KR20110120074A - Organic metal compounds and organic light emitting diodes comprising the same - Google Patents

Abstract

PURPOSE: An organic metal compound is provided to ensure high quantum efficiency and phosphorescent light emitting efficiency compared with existing iridium complexing agent and to obtain an organic electroluminescent device with excellent efficiency and stability. CONSTITUTION: An organic metal compound is represented by chemical formula 1. In chemical formula 1, Ar1 and Ar3 are respectively a substituted or unsubstituted C6-40 aryl or C3-40 heteroaryl; Ar2 is a substituted or unsubstituted C3-40 heteroaryl; R is selected from the group consisting of hydrogen, deuterium, cyano, hydroxyl, nitro, substituted or unsubstituted C1-40 alkyl, substituted or unsubstituted C1-40 alkoxy, substituted or unsubstituted C1-40 alkylamino, substituted or unsubstituted C6-40 arylamino, substituted or unsubstituted C3-40 heteroarylamino, substituted or unsubstituted C1-40 alkylsilyl, substituted or unsubstituted C6-40 aryl, substituted or unsubstituted C3-40 aryloxy, substituted or unsubstituted C3-40 heteroaryl, germanium, phosphorous, and boron; L is a single bond or substituted or unsubstituted C1-4 alkylene; and n is an integer of 0-3.

Description

An organometallic compound and an organic light emitting device comprising the same. {Organic metal compounds and organic light emitting diodes comprising the same}

The present invention relates to an organic metal compound and an organic electroluminescent device comprising the same, and more particularly, to an organic metal compound having a high quantum efficiency and an organic electroluminescent device comprising the same.

Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has a merit of being lighter than a conventional cathode ray tube (CRT). The disadvantage is that the angle is limited and the back light is necessary. In contrast, organic light emitting diodes (OLEDs), which are new flat panel display devices, are displays using self-luminous phenomena, which have a large viewing angle, are thinner and shorter than liquid crystal displays, and have fast response speed In recent years, the application to full-color display or lighting is expected.

An organic light emitting display device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such organic light emitting diodes are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.

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 shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order for the organic electroluminescent device to fully exhibit the above-mentioned excellent features, the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. is supported by a stable and efficient material Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Therefore, the development of new materials in the art continues to be required.

Looking at the light emission principle in the light emitting material, electrons and holes injected from both electrodes form an exciton (exciton) by a combination, where singlet excitons are involved in fluorescence and triplet excitons are involved in phosphorescence. Phosphorescent materials using triplet excitons having a 75% generation probability show superior luminous efficiency than fluorescent materials using singlet excitons with a 25% generation probability.

High efficiency phosphors that can be applied to organic electroluminescent devices are very limited. Molecular structures that can easily emit phosphorescence are metal complexes containing a large atomic number of metals with easy molecular transitions. These include Ir, Pt, Eu, and Tb. The development of phosphors using transition metals such as, Re, Rh, Os, etc. is progressing, and luminescence properties are determined according to the type of ligand.

However, since the luminance is low and the stability of the material is low, there is a limit to apply it to an actual device, and research on new light emitting materials is being actively conducted. Among these, the iridium complex compound is attracting attention as a material having excellent phosphorescence efficiency.

The first technical problem to be solved by the present invention is to provide an organometallic compound having excellent external quantum efficiency.

The second technical problem to be solved by the present invention is to provide an organic light emitting device comprising the organometallic compound.

In order to achieve the first technical problem, the present invention provides an organometallic compound represented by the following [Formula 1].

[Formula 1]

In [Formula 1],

Ar ₁ And Ar ₃ are each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,

Ar ₂ is a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms containing at least one nitrogen atom,

R is 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, a substituted or unsubstituted carbon atom 1 to 40 alkylamino groups, substituted or unsubstituted arylamino groups having 6 to 40 carbon atoms, substituted or unsubstituted heteroarylamino groups having 3 to 40 carbon atoms, substituted or unsubstituted alkylsilyl groups having 1 to 40 carbon atoms, substituted or Unsubstituted C6-C40 arylsilyl group, substituted or unsubstituted C6-C40 aryl group, substituted or unsubstituted C3-C40 aryloxy group, substituted or unsubstituted C3-C40 hetero An aryl group, a germanium group, phosphorus and boron;

L is a single bond or a substituted or unsubstituted alkylene having 1 to 4 carbon atoms,

n is an integer of 0-3.

According to an embodiment of the present invention, the organometallic compound of [Formula 1] provides an organometallic compound, characterized in that any one selected from the group represented by the following [Formula 2] to [Formula 6].

