KR101736119B1 - Organic metal compound and organic electroluminescent devices comprising the same - Google Patents

Abstract

The present invention relates to a novel organometallic compound and an organic electroluminescent device including the organic electroluminescent device. The organic electroluminescent device including the organometallic compound according to the present invention has an excellent luminance, color purity and lifetime characteristics.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic metal compound and an organic electroluminescent device including the organic metal compound.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic metal compound and an organic electroluminescent device including the organic metal compound. More particularly, the present invention relates to an organic metal compound having excellent brightness, color purity and external quantum efficiency, and an organic electroluminescent device including the same.

In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. On the other hand, an organic light emitting diode (OLED), which is a new flat display device, is a display using a self-luminous phenomenon, has a large viewing angle, is slimmer and smaller than a liquid crystal display, And in recent years, application to a full-color display or illumination is expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as the light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of a stable and efficient organic material layer material for an organic electroluminescence device has not been sufficiently developed yet. Therefore, there is a continuing need in the art for the development of new materials.

SUMMARY OF THE INVENTION The present invention provides an organometallic compound having excellent light emission luminance and color purity and excellent external quantum efficiency.

A second object of the present invention is to provide an organic electroluminescent device including the organometallic compound.

In order to accomplish the first technical object, the present invention provides an organometallic compound represented by the following general formula (1).

In Formula 1,

X and Y each independently represent a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, Or a substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylamino group having 3 to 40 carbon atoms, a substituted or unsubstituted C1 to C40 alkyl group having 1 to 40 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 40 carbon atoms, a substituted or unsubstituted carbon number 3 to 40 heteroaryl groups, substituted or unsubstituted germanium groups, substituted or unsubstituted phosphorus, and substituted or unsubstituted boron,

Ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,

A is a single bond or a substituted or unsubstituted alkylene of 1 to 4 carbon atoms,

L is a single or double ligand,

o, p and n are each independently an integer of 1 to 4;

In order to solve the second technical problem, the present invention provides a semiconductor device comprising: an anode; Cathode; And a layer including an organometallic compound represented by the general formula (1), which is interposed between the anode and the cathode.

The organic electroluminescent device comprising the organometallic compound represented by Chemical Formula 1 according to the present invention in an organic material layer can be used for display and illumination because of excellent luminance, color purity and external quantum efficiency.

1 is a schematic view of an organic electroluminescent device according to one embodiment of the present invention.
Description of the Related Art
10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

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

The organometallic compound according to the present invention is characterized by being represented by the above formula (1).

In the organometallic compound according to the present invention, the substituents of the above formula (1) will be described in more detail as follows.

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Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, a " alkylsilyl group "hereinafter), a substituted or unsubstituted amino group _{(-NH 2, -NH (R)} , -N (R ') (R''), where R, R' and R" are each independently a carbon number A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms (for example, an alkyl group having 1 to 24 carbon atoms , An alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, An aryl group having from 5 to 24 carbon atoms, an aryl group having from 5 to 24 carbon atoms, an arylalkyl group having from 6 to 24 carbon atoms, a heteroaryl group having from 3 to 24 carbon atoms, or a heteroarylalkyl group having from 3 to 24 carbon atoms.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And can be substituted with substituents similar to those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

Specific examples of the aryl group as the substituent group used in the compound of the present invention include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, Examples of the aryl group include phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, , Anthryl group, phenanthryl group, pyrenyl group, fluorenyl group, tetrahydronaphthyl group and the like, which may be substituted with the same substituents as those in the case of the alkyl group.

Specific examples of the heteroaryl group used as the substituent in the compound of the present invention include pyridinyl, pyrimidinyl, triazinyl, indolinyl, quinolinyl, pyrrolidinyl, piperidinyl, An oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, a thiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group, a benzoimidazole group, And at least one of the hydrogen atoms of the heteroaryl group may be substituted with the same substituent as the alkyl group.

In the present invention, the term "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heteroaryl, Substituted or unsubstituted with at least one substituent selected from the group consisting of an acetylene group, a nitrile group and an acetylene group.

The organometallic compound according to the present invention may be any one of compounds represented by the following formulas (1-1) to (1-4).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

X, Y, A, L, o, p and n are the same as defined in the above formula (1).

