KR20040060265A - Blue color emitting compounds for organic electroluminescent device, process for preparing them and organic electroluminescent device using them - Google Patents

Abstract

PURPOSE: Provided is a blue light-emitting compound containing a heterocycle, which solves the problems of conventional phenyl-containing blue light-emitting compounds such as low solubility in a solvent and limitation in purity, and increases the light-emitting efficiency of organic electroluminescence devices. CONSTITUTION: The blue-light emitting compound for organic electroluminescence devices is represented by formula 1, wherein X is O or S, and each of R1 and R2 represents H or -CH2CH3. The compound of formula 1 is prepared by the method comprising the steps of: (1) reacting 9,10-dimethyl anthracene with bromosuccinimide to obtain 9,10-dibromoethyl anthracene; (2) reacting the resultant 9,10-dibromomethyl anthracene with triethyl phosphite to obtain 9,10-bis£(diethoxyphosphoryl)methyl|anthracene; and (3) reacting the resultant 9,10-bis£(diethoxyphosphoryl)methyl|anthracene with a 2-thiophene carboaldehyde derivative or a 2-furandicarboaldehyde derivative represented by formula 2, wherein X is O or S, and R represents H or -CH2CH3.

Description

Blue light emitting compounds for organic electroluminescent device, process for preparing them and organic electroluminescent device using them}

The present invention provides a high-purity material that is easy to recrystallize and sublimate due to its low molecular weight and high solubility while emitting light corresponding to a wavelength in a range similar to that of a blue light emitting compound for an organic electroluminescent device, and more particularly, a compound having a high molecular weight. The present invention relates to a blue light emitting compound for organic electroluminescent device of formula (1) having a heterocycle introduced therein.

[Formula 1]

Wherein X, R ₁ and R ₂ are as defined below.

The present invention also relates to a process for preparing the compound of formula (1).

In addition, the present invention provides an organic electroluminescent device containing the blue light emitting compound, and more particularly an organic electroluminescent device in which an organic thin film layer including a light emitting region is provided between a first electrode (anode) and a second electrode (cathode). The device relates to an organic electroluminescent device, characterized in that at least one of the constituent layers of the organic thin film layer contains a compound represented by the formula (1).

Recently, as the development of the information and communication industry is accelerated, higher performance is required in the field of display devices, which is one of the most important fields. Such displays can be divided into luminescent and non-luminescent. Cathode Ray Tube (CRT), Electroluminescence Display (ELD), Light Emitting Diode (LED), Plasma Display Panel (PDP), etc. have. Non-light emitting displays include liquid crystal displays (LCDs).

The light emitting and non-light emitting displays have basic performances such as operating voltage, power consumption, brightness, that is, brightness, contrast, response speed, lifetime, and display liquid. However, among these, liquid crystal displays, which are widely used to date, have problems in response speed, contrast, and visual dependence among the above basic performances. In this situation, the display using the light emitting diode has a fast response time and is self-luminous so that no back light is required, and the luminance is excellent, and it has various advantages, thus complementing the problems of the liquid crystal display. It is expected to take place as an element.

The light emitting diode is mainly difficult to apply to a large area electroluminescent device because an inorganic material having a crystalline form is used. In addition, in the case of an electroluminescent device using an inorganic material, a driving voltage is required to be 200 V or more, and a price is also disadvantageous. However, since 1987, when Eastman Kodak published a device made of a material having a π-conjugated structure called alumina quinone, research into electroluminescent devices using organic materials has been actively conducted.

Electroluminescence devices (EL devices) are classified into inorganic electroluminescent devices and organic electroluminescent devices according to materials for forming an emitter layer.

The organic electroluminescent device is a self-luminous device that electrically excites fluorescent organic compounds to emit light, and has an advantage of excellent luminance, driving voltage, and response speed, and multicoloring, compared to inorganic electroluminescent devices.

In addition, this element is a conductor element that emits light at low voltage direct current application of several volts, and has excellent characteristics such as high brightness, high speed response, wide viewing angle, surface emission, and thin color emission.

Organic electroluminescent devices have characteristics that are not found in other displays, and thus are expected to be applied to full color flat panel displays.

