KR100563075B1 - Organic silicone compound, light-emitting compound formed therefrom and display device employing the light-emitting compound as color-developing substance - Google Patents

Abstract

The present invention provides an organic silicon compound represented by Formula 1, a light emitting compound of Formula 2 formed therefrom, and a display device employing the light emitting compound as a color developing material.

In the above formula, R 'is a phenyl group or an alkyl group having 1 to 8 carbon atoms, and X ₁ and X ₂ are halogen atoms irrespective of each other.

Wherein Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , Ar ₅ , Ar ₆ , and Ar ₇ are each independently a chemical bond, unsubstituted or substituted phenyl, unsubstituted Or substituted naphthalene, unsubstituted or substituted anthracene, unsubstituted or substituted diphenylanthracene, unsubstituted or substituted phenanthrene, unsubstituted or substituted indene, unsubstituted or Substituted acenaphtene, unsubstituted or substituted biphenyl, unsubstituted or substituted fluorene, unsubstituted or substituted carbazole, unsubstituted or substituted thiophene, unsubstituted or Substituted pyridine, unsubstituted or substituted oxadiazole, unsubstituted or substituted oxazole, unsubstituted or substituted triazole, unsubstituted or substituted benzothiophene, unsubstituted or substituted dibenzo To furan (dibenzofuran), unsubstituted or substituted thiadiazole Is selected from the eojin group, B is a chemical bond or _{- (R 6) C (R} 7) - or _{- (R 8) Si (R} 9) - , X is O, S or

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are each independently hydrogen, ethyleneoxy group, alkyl group having 1 to 20 carbon atoms, and carbon number 1 to 20 alkyl groups, aryl groups, trimethylsilyl groups and trimethylsilylaryl groups, k ₁ and k ₂ are 0 or 1 irrespective of each other, and 0 <l <1, 0 <m <1 ( Here, l and m are mole fraction (l + m = 1), and n is an integer of 10 to 200.

Description

Organic silicon compound, light-emitting compound formed therefrom and display device employing the light-emitting compound as color-developing substance

1 is a view showing the structure of a general organic electroluminescent device,

2-6 are diagrams showing the synthetic routes of the compounds represented by Formulas 3, 4, 5, 6, and 7 according to the present invention.

<Description of the code for the main part of drawing

11 ... substrate 12 ... anode

13 ... hole transport layer 14 ... light emitting layer

15 ... electron transport layer 16 ... cathode

The present invention relates to an organic silicon compound, a blue light emitting compound formed using the same, and a display device employing the light emitting compound as a color developing material.

As the development of the information and communication industry is accelerating, a display device having high performance is required. Display devices are generally classified into light emitting display devices and non-light emitting display devices. The light emitting display device includes a cathode ray tube, an electro-luminescence display (ELD), a light emitting diode (LED), and the like, and a non-light emitting display device includes a liquid crystal display device.

Indicators indicating the basic performance of the display device include an operating voltage, power consumption, brightness, contrast, response time, lifetime, and display color.

Liquid crystal display devices, which are one of the non-light emitting display devices, have the advantage of being light and low power consumption, and are currently being used most widely. However, the characteristics such as response time, contrast, and viewing angle have not reached satisfactory levels, and there is still much room for improvement. Accordingly, an electron light emitting device is attracting attention as a next generation display device that can solve such a problem.

An electroluminescence device (EL device) is a spontaneous light emitting display device having advantages of wide viewing angle, excellent contrast, and fast response speed.

EL elements are classified into inorganic EL elements and organic EL elements according to materials for forming an emitter layer. Herein, the organic EL device has an advantage of excellent luminance, driving voltage, and response speed, and multicoloring, compared to the inorganic EL device.

1 is a cross-sectional view showing the structure of a general organic EL device. Referring to this, an anode 12 is formed on the substrate 11. On the anode 12, a hole transport layer 13, a light emitting layer 14, an electron transport layer 15, and a cathode 16 are sequentially formed. Here, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 are organic thin films made of an organic compound.