In the organometallic compound according to the present invention, L in Formula 1 may be any one of the ligands represented by the following structural formulas.

In the ligand, each of R ₁ to R ₁₉ independently represents a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, Substituted or unsubstituted C1-C40 alkoxy group, substituted or unsubstituted C1-C40 alkylamino group, substituted or unsubstituted C6-C40 arylamino group, substituted or unsubstituted C3-C40 heteroarylamino group, A substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 40 carbon atoms, A substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, a substituted or unsubstituted germanium group, a substituted or unsubstituted phosphorus, and a substituted or unsubstituted boron Group is selected from and adjacent to form a condensed ring of an aliphatic, aromatic, heterocyclic aliphatic or heteroaromatic bonded to each other.

Specifically, the organometallic compound according to the present invention may be any one of compounds represented by the following Chemical Formulas (2) to (149).

The method for producing an organometallic compound according to the present invention is specifically shown in the following Examples.

The present invention also relates to a fuel cell comprising an anode; Cathode; And a layer including an organometallic compound represented by the general formula (1), which is interposed between the anode and the cathode.

In this case, the layer containing the organic metal compound is preferably a light emitting layer between the anode and the cathode, and a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer, ≪ RTI ID = 0.0 > and / or < / RTI >

According to another embodiment of the present invention, the thickness of the light emitting layer is preferably 0.5 nm to 500 nm, and the light emitting layer further comprises 1,3-Bis (N-carbazolyl) benzene (mCP) can do.

[1,3-Bis (N-carbazolyl) benzene]

As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is widely used.

In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD).

A HIL (Hole Injection Layer) may be additionally deposited on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenylamino) triphenylamine).

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

The organic electroluminescent device according to the present invention can be used for a display device, a display device, an element for a single color or a white light, and the like.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic electroluminescent device of the present invention and its manufacturing method will be described as follows. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30. 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 to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

According to another embodiment of the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited thereto.

< Example >

< Synthetic example  1> Preparation of the compound represented by the formula (6)

1) Synthesis of the compound represented by the formula 1-a

The compound represented by the formula (1-a) was synthesized by the following Reaction Scheme 1.

[Reaction Scheme 1]

30.0 g (0.174 mol) of 2-bromo-4-methylpyridine and 100 mL of triethylamine were added to a 250 mL round-bottomed flask, and 21.0 g (0.210 mol) of chlorotrimethylsilane was slowly added dropwise thereto. Lt; / RTI &gt; After removal of the solvent, the compound represented by the formula (I-a) was synthesized by using column chromatography with dichloromethane and hexane developing solvent. yield; 33.6 g (79%).

2) Synthesis of the compound represented by the formula 1-b

A compound represented by the formula 1-b was synthesized by the following Reaction Scheme 2.

[Reaction Scheme 2]

25.0 g (0.22 mol) of 2,6-difluoropyridine and 170 mL of glacial acetic acid were placed in a 1 L round bottom flask, followed by the addition of 29.6 g (0.87 mol) of 30% hydrogen peroxide and stirring at 70 ° C for 5 hours Respectively. 7.4 g of 30% aqueous hydrogen peroxide was added at the same temperature and heated at 75 캜 for 8 hours. After the temperature was lowered to room temperature, acetone (700 mL) was added to prepare a white solid of the formula 1-b. yield; 24.2 g (85%).

3) Synthesis of the compound represented by the formula 1-c

The compound represented by the formula 1-c was synthesized by the following Reaction Scheme 3.

[Reaction Scheme 3]

24.0 g (0.18 mol) of the compound represented by the formula (1-b) obtained in the above reaction formula 2 and 240 mL of THF were placed in a 500 mL round bottom flask and then cooled to -78 ° C. To this solution, 88.2 g (0.22 mol) of LDA was slowly added dropwise, and the mixture was stirred at the same temperature for 2 hours, and 32.1 g (0.22 mol) of triethyl borate was slowly added thereto. The reaction product was warmed to room temperature, stirred for 12 hours, and 1M NaOH (400 mL) was added thereto. After the aqueous layer was separated, the aqueous layer was adjusted to pH 8 with 2N HCl and extracted with ethyl acetate (100 mL). The aqueous layer was adjusted to pH 6.5 and extracted twice with ethyl acetate. The aqueous layer was adjusted to pH 4 And extracted twice with ethyl acetate. The extract was dried and the solvent was removed, and recrystallized from ethyl acetate and ether to synthesize the compound represented by formula (I-c). yield; 22.6 g (71%).