[Formula 2] [Formula 3] [Formula 4]

[Formula 5] [Formula 6]

X, Y, Z and R are the same as the definition of R in [Formula 1],

L is a single bond or a substituted or unsubstituted alkylene having 1 to 4 carbon atoms,

o, p and q are each independently integers of 0 to 4,

n is an integer of 0-3.

In order to solve the second technical problem, the present invention is an anode; Cathode; And it is interposed between the anode and the cathode, and provides an organic electroluminescent device having a layer comprising an organometallic compound represented by the above [Formula 1].

1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.
<Description of the symbols for the main parts of the drawings>
10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode

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

The organometallic compound according to the present invention has improved phosphorescence emission efficiency than the conventional iridium complex compound, and is characterized in that various kinds of ligands are bound to the iridium complex as shown in [Formula 1]. It is characterized in that any one of the compounds represented by the above [Formula 2] to [Formula 6].

In the organometallic compound according to the present invention, the substituents of [Formula 1] to [Formula 6] are described in more detail as follows.

Adjacent functional groups in [Formula 1] may be bonded to each other to form a condensed ring of aliphatic, aromatic, heteroaliphatic or heteroaromatic which is a saturated or unsaturated ring and may be attached or fused together in a pendant method.

Substituents in [Formula 1] are each independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxyl group, a nitro group, an alkyl group of 1 to 40 carbon atoms, an alkoxy group of 1 to 40 carbon atoms, an alkylamino group of 1 to 40 carbon atoms , Arylamino group having 6 to 40 carbon atoms, heteroarylamino group having 3 to 40 carbon atoms, alkylsilyl group having 1 to 40 carbon atoms, arylsilyl group having 6 to 40 carbon atoms, aryl group having 6 to 40 carbon atoms, aryl having 3 to 40 carbon atoms It may be substituted by one or more substituents selected from the group consisting of oxy group, heteroaryl group having 3 to 40 carbon atoms, germanium group, phosphorus and boron, and may be further substituted by the substituent. The substituents may be bonded to each other to form a condensed ring of aliphatic, aromatic, heteroaliphatic or heteroaromatic which is a saturated or unsaturated ring and may be attached or fused together in a pendant manner.

Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, A stearyl group, a trichloromethyl group, a trifluoromethyl group, and the like, and at least one hydrogen atom of the alkyl group may be a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, or a silyl group (in this case, Alkylsilyl group ”), a substituted or unsubstituted amino group (—NH ₂ , —NH (R), — N (R ′) (R ″), wherein R, R ′ and R ″ are each independently carbon atoms An alkyl group of 1 to 24 (in this case referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group of 1 to 24 carbon atoms, a halogenated alkyl group of 1 to 24 carbon atoms , Alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, carbon It may be substituted with a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 5 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 3 to 24 carbon atoms, or a heteroarylalkyl group having 3 to 24 carbon atoms.

Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group and the like. These can be mentioned and can substitute by the same substituent as the case of the said 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 which is a substituent used in the compound of the present invention are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-ratio Phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group And an aromatic group such as an anthryl group, a phenanthryl group, a pyrenyl group, a fluorenyl group, a tetrahydronaphthyl group, and the like, and may be substituted with the same substituent as in the alkyl group.

Specific examples of the heteroaryl group which is a substituent used in the compound of the present invention include pyridinyl group, pyrimidinyl group, triazinyl group, indolinyl group, quinolinyl group, pyrrolidinyl group, piperidinyl group, morpholidinyl group, pipepe Radiinyl, carbazolyl, oxazolyl, oxdiazolyl, benzooxazolyl, chiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, imidazolyl and benzoimidazole At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group.

In the present invention, the term "substituted or unsubstituted" is deuterium, halogen, alkyl, alkenyl, alkoxy, aryl, arylalkyl, arylalkenyl, heteroaryl, carbazolyl, fluorenyl, Substituted or unsubstituted with one or more substituents selected from the group consisting of a nitrile group and an acetylene group.

In the organometallic compound according to the present invention, in [Formula 1]

More specifically, it may be any one of compounds represented by the following structural formulas [LS 1] to [LS 32].

