KR20100001274A - Organic compound, and organic photoelectric device including the same - Google Patents

Abstract

PURPOSE: An organic compound used for organic photoelectric device is provided to improve lifetime and efficiency of organic photoelectric device, electrochemical and thermal stability. CONSTITUTION: An organic compound contains a compound of chemical formula 1. The organic photoelectric device comprises anode; cathode, and organic thin layer between the anode and cathode. The organic thin layer contains the organic compound of chemical formula 1. The organic thin layer comprises one layer selected from light emitting layer, hole transport layer, hole injection layer, electron transport layer, electron injection layer, and their complex.

Description

Organic compound, and organic optoelectronic device including the same {ORGANIC COMPOUND, AND ORGANIC PHOTOELECTRIC DEVICE INCLUDING THE SAME}

The present invention relates to an organic compound, and an organic photoelectric device including the same, and more particularly, an organic compound capable of improving the lifespan, efficiency, electrochemical stability, and thermal stability of the organic photoelectric device, and an organic photoelectric device including the same. It relates to an element.

An organic photoelectric device refers to a device that requires charge exchange between an electrode and an organic material using holes or electrons. The organic photoelectric device may be classified into two types according to the operation principle.

First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.

The second is an electronic device in which holes and electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

Examples of the organic photoelectric device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, an organic transistor, and the like, all of which are used to inject or transport holes, inject or transport materials, and emit light for driving the device. It needs a substance.

Hereinafter, the organic light emitting device will be described in detail. However, in the organic photoelectric device, a hole injection or transport material, an electron injection or transport material, or a light emitting material functions on a similar principle.

Organic light emitting diodes (OLEDs) are attracting attention as the demand for flat panel displays increases. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.

Such an organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material and has a structure in which a functional organic thin film layer is inserted between an anode and a cathode. The organic thin film layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. .

When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic thin film layer at the anode and electrons are formed at the cathode, and when the injected holes and electrons meet, the excitons form again. As light moves to the ground state, light with a specific wavelength is generated.

The luminescence of these organic materials was noticed by the discovery of anthracene using anthracene in the early 1960s, but it was not attracted much attention due to the high driving voltage, and it was CW Tang of Eastman Kodak in the late 1980s. Attention has been focused on enabling low-voltage driving devices.

Subsequently, while developing a polymer light emitting device using polyphenylene vinylene (PPV) in Cambridge in 1990, the field is largely divided into low molecular OLED and polymer OLED. In the case of low-molecular OLED, the device is manufactured in the form of thin film by vacuum deposition method, so it has good efficiency and long-life performance.In the case of high-molecular OLED, the initial investment cost is small and large area is used by inkjet or spin coating method. Painter has an advantage.

Both low molecular weight OLEDs and high molecular weight OLEDs are attracting attention as next-generation displays because they have advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range. In particular, compared to the conventional LCD, the self-luminous type has good cyanity even in dark places or outside light, and the thickness and weight can be reduced to one third of the LCD level without the need for a backlight. In addition, the response speed is 1000 times faster than LCD in microseconds, so it is possible to realize perfect video without afterimage, and it is expected to be spotlighted as an optimal display for the recent multimedia era.

Based on these advantages, OLED has undergone rapid technological development with efficiency of 80 times and lifespan over 100 times since its first development in the late 1980s. Recently, 40-inch OLED panel is announced, and the size of OLED is rapidly growing.

In order to increase the size of the OLED, it is necessary to increase the luminous efficiency and improve the life of the device. Currently, the light emitting layer of the organic light emitting device generally uses a fluorescent or phosphorescent organic compound thin film. However, in case of using a single fluorescent emitting layer, quenching effect due to intermolecular interaction at high concentration, deterioration of color purity due to wide emission band, decrease of efficiency due to unbalance of electron and hole coupling, and driving voltage increase Has a problem.