The driving principle of the organic EL element having the above structure is as follows.

When a voltage is applied between the anode 12 and the cathode 16, holes injected from the anode 12 are moved to the light emitting layer 14 via the hole transport layer 13. On the other hand, electrons are injected from the cathode 16 into the light emitting layer 14 via the electron transport layer 15, and carriers recombine in the light emitting layer 14 region to generate excitons. This exciton is changed from an excited state to a ground state, whereby an image is formed by the fluorescent molecules of the light emitting layer emitting light.

Meanwhile, in 1987, kodak developed an EL device using aromatic diamine and aluminum complex, which are small molecules, as a light emitting layer forming material (Appl. Phys. Lett. 51 , 913, 1987).

In addition, as a light emitting layer forming material, poly (p-phenylenevinylene) (PPV), poly (2-methoxy-5- (2'-ethylhexyloxy) -1,4-phenylenevinylene) and the like Organic electroluminescent devices using polymers have been published (Nature, 347 , 539, 1990 & Appl. Phys. Lett. 58 , 1982, 1991).

However, PPV in the polymer has a great difficulty in forming a film by spin coating because of poor solubility in organic solvents. In order to solve this problem, a soluble PPV has been developed incorporating a functional group capable of improving the solubility characteristics of the organic solvent in PPV. Organic electroluminescent devices having a light emitting layer made of PPV or derivatives thereof are typically green.

On the other hand, the blue light emitting compound known to date has a problem that the luminous efficiency is lowered compared to the light emitting compound of other colors, and thus the need for development of a new blue light emitting compound is gradually increasing.

The technical problem to be achieved by the present invention is to provide an organic silicon compound and a method of manufacturing the same in order to solve the above problems.

Another technical problem to be achieved by the present invention is to provide a light emitting compound that can implement blue color while improving luminous efficiency.

Another object of the present invention is to provide a display device employing the light emitting compound as a coloring material.

In order to achieve the first object, the present invention provides an organosilicon compound represented by the formula (1).

<Formula 1>

Wherein R 'is a phenyl group or an alkyl group having 1 to 8 carbon atoms,

X ₁ and X ₂ are halogen atoms irrespective of each other.

Preferably, in the compound of Formula 1, A ₁ and A ₂ are both phenyl groups, and X ₁ and X ₂ are both bromine.

The second object of the present invention is the step of (a) dissolving 1,4-dihalogenbenzene in an organic solvent, and then reacting by dropwise addition of a lithium compound; And

(b) by the method of producing an organosilicon compound represented by the formula (1) comprising the step of reacting by dropwise addition of dialkyldichlorosilane to the reaction mixture of step (a).

Wherein R and R 'are each independently a phenyl group or an alkyl group having 1 to 8 carbon atoms,

X ₁ and X ₂ are halogen atoms irrespective of each other.

The third object of the present invention is achieved by a light emitting compound represented by the formula (2).

<Formula 2>

Wherein Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , Ar ₅ , Ar ₆ , and Ar ₇ are each independently a chemical bond, unsubstituted or substituted phenyl, unsubstituted. Or substituted naphthalene, unsubstituted or substituted anthracene, unsubstituted or substituted diphenylanthracene, unsubstituted or substituted phenanthrene, unsubstituted or substituted indene, unsubstituted Or substituted acenaphtene, unsubstituted or substituted biphenyl, unsubstituted or substituted fluorene, unsubstituted or substituted carbazole, unsubstituted or substituted thiophene, unsubstituted Or substituted pyridine, unsubstituted or substituted oxadiazole, unsubstituted or substituted oxazole, unsubstituted or substituted triazole, unsubstituted or substituted benzothiophene, unsubstituted or substituted di Dibenzofuran, unsubstituted or substituted thiadiazole Is selected from the group eojin,

B is a chemical bond or-(R ₆ ) C (R ₇ )-or-(R ₈ ) Si (R ₉ )-,

X is O, S or

ego,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are independently of each other hydrogen, ethyleneoxy group, C1-C20 alkyl group, C1-C20 20 alkyl group, aryl group, trimethylsilyl group and trimethylsilylaryl group,

k ₁ and k ₂ are 0 or 1 independent of each other,

0 <l <1, 0 <m <1, where l and m are mole fractions, where l + m = 1

n is an integer from 10 to 200.