[LS 1] [LS 2] [LS 3] [LS 4] [LS 5] [LS 6]

[LS 7] [LS 8] [LS 9] [LS 10] [LS 11] [LS 12] [LS 13]

[LS 14] [LS 15] [LS 16] [LS 17] [LS 18] [LS 19] [LS 20]

[LS 21] [LS 22] [LS 23] [LS 24] [LS 25] [LS 26] [LS 27]

[LS 28] [LS 29] [LS 30] [LS 31] [LS 32]

는 하기 구조식 [LS 33] 내지 [LS 42]로 표시되는 화합물 중 어느 하나일 수 있다.In the organometallic compound according to the present invention, in [Formula 1]

May be any one of compounds represented by the following structural formulas [LS 33] to [LS 42].

[LS 33] [LS 34] [LS 35] [LS 36] [LS 37]

[LS 38] [LS 39] [LS 40] [LS 41] [LS 42]

In the organometallic compound according to the present invention, [Formula 1] may be any one of the compounds represented by the following [Formula 7] to [Formula 214].

[Formula 7] [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] [Formula 28] [Formula 29] [Formula 30]

[Formula 31] [Formula 32] [Formula 33] [Formula 34]

[Formula 35] [Formula 36] [Formula 37] [Formula 38]

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

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

[Formula 47] [Formula 48] [Formula 49] [Formula 50]

[Formula 51] [Formula 52] [Formula 53] [Formula 54]

[Formula 55] [Formula 56] [Formula 57] [Formula 58]

[Formula 59] [Formula 60] [Formula 61] [Formula 62]

[Formula 63] [Formula 64] [Formula 65] [Formula 66]

[Formula 67] [Formula 68] [Formula 69] [Formula 70]

[Formula 71] [Formula 72] [Formula 73] [Formula 74]

[Formula 75] [Formula 76] [Formula 77] [Formula 78]

[Formula 79] [Formula 80] [Formula 81] [Formula 82]

[Formula 83] [Formula 84] [Formula 85] [Formula 86]

[Formula 87] [Formula 88] [Formula 89] [Formula 90]

[Formula 91] [Formula 92] [Formula 93] [Formula 94]

[Formula 95] [Formula 96] [Formula 97] [Formula 98]

[Formula 99] [Formula 100] [Formula 101] [Formula 102]

[Formula 103] [Formula 104] [Formula 105] [Formula 106]

[Formula 107] [Formula 108] [Formula 109] [Formula 110]

[Formula 111] [Formula 112] [Formula 113] [Formula 114]

[Formula 115] [Formula 116] [Formula 117] [Formula 118]

[Formula 119] [Formula 120] [Formula 121] [Formula 122]

[Formula 123] [Formula 124] [Formula 125] [Formula 126]

[Formula 127] [Formula 128] [Formula 129] [Formula 130]

[Formula 131] [Formula 132] [Formula 133] [Formula 134]

[Formula 135] [Formula 136] [Formula 137] [Formula 138]

[Formula 139] [Formula 140] [Formula 141] [Formula 142]

[Formula 143] [Formula 144] [Formula 145] [Formula 146]

[Formula 147] [Formula 148] [Formula 149] [Formula 150]

[Formula 151] [Formula 152] [Formula 153] [Formula 154]

[Formula 155] [Formula 156] [Formula 157] [Formula 158]

[Formula 159] [Formula 160] [Formula 161] [Formula 162]

[Formula 163] [Formula 164] [Formula 165] [Formula 166]

[Formula 167] [Formula 168] [Formula 169] [Formula 170]

[Formula 171] [Formula 172] [Formula 173] [Formula 174]

[Formula 175] [Formula 176] [Formula 177] [Formula 178]

[Formula 179] [Formula 180] [Formula 181] [Formula 182]

[Formula 183] [Formula 184] [Formula 185] [Formula 186]

[Formula 187] [Formula 188] [Formula 189] [Formula 190]

[Formula 191] [Formula 192] [Formula 193] [Formula 194]

[Formula 195] [Formula 196] [Formula 197] [Formula 198]

[Formula 199] [Formula 200] [Formula 201] [Formula 202]

[Formula 203] [Formula 204] [Formula 205] [Formula 206]

[Formula 207] [Formula 208] [Formula 209] [Formula 210]

[Formula 211] [Formula 212] [Formula 213] [Formula 214]

The preparation method of the organometallic compound according to the present invention is shown in detail in the following Examples.

In addition, the present invention is an anode; Cathode; And it is interposed between the anode and the cathode, and provides an organic light emitting device having a layer comprising an organometallic compound represented by the above [Formula 1].

In this case, the layer containing the organometallic compound is preferably a light emitting layer between the anode and the cathode, and the hole injection layer, the hole transport layer, the electron blocking layer, the hole blocking layer, the electron transport layer and the electron injection layer between the anode and the cathode It may further include one or more layers selected from the group consisting of.

