KR101065311B1 - Metal compound and organic electroluminescence display employing the same - Google Patents

Abstract

The present invention provides an iridium compound which can be used as a light emitting material of an organic electroluminescent device. When the iridium compound of the present invention is applied to an organic electroluminescent device, it is excellent in luminous efficiency, brightness, color purity, and lifespan, thereby obtaining highly efficient device characteristics.

Description

Metal compound and organic electroluminescent device using the same {Metal compound and organic electroluminescence display employing the same}

1 illustrates a structure of an organic electroluminescent device according to an embodiment of the present invention,

2 is a diagram showing a photoluminescence (PL) spectrum in a chloroform solvent of a material represented by Chemical Formula 8 of the present invention.

3 is a view showing EL measurement luminance vs. lifetime data of the organic electroluminescent compound represented by Formula 13 of the present invention,

4 is a view showing a current vs. voltage change obtained at 600 cd / m ² when measuring EL (Electroluminescence) of the organic electroluminescent compound represented by Chemical Formula 13 of the present invention.

FIG. 5 is a diagram showing a PL (photoluminescence) spectrum in a chloroform solvent of a material represented by Chemical Formula 13 of the present invention. FIG.

The present invention relates to a metal compound and an organic electroluminescent device using the same, and more particularly, to an organic electroluminescent compound that can be used in an organic electroluminescent device having improved brightness and an organic electroluminescent device employing the organic film using the same. .

A general organic electroluminescent device has an anode in which an anode is formed on a substrate, and a hole transporting layer, a light emitting layer, an electron transporting layer and a cathode are sequentially formed on the anode. Here, the hole transport layer, the light emitting layer and the electron transport layer are organic thin films made of an organic compound.

The driving principle of the organic EL element having the structure as described above is as follows.

When voltage is applied between the anode and the cathode, holes injected from the anode are moved to the light emitting layer via the hole transport layer. On the other hand, electrons are injected into the light emitting layer from the cathode via the electron transport layer, and carriers are recombined in the light emitting layer to generate excitons. The excitons change from the excited state to the ground state, whereby the molecules of the light emitting layer emit light to form an image. The light emitting material is classified into a fluorescent material using excitons in a singlet state and a phosphorescent material using a triplet state according to its light emitting mechanism. Phosphorescent materials generally have an organic-inorganic compound structure containing heavy atoms, and the heavier atoms cause the triplet state of excitons, which were originally prohibited, to phosphorescence. Phosphorescent materials can use triplet excitons with 75% probability of production and can have much higher luminous efficiency than fluorescent materials using 25% singlet excitons.                         

Recently, various phosphorescent materials using iridium or platinum metal compounds have been published as organic electroluminescent materials using iridium compounds. As a blue light emitting material, (4,6-F2ppy) 2Irpic and the like have been developed, but the light emitting color is in the sky blue region and in particular, the shoulder peak is very large, and thus the color purity y value tends to be increased. In addition, due to the absence of a host material suitable for a blue material, there is a problem of very low efficiency and lifetime compared to the red, green phosphorescent material.

In addition, the red light emitting material has been reported on the homomoletic structure of iridium compounds using a phenyl-thiophen ligand or a phenyl-1-isoquinoline (piq) ligand (US 20030072964A and US 20030068526A), an organic electroluminescent device characteristic of an iridium compound of a derivative in which F is introduced into a piq ligand (US 20030189216A).

However, the above-mentioned light emitting materials still have various problems as high efficiency, high brightness, and long life materials, and thus there is a continuous demand for research on materials having excellent light emitting characteristics.

The technical problem to be achieved by the present invention is to provide a novel metal compound having luminescent properties that can solve the above problems.

Another object of the present invention is to provide an organic electroluminescent device having improved luminance, efficiency and lifespan by using the above-described light emitting compound.

In order to achieve the above technical problem, the present invention provides a metal compound comprising a bidentate ligand represented by the following formula (1).

