KR20180049866A - Iridium complex compounds and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to an iridium complex compound and an organic electroluminescent device using the same. More specifically, the present invention relates to an iridium complex compound securing low driving voltage as well as excellent color purity, luminescent properties, luminescent efficiency, and lifespan properties when used as a dopant in light-emitting layers of organic electroluminescent devices by producing the novel compound which is a complex having iridium as central metal. The present invention further relates to a method for efficiently synthesizing the same, and an organic electroluminescent device using the same.

Description

FIELD OF THE INVENTION [0001] The present invention relates to an iridium complex compound, and an organic electroluminescent device using the iridium complex compound.

The present invention relates to an iridium complex and an organic electroluminescent device using the iridium complex. More particularly, the present invention relates to a novel compound which is a complex having iridium as a central metal, , A luminescent efficiency and a lifetime, as well as a method for efficiently synthesizing an iridium complex, and an organic electroluminescent device using the iridium complex

Organic light-emitting diodes (OLEDs) are displays using organic materials that emit themselves. More specifically, when an electric field is applied to an organic electroluminescent device, electrons and holes are transmitted from the cathode and the anode to each other and are coupled in the organic material, and the generated energy is emitted as light. . Organic electroluminescent devices have lower power consumption than LCDs, have a better viewing angle and have a significantly improved response speed, and are able to process high-quality images.

The phenomenon in which an organic electroluminescent device emits light can be roughly classified into fluorescence and phosphorescence. Fluorescence is a phenomenon in which organic molecules emit light when they fall from a singlet excited state to a ground state. Phosphorescence is a phenomenon in which organic molecules emit light when they fall from a triplet excited state to a ground state.

The organic compound doped in the organic electroluminescent device including the light emitting layer forms a molecule through a covalent bond of electrons between carbon and another carbon, or between carbon and another atom. In this molecular electron orbit, two pairs of electron orbits in the atomic state participate to form a bonding orbit (Bonding Molecular Orbital) and an antibonding molecular orbital respectively. At this time, the band formed by many coupling orbits is called a valence band, and a band formed by many semi-coupling orbits is called a conduction band. The highest energy level of a valence band is called a HOMO (Lowest Unoccupied Molecular Orbital), and the energy difference between the HOMO energy and the LUMO is called a band gap (Band Gap).

Electrons and holes injected into the LUMO and HOMO of the organic light emitting layer constituting the organic electroluminescent device are recombined to form an exciton. The electric energy of the exciton is converted into light energy, Thereby realizing light of a color corresponding to the energy bandgap. In this process, a singlet exciton with a total spin of 0 and a triplet exciton with a spin quantum sum of 1 are produced at a ratio of about 1: 3. At this time, the selection rule for the electronic dipole moment transition, that is, the transition process in which the spin quantum number is changed when transitioning from the excited state to the ground state becomes a very difficult process. Since the bottom state of the organic molecules is a singlet state, single excitons emit light and can efficiently emit fluorescence by making a transition to a bottom state. However, since triplet excitons need to change the spin quantum number, Can not. Therefore, in general, the maximum internal quantum efficiency is limited to 25% in the case of an organic electroluminescent device in which a fluorescent dye is used as a light emitting layer or doped in a light emitting layer.

On the other hand, if the spin-orbital coupling can be greatly increased, the mixing of singlet and triplet states is increased and the efficiency of inter-system crossing between single-and triplet states is greatly increased In addition, triplet excitons can undergo phosphorescence under transient conditions. As a result, if the triplet exciton can be utilized to emit light, the internal quantum efficiency of the organic electroluminescent device can be theoretically improved to 100%.

