KR101552135B1 - Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof - Google Patents

Abstract

The present invention relates to a novel compound, an organic electric device using the organic compound, and an electronic device, and the present invention can improve the luminous efficiency, color purity and lifetime of the device, and lower the driving voltage.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device,

TECHNICAL FIELD [0001] The present invention relates to a compound, an organic electric device including the same, and an electronic device thereof.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

On the other hand, the diffusion of metal oxide from the anode electrode (ITO), which is one of the causes of shortening the lifetime of the organic electronic device, is delayed, and stable characteristics such as joule heating generated during driving the device, It is necessary to develop a hole injection layer material having a temperature. It is also reported that the low glass transition temperature of the hole transporting layer material significantly affects the lifetime of the device depending on the characteristics of the uniformity of the thin film surface collapsing during device operation. In addition, the deposition method is the mainstream in the formation of OLED devices, and a material that can withstand such a long time, that is, a material having high heat resistance characteristics, is required.

In order to sufficiently exhibit the excellent characteristics of the organic electroluminescent device described above, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material is supported by a stable and efficient material However, stable and efficient development of an organic material layer for an organic electric device has not yet been sufficiently developed, and therefore development of a new material is continuously required.

It is an object of the present invention to provide a compound capable of improving a high luminous efficiency, a low driving voltage, a high heat resistance, a color purity and a lifetime of the device, an organic electric device using the same, and an electronic device thereof.

In one aspect, the invention provides compounds represented by the formula:

In another aspect, the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.

By using the compound according to the present invention, it is possible to achieve a high luminous efficiency, a low driving voltage, and a high heat resistance of the device, and can greatly improve the color purity and lifetime of the device.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference symbols as possible even if they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

The term " halo "or" halogen "as used herein, on the other hand, includes fluorine, chlorine, bromine, and iodine unless otherwise specified.

The term "alkyl" or "alkyl group ", as used herein, unless otherwise specified, has from 1 to 60 carbon atoms, but is not limited thereto.

The term "alkenyl" or "alkynyl ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms,

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxy group" as used in the present invention has, unless otherwise stated, 1 to 60 carbon atoms, but is not limited thereto.

The terms "aryl group" and "arylene group ", as used in the present invention, each have 6 to 60 carbon atoms, but are not limited thereto.

In the present invention, an aryl group or an arylene group means an aromatic group having a single ring or a heterocyclic ring, and the neighboring substituent includes an aromatic ring formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirobifluorene group.

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 3 to 60 carbon atoms each containing at least one heteroatom, But includes a single ring as well as a heterocyclic ring and may be formed by bonding adjacent groups.

The term " heterocycloalkyl ", "heterocyclic group ", as used herein, unless otherwise indicated, includes one or more heteroatoms, has from 2 to 60 carbon atoms, , And neighboring groups may be combined with each other. Furthermore, the "heterocyclic group" may mean an alicyclic group and / or an aromatic group including a hetero atom.

As used herein, the term "heteroatom " refers to N, O, S, P and Si, unless otherwise indicated.

Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms and an "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise indicated, the term "saturated or unsaturated ring" as used herein refers to a saturated or unsaturated aliphatic ring or an aromatic ring or hetero ring having 6 to 60 carbon atoms.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention alkoxy group, C ₁ ~ C ₂₀ alkyl amine group of _20, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ arylalkenyl group, a silane group, a boron of Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a cyano group, a germanium group, and a C ₅ to C ₂₀ heterocyclic group, and is not limited to these substituents.

1 is an illustration of an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Having an organic compound layer containing a compound represented by the general formula (1). In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, the remaining layers except the light emitting layer 150 may not be formed. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to the present invention may further include a protective layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer may be used as a host or a dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, .

The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, and an electron transporting layer 160 and an electron injection layer 170, and then depositing a material usable as the cathode 180 on the organic layer.

In addition, the organic material layer can be formed using a variety of polymer materials by a solution process other than a vapor deposition process or a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, It can be made of a number of layers. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electroluminescent device according to the present invention may be of a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. The electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the compound according to one aspect of the present invention will be described.

A compound according to one aspect of the present invention is represented by the following formula (1).

In the above formula (1), A represents Represents a benzene ring condensed with two adjacent rings (a pentagonal ring substituted with R < ₁ >, R < ₂ > and D), and may be represented by the following formula (1a).

<Formula 1a>

In Formula 1, B represents a benzene ring condensed with two adjacent rings (D and E), and may be represented by Formula 1a.