[Formula 1]

Wherein R ₁ to R ₉ are each independently hydrogen, cyano group, hydroxy group, thiol group, halogen atom, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C1-C30 alkoxy group , A substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C6-C30 aryloxy group, Substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C2-C30 heteroarylalkyl group, substituted or unsubstituted C2-C30 heteroaryloxy group, substituted or unsubstituted C5-C30 cyclo Alkyl group, substituted or unsubstituted C2-C30 heterocycloalkyl group, substituted or unsubstituted C1-C30 alkylcarbonyl group, substituted or unsubstituted C7-C30 arylcarbonyl group, C1-C30 alkylthio group or -Si ( R ') (R ") (R"') (wherein R 'and R''are independently of each other hydrogen or an alkyl group of C1-C30), -N (R ') (R'') (wherein R' and R '' is hydrogen or an alkyl group of C1-C30 irrespective of each other), and in the R ₁ ~ R ₄ and R ₆ ~ R ₉ Two or more selected may be linked to each other to form an unsaturated or saturated ring.

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

The present invention provides a metal compound comprising a bidentate ligand represented by Formula 1 above.

In Formula 1, two or more selected from R ₁ to R ₄ and R ₆ to R ₉ may be linked to each other to form an unsaturated or saturated ring, wherein the ring may be a C5-C10 carbon ring or C1-C10 Can form a hetero ring. The heterocycle may include heteroatoms such as nitrogen, phosphorus, and oxygen.

The bidentate ligand is preferably a compound represented by the following Formula (2).

[Formula 2]

Wherein R 'and R ₅ are independently of each other hydrogen or an alkyl group of C1-C5, and R "is hydrogen, a C1-C5 alkyl group, a halogen atom or a cyano group, a methoxy group, a trifluoromethyl group.

The present invention provides a metal compound represented by the following Chemical Formula 3, wherein the bidentate ligand represented by Chemical Formula 1 is bonded to a metal.

(3)

Wherein R ₁ to R ₉ are as defined in Formula 1,

M is Ir, Os, Pt, Pb, Re, or Ru,

X is a monoanionic bidentate ligand,

m is 3 and n is 0, 1 or 2.

Although X is not particularly limited, acetylacetonate (acac), hexafluoroacetylacetonate (hfacac), salicylidene (sal), picoly, as shown in Formula 5 below. Picolinate (pic), 8-hydroxyquinolinate (hquin), α-amino acid L-proline (L-pro), dibenzoylmethane (dbm), tetramethylheptanedionate ( tetrametylheptanedionate (tmd), 1- (2-hydroxyphenyl) pyrazolate (1- (2-hydoxyphenyl) pyrazolate: oppz) 3-isoquinolinecarboxylate (3-iq), 1,5-dimethyl- 3-pyrazolecarboxylate (1,5-dimethyl-3-pyrazolecarboxylate: dm3PC), phenylpyrazole (ppz), quinolinecarboxylate (quin), phenylpyridine (ppy), benzoquinoline (benzoquinoline: bzq), a form of 5-phenyl-phenylpyridine (phppy) It can be given.

[Chemical Formula 5]

In the metal compound represented by Chemical Formula 3, M is iridium, and there is a metal compound represented by Chemical Formula 4 below.

[Formula 4]

Wherein R ₁ to R ₉ are as defined in Formula 1,

X is a monoanionic bidentate ligand, preferably selected from one of the groups represented by the above-mentioned formula (5),                     

m is 3 and n is 0, 1 or 2.

The iridium compound of Formula 4 is excellent as a light emitting property as a light emitting material and is useful as a red phosphorescent material of an organic electroluminescent device.

Examples of the R ₁ to R ₉ containing moiety in the general formulas (1) to (4) include the following types of groups.

The compound of Formula 4 is preferably a compound represented by the following formula (6).

