KR101393847B1 - Organosilane Compounds, Synthetic Method of Electroluminiscent Materials Thereby and Organic Electroluminiscent Device - Google Patents

Abstract

The present invention provides an organosilane compound represented by the formula (1), which is an intermediate useful in synthesizing an organic electroluminescence material, and a method for producing the organic electroluminescence material at a high yield and a low cost by using the same.

[Chemical Formula 1]

Organic electroluminescent device, organic electroluminescent material, organosilane derivative

Description

TECHNICAL FIELD The present invention relates to an organosilane compound, a method for producing the same, an organic electroluminescent material using the same, and an organic electroluminescent device,

FIG. 1 illustrates a structure of an organic electroluminescent device according to an embodiment of the present invention. FIG.

2 is an NMR chart of the organosilane compound 1 according to an embodiment of the present invention,

3 is a graph showing the color purity of the emission spectrum measured at 50 mA / cm 2 by applying the organic electroluminescence material compound 1-1 according to an embodiment of the present invention to an organic electroluminescence device,

4 shows electroluminescence spectra measured at 10 mA / cm 2, 50 mA / cm 2, and 100 mA / cm 2, respectively, by applying the organic electroluminescent material 1-1 according to an embodiment of the present invention to an organic electroluminescent device .

BRIEF DESCRIPTION OF THE DRAWINGS FIG.

1: substrate 2: anode

3: Hole injection layer 4: Hole transport layer

5: luminescent layer 6: electron transport layer

7: cathode 8: power source

The present invention relates to an organosilane compound which is particularly useful as an intermediate of an organic electroluminescent material, a method for producing an organic electroluminescent material using the same, and an organic electroluminescent device.

The most widely used liquid crystal display (LCD) is a non-light emitting type display device which consumes less power and is light, but the device driving system is complicated and response time and contrast characteristics are not satisfactory. Therefore, research on an organic electroluminescent device, which has recently attracted attention as a next generation flat panel display, has been actively conducted. The organic electroluminescent device is a self-luminous type device having many advantages such as brightness, driving voltage, response speed, etc. and has no viewing angle dependency compared to a liquid crystal display.

The emission mechanism of the organic electroluminescent device will be described below. Holes injected from a positive electrode into a valance band or a HILO of a Hole Injection Layer (HIL) proceed through an HIL (Emitting Layer) through a Hole Transporting Layer (HTL) At the same time, electrons move from the cathode to the light emitting layer through the electron injection layer to form an exciton. This exciton emits light as it falls to the ground state.

Eastman Kodak Company, in 1987, using the principle of the organic electroluminescent device as described above, developed TPD (N-N'-DiphenyI-N'-bis- (methylphenyl- 4,4'-diamine) as a light emitting layer was developed using Alq3 (tris (8-hydroxy-quinoline) aluminum complex).

Blue is doped with a blue dopant to a blue host and Alq3 is used as an electron transport layer (ETL), and Alq3 may be omitted depending on the characteristics of a blue host.

Further, a blue light emitting element using an anthracene compound derivative such as a diphenylanthracene structure is known.

In the case of constituting a display device using an organic electroluminescent device, it is one of the most important problems to secure long life and reliability of the organic electroluminescent device.

However, such conventional anthracene derivatives are not excellent in film forming workability and are not excellent in heat resistance because they are not easily formed into uniform thin films, and aggregation between molecules occurs during deposition due to the plate-like structure, resulting in high efficiency and high quality There is a problem in that it can not emit light.

In order to develop an organic electroluminescent material with higher performance, it is necessary to develop a basic structure that is essential for improving the light emission performance and to develop a specific functional group capable of significantly increasing the performance in combination with the basic structure. The manufacturing method is simple, and it must be possible to perform at low cost. However, since the organic electroluminescent material has a large number of bonds between aromatic hydrocarbons in structure, it is difficult to produce an excellent luminescent material.

The present inventors have developed an organosilane-based basic structure that contributes to improvement in light emitting performance and provide a simple and inexpensive method of combining various functional groups with the basic structure.

It is an object of the present invention to provide an organosilane intermediate which can be used for the production of organic electroluminescent materials and the like.

It is another object of the present invention to provide an organic electroluminescent material using the organosilane intermediate and an organic electroluminescent device comprising the organic electroluminescent material produced therefrom.

