KR100961781B1 - n-type organic semiconductor compound and organic electroluminescent device using the same - Google Patents

Abstract

An n-type organic semiconductor compound and an organic light emitting device using the semiconductor compound are provided. More specifically, it is related with the compound represented by following formula (1), and the organic electroluminescent element containing the said compound.

The n-type organic semiconductor compound according to the present invention can provide an organic light emitting device having excellent power efficiency and luminous efficiency, and an organic thin film transistor, a photovoltaic cell or an organic photoconductor as well as the organic light emitting device. It is possible to apply to various fields that can use organic semiconductor materials such as OPC).

Description

n-type organic semiconductor compound and organic electroluminescent device using the same

The present invention relates to an n-type organic semiconductor compound and an organic light emitting device using the same, and more particularly, to an n-type organic semiconductor compound having excellent power efficiency and luminous efficiency and an organic light emitting device using the same.

Recently, with the development of the information and communication industry, the demand for organic light emitting diodes is rapidly increasing. Looking at the principle of the organic light emitting device, when power is supplied to the organic light emitting device, electrons move and current flows. At the cathode, electrons (-) move to the light emitting layer with the help of the electron transport layer, and holes at the anode are relatively positive (+ Concept, the state in which the electrons escaped) is moved to the light emitting layer with the help of the hole transport layer. Electrons and holes encountered in the light emitting layer, which is an organic material, generate excitons with high energy. Excitons fall to low energy and generate light.

In such an organic light emitting device, the hole transport layer is a material that facilitates the injection of holes from the anode, ultimately improves the power efficiency of the device and increases the life of the device. In order to lower the hole injection barrier, the ionization energy with the anode should be similar, and the interfacial adhesion between the anode and the anode should be high, and in order to increase the external quantum efficiency, absorption in the visible region should not be possible. The hole transport material of the hole transport layer not only transports holes easily but also enhances the probability of forming exciton by binding electrons to the light emitting region. Therefore, the hole transport material of the hole transport layer is known to have a high hole mobility in addition to the basic properties mentioned above. have. As the material of this system, aromatic amines are commonly used to stabilize the cationic radicals generated when holes are injected.

The electron transport layer also facilitates electron injection from the cathode, thereby improving the power efficiency and luminous efficiency of the device. As a material of the electron transport layer, a metal compound that can easily accept electrons when electrons are injected from the cathode is mainly used. The most known of these metal compounds is Alq₃, which has excellent stability and high electron affinity.

In addition to the Alq₃, the materials presented as electron transport materials include flavone derivatives, Sanso's germanium and silicon cyclopentadiene derivatives published by Sanyo (Japanese Patent Publication No. 1998-017860). Japanese Patent Application Laid-Open No. 1999-087067), PBD (2- (4-biphenylyl) -5- (4-t-butylphenyl) -1, which is an oxydiazole derivative used as a blue light emitting material, 3,4-oxydiazole) is also proposed as an electron transport material. However, the materials have a high driving voltage, easy crystallization, and a problem of low stability of the thin film. Thus, the practical electron transport material is about Alq ₃ . However, when Alq ₃ is used as the electron transport material, green light emission of Alq ₃ is observed when the driving voltage is increased to obtain high luminance, and in particular, when the blue light is emitted, the luminous efficiency is lowered as the color purity is lowered.

Accordingly, a first object of the present invention for solving the above problems is to provide an n-type organic semiconductor compound having excellent power efficiency and luminous efficiency and a long lifetime.

A second object of the present invention is to provide an organic light emitting device using the n-type semiconductor compound.

In order to solve the first problem, the present invention provides an n-type organic semiconductor compound of the formula (1).

