KR101800872B1

KR101800872B1 - New material for transporting electron and organic electroluminescent device comprising the same

Info

Publication number: KR101800872B1
Application number: KR1020150056941A
Authority: KR
Inventors: 박상미; 이대희; 박세환; 함주석; 남현국; 장승희; 백용구; 조규오
Original assignee: 주식회사 알파켐
Priority date: 2015-04-23
Filing date: 2015-04-23
Publication date: 2017-11-24
Also published as: KR20160127187A

Abstract

The present invention relates to a novel electron transport material and an organic electroluminescent device including the same, and an organic electroluminescent device including an electron transport material according to the present invention in an electron transport layer has an excellent electron transporting ability, It has advantages of improving power consumption by inducing high power efficiency even with low driving voltage and long life characteristic.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel electron transport material and an organic electroluminescent device including the same,

The present invention relates to a novel electron transport material and an organic electroluminescent device including the same. More particularly, the present invention relates to a novel diazafluorene derivative (diazafluorene derivative) and an organic electroluminescent device .

The liquid crystal display (LCD) is the most widely used non-light emitting display device at present, and although it consumes less power and is light, the device driving system is complicated, and response time and contrast characteristics are not satisfactory. Recently, research on an organic electroluminescent device, which is attracting attention as a next generation flat panel display, has been actively conducted.

The emission mechanism of the organic electroluminescent device will be described below. The hole injected from the anode to the valance band or HOMO of the HIL is transported through the hole transport layer (HTL) to the emission layer (EML) At the same time, electrons move from the cathode to the light emitting layer through an electron injection layer to form an exciton by bonding with the holes, and the excitons emit light as they fall to the ground state.

The organic electroluminescent device is an active light emitting display device using the above-described phenomenon. The organic electroluminescent device has a light weight structure, simple components and a simple manufacturing process. The organic electroluminescent device has a high viewing angle and a high viewing angle. In addition, it can realize high color purity and moving picture perfectly, and has electric characteristics suitable for portable electronic devices with low power consumption and low voltage driving.

Representative examples of such electron transport materials include aluminum complexes such as Alq3 (tris (8-hydroxyquinoline) aluminum (III)) and Bebq (bis (10-hydroxybenzo- [h] quinolinato) beryllium), beryllium complexes and the like In such a case, there is a problem that the color purity is deteriorated due to light emission by exciton diffusion when used in a blue light emitting device. In addition, TPBI (see structure below) disclosed by Kodak in 1996 and disclosed in U.S. Patent No. 5,645,948 is known as a typical electron transport layer material having an imidazole group. Phenyl benzimidazole group and functionally blocking not only hole transporting ability in the light emitting layer but also stability in practical application.

As described above, in the conventional electron transporting material, it is particularly noteworthy that there is a problem that the driving voltage is merely slightly improved or the driving life of the device is remarkably lowered compared to the contents to be announced. And there is a problem such as deterioration of thermal stability. In addition, since a conventional organic electroluminescent device employs a fluorescent light emitting material, the electron transport layer material, which is a common material, also has a suitable electron mobility suitable for the phosphorescent light emitting material, a low driving Voltage and hole blocking characteristics are required.

Therefore, the present applicant has found that, in order to improve the low thermal stability, high driving voltage and low device lifetime characteristics of the conventional electron transporting material, not only it has excellent device driving lifetime characteristics with low driving voltage, but also has thermal stability, electron mobility and hole blocking characteristics The present invention has been completed to provide an excellent electron transport material and an organic electroluminescent device using the same.

It is an object of the present invention to provide an electron transport material having excellent thermal stability and electron transporting ability and an organic electroluminescent device including the same.

The present invention provides a diazafluorene derivative represented by the following formula (1), which is excellent in thermal stability and electron transporting ability, and provides an organic electroluminescent device having excellent luminous efficiency and low voltage driving capability.