In 1987, C. W. Tang et al. Reported the practical device performance in organic electroluminescent devices (Applied Physics Letters, Vol. 51, No. 12, pages 913-915 (1987)). Here, they devised a structure in which a thin film (hole transporting layer) obtained from a diamine derivative and a thin film (electron transporting light emitting layer) obtained from tri (8-quinolinolato) aluminum (hereinafter abbreviated as Alq3) were laminated as an organic layer. By using such a laminated structure, it is possible to lower the barrier of injection of electrons and holes from the electrode to the organic layer, and to increase the recombination probability of electrons and holes in the organic layer.

Subsequently, C. Adachi et al. Obtained the three-layer structure of the hole transporting layer, the light emitting layer, and the electron transporting layer (Japanese Journal of Applied Physics, Vol. By devising an organic electroluminescent device having an organic layer of the structure (Applied Physics Letter No. 55, 15, 1489-1491 (1989)) and constructing a multilayer structure suitable for materials and combinations thereof, the device characteristics can be optimized. Indicated.

The organic electroluminescent element may be composed of a first electrode (anode), a second electrode (cathode), and an organic light emitting medium. The organic light emitting medium includes at least two separate organic layers, i.e., one layer for injecting and transporting electrons and one layer for forming a region for injecting and transporting holes in the device. This may be further included. The layer for injecting and transporting electrons and the layer for injecting and transporting holes may be divided into an electron injection layer, an electron transport layer, a hole injection layer, and a hole transport layer, respectively. The organic light emitting medium may further include a light emitting layer in addition to the electron injection and transport layer and the hole injection and transport layer.

The organic EL device having a simple structure may be composed of a first electrode / charge transport layer and a light emitting layer / second electrode. In addition, the organic electroluminescent device may be configured by separating each organic functional layer from the first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode.

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

When a voltage is applied between the anode and the cathode, holes (holes) injected from the anode are moved to the light emitting layer via the hole transport layer. On the other hand, electrons are injected into the light emitting layer from the cathode via the electron transport layer, and carriers are recombined in the light emitting layer to generate excitons. The excitons change from the excited state to the ground state, whereby the fluorescent molecules in the light emitting layer emit light to form an image.

A manufacturing process of a general organic EL device is as follows (see FIG. 1).

First, a first electrode (anode) material is formed on a transparent substrate such as glass. In this case, ITO (Indium tin oxide, In ₂ O ₃ + SnO ₂ ) is mainly used as the cathode material.

A hole injection layer (HIL) is formed on the anode material. Copper phthalocyanine (CuPC: copper (II) phthalocyanine) is mainly used as the hole injection layer, and its thickness is about 10 to 30 nm.

Next, a hole transport layer (HTL) is introduced. The hole transport layer is formed by depositing NPD (N, N-di (naphthalen-1-yl) -N, N'-diphenylbenzidine) to a thickness of about 30 to 60 nm.

In addition, an organic light emitting layer is formed on the hole transport layer. In this case, the organic light emitting layer is formed in a state in which the light emitting material is doped with the light emitting material alone or a host material. For example, in the case of green light emission, Alq3 (tris (8-hydroxy-quinolate) aluminum) (Alq3) is often deposited as a host to a thickness of about 30 to 60 nm, and as a dopant, MQD ( N-methylquinacridone) is used a lot.

Then, an electron transport layer (ETL) and an electron injection layer (EIL) are formed continuously on the organic emission layer, or an electron injection transport layer is formed. In general, the electron transport layer is deposited to a film thickness of 20 to 50 nm using Alq3, and the electron injection layer is deposited to a film thickness of 30 to 50 nm using an alkali metal derivative. In the case of green light emission, since Alq3 used as an organic light emitting layer has excellent electron transport ability, there are many cases where an electron injection / transport layer is not used.

Next, a second electrode (cathode) is formed on the electron injection layer, and finally a protective film is formed.

In general, in order to implement full-color with an organic light emitting device, a light emitting device emitting three kinds of light of green, red, and blue is required.