A fourth object of the present invention is achieved by a display element, wherein the light emitting compound is employed as a color generating material. As a preferable aspect of this invention, the organic electroluminescent element which employ | adopts the light emitting compound represented by General formula (2) as a coloring material is mentioned.

That is, the fourth object of the present invention is also an organic electroluminescent device comprising an organic film provided between a pair of electrodes,

It provides an organic electroluminescent device characterized in that the organic film comprises a light emitting compound of formula (2).

<Formula 2>

Wherein Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , Ar ₅ , Ar ₆ , and Ar ₇ are each independently a chemical bond, unsubstituted or substituted phenyl, unsubstituted Or substituted naphthalene, unsubstituted or substituted anthracene, unsubstituted or substituted diphenylanthracene, unsubstituted or substituted phenanthrene, unsubstituted or substituted indene, unsubstituted or Substituted acenaphtene, unsubstituted or substituted biphenyl, unsubstituted or substituted fluorene, unsubstituted or substituted carbazole, unsubstituted or substituted thiophene, unsubstituted or Substituted pyridine, unsubstituted or substituted oxadiazole, unsubstituted or substituted oxazole, unsubstituted or substituted triazole, unsubstituted or substituted benzothiophene, unsubstituted or substituted dibenzo Composed of furan (dibenzofuran), unsubstituted or substituted thiadiazole Selected from the group

B is a chemical bond or-(R ₆ ) C (R ₇ )-or-(R ₈ ) Si (R ₉ )-,

X is O, S or

ego,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are independently of each other hydrogen, ethyleneoxy group, C1-C20 alkyl group, C1-C20 20 alkyl group, aryl group, trimethylsilyl group and trimethylsilylaryl group,

k ₁ and k ₂ are 0 or 1 independent of each other,

0 <l <1, 0 <m <1, where l and m are mole fractions, where l + m = 1

n is an integer from 10 to 200.

The organosilicon compound represented by Formula 1 according to the present invention can be usefully used in synthesizing other compounds as intermediates. The organosilicon compound of Formula 1 is not particularly limited in its manufacturing process, but is preferably prepared according to the following process.

First, 2 equivalents of 1,4-dihalogenbenzene, such as 1,4-dibromobenzene, are dissolved in an organic solvent, and then the temperature of the reaction mixture is adjusted to about -40 to -20 ° C. Here, diethyl ether or the like is used as the organic solvent. Subsequently, 2 equivalents of a lithium compound such as n-butyllithium is added dropwise to the reaction mixture for reaction for a predetermined time.

The temperature of the reaction mixture is adjusted to about -80 to -70 ° C, 1 equivalent of dialkyldichlorosilane, such as dichlorodiphenylsilane, is added dropwise, followed by stirring for a predetermined time to obtain an organosilicon compound of Formula 1.

On the other hand, the compound represented by the formula (2) is a blue light emitting material, it is very excellent in luminous efficiency. Specific examples of such compounds include k ₁ , k ₂ And s are all 0, B is a single bond, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₅ , and Ar ₆ are phenyl groups, X is O, and R ₁ is hydrogen, k ₁ And k ₂ are both 1. s is 0, B represents a single bond, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₅ And Ar ₆ is a phenyl group, X is O, R ₁ is hydrogen, and-(R ₂ ) Ar ₄ (R ₃ )-and-(R ₄ ) Ar ₇ (R ₅ )-are represented by the formula