In the above formula (1), D is a pentagon ring condensed with two adjacent rings (A and B) and may be represented by the following formula (1b).

&Lt; EMI ID =

In Formula 1, E is a pentagonal ring condensed with two adjacent rings (a benzene ring substituted with B and R ₇ to R ₁₀ ) and may be represented by the following Formula 1c.

&Lt; Formula 1c >

In the above formulas (1), (1a), (1b) and (1c)

(1) X and Y are each independently NR ', SiR'R ", CR'R" or S;

(2) R 'and R " may each independently be represented by one of the following formulas: wherein Z is C or N;

,

,

,

,

(3) Ar ₁ represents hydrogen, deuterium, tritium, a halogen group, a C ₁ to C ₂₀ alkyl group, a C ₁ to C ₂₀ alkoxy group, a C ₁ to C ₂₀ alkylamine group, a C ₁ to C ₂₀ alkyl A C ₂ to C ₂₀ alkenyl group, a C ₂ to C ₂₀ alkynyl group, a C ₃ to C ₂₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₂₀ arylamine group, a substituted or unsubstituted C ₆ to C ₂₀ arylthiophene group, alkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted with a heavy hydrogen aryl, C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron group, a heteroaryl of germanium group, a C ₂ ~ C ₂₀ an aryl group unsubstituted or substituted with a substituent selected from the group consisting of a ring C ₆ ~ C _60; Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and An acetylene group, a C ₂ to C ₆₀ heterocyclic group having at least one heteroatom selected from the group consisting of O, N, S, Si and P ; Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C arylalkyl group of _{8 ~ C 20, C 8 ~} C 20 aryl alkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, the in nitrile group and acetylene group the group consisting of unsubstituted or substituted with substituent C ₁ ~ C ₅₀ An alkyl group; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ a cycloalkyl group, C ₂ ~ C ₃₀ of the heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C substituted with a substituent selected from the ₆₀ group yirwojin group heterocyclic or unsubstituted C for ₆ ~ C ₆₀ aryl An amine group ; , &Lt; / RTI &gt;

(4) R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, deuterium, tritium, a halogen group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₆ to C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted with an aryl group, C ₇ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ aryl alkenyl group, C ₂ ~ C ₂₀ of the hetero ring group, nitrile group and acetylene group selected from the group consisting of substituted with a substituent or unsubstituted alkyl group of C ₁ ~ C _50; or Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ alkyl group of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ alkyl amine group of the C _20, C ₁ ~ alkyl thiophene group of C _20, C ₆ of ~ C ₂₀ aryl amine group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ of the aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, a C ₂ ~ C ₂₀ heterocyclic group selected from the group consisting of an aryl group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the substituents; , Which may combine with each other to form a spiro compound.

(5) R ₃ to R ₁₁ are each independently hydrogen; heavy hydrogen; Tritium; A halogen group ;

Hydrogen, deuterium, tritium, a halogen group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ aryl group, a C ₆ ~ C ₂₀ substituted with a heavy hydrogen of the aryl group, C arylalkyl group of _{7 ~ C 20, C 8 ~} C 20 aryl alkenyl group, C ₂ ~ C ₂₀ of the heterocyclic group, the in nitrile group and acetylene group the group consisting of unsubstituted or substituted with substituent C ₁ ~ C ₅₀ An alkyl group; Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₆ ~ C ₂₀ of the arylamine group, C ₆ ~ C ₆₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, C ₇ ~ heterocyclic group of C ₂₀ arylalkyl groups, C ₈ ~ C ₂₀ arylalkenyl group, C ₂ ~ C ₂₀ of the nitrile group and An acetylene group, a C ₂ to C ₆₀ heterocyclic group having at least one heteroatom selected from the group consisting of O, N, S, Si and P ; Hydrogen, deuterium, tritium, a halogen group, C ₁ ~ alkyl group of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ alkyl amine group of the C _20, C ₁ ~ alkyl thiophene group of C _20, C ₆ of ~ C ₂₀ aryl amine group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ of the aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, a C ₂ ~ C ₂₀ heterocyclic group selected from the group consisting of an aryl group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the substituents; A halogen atom, an amino group, a nitrile group, a nitro group, a C ₁ to C ₂₀ alkyl group, a C ₂ to C ₂₀ alkenyl group, a C ₁ to C ₂₀ alkoxy group, a C ₃ to C ₃₀ a cycloalkyl group, C ₂ ~ C ₃₀ of the heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₂ ~ C substituted with a substituent selected from the ₆₀ group yirwojin group heterocyclic or unsubstituted C for ₆ ~ C ₆₀ aryl An amine group ; , &Lt; / RTI &gt;

(6) n is an integer of 1 or 2, and m is an integer of 0 to 5.

