3-neck round bottom flask, 12.6 g of bis(6-phenyldibenzo[b,d]furan-4-yl)amine in 7.3 g (0.023 mol) of the compound 1-3 prepared in Example 1-3 , 0.03 g of palladium acetate (II), 0.05 g of tri-(t-butyl) phosphine, 2.8 g of sodium t-butoxide, and 70 mL of o -xylene were added. The reaction solution was refluxed for 5 hours, then cooled and poured into excess methanol to precipitate a solid. The obtained solid was filtered, dried in vacuo, and separated by a column to give 9.8 g (yield 58%) of compound 24 .

[Example 25]

After completely washing the substrate formed with a transparent anode of indium tin oxide (ITO) having a thickness of 1200 mm 2, the substrate was put into a vacuum deposition apparatus and then depressurized to about 10 ⁻⁷ torr. Subsequently, the following compound RHI was deposited to have a thickness of 50 MPa to form a hole injection layer. Subsequently, the hole transport layer was formed by depositing the compound 1 of the present invention to have a thickness of 800 MPa. Subsequently, the following compound RHT2 was deposited to have a thickness of 150 MPa 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 a light emitting layer having a thickness of 250Å. Subsequently, an electron transport layer 1 was formed by depositing the compound EET1 of the ELM product so that the thickness was 200 MPa. Subsequently, the electron transport layer 2 was formed by depositing the compound EET2 of ELM product to a thickness of 50Å. Subsequently, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 15 MPa. Finally, aluminum was deposited to a thickness of 2000 MPa to form a cathode. A light emission test was performed by applying a voltage to the organic electroluminescent device manufactured as described above. Table 1 shows the applied voltage, luminous efficiency, and luminous color measured at a luminance of 500 cd/m ² .

[Example 26]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 2 was used instead of Compound 1 as the hole transport layer.

[Example 27]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 3 was used instead of Compound 1 as the hole transport layer.

[Example 28]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 4 was used instead of Compound 1 as the hole transport layer.

[Example 29]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that compound 5 was used instead of compound 1 as the hole transport layer.

[Example 30]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 6 was used instead of Compound 1 as the hole transport layer.

[Example 31]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 8 was used instead of Compound 1 as the hole transport layer.

[Example 32]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 12 was used instead of Compound 1 as the hole transport layer.

[Example 33]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 13 was used instead of Compound 1 as the hole transport layer.

[Example 34]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 14 was used instead of Compound 1 as the hole transport layer.

[Example 35]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 15 was used instead of Compound 1 as the hole transport layer.

[Example 36]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 16 was used instead of Compound 1 as the hole transport layer.

[Example 37]

In Example 25, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 25, except that Compound 17 was used instead of Compound 1 as the hole transport layer.

[Example 38]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 18 was used instead of Compound 1 as the hole transport layer.

[Example 39]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that compound 19 was used instead of compound 1 as the hole transport layer.

[Example 40]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 22 was used instead of Compound 1 as the hole transport layer.

[Example 41]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that Compound 23 was used instead of Compound 1 as the hole transport layer.

[Example 42]

After completely washing the substrate formed with a transparent anode of indium tin oxide (ITO) having a thickness of 1200 mm 2, the substrate was put into a vacuum deposition apparatus and then depressurized to about 10 ⁻⁷ torr. Subsequently, the following compound RHI was deposited to have a thickness of 50 MPa to form a hole injection layer. Subsequently, the compound RHT1 was deposited to have a thickness of 800 MPa to form a hole transport layer. Subsequently, the compound 6 of the present invention was deposited to have 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 a light emitting layer having a thickness of 250Å. Subsequently, an electron transport layer 1 was formed by depositing the compound EET1 of the ELM product so that the thickness was 200 MPa. Subsequently, the electron transport layer 2 was formed by depositing the compound EET2 of ELM product to a thickness of 50Å. Subsequently, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 15 MPa. Finally, aluminum was deposited to a thickness of 2000 MPa to form a cathode. A light emission test was performed by applying a voltage to the organic electroluminescent device manufactured as described above. Table 1 shows the applied voltage, luminous efficiency, and luminous color measured at a luminance of 500 cd/m ² .

[Example 43]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that compound 7 was used instead of compound 6 as the electron blocking layer.

[Example 44]

In Example 42, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 42, except that compound 8 was used instead of compound 6 as the electron blocking layer.

[Example 45]

In Example 42, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 42, except that compound 9 was used instead of compound 6 as the electron blocking layer.

[Example 46]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that compound 10 was used instead of compound 6 as the electron blocking layer.