The compound of formula 4, k ₁ , s, l, m and n are all 1, k ₂ is 0, B is -C (CH ₃ ) _2- , Ar ₁ , Ar ₂ represents a single bond , Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, R ₁ , R ₂ and R ₃ are hydrogen, k ₁ , s, l, m and n are all 1, k ₂ is 0, B Is -Si (Ph) _2- , Ar ₁ , Ar ₂ represent a single bond, Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, R ₁ , R ₂ and R ₃ are hydrogen, wherein k ₁ , s, l, m and n are all 1, k ₂ is 0, B is -Si (Ph) _2- , Ar ₁ , Ar ₂ , Ar ₃ all represent a single bond, Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, R ₁ is hydrogen, and-(R ₂ ) Ar ₄ (R ₃ )-is represented by the formula

And the compound represented by the formula (7).

The compound of formula 2 according to the present invention is preferably used as a material for forming the light emitting layer or the electron transport layer of the organic electroluminescent device.

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

First, an anode electrode material is coated on the substrate. Here, a substrate used in a conventional organic EL device is used, and a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, transparent and excellent indium tin oxide (ITO), tin oxide (SnO 2), and zinc oxide (ZnO) are used as the anode electrode material.

A hole transport layer is formed by spin coating a material for forming a hole transport layer on the anode electrode. Thereafter, the light emitting layer is formed by spin coating the compound of Formula 2 on the hole transport layer.

 Subsequently, the organic EL device is completed by forming a cathode by vacuum evaporation or sputtering of the cathode forming metal as a whole on the light emitting layer. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-phosphorus ( Mg-Ag) and the like.

The electron transport layer may be formed on the emission layer before forming the cathode. The electron transport layer may use a conventional material for forming an electron transport layer, or may be formed by spin coating a compound of the formula (2).

The hole transport layer material is not particularly limited, and a conventional hole transport layer forming material such as polyvinylcarbazole (PVK), PDPMA having the following structural formula is used.

The organic electroluminescent device of the present invention can further form an intermediate layer for improving properties between two layers selected from an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode. For example, a buffer layer may be further formed between the anode and the hole transport layer. The formation of the buffer layer reduces the contact resistance between the anode and the hole transport layer and improves the hole transport ability of the anode to the light emitting layer. It is possible to obtain an effect of improving the characteristics of the device as a whole.

The buffer layer forming material is not particularly limited, but polyethylene dioxythiophene (PEDT), polyaniline, or the like is used.

The organic electroluminescent device may be manufactured in the order described above, that is, in the order of anode / hole transport layer / light emitting layer / electron transport layer / cathode, or in the reverse order, that is, cathode / electron transport layer / light emitting layer / hole transport layer / anode You may manufacture.

2-6 are diagrams showing the synthetic routes of the compounds represented by Formulas 3, 4, 5, 6, and 7 according to the present invention. Hereinafter, the present invention will be described in detail with reference to the drawings, but the present invention is not limited only to the following examples.

Synthesis Example  1. Compound of Formula 3

Benzene and the equivalent triphenylphosphine were added to 4-bromobenzyl bromide and refluxed for 12 hours to obtain compound (A) (yield: 95%).

4-Bromobenzophenone was added to compound (A), followed by a wittig reaction to obtain compound (B) (yield: 40%).

Separately, anhydrous acetone and purified pyridine were added to 2 equivalents of 4-bromobenzoyl chloride, and then hydrazine monohydrate was added dropwise thereto, and then the temperature of the mixture was adjusted to 40 ° C., followed by reaction at this temperature. Compound (C) was obtained (yield: 70%).

Thionyl chloride and toluene were added to compound (C), and then refluxed for 24 hours to obtain compound (D) (yield: 95%).

Anhydrous nickel (II) chloride, 2,2′-bipyridine, triphenylphosphine and zinc powder were added to a three necked round bottom flask, and then argon gas was repeatedly purged about 10 times. Anhydrous DMF was added to the reaction flask, and then the temperature of the reaction mixture was adjusted to 50 ° C. The reaction mixture was stirred for 30 minutes, and then the reaction mixture was added rapidly to compound (B) and (D) under nitrogen gas atmosphere. The reaction mixture was then adjusted to 90 ° C. and then stirred at this temperature for 24 hours to give the compound of formula 3 (yield: 45%). Wherein l ₁ was 0.01 to 0.99, m ₁ was 0.01 to 0.99, and n ₁ was an integer of 5 to 1,000.