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be additionally stacked between the cathode and the organic light emitting layer. The silver is stacked to facilitate the injection of holes from the anode, and the electron transport molecule having a small ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative mainly based on triphenylamine is used. It is used a lot.

The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1 , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD) and the like can be used.

A hole injection layer (HIL) may be further stacked on the lower portion of the hole transport layer. The hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. TCP (4,4,4 ''-tri (N-carbazolyl) triphenyl-amine), for example copper phthalocyanine (CuPc) or starburst amines, m-MTDATA (4,4 ', 4' '-tris -(3-methylphenylphenyl amino) triphenylamine) may be used.

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention has the opportunity to recombine in the light emitting layer by smoothly transporting the electrons supplied from the cathode to the organic light emitting layer and suppressing the movement of holes not bonded in the organic light emitting layer. Serves to increase. The electron transport layer material may be used without particular limitation as long as it is commonly used in the art, and for example, oxadiazole derivatives such as PBD, BMD, BND or Alq ₃ may be used.

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

The organic light emitting display device according to the present invention can be used for a display device, a display device and a monochrome or white lighting device.

1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and if necessary, the hole injection layer 30 and The electron injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to Figure 1 with respect to the organic light emitting device and a method of manufacturing the present invention are as follows. First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the anode electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30.

Subsequently, the organic light emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method. can do. The hole blocking layer prevents such a problem by using a material having a very low highest Occupied Molecular Orbital (HOMO) level because when the hole is introduced into the cathode through the organic light emitting layer is reduced the lifetime and efficiency of the device. . In this case, the hole blocking material to be used is not particularly limited, but should have an ionization potential higher than the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a cathode forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form a cathode 80 electrode. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

According to another embodiment of the present invention, at least one layer selected from 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 a single molecule deposition method or a solution process The organic light emitting display device according to the present invention may be used in display devices, display devices, and monochrome or white lighting devices.

Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to illustrate the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.

Synthesis Example 1 Preparation of Compound Represented by Formula 7

(1) Synthesis of Compound Represented by [Formula 1-a]

The compound represented by [Formula 1-a] was synthesized by the following [Scheme 1].

Scheme 1

                      [Formula 1-a]

Benzyl bromide 50.0g (0.292mol) and diethyl ether (500ml) were added to a 1L round bottom flask, and then 65.8g (1.462mol) of 50wt% dimethylamine was added slowly and stirred at room temperature for 12 hours. The organic layer was separated, extracted with 10 wt% citric acid, and the aqueous layer was neutralized with 15 wt% sodium hydroxide solution. The neutralized aqueous layer was extracted with diethyl ether, dried, and solvent removed to synthesize [Formula 1-a]. (Yield 35.1 g 89%)

(2) Synthesis of Compound Represented by [Formula 1-b]

The compound represented by [Formula 1-b] was synthesized by the following [Scheme 2].

Scheme 2

                                         [Formula 1-b]

In a 500 ml round bottom flask, 36.0 g (0.19 mol) of bromodifluorobenzene, 82.4 g (0.22 mol) of 2-tributylstenylpyridinine, and 10.8 g (0.009 mol) of Pd (PPh ₃ ) ₄ were dissolved in toluene (360 ml). After refluxing at 120 ℃ for 18 hours. After the solvent was removed, hexane and ethyl acetate were used as developing solvents, and the resultant was separated by column chromatography to obtain a compound represented by [Formula 1-b]. (Yield 28 g 79%)

(3) Synthesis of Compound Represented by [Formula 1-c]

The compound represented by [Formula 1-c] was synthesized by the following [Scheme 3].

Scheme 3

                                     [Formula 1-c]

In a 250 ml round bottom flask, 20.0 g (0.105 mol) of [Formula 1-b] obtained from [Scheme 2], IrCl ₃ .xH ₂ O 12.5 g (0.042 mol), ethoxyethanol (210 ml), and water (70 ml) After adding the mixed solution, the mixture was refluxed at 120 ° C. for 18 hours. The temperature was lowered to room temperature, poured into water (1 L), and the resulting solid was filtered and washed with water, methanol, diethyl ether, and hexane to prepare [Formula 1-c]. (Yield 18.8 g 74%)

(4) Synthesis of Compound Represented by Formula 7

The compound represented by [Formula 7] was synthesized by the following [Scheme 4].