Wherein R ₁ and R ₂ are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 19 carbon atoms, and the substituted aryl group or heteroaryl group has 1 to 10 carbon atoms Alkyl group, alkoxy group of 1 to 10 carbon atoms, cyano group, alkylamino group of 1 to 10 carbon atoms, alkylsilyl group of 1 to 10 carbon atoms, halogen group, aryl group of 6 to 10 carbon atoms, aryloxy group of 6 to 10 carbon atoms , An arylamino group having 6 to 10 carbon atoms, an arylsilyl group having 6 to 10 carbon atoms, a heteroaryl group having 3 to 19 carbon atoms, and at least one substituent selected from the group consisting of hydrogen)

At least one of R ₁ and R ₂ is a substituted or unsubstituted heteroaryl group, and at least one of nitrogen, sulfur, and oxygen may be used as a ring element in addition to carbon.

The organic semiconductor compound may be any one selected from the group represented by the following formula (2).

In order to solve the second problem, the present invention is an anode; Cathode; And an organic light emitting device provided between the anode and the cathode and including a layer containing the above-described organic semiconductor compound. The organic semiconductor compound-containing layer may be an organic light emitting layer or an electron transport layer.

The n-type organic semiconductor compound according to the present invention facilitates the movement of electrons in the organic light emitting device. As a result, the organic light emitting device manufactured by using the n-type organic semiconductor compound has excellent power efficiency and luminous efficiency, and has a long lifetime.

Hereinafter, the present invention will be described in more detail.

The n-type organic semiconductor compound of Chemical Formula 1 has anthracene as a basic skeleton, and a substituent of an aryl group or a heteroaryl group is introduced at positions 2, 7, 9 and 10. As such, anthracene derivatives having an aromatic ring structure as a substituent at positions 2, 7, 9, and 10 have excellent π-π stacking, and in particular, an aryl group or heteroaryl at positions 2, 6, 9, and 10 The n-type organic semiconductor compound of the present invention, which is superior to the substituted anthracene derivative and has excellent π-π stacking, can transport electrons to the light emitting layer more stably and efficiently when electrons are injected from the cathode.

Furthermore, in the present invention, a heteroaryl group having nitrogen, oxygen, sulfur, etc. having excellent electron affinity as a ring component is R ₁ And R ₂ It can be used in at least one of the. Such heteroaryl groups increase the operating characteristics and stability of the n-type organic semiconductor compound in which electrons are used as carriers.

The organic EL device according to the present invention includes at least one layer containing the n-type organic semiconductor compound described above between the anode and the cathode. In this case, the n-type organic semiconductor compound-containing layer may be an organic light emitting layer or an electron transport layer. As described above, since the n-type organic semiconductor compound easily transfers electrons from the cathode of the organic light emitting diode to the light emitting layer, the organic light emitting diode of the present invention using the organic semiconductor compound has excellent power efficiency and luminous efficiency.

The n-type organic semiconductor compound according to the present invention is particularly advantageous when used in the electron transport layer of the organic light emitting device as described above, but besides that, an organic thin film transistor, a photovoltaic cell or an organic photoconductor (OCC), etc. It can be applied to various fields as well.

As described above, the organic light emitting device containing the n-type organic semiconductor compound of the present invention is described in more detail. A hole transport layer (HTL) is further stacked between the anode and the light emitting layer, and the cathode and the organic light emitting layer An electron transport layer (ETL) is additionally stacked between the holes, and the hole transport layer is laminated to facilitate the injection of holes from the anode. The material of the hole transport layer includes electron donor molecules having small ionization potential. Diamine, triamine or tetraamine derivatives mainly based on triphenylamine are used. The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl-[ 1,1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD) and the like can be used. .

A hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material is not particularly limited as long as it is commonly used in the art, for example, CuPc or Starburst type amines listed in 3, TCTA, m-MTDATA, IDE406 (manufactured by Idemitsu Corp.) and the like can be used.