Synthesis Example  2. Compound of Formula 4

After dissolving 12.4 g (0.1 mol) of 4-methoxyphenol in DMF, 19 g (0.1 mol) of potassium carbonate and 2-ethylbromohexane were added thereto, and the mixture was refluxed for 24 hours.

The reaction mixture was poured into cold water to form a precipitate. The obtained precipitate was filtered and dried to obtain compound (E) (yield: 80%).

Compound (E) was dissolved in carbon tetrachloride, and bromine was added to react for 12 hours to obtain compound (F) (yield: 65%).

Compound (F) was dissolved in THF, and then magnesium was added thereto and refluxed for 1 hour to prepare a corresponding Grignard reagent. Trimethylborate was reacted with this Grignard reagent to obtain Compound (G) (yield: 47%).

Compound (B) and compound (D) are mixed, and 2 equivalents of compound (G) and tetrakis (triphenylphosphine) palladium and 2M-K ₂ CO ₃ are added to the mixture. An aqueous solution was added. The reaction mixture was reacted for 24 hours to obtain a compound of compound 4 (yield: 60%). Wherein l ₂ was an integer of 0.01 to 0.99, m ₂ was 0.02 to 0.99 and n ₂ was 5 to 1,000.

Synthesis Example  3. Compound of Formula 5

Vinylmagnesium bromide was added to the round bottom flask, and tri-n-butyltin chloride and THF were added dropwise under a nitrogen gas atmosphere. The reaction mixture was refluxed for 24 hours to obtain compound (H) (yield: 80%)

After dissolving 2,2-diphenylpropane in carbon tetrachloride, 2 equivalents of bromine was added dropwise and stirred at room temperature for 12 hours to obtain compound (I) (yield: 78%).

Anhydrous toluene, compound (I) and a small amount of 2,6-di-tert-butyl-4-methylphenol (2,6-di-tert-butyl-4-methylphenol: BHT) and tetrakis (triphenylphosphine After stirring the mixture of palladium catalyst, 2 equivalents of compound (H) was added dropwise thereto. The obtained reaction mixture was refluxed for 24 hours to obtain compound (J) (yield: 60%).

To the compound (J) was added DMF, where compound (D), palladium (II) diacetate (CH ₃ CO ₂ ) ₂ Pd, tritolylphosphine (o-CH ₃ C ₆ H ₄ ) ₃ P and tri Ethylamine was added and mixed. The resulting reaction mixture was heated to 100 ° C. and reacted for 40 hours.

After the reaction was completed, the reaction mixture was poured into methanol to form a precipitate. The obtained precipitate was dissolved in chloroform, and methanol was added thereto to reprecipitate. The obtained precipitate was filtered and dried to obtain the compound of formula 5 (yield: 38%). N ₃ was an integer of 5 to 1,000 here.

Synthesis Example  4. Compound of Formula 6

Two equivalents of 1,4-dibromobenzene were dissolved in diethyl ether and then the temperature of the reaction mixture was adjusted to -40 ° C. Subsequently, n-butyllithium was added dropwise to the reaction mixture and reacted at room temperature for 2 hours. Thereafter, the temperature of the reaction mixture was adjusted to -78 ° C, and then 1 equivalent of diphenyldichlorosilane was added dropwise at this temperature. The obtained reaction mixture was stirred at room temperature for 12 hours to obtain compound (K) (yield: 78%).

Anhydrous toluene, compound (K) and a small amount of 2,6-di-tert-butyl-4-methylphenol (2,6-di-tert-butyl-4-methylphenol: BHT) and tetrakis (triphenylphosphine After stirring the mixture of palladium catalyst, 2 equivalents of compound (H) was added dropwise thereto. The reaction mixture was refluxed for 24 hours to give compound (L) (yield: 60%).