Specifically, the compound represented by the formula (1) may be one of the following formulas (2) to (8).

In the above formulas,

A, B, R ', R ", R ₁ to R ₁₁ , n and m are the same as A, B, R', R", R ₁ to R ₁₁ , n and m defined in the above formula (1).

More specifically, the compound represented by Formula 1 may be one of the following Compounds 1-1 to 7-20.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

Synthesis of the compound was carried out as follows.

Product  1 Synthetic method example

<Reaction Scheme 1>

(One) Sub  Synthesis method of 1-2

Add Sub 1-1 compound, Nitric acid, and carbon tetrachloride to a round bottom flask, and proceed at 50 ℃. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallization.

Examples of Sub 1-1 are as follows, but are not limited thereto, and their FD-MSs are shown in Table 1 below.

(2) Sub  Synthetic method 1-4

The obtained Sub 1-2, Sub 1-3, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ were dissolved in a small amount of water with toluene and refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain the desired product.

(3) Sub  1

The obtained Sub 1-4 and triphenylphosphine were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired product.

Examples of Sub 1 are as follows but are not limited thereto, and their FD-MSs are shown in Table 2 below.

(4) Product  1

Sub 1 (1 eq.), Sub 6 (1.1 eq.), Pd ₂ (dba) ₃ (0.05 mol%), PPh ₃ (0.1 eq.), NaO t- Bu (3 eq.), Toluene / 1 mmol), and the reaction is allowed to proceed at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain Product 1.

Examples of Sub 6 are as follows but are not limited thereto, and FD-MSs of Sub 6-4 to Sub 6-14 are shown in Table 3 below.

(5) Example of compound synthesis

end. 1-71 Synthetic Example

<Reaction Scheme 2>

A round bottomed flask was charged with 15- (2,4-diphenylpyrimidin-5-yl) -13,13-dimethyl-13,15-dihydro-7H-indeno [1,2- b] indolo [2,3- Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 eq), NaO t- Bu (6 eq), toluene (10.5 mL / 1 mmol), bromobenzene ), And the reaction proceeds at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 8.6 g (yield: 63%) of final product.

I. 1-73 Synthetic examples

<Reaction Scheme 3>

A round bottom flask was charged with 13.13-dimethyl-15- (4-phenylquinazolin-2-yl) -13,15-dihydro-7H-indeno [1,2- b] indolo [2,3- , 20mmol), bromobenzene (3.8g, 24mmol), Pd 2 (dba) 3 (0.06 ~ 0.1 mmol), PPh 3 (0.2 equiv), NaO t -Bu (6 eq.), toluene (10.5 mL / 1 mmol) of And the reaction proceeds at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 8.5 g (yield: 65%) of final product.

All. 1-75 Synthetic Examples

<Reaction Scheme 4>

(12.3 g, 20 mmol), 4-bromo-1,1'-biphenyl (5.6 g, 24 mmol), Pd ₂ (dba) ₃ (0.06-0.1 mmol) and PPh ₃ (0.2 eq.), NaO t- Bu (6 eq.) And toluene (10.5 mL / 1 mmol). After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 8.9 g (yield: 58%) of final product.

la. 2-31 Synthetic Examples

<Reaction Scheme 5>

A round bottom flask was charged with 13,13-dimethyl-7,13-dihydrobenzo [4,5] thieno [2,3-g] indeno [1,2- b] carbazole (7.8 g, 20 mmol) Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 eq), NaO t- Bu (6 eq), toluene (10.5 mL / 1 mmol) ), And the reaction proceeds at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 6.9 g (yield: 55%) of final product.

hemp. 3-6 Synthetic Examples

<Reaction Scheme 6>

A round bottom flask was charged with 13,13,15,15-tetramethyl-14,15-dihydro-13H-diindeno [2,1-a: 1 ', 2'-i] carbazole (8.0 g, 20 mmol) Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 eq.), NaO t- Bu (6 eq.), Toluene (10.5 mL / 1 mmol), and the reaction is allowed to proceed at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.6 g (yield: 60%) of final product.