[Formula 6]

Wherein R 'and R ₅ are independently of each other hydrogen or an alkyl group of C1-C5,

R ″ is hydrogen, a C1-C5 alkyl group, a halogen atom, cyano group, methoxy, or trifluoromethyl group,

X is selected from the group represented by the above formula (5),

m is 3 and n is 0, 1 or 2.

The compound of Formula 4 is particularly preferably a compound represented by the following Formula 7.

 [Formula 7]

Wherein R and R ₅ are independently of each other hydrogen or an alkyl group of C1-C5,

R ₆ , R ₇ , and R ₈ are each independently hydrogen, a C1-C5 alkyl group, a halogen atom or a cyano group, a methoxy group, or a trifluoromethyl group,

X is selected from the group represented by the following formula,

m is 3 and n is 0 or 1.

In the present invention, preferred examples of the iridium compound represented by the formula (4) include compounds represented by the following formulas (8A to 27A).

[Formula 8A] [Formula 9A] [Formula 10A] [Formula 11A] [Formula 12A]

[Formula 13A] [Formula 14A] [Formula 15A] [Formula 16A]

[Formula 17A] [Formula 18A]

[Formula 19A] [Formula 20A]

[Formula 21A] [Formula 22A] [Formula 23A] [Formula 24A] [Formula 25A]

[Formula 26A] [Formula 27A]

In the above formula, R is hydrogen, a C1-C5 alkyl group, a halogen atom or a cyano group, methoxy, trifluoromethyl group.

It is particularly preferable that the compounds of the formulas 8 to 27 are compounds represented by the following formulas.

[Formula 8] [Formula 9] [Formula 10] [Formula 11] [Formula 12]

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

       [Formula 17] [Formula 18] [Formula 19] [Formula 20]

  [Formula 21] [Formula 22] [Formula 23] [Formula 24] [Formula 25]

[Formula 26] [Formula 27]

It is particularly preferred that the compounds are compounds represented by the following formula (8) or (13).

[Formula 8] [Formula 13]

Among the metal compounds of the present invention described above, the iridium compound represented by the formula (4) is used as a red light emitting material, in particular as a dopant, and thus has excellent energy transfer, thereby showing high efficiency.

Iridium compound represented by the formula (4) of the present invention can be prepared using the method of the citation (synthesis of cinoline: SYNTHETIC COMMUNICATIONS 22 (4) 545-551 1992, Ir complex synthesis: US20030068526A), the citations of this invention Is incorporated by reference in

Among the metal compounds of the present invention, a compound of Formula 25 will be described as an example.

First, a compound represented by the following Chemical Formula 28 is synthesized.                     

[Formula 28]

Subsequently, the compound of Formula 28 may be reacted with Ir (acac) ₃ to synthesize a metal compound having m of 3 and n of 0.

In addition, by reacting the compound of Formula 28 with IrCl 2 to form a corresponding dimer metal complex, and then reacted with a compound (XH) containing a ligand X it can be a metal compound of m is 2 and n is 1.

In addition to the compound of formula 25, the remaining compounds may be prepared according to similar methods.

Specific examples of the unsubstituted C1-C30 alkyl group used in the chemical formula of the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like, and at least one of the alkyl groups Hydrogen atom is halogen atom, hydroxy group, nitro group, cyano group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group of C1-C30, C1-C30 Alkenyl group, C1-C30 alkynyl group, C6-C30 aryl group, C7-C30 arylalkyl group, C2-C20 heteroaryl group, or C3-C30 heteroarylalkyl group can be substituted.

Specific examples of the unsubstituted C1-C30 alkoxy group used in the chemical formula of the present invention include methoxy, ethoxy, phenyloxy, cyclohexyloxy, naphthyloxy, isopropyloxy, diphenyloxy, and the like. At least one hydrogen atom of these alkoxy groups may be substituted with the same substituent as in the alkyl group described above.                     