DMF was added to compound (L), followed by compound (D), palladium (II) diacetate (CH ₃ CO ₂ ) ₂ Pd, tritolylphosphine (o-CH ₃ C ₆ H ₄ ) ₃ P, and Triethylamine was added and mixed. The resulting reaction mixture was heated to 100 ° C. and reacted for 40 hours.

After the reaction was completed, the reaction mixture was poured into methanol to form a precipitate. The obtained precipitate was dissolved in chloro-ro- pain, and methanol was added to it to reprecipitate. The obtained precipitate was filtered and dried to obtain the compound of formula 6 (yield: 42%). N ₄ here was an integer of 5 to 1,000.

Synthesis Example  5. Compound of Formula 7

1,3,5-tribromobenzene was dissolved in diethyl ether and then the temperature of the reaction mixture was adjusted to -40 ° C. Subsequently, n-butyllithium was added dropwise to the reaction mixture and reacted at room temperature for 2 hours. The temperature of the reaction mixture was adjusted to -78 deg. C, and then 1 equivalent of diphenyldichlorosilane was added dropwise at this temperature. The reaction mixture was stirred at room temperature for 12 hours to give compound (M) (yield: 78%).

Anhydrous toluene, compound (M) and a small amount of 2,6-di-tert-butyl-4-methylphenol (2,6-di-tert-butyl-4-methylphenol: BHT) and tetrakis (triphenylphosphine After stirring the mixture of palladium catalyst, 2 equivalents of compound (H) was added dropwise. The reaction mixture was refluxed for 24 hours to give compound (N) (yield: 60%).

DMF was added to compound (N), followed by compound (D), palladium (II) diacetate (CH ₃ CO ₂ ) ₂ Pd, tritolylphosphine (o-CH ₃ C ₆ H ₄ ) ₃ P, and Triethylamine was added and mixed. The reaction mixture was heated to 100 ° C. and reacted for 40 hours.

After the reaction was completed, the reaction mixture was poured into methanol to form a precipitate. The obtained precipitate was dissolved in chloroform, and methanol was added thereto to reprecipitate. The obtained precipitate was filtered and dried to obtain a compound of formula 7 (yield: 35%). N ₅ here was an integer of 5-1,000.

Example 1

After forming an ITO electrode on the glass substrate, the buffer layer formation composition which melt | dissolved 5 g of PEDT in 5 g of isopropyl alcohol was spin-coated, and the buffer layer of 400 micrometers thick was formed.

Subsequently, the light emitting layer having a thickness of 600 Å was formed by spin coating the compound of Formula 3 on the buffer layer.

Thereafter, Al: Li was vacuum-deposited on the emission layer to form an aluminum lithium electrode having a thickness of 1200 Å, thereby manufacturing an organic EL device.

Example  2

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of Formula 4 was used instead of the compound of Formula 3 in forming the emission layer.

Example  3

An organic electroluminescent device was manufactured according to the same method as Example 1 except for using the compound of Formula 5 instead of the compound of Formula 3 in forming the emission layer.

Example  4

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of Formula 6 was used instead of the compound of Formula 3 in forming the emission layer.

Example  5

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of Formula 7 was used instead of the compound of Formula 3 to form the emission layer.

Example  6

After forming an ITO electrode on the glass substrate, the hole transport layer formation composition which melt | dissolved 0.5 g of PVK in 100 g of chlorobenzene was spin-coated, and the hole transport layer was formed into 400 micrometers in thickness.

Thereafter, spin-coating a compound of Formula 3 on the hole transport layer to form a light emitting layer having a thickness of 400Å.

An organic electroluminescent device was manufactured by vacuum-vaporizing Al: Li on the light emitting layer to form an aluminum lithium electrode having a thickness of 1200 Å.

Example  7

An ITO electrode was formed on the glass substrate, and then poly (p-phenylenevinylene) (PPV) was spin coated on the glass substrate to form a hole transport layer having a thickness of 600 kPa.