[Chemical Formula 1]

[In the above formula (1)

R ₁ and R ₂ are each independently hydrogen, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl or _{-N (R 11) (R 12} ) and, R ₁₁ and R ₁₂ (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl, wherein the alkyl, aryl and heteroaryl of R ₁ and R ₂ are each independently (C6-C30) aryl, (C6-C30) aryl (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, (C3-C30) cycloalkyl, (C6-C30) aryl, (C3-C30) heteroaryl, (C3-C30) heteroaryl substituted with (C1- (C1-C30) alkylsilyl, di (C1-C30) alkylthio, (C1-C30) alkylthio, (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, nitro, and hydroxy, and said heteroaryl is optionally substituted with one or more substituents selected from the group consisting of B, N, O, S, P (= O), Si and P.

The electron transport material according to the present invention was able to improve thermal stability and solubility in solvents by introducing four phenyl groups into dimethyl azafluorene, and by having a low LUMO energy level, it was possible to improve the electron transporting ability.

Further, the organic electroluminescent device employing the electron transporting material according to the present invention in the electron transporting layer has excellent electron transporting ability and thus can have not only high luminous efficiency, but also excellent lifetime characteristics.

FIG. 1 is a graph showing the efficiency (cd / A) vs. luminance (cd / m 2) of the organic electroluminescence device manufactured in Examples 4 to 6 and Comparative Example 1.

The novel electron transport material and the organic electroluminescent device including the same according to the present invention will be described below. However, unless otherwise defined in technical terms and scientific terms used herein, And the description of known functions and configurations which may unnecessarily obscure the gist of the present invention will be omitted in the following description.

In order to achieve the above object, the present invention provides an electron transport material represented by the following formula (1).

[Chemical Formula 1]

[In the above formula (1)

The electron transport material according to the present invention includes 4 phenyl groups in 9,9-dimethyl-4,5-diazafluorene, Can be easily applied in a deposition or solution process due to its solubility, is excellent in thermal stability, has a high electron density, and can exhibit high luminous efficiency.

&Quot; Alkyl " and other " alkyl " moieties described herein include both straight chain and branched forms.

&Quot; Aryl " according to the present invention is an organic radical derived from aromatic hydrocarbons by the removal of one hydrogen, in which each ring is optionally substituted by a single or fused ring containing from 4 to 7, preferably 5 or 6 ring atoms A ring system, and a form in which a plurality of aryls are connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, But are not limited thereto.

&Quot; Heteroaryl " as used herein includes 1-4 heteroatoms selected from B, N, O, S. P (= O), Si and P as aromatic ring skeletal atoms, and the remaining aromatic ring backbone atoms are carbon Means a 5 to 6 membered monocyclic heteroaryl and a polycyclic heteroaryl condensed with at least one benzene ring and may be partially saturated. The heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected to a single bond. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, Monocyclic heteroaryl such as tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoiso Benzothiazolyl, benzothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, (Such as pyridyl N-oxide, quinolyl N-oxide), polycyclic heteroaryls such as benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, Quaternary salts and the like.

According to an embodiment of the present invention, R ₁ and R ₂ in Formula 1 are each independently selected from the group consisting of (C6-C30) aryl, (C3-C30) heteroaryl, (C1-C30) alkyl, halogen, (C1-C30) alkoxy, (C6-C30) aryl, and (C3-C30) arylamino, wherein said aryl and heteroaryl are each independently selected from Heteroaryl, and the like, but is not limited thereto.

The electron transporting material according to an exemplary embodiment of the present invention can be easily transferred electronically, has an excellent luminous efficiency due to an improved electron transporting ability, But are not limited thereto.

(2)

(3)

[In the above formulas (2) and (3)

Wherein R ₁ and R ₂ are each independently (C6-C30) aryl, (C3-C30) heteroaryl, mono (C6-C30) arylamino or di (C6-C30) heteroaryl, and (C3-C30) heteroaryl, each independently selected from the group consisting of (C1-C30) alkyl, halo And said heteroaryl comprises at least one heteroatom selected from B, N, O, S, P (= O), Si and P.