Scheme 4

                                      [Formula 7]

15.0 g (0.012 mol) of [Formula 1-c] obtained from [Scheme 3] and THF (150 ml) were put in a 250 ml round bottom flask under nitrogen stream, and 15.2 g (0.037 mol) of normal butyllithium was slowly added at -78 ° C. Add and stir for 1 hour. 4.5 g (0.031 mol) of [Formula 1-a] obtained from [Scheme 1] at the same temperature was added thereto, and the resultant was stirred at room temperature for 18 hours. The organic layer was separated using an aqueous ammonium chloride solution and dichloromethane, dried and concentrated under reduced pressure, and then a compound represented by [Chemical Formula 7] was synthesized using column chromatography with dichloromethane and a hexane developing solvent. (Yield 18.8 g 74%)

MS (MALDI-TOF): m / z 707 [M] &lt; + &gt;; Anal. Calcd.

C ₃₁ H ₂₄ F ₄ IrN ₃ : C, 52.68; H, 3.42; N, 5.95.Found: C, 51.82; H, 3.35; N, 6.01.

Synthesis Example 2 Preparation of Compound Represented by Formula 10

(1) Synthesis of Compound Represented by [Formula 2-a]

The compound represented by [Formula 2-a] was synthesized by the following [Scheme 5].

Scheme 5

                   [Formula 2-a]

[Formula 2-a] was synthesized through the same procedure as the synthesis of [Formula 1-a] of [Scheme 1]. (Yield 14.4 g 85.1%)

(2) Synthesis of Compound Represented by Formula 10

The compound represented by [Formula 10] was synthesized by the following [Scheme 6].

Scheme 6

                                       [Formula 10]

With the compound represented by [Formula 1-c] obtained from [Scheme 3] and [Formula 2-a] obtained from [Scheme 5] through the same procedure as the synthesis of [Scheme 7] of [Scheme 4] A compound represented by the formula [10] was synthesized. (Yield 14.4 g 85.1%)

MS (MALDI-TOF): m / z 775 [M] &lt; + &gt;; Anal. Calcd.

C ₃₂ H ₂₃ F ₇ IrN ₃ : C, 49.61; H, 2.99; N, 5.42.Found: C, 49.11; H, 2.91; N, 5.49.

Synthesis Example 3 Preparation of Compound Represented by Formula 17

(1) Synthesis of Compound Represented by [Formula 3-a]

The compound represented by [Formula 3-a] was synthesized by the following [Scheme 7].

Scheme 7

                    [Formula 3-a]

[Formula 3-a] was synthesized through the same procedure as the synthesis of [Formula 1-a] of [Scheme 1]. (Yield 13.6 g 83.1%)

(2) Synthesis of Compound Represented by [Formula 3-b]

The compound represented by [Formula 3-b] was synthesized by the following [Scheme 8].

Scheme 8

                            [Formula 3-b]

51.29 g (0.914 mol) of potassium hydroxide and 513 ml of N, N-dimethylformamide were added to a 1 L round bottom flask, followed by stirring at room temperature for 5 minutes. After 5 minutes, benzimidazole 27g (0.229mol) was added thereto and stirred at room temperature for 2 hours. After 2 hours, the reaction solution was lowered to 0 ° C., and 114.24 g (0.343 mol) of 4-bromobenzyl bromide was added thereto. When the reaction was completed, water was added to the reaction solution, the mixture was stirred, the layers were separated, the aqueous layer was removed, the organic layer was separated, concentrated under reduced pressure, hexane was poured into the crystals, and the crystals were dried to prepare [Formula 3-b]. (Yield 48g 73%)

(3) Synthesis of Compound Represented by [Formula 3-c]

The compound represented by [Formula 3-c] was synthesized by the following [Scheme 9].

Scheme 9

                                       [Formula 3-c]

1-bromo-2,4-difluorobenzene 100g (0.518mol) and 1L of diethyl ether were added to a 2L round bottom flask, followed by stirring at -78 ° C for 1 hour. 388.62 ml (0.622 mol) of n-butyl lithium 1.6M was slowly added dropwise. After 2 hours, 146.18 g (0.777 mol) of triisopropyl borate was slowly added dropwise and the temperature was raised to room temperature. After 2 hours the pH was adjusted to acid with 2N hydrochloric acid. Extraction was carried out, and the organic layer was collected and blown. Excess hexane was poured to obtain crystals, followed by drying. (Yield 54.8 g 67%)

(4) Synthesis of Compound Represented by [Formula 3-d]

A compound represented by [Formula 3-d] was synthesized by the following [Scheme 10].