Subsequently, a light emitting layer having a thickness of 600 Å was formed by spin coating the compound of Formula 3 on the hole transport layer.

Thereafter, Al: Li was vacuum-deposited on the emission layer to form an aluminum lithium electrode having a thickness of 1200 Å, thereby manufacturing an organic EL device.

In the organic electroluminescent device manufactured according to Example 1-7, the current-voltage, luminance-voltage and color characteristics were evaluated and shown in Table 1 below.

division Start voltage (Turn-on voltage) Highest brightness (cd / ㎡) color Example 1 3 8000 Blue (460 nm) Example 2 3 7000 Blue (470 nm) Example 3 3 7000 Blue (470 nm) Example 4 3 10000 Blue (450 nm) Example 5 3 6000 Blue (460 nm) Example 6 5 9000 Blue (460 nm) Example 7 4 13000 Cyan

From Table 1, it can be seen that the organic electroluminescent device manufactured according to Example 1-7 implements blue, and its luminous efficiency is improved compared to the case of using a conventional blue light emitting material.

The organosilicon compound of formula 1 according to the present invention is used in the synthesis of a light emitting compound represented by formula 2 as an intermediate. The light emitting compound of Formula 2 is a blue light emitting material, and has excellent luminous efficiency. Such a light emitting compound can be usefully used as a coloring material of a display element.

In addition, the organic electroluminescent device according to the present invention may be implemented by forming an organic film such as a light emitting layer, an electron transport layer and the like with the light emitting compound of Formula 2, and the luminous efficiency is improved.

Claims (14)

Light emitting compound represented by formula (2): <Formula 2>

Wherein Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , Ar ₅ , Ar ₆ , and Ar ₇ are each independently a chemical bond, unsubstituted or substituted phenyl, unsubstituted Or substituted naphthalene, unsubstituted or substituted anthracene, unsubstituted or substituted diphenylanthracene, unsubstituted or substituted phenanthrene, unsubstituted or substituted indene, unsubstituted or Substituted acenaphtene, unsubstituted or substituted biphenyl, unsubstituted or substituted fluorene, unsubstituted or substituted carbazole, unsubstituted or substituted thiophene, unsubstituted or Substituted pyridine, unsubstituted or substituted oxadiazole, unsubstituted or substituted oxazole, unsubstituted or substituted triazole, unsubstituted or substituted benzothiophene, unsubstituted or substituted dibenzo Composed of furan (dibenzofuran), unsubstituted or substituted thiadiazole Selected from the group B is a chemical bond or-(R ₆ ) C (R ₇ )-or-(R ₈ ) Si (R ₉ )-, X is O, S or

ego, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are independently of each other hydrogen, ethyleneoxy group, C1-C20 alkyl group, C1-C20 20 alkyl group, aryl group, trimethylsilyl group and trimethylsilylaryl group, k ₁ and k ₂ are 0 or 1 independent of each other, 0 <l <1, 0 <m <1, where l and m are mole fractions, where l + m = 1 n is an integer from 10 to 200. The method of claim ₁ , wherein k ₁ , k ₂ And s are all 0, B is a single bond, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₅ , and Ar ₆ are phenyl groups, X is O, and R ₁ is hydrogen. The compound of claim 1, wherein k ₁ and k ₂ are both 1. s is 0, B represents a single bond, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₅ And Ar ₆ is a phenyl group, X is O, R ₁ is hydrogen, and-(R ₂ ) Ar ₄ (R ₃ )-and-(R ₄ ) Ar ₇ (R ₅ )-are represented by the following structural formulas: A light emitting compound characterized by the above-mentioned.