[Example 47]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that compound 11 was used instead of compound 6 as the electron blocking layer.

[Example 48]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that compound 15 was used instead of compound 6 as the electron blocking layer.

[Example 49]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that compound 19 was used instead of compound 6 as the electron blocking layer.

[Example 50]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that compound 20 was used instead of compound 6 as the electron blocking layer.

[Example 51]

In Example 42, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 42, except that compound 21 was used instead of compound 6 as the electron blocking layer.

[Example 52]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that compound 22 was used instead of compound 6 as the electron blocking layer.

[Example 53]

In Example 42, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 42, except that compound 24 was used instead of compound 6 as the electron blocking layer.

[Example 54]

In Example 42, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 42, except that Compound 2 was used instead of Compound RHT1 as the hole transport layer.

[Example 55]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that compound 3 was used instead of compound RHT1 as the hole transport layer.

[Example 56]

In Example 44, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 44, except that compound 3 was used instead of compound RHT1 as the hole transport layer.

[Example 57]

In Example 48, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 48, except that compound 14 was used instead of compound RHT1 as the hole transport layer.

[Comparative Example 1]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that the compound RHT1 was used instead of compound 1 as the hole transport layer.

[Comparative Example 2]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that the following compound EHT1 was used instead of compound 1 as the hole transport layer.

[Comparative Example 3]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that the following compound EHT2 was used instead of compound 1 as the hole transport layer.

[Comparative Example 4]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that the following compound EHT3 was used instead of compound 1 as the hole transport layer.

[Comparative Example 5]

In Example 25, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 25, except that the following compound EHT4 was used instead of compound 1 as the hole transport layer.

[Comparative Example 6]

In Example 42, an organic electroluminescent device was manufactured and evaluated in the same manner as in Example 42, except that the following compound EHT5 was used instead of compound 6 as the electron blocking layer.

[Comparative Example 7]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that the following compound EHT6 was used instead of compound 6 as the electron blocking layer.

[Comparative Example 8]

In Example 42, an organic electroluminescent device was fabricated and evaluated in the same manner as in Example 42, except that the following compound EHT7 was used instead of compound 6 as the electron blocking layer.

As described above, organic electroluminescent devices of Examples 25 to 57 and Comparative Examples 1 to 8 were manufactured using the compounds prepared according to Examples 1 to 24. The hole transport layer and electron blocking layer materials, driving voltage, luminous efficiency, and luminous color are summarized in Table 1 below.

Example Hole transport layer
material E-low layer
material Driving voltage
(V) Luminous efficiency
(cd/A) Luminous color Example 25 Compound 1 RHT2 4.4 6.9 blue Example 26 Compound 2 RHT2 4.2 7.3 blue Example 27 Compound 3 RHT2 3.8 8.0 blue Example 28 Compound 4 RHT2 4.2 7.5 blue Example 29 Compound 5 RHT2 3.9 7.7 blue Example 30 Compound 6 RHT2 4.5 7.5 blue Example 31 Compound 8 RHT2 4.5 7.2 blue Example 32 Compound 12 RHT2 4.5 6.9 blue Example 33 Compound 13 RHT2 4.3 7.2 blue Example 34 Compound 14 RHT2 4.0 7.4 blue Example 35 Compound 15 RHT2 4.2 7.1 blue Example 36 Compound 16 RHT2 4.2 7.2 blue Example 37 Compound 17 RHT2 4.3 7.4 blue Example 38 Compound 18 RHT2 4.2 7.1 blue Example 39 Compound 19 RHT2 4.1 7.2 blue Example 40 Compound 22 RHT2 4.3 7.0 blue Example 41 Compound 23 RHT2 4.5 7.1 blue Example 42 RHT1 Compound 6 3.9 7.8 blue Example 43 RHT1 Compound 7 4.1 7.3 blue Example 44 RHT1 Compound 8 4.1 7.6 blue Example 45 RHT1 Compound 9 4.3 7.5 blue Example 46 RHT1 Compound 10 4.2 7.4 blue Example 47 RHT1 Compound 11 4.0 7.6 blue Example 48 RHT1 Compound 15 4.3 7.6 blue Example 49 RHT1 Compound 19 4.2 7.5 blue Example 50 RHT1 Compound 20 4.2 7.0 blue Example 51 RHT1 Compound 21 4.1 7.3 blue Example 52 RHT1 Compound 22 4.5 7.8 blue Example 53 RHT1 Compound 24 4.4 7.5 blue Example 54 Compound 2 Compound 6 4.0 7.7 blue Example 55 Compound 3 Compound 6 3.8 8.0 blue Example 56 Compound 3 Compound 8 3.7 7.9 blue Example 57 Compound 14 Compound 15 3.7 8.0 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 can be seen from Table 1, it can be seen that the organic electroluminescent devices according to Examples 25 to 57 of the present invention have higher luminance and efficiency than Comparative Examples 1 to 8.