Preferably, R ₁ and R ₂ in formulas (1) to (3) are independently selected from the following structures, but are not limited thereto.

[In the above structure,

R ₁₁ and R ₁₂ are each independently hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl.

At this time, R ₁₁ and R ₁₂ of Formula 1 are each independently hydrogen, methyl, ethyl, n - propyl, i - propyl, n - butyl, i - butyl, s - butyl, t - butyl, n - pentyl, i -pentyl, s-pentyl, n-hexyl, i-hexyl, s-hexyl, n- heptyl, n- octyl, n- nonyl, n- decyl, i-decyl, n- undecyl, n- dodecyl, n N-pentadecyl, n-hexadecyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, N - propyl, i - propyl, n - butyl, i - butyl, s - butyl, isobutyl, sec - butyl, t -butyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, or indenyl.

More preferably, the formula (1) may be an electron transporting material selected from the following structures, but is not limited thereto.

The method of preparing an electron transporting material according to the present invention is illustrated by the following Reaction Schemes 1 and 2, but it is not limited thereto and can be prepared through a known organic reaction.

[Reaction Scheme 1]

[Reaction Scheme 2]

[In the above Reaction Schemes 1 and 2,

R ₁ is the same as defined in the above formula (1);

X ₁ and X ₂ are each independently halogen.]

The present invention provides an organic electroluminescent device comprising an electron transporting material represented by the following general formula (1).

[Chemical Formula 1]

[In the above formula (1)

The present invention includes an organic thin film material for an organic electroluminescence device including an electron transporting material represented by the above formula (1) in an electron transporting layer, and any material for an organic electroluminescence device containing the same may be included in the present invention.

An organic electroluminescent device according to an embodiment of the present invention will now be described in more detail with reference to the accompanying drawings.

The organic electroluminescent device according to an embodiment of the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, and the organic material layer may include the electron transport material. The organic material layer may include a light emitting layer, an injection layer, a blocking layer, and a transport layer. The organic electroluminescent device according to the present invention includes an electron transport layer including the electron transport material represented by Formula 1. The material used for the organic material layer may be any material that can be recognized by those skilled in the art, and the method for manufacturing the organic electroluminescent device of the present invention is not limited and can be manufactured by any ordinary method .

The first electrode may be an anode layer, and is an electrode for injecting holes into the hole injection layer. Therefore, the material for forming the anode layer is not limited as long as the anode layer is provided with a characteristic. Specific examples of the material for forming the anode layer 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; A conductive polymer such as polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, poly (3-methylthiophene), and polyphenylene sulfide. Further, the anode layer may be formed of only one type of the above-described materials, or may be formed of a mixture of a plurality of materials, and a multi-layer structure composed of a plurality of layers of the same composition or different compositions may be formed.

The organic material layer may include a hole injection layer (HIL), a hole blocking layer (HBL), a hole transport layer (HTL), a light emitting layer, an electron transport layer (ETL), an electron injection layer And can be omitted if necessary.

The hole injection layer (HIL) may be formed on the first electrode by various methods such as a vacuum deposition method, a spin coating method, a casting method, an LB method, etc., and may be formed using PEDOT / PSS or copper phthalocyanine (CuPc) It is preferably deposited in the range of 100 to 600 ANGSTROM using a material such as 4 ', 4 "-tris (3-methylphenylphenylamino) tri phenylamine (m-MTDATA).

Also, the hole transport layer (HTL) may be formed by using 4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl (NPD) or N, N'- -methyl phenyl) -1,1'-biphenyl-4,4'-diamine (TPD).

The light emitting layer according to an embodiment of the present invention may be a light emitting layer exhibiting fluorescence or phosphorescence and is not particularly limited as long as it is a substance such as a fluorescent host, a fluorescent dopant, a phosphorescent host, or a phosphorescent dopant applied to an organic electroluminescent device .