Blue is doped with a blue dopant to the blue host, and implemented using Alq3 as the electron transport layer (ETL), Alq3 may be omitted depending on the characteristics of the blue host. In the case of red, a red wavelength may be obtained by doping red impurities instead of green impurities during the device fabrication process.

In the case of red, a red wavelength may be obtained by doping red impurities instead of green impurities during the device fabrication process. In the case of the green light emitting device, coumarine 6 or quinacridone derivatives are used as dopants. In the case of a red light emitting device, DCM (4-dicyanomethylene-6- (p-dimethylaminostyryl) -2-methyl-4H-pyran) derivatives such as DCM1 and DCM2 are used as dopants.

However, in the case of the green light emitting device, the stability of the device has been evaluated to the practical level, but in the case of the blue light emitting device, the emission color and the stability of the device have not yet reached the practical level, and the luminous efficiency thereof is also satisfactory. There is a problem that is not reached.

As a blue light emitting material, compounds such as diphenylanthracene, tetraphenylbutadiene, and distyrylbenzene derivatives have been developed, but are known to have a tendency to easily crystallize due to poor film stability.

Idemitsu Co., Ltd. has developed a diphenyl distyryl-based blue luminescent material that improves thin film stability by inhibiting crystallization of phenyl groups on side branches [H. Tokilin, H. Higashi, C. Hosokawa, EP 388, 768 (1990)], and Kuju University have developed distyryl anthracene derivatives having improved electron stability and thin film stability with electron donor and electron donor [Pro. SPIE, 1910, 180 (1993)].

However, the molecular structure of the conventional blue light emitting material is a cyclic compound consisting mostly of phenyl groups, the molecular weight is high, solubility in solvents is low, and recrystallization and sublimation are difficult, making it difficult to obtain a high purity material.

Accordingly, an object of the present invention is to provide a novel low molecular weight blue light emitting material containing a heterocycle and a method of manufacturing the same in order to solve the above problems of the prior art.

In addition, the present invention is an organic electroluminescent device containing the blue light emitting compound, more specifically, an organic electroluminescent device in which an organic thin film layer including a light emitting region is provided between a first electrode (anode) and a second electrode (cathode). In at least one of the constituent layers of the organic thin film layer containing the blue light emitting material according to the present invention to provide a blue organic electroluminescent device of high luminous efficiency while maintaining the conjugation effect and thermal stability of the existing blue material For the purpose of

1 is a structural diagram of a general organic electroluminescent device.

<Explanation of symbols for the main parts of the drawings>

1 glass substrate 2 anode

3: hole injection layer 4: hole transport layer

5: light emitting layer 6: electron transport layer

7: electron injection layer 8: cathode

In order to achieve the above object, the present invention provides a blue light emitting compound for heterocyclic-containing organic electroluminescent device represented by the following formula (1).

[Formula 1]

Wherein X represents O or S,

R ₁ and R ₂ each represent H or —CH ₂ CH ₃ .

The present invention also provides a method for preparing the compound of Formula 1.

Compound of Formula 1 is

1) reacting 9,10-dimethylanthracene with N-bromosuccinimide to yield 9,10-dibromomethylanthracene;

2) reacting the obtained 9,10-dibromomethylanthracene with triethylphosphite to obtain 9,10-bis [(diethoxyphosphoryl) methyl] anthracene; And

3) reacting 9,10-bis [(diethoxyphosphoryl) methyl] anthracene with a 2-thiophenecaraldehyde derivative or a 2-furancarboaldehyde derivative of the following Formula 2 to obtain a desired compound of Formula 1 It can be prepared by.

Wherein X represents O or S,

R represents H or -CH ₂ CH ₃ .

To summarize the manufacturing process is shown in Scheme 1.

In the above reaction scheme, the reaction temperature in the first step is 20 ℃ to 100 ℃, preferably 50 ℃ to 60 ℃, the reaction time is 2 hours to 8 hours, preferably 3 hours to 4 hours, chemical as a solvent Conventional organic solvents used in the reaction may be used, but preferably dichloromethane, carbon tetrachloride, hexane, and the like, and more preferably carbon tetrachloride may be used. N-bromosuccinimide is used for allylzyl bromination and may be used directly with bromine, but there is a risk of bromination to anthracene. 2,2'-azobisisobutyronitrile is used as an initiator of the free radical reaction and hydroperoxide may be used. In addition, it is preferable that the usage-amount of each compound turns into a molar ratio of 9, 10- dimethyl anthracene and N-bromosuccinimide about 1 to 2.3.