CuPc, TCTA, m -MTDATA

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention provides an opportunity to recombine in the light emitting layer by smoothly transporting electrons supplied from the cathode to the organic light emitting layer and suppressing the movement of holes not bonded to the organic light emitting layer. It plays an increasing role. As the electron transport layer material, the compound represented by Chemical Formula 1 may be used by mixing with one or more other materials, and when used in combination, the material is 10 to 99.9 wt% based on the total weight. The material that can be mixed is not particularly limited as long as it is a material used in the art as an electron transport layer material. For example, Alq3, PBD (2- (4-biphenylyl) -5- (4-t-butylphenyl ) -1,3,4-oxadiazole), TNF (2,4,7-trinitro fluorenone), BND (2,5- (Dinaphth-1-yl) -1,3,4-oxadiaxole) Can be used together

Meanwhile, an electron injection layer (EIL) may be further stacked on the upper portion of the electron transport layer to facilitate the injection of electrons from the cathode and ultimately improve the power efficiency. If it is commonly used in the industry can be used without particular limitation, for example, materials such as LiF, NaCl, CsF, Li ₂ O, BaO and the like can be used.

As light emitting materials for organic electroluminescent devices, chelates such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, distyrylarylene derivatives, oxadiazole derivatives and the like are known. However, when only one material is used as a light emitting material, the maximum light emission wavelength is shifted to a long wavelength due to intermolecular interactions, and mound peaks are generated at long wavelengths, resulting in inferior color purity or inefficiency due to light emission attenuation effect caused by intermolecular interactions. In order to increase luminous efficiency through increase and energy transfer, a host / dopant system is frequently used. In such a host, an aromatic compound such as an anthracene-based may be used, and various dopants may be used according to a color to be emitted. Representative examples include C-545T (10- (2-Benzothiazolyl) -1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-benzo [l] pyrano [6,7, 8, ij] quinolizin-11-one), bis (2- (4,6-difluorophenyl) pyridyl-N, C2 ') iridium (III) picolinate

(bis (2- (4,6-difluorophenyl) pyridyl-N, C2 ') iridium (III) picolinate (Firpic)).

1 is a cross-sectional view showing the structure of the organic electroluminescent device of the present invention described above.

The organic light emitting display device according to the present invention includes a substrate 10, an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, if necessary, hole injection The layer 30 and the electron injection layer 70 may be further included. In addition, a middle layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to Figure 1 with respect to the organic light emitting device and a method of manufacturing the present invention will be described.

First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, transparent and conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO) are used as the anode electrode material. The hole injection layer 30 may be selectively formed by vacuum thermal evaporation or spin coating of the hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30. Subsequently, the organic light emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method. can do. The hole blocking layer serves to prevent such a problem by using a material having a very low HOMO level when the hole is introduced into the cathode through the organic light emitting layer to reduce the lifetime and efficiency of the device. In this case, the hole blocking material used is not particularly limited, but should have an ion transporting potential and have a higher ionization potential than the light emitting compound. Typically, BAlq (1,1'-Bisphenyl-4-olato) bis (2-methyl-8- quinolinplate, N1,08) Aluminum (II)), BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), TPBI (1,3,5-tris (N-phenylbenzimidazol-2-yl ) benzene) and the like can be used. After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is selectively formed, and a metal for forming a cathode is formed on the electron injection layer 70. The organic EL element is completed by vacuum thermal evaporation to form the cathode 80 electrode. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

Hereinafter, the present invention will be described in more detail with reference to preferred examples, but the present invention is not limited thereto.

Example 1

Example 1- (1)

2,7- Dibromo -9,10- Di (4'-biphenyl) anthracene [ 2,7- Dibromo -9,10-di (4'-biphenyl) anthracene ] Synthesis of