These and other objects of the present invention can be achieved by the present invention which is described in detail below.

According to an aspect of the present invention,

There is provided an organosilane compound represented by the following formula (1).

[Chemical Formula 1]

(Wherein Ar 1, Ar 2, and Ar 3 are each selected from the group consisting of an aryl group having 6 to 20 carbon atoms in which a part or all of hydrogen is substituted or unsubstituted with a substituent, L 1 is a single bond or a part or all of hydrogen is a substituent Or an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with < RTI ID = 0.0 >

,

,

와 같은 보론 유도체기를 포함한다.)Ar 4 is selected from one or more of C 6 to C 30 aryl groups in which a part or all of hydrogen is substituted or unsubstituted with a substituent, and at least one halogen group capable of Suzuki coupling reaction (aryl-aryl coupling)

,

,

≪ / RTI > and the like).

Also, the present invention provides the organosilane compound wherein L 1 is selected from the following formulas (2) to (9).

(In the formulas (2) to (9), the above-mentioned formulas may have a substituent at one or more hydrogen positions, and the substituents may be independently selected from the group consisting of a halogen atom (fluorine, chlorine, bromine, iodine), a nitro group, , A cycloalkyl group having 6 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heteroaryl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cyano group, a trifluoromethyl group, Are drawn through all the rings constituting the polycyclic ring, but this means that the bonding position of L1 and Ar4 may be any position in the polycyclic ring.

Ar 1, Ar 2, Ar 3 and Ar 4 are independent of one another and are selected from the following formulas (10) to (20).

(In the formulas (10) to (20), the above-mentioned formulas may have a substituent at one or more hydrogen positions, and the substituents may be independently selected from the group consisting of a halogen atom (fluorine, chlorine, bromine, iodine), a nitro group, , A cycloalkyl group having 6 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heteroaryl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cyano group, a trifluoromethyl group, Are drawn through all the rings constituting the polycyclic ring, but this means that the bonding position of L1 and Ar4 may be any position in the polycyclic ring.

In addition, the formula (1) provides an organosilane compound represented by the following formula (1) to (32).

The present invention also provides a method for producing the organosilane compound or a precursor thereof by the following representative reaction formula.

[Representative reaction formula]

,

,

와 같은 보론 유도체기가 없는 것을 제외하고는 동일하며, 상기 X1, X2는 하나가 할로겐이면 다른 하나는 스즈키 커플링 반응이 가능한

,

,

와 같은 보론 유도체기이다.)Ar5 is the same as the above-mentioned Ar4, or a halogen group capable of undergoing a Suzuki coupling reaction (aryl-aryl coupling) in Ar4,

,

,

And X1 and X2 are a halogen atom and the other is a Suzuki coupling reaction.

,

,

Is a boron derivative group.

The present invention also relates to a process for producing an organosilane compound, which comprises reacting the organosilane compound with an aryl group having 6 to 30 carbon atoms in which a Suzuki coupling reaction is present (unsaturated aliphatic group may be included in the structure and a part of hydrogen may be substituted with a substituent) And then reacting the organic electroluminescence material with the organic electroluminescence material.

The present invention also provides an organic electroluminescent device comprising a cathode and a plurality of organic compound layers including a light emitting layer positioned between the anode and the cathode, wherein the organic electroluminescent material produced by the above- Or a part of the organic electroluminescent device.

Hereinafter, the present invention will be described in more detail. The following detailed description is provided to illustrate the present invention by way of example only, and thus the present invention is not limited thereto.

The present invention provides a compound represented by the following general formula (1). The compound represented by the following formula (1) can be usefully used as a precursor of an organic electroluminescent material.

[Chemical Formula 1]

In the general formula (1), Ar 1, Ar 2, and Ar 3 are each selected from the group consisting of aryl groups having 6 to 20 carbon atoms in which part or all of hydrogen is substituted or unsubstituted.

L1 is a single bond or an aryl group having 6 to 30 carbon atoms in which part or all of hydrogen is substituted or unsubstituted with a substituent.

,

,

와 같은 보론 유도체기를 포함한다.Ar 4 is selected from one or more of C 6 to C 30 aryl groups in which a part or all of hydrogen is substituted or unsubstituted with a substituent, and at least one halogen group capable of Suzuki coupling reaction (aryl-aryl coupling)

,

,

≪ / RTI > and the like.