The organic electroluminescent device for phosphorescence capable of dramatically improving the luminous efficiency of the organic electroluminescent device is disclosed in S. R. Prof. Forrest and M.E. In particular, the spin-orbit coupling is proportional to the fourth power of the atomic number, so it is a heavy atom complex such as platinum (Pt), iridium (Ir), europium (Eu), terbium It is known that the phosphorescence efficiency is high. In the case of the platinum complex, the lowest triplet exciton is a ligand-centered exciton (LC exciton) centered at the ligand, but the iridium complex has the lowest energy triplet exciton in the charge transfer state between the central metal and the ligand charge transfer, MLCT). Therefore, the iridium complex forms a larger spin-orbital bond as compared with the platinum complex, and exhibits a higher phosphorescence efficiency with a shorter triplet exciton lifetime.

In this regard, C. Adachi et al. Proposed the use of 3-phenyl-4- (1'-naphthyl) bis (2-phenylpyridine) iridium (acetylacetonate) -5-phenyl-1,2,4-triazole (TAZ) to obtain a maximum luminous efficiency of 60 lm / W and a maximum internal quantum efficiency of 87%. In addition, US Universal Display Corp. (UDC) has announced that it has achieved high luminous efficiency of 82 lm / W by doping such a green phosphorescent pigment into a light emitting layer and using a hole injecting material developed by domestic LG Chemical.

Organic electroluminescent devices for phosphorescence exhibiting blue, green and red colors have been developed, but organic electroluminescent devices for phosphorescence of three primary colors, which are excellent in luminous efficiency, color coordinates and lifetime characteristics, have not been developed sufficiently. For example, recently, it has been reported that Ir (btp) 2 (acac), which is a phosphorescent material that emits blue light, and Ir (btp) 2 (acac), which emits red luminescent color, (Iridium () bis (2- (2'-benzothienyl) pyridinato-N, C2) (acetylacetonate) has been developed but has not yet reached satisfactory levels of color purity, efficiency and solubility, to be.

In particular, iridium complexes vary greatly in the degree of hue (e.g., blue) to be realized even with slight structural differences. A conventional iridium complex phosphorescent dopant having a substituent introduced into only one side of the mother nucleus has a desired level of dark color (e.g., ) Could not be implemented.

DISCLOSURE Technical Problem Accordingly, the present invention has been made keeping in mind the above problems occurring in the prior art, and it is an object of the present invention to provide an organic electroluminescent device having a novel structure capable of realizing a higher luminous efficiency, And an iridium complex compound.

In order to achieve the above technical object, the present invention provides an iridium complex having a specific structure in which iridium (III) is a center metal complex, and the same substituent is introduced to both of the imidazole moieties.

Also, the iridium complex is used as an organic material layer of an organic electroluminescent device.

Specifically, the iridium complex is used as an emission layer material of an organic electroluminescent device.

More specifically, the iridium complex is used as a dopant material of an organic electroluminescent light emitting layer.

According to another aspect of the present invention, there is provided a process for efficiently and economically synthesizing the iridium complex.

According to still another aspect of the present invention, there is provided an organic electroluminescent device including a first electrode, a second electrode, and at least one organic material layer disposed between the electrodes, wherein the at least one organic material layer includes a light emitting layer, An organic electroluminescent device comprising the iridium complex according to the present invention.

Specifically, the organic electroluminescent device is characterized in that the host material is doped with the iridium complex.

In addition, the at least one organic material layer may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

When the iridium complex according to the present invention is used as a light emitting layer material (in particular, a dopant) of an organic electroluminescent device, excellent color purity can be realized in addition to high luminous efficiency, luminance characteristics, lifetime characteristics and low driving voltage of the device.

Specifically, the iridium complex according to the present invention is a phosphorescent dopant that facilitates energy transfer. When an organic thin film layer containing a conjugated polymer having fluorescent electroluminescence characteristics and a novel iridium complex phosphorescent dopant of the present invention is provided, The red, blue, and green luminescence can be efficiently displayed.

Also, according to the production method of the present invention, the iridium complex can be efficiently and economically synthesized through an easy process.