In a round bottom flask, 49.7 g (0.21 mol) of 4'-bromobiphenyl (4'-bromobiphenyl) and 600 ml of THF (Tetrahydrofuran) were put in a nitrogen atmosphere, and then cooled to -78 ° C while stirring. 133 ml (0.21 mol) of 1.6 M n-butyllithium (n-BuLi) was slowly injected into the reaction mixture, and the mixture was stirred at the same temperature for 1 hour or more, followed by 2,7-dibromoanthraquinone (2,7-dibromoanthraquinone). ) 30.0 g (0.08 mol) was added. The reaction product was heated to room temperature, and after 3 hours, the reaction was confirmed by TLC (Thin layer chromatography) to terminate the reaction. The reaction was separated using an aqueous MC (methylene chloride) / NH ₄ Cl solution, the MC layer was washed twice with water and the organic layer was dried over anhydrous MgSO ₄ . The filtrate was concentrated by filtration to produce crystals. The mixture was washed with a small amount of ethanol and filtered to obtain 48.0 g. Then, 48.0 g (0.07 mol) of the reaction product was put into a round bottom flask, followed by KI 118.1 g (0.71 mol), NaH ₂ PO ₂ -H ₂ O 125.2 g (1.42 mol), and acetic acid (2400 ml). The reaction was maintained at 110 ^° C. for 3 hours. After completion of the reaction by TLC, the resulting white crystals were cooled by cooling to room temperature. The crystals were washed with excess water and column separated with CH ₂ Cl ₂ alone. After concentration of the separation solution, the crystals were washed with methanol and dried under reduced pressure to obtain 2,7-dibromo-9,10-di (4'-biphenyl) anthracene (2,7-Dibromo-9,10-di 30.0 g (57.1%) of (4'-biphenyl) anthracene) was obtained.

Example 1- (2)

2,7-di (3- Pyridyl ) -9,10- Di (4'-biphenyl) anthracene [ 2,7- Di (3- pyridyl ) -9,10-di (4'-biphenyl) anthracene ] Synthesis of

In a 500 ml round bottom flask, 2,7-dibromo-9,10-di (4'-biphenyl) anthracene (2,7-Dibromo-9,10-di (4) obtained in Example 1- (1) '-biphenyl) anthracene) 7.7g (0.01 mol), 3-Pyridine boronic acid 4.4g (0.04 mol), K ₂ CO ₃ 10.0g (0.07 mol), Pd (PPh ₃ ) ₄ 0.7 g (0.6 mmol), 18 ml of water, 36 ml of 1,4-dioxane (1,4-Dioxane) and 36 ml of THF (Tetrahydrofurane) were added thereto, and the reaction was maintained at 80 ^° C. After the reaction was completed, the mixture was cooled to room temperature and filtered while washing with CH ₂ Cl ₂ . The filtrate was separated and the organic layer was washed three times with water, and then concentrated under reduced pressure to separate the column. The separated solution was concentrated under reduced pressure, and then crystals were precipitated with methanol and filtered, and washed several times with methanol. The crystals were then dried under reduced pressure to give 2,7-di (3-pyridyl) -9,10-di (4'-biphenyl) anthracene (2,7-Di (3-pyridyl) -9,10-di (4 '-biphenyl) anthraxcene) 3.0g (yield 39.3%, HPLC 99.8%, melting point 342.7 ° C) was prepared.

¹ H NMR (300 MHz, CDCl ₃ ): σ 7.32-7.40 (dd, 2H), 7.41-7.51 (m, 2H), 7.52-7.61 (m, 4H), 7.61-7.73 (m, 6H), 7.79- 7.95 (m, 10H), 7.95-8.02 (d, 2H), 8.02-8.08 (d, 2H), 8.55-8.62 (dd, 2H), 8.85-8.92 (d, 2H)

Example 1- (3)

Of organic light emitting device  Produce

The light emitting area of the indium tin oxide (ITO) glass was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in the vacuum chamber, the base pressure is 1 × 10 ^-6 torr and the organic material is deposited on the ITO anode, the hole injection layer CuPC 200Å, the hole transport layer NPD (N, N'-Di (naphthylen- 1-yl) -N, N'-diphenylbenzidine) 400Å, ADN (9,10-Di- (2-naphtyl) -anthracene) + C545T (10- (2-Benzothiazolyl) -1,1,7,7 -tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-benzo [l] pyrano [6,7,8, ij] quinolizin-11-one) (5%) 200 μs, Example 1- The organic light emitting device was manufactured by (2). An organic light emitting device was manufactured by coating and forming an n-type organic semiconductor material, which is an electron transporting layer, in an order of 350 kV, an electron injecting layer 5F, and a cathode of Al 1000 kV.