The reaction temperature in the second step is 25 ℃ to 160 ℃, preferably 110 ℃ to 150 ℃, the reaction time is 16 hours to 30 hours, preferably 20 hours to 24 hours, used as a solvent for the chemical reaction Ordinary organic solvents may be used, but preferably toluene, tetrahydrofuran, N, N'-dimethylformamide, and the like, and more preferably toluene may be used. In addition, it is preferable that the usage-amount of each compound becomes about 1 to 4 for 9,10- dibromomethyl anthracene and a triethoxy phosphite in molar ratio.

The reaction temperature in the third stage is 0 ° C. to 70 ° C., preferably 25 ° C. to 35 ° C., and the reaction time is 30 minutes to 6 hours, preferably 2 hours to 3 hours, and the solvent is used for chemical reaction. Ordinary organic solvents may be used, but preferably alcohols (methyl alcohol, ethyl alcohol, isopropyl alcohol, butyl alcohol, etc.), 1,4-dioxane, dichloromethane, tetrahydrofuran, and the like. More preferably tetrahydrofuran can be used. In addition, t-BuOK is used for a base catalyst and may use substances, such as sodium chloride, potassium chloride, sodium amide, sodium hydride, and the like.

Representative examples of the compound of Formula 1 are specifically illustrated below. However, the present invention is not limited to the following representative examples.

The present invention also relates to an organic electroluminescent device containing the compound of Formula 1, more particularly an organic electroluminescent device in which an organic thin film layer including a light emitting region is provided between a first electrode (anode) and a second electrode (cathode). The organic electroluminescent device according to claim 1, wherein at least one of the constituent layers of the organic thin film layer contains a blue light emitting material according to the present invention.

The compound of Formula 1 used in the present invention may be used alone in any of the above organic thin film layers, and may be used as a host having other materials as a dopant in these layers, or may be plated with other hole transport materials, light emitting materials, electron transport materials, or the like. May be doped as a trap. Preferably, the compounds according to the invention are used as dopants or hosts in the light emitting layer.

Preferred compounds that can be used as dopants and / or hosts with the compounds of Formula 1 of the present invention in the devices of the present invention include compounds of Formula 3 and compounds of Formula 4, which are the subject of the same application of the present application. .

Wherein X represents O or S,

R ₁ , R ₂ , R ₃ and R ₄ represent H, —CH ₃ or —C (CH ₃ ) ₃ , respectively.

Wherein Ar is , or Indicates

R ₁ and R ₂ represent H, —CH ₃ or —C (CH ₃ ) ₃ .

Various embodiments are possible for the organic electroluminescent device produced using the blue light emitting material of the present invention. Basically, the light emitting layer is sandwiched between the pair of electrodes (anode and cathode) (not necessarily required), and a hole injection layer and / or an electron transport layer and / or an electron injection layer and / or an electron transport layer may be added as necessary. Insert it. Specific examples of the structure include (1) anode / light emitting layer / cathode, (2) anode / hole transporting layer / light emitting layer / cathode, (3) anode / hole transporting layer / electron transporting layer / cathode, (4) anode / hole injection Layer / hole transport layer / light emitting layer / cathode, (5) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode, (6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode And (7) anode / hole injection layer / light emitting layer / electron injection layer / cathode. It is preferable that each element which has the above-mentioned structure is supported by a board | substrate, respectively. There is no particular limitation on the substrate, and those commonly used in organic electroluminescent devices may be used, for example, glass, transparent plastic, quartz, and the like.

Each layer constituting the organic electroluminescent element of the present invention can be formed by thinning by applying a known method, such as a vapor deposition method, a spin coating method, a casting method or the like, to a material which should constitute each layer.

The film thickness of each of the layers thus formed, for example, the light emitting layer, is not particularly limited and can be appropriately selected depending on the situation.