Unsubstituted aryl groups used in the formulas of the present invention may be used alone or in combination to mean 6 to 30 aromatic carbon rings containing one or more rings, which rings may be attached or fused together in a pendant manner. Can be. Examples of aryl include phenyl, naphthyl, tetrahydronaphthyl and the like. At least one hydrogen atom in the aryl group may be substituted with the same substituent as in the alkyl group described above.

Examples of the unsubstituted aryloxy group used in the chemical formula of the present invention include phenyloxy, naphthyleneoxy, diphenyloxy and the like. At least one hydrogen atom of the aryloxy group may be substituted with the same substituent as in the alkyl group described above.

The unsubstituted arylalkyl group used in the formula of the present invention means that some of the hydrogen atoms in the aryl group as defined above are substituted with lower alkyl groups such as methyl, ethyl, propyl and the like. For example benzyl, phenylethyl and the like. At least one hydrogen atom of the arylalkyl group may be substituted with the same substituent as in the alkyl group described above.

The unsubstituted heteroaryl group used in the present invention includes 1, 2 or 3 heteroatoms selected from N, O, P or S, and the remaining ring atoms are C 6-70 monovalent monocyclic or By bicyclic aromatic divalent organic compound is meant. Examples of heteroaryl groups include thienyl, pyridyl, furyl and the like. At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group described above.                     

The unsubstituted heteroaryloxy group used in the present invention means that oxygen is bonded to the heteroaryl group as defined above. For example benzyloxy, phenylethyloxy and the like. At least one hydrogen atom of the heteroaryloxy group may be substituted with the same substituent as in the alkyl group described above.

Examples of the unsubstituted arylalkyloxy group used in the present invention include a benzyloxy group and the like, and at least one hydrogen atom of the aralkyloxy group may be substituted with the same substituent as in the alkyl group described above.

The unsubstituted heteroarylalkyl group used in the present invention means that a part of the hydrogen atoms of the heteroaryl group is substituted with an alkyl group. At least one hydrogen atom of the heteroarylalkyl group may be substituted with the same substituent as in the alkyl group described above.

Examples of the unsubstituted cycloalkyl group used in the present invention include a cyclohexyl group, a cyclopentyl group, and the like, and at least one hydrogen atom of the cycloalkyl group may be substituted with the same substituent as in the alkyl group described above.

Specific examples of the unsubstituted C1-C30 alkylcarbonyl group used in the chemical formula of the present invention include acetyl, ethylcarbonyl, isopropylcarbonyl, phenylcarbonyl, naphthalenecarbonyl, diphenylcarbonyl, cyclohexylcarbonyl and the like. And at least one hydrogen atom of these alkylcarbonyl groups can be substituted with the same substituent as in the alkyl group described above.

Specific examples of the unsubstituted C7-C30 arylcarbonyl group used in the chemical formula of the present invention include phenylcarbonyl, naphthalenecarbonyl, diphenylcarbonyl, and the like, and at least one hydrogen atom of these arylcarbonyl groups is described above. It can be substituted by the same substituent as in the case of one alkyl group.

Hereinafter, a method of manufacturing an organic EL device according to the present invention will be described.

1 is a cross-sectional view showing the structure of the present invention and a general organic electroluminescent device. First, an anode electrode is formed by coating a material for the anode electrode, which is the first electrode, on the substrate. As the substrate, a substrate used in a conventional organic EL device is used, but an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, transparent and conductive indium tin oxide (ITO), tin oxide (SnO 2), and zinc oxide (ZnO) are used as the anode electrode material.

The hole injection layer material is vacuumed or spin coated on the anode electrode. The hole injection layer material is not particularly limited, and copper phthalocyanine (CuPc) or IDE406 (Idemitsu Co., Ltd.) may be used as the hole injection layer. The hole transport layer material is vacuum deposited or spin coated to form the hole transport layer. The hole transport layer material is not particularly limited, and N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine, N, N'-di (naphthalene-1-yl) -N, N'-diphenyl-benxidine: α-NPD) Etc. are used.