1 is a schematic view illustrating a single layer structure of an organic electroluminescent device according to an embodiment of the present invention.
FIG. 2 is a schematic view illustrating a multiple layer structure of an organic electroluminescent device according to another embodiment of the present invention. Referring to FIG.
3 is a graph showing UV (Ultraviolet) spectrum of Compound 1 prepared according to the present invention.
4 is a graph showing UV (Ultraviolet) spectrum of Compound 7 prepared according to the present invention.
5 is a graph showing PL (Photoluminescence) spectrum of Compound 1 prepared according to the present invention.

Hereinafter, the present invention will be described in detail.

Iridium complex

The iridium complex according to the present invention is represented by the following general formula (I).

(I)

In the formula (I)

Ar ₁ is a hydrogen atom substituted or unsubstituted with at least one of methyl, trifluoromethyl, phenyl and thiophene, Ar ₂ is substituted with at least one of methyl, ethyl, trifluoromethyl, phenyl, cyano and thiophene Or an unsubstituted hydrogen atom, each Ar ₁ may form a mutual condensation ring.

Ar ₃ is a hydrogen atom, methoxy or fluorine.

Specifically, the iridium complex according to the present invention is selected from the group of compounds represented by the following structural formulas, and they can be suitably used as an organic material layer material of an organic electroluminescent device.

Here, the organic material layer of the organic electroluminescent device may include at least one of an electroluminescence layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, And an electron injection layer (electron injection layer).

In particular, the iridium complex according to the present invention exhibits excellent luminescence characteristics and is used as a dopant of a light emitting layer material of an organic electroluminescent device, particularly a dopant material of an organic electroluminescent device, to efficiently form red, blue (in particular, deep blue) And green light emission can be realized.

Here, the iridium complex (dopant) according to the present invention is preferably doped in an amount of about 0.1 to 50% by weight with respect to the light emitting layer. If the content of the dopant is less than 0.1 wt%, it may be difficult to expect the effect of doping. If the content of the dopant is more than 50 wt%, the composition of the host and the dopant may be reversed.

Meanwhile, the iridium complex according to the present invention can be used for a flat panel display, a planar illuminant, an illuminant for a surface-emitting OLED for illumination, a flexible illuminant, a copier, a printer, an LCD backlight, a meter light source, And organic electronic devices such as an organic solar cell (OSC), an electronic paper (e-paper), an organic photoconductor (OPC), and an organic transistor (OTFT) may act on a principle similar to that applied to an organic light emitting device.

The iridium complex according to the present invention comprises the steps of: (a) reacting a compound represented by the following formula (1) and a compound represented by the following formula (2) together with phosphorus pentasulfide to obtain a compound represented by the following formula (3); (b) reacting the obtained compound represented by the following formula (3) with benzaldehyde to obtain a compound represented by the following formula (4); (c) adding potassium permanganate and acetonitrile to the compound represented by the following formula (4) to obtain a compound represented by the following formula (5); And (d) adding iridium chloride and 2-ethoxyethanol to the obtained compound represented by the following general formula (5) and reacting them to obtain a compound represented by the following general formula (I).

[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

(I)

In the above formulas,

Ar ₁ is a hydrogen atom substituted or unsubstituted with at least one of methyl, trifluoromethyl, phenyl and thiophene, Ar ₂ is substituted with at least one of methyl, ethyl, trifluoromethyl, phenyl, cyano and thiophene Or an unsubstituted hydrogen atom, each Ar ₁ may form a mutual condensation ring.

Ar ₃ is a hydrogen atom, methoxy or fluorine.

FIGS. 3, 4 and 5 show UV (Ultraviolet) / PL (Photoluminescence) spectra of the compounds 1 and 7 prepared according to the present invention. The UV / PL spectrum is a graph measuring the emission wavelength of each compound in order to characterize the OLED, and measuring the wavelength at which light is most emitted by irradiating light of a wavelength absorbed through UV. The UV / PL spectrum can be obtained through a method known in the art. In the present invention, a solid film prepared by coating a solution containing Compound 1 in Quartz is irradiated with excitation light to obtain a spectrum.