Although not limited, it is preferred that L1 is selected from the following formulas (2) to (9). More preferably an anthracene, a naphthalene or a phenyl group.

In the general formulas (2) to (9), the above-mentioned formulas may have a substituent at one or more hydrogen positions, and the substituents are independently selected from the group consisting of a halogen atom (fluorine, chlorine, bromine, iodine), a nitro group, May be selected from the group consisting of a cycloalkyl group having 6 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heteroaryl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cyano group, and a trifluoromethyl group .

The solid lines indicating the bonding positions are drawn through all the rings constituting the polycyclic ring, but this means that the bonding position of L1 and Ar4 may be any position in the polycyclic ring.

Ar1, Ar2, Ar3 and Ar4 are independent of each other and can be selected from the following formulas (10) to (20).

In the general formulas (10) to (20), the above-mentioned formulas may have a substituent at one or more hydrogen positions, and the substituents are independently selected from the group consisting of a halogen atom (fluorine, chlorine, bromine, iodine), a nitro group, A cycloalkyl group having 6 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heteroaryl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cyano group, and a trifluoromethyl group.

The solid lines indicating the bonding positions are drawn through all the rings constituting the polycyclic ring, but this means that the bonding position of L1 and Ar4 may be any position in the polycyclic ring.

The present invention also provides a process for preparing an organosilane compound or a precursor thereof by the following representative reaction formula.

[Representative reaction formula]

,

,

와 같은 보론 유도체기가 없는 것을 제외하고는 동일하며, 상기 X1, X2는 하나가 할로겐이면 다른 하나는 스즈키 커플링 반응이 가능한

,

,

와 같은 보론 유도체기이다. In the above formula, Ar1, Ar2 and Ar3 are as defined above, Ar5 is a halogen group which can be the same as the above-mentioned Ar4 or can undergo a Suzuki coupling reaction (aryl-aryl coupling)

,

,

And X1 and X2 are a halogen atom and the other is a Suzuki coupling reaction.

,

,

Lt; / RTI >

When Ar5 is the same as Ar4, the organosilane compound of formula (1) can be immediately obtained by the above reaction formula. When Ar5 is absent, the halogen group can be introduced through the halogenation reaction after the reaction, The organosilane compound of Formula 1 can be obtained by substituting a halogen group with a boron derivative group.

The precursor can be synthesized under mild conditions. In particular, after the completion of the reaction, the work-up is not purified through a column in a work-up process. Instead, the precursor is extracted with an organic solvent, It is obtained as a solid and can be easily obtained through filtration. If desired, a more pure precursor may be obtained by recrystallization.

As a method for realizing the above reaction formula, a Suzuki coupling reaction is typically used, and the reaction conditions thereof are well known in the art, and a detailed description thereof will be omitted.

Specifically, the precursor and the production method of the formula (1) will be described below.

As an example of the production method of the above formula (1), the following synthesis method can be mentioned, but this is not limitative because it is an example.

                                                        A

[Reaction Scheme 1]

For synthesis of a compound represented by the general formula (A) in Scheme 1, a dihalogen aryl compound may be prepared by using n-butyllithium in an organic solvent such as anhydrous tetrahydrofuran or anhydrous diethyl ether as a typical low-temperature lithium reaction, At a temperature ranging from 0 ° C to room temperature. However, the production method is not limited to the above reaction formula.

           A B

[Reaction Scheme 2]

)을 포함하는 화합물을 합성을 위한 방법으로, 할로겐 그룹(브롬, 요오드 등)을 포함하는 A 화합물 1당량을 무수 테트라하이드로퓨란 등과 같은 유기용매 하에서 저온 리튬반응으로 섭씨 -30도 내지 -75도 온도범위에서 리튬화 반응 후 트리메틸보레이트를 1 내지 5당량 투입하고 상온에서 2 내지 24시간 반응하여 보론산(

)을 포함하는 화합물을 제조하거나, 마그네슘을 사용하여 상온에서 그리냐드화 반응 후 섭씨 0도에서 트리메틸보레이트를 1 내지 5당량 투입하고 상온에서 2 내지 24시간 반응하여 보론산(