bar. 3-26 Synthetic Examples

<Reaction Scheme 7>

A round bottom flask was charged with 12,12,15,15-tetramethyl-12,15-dihydro-6H-diindeno [1,2-b: 2 ', 1'-h] carbazole (8.0 g, 20 mmol) Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 eq.), NaO t- Bu (6 eq.), Toluene (10.5 mL / 1 mmol), and the reaction is allowed to proceed at 100 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.4 g (yield: 59%) of final product.

four. 3-27 Synthetic Examples

<Reaction Scheme 8>

A solution of 12,12,15,15-tetramethyl-12,15-dihydro-6H-diindeno [1,2-b: 2 ', 1'-h] carbazole (8.0 g, 20 mmol), 4- After adding 2-phenylquinazoline (6.8 g, 24 mmol), Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 eq.), NaO t- Bu (6 eq.) And toluene (10.5 mL / The reaction proceeds at 100 占 폚. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.4 g (yield: 61%) of final product.

Ah. 3-40 Synthetic Example

<Reaction Scheme 9>

A round bottom flask was charged with 12,12,15,15-tetramethyl-12,15-dihydro-6H-diindeno [1,2-b: 2 ', 1'-h] carbazole (8.0 g, 20 mmol) Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 eq), NaO t- Bu (6 eq) and toluene (10.5 mL / 1 mmol) And the reaction proceeds at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.8 g (yield: 62%) of the final product.

Product  2 Synthetic method example

<Reaction formula 10>

(One) Sub  2-2 synthesis

2-boronobenzoic acid, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ substituted with Sub 2-1 (1 equivalent), R ₃ to R ₆ were added to a 1000 mL 2-necked round bottom flask and water was added with tetrahydrofuran After charging with nitrogen, the mixture is stirred at 80 DEG C for 12 hours. When the reaction is completed, the reaction solution is cooled to room temperature and extracted with dichloromethane. The organic solvent layer is removed using MgSO _4, and the solvent is removed by drying under reduced pressure. The obtained reaction product was recrystallized using ethanol to obtain Sub 2-2.

(2) Sub  Synthesis method of 2-3

Add Sub 2-2, chlorobenzene and PPA to a 500 mL 2-neck round bottom flask, and stir at room temperature for 12 hours. 100 ml of water is added to the reaction mixture, which is stirred for 10 minutes, and then the organic layer and the water layer are separated. After extracting with n-hexane, the water of the organic solvent layer is removed using MgSO ₄ , and the solvent is removed by drying under reduced pressure. The crude product thus obtained was separated and purified by silica gel column chromatography using n-hexane to obtain Sub 2-3.

(3) Sub  2-4 Synthesis method

Sub 2-3 in a 250 mL 2-neck round bottom flask and dissolve in THF solvent. The reaction temperature was lowered to -78 ° C and 2.5 M n-BuLi was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was cooled to -78 ° C again, and R ₁ and R ₂ substituted with iodo were added thereto, followed by further stirring at room temperature for 3 hours. After the reaction was completed, 20 mL of water was added, and the mixture was extracted with diethyl ether. The resulting extract was dried over MgSO _{4 and} then dried under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using ethyl acetate and n-hexane to obtain Sub 2-4.

(4) Sub  Synthesis method of 2-5

Add Sub 2-4 compound, Nitric acid, and carbon tetrachloride to a round bottom flask and proceed at 50 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallization.

(5) Sub  2-7 synthesis method

The obtained Sub 2-5, Sub 2-6, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ were dissolved in a small amount of water with toluene and refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain the desired product.

(6) Sub  2 synthesis method

The resulting Sub 2-7 and triphenylphosphine were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by column chromatography to obtain the desired product.

Examples of Sub 2 include, but are not limited to, the following FD-MSs.

(7) Product  2 synthesis method

Sub 2 (1 eq.), Sub 6 (1.1 eq.), Pd ₂ (dba) ₃ (0.05 mol%), PPh ₃ (0.1 eq.), NaO t- Bu (3 eq.), Toluene / 1 mmol), and the reaction is allowed to proceed at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain Product 2.

(8) Example of compound synthesis

end. 4-31 Synthetic Example

<Reaction Scheme 11>

A round bottom flask was charged with 13,13-dimethyl-13,15-dihydrofluoreno [2 ', 3': 4,5] thieno [3,2-a] carbazole (7.8 g, 20 mmol) 4,6-diphenylpyrimidine (7.7g, 24mmol) , Pd 2 (dba) 3 (0.06 ~ 0.1 mmol), PPh 3 (0.2 equiv), NaO t -Bu (6 eq.), toluene (10.5 mL / 1 mmol) of And the reaction proceeds at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.6 g (yield: 60%) of final product.