Subsequently, a light emitting layer is formed on the hole transport layer, and as the light emitting layer forming material, a metal compound of the formula (1), particularly an iridium compound of the formula (4), may be used alone. Alternatively, the iridium compound represented by Chemical Formula 4 of the present invention may be commonly deposited as a CBP or a dopant when the emission layer is formed. Herein, the doping concentration of the dopant is not particularly limited, but is 3 to 30 parts by weight based on 100 parts by weight of the total weight of the host and the dopant. If the content of the compound of Formula 1, which is a dopant, is less than 3 parts by weight, the additive effect is insignificant, and if it is more than 30 parts by weight, the light emitting material properties are lowered, which is not preferable.

In addition, an electron transporting layer on the light emitting layer forms a thin film as a vacuum deposition method or a spin coating method. Alq3 can be used as a hole transport layer material. In addition, a hole injection layer may be laminated on the hole transport layer, which does not particularly limit the material. As the electron injection layer, materials such as LiF, NaCl, CsF and the like can be used.

Then, the organic EL element is completed by vacuum depositing a cathode forming metal, which is a second electrode, on the hole injection layer to form a cathode. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) and the like are used. In the organic electroluminescent device of the present invention, one or two intermediate layers may be further formed on the anode electrode, the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron injection layer, and the cathode electrode as necessary.

Hereinafter, a preferred embodiment of the present invention. However, the present invention is not limited to the following examples.

Reagents Used

IrCl ₃ is 3-fluorobenzaldehyde, phenylhydrazine, oxalyl chloride, AlCl 3, NaOH, Ir (acac) ₃ acetylacetone (acacH), K ₂ CO ₃ , 2-ethoxyethane was used as the product of Aldrich. Methylene chloride, hexane, and magnesium sulfate used the product of Duksan Chemical as it was, and 3-phenyl-cinonoline used the product of Maybridge.

General method

All new compounds were identified by ¹ H-NMR, ¹³ C-NMR, UV and spectrofluorometers. ¹ H-NMR and ¹³ C-NMR were recorded using a Bruker AM-300 spectrometer, UV was used for BECKMAN DU-650 and spectrofluorometer was used for JASCO FP-750. All chemical mobility was reported in ppm based on the solvent.

Scheme 1

[반응식 2]

Scheme 2

                     [Formula 8]

Scheme 3

                                                         [Formula 13]

Synthesis Example 1 Preparation of Compound A-5

12.4 g (100 mmol) of 3-fluorobenzaldehyde was added to 250 mL of ethanol, and 10.8 g (100 mmol) of phenyl hydrazine and 57 mL of acetic acid were added thereto. Stir overnight at room temperature.

The resulting solid was filtered while neutralizing with saturated aqueous NaHCO ₃ solution in an ice bath (Ice bath) to recrystallize methylene chloride to give 16 g of Compound A-1. (Yield 75%)

While stirring 19 g (150 mmol) of oxalyl chloride, a solution of 16 g (75 mmol) of Compound A-1 in 400 mL of ether was added thereto. After heating the mixture for 3 hours, the solvent was removed and compound A-2 was obtained in the form of the crude product.

49 g (367 mmol) of aluminum chloride was added to 250 mL of chloroform, and Compound A-2 was added dropwise by dissolving in 400 mL of chloroform while maintaining 0-5 ° C. Subsequently, the reaction mixture was stirred at room temperature for 15 minutes, refluxed for 30 minutes, and water and ice were added at 10 ° C. or lower, and the solid obtained by stirring was dissolved in chloroform and washed with water. The solvent was removed from the resultant, and the obtained solid was recrystallized with ethanol to obtain 8.8 g of Compound A-3 (yield 43%).

8.7 g (32.43 mmol) of Compound A-3 and 35 g of NaOH were added to 180 mL of water, and the mixture was heated and completely dissolved. A pH of 5 was adjusted using 6 N HCl aqueous solution to produce a solid, which was filtered and recrystallized from ethanol to give 5.22 g of A-4 (yield 60%).