)을 포함하는 화합물을 합성하는 제조 방법, 또는 디메톡시에탄, 톨루엔 또는 테트라하이드로퓨란 등과 같은 유기용매와 2N-탄산나트륨 내지 2N-탄산칼륨 수용액과 같은 염기성 수용액 그리고 테트라키스(트리페닐포스핀)팔라듐(0) 0.05 내지 0.4당량을 사용하여 보론기(

,

)를 포함하는 화학식 B와 같은 보론 유도체의 제조방법 등이 있다. 단, 본 제조방법은 상기 반응식에 한정되지 않는다.As shown in Scheme B of Scheme 2, boronic acid (

) Is prepared by reacting 1 equivalent of a compound containing a halogen group (bromine, iodine, etc.) with an equivalent of an A compound in an organic solvent such as anhydrous tetrahydrofuran at a temperature of -30 ° C to -75 ° C , 1 to 5 equivalents of trimethylborate is added thereto, and the mixture is reacted at room temperature for 2 to 24 hours to obtain boronic acid (

), Or magnesium is used for the grignarding reaction at room temperature, 1 to 5 equivalents of trimethylborate is added at 0 deg. C, and the reaction is carried out at room temperature for 2 to 24 hours to obtain boronic acid

) Or a basic aqueous solution such as an aqueous solution of 2N sodium carbonate to 2N-potassium carbonate and an organic solvent such as dimethoxyethane, toluene or tetrahydrofuran, and a solution of tetrakis (triphenylphosphine) palladium 0) < / RTI > in the presence of boron (

,

And a method for producing a boron derivative such as the formula (B). However, the production method is not limited to the above reaction formula.

         B C

[Reaction Scheme 3]

In the Suzuki coupling reaction, 1 equivalent of compound B and an aryl halide compound are reacted with an organic solvent such as dimethoxyethane, toluene or tetrahydrofuran, a basic aqueous solution such as 2N-sodium carbonate aqueous solution and a palladium catalyst And 0.05 to 0.5 equivalents in the temperature range of 60 ° C to 150 ° C for 2 hours to 48 hours. However, the production method is not limited to the above reaction formula.

              C

[Reaction Scheme 4]

As the bromination reaction as shown in Reaction Scheme 4, 1 equivalent of the intermediate of Compound C, which is the precursor of Formula 1, is reacted with N-bromosuccinimide or N-iodosuccinimide in an organic solvent such as N, N-dimethylformamide or carbon tetrachloride 1 to 4 equivalents of a compound represented by the formula (1) can be prepared, which contains a halogen group as a useful intermediate of the OLED material reacted by shielding or opening the light at a temperature in the range of 15 to 150 degrees Celsius. However, the production method is not limited to the above reaction formula.

[Reaction Scheme 5]

)을 포함하는 화합물을 제조하거나 디메톡시에탄, 톨루엔 또는 테트라하이드로퓨란 등과 같은 유기용매와 2N-탄산나트륨 내지 2N-탄산칼륨 수용액과 같은 염기성 수용액 그리고 테트라키스(트리페닐포스핀)팔라듐(0) 0.05 내지 0.4당량 그리고 을 사용하여 보론기(

,

)를 포함하는 보론 유도체인 화학식 1을 제조할 수 있다. 단, 본 제조방법은 상기 반응식에 한정되지 않는다.Further, as shown in Reaction Scheme 5, 1 equivalent of the formula (1-1), which is an intermediate containing a halogen group (bromine, iodine, etc.), can be lithiated in an organic solvent such as anhydrous tetrahydrofuran in a low temperature lithium reaction at a temperature range of- Then, 1 to 5 equivalents of trimethylborate is added thereto, and the mixture is reacted at room temperature for 2 to 24 hours to obtain boronic acid

) Or an organic solvent such as dimethoxyethane, toluene or tetrahydrofuran, a basic aqueous solution such as 2N-sodium carbonate to 2N-potassium carbonate aqueous solution and a basic aqueous solution such as tetrakis (triphenylphosphine) palladium (0) 0.4 eq., And the boron (

,

), Which is a boron derivative, can be prepared. However, the production method is not limited to the above reaction formula.

Hereinafter, specific examples of the organosilane compound represented by the formula (1) of the present invention are shown, but the present invention is not limited to these exemplified compounds.