As a result, as shown in FIG. 5, since the iridium complex according to the present invention has a maximum emission peak at about 460 nm to 465 nm, it is expected that the efficiency of light emission is excellent.

Organic electroluminescent device

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising an iridium complex as described above as an organic material layer.

The organic layer of the organic electroluminescent device of the present invention may have a single layer structure of one layer or a multilayer structure of two or more layers including a light emitting layer. Here, in the case where the organic material layer has a multilayer structure, it may be a structure in which a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like are stacked. That is, the organic electroluminescent device of the present invention may have the structure shown in FIG. 1 (single layer structure) and FIG. 2 (multiple layer structure), but it is not limited thereto.

Specifically, the present invention comprises a first electrode (02), a second electrode (03) formed on a substrate (01), and at least one organic layer disposed between the electrodes and at least one layer of the organic layer An organic electroluminescent device comprising an iridium complex according to the present invention is provided.

More specifically, the present invention is an organic electroluminescent device comprising a first electrode (02), a second electrode (03) formed on a substrate (01) and one or more organic layers disposed between the electrodes The organic layer includes the light emitting layer 06 and the light emitting layer 06 includes the iridium complex according to the present invention. Here, the one or more organic layers may include at least one layer selected from the group consisting of a hole injection layer 04, a hole transport layer 05, a hole blocking layer (not shown), an electron transport layer 07 and an electron injection layer 08 As shown in FIG. For example, in the organic electroluminescent device of the present invention, the organic material layer includes a hole injecting layer 04, a hole transporting layer 05, a light emitting layer 06, a hole blocking layer (not shown), an electron transporting layer 07, 08, and one or two layers of a hole injection layer 04, a hole transport layer 05, a hole blocking layer (not shown), an electron transport layer 07 and an electron injection layer 08 are formed as needed Can be used in an omitted state.

The organic electroluminescent device of the present invention can be manufactured by a conventional method and materials for manufacturing an organic electroluminescent device, except that the above-described iridium complex is used to form one or more organic layers.

For example, the organic electroluminescent device according to the present invention may be formed by depositing a metal and a conductive material on the substrate 01 by using a known PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation A hole transporting layer 05, a light emitting layer 06, a hole blocking layer (not shown), and an electron transporting layer 07 (not shown) are formed on the anode 02 by depositing a metal oxide or an alloy thereof. And an electron injection layer 08, and then depositing a material usable as the cathode 03 on the organic layer. An organic electroluminescent device may also be manufactured by sequentially depositing a cathode 03 material, an organic material layer, and an anode 02 material on the substrate 01. Herein, the organic material layer may be formed by using a variety of polymer materials, but not by evaporation, but by using a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Can also be produced.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specifically, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), titanium oxide (TiO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, no.

As the negative electrode material, a material having a small work function is preferably used to facilitate electron injection into the organic material layer. Specifically, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiAl and LiF / Al or LiO2 / Al, but the present invention is not limited thereto.

As the hole injection layer material, it is preferable that HOMO (Highest Occupied Molecular Orbital) of the hole injection layer material be between the work function of the anode material and the HOMO of the surrounding organic layer . It is also preferable to use a material having a surface adhesion with the anode and a planarizing ability capable of alleviating the surface roughness of the anode. Materials having HOMO and LUMO (Lowest Unoccupied Molecular Orbital) values larger than the band gap of the light emitting layer and materials having high chemical stability and thermal stability are preferable. Specifically, the hole injection layer material may be selected from the group consisting of metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene Perylene based organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers may be used, but the present invention is not limited thereto.

As the hole transport layer material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is preferable. Materials having HOMO and LUMO values larger than the band gap of the light emitting layer and materials having high chemical stability and thermal stability are preferable. Specifically, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together may be used, but the present invention is not limited thereto.