The light emitting layer using the phosphorescent organic compound is composed of a host material and a dopant material that emits energy from the light, and dopant materials have been reported using various materials using iridium metal compounds at Princeton University and the University of Southern California. Also, 4,4'-N, N'-dicarbazole-biphenyl (4,4'-N, N'-dicarbazole-biphenyl, CBP) is widely used as a host. However, the CBP has a problem in that the blue light emission efficiency is low and the lifespan is short because energy transfer to the blue dopant is not sufficient.

In addition, in order to increase the luminous efficiency, problems such as the adhesion of the interface between the layers and the increase of the process due to the use of the hole blocking layer and the electron transport layer when stacking several layers in addition to the light emitting layer have also acted as problems in the enlargement.

Therefore, efforts are being made to improve the efficiency and lifespan of organic electroluminescent devices by improving the device structure as well as new materials that can compensate for this.

The present invention to solve the above problems, to provide an organic compound that can improve the lifetime, efficiency, electrochemical stability, and thermal stability of the organic photoelectric device.

Another object of the present invention is to provide an organic photoelectric device including the organic compound.

The technical problems to be achieved by the present invention are not limited to the technical problems mentioned above, and other technical problems not mentioned will be clearly understood by the average person from the following description.

In order to achieve the above object, according to one embodiment of the present invention, there is provided an organic compound comprising a compound represented by the following formula (1).

[Formula 1]

(In Formula 1,

Ar ₁ and Ar ₃ are each independently selected from the group consisting of a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, and a substituted or unsubstituted hetero ring group having 2 to 30 carbon atoms,

Ar ₂ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, and substituted Or any one selected from the group consisting of unsubstituted heteroarylamine groups having 2 to 30 carbon atoms,

R ₁ to R ₃ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number 3 to Selected from the group consisting of 30 cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms Which one is

N ₁ to n ₃ are each independently an integer of 0 to 4)

According to another embodiment of the present invention, an organic thin film layer includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, and the organic thin film layer includes the organic compound.

The organic thin film layer preferably includes a light emitting layer, and any one layer selected from the group consisting of a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, and a combination thereof.

Other specific details of embodiments of the present invention are included in the following detailed description.

The organic compound of the present invention is a novel compound, which can be used as a material for an organic photoelectric device, and can improve lifespan, efficiency, electrochemical stability, and thermal stability of the organic photoelectric device.

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.

According to one embodiment of the present invention, an organic compound including the compound represented by Chemical Formula 1 is provided.

[Formula 1]

(In Formula 1,

Ar ₁ and Ar ₃ are each independently selected from the group consisting of a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, and a substituted or unsubstituted hetero ring group having 2 to 30 carbon atoms,

Ar ₂ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, and substituted Or any one selected from the group consisting of unsubstituted heteroarylamine groups having 2 to 30 carbon atoms,

R ₁ to R ₃ are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number 3 to Selected from the group consisting of 30 cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms Which one is

N ₁ to n ₃ are each independently an integer of 0 to 4)

As used herein, "substituted" means a halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted unless otherwise specified herein. A substituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl Mean substituted by any one of the substituents selected from the group consisting of groups.

In addition, in the present specification, "hetero" means, unless specified herein, that one to three carbon atoms in the ring is substituted with any one hetero atom selected from the group consisting of N, O, S, and P. .

In Formula 1, Ar ₁ and Ar ₃ are It is selected from the group consisting of a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

Preferred examples of the aromatic ring group include substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted stilbene, substituted or unsubstituted phenanthrene, substituted or unsubstituted It may be selected from the group consisting of pyrene, and substituted or unsubstituted perylene, but is not limited thereto.

The heterocyclic group means a 5- or 6-membered ring group, and preferred examples thereof include substituted or unsubstituted furan, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted taazole , Substituted or unsubstituted oxazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted imidazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrimidine, substituted Or unsubstituted pyrazine, substituted or unsubstituted triazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted cynoline, substituted or unsubstituted quinoxaline, substituted or Unsubstituted quinazoline, substituted or unsubstituted phthalazine, substituted or unsubstituted thiadiazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted purine , Substituted or unsubstituted benzoxazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline, substituted or unsubstituted benzoquinoline, and substituted Or an unsubstituted phenanthridine, but is not limited thereto.