As the anode in the organic electroluminescent device of the present invention, a metal, an alloy, an electrically conductive compound having a large work function of 4.0 eV or more, or a mixture thereof can be used as the electrode material. Examples of such electrode materials include conductive transparent or opaque materials such as ITO, SnO ₂ , ZnO, and Au.

In addition, the anode can be produced by forming a thin film by performing a method such as deposition or sputtering of the electrode material described above.

On the other hand, as the cathode, metals, alloys, electroconductive compounds, and mixtures thereof having a work function of 4.2 eV or less can be used as the electrode material. Examples of such electrode materials include calcium, magnesium, lithium, aluminum, magnesium alloys, lithium alloys, aluminum alloys, aluminum / lithium mixtures, magnesium / silver mixtures, indium and the like.

The cathode can be produced by forming a thin film by applying a method such as vapor deposition or sputtering to these electrode materials. In addition, the sheet resistance as the electrode is preferably set to several hundred? / Mm or less, and the film thickness is usually selected in the range of 10 nm to 1 m, preferably 50 to 200 nm.

In the organic electroluminescent device of the present invention, it is preferable that one or both of the anode and the cathode are made transparent or translucent, and the light emission is transmitted to improve the light extraction effect.

Other hole injection materials and hole transport materials that can be used in the organic electroluminescent device of the present invention include those conventionally commonly used as hole charge transport materials in photoconductive materials, or hole injection layers of organic electroluminescent devices, and Any of known materials used for the hole transport layer may be selected and used.

The electron transport layer in the organic electroluminescent device of the present invention contains an electron transport compound and has a function of transferring electrons injected from the cathode to the light emitting layer. There is no restriction | limiting in particular about such an electron transfer compound, Arbitrary thing can be selected and used out of a conventionally well-known compound.

Next, an example of a method suitable for producing the organic electroluminescent element of the present invention based on the above-described configuration (6) will be described with reference to FIG.

First, the anode 2 is formed on the transparent substrate 1 by a method such as sputtering, and the hole injection layer 3 and the hole transport layer 4 are sequentially vacuum deposited on the anode. After forming the organic light emitting layer 5 and the electron transport layer 6 on the hole transport layer 4 again by vacuum deposition, an electron injection layer 7 and a cathode 8 are formed on the electron transport layer 6.

The light emitting layer 5 may be a light emitting layer formed by doping a host of a compound of Formula 1 of the present invention as a dopant, or a single light emitting layer consisting of only Formula 1.

As the material of the anode 2 mentioned above, ITO (In ₂ O ₃ + SnO ₂ ) or IZO (In ₂ O ₃ + ZnO) may be generally used. As the material of the hole injection layer 3, copper phthalocyanine ( copper (II) phthalocyanine) is used. As the hole transport layer 4, triphenylamine or diphenylamine derivatives such as NPD (N, N-di (naphthalen-1-yl) -N, N'-diphenylbenzidine) can be used, and the host material of the light emitting layer 5 can be used. BAlq (Bis- (2-methyl-8-quinolinolato) -4- (phenyl-phenolato) -aluminium (III)) may be used. In addition, Alq3 can be used as the electron transport layer 6 because of its excellent electron transport properties, and another material that can be used as the electron transport layer 6 is 2- (4-non-phenyl) -5- (4-tert. Oxadiazole and triazole derivatives such as -butylphenyl) -1,3,4-oxadiazole. Alkali metal (Cs, Rb, K, Na, Li) derivatives (Li ₂ O, etc.) may be used as the material of the electron injection layer, and Mg / Ag, Al, Al / Li, Al / Nd as the cathode material. Etc. are possible.

Hereinafter, synthesis examples of the compound of Formula 1 of the present invention and organic electroluminescent device to which the compound is applied will be described in detail in the following Synthesis Examples and Examples, but the present invention is not limited thereto. It can be carried out in various ways within the scope of the invention described in the appended claims.