The electron transporting material according to the present invention is included in the electron transport layer (ETL), thereby enhancing the driving voltage of the organic electroluminescent device, exhibiting excellent electron transporting ability, and realizing an organic electroluminescent device having high brightness and long life. The film thickness of the electron transporting layer is not limited, but it is preferable to adjust the thickness within the range of 10 to 1000 angstrom from the viewpoints of preventing the application of a high voltage unnecessarily to the homogeneity of the film or light emission and improving the stability of the luminescent color with respect to the driving current , More preferably in the range of 10 to 800 angstroms, and particularly preferably in the range of 10 to 400 angstroms.

In addition, the electron injection layer may be deposited to a thickness of 100 to 500 ANGSTROM using LIF or LiQ (lithium quinolate), but is not limited thereto.

The electron injecting layer of the present invention may be deposited to a thickness of 100 to 500 Å by using LIF or LiQ (lithium quinolate), but the present invention is not limited thereto. The second electrode (cathode layer) may include Al, Ca, Mg: Ag A metal having a low work function can be used, and preferably Al is preferable.

The organic electroluminescent device according to the present invention can be applied to a display device, the display device can be a display device using a backlight unit, and the organic electroluminescent device can be used as a light source of a backlight unit, And the display device may be an organic electroluminescent display (OLED) or the like, but is not limited thereto.

Hereinafter, the present invention will be better understood by reference to the following examples, and the following examples are for illustrative purposes only and are not intended to limit the scope of protection of the present invention.

(Example 1) Preparation of Compound 3

Step 1. Preparation of Compound 3-A

50 g (509 mmol) of cyclopentane-1,2-dione and 118.9 g (1121 mmol) of benzaldehyde were dissolved in 1280 mL of ethanol, and 61.1 g (1529 mmol) of sodium hydroxide was added thereto at 0 ° C. Lt; / RTI > After stirring at room temperature for 3 hours, the resulting solid was separated by filtration under reduced pressure and washed with methanol. And dried to obtain 75.5 g (yield: 54%) of a yellow solid compound 3-A.

¹ H-NMR (CDCl ₃ )? [Ppm]: 7.52 (m, 6H), 7.38 (m, 6H), 3.32

Step 2. Compound 3-B Manufacturing

300 g (1079 mmol) of 4-bromophenylacyl bromide was slowly added to a 2000 mL 3-necked round bottom flask while stirring 3000 mL of pyridine. After stirring at room temperature for 2 hours, the precipitated solid was separated by filtration under reduced pressure and washed with methanol. 335.2 g (933 mmol) of the obtained compound, 64 g (233 mmol) of the compound 3-A, 71.9 g (933 mmol) of ammonium acetate and 850 mL of methanol were mixed and stirred under reflux for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the precipitated solid was separated by filtration under reduced pressure and washed with methanol to obtain 48.5 g of a white solid compound 3-B (yield: 33%).

^{_{1 H-NMR (CDCl 3)}} δ [ppm]: 7.9 (d, 5H), 7.82 (s, 1H), 7.62 (m, 8H), 7.46 (t, 4H), 7.36 (t, 2H), 3.88 ( s, 2H)

Step 3. Compound 3-C Manufacturing

45 g (71.4 mmol) of the compound 3-B, 19.2 g (171 mmol) of potassium t-butoxide and 900 mL of tetrahydrofuran were mixed in a 2000 mL three-necked round bottom flask and stirred until the mixture was completely dissolved at 0 ° C. Then, 29.1 g (186 mmol) of iodomethane was slowly added thereto. After stirring at room temperature for 4 hours, after completion of the reaction, water was added, extracted with ethyl acetate, treated with anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained solid was recrystallized with hexane to obtain 30.1 g (yield: 65%) of a white solid compound 3-C.