Hereinafter, a method for manufacturing an organic electroluminescent material and an organic electroluminescent device according to the present invention will be described.

The method for producing an organic electroluminescent material according to the present invention is characterized in that an organosilane compound of the above-mentioned formula (1) and an aryl group having 6 to 30 carbon atoms in which a Suzuki coupling reaction is present (unsaturated aliphatic groups may be included in the structure, Or a substituent group) may be subjected to a Suzuki coupling reaction to produce an organic electroluminescent material. The Suzuki coupling reactor means a boron group or a halogen group and is present in each of the two compounds to be reacted. The aryl group having 6 to 20 carbon atoms may include an unsaturated aliphatic group in the structure, and a part of hydrogen may be substituted with a substituent. Specific examples include those described above as examples of A1, A2, and L1.

Specific examples of the production method include the following examples.

[Reaction Scheme 6]

As shown in Reaction Scheme 6, 1 equivalent of an organosilane compound represented by the general formula (1) including a halogen and an arylboronic acid compound are reacted with an organic solvent such as dimethoxyethane, toluene or tetrahydrofuran, a 2N-sodium carbonate aqueous solution or a 2N- And 0.05 to 0.5 equivalents of a palladium catalyst. The organic electroluminescent material of the present invention can be prepared by a Suzuki coupling reaction at a temperature range of 60 to 150 degrees Celsius for 2 to 24 hours. Here, the positions of the boron group and the halogen group may be interchanged and included in the present invention. However, the production method is not limited to the above reaction formula.

The present invention provides an organic electroluminescent device comprising an organic electroluminescent material produced by the above-described production method. The organic electroluminescent device according to the present invention is an organic electroluminescent device having a plurality of organic compound layers including a cathode, a cathode and a light emitting layer disposed between the anode and the cathode, wherein the organic electroluminescent material Is contained in all or part of the plurality of organic compound layers.

A more concrete example is as follows.

1, an organic electroluminescent device according to an embodiment of the present invention includes a substrate 1, an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, a cathode 7). An electron injection layer may be further provided between the electron transport layer 6 and the cathode 7 and a hole injection layer 3 may be further provided between the anode 2 and the hole transport layer 4. [ The organic compound layer means a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and the like. And at least one of the organic compound layers contains the organic electroluminescent material.

Examples of the anode (2) material include metal oxides or metal nitrides such as ITO, IZO, tin oxide, zinc oxide, zinc aluminum oxide, and titanium nitride; Metals such as gold, platinum, silver, copper, aluminum, nickel, cobalt, lead, molybdenum, tungsten, tantalum and niobium; An alloy of such a metal or an alloy of copper iodide; And conductive polymers such as polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, poly (3-methylthiophene), and polyphenylene sulfide. The anode 2 may be formed of only one of the above-mentioned materials or may be formed of a mixture of a plurality of materials. Further, a multi-layer structure composed of a plurality of layers of the same composition or different compositions may be formed.

The hole injecting layer 3 of the present invention can be formed using materials known in the art, including but not limited to PEDOT / PSS or copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylphenylamino) Triphenylamine (m-MTDATA) are formed to a thickness of 5 nm to 40 nm.

The hole transport layer 4 may be formed of a material selected from the group consisting of 4,4'-bis [N- (1-naphthyl) -N-phenyl-amino] (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD) can be used.

The light emitting layer 5 may be made of materials known in the art, including but not limited to (4,4'-bis (2,2-diphenyl-ethen-1-yl) diphenyl (DPVBi) (2-methyl-8-quinolinolato) (triphenylsiloxy) aluminum (III) (SAlq), bis (2-methyl- (Para-phenolato) aluminum (III) (BAlq), bis (salen) zinc (II), 1,3-bis [4- (N, N- dimethylamino) phenyl-1,3,4-oxadiazoyl ] Benzene (OXD8), 3- (biphenyl-4-yl) -5- (4-dimethylamino) 4- (4-biphenyl) -4-phenyl-5- (4-tertiary-butylphenyl) -1,2,4-triazole (TAZ), 2,2 ', 7,7'- 4-yl) -9,9'-spirofluorene (Spiro-DPVBI), tris (para-phenyl-4-yl) amine (p- ) -2,2-bithiophene (BMB-2T), and perylene.