Product  3 Example of synthesis

<Reaction Scheme 12>

(One) Sub  Synthesis of 3-1

2-boronobenzoic acid, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ substituted with Sub 2-4 (1 equivalent), R ₇ to R ₁₀ were added to a 1000 mL 2-necked round bottom flask and water and tetrahydrofuran After charging with nitrogen, the mixture is stirred at 80 DEG C for 12 hours. When the reaction is completed, the reaction solution is cooled to room temperature and extracted with dichloromethane. The organic solvent layer is removed using MgSO _4, and the solvent is removed by drying under reduced pressure. The obtained reaction product was recrystallized using ethanol to obtain Sub 3-1.

(2) Sub  Synthesis method of 3-2

Add Sub 3-1, chlorobenzene and PPA to a 500 mL 2-necked round bottom flask, and stir at room temperature for 12 hours. 100 ml of water is added to the reaction mixture, which is stirred for 10 minutes, and then the organic layer and the water layer are separated. After extracting with n-hexane, the water of the organic solvent layer is removed using MgSO ₄ , and the solvent is removed by drying under reduced pressure. The crude product thus obtained was separated and purified by silica gel column chromatography using n-hexane to obtain Sub 3-2.

Examples of Sub 3-2 are as follows, but the present invention is not limited thereto, and their FD-MSs are shown in Table 5 below.

(3) Product  3 synthesis method

Add Sub 3-2 to a 250 mL 2-necked round bottom flask and dissolve in THF solvent. The reaction temperature was lowered to -78 ° C and 2.5 M n-BuLi was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was cooled to -78 ° C again, and R 'and R "substituted with iodo were added thereto, followed by further stirring at room temperature for 3 hours. After the reaction was completed, 20 mL of water was added, and the mixture was extracted with diethyl ether. The resulting extract was dried over MgSO _{4, and} then dried under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using ethyl acetate and n-hexane to obtain Product 3.

(4) Synthetic Example of Compound

end. 5-13 Synthetic examples

<Reaction Scheme 13>

To a 250 mL 2-necked round bottom flask was added 15,15-dimethyl-N, N-diphenyl-8,15-dihydrodifluoreno [1,2-b: 2 ', 3'-d] thiophen- ) Is dissolved in THF as a solvent. The reaction temperature was lowered to -78 ° C and 2.5 M n-BuLi was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was again cooled to -78 ° C, iodomethane (5.7 g, 40 mmol) was added thereto, and the mixture was further stirred at room temperature for 3 hours. After the reaction was completed, 20 mL of water was added, and the mixture was extracted with diethyl ether. The obtained extract was dried over MgSO ₄ and dried under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography using ethyl acetate and n-hexane to obtain 10.0 g (yield: 86%) of the final product.

Product  4 Example of synthesis method

<Reaction Scheme 14>

(One) Sub  4-1 Synthesis method

Add Sub 1-1 (1 equivalent), Br-substituted 2-boronobenzoic acid, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ to a 1000 mL 2-necked round bottom flask and add water with tetrahydrofuran. Followed by stirring at 80 DEG C for 12 hours. When the reaction is completed, the reaction solution is cooled to room temperature and extracted with dichloromethane. The organic solvent layer is removed using MgSO _4, and the solvent is removed by drying under reduced pressure. The obtained reaction product was recrystallized using ethanol to obtain Sub 4-1.

(2) Sub  4-2 Synthesis method

Add Sub 4-1, chlorobenzene and PPA to a 500 mL 2-neck round bottom flask, and stir at room temperature for 12 hours. 100 ml of water is added to the reaction mixture, which is stirred for 10 minutes, and then the organic layer and the water layer are separated. After extracting with n-hexane, the water of the organic solvent layer is removed using MgSO ₄ , and the solvent is removed by drying under reduced pressure. The crude product thus obtained was separated and purified by silica gel column chromatography using n-hexane to obtain Sub 4-2.

(3) Sub  Synthesis of 4-3

Add Sub 4-2 to a 250 mL 2-necked round bottom flask and dissolve in THF solvent. The reaction temperature was lowered to -78 ° C and 2.5 M n-BuLi was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was cooled to -78 ° C again, and R 'and R "substituted with iodo were added thereto, followed by further stirring at room temperature for 3 hours. After the reaction was completed, 20 mL of water was added, and the mixture was extracted with diethyl ether. The obtained extract was dried with MgSO ₄ and dried under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using ethyl acetate and n-hexane to obtain Sub 4-3.