¹ H-NMR (CDCl ₃ )? [Ppm]: 7.9 (d, 4H), 7.8 (s, 2H), 7.62 (m, 8H) s, 6H)

Step 4. Compound 3 Preparation of

25 g (38 mmol) of compound 3-C, 10.2 g (83.5 mmol) of 4-pyridine boronic acid and 400 mL of tetrahydrofuran are added to a 1000 mL three-necked round bottom flask. 0.88 g (0.76 mmol) of tetrakis (triphenylphosphine) palladium (0) was added, 150 ml of a 1M potassium carbonate aqueous solution was added, and the mixture was heated to reflux. After about 12 hours of reaction, the reaction is cooled to room temperature. Extracted with water and ethyl acetate, treated with anhydrous magnesium sulfate, and concentrated under reduced pressure. After concentration, the mixture was separated with a silica gel column (hexane: methylene chloride = 1: 1) to obtain a white solid compound 3 16.6 g (Yield: 67%) was obtained.

¹ H-NMR (CDCl ₃ )? [Ppm]: 8.75 (d, 4H), 8.19 (d, 4H), 7.82 (m, 6H) m, 2 H), 1.67 (s, 6 H)

MALDI-TOF MS: m / z 654.8, cal. 654.01

(Example 2) Preparation of Compound 7

Step 1. Compound 7-A Manufacturing

30 g (128 mmol) of the compound 3-C was added to a 1000 mL three-necked round bottom flask and 71.9 g (283 mmol) of bis (pinacolato) diboron was added thereto. Then 600 mL of 1,4- . Dichloropalladium (II) and chloromethane complex (4.2 g, 5.1 mmol) were added, and 50.5 g (514 mmol) of potassium acetate was added thereto, followed by heating and stirring with refluxing . After about 12 hours of reaction, the reaction is cooled to room temperature. Extraction is carried out with a saturated aqueous solution of sodium chloride and ethyl acetate. Dried with anhydrous magnesium sulfate, treated with activated charcoal, filtered through celite, and then concentrated under reduced pressure. The resulting solid was recrystallized from hexane to obtain 20.9 g of a white solid compound 7-A (yield: 58%).

¹ H-NMR (CDCl ₃ )? [Ppm]: 8.12 (d, 4H), 7.93 (s, 2H), 7.54 (m, 8H), 7.46 s, 6H), 1.38 (s, 12H), 1.32 (s, 12H)

Step 2. Preparation of compound 7

20 g (26.6 mmol) of the compound 7-A, 8.34 g (58.5 mmol) of 2-chloro-4,6-dimethylpyrimidine and 350 mL of tetrahydrofuran are added to a 1000 mL three-necked round bottom flask. 0.31 g (0.27 mmol) of tetrakis (triphenylphosphine) palladium (0) was added thereto, and 100 ml of a 1M potassium carbonate aqueous solution was added and the mixture was heated to reflux. After about 12 hours of reaction, the reaction is cooled to room temperature. Extract with water and ethyl acetate and treat with anhydrous magnesium sulfate. After concentration, the mixture was separated with a silica gel column (hexane: methylene chloride = 3: 1) to obtain a white solid compound 7 11.6 g (Yield: 61%) was obtained.

¹ H-NMR (CDCl ₃ )? [Ppm]: 8.19 (d, 4H), 7.87 (m, 6H), 7.63 s, 2H), 2.6 (s, 12H), 1.67 (s, 6H)

MALDI-TOF MS: m / z 712.88, cal. 712.16

(Example 3) Preparation of Compound 9

Step 1. Preparation of compound 9-A

100 g (151 mmol) of the compound 3-C, 18.8 g (154 mmol) of phenyl boronic acid and 1500 mL of toluene are added to a 1000 mL three-necked round bottom flask. 1.76 g (1.52 mmol) of tetrakis (triphenylphosphine) palladium (0) was added, 500 ml of a 1M potassium carbonate aqueous solution was added, and the mixture was heated to reflux. After about 12 hours of reaction, the reaction is cooled to room temperature. Extracted with water and ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. After concentration, the mixture was separated with a silica gel column (hexane: methylene chloride = 10: 1) to obtain a white solid compound 9-A 41.8 g (yield: 42%) was obtained.