The method of claim ₁ , wherein k ₁ , s, l, m and n are all 1, k ₂ is 0, B is -C (CH ₃ ) _2- , Ar ₁ , Ar ₂ represents a single bond, Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, and R ₁ , R ₂ and R ₃ are hydrogen. The compound of claim ₁ , wherein k ₁ , s, l, m and n are all 1, k ₂ is 0, B is —Si (Ph) ₂ —, Ar ₁ , Ar ₂ represents a single bond, and Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, and R ₁ , R ₂ and R ₃ are hydrogen. The method of claim 1, wherein k ₁ , s, l, m, and n are all 1, k ₂ is 0, B is —Si (Ph) ₂ —, and Ar ₁ , Ar ₂ , and Ar ₃ are all single. Represents a bond, Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, R ₁ is hydrogen, and-(R ₂ ) Ar ₄ (R ₃ )-is represented by the following structural formula.

In an organic electroluminescent device comprising an organic film provided between a pair of electrodes, An organic electroluminescent device, characterized in that the organic film comprises a light emitting compound of Formula 2: <Formula 2>

Wherein Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ , Ar ₅ , Ar ₆ , and Ar ₇ are each independently a chemical bond, unsubstituted or substituted phenyl, unsubstituted Or substituted naphthalene, unsubstituted or substituted anthracene, unsubstituted or substituted diphenylanthracene, unsubstituted or substituted phenanthrene, unsubstituted or substituted indene, unsubstituted or Substituted acenaphtene, unsubstituted or substituted biphenyl, unsubstituted or substituted fluorene, unsubstituted or substituted carbazole, unsubstituted or substituted thiophene, unsubstituted or Substituted pyridine, unsubstituted or substituted oxadiazole, unsubstituted or substituted oxazole, unsubstituted or substituted triazole, unsubstituted or substituted benzothiophene, unsubstituted or substituted dibenzo To furan (dibenzofuran), unsubstituted or substituted thiadiazole Is selected from the group eojin, B is a chemical bond or-(R ₆ ) C (R ₇ )-or-(R ₈ ) Si (R ₉ )-, X is O, S or

ego, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are independently of each other hydrogen, ethyleneoxy group, C1-C20 alkyl group, C1-C20 20 alkyl group, aryl group, trimethylsilyl group and trimethylsilylaryl group, k ₁ and k ₂ are 0 or 1 independent of each other, 0 <l <1, 0 <m <1, where l and m are mole fractions, where l + m = 1 n is an integer from 10 to 200. 8. The method of claim 7, wherein k ₁ , k ₂ And s are all 0, B represents a single bond, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₅ , and Ar ₆ are phenyl groups, X is O, and R ₁ is hydrogen device. 8. The compound of claim 7, wherein k ₁ and k ₂ are both 1. s is 0, B represents a single bond, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₅ And Ar ₆ is a phenyl group, X is O, R ₁ is hydrogen, and-(R ₂ ) Ar ₄ (R ₃ )-and-(R ₄ ) Ar ₇ (R ₅ )-are represented by the following structural formulas: An organic electroluminescent device characterized by.

The method of claim 7, wherein k ₁ , s, l, m and n are all 1, k ₂ is 0, B is -C (CH ₃ ) _2- , Ar ₁ , Ar ₂ represents a single bond, Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, and R ₁ , R ₂ and R ₃ are hydrogen. The method of claim 7, wherein k ₁ , s, l, m and n are all 1, k ₂ is 0, B is -Si (Ph) _2- , Ar ₁ , Ar ₂ represents a single bond, Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, and R ₁ , R ₂ and R ₃ are hydrogen. The method of claim 7, wherein k ₁ , s, l, m, and n are all 1, k ₂ is 0, B is —Si (Ph) ₂ —, and Ar ₁ , Ar ₂ , and Ar ₃ are all single. Represents a bond, Ar ₃ , Ar ₄ , Ar ₅ And Ar ₆ is a phenyl group, X is O, R ₁ is hydrogen, and-(R ₂ ) Ar ₄ (R ₃ )-is represented by the following structural formula.

The organic electroluminescent device according to claim 7, wherein the organic film is a light emitting layer or an electron transporting layer. A display element comprising the light emitting compound according to any one of claims 1 to 6 as a color developing material.

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