Synthesis Example

Synthesis Example 1

Synthesis of 9,10-bis [(thiophen-2-yl) vinyl] anthracene

1) Synthesis of 9,10-dibromomethylanthracene

In a 100 mL round bottom flask equipped with a thermometer and a cooling capacitor, 1 g (4.8 mmole) of 9,10-dimethylanthracene, 1.9 g (10.7 mmol) of N-bromosuccinimide, 0.03 of 2,2'-azobisisobutyronitrile 0.03 After adding g (0.2 mmol), 30 mL of carbon tetrachloride was added thereto and refluxed at 80 ° C. for 3 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure, yellow crystals were dissolved in 20 mL of tetrahydrofuran, and 30 mL of methanol was poured out to precipitate crystals and filtered. Finally, 1.3 g of 9,10-dibromomethylanthracene (3.57 mmol, yield 74%) was obtained.

2) Synthesis of 9,10-bis [(diethoxyphosphoryl) methyl] anthracene

9,10-dibromomethylanthracene in a 100 mL round bottom flask with thermometer and cooling capacitor 1.3g (3.57mmole), triethyl phosphite 2.5mL (14mmole) and toluene 40mL were added, and the mixture was refluxed at 110 ° C for 24 hours. After completion of the reaction, the solvent was concentrated under reduced pressure, and 20 mL of hexane was added to the reaction vessel to precipitate crystals. The resulting white crystals were filtered and dried under reduced pressure. 1.6g (3.34mmole, 94% yield) of final product was obtained.

3) Synthesis of 9,10-bis [(thiophen-2-yl) vinyl] anthracene

In a round bottom flask equipped with a thermometer and a cooling capacitor, 1.6 g (3.34 mmol) of 9,10-bis [(diethoxyphosphoryl) methyl] anthracene and 0.8 g (7.13 mmol) of 2-thiophenecaraldehyde were added to tetrahydro. Dissolve 30 ml of furan. 0.8 g (7.12 mmole) of t-butyloxide is slowly added to the reaction mixture several times, and then stirred at room temperature for 1 hour, and the reaction solution is added to a beaker containing 50 mL of water. The crystals produced at this time are filtered off and washed with 30 mL of methanol. The yellow crystals were dried under reduced pressure to yield 0.5 g (1.27 mmol, 38% yield) of the product. The melting point of the final product was measured at 275 ° C.

Synthesis Example 2

Synthesis of 9,10-bis [(5-ethylthiophen-2-yl) vinyl] anthracene

9,10-bis [(diethoxyphosphoryl) methyl] anthracene 1.6g (3.34mmole) and 5-ethylthiophene-2-carboaldehyde 0.8g (7.13mmole) in a round bottom flask equipped with a thermometer and a cooling capacitor ) Is dissolved in 30 mL of tetrahydrofuran. 0.8 g (7.12 mmole) of t-butyloxide is slowly added to the reaction mixture several times, then stirred at room temperature for 1 hour, and the solvent is distilled under reduced pressure to leave a yellow sticky liquid. The liquid was separated by silica column chromatography using a mixed solvent of ethyl acetate: hexane (1: 8), and the solvent was distilled off under reduced pressure to yield 0.72 g (1.59 mmol, 48% yield) of yellow crystals.

Synthesis Example 3

Synthesis of 9,10-bis [(furan-2-yl) vinyl] anthracene

9,10-bis [(diethoxyphosphoryl) methyl] anthracene 1.6g (3.34mmole) and 2-furancarboaldehyde 0.64g (7.13mmole) were placed in a round bottom flask equipped with a thermometer and a cooling capacitor. Add 30 mL to dissolve. 0.8 g (7.12 mmole) of t-butyloxide is slowly added to the reaction mixture several times, and then stirred at room temperature for 1 hour, and the reaction solution is added to a beaker containing 50 mL of water. The crystals produced at this time are filtered off and washed with 30 mL of methanol. The yellow crystals were dried under reduced pressure to yield 0.64 g (1.50 mmol, 45% yield) of the product.