3.31 g (13.1 mmol) of Compound A-4 and 2.98 g (16.35 mmol) of benzophenone were heated at 200 degrees for 1.5 hours. The reaction mixture was cooled to room temperature, dissolved in ether, extracted with 6 N HCl aqueous solution, neutralized the extracted solution, and the resulting solid was filtered to give silica gel column with ethyl acetate and n-hexane mixed solvent. Purification using chromatography. 1.56 g of Compound A-5 was obtained (yield 53%).                     

¹ H-NMR (CDCl ₃ , 300 MHz): δ 8.59 (d, 1H), 8.19 (s, 1H), 8.044 (s, 1H), 8.030 (d, 1H), 7.757-7.922 (m, 3H), 7.540 (q, 1H)

Synthesis Example 2 Preparation of Compound of Formula 8

After stirring for 30 minutes while injecting nitrogen into glycerol (100 mL) at room temperature, Ir (acac) 3 and Chemical Formula A (6eq) were added thereto, and the mixture was heated and stirred at 180 to 200 degrees for 24 hours.

After the reaction was completed, water was added, and the crude product was filtered using a glass filter, and then washed with hexane. The resultant was then dissolved in methylene chloride and then purified by flash column chromatography.

Subsequently, the purified product was dissolved in methylene chloride, purified through a flash column, and then dried for 3 hours to obtain a compound of formula 8 (yield: 10%).

¹ H-NMR (CDCl ₃ , 300 MHz): δ 6.608-6.714 (m, 3H), 6.912-7.020 (m, 3H), 7.118-7.197 (m, 3H), 7.367 (s, 3H), 7.454 (t, 3H, J = 6.9Hz), 7.587 ~ 7.653 (m, 3H), 7.828 (d, 3H, J = 8.4Hz), 8.284 (d, 3H, J = 8.5Hz)

Synthesis Example 3 Preparation of Compound of Formula 13

Nitrogen was injected into 2-ethoxyethanol (100 ml) at room temperature, stirred for 30 minutes, and then compound A-5 and iridium chloride hydrate (10 mmol) were added thereto, and the mixture was heated under nitrogen at 200 ° C. for 7 hours to obtain an Ir dimer complex.                     

After stirring for 30 minutes while injecting nitrogen into 2-ethoxyethanol (100 ml) at room temperature, Ir dimer complex (5 mmol) and acetylacetonate (10 mmol) obtained according to the above procedure were added thereto, and 3N Na ₂ CO ₃ (2.5) was used as a base. ml) was added.

The reaction mixture was stirred with heating under nitrogen for 24 hours and then the reaction was confirmed to be complete by TLC. The reaction mixture was distilled under high vacuum to remove about 1/2 of the solvent, and then the resultant was filtered. Then, the resultant was filtered and subjected to a fresh column under methylene chloride / methanol conditions. It dried and obtained the compound of Formula 13. (Yield 20%)

¹ H-NMR (CDCl ₃ , 300 MHz): δ 1.842 (s, 6H), 5.156 (s, 1H), 6.100 (t, 1H, J = 7.5 Hz), 6.319-6.361 (1 m, 1H), 6.500 (t , 1H, J = 7Hz), 6.861 ~ 6.902 (m, 1H), 7.572 (d, 2H, J = 8Hz), 7.705 ~ 7.812 (m, 4H), 7.928 (s, 1H), 7.948 (s, 1H) , 8.341-8.381 (m, 4H)

Synthesis Example 4 Preparation of Compound of Formula 26

The compound of Chemical Formula 26 was obtained by synthesizing by the method of Synthesis Example 3 using 3-phenyl-shinoline ligand instead of compound A-5. (Yield 10%)

¹ H-NMR (CDCl ₃ , 300 MHz): δ 1.83 s 6H, 5.12 s 1H, 6.16 d 2H (J = 8), 6.64 t 2H (J = 6), 6.84 t 2H (J = 6), 7.70 m 10H , 8.36 m 4H

The ultraviolet absorption and the PL (photoluminescence) spectrum of the chloroform solution of the material represented by Chemical Formula 8 prepared according to the synthesis example were shown in FIG. 2. From this, it was found that the material of Formula 8 showed red emission of 628 nm.