4) Synthesis of the compound represented by the formula (1-d)

The compound represented by the formula 1-d was synthesized by the following Reaction Scheme 4.

[Reaction Scheme 4]

In a 1 L round bottom flask, 33.5 g (0.137 mol) of the compound represented by the formula 1-a obtained from the above reaction schemes 1 and 3, 28.8 g (0.165 mol) of the compound represented by the formula 1-c, , Potassium carbonate (37.9 g, 0.274 mol), THF (600 mL), and water (300 mL) were placed and refluxed for 12 hours. The solution was cooled to room temperature, and the organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and ethyl acetate as eluent to obtain a compound represented by the formula (1-d). yield; 28.9 g (71%).

5) Synthesis of the compound represented by the formula 1-e

The compound represented by the formula 1-e was synthesized according to the following Reaction Scheme 5.

[Reaction Scheme 5]

20.0 g (0.067 mol) of the compound represented by the formula 1-d obtained from the above reaction formula 4, 10.0 g (0.034 mol) of IrCl ₃ .xH ₂ O, 210 mL of ethoxyethanol and 70 mL of water were added to a 250- And the mixture was refluxed at 120 ° C for 18 hours. The temperature was lowered to room temperature, poured into water (2L), and the resulting solid was filtered, washed with water, methanol, ether and hexane to prepare the compound represented by the formula (1-e). yield; 22.4 g (82%).

6) Synthesis of Compound Represented by Formula 6

The compound represented by Formula 6 was synthesized by the following Reaction Scheme 6.

[Reaction Scheme 6]

20.0 g (0.012 mol) of the compound represented by the formula 1-e obtained from the above reaction formula 5, 11.0 g (0.037 mol) of the compound represented by the formula 1-d, 8.1 g (0.037 mol) of the trifluoromethane silver mol) were stirred at 200 &lt; 0 &gt; C for 5 hours. After lowering the temperature, the reaction product was dissolved in dichloromethane, and the resulting solid was separated by column chromatography using a developing solvent of hexane and ethyl acetate to obtain a compound represented by the formula (6). yield; 6.8 g (51%).

MS (MALDI-TOF): m / z 1072 [M] &lt; + &gt;; Anal. Calcd. C ₄₂ H ₄₅ F ₆ IrN ₆ O ₃ Si ₃ : C, 47.04; H, 4.23; N, 7.84. Found: C, 46.08; H, 4.16; N, 7.91.

< Synthetic example  2> Preparation of the compound represented by the formula (9)

1) Synthesis of the compound represented by the formula 2-a

The compound represented by the formula 2-a was synthesized according to the following Reaction Scheme 7.

[Reaction Scheme 7]

26.6 g (0.152 mol) of the compound represented by the formula 1-c, 20.0 g (0.123 mol) of 2-bromopyridine and 2.9 g (0.003 mol) of tetrakistriphenylphosphine palladium were added to a 1 L round bottom flask, , Potassium carbonate (35.0 g, 0.253 mol), THF (400 mL) and water (200 mL), and the mixture was refluxed for 12 hours. The solution was cooled to room temperature and the organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and ethyl acetate as eluent. The solid was dried to produce the compound represented by the formula (2-a). yield; 19.7 g (75%).

2) Synthesis of the compound represented by the formula 2-b

The compound represented by the formula (2-b) was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

15.0 g (0.072 mol) of the compound represented by the formula 2-a, 10.8 g (0.036 mol) of IrCl ₃ .xH ₂ O, 210 mL of ethoxyethanol and 70 mL of water were added to a 500 mL round bottom flask, And the mixture was refluxed at 120 ° C for 18 hours. The temperature was lowered to room temperature, poured into water (1.8 L), and the resulting solid was filtered, washed with water, methanol, ether, and hexane to give the compound represented by formula (2-b). yield; 15.9 g (69%).

3) Synthesis of Compound Represented by Formula 9

The compound represented by the general formula (9) was synthesized by the following Reaction Scheme (9).