The light emitting layer material is a material capable of emitting light in the visible light region by transporting holes and electrons from the hole transporting layer and the electron transporting layer, respectively. In the present invention, the iridium complex is used as the light emitting layer material.

In one preferred embodiment, the light emitting layer in the organic electroluminescent device of the present invention may be a host doped with the iridium complex as a dopant. In the case of single emission, efficiency and brightness are very low, and the molecules are brought close to each other, so that excimer characteristics other than the intrinsic characteristics of each molecule can be exhibited. As a result, a dopant material is doped on a host material It is preferable to use one light-emitting layer. When the dopant material is doped on the host material, the dopant material returns to the ground state and the light emitted from the host material returns to the ground state.

As the hole blocking layer material, a material larger than the HOMO value of the light emitting layer is preferable. Materials having high chemical stability and thermal stability are also desirable. Specifically, TPBi and BCP are mainly used, and CBP, PBD, PTCBI, and BPhen may be used, but the present invention is not limited thereto.

As the electron transport layer and the electron injection layer material, a material capable of injecting electrons from the cathode well and transferring the electrons to the light emitting layer is preferable. Materials with high chemical stability and thermal stability are also suitable. Specifically, Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complex, and the like may be used, but the present invention is not limited thereto.

The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

Hereinafter, the present invention will be described more specifically by way of Synthesis Examples and Examples. However, these synthesis examples and examples are provided only for the understanding of the present invention, and the scope of the present invention is not limited to these examples in any sense.

Synthesis Example 1: Preparation of compound 1

<Step 1>

2-aminobenzonitrile (1 eq), ethylene diamine (6 eq) and phosphorus pentasulfide (0.02 eq) were added to a dried round flask, and after filling with nitrogen sufficiently, xylene was added, and the mixture was refluxed for 40 hours .

Then, distilled water was added to complete the reaction. After extraction with dimethyl ether and distilled water, the organic layer was dried with anhydrous magnesium sulfate and filtered. The filtered organic layer was concentrated under reduced pressure and the resulting mixture was purified by column chromatography with ethyl acetate / hexane to obtain intermediate A.

<Step 2>

Intermediate A (1 eq) and benzaldehyde (1.1 eq) were added to a dried round flask, and after filling with nitrogen sufficiently, acetonitrile was added and the mixture was refluxed at room temperature for 72 hours.

Subsequently, the precipitate was filtered, washed with acetonitrile, toluene and ethyl ether to obtain an intermediate B.

<Step 3>

Intermediate B (1 eq, 0.2 mmol), acetonitrile (5 mL) and potassium permanganate (2.05 eq) were added to a round flask, and the mixture was refluxed with stirring for 12 hours.

Then, 1 mL of ethanol was added, and the reaction was terminated. After stirring for about 1 hour, the mixture was filtered through a Celite plug. After rinsing the Celite plug with dichloromethane, the obtained organic layer solution was concentrated under reduced pressure and purified by column chromatography with ethyl acetate / hexane to obtain intermediate C.

<Step 4>

Intermediate C (1 eq) and 0.1 eq of iridium () chloride were added to a dried round flask, and nitrogen was sufficiently charged, followed by 2-ethoxyethanol, and the mixture was refluxed at 250 ° C. for 24 hours.

The resulting mixture was purified by column chromatography with ethyl dichloromethane to give Compound 1. &lt; 1 &gt;

MALDI-TOF: m / z calcd for C ₄₈ H ₃₀ IrN ₉ : 925.03; found: 925.23

Synthesis Example 2: Preparation of Compound 2

Compound 2 was prepared in the same manner except that butane-2,3-diamine was used instead of ethylenediamine in < Step 1 > of Synthesis Example 1.

MALDI-TOF: m / z calcd for C ₅₄ H ₄₂ IrN ₉ : 1009.19; found: 1009.32

Synthesis Example 3: Preparation of Compound 3

Compound 3 was prepared in the same manner except that 1,2-diphenylethane-1,2-diamine was used instead of ethylenediamine in < Step 1 > of Synthesis Example 1.