EL measurement luminance versus lifetime data of the organic electroluminescent compound represented by Chemical Formula 13 are shown in FIG. 3.

Referring to FIG. 3, it was found that only about 12% of the overall luminance was decreased by 800 hours.

The voltage change according to the current in the EL measurement of the organic electroluminescent compound represented by Chemical Formula 13 obtained by the above process is shown in FIG. 4.

Ultraviolet absorption and PL (photoluminescence) spectra in the chloroform solution of the material represented by Chemical Formula 13 prepared according to the synthesis example were shown in FIG. 5. From this, it was found that the material of Formula 13 showed red emission of about 654 nm.

Example 1 Fabrication of Organic Electroluminescent Device

The anode used a 10 kW / cm 2 ITO substrate of Corning Corporation, and vacuum injection of IDE406 on the substrate to form a hole injection layer of 600 kW thick. Subsequently, the TPD on the hole injection layer The compound was vacuum deposited to a thickness of 300 kPa to form a hole transport layer. After forming the hole transport layer, 98 parts by weight of the compound of Formula 13 was doped into 12 parts by weight of the host material CBP on the hole transport layer to form a light emitting layer having a thickness of 200 kPa. It was.

Thereafter, BCP was vacuum-deposited on the emission layer to form an HBL layer having a thickness of 50 μs. Subsequently, Alq 3 was vacuum deposited on the emission layer to form an electron transport layer having a thickness of 200 kHz. An organic electroluminescent device was manufactured by sequentially depositing LiF 10kPa and Al 3000kPa on the electron transport layer to form a LiF / Al electrode.

In the organic electroluminescent device manufactured according to Example 1, efficiency, driving voltage, brightness, color purity, and lifetime characteristics were investigated.

The device showed a good red characteristic with efficiency of 1.3cd / A and color purity of (0.61, 0.38) at a driving voltage of 5.5V.

When the metal compound having the bidentate ligand represented by the general formula (1) of the present invention, particularly the iridium metal compound represented by the general formula (4), is applied to the organic electroluminescent device, it has excellent luminous efficiency, brightness, color purity, and lifetime characteristics, thereby improving device characteristics with high efficiency. You can get it.

Although described above with reference to the preferred embodiment of the present invention, those skilled in the art will be able to variously modify and change the present invention without departing from the spirit and scope of the invention described in the claims below. It will be appreciated.

Claims (12)

A metal compound which is a compound represented by the following formula (6): [Formula 6]

Wherein R 'and R ₅ are independently of each other hydrogen or an alkyl group of C1-C5, R "is a halogen atom, X is selected from the group represented by the following formula (5), [Chemical Formula 5]

Wherein m is 3 and n is 0, 1 or 2. delete delete delete delete delete delete delete The compound of claim 1, wherein the compound is A metal compound characterized by the following formula (8A), (13A), (14A), (19A), (20A) or (23A).

[Formula 8A] [Formula 13A] [Formula 14A]

[Formula 19A] [Formula 20A]

[Formula 23A] Wherein R is hydrogen. The compound of claim 1, wherein the compound is A metal compound represented by the following Formula 8, Formula 13, Formula 14, Formula 19, Formula 20, or Formula 23.

[Formula 8] [Formula 13] [Formula 14]

 [Formula 19] [Formula 20]

 (23) The compound of claim 1, wherein the compound is A metal compound represented by the following formula (8) or (13).

[Formula 8] [Formula 13] In an organic electroluminescent element comprising an organic film provided between a pair of electrodes, The organic electroluminescent device according to claim 1, wherein the organic film contains the metal compound of claim 1, 9, 10 or 11.

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