Ar ₂ in Formula 1 is Hydrogen atom; Substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted stilbene group, substituted or unsubstituted phenanthrene group, substituted or unsubstituted pyrene group, and substituted Or any aryl group selected from the group consisting of unsubstituted perylene groups; Substituted or unsubstituted furan group, substituted or unsubstituted thiophene group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted oxazole group, substituted or unsubstituted oxadiazole group, substituted or unsubstituted taa Sol group, substituted or unsubstituted imidazole group, substituted or unsubstituted thiadiazole group, substituted or unsubstituted benzoxazole group, substituted or unsubstituted benzthiazole group, substituted or unsubstituted benzimidazole group, substituted or Unsubstituted pyridine group, substituted or unsubstituted pyrazine group, substituted or unsubstituted pyrimidine group, substituted or unsubstituted pyridazine group, substituted or unsubstituted triazine group, substituted or unsubstituted quinoline group, substituted or Unsubstituted isoquinoline group, substituted or unsubstituted quinoxaline group, substituted or unsubstituted quinazolin group, substituted or unsubstituted phthalazine group, substituted or unsubstituted cynoline group, substituted or unsubstituted purine , A substituted or unsubstituted acridine group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted benzoquinoline group, and a substituted or unsubstituted phenanthtridine group is any one heteroaryl group selected from Preferred, but not limited to.

The organic compound represented by Formula 1 is benzoxazole; And a combination of two pyridine groups and Ar ₃ serving as a linkage thereof (hereinafter, referred to as core portion). In addition, the organic compound includes a variety of substituents, and Ar ₁ to the link role of the core portion and Ar ₂ of Ar _2.

The organic compound represented by Chemical Formula 1 may be an aryl group such as phenyl as a substituent of Ar ₂ ; Hexagonal heteroaryl groups into which nitrogen atoms were introduced, such as a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an iso quinoline group, a quinoxaline group, a quinazoline group, a phthalazine group, etc .; Or pentagonal heteroaryl groups such as furan group, thiophene group, oxazole group, oxadiazole group, thiazole group, imidazole group, thiadiazole group, benzoxazole group, benzthiazole group, benzimidazole group and the like, Structural coordination with the core portion may provide various characteristics required for the organic photoelectric device.

In addition, by introducing a heteroaryl group as the substituent of Ar _{2 It} is possible to synthesize a compound having a variety of energy bandgap based on the core portion. Therefore, according to the properties of each heteroaryl group, various conditions can be sought in order to satisfy the conditions required in each layer of the light emitting layer, the hole transport layer, the hole injection layer, the electron transport layer, or the electron injection layer.

In addition, an organic photoelectric device having a low driving voltage and high efficiency may be realized by controlling an appropriate energy level based on a substituent of Ar ₁ or Ar ₂ based on the core part.

In Formula 1, Ar ₁ to Ar ₃ are each independently any one selected from the group consisting of compounds represented by Formulas 2 to 12 below.

(In the above formula 2 to 12,

Z ₁ to Z ₆₅ , and Z ₆₇ to Z ₉₃ are each independently selected from the group consisting of CR ₁ and N,

X ₁ and X ₂ are each independently any one selected from the group consisting of NR ₂ , S, and O;

R ₁ and R ₂ are each independently a hydrogen atom, a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number 3 to Selected from the group consisting of 30 cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms do)

In particular, preferred examples of Ar ₁ to Ar ₃ in Formula 1 are the same as in Formula 13 to 58, but are not limited thereto. Wherein Formula 13 to 58 are linked in the formula (1) is any one of the carbon atoms in each ring.