(4) Sub  4-4 Synthesis method

Add Sub 4-3 compound, Nitric acid, and carbon tetrachloride to a round bottom flask and proceed at 50 ° C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was purified by silicagel column and recrystallization.

(5) Sub  Synthesis method of 4-5

The resulting Sub 4-4, Sub 2-6, Pd (PPh ₃ ) ₄ and K ₂ CO ₃ were dissolved in a small amount of water with toluene and refluxed for 24 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain the desired product.

(6) Sub  4 synthesis method

The resulting Sub 4-5 and triphenylphosphine were dissolved in o-dichlorobenzene and refluxed for 24 hours. When the reaction is completed, the solvent is removed by distillation under reduced pressure, and the concentrated product is separated by column chromatography to obtain the desired product

Examples of Sub 4 include, but are not limited to, the following FD-MSs.

(7) Product  4 synthesis method

Pd ₂ (dba) ₃ (0.05 mol%), PPh ₃ (0.1 eq.), NaO t- Bu (3 eq.), Toluene (10.5 mL) / 1 mmol), and the reaction is allowed to proceed at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic matter was purified by silicagel column and recrystallized to obtain Product 4.

(8) Example of compound synthesis

end. 6-15 Synthetic Example

<Reaction Scheme 15>

3-phenyl-6,8-dihydro-5H-benzo [6,7] -as-indaceno [2,3- b] carbazole (9.5 g, 20 mmol) in a round bottom flask, , Pd ₂ (dba) ₃ (0.06-0.1 mmol), PPh ₃ (0.2 eq.), NaO t- Bu (6 eq.) and toluene (10.5 mL / 1 mmol) Lt; 0 &gt; C. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO ₄ and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 7.0 g (yield: 63%) of final product.

Product  5 Synthetic method example

<Reaction Scheme 16>

(One) Sub  5-1 Synthetic method

Tetrakis (triphenylphophine) palladium (0) and potassium carbonate were added to 2- (methylthio) phenyl boronic acid substituted with Sub 4-3 and R ₇ to R ₁₀ and THF (tetrahydrofuran) and water (3: 1), and the mixture is stirred at 70 ° C. After the reaction was completed, the reaction mixture was extracted with CH ₂ Cl ₂ , wiped with water, and a small amount of water was removed with anhydrous MgSO _4. After filtration under reduced pressure, the organic solvent was concentrated and the resulting product was recrystallized using CH ₂ Cl ₂ and hexane The desired Sub 5-1 was obtained.

(2) Sub  5-2 Synthetic method

Sub 5-1 is dissolved in acetic acid and the hydrogen peroxide is dissolved in acetic acid. The mixture is dropped dropwise and stirred at room temperature for 6 hours. When the reaction was completed, acetic acid was removed using a pressure reducing apparatus and column chromatography was performed to obtain the desired Sub 5-2.

Examples of Sub 5-2 are as follows but are not limited thereto, and their FD-MSs are shown in Table 7 below.

(3) Product  5 Synthetic method

The obtained Sub 5-2 and trifluoromethanesulfonic acid are added and stirred at room temperature for 24 hours. Then, water and pyridine (8: 1) (pyridine (8: 1)) are slowly added and refluxed for 30 minutes. The temperature is lowered, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO ₄ , filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain the desired product 5.

(4) Synthetic Example of Compound

end. 7-20 Synthetic Examples

<Reaction Scheme 17>

11,11-dimethyl-3- (3- (methylsulfinyl) - [1,1'-biphenyl] -4-yl) -12,12-diphenyl-11,12- dihydroindeno [2,1- , 20 mmol) and trifluoromethanesulfonic acid. The mixture is stirred at room temperature for 24 hours, then water and pyridine (8: 1) (pyridine (8: 1)) are slowly added and refluxed for 30 minutes. The temperature is lowered, extracted with CH ₂ Cl ₂ and wiped with water. A small amount of water was removed with anhydrous MgSO _4. After filtration under reduced pressure, the organic solvent was concentrated, and the resulting product was separated by column chromatography to obtain 11.0 g (yield: 89%) of desired final product.

The FD-MS of the exemplary compounds of the above Compounds 1-1 to 7-20 are shown in Table 8 below.