¹ H-NMR (CDCl ₃ )? [Ppm]: 8.19 (d, 2H), 7.9 (d, 2H), 7.82 (m, 4H) m, 3 H), 1.67 (s, 6 H)

Step 2. Compound 9-B Manufacturing

40 g (61 mmol) of the compound 9-A was added to a 1000 mL three-necked round bottom flask, and then 15.8 g (62 mmol) of bis (pinacolato) diboron were added, and 600 mL of 1,4- . 1 g (1.2 mmol) of 1,1'-bis [(diphenylphosphino) ferrocene] dichloropalladium (II) and chloromethane complex was added, and 11.9 g (122 mmol) of potassium acetate was added thereto, . After about 12 hours of reaction, the reaction is cooled to room temperature. The reaction mixture was extracted with saturated aqueous sodium chloride and ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. After concentration, the mixture was separated by a silica gel column (hexane: ethyl acetate = 10: 1) and the resulting solid was recrystallized from methanol to obtain 13.5 g of white solid compound 9-B (yield: 79%).

^{_{1 H-NMR (CDCl 3)}} δ [ppm]: 8.33 (d, 2H), 8.14 (d, 2H), 7.82 (m, 4H), 7.62 (m, 8H), 7.47 (t, 6H), 7.38 ( m, 3H), 1.67 (s, 6H), 1.38 (s, 12H)

Step 3. Compound Production of 9

5 g (18.7 mmol) of the compound 3-B, 13.3 g (19.1 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, and tetrahydrofuran 100 mL. 0.22 g (0.19 mmol) of tetrakis (triphenylphosphine) palladium (0) was added, 30 ml of a 1M potassium carbonate aqueous solution was added, and the mixture was heated to reflux. After about 12 hours of reaction, the reaction is cooled to room temperature. Extracted with water and ethyl acetate, treated with anhydrous magnesium sulfate, filtered through celite, and concentrated under reduced pressure. The concentrate was then separated into a silica gel column (hexane: methylene chloride = 1: 1) to obtain a white solid compound 9 10.3 g (Yield: 68%) was obtained.

¹ H-NMR (CDCl ₃ )? [Ppm]: 8.2 (m, 4H), 7.97 (d, 2H), 7.88-7.78 (m, 8H), 7.65 ), 1.67 (s, 6H)

MALDI-TOF MS: m / z 807.98, cal. 807.36

(Example 4) Production of organic electroluminescence device using compound 3 according to the present invention

A transparent anode made of indium tin oxide (ITO) having a film thickness of 1500 ANGSTROM was formed on a glass substrate having a size of 25 mm x 25 mm x 0.7 mm. The glass substrate was ultrasonically cleaned in distilled water containing detergent for 10 minutes and washed once in distilled water for 10 minutes. After the distilled water was cleaned, the substrate was ultrasonically cleaned by using a solvent of isopropyl alcohol, acetone, and methanol for 10 minutes sequentially and dried. Next, after dry cleaning using oxygen / argon plasma, a glass substrate having a transparent electrode line was mounted on a substrate holder of a vacuum evaporation apparatus, and on the surface where a transparent electrode line was formed, Was deposited to a thickness of 400 ANGSTROM to form a hole injection layer. HBL was deposited on the hole injection layer to a thickness of 50 ANGSTROM to form a hole blocking layer. Compound 3 according to the present invention was then deposited to a thickness of 300 ANGSTROM to form a hole transport layer. Next, a light emitting layer was formed by depositing 6 wt% of the following compound ADN: BD02 as a luminescent host so as to have a thickness of 250 ANGSTROM, and Liq (lithium quinolate) was deposited thereon to form an electron injecting layer. Metal aluminum was deposited on the Liq film to form a metal cathode, thereby fabricating an organic electroluminescent device.