[Formula 13] [Formula 14] [Formula 15] [Formula 16] [Formula 17]

[Formula 18] [Formula 19] [Formula 205] [Formula 21] [Formula 22]

[Formula 23] [Formula 24] [Formula 25] [Formula 26] [Formula 27]

[Formula 28] [Formula 29] [Formula 30] [Formula 31] [Formula 32]

[Formula 33] [Formula 34] [Formula 35] [Formula 36] [Formula 37]

[Formula 38] [Formula 39] [Formula 40] [Formula 41] [Formula 42]

[Formula 43] [Formula 44] [Formula 45] [Formula 46] [Formula 47]

[Formula 48] [Formula 49] [Formula 50] [Formula 51] [Formula 52]

[Formula 53] [Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Formula 58]

The organic compound represented by Chemical Formula 1 is more preferably represented by the following Chemical Formulas 59 to 112. However, the organic compound according to the embodiment of the present invention is not limited thereto.

According to another embodiment of the present invention, there is provided an organic photoelectric device including an organic thin film layer including the organic compound between an anode and a cathode. The organic photoelectric device is preferably an organic light emitting device.

The organic thin film layer is preferably selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, and combinations thereof, and more preferably an electron transport layer.

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art may easily implement the present invention. As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention.

1 to 5 are cross-sectional views illustrating various embodiments of an organic photoelectric device that may be manufactured using an organic compound according to an embodiment of the present invention.

1 to 5, the organic photoelectric device 100, 200, 300, 400, and 500 according to an embodiment of the present invention has one or more layers disposed between the anode 120 and the cathode 110. The organic thin film layer 105 may include a structure including an organic thin film layer 105, an indium tin oxide (ITO) transparent electrode for the anode 120, and a metal electrode such as aluminum for the cathode 110.

As the material of the anode 120, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material may include vanadium, chromium, copper, zinc, gold, or an alloy thereof, and a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO). And combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) Thiophene] (PEDT), polypyrrole, conductive polymers such as polyaniline, and the like, but are not limited thereto.

It is preferable that the material of the cathode 110 is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, and alloys thereof, and include LiF / Al or LiO ₂ / Al and The same multilayered structure materials may be used, but are not limited thereto.

First, referring to FIG. 1, FIG. 1 illustrates an organic photoelectric device 100 in which only the emission layer 130 exists as the organic thin film layer 105.

Referring to FIG. 2, FIG. 2 illustrates a two-layered organic photoelectric device 200 in which an emission layer 230 including an electron transport layer (not shown) and a hole transport layer 140 exist as an organic thin film layer 105. The hole transport layer 140 is a separate layer made of a film having excellent adhesion to a transparent electrode such as ITO or hole transport.

Referring to FIG. 3, in FIG. 3, a three-layer organic photoelectric device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, the emission layer 130 may be formed. It has become an independent form, and has shown the form which laminated | stacked the film | membrane excellent in the electron transport property and the hole transport property by another layer.

Referring to FIG. 4, in FIG. 4, a four-layered organic photoelectric device 400 having an electron injection layer 160, an emission layer 130, a hole transport layer 140, and a hole injection layer 170 as an organic thin film layer 105. As an example, the hole injection layer 170 is added in consideration of the bonding property with ITO used as the anode.

Referring to FIG. 5, in FIG. 5, the organic thin film layer 105 may have different functions such as an electron injection layer 160, an electron transport layer 150, an emission layer 130, a hole transport layer 140, and a hole injection layer 170. The five-layer organic photoelectric device 500 having five layers is present, and the organic photoelectric device 500 has an characteristic of effectively lowering the voltage by forming the electron injection layer 160 separately.

In order to form the organic thin film layer 105 having one to five layers described above, dry film forming methods such as evaporation, sputtering, plasma plating, and ion plating, spin coating, Processes such as dipping, wet film-forming methods such as flow coating, and the like can be used.

In the organic photoelectric device according to the embodiment of the present invention, any one of the light emitting layer, the electron transporting layer, the electron injection layer, the hole transporting layer, the hole injection layer, the hole blocking layer, and a combination thereof may include the organic compound. desirable.

The following presents specific embodiments of the present invention. However, the embodiments described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.