MALDI-TOF: m / z calcd for C ₈₄ H ₅₄ IrN ₉ : 1381.6; found: 1381.41

Synthesis Example 4: Preparation of Compound 4

Compound 4 was prepared in the same manner except that 3,3,3-trifluoropropane-1,2-diamine was used instead of ethylenediamine in < Step 1 > of Synthesis Example 1.

MALDI-TOF: m / z calcd for C ₅₁ H ₂₇ F ₉ Ir ₉ : 1129.02; found: 1129.19

Synthesis Example 5: Preparation of Compound 5

Compound 5 was prepared in the same manner except that 2-amino-4-fluorobenzonitrile was used instead of 2-aminobenzonitrile in < Step 1 > in Synthesis Example 1.

MALDI-TOF: m / z calcd for C ₄₈ H ₂₇ F ₃ IrN ₉ : 979; found: 979.2

Synthesis Example 6: Preparation of Compound 6

Compound 6 was prepared in the same manner as in Synthesis Example 2 except that 2-amino-4-fluorobenzonitrile was used instead of 2-aminobenzonitrile in Step 1.

. MALDI-TOF: m / z calcd for C ₅₄ H ₃₉ F ₃ IrN ₉ : 1063.16; found: 1063.29

Synthesis Example 7: Preparation of Compound 7

Compound 7 was prepared in the same manner except that 2-amino-4-fluorobenzonitrile was used instead of 2-aminobenzonitrile in < Step 1 > in Synthesis Example 3.

MALDI-TOF: m / z calcd for C ₈₄ H ₅₁ F ₃ IrN ₉ : 1435.58; found: 1435.38

Synthesis Example 8: Preparation of Compound 8

Compound 8 was prepared in the same manner as in Synthesis Example 4, except that 2-amino-4-fluorobenzonitrile was used instead of 2-aminobenzonitrile in Step 1.

MALDI-TOF: m / z calcd for C ₈₁ H ₂₄ F ₁₂ IrN ₉ : 1182.99; found: 1183.16

Synthesis Example 9: Preparation of Compound 9

Compound 9 was prepared in the same manner except that 2-amino-4-methoxybenzonitrile was used instead of 2-aminobenzonitrile in < Step 1 > in Synthesis Example 1.

MALDI-TOF: m / z calcd for C ₅₁ H ₃₆ IrN ₉ O ₃ : 1015.11; found: 1015.26

Synthesis Example 10: Preparation of Compound 10

Compound 10 was prepared in the same manner except that 2-amino-4-methoxybenzonitrile was used instead of 2-aminobenzonitrile in < Step 1 > in Synthesis Example 2.

MALDI-TOF: m / z calcd for C ₅₇ H ₄₈ IrN ₉ O ₃ : 1099.27; found: 1099.35

Synthesis Example 11: Preparation of Compound 11

Compound 11 was prepared in the same manner except that 2-amino-4-methoxybenzonitrile was used instead of 2-aminobenzonitrile in < Step 1 > in Synthesis Example 3.

MALDI-TOF: m / z calcd for C ₈₇ H ₆₀ IrN ₉ O ₃ : 1471.68; found: 1471.45

Synthesis Example 12: Preparation of Compound 12

Compound 12 was prepared in the same manner except that 2-amino-4-methoxybenzonitrile was used instead of 2-aminobenzonitrile in < Step 1 > in Synthesis Example 4.