In the meantime, although an exemplary synthesis example of the present invention represented by the general formula (1) has been described above, they are all based on the Suzuki cross-coupling reaction and the Buchwald-Hartwig cross coupling reaction. In addition to the substituents specified in the specific synthesis example, Even if the substituent is bonded, it does not affect the progress of the reaction. For example, in the reaction formula 1, "Sub 1-2 + Sub 1-3 → Sub 1-4", "Sub 2-1 → Sub 2-2", "Sub 2-5 + Sub 2-6 → Sub 2" Sub 4-4 → Sub 3-1 "in Reaction Formula 12," Sub 1-1 - 4 → Sub 4-1 "," Sub 4-4 → Sub 4-5 "in Reaction Formula 14, Sub 4 - 3 → Sub 5 - 1 "are all based on the Suzuki cross-coupling reaction and are represented as" Sub 1 + Sub 6 → Product 1 "in Scheme 1," Reaction 2 " + Sub 6 → Product 2 ", Reaction 11," Sub 4 + Sub 6 → Product 4 "in Scheme 14, and Reaction 15 are all based on the Buchwald-Hartwig cross coupling reaction, The above reactions will proceed.

Manufacture of organic electronic devices

An organic electroluminescent device was fabricated according to a conventional method using a compound obtained through synthesis as a luminescent host material or a luminescent auxiliary layer material of a luminescent layer.

First, a film of copper phthalocyanine (hereinafter referred to as &quot; CuPc &quot;) was vacuum deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer having a thickness of 10 nm. Subsequently, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vapor-deposited as a hole transport compound on the film to a thickness of 30 nm to form a hole transport layer . After forming the hole transporting layer, the compounds (1-1 to 1-90, 2-1 to 2-60, 3-1 to 3-60, 4-1 to 4-60, 5-1 to 5- 20, 6-1 to 6-60, 7-1 to 7-20) as a phosphorescent host material to form a light-emitting layer, tris (2-phenylpyridine) iridium (hereinafter referred to as Ir (ppy) ₃ ) was added. At this time, the concentration of Ir (ppy) _{3 in} the light emitting layer was 5 wt%, and vacuum deposition was performed to a thickness of 30 nm to form a light emitting layer. (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, and electron injection Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm. Thereafter, an organic electroluminescent device was prepared by depositing LiF, an alkali metal halide as an electron injecting layer, to a thickness of 0.2 nm, followed by depositing Al to a thickness of 150 nm and using this Al / LiF as a cathode.

&Lt; Comparative Example 1 &

An organic electroluminescent device was prepared in the same manner as in Example 6, except that Comparative Compound 1 (CBP) was used instead of the compound of the present invention as a luminescent host material.

&Lt; Comparative Compound 1: CBP >

&Lt; Comparative Example 2 &

An organic electroluminescent device was prepared in the same manner as in Example 6, except that Comparative Compound 2 was used instead of the compound of the present invention as a luminescent host material.

&Lt; Comparative Compound 2 >

&Lt; Comparative Example 3 &

An organic electroluminescent device was prepared in the same manner as in Example 6 except that Comparative Compound 3 was used instead of the compound of the present invention as a luminescent host material.

&Lt; Comparative Compound 3 >

A forward bias DC voltage was applied to the organic electroluminescent devices of Example 6 and Comparative Example 1, Comparative Example 2 and Comparative Example 3 prepared above, and electroluminescence (EL) characteristics were measured with a photoresearch PR-650 And the T90 lifetime was measured by a lifetime measuring device manufactured by Mac Science Co. at a luminance of 300 cd / m 2. Current density, luminance, luminous efficiency, lifetime, and color purity of the organic electroluminescent device manufactured according to Example 6, Comparative Example 1, Comparative Example 2 and Comparative Example 3 were measured, It was the same.

As can be seen from the results of Table 9, the organic electroluminescent device using the organic electroluminescent device material of the present invention was used as a light emitting layer material, and the driving voltage was higher than that of Comparative Example 1 (CPB), Comparative Example 2 and Comparative Example 3 Not only the luminous efficiency was improved but also the color purity and lifetime were remarkably improved. In other words, it can be seen that Compounds 1, 2 and 3 having CBP, carbazole, and O atom hetero ring as core significantly improve the efficiency and lifetime of the compounds of the present invention. The compound according to the present invention can be applied not only to an organic electroluminescent device (OLED) but also to a display device, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT) Can also be used. In addition, the same effects can be obtained even when the compounds of the present invention are used in other organic layers of an organic electroluminescent device, for example, a hole injection layer, an emission auxiliary layer, an electron injection layer, and an electron transport layer.