(Production of Organic Compound)

( Example  1: Synthesis of Organic Compound Represented by Chemical Formula 85)

[Formula 85]

2- (3,5-dibromophenyl) benzoxazole (2.96 g, 0.00836 mole) and 3,5-dipyridylphenylboronic acid (5.08 g, 0.0184 mole) were dissolved in tetrahydrofuran (80 mL) to give first A mixed solution was prepared and tetrakistriphenylphosphine (0.966 g, 0.000836 mol) was added dropwise as a catalyst and stirred at room temperature for 10 minutes. An aqueous solution of potassium carbonate (6.94 g, 0.0502 mol) dissolved in water (20 mL) was added to the first mixed solution to prepare a second mixed solution, stirred at 80 ^° C. for 12 hours, and left through a celite pad. Any catalyst was removed. In the resultant mixture, only the organic layer was separated, dried, concentrated, and finally, the obtained residue was subjected to silica gel chromatography and reduced pressure drying to obtain an organic compound represented by Chemical Formula 85 (4.11 g, 75% yield). ¹ H NMR measurement results of the compound are shown in FIG.

( Example  2: synthesis of an organic compound represented by formula 105)

[Formula 105]

Dissolve 2- (2,5-dibromophenyl) benzoxazole (4.44 g, 0.0125 mol) and 3,5-dipyridylphenylboronic acid (7.62 g, 0.0276 mol) in tetrahydrofuran (120 mL) A mixed solution was prepared and tetrakistriphenylphosphine (1.45 g, 0.00125 mol) was added dropwise as a catalyst and stirred at room temperature for 10 minutes. An aqueous solution of potassium carbonate (10.4 g, 0.0753 mol) dissolved in water (30 mL) was added to the first mixed solution to prepare a second mixed solution, stirred at 80 ^° C. for 12 hours, and left through a celite pad. Any catalyst was removed. In the resultant mixture, only the organic layer was separated, dried, concentrated, and finally, the obtained residue was subjected to silica gel chromatography and reduced pressure drying to obtain an organic compound represented by Chemical Formula 105 (5.76 g, 70% yield). ¹ H NMR measurement results of the compound are shown in FIG.

( Example  3: synthesis of an organic compound represented by formula 106)

[Formula 106]

Dissolve 2- (2-bromo-3-pyridyl) benzoxazole (2.50 g, 0.00909 mol) and 3,5-dipyridylphenylboronic acid (3.01 g, 0.0109 mol) in tetrahydrofuran (60 mL) 1 A mixed solution was prepared, and tetrakistriphenylphosphine (0.525 g, 0.000455 mol) was added dropwise as a catalyst, followed by stirring at room temperature for 10 minutes. An aqueous solution of potassium carbonate (3.77 g, 0.0273 mol) dissolved in water (15 mL) was added to the first mixed solution to prepare a second mixed solution, stirred at 80 ^° C. for 12 hours, and left through a pad of celite. Any catalyst was removed. In the resultant mixture, only the organic layer was separated, dried, concentrated, and finally, the obtained residue was subjected to silica gel chromatography and reduced pressure drying to obtain an organic compound represented by Chemical Formula 106 (2.79 g, 72% yield). ¹ H NMR measurement results of the compound are shown in FIG. 8.

(abandonment Photoelectric  Manufacture of devices)

( Example  4)

Corning's 15Ω / cm ² (1200Å) ITO glass substrates were cut to 50 mm x 50 mm x 0.7 mm and ultrasonically cleaned for 5 minutes in isopropyl alcohol and pure water, followed by UV and ozone cleaning for 30 minutes. .

N, N'-di (4- (N, N'-diphenyl-amine) phenyl) -N, N'-diphenylbenzidine (DNTPD, 40 nm), N, N'-di (1 -Naphthyl) -N, N'-diphenylbenzidine (NPB, 10 nm), EB-46 (e-Ray, 40 nm) and the organic compound (10 nm) prepared in Example 2 were sequentially subjected to thermal vacuum deposition An injection layer, a hole transport layer, a light emitting layer, and an electron transport layer were formed in this order.