Example 2

Example 2- (1)

2,7-di (3-quinolinyl) -9,10- Di (4'-biphenyl) anthracene [ 2,7- Di (3- quinolinyl ) -9,10-di (4'-biphenyl) anthracene ] Synthesis of

In a 500 ml round bottom flask, 2,7-dibromo-9,10-di (4'-biphenyl) anthracene (2,7-Dibromo-9,10-di (4 ') obtained in 1- (1) above. -biphenyl) anthracene) 8.5g (0.01 mol), 3-Quinoline boronic acid 6.0g (0.04 mol), K ₂ CO ₃ 27.5g (0.20 mol), Pd (PPh ₃ ) ₄ 0.6g (0.5 mmol), 85 ml of ethanol (Ethanol), 170 ml of toluene and 85 ml of THF (Tetrahydrofurane) were added thereto, and the reaction was maintained at 80 ^° C. After the reaction was completed, the mixture was cooled to room temperature and filtered while washing with CH ₂ Cl ₂ . The filtrate was separated and the organic layer was washed three times with water, and then concentrated under reduced pressure to separate the column. The separated solution was concentrated under reduced pressure, and then crystals were precipitated with methanol and filtered, and washed several times with methanol. The crystals were then dried under reduced pressure to give 2,7-di (3-quinolinyl) -9,10-di (4'-biphenyl) anthracene (2,7-Di (3-quinolinyl) -9,10-di (4 '-biphenyl) anthraxcene) 3.0g (yield 30.7%, HPLC 99.0%, melting point 350.0 ℃) was prepared.

¹ H NMR (300 MHz, CDCl ₃ ): sigma 7.41-7.51 (m, 2H), 7.52-7.62 (m, 6H), 7.66-7.76 (m, 6H), 7.78-7.98 (m, 12H), 8.00- 8.08 (d, 2H), 8.08-8.17 (d, 2H), 8.17-8.26 (d, 2H), 8.26-8.37 (d, 2H), 9.13-9.26 (d, 2H)

Example 2- (2)

Of organic light emitting device  Produce

The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr and the organic material is placed on the ITO CuPC (200kPa), NPD (400kPa), ADN + C545T (5%) (200kPa), the embodiment An organic light emitting diode was manufactured by forming an n-type organic semiconductor material (350kV), LiF (5kV), and Al (1000kV) in the order of 2- (1).

Example 3

Example 3- (1)

2,7-di (4- (2-quinolinyl) Phenyl ) -9,10-D (4'- Biphenyl )anthracene [ 2,7-Di (4- (2-quinolinyl) phenyl) -9,10-di (4'-biphenyl) anthracene ] Synthesis of

2,7-Dibromo-9,10-di (4'-biphenyl) anthracene (2,7-Dibromo-9,10-di (4) obtained in Example 1- (1) in a 1000 ml round bottom flask '-biphenyl) anthracene) 12.0 g (0.02 mol), 4- (2-quinolinyl) phenyl boronic acid 11.7 g (0.05 mol), K ₂ CO ₃ 25.9 g ( 0.19 mol), 0.9 g (0.8 mmol) of Pd (PPh ₃ ) ₄ , 150 ml of ethanol (Ethanol), 300 ml of toluene and 150 ml of THF (Tetrahydrofurane) were added thereto, and the reaction was maintained at 80 ^° C. After the reaction was completed, the mixture was cooled to room temperature and filtered while washing with CH ₂ Cl ₂ . The filtrate was separated and the organic layer was washed three times with water, and then concentrated under reduced pressure to separate the column. The separated solution was concentrated under reduced pressure, and then crystals were precipitated with methanol, filtered and washed several times with methanol. The crystals were then dried under reduced pressure to give 2,7-di (4- (2-quinolinyl) phenyl) -9,10-di (4'-biphenyl) anthracene (2,7-Di (4- (2-quinolinyl) phenyl) -9,10-di (4′-biphenyl) anthraxcene) 6.0 g (yield 43.5%, HPLC 99.2%, melting point 329.7 ° C.) were prepared.