On the ITO layer (anode) formed on the glass substrate, a copper phthalocyanine (hereinafter referred to as CuPc) film was vacuum deposited as a hole injection layer to form a 40 nm thick film. Subsequently, 4,4-bis [ N - (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPD) was vapor-deposited as a hole transport compound on the film to a thickness of 20 nm, . Subsequently, the compound (1-71, 1-73, 1-75, 2-31, 3-6, 3-27, 4-31, 5-13, 6-15, 7- 20) was vacuum-deposited to a thickness of 20 nm to form an emission assist layer. CBP [4,4'-N, N'-dicarbazole-biphenyl] as a host and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] as a dopant are formed on the light- Was doped at a weight ratio of 95: 5 to deposit a light emitting layer with a thickness of 30 nm on the light emitting auxiliary layer. (2-methyl-8-quinolinolato) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer to form an electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm. Then, LiF, an alkali metal halide serving as an electron injecting layer, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to form an organic electroluminescent device.

&Lt; Comparative Example 4 &

An organic electroluminescent device was fabricated in the same manner as in Example 7, except that the light emitting auxiliary layer was omitted. That is, an organic electroluminescent device was prepared in the same manner as in Example 7, except that no luminescent auxiliary layer was formed.

&Lt; Comparative Example 5 &

An organic electroluminescent device was fabricated in the same manner as in Example 7, except that the compound of the present invention was used instead of the compound of the present invention to form a light-emitting auxiliary layer.

Electroluminescence (EL) characteristics of the organic electroluminescence devices of Example 7, Comparative Example 4 and Comparative Example 5 thus prepared were measured by applying a forward bias DC voltage to PR-650 of a photoresearch company, Measurement results The T90 lifetime was measured at a luminance of 300 cd / m 2 through a life measuring device manufactured by Mac Science. Current density, luminance, luminescence efficiency, lifetime and color purity of the organic electroluminescent device manufactured according to Example 7, Comparative Example 4 and Comparative Example 5 were measured.

As can be seen from the results of Table 10, the organic electroluminescent device using the organic electroluminescent device material of the present invention was used as a light emitting auxiliary layer material, and Comparative Example 4 in which the light emitting auxiliary layer was not used, The driving voltage was lower and the luminous efficiency was improved, as well as the color purity and lifetime were remarkably improved as compared with Comparative Example 5 used as the layer material. This is because when the compound of the present invention is used alone as a light emitting auxiliary layer, it has a high T1 energy level and improves the low voltage, the high luminous efficiency and the device lifetime of the organic electroluminescent device due to the deep HOMO energy level. The compound according to the present invention can be applied not only to an organic electroluminescent device (OLED) but also to a display device, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT) Can also be used. The same effects can be obtained even when the compounds of the present invention are used in other organic layers of an organic electroluminescent device, for example, a hole injecting layer, a light emitting layer, an electron injecting layer, and an electron transporting layer.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the claims, and all the techniques within the scope of the same should be interpreted as being included in the scope of the present invention.

Claims (8)

delete A compound represented by the formula:

In the above formulas,
A and B are

Lt;
S ring is a C ₄ ring including S,
C ring is a C ₅ ring,
R 'and R "are, independently of each other, a methyl group or a phenyl group,
R ₁ and R ₂ are independently of each other an unsubstituted C ₁ -C ₆ alkyl group; Or an unsubstituted C ₆ -C ₂₀ aryl group,
R ₃ to R ₆ are hydrogen; Or an unsubstituted C ₁ -C ₆ alkyl group,
R ₇ to R ₁₀ are hydrogen; Or an aryl group of C ₆ substituted or unsubstituted C ₆ -C ₂₀ aryl amines -C _20; and,
R ₁₁ is hydrogen; and n is 2. A compound characterized by being one of the following compounds:

. An organic electroluminescent device comprising a sequentially stacked first electrode, at least one organic layer containing a compound of any one of claims 2 and 3, and a second electrode. 5. The method of claim 4,
Wherein said compound is formed into said organic material layer by a solution process. 5. The method of claim 4,
Wherein the organic material layer includes at least one of a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, a hole injecting layer, an electron injecting layer, and an electron transporting layer. A display device including the organic electroluminescent device of claim 4; And
A controller for driving the display device; &Lt; / RTI &gt; 8. The method of claim 7,
Wherein the organic electronic device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

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