[Reaction Scheme 9]

10.0 g (0.008 mol) of the compound represented by the formula 2-b obtained from the above reaction formula 8, 4.1 g (0.019 mol) of the compound represented by the formula 2-a and 4.3 g (0.019 moles) of the trifluoromethane silver were added to a 50 mL round- mol) were stirred at 200 &lt; 0 &gt; C for 5 hours. After the temperature was lowered, the reaction product was dissolved in dichloromethane, and the solid was separated by column chromatography using an elution solvent of hexane and ethyl acetate to obtain a compound represented by the formula (9). yield; 3.5 g (54%).

MS (MALDI-TOF): m / z 814 [M] &lt; + &gt;; Anal. Calcd. _{C 30 H 15 F 6 IrN 6} O 3: C, 44.28; H, 1.86; N, 10.33. Found: C, 44.15; H, 1.79; N, 10.40.

< Synthetic example  3> Preparation of the compound represented by the formula (36)

The compound represented by the formula (36) was synthesized according to the following reaction formula (10).

[Reaction Scheme 10]

This example is similar to the preparation of the compound represented by the formula (9) except that 2-bromo-4-naphthopyridine is used instead of 2-bromopyridine in Scheme 7 to introduce the main ligand, The compound represented by formula (36) was synthesized. yield; 3.3 g (51%).

MS (MALDI-TOF): m / z 949 [M] &lt; + &gt;; Anal. Calcd. C ₃₀ H ₁₂ F ₆ IrN ₉ O ₉ : C, 37.98; H, 1.27; N, 13.29. Found: C, 37.16; H, 1.21; N, 13.31.

< Synthetic example  4> Preparation of the compound represented by the formula (57)

1) Synthesis of the compound represented by the formula 4-a

The compound represented by the formula 4-a was synthesized according to the following Reaction Scheme 11.

[Reaction Scheme 11]

Formic acid (40 mL) was added to a 100 mL round bottom flask, and 23.4 g (0.135 mol) of 2-bromo-5-aminopyridine was slowly added thereto at 0 ° C. or lower. 34 mL (0.420 mol) of formaldehyde was added thereto and refluxed for 2 hours . The temperature was lowered to room temperature, poured into 1N KOH (200 mL) aqueous solution, extracted with ether, and concentrated under reduced pressure. The solid was separated by column chromatography using a developing solvent of dichloromethane and then dried to prepare a compound represented by the formula (4-a). yield; 10.4 g (40%).

2) Synthesis of the compound represented by the formula 4-b

A compound represented by the formula 4-b was synthesized by the following Reaction Scheme 12.

[Reaction Scheme 12]

25.0 g (0.19 mol) of the compound represented by the formula 1-b obtained from the above reaction formula 2 and 240 mL of THF were placed in a 500 mL round bottom flask, and then cooled to -78 ° C. To this solution, 88.2 g (0.22 mol) of LDA was slowly added dropwise, and the mixture was stirred at the same temperature for 2 hours. 58.1 g (0.22 mol) of iodine was dissolved in THF (100 mL) and slowly added. The reaction product was heated to room temperature, stirred for 12 hours, and then terminated with distilled water. After extracting twice with ethyl acetate, the extract was dried and the solvent was removed, followed by column chromatography using ethyl acetate and a developing solvent of hexane. The obtained solid was dried to prepare a compound represented by the formula 4-b. yield; 35.4 g (71%).

3) Synthesis of the compound represented by the formula 4-c

The compound represented by the formula 4-c was synthesized by the following Reaction Scheme 13.

[Reaction Scheme 13]

2.8 g (0.18 mol) of magnesium and 50 mL of THF were placed in a 500 mL round bottom flask and 25.0 g (0.10 mol) of the compound represented by the formula 4-b obtained from the above reaction scheme 12 was dissolved in THF (240 mL) And then refluxed for 1 hour. After the temperature was lowered to room temperature, 12.5 g (0.18 mol) of the compound represented by the formula 4-a obtained from the reaction formula 11 was dissolved in THF (100 mL) and the mixture was stirred for 10 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and the organic layer was dried and concentrated under reduced pressure, and then separated by column chromatography using an ethyl acetate developing solvent. The obtained solid was dried to prepare a compound represented by the formula 4-c. yield; 15.1 g (61%).

4) Synthesis of the compound represented by the formula 4-d

The compound represented by the formula 4-d was synthesized according to the following Reaction Scheme 14.