(4-dicyanomethylene-2-methyl-6- (para-dimethylaminostyryl) -4H-pyran), DCM2 (4- (Dicyanomethylene) -2-methyl-6- (1,1, 7, -dichloromethyl) 9H-pyran), DCJTB (4- (dicyanomethylene) -2-tertiarybutyl-6- (1,1,7,7-tetramethylpyrrolidyl -9-enyl) -4H-pyran, DCJTI (4-dicyanomethylene) -2-isopropyl-6- (1,1,7,7-tetramethyljulolidyl- ) And Nile red, Rubrene and the like can be used as a host or a dopant.

The dopant may be omitted or optionally added, and it is preferable to use one listed in the host material, although not limited thereto.

The electron transport layer 6 may include aryl substituted oxadiazole, aryl-substituted triazole, aryl-substituted phenanthroline, benzoxazole, or benzothiazole compounds such as 1, 3-bis (N, Nt-butyl-phenyl) -1,3,4-oxadiazole (OXD-7); 3-phenyl-4- (1'-naphthyl) -5-phenyl-1,2,4-triazole (TAZ); 2,9-dimethyl-4,7-diphenyl-phenanthroline (basocuproin or BCP); Bis (2- (2-hydroxyphenyl) -benzoxazolate) zinc; Or bis (2- (2-hydroxyphenyl) benzothiazolate) zinc; The electron transporting material may be (4-biphenyl) (4-t-butylphenyl) oxydiazole (PDB) and tris (8- quinolinato) aluminum (Alq3), preferably tris Quinolinato) aluminum (III) (Alq3) are preferable.

The electron injecting layer and the cathode 7 may be made of any material known in the art and include, but are not limited to, LiF as an electron injecting layer and a metal having a low work function such as Al, Ca, Mg, And preferably Al is preferable.

Hereinafter, the present invention will be described in more detail with reference to Synthesis Examples and Examples.

The reaction scheme from the starting material for the synthesis of the compound 1-1 is as follows.

<Examples>

Synthesis Example 1 Synthesis of Compound A.

4 g (17 mmol) of dibromobenzene was dissolved in ether, and the temperature was lowered to add n-BuLi. Then, triphenylsilyl chloride was added thereto and reacted at room temperature. After the reaction was completed, the reaction product was extracted with ether, and the solvent was removed under reduced pressure. The product was separated into a column and dried under reduced pressure. 66% yield was obtained.

1 H-NMR (CDCl 3, ppm): 7.54-7.5 (m, Ar-H), 7.45 (Ar-H), 7.40-7.35 (m, Ar-H).

IR (KBr, cm-1): 1568, 1477-1376, 1110, 810, 727, 698.

MS (EI) (calcd for C24H19BrSi, 414; Found: 414).

Synthesis Example 2 Synthesis of Compound B

8.3 g (20 mol) of 4-bromophenyl-triphenylsilane was dissolved in THF, and the temperature was lowered to add n-BuLi. Trimethylborate was added thereto and reacted at room temperature. Poured into diluted hydrochloric acid and stirred for 30 minutes. After extracting with methylene chloride, the solvent was removed under reduced pressure, and the product was separated into a column, followed by filtration under reduced pressure to obtain a yield of 50%.

H-NMR (CDCl3): 7.54 (6H, Ar-H), 7.5 (2H, Ar-H), 7.4 - (OH) 2).

IR (KBr, cm-1): 1589, 1491, 1374-1277, 829, 725, 695.

MS (EI) (calcd for C24H21BO2Si, 380.14 found, 381).

Synthesis Example 3 Synthesis of Compound C

(48.61 mmol) of 9-bromoanthracene, 250 mL of toluene, 2.247 g (1.945 mmol) of tetrakistriphenylphosphine palladium, 146 mL of a 2N sodium carbonate aqueous solution And the mixture was refluxed at 110 DEG C for 18 hours. After the completion of the reaction, the reaction temperature was lowered to room temperature, and the organic layer was extracted with distilled water and dichloromethane. The organic layer was dried over MgSO4, the solvent was removed under reduced pressure, and the product was re-precipitated with dichloromethane and normal hexane. After vacuum drying, 15.95 g (80%) of product was obtained.

MS (EI) (calcd for C38H28Si, 512.71; Found: 512).