MALDI-TOF: m / z calcd for C ₅₄ H ₃₃ F ₉ IrN ₉ O ₃ : 1219.1; found: 1219.22

Example 1: Fabrication of organic electroluminescent device

Before deposition for device fabrication, a glass substrate coated with ITO (Indium Tin Oxide) thin film was cleaned (the impurities and the particulate matter on the surface were deformed by organics, the deterioration of interfacial properties between ITO and organic materials, The impurity is burned at the time of application or a phenomenon that the light is not partially or totally caused by the contact failure with the ITO is caused and the device life is shortened). In order to remove impurities such as organic substances, ionic substances, and metallic substances present on the substrate before the organic material deposition, the substrate was removed by ultrasonic cleaning for 5 minutes at room temperature with acetone, and then 5 parts by IPA (Isopropyl alcohol) Ultrasonic cleaning was performed for a minute and then dried using N ₂ gas.

HAT-CN, a hole injecting layer, and TAPC, a hole transporting material, were vacuum-deposited on the ITO transparent electrode thus prepared to a thickness of 500 nm, and then 12% of the compound 1 obtained in Synthesis Example 1 was added to mCBP as a light emitting layer. After vacuum deposition of BmPyPb as an electron transport layer to a thickness of 400 Å, Thickness of lithium fluoride (LiF) and 1200? Aluminum was deposited to form a cathode. Here, the deposition rate of the organic material was 1? / Sec, the deposition rate of lithium fluoride was 0.1? / Sec, and the deposition rate of aluminum was 1? / Sec.

The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m ² ), the luminescence brightness at a current density of 10 mA / cm ² , the luminous efficiency, and the like are shown in Table 1 below.

Example 2: Fabrication of organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 2 obtained in Synthesis Example 2 was used instead of Compound 1 as a light emitting layer dopant.

The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m ² ), the luminescence brightness at a current density of 10 mA / cm ² , the luminous efficiency, and the like are shown in Table 1 below.

Example 3: Fabrication of organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 3 obtained in Synthesis Example 3 was used instead of Compound 1 as a light emitting layer dopant.

The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m ² ), the luminescence brightness at a current density of 10 mA / cm ² , the luminous efficiency, and the like are shown in Table 1 below.

Example 4: Fabrication of organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 4 obtained in Synthesis Example 4 was used instead of Compound 1 as a luminescent layer dopant.

The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m ² ), the luminescence brightness at a current density of 10 mA / cm ² , the luminous efficiency, and the like are shown in Table 1 below.

.

Example 5: Fabrication of organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 5 obtained in Synthesis Example 5 was used instead of Compound 1 as a light emitting layer dopant.

The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m ² ), the luminescence brightness at a current density of 10 mA / cm ² , the luminous efficiency, and the like are shown in Table 1 below.

Example 6: Fabrication of organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 6 obtained in Synthesis Example 6 was used instead of Compound 1 as a light emitting layer dopant.

The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m ² ), the luminescence brightness at a current density of 10 mA / cm ² , the luminous efficiency, and the like are shown in Table 1 below.

Example 7: Fabrication of organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 7 obtained in Synthesis Example 7 was used instead of Compound 1 as a light emitting layer dopant.

The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m ² ), the luminescence brightness at a current density of 10 mA / cm ² , the luminous efficiency, and the like are shown in Table 1 below.

Example 8: Fabrication of organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound 8 obtained in Synthesis Example 8 was used instead of Compound 1 as a light emitting layer dopant.

The characteristics of the organic electroluminescent device such as the driving voltage (1Cd / m ² ), the luminescence brightness at a current density of 10 mA / cm ² , the luminous efficiency, and the like are shown in Table 1 below.

Comparative Example 1: Fabrication of organic electroluminescent device

An organic electroluminescent device was prepared in the same manner as in Example 1, except that FIrpic represented by the following formula (II) was used instead of Compound 1 as the luminescent layer dopant.