[Reaction Scheme 14]

15.0 g (0.06 mol) of the compound represented by the formula 4-c obtained from the above reaction scheme 13 was dissolved in methanol (50 mL) and sulfuric acid (10 mL), and 10% Pd / C (2 g) was added to a 100 mL round bottom flask. Hydrogen was added at room temperature and stirred until hydrogen was consumed. The catalyst was then filtered and neutralized with a 10% aqueous sodium hydroxide solution, followed by extraction with dichloromethane, followed by drying and concentration under reduced pressure. Ethyl acetate eluting solvent, and the resulting solid was dried to prepare a compound represented by the formula (4-d). yield; 6.2 g (45%).

5) Synthesis of compound represented by formula (57)

The compound represented by formula (57) was synthesized by the following reaction scheme (15).

[Reaction Scheme 15]

6.0 g (0.023 mol) of the compound represented by the formula 4-d obtained from the reaction formula 14, 1.7 g (0.006 mol) of IrCl ₃ .xH ₂ O and 5.0 g (0.023 mol) of trifluoromethane silver were added to a 50 mL round- Was stirred at 200 &lt; 0 &gt; C for 5 hours. After the temperature was lowered, the reaction product was dissolved in dichloromethane, and then the product was separated by column chromatography using hexane and ethyl acetate. The resulting solid was dried to produce a compound represented by the formula (57). yield; 2.6 g (46%).

MS (MALDI-TOF): m / z 985 [M] &lt; + &gt;; Anal. Calcd. C ₃₉ H ₃₆ F ₆ IrN ₉ O ₃ : C, 47.56; H, 3.68; N, 12.80. Found: C, 46.98; H, 3.57; N, 12.91.

< Synthetic example  5> Preparation of the compound represented by the general formula (105)

The compound represented by Formula 105 was synthesized by the following Reaction Scheme 16.

[Reaction Scheme 16]

15.0 g (0.012 mol) of the compound represented by the formula 2-b obtained from the above reaction formula 8, 4.5 g (0.029 mol) of 2-phenylpyridine and 16.1 g (0.117 mol) of sodium carbonate were dissolved in ethoxyethanol (150 mL) in a 100 mL round- And the mixture was refluxed at 120 ° C for 18 hours. After the temperature was lowered, the reaction product was poured into water (1 L), and the resulting solid was filtered, dried, and then separated by column chromatography using dichloromethane and a hexane developing solvent. The obtained solid was dried to produce a compound represented by the formula (105). yield; 5.8 g (65%).

MS (MALDI-TOF): m / z 761 [M] &lt; + &gt;; Anal. Calcd. C ₃₁ H ₁₈ F ₄ IrN ₅ O ₂ : C, 48.94; H, 2.38; N, 9.21. Found: C, 48.87; H, 2.29; N, 9.19.

< Synthetic example  6> Preparation of the compound represented by the formula (115)

1) Synthesis of the compound represented by the formula 6-a

A compound represented by the formula 6-a was synthesized by the following Reaction Scheme 17.

[Reaction Scheme 17]

10.0 g (0.05 mol) of the compound represented by the formula 4-a, 10.4 g (0.06 mol) of the compound represented by the formula 1-c obtained from the above reaction formulas 3 and 11, _{(Pd (PPh 3) 4)} 0.3g (0.002mol), potassium carbonate _{(K 2 CO 3) 13.8g (} 0.10mol), THF (200mL), into a water (100mL) was refluxed for 12 hours. The solution was cooled to room temperature and the organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography using hexane and ethyl acetate as eluent. The solid was dried to produce the compound represented by formula 6-a. yield; 9.3 g (74%).

2) Synthesis of the compound represented by the formula 6-b

The compound represented by the formula 6-b was synthesized by the following Reaction Scheme 18.

[Reaction Scheme 18]

8.9 g (0.036 mol) of the compound represented by the formula 6-a obtained from the above reaction formula 17, 5.3 g (0.018 mol) of IrCl ₃ .xH ₂ O, 45 ml of ethoxyethanol and 15 ml of water were added to a 100 ml round bottom flask, And the mixture was refluxed at 120 ° C for 18 hours. The temperature was lowered to room temperature, poured into water (500 mL), and the resulting solid was filtered and washed with water, methanol, ether, and hexane to prepare a compound represented by the formula 6-b. yield; 9.9 g (77%).