Specifically, all of the compounds 1 to 24 according to the above examples have a central structure consisting of indolocarbazole and an amine substituent, but compared to the other cases (Comparative Examples 1 to 8), the driving voltage is lower and the luminous efficiency Has a higher effect.

However, in the present invention, in formula II wherein L ₁ of formula I is a linker, R ₂ is a biphenyl group, a to c are 0, and R ₁ , X is CY ₂ (Y is a hydrogen atom), and d And when e is 0 (EHT4, Comparative Example 5), as a result of the confirmation, the driving voltage is high and the luminous efficiency is low, and thus, it is excluded from the present invention.

In addition, in the case where X is CY ₂ (Y is a hydrogen atom, an alkyl group, or an aryl group) in the formula II of the present invention (Compounds 1-5, 12-18, 22-23), when X is an oxygen atom, and a sulfur atom Compared to (Compounds 6 to 11, 19 to 21, and 24), it exhibited better luminous efficiency at a lower driving voltage overall.

Furthermore, the compound (compounds represented by Formula III, compounds 3, 5) in which X is CY ₂ (Y is a hydrogen atom, an alkyl group, or an aryl group) in Formula II was more effective when used as a hole transport layer, and Formula II Compounds in which X is an oxygen atom (compounds represented by Chemical Formula V, Compounds 6, 11) were more effective when used as an electron blocking layer.

In addition, in the case where R ₂ in the general formula (I) of the present invention is an aryl group (especially biphenyl) (Compounds 2 to 5), it exhibited more excellent luminous efficiency at a lower driving voltage overall than otherwise (Compound 1). .

In the above, the present invention has been shown and described in relation to certain preferred embodiments, but the present invention may be variously modified and changed within the scope of not departing from the technical features or field of the present invention provided by the following claims. It is obvious to one of ordinary skill in the art that it can be.

Claims (10)

Compounds represented by the following formula I:
[Formula I]

In Formula I, L ₁ is a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, or a linker,
R ₁ is one of the structures represented by Formula II below,
[Formula II]

(In the formula II, R ₁₁ and R ₁₂ are hydrogen atom, deuterium atom, halogen group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkyl group, substituted or unsubstituted An aryloxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted silyl group, or a cyano group,
X is an oxygen atom, a sulfur atom, CY ₂ (Y is a hydrogen atom, an alkyl group, or an aryl group),
d and e are integers of 0 to 4, and when 2 or more, the substituents in parentheses are the same or different,)
R ₂ to R ₅ 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 aryl group. 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 of 0 to 3, b and c are an integer of 0 to 4, and when a to c is 2 or more, the substituents in parentheses are the same or different.
The method of claim 1,
In Formula II, wherein L ₁ of Formula I is a linker, R ₂ is a biphenyl group, a to c are 0, and R ₁ , X is CY ₂ (Y is a hydrogen atom), and d and e are 0 Compound, characterized in that the case is excluded.
The method of claim 1,
A compound characterized in that it is used as a light emitting material for an organic light emitting diode (Organic Light Emitting Diode).
The method of claim 1,
Formula I is a compound, characterized in that the formula III, formula IV, or formula V:
[Formula III] [Formula IV] [Formula V]

In Formula III, Formula IV, and Formula V, R ₂ to R ₅ , R ₁₁ , and a to d are as defined in Formula I,
R ₆ and R ₇ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group.
The method of claim 1,
Formula I is a compound characterized in that the formula VI, formula VII, or formula VIII:
[Formula VI] [Formula VII] [Formula VIII]

In Formula VI, Formula VII, and Formula VIII, L ₁ , R ₁₁ , R ₃ to R ₅ , and a to c are as defined in Formula I.
The method of claim 1,
L ₁ is a compound, characterized in that the linker (linker).
The method of claim 1,
Formula I is a compound, characterized in that selected from the group consisting of the following compounds:

Comprising the compound according to any one of claims 1 to 7,
An organic electroluminescent composition, characterized in that it is used as a light emitting material for an organic electroluminescent device (Organic Light Emitting Diode).
Comprising the compound according to any one of claims 1 to 7,
An organic electroluminescent composition, characterized in that used for a hole transport layer or an electron blocking layer of an organic electroluminescent device (Organic Light Emitting Diode).
An organic electroluminescent device comprising at least one organic layer comprising the composition according to claim 8.

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