Synthesis Example 4

Synthesis of 9,10-bis [(5-ethylfuran-2-yl) vinyl] anthracene

9,10-bis [(diethoxyphosphoryl) methyl] anthracene 1.6g (3.34mmole), 5-ethylfuran-2-carboaldehyde 0.89g (7.13mmole) in a round bottom flask equipped with a thermometer and a cooling capacitor Dissolve 30 ml of tetrahydrofuran. 0.8 g (7.12 mmole) of t-butyloxide is slowly added to the reaction mixture several times, then stirred at room temperature for 1 hour, and the solvent is distilled under reduced pressure at room temperature to leave a yellow sticky liquid. The liquid was separated by silica column chromatography using a mixed solvent of ethyl acetate: hexane (1: 8), and the solvent was distilled off under reduced pressure to obtain 0.42 g (1.00 mmol, yield 30%) of yellow crystals.

Other compounds belonging to Formula 1 may be prepared by methods similar to those of Synthesis Examples 1 to 4 above.

EXAMPLE

Example 1

This embodiment is an example in which the organic electroluminescent device is manufactured using the above-described compound of Example 3 as a blue light emitting dopant and BAlq as a host.

First, copper phthalocyanine (CuPc) was vacuum-deposited on the glass on which ultrasonically cleaned ITO was deposited to form a hole injection layer having a thickness of 30 nm. A 50 nm thick film was formed on the hole injection layer using NPD [N, N-di (naphthalen-1-yl) -N, N'-diphenylbenzidine] as a hole transport layer, and then the BAlq (host) 1.0% of the compound (dopant) was doped to form a light emitting layer with a thickness of 30 nm. The electron transport layer (Alq 3; 40 nm), the electron injection layer (Li ₂ O; 25 nm) and the cathode (Mg / Ag; 100 nm) were sequentially vacuum deposited thereon, to fabricate an organic EL device.

Luminescent characteristics were evaluated by applying a forward bias DC voltage to the organic electroluminescent device of Example 1 thus produced. As a result of spectroscopic measurement, a spectrum having an emission peak near 497 nm was obtained. Furthermore, when voltage-luminance measurement was performed, a luminance of 5,000 cd / m ² was obtained at 7.8 V, at which time the efficiency was 1.83 lm / W.

The experimental results of Example 1 are summarized in Table 1 below.

Host material Dopant material Applied voltage (V) Luminance (cd / m ² ) Efficiency (lm / W) spectrum Example 1 BAlq Tue 3 7.8 5,000 1.83 497 nm

The blue light emitting compound of the present invention has a small molecular weight, but the wavelength range of light absorbed and emitted by the compound has a range similar to that of a compound having a large molecular weight connected only by a double bond and a phenyl ring. It is easy to produce a material of high purity. In addition, the organic electroluminescent device to which the blue light emitting compound of the present invention is applied can obtain blue light having high luminous efficiency while maintaining the conjugation effect and thermal stability of the existing blue light emitting material.

Claims (7)

A compound of formula [Formula 1] Wherein X represents O or S, R ₁ and R ₂ each represent H or —CH ₂ CH ₃ . The compound of claim 1, wherein the compound of formula 1 consists of the following groups. 1) reacting 9,10-dimethylanthracene with bromosuccinimide to yield 9,10-dibromomethylanthracene; 2) reacting the obtained 9,10-dibromomethylanthracene with triethylphosphite to obtain 9,10-bis [(diethoxyphosphoryl) methyl] anthracene; And 3) prepared by reacting the obtained 9,10-bis [(diethoxyphosphoryl) methyl] anthracene with 2-thiophenecaraldehyde derivative or 2-furancarboaldehyde derivative A process for preparing a compound of formula 1 as defined in claim 1 or 2. [Formula 2] Wherein X represents O or S, R represents H or -CH ₂ CH ₃ . In an organic electroluminescent device in which an organic thin film layer including a light emitting region is provided between a first electrode (anode) and a second electrode (cathode), at least one layer of the constituent layers of the organic thin film layer is claim 1 or 2. An organic electroluminescent device comprising the compound of formula 1 as defined in The organic electroluminescent device according to claim 4, wherein the organic thin film layer has a multilayer structure of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. The organic electroluminescent device according to claim 5, wherein the compound as claimed in claim 1 or 2 is used as a dopant of the light emitting layer. The organic electroluminescent device according to claim 5, wherein the compound as claimed in claim 1 or 2 is used as a host of the light emitting layer.