LiF was vacuum deposited to a thickness of 0.5 nm as an electron injection layer on the electron transport layer, and Al was vacuum deposited to a thickness of 100 nm to form a LiF / Al electrode. The structure of the manufactured organic photoelectric device is as shown in FIG. 3.

( Example  5)

DNTPD (40 nm), NPB (10 nm), EB-46 (40 nm) and the organic compound (10 nm) prepared in Example 1 were sequentially vacuum-deposited on the glass substrate prepared as in Example 4 to inject a hole. , The major transport layer, the light emitting layer, and the electron transport layer were formed in this order.

LiF was vacuum deposited to a thickness of 0.5 nm as an electron injection layer on the electron transport layer, and Al was vacuum deposited to a thickness of 100 nm to form a LiF / Al electrode.

( Comparative example  One)

Thermal vacuum deposition of DNTPD (40 nm), NPB (10 nm), EB-46 (40 nm) and Alq ₃ which is an organic compound represented by the following Chemical Formula 113 (10 nm) sequentially on the glass substrate prepared as in Example 4 The hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer were formed in this order.

[Formula 113]

LiF was vacuum deposited to a thickness of 0.5 nm as an electron injection layer on the electron transport layer, and Al was vacuum deposited to a thickness of 100 nm to form a LiF / Al electrode.

(abandonment Photoelectric  Device performance measurement)

For each organic photoelectric device manufactured in Example 5 and Comparative Example 1, the luminous efficiency according to voltage was measured. The specific measuring method is as follows.

1) Measurement of change in current density according to voltage change

For each organic photoelectric device manufactured in Example 5 and Comparative Example 1, while measuring the voltage from 0V to 14V while using a current-voltmeter (Keithley 2400) to measure the current value flowing through the unit device, The current density was measured by dividing the current value by the area.

2) Measurement of luminance change according to voltage change

For each organic photoelectric device manufactured in Example 5 and Comparative Example 1, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 14V.

3) current efficiency, and power efficiency measurement

The current efficiency and the power efficiency were calculated using the luminance values, the current densities, and the voltages measured from the above 1) and 2), and the results are summarized in Table 1 below.

TABLE 1

Threshold Voltage (V) Luminance 1000 cd / m ² Color coordinates (CIE)  Drive voltage (V) Current efficiency (cd / A) Power Efficiency (lm / W) x y Example 5 3.00 6.00 6.04 3.16 0.15 0.17 Comparative Example 1 3.60 7.60 5.18 2.14 0.15 0.15

Referring to Table 1, the organic photoelectric device of Example 5 exhibits better performance in all aspects such as threshold voltage, driving voltage and current efficiency, and power efficiency than when Alq ₃ is used as the electron transport layer as in Comparative Example 1. It can be seen.

The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

1 to 5 are cross-sectional views illustrating various embodiments of an organic photoelectric device that may be manufactured using an organic compound according to an embodiment of the present invention.

6 to 8 show the ¹ H NMR measurement results of the compound prepared according to Examples 1 to 3.

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

100 organic photoelectric device 110 cathode

120: anode 105: organic thin film layer

130: light emitting layer 140: hole transport layer

150: electron transport layer 160: electron injection layer

170: hole injection layer

Claims (9)

An organic compound comprising a compound represented by the following formula (1). [Formula 1]