[Chemical Formula II] FIrpic

division compound Driving voltage

(V) Light emission luminance

(Cd / m2) Luminous efficiency

(Cd / A) Power efficiency

(lm / W)
CIE Pyrolysis temperature

(TGA) ( ^o C) Comparative Example 1 Firpic 4.5 1914 15.4 6.8 (0.17, 0.35) 300 Example 1 Synthesis Example 1 4.1 2020 16.4 8.1 (0.17, 0.25) 380 Example 2 Synthesis Example 2 3.5 2890 20.5 9.5 (0.17, 0.25) 354 Example 3 Synthesis Example 3 4.0 2360 17.9 8.4 (0.17, 0.25) 426 Example 4 Synthesis Example 4 3.6 2446 18.3 8.5 (0.17, 0.24) 347 Example 5 Synthesis Example 5 4.1 1952 16.8 7.3 (0.17, 0.24) 372 Example 6 Synthesis Example 6 3.8 2564 18.4 8.8 (0.17, 0.22) 326 Example 7 Synthesis Example 7 4.2 2235 16.2 7.2 (0.17, 0.23) 396 Example 8 Synthesis Example 8 3.7 2335 18.9 9.1 (0.17, 0.20) 332

As shown in Table 1, when an iridium complex according to the present invention is used as a light emitting layer material, an organic electroluminescent device is manufactured using organic electroluminescent materials such as low voltage, high efficiency, high brightness and high color purity based on excellent hole transporting and electron transporting ability It is possible to harmonize the various characteristics required for the device.

01: substrate
02: anode (or first electrode)
03: cathode (or second electrode)
04: Hole injection layer
05: Hole transport layer
06: light emitting layer
07: Electron transport layer
08: Electron injection layer

Claims (10)

An iridium complex represented by the following general formula (I)
(I)

In the formula (I)
Ar ₁ is a hydrogen atom substituted or unsubstituted with at least one of methyl, trifluoromethyl, phenyl and thiophene, Ar ₂ is substituted with at least one of methyl, ethyl, trifluoromethyl, phenyl, cyano and thiophene Or an unsubstituted hydrogen atom, each Ar ₁ may form a mutual condensation ring.
Ar ₃ is a hydrogen atom, methoxy or fluorine.
The method according to claim 1,
An iridium complex selected from the group of compounds represented by the following structural formulas:

The method according to claim 1,
Wherein the iridium complex is used as an organic material layer of an organic electroluminescent device.
The method of claim 3,
Wherein the iridium complex is used as an emission layer material of an organic electroluminescent device.
5. The method of claim 4,
Wherein the iridium complex is used as a dopant material of the light emitting layer of the organic electroluminescent device.
6. The method of claim 5,
Wherein the iridium complex is used as a blue dopant material in the organic electroluminescent light emitting layer.
(a) reacting a compound represented by the following formula (1) and a compound represented by the following formula (2) together with phosphorus pentasulfide to obtain a compound represented by the following formula (3);
(b) reacting the obtained compound represented by the following formula (3) with benzaldehyde to obtain a compound represented by the following formula (4);
(c) adding potassium permanganate and acetonitrile to the compound represented by the following formula (4) to obtain a compound represented by the following formula (5); And
(d) introducing iridium chloride and 2-ethoxyethanol into the obtained compound represented by the following formula (5) to obtain a compound represented by the following formula (I);
&Lt; RTI ID = 0.0 &gt; Iridium &lt; / RTI &gt;
Can be efficiently and economically manufactured through the steps.

[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

(I)

In the formula (I)
Ar ₁ is a hydrogen atom substituted or unsubstituted with at least one of methyl, trifluoromethyl, phenyl and thiophene, Ar ₂ is substituted with at least one of methyl, ethyl, trifluoromethyl, phenyl, cyano and thiophene Or an unsubstituted hydrogen atom, each Ar ₁ may form a mutual condensation ring.
Ar ₃ is a hydrogen atom, methoxy or fluorine.
1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the electrodes,
Wherein the one or more organic layers include a light emitting layer,
Wherein the light emitting layer comprises the iridium complex according to any one of claims 1 to 6. 9. The method of claim 8,
Wherein the light emitting layer is doped with a host material doped with the iridium complex.
9. The method of claim 8,
Wherein the at least one organic material layer further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

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