The electroluminescent characteristics and the basic properties of the thus prepared organic electroluminescent device were measured by applying a voltage of 0 to 15 V. The results are shown in Table 1 and FIG. 1 below .

1) Device evaluation

The device characteristics of the organic EL device manufactured in Example 4 were measured according to the voltage change. The measurement was performed by increasing the voltage from 0 V to 15 V at constant intervals and using a Polaronix M6100 LAB OLED IVL Test system of McScience Co. and CS-2000 of KONICA MINOLTA Co., Current density, luminance, luminous efficiency and color coordinate values were measured.

(Example 5) Production of organic electroluminescence device using compound 7 according to the present invention

An organic electroluminescent device was fabricated under the same conditions as in Example 4 except that the compound 7 was used instead of the compound 3 as the luminescent material in Example 4. The electroluminescent characteristics and the basic physical property measurement results are shown in Table 1 below .

(Example 6) Production of organic electroluminescence device using compound 9 according to the present invention

An organic electroluminescent device was fabricated under the same conditions as in Example 4 except that the compound 9 was used instead of the compound 3 as the luminescent material in Example 4. The electroluminescent characteristics and the measurement results of the basic physical properties are shown in Table 1 .

(Comparative Example 1) Production of an organic electroluminescence device using the compound HTL

An organic electroluminescence device was fabricated under the same conditions as in Example 4 except that the compound HTL was used instead of the compound 3 as the electron transporting material in Example 4. The electroluminescence characteristics and the basic physical property measurement results Respectively.

As shown in Table 1, it was confirmed that the organic electroluminescent device comprising the electron transporting material of the present invention in the electron transporting layer exhibited superior characteristics to the conventional materials. It can be seen that not only has excellent luminance and high efficiency, but also high lifetime characteristics.

Claims

An electron transporting material represented by the following formula (1);
[Chemical Formula 1]

[In the above formula (1)
R ₁ and R ₂ are each independently a (C6-C30) aryl, (C3-C30) heteroaryl or _{-N (R 11) (R 12} ) and, R ₁₁ and R ₁₂ is (C1-C30), each independently (C6-C30) aryl and (C3-C30) heteroaryl, wherein the aryl and heteroaryl of R ₁ and R ₂ are each independently selected from the group consisting of (C 1 -C 30) alkyl, C30) heteroaryl, wherein said heteroaryl comprises at least one heteroatom selected from B, N, O, S, P (= O), Si and P; ]

The method according to claim 1,
Wherein R ₁ and R ₂ are each independently (C 6 -C 30) aryl, (C 3 -C 30) heteroaryl, mono (C 6 -C 30) arylamino or di (C 6 -C 30) arylamino, Wherein each heteroaryl is independently selected from the group consisting of (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, (C1-C30) alkoxy, (C6-C30) aryl and (C3-C30) An electron transport material that can be further substituted with one or more.

3. The method of claim 2,
Wherein R ₁ and R ₂ in Formula 1 are each independently selected from the following structures;

[In the above structure,
R ₁₁ and R ₁₂ are each independently hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl.

The method of claim 3,
R ₁₁ and R ₁₂ in the formula (1) is hydrogen, methyl, ethyl, n - propyl, i - propyl, n - butyl, i - butyl, s - butyl, t - butyl, n - pentyl, i - pentyl, s - pentyl, n - hexyl, i - hexyl, s - hexyl, n- heptyl, n- octyl, n- nonyl, n- decyl, i - decyl, n- undecyl, n- dodecyl, n- tridecyl, n Naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, , Naphthacenyl, and fluoranthenyl. &Lt; / RTI >

The method according to claim 1,
Wherein the formula (1) is selected from the following structures.

An organic electroluminescent device comprising an electron transporting material represented by the following formula (1):
[Chemical Formula 1]

The method according to claim 6,
The organic electroluminescent device includes a first electrode; A second electrode; And at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes an electron transporting layer containing the electron transporting material.