(In Formula 1, Ar ₁ and Ar ₃ are each independently selected from the group consisting of a substituted or unsubstituted aromatic ring group having 6 to 30 carbon atoms, and a substituted or unsubstituted hetero ring group having 2 to 30 carbon atoms, Ar ₂ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, and substituted Or any one selected from the group consisting of unsubstituted heteroarylamine groups having 2 to 30 carbon atoms, R ₁ to R ₃ are each independently a hydrogen atom, a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C1-20 alkyl group, a substituted or unsubstituted C3-30 Selected from the group consisting of a cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms Which one, N ₁ to n ₃ are each independently an integer of 0 to 4, The substituted Iran hydrogen atom is halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted A substituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms substituted with any one of substituents selected from the group will be) The method of claim 1, In Formula 1, Ar ₁ and Ar ₃ are Each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted stilbene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, And a substituted or unsubstituted perylene (any one aromatic ring group selected from the group consisting of, The substituted Iran hydrogen atom is halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted A substituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms substituted with any one of substituents selected from the group Organic compound. The method of claim 1, Ar ₁ and Ar ₃ in Formula 1 are each independently substituted or unsubstituted furan, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted tazol, substituted or unsubstituted Oxazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted imidazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, Substituted or unsubstituted triazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted quinazoline, substituted or unsubstituted phthalazine, substituted or unsubstituted Thiadiazole, substituted or unsubstituted cinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted benzimidazole, substituted or unsubstituted purine, substituted or unsubstituted benzox Sol, substituted or unsubstituted benzothiazole, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline, substituted or unsubstituted benzoquinoline, and substituted or unsubstituted phenanthridine ( phenanthridine) is any one heterocyclic group selected from the group consisting of The substituted Iran hydrogen atom is halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted A substituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms substituted with any one of substituents selected from the group Organic compound. The method of claim 1, Ar ₂ in Formula 1 is Substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted stilbene group, substituted or unsubstituted phenanthrene group, substituted or unsubstituted pyrene group, and substituted Or an aryl group selected from the group consisting of unsubstituted perylene groups, The substituted Iran hydrogen atom is halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted A substituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms substituted with any one of substituents selected from the group Organic compound. The method of claim 1, Ar ₂ in Formula 1 is a substituted or unsubstituted furan group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted oxazole group, a substituted or unsubstituted oxadiazole group , Substituted or unsubstituted thiazole group, substituted or unsubstituted imidazole group, substituted or unsubstituted thiadiazole group, substituted or unsubstituted benzoxazole group, substituted or unsubstituted benzthiazole group, substituted or unsubstituted Benzimidazole groups, substituted or unsubstituted pyridine groups, substituted or unsubstituted pyrazine groups, substituted or unsubstituted pyrimidine groups, substituted or unsubstituted pyridazine groups, substituted or unsubstituted triazine groups, substituted or unsubstituted A substituted quinoline group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted phthalazine group, a substituted or unsubstituted cynoline group, Selected from the group consisting of a cyclic or unsubstituted purine group, a substituted or unsubstituted acridine group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted benzoquinoline group, and a substituted or unsubstituted phenanthtridine group Which is one heteroaryl group, The substituted Iran hydrogen atom is halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted A substituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms substituted with any one selected from the group consisting of Organic compound. The method of claim 1, Wherein Ar ₁ to Ar ₃ are each independently any one selected from the group consisting of compounds represented by Formulas 2 to 12.

(In the above formula 2 to 12, Z ₁ to Z ₆₅ , and Z ₆₇ to Z ₉₃ are each independently selected from the group consisting of CR ₁ and N, X ₁ and X ₂ are each independently any one selected from the group consisting of NR ₂ , S, and O; R ₁ and R ₂ are each independently a hydrogen atom, a halogen, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number 3 to Selected from the group consisting of 30 cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms Become, The substituted Iran hydrogen atom is halogen, cyano group, hydroxyl group, amino group, nitro group, carboxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted A substituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms substituted with any one of substituents selected from the group will be) The method of claim 1, The compound represented by Chemical Formula 1 is any one selected from the group consisting of compounds represented by the following Chemical Formulas 59 to 112.

anode; cathode; And an organic thin film layer disposed between the anode and the cathode, The organic thin film layer includes an organic compound according to any one of claims 1 to 8. The method of claim 8, The organic thin film layer, Light emitting layer; And An organic photoelectric device comprising any one selected from the group consisting of a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, and a combination thereof.

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