¹ H NMR (300MHz, CDCl ₃ ): sigma 7.40-7.62 (m, 8H), 7.64-8.02 (m, 26H), 8.07-8.32 (m, 10H)

Example 3- (2)

Of organic light emitting device  Produce

The light emitting area of the ITO glass was patterned to have a size of 3 mm x 3 mm and then washed. After mounting the substrate in the vacuum chamber, the base pressure is 1 × 10 ^-6 torr and the organic material is placed on the ITO CuPC (200 kPa), NPD (400 kPa), ADN + C545T (5%) (200 kPa), the embodiment An organic light emitting diode was manufactured by forming an n-type organic semiconductor material (350kV), LiF (5kV), and Al (1000kV) in the order of 3- (1).

Comparative Example 1

1- (1) Of organic light emitting device  Produce

An organic light emitting diode was manufactured according to the same method as Example 1, 2, and 3 except that Alq ₃ was used as the electron transporting layer.

Comparative Example 2

2,6-di (3- Pyridyl ) -9,10- Diphenylanthracene To the electron transport layer  using Organic field Manufacture of light emitting device

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using 2,6-di (3-pyridyl) -9,10-diphenyl-anthracene as an electron transport layer instead of Alq ₃ .

Comparative Example 3

2,6-di (3-quinolinyl) -9,10- Diphenylanthracene To the electron transport layer  using Of organic light emitting device  Produce

An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using 2,6-di (3-quinolinyl) -9,10-diphenylanthracene as an electron transport layer instead of Alq ₃ .

Comparative Example 4

2,6-di (3-quinolinyl) -9,10- Di (4'-biphenyl) anthracene To the electron transport layer  using Of organic light emitting device  Produce

An organic light emitting display device was manufactured under the same condition as Comparative Example 1, except that 2,6-di (3-quinolinyl) -9,10-di (4'-biphenyl) phenylanthracene was used as the electron transporting layer instead of Alq ₃ . Prepared.

Test Example 1

Properties such as voltage, current, brightness, CIE, and the like of the organic light emitting diodes of Examples 1, 2, 3, and Comparative Examples 1 to 4 were measured and summarized in Table 1 below.

Voltage (V) Current (mA) Luminance (cd / m ² ) CIE (X) CIE (Y) Example 1 5.2 0.4 1470 0.35 0.61 Example 2 5.1 0.4 1340 0.35 0.61 Example 3 5.4 0.4 1490 0.34 0.60 Comparative Example 1 6.1 0.4 1232 0.35 0.60 Comparative Example 2 5.8 0.4 1150 0.35 0.62 Comparative Example 3 6.2 0.4 1280 0.35 0.60 Comparative Example 4 5.7 0.4 1230 0.34 0.61

Referring to the analysis results, it can be seen that the organic light emitting display device according to Examples 1 to 3 has a lower driving voltage than the organic light emitting display device of Comparative Examples 1 to 4. In particular, the organic electroluminescent devices of Comparative Examples 2, 3, and 4 using pyridine or quinoline-substituted anthracene derivatives as electron transporting layers require a driving voltage of 5.7 volts or more and a luminance of 1280 cd / m ² or less. . Accordingly, the n-type organic semiconductor compound of the present invention in which an aryl group or a heteroaryl group is substituted at positions 2 and 7 of anthracene is significantly lower in driving voltage and excellent light emission than an anthracene derivative in which an aryl group or a heteroaryl group is substituted at 2,6. It can be seen that it has an efficiency.

1 is a cross-sectional view of an organic light emitting display device according to an embodiment of the present invention.

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

10: substrate 20: anode

30: hole injection layer 40: hole transport layer

50: organic light emitting layer 60: electron transport layer

70: electron injection layer 80: cathode

Claims (6)

delete delete delete N-type organic semiconductor compound, characterized in that any one compound selected from the group consisting of compounds represented by the following formula.

Anode; Cathode; And a layer provided between the anode and the cathode, the layer including the organic semiconductor compound according to claim 4. The organic electroluminescent device according to claim 5, wherein the organic semiconductor compound-containing layer is an organic light emitting layer or an electron transporting layer.

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