Synthesis Example 4 Synthesis of Compound 1

24 g (46.81 mmol) of the compound C, 8.77 g (49.27 mmol) of NBS and 150 mL of DMF were added to a 250 mL three-necked flask, and the mixture was stirred at room temperature for 4 hours. The resulting solid was filtered and thoroughly washed with 1000 mL of methanol. After drying, 20.96 g (76%) of compound D was obtained.

MS (EI) (calcd for C27H17BrN2, 591.61; Found: 591).

The reaction formula of the compound 1-1 synthesized in Synthesis Example is as follows.

Synthesis Example 5 Synthesis of Compound 1-1

(18.59 mmol) of compound 1, 6.14 g (20.45 mmol) of 4- (2,2-diphenylvinyl) phenyl-1-boronic acid and 250 mL of toluene, and tetrakis triphenylphosphine 1.074 g (0.930 mmol) of palladium palladium and 70 mL of a 2N sodium carbonate aqueous solution were added, and the mixture was refluxed at 110 DEG C for 12 hours. After completion of the reaction, the organic layer was extracted with 100 mL of toluene and 300 mL of water, and the solvent was removed under reduced pressure. The washed solid was completely dissolved with 300 mL of THF, then re-precipitated with 1200 mL of n-n-hexane and separated by filtration. After vacuum drying, 12.55 g (88%) of product was obtained.

MS (EI) (calcd for C58H42Si, 767.04; Found: 767).

The electroluminescent device thus manufactured, i.e., the driving voltage, the color coordinate, and the efficiency were measured in the following manner, and the results are shown in Table 1 .

1) Driving voltage

The organic electroluminescent device manufactured was measured for the change of the current density according to the voltage change. The measurement was carried out by using a current-voltmeter (Kethley SMU 236) while increasing the current density from 2.5 mA / cm 2 to 100 mA / cm 2 by 2.5 mA.

2) Color coordinates

The prepared organic electroluminescent device was measured using a colorimeter (Minolta CS-100A) while increasing the current density from 2.5 mA / cm 2 to 100 mA / cm 2 by 2.5 mA.

3) Efficiency

The luminous efficiency was calculated using the luminance and current density measured above.

4) ELmax

Power was supplied from a power supply (Kethley SMU 236) and the wavelength was set to ELmax at the highest intensity of the spectrum taken from the photodiode (Ocean Optics).

< Example  1>  Fabrication and Evaluation of Organic Compound 1-1

As shown in FIG. 1, an ITO electrode was formed on a glass substrate, followed by UV-ozone cleaning or oxygen plasma cleaning. Then, a CuPc ( phthalocyanine copper complex was deposited to a thickness of 100 Å. NPD (N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) benzidine) having a structure represented by the following formula 2-2 was formed as a hole transport layer 4 After deposition, Compound 1-1 was formed into a 300 Å thick light emitting layer with a blue light emitting material. Alq3 (tris- (8-hydroxyquinoline) aluminum (III)) having a structure represented by the following Formula 2-3 was vacuum deposited as the electron transport layer 6 to a thickness of 300 Å. Thereafter, an Al: Li layer 7 was vacuum deposited on the upper part to form an aluminum-lithium electrode having a thickness of 1000 Å, thereby producing a blue organic electroluminescence device.

< Comparative Example  1>

A blue organic electroluminescent device was manufactured and measured in the same manner as in Example 1, except that DPVBi having the structure of the following Formula 2-4 was used as a blue luminescent material when forming the luminescent layer.

 [Chemical Formula 2-4]

[Table 1]

Current density
(mA / cm ² ) Luminance
(cd / m ² ) Color coordinates CIE1931
(x, y) efficiency
(cd / A) Example 1 10 391 (0.145, 0.111) 3.91 Comparative Example 1 10 312 (0.15, 0.16) 3.12

The present invention provides an organosilane compound represented by formula (1), which is an intermediate for the synthesis of a useful organic electroluminescent material having steric hindrance properties to prevent excimer and exciplex which improve thermal stability and hinder emission characteristics, And a low cost organic electroluminescent material manufacturing process can be provided. Further, using the prepared light emitting material as a light emitting layer material, a high efficiency, a high color purity, a low driving voltage and a long driving life can be provided in an electroluminescent device.

Claims (7)

delete delete delete Wherein the organosilane compound is selected from the following compounds 1-32.

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