3) Synthesis of the compound represented by the formula (115)

The compound represented by the formula (115) was synthesized by the following reaction scheme (19).

[Reaction Scheme 19]

2.2 g (0.015 mol) of 2-phenylimidazole and 6.6 g (0.062 mol) of sodium carbonate were added to a 50-mL round-bottomed flask with ethoxyethanol (0.006 mol) 30 mL), and the mixture was refluxed at 120 DEG C for 18 hours. The temperature is reduced and the reaction is poured into water (200 mL) and the resulting solid is filtered off and dried. The solid was separated by column chromatography with ethyl acetate and a developing solvent of hexane and dried to give the compound represented by formula (115). yield; 3.2 g (61%).

MS (MALDI-TOF): m / z 837 [M] &lt; + &gt;; Anal. Calcd. C ₃₂ H ₂₆ F ₄ IrN ₉ O ₂ : C, 45.93; H, 3.13; N, 15.06. Found: C, 45.25; H, 3.08; N, 15.11.

< Example  1 to 6> The organic electroluminescent device  Produce

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr. Then, an organic material was injected onto the ITO using DNTPD (700 Å), NPD (300 Å), mCP + 300 Å), Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å).

[DNTPD]

[NPD]

[mCP]

[Alq ₃ ]

< Comparative Example  1>

The organic electroluminescent device for the comparative example was fabricated in the same manner except that the following FIrpic was used instead of the compound produced by the invention in the device structures of Examples 1 to 6 above.

[FIrpic]

[Table 1]

From the results of Examples 1 to 6, Comparative Example 1 and Table 1, the compound represented by Formula 1 according to the present invention exhibits excellent external quantum efficiency as compared with FIrpic, which is widely used as a phosphorescence emitting material, Display device, illumination, and the like.

Claims (12)

An organometallic compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X and Y each independently represent a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms, Or a substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylamino group having 3 to 40 carbon atoms, a substituted or unsubstituted C1 to C40 alkyl group having 1 to 40 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 40 carbon atoms, a substituted or unsubstituted carbon number 3 to 40 heteroaryl groups, substituted or unsubstituted germanium groups, substituted or unsubstituted phosphorus, and substituted or unsubstituted boron,
Ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,
A is a single bond or a substituted or unsubstituted alkylene of 1 to 4 carbon atoms,
L is a single or double ligand,
o, p and n are each independently an integer of 1 to 4; delete The method according to claim 1,
Wherein the organometallic compound is represented by any one of the following Chemical Formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

X, Y, A, L, o, p and n are the same as defined in the above formula (1). The method according to claim 1,
Wherein L in the above formula (1) is any one of the ligands represented by the following structural formulas:

In the ligand, each of R ₁ to R ₁₉ independently represents a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, Substituted or unsubstituted C1-C40 alkoxy group, substituted or unsubstituted C1-C40 alkylamino group, substituted or unsubstituted C6-C40 arylamino group, substituted or unsubstituted C3-C40 heteroarylamino group, A substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 40 carbon atoms, A substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, a substituted or unsubstituted germanium group, a substituted or unsubstituted phosphorus, and a substituted or unsubstituted boron Group is selected from and adjacent to form a condensed ring of an aliphatic, aromatic, heterocyclic aliphatic or heteroaromatic bonded to each other. The method according to claim 1,
Wherein the organometallic compound is any one of compounds represented by the following Chemical Formulas 2 to 149:

Anode;
Cathode; And
And an organic metal compound layer interposed between the anode and the cathode. The method according to claim 6,
Wherein the layer containing the organic metal compound is a light emitting layer between the anode and the cathode. 8. The method of claim 7,
Wherein at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode. 8. The method of claim 7,
Wherein the thickness of the light emitting layer is 0.5 nm to 500 nm. 8. The method of claim 7,
Wherein the light emitting layer further comprises 1,3-Bis (N-carbazolyl) benzene (mCP) having the following structural formula:
[1,3-Bis (N-carbazolyl) benzene]

9. The method of claim 8,
Wherein at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecular deposition method or a solution process. The method according to claim 6,
Wherein the organic electroluminescent device is used in a display device, a display device, or a device for monochromatic or white illumination.

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