Scheme 10

                                [Formula 3-d]

40 g (0.139 mol) of the compound represented by [Formula 3-b] obtained from the above [Scheme 8] and [Scheme 9], 26.4 g (0.167 mol) represented by [Formula 3-c], in a 2 L round bottom flask, Potassium carbonate 77.01 g (0.577 mol), tetrakistriphenylphosphinepalladium 8.06 g (0.007 mol), 200 ml of water, 400 ml of toluene and 200 ml of ethanol were added and refluxed at 80 ° C. for 24 hours. When the reaction was terminated, the resultant of the reaction was separated by layer to remove the aqueous layer, the organic layer was separated and concentrated under reduced pressure, hexane was poured to catch the crystals and dried to produce the formula [3-d]. (Yield 40 g 88.6%)

(5) Synthesis of Compound Represented by [Formula 3-e]

The compound represented by [Formula 3-e] was synthesized by the following [Scheme 11].

Scheme 11

                       [Formula 3-e]

40 g (0.125 mol) of the compound represented by [Formula 3-d] obtained from the above [Scheme 10] and 400 ml of toluene were added to a 500 ml round bottom flask, and the mixture was heated to 70 ° C. When the semi-solution became clear, 26.6 g (0.187 mol) of iodomethane was added thereto, followed by stirring for 18 hours. When the reaction was terminated, the temperature was lowered to room temperature and then filtered to obtain [Formula 3-e]. (Yield 53g 91.8%)

(6) Synthesis of Compound Represented by [Formula 3-f]

The compound represented by [Formula 3-f] was synthesized by the following [Scheme 12].

[Reaction Scheme 12]

                                [Formula 3-f]

Into a 1 L round bottom flask was added 6.1 g (0.009 mol) of [Ir (COD) Cl] ₂ , 4.8 g (0.090 mol) of methoxy sodium, and 500 ml of 2-ethoxyethanol and stirred at room temperature for 2 hours. 30 g (0.045 mol) of the compound represented by [Formula 3-e] obtained from [Scheme 11] was added to the reaction product, and the mixture was refluxed at 135 ° C. for 3 hours. After the temperature was lowered to room temperature, the solvent was removed by distillation under reduced pressure, and [Formula 3-f] was synthesized by using column chromatography with dichloromethane developing solvent. (Yield 12.5 g 55%)

(7) Synthesis of Compound Represented by Formula 17

The compound represented by [Formula 17] was synthesized by the following [Scheme 13].

Scheme 13

                                     [Formula 17]

With the compound represented by [Formula 3-a] obtained from [Scheme 7] and [Formula 3-f] obtained from [Scheme 12] through the same procedure as in the synthesis of [Scheme 7] of [Scheme 4] A compound represented by [Formula 17] was synthesized. (Yield 4.3g 62.5%)

MS (MALDI-TOF): m / z 988 [M] &lt; + &gt;; Anal. Calcd.

C ₅₀ H ₃₅ F ₄ IrN ₆ : C, 60.78; H, 3.57; N, 8.51.Found: C, 60.11; H, 3.48; N, 8.58.

Synthesis Example 4 Preparation of Compound Represented by Formula 40

(1) Synthesis of Compound Represented by [Formula 4-a]

The compound represented by [Formula 4-a] was synthesized by the following [Scheme 14].

[Reaction Scheme 14]

                                    [Formula 4-a]

15 g (0.165 mol) of tilt-butyl-4-toluene, 13.5 g (0.082 mol) of 2,2'-azobismethylpropionitrile, 32.3 g (0.181 mol) of N-bromosucinimide, benzyl bromide in a 1 L round bottom flask , Benzene (150ml) was added and refluxed for 5 hours. The reaction is cooled to 0 ° C. and then the solvent is removed by distillation under a filter and reduced pressure. [Formula 4-a] was synthesized using column chromatography with ethyl acetate and a hexane developing solvent. (Yield 25.3 g 90.3%)

(2) Synthesis of Compound Represented by [Formula 4-b]

The compound represented by [Formula 4-b] was synthesized by the following [Scheme 15].

[Reaction Scheme 15]

                     [Formula 4-b]

[Formula 4-b] was synthesized by the same procedure as the synthesis of [Scheme 1-a] of [Scheme 1] with the compound represented by [Scheme 4-a] obtained from [Scheme 14]. (Yield 14.1 g 89.5%)

(3) Synthesis of Compound Represented by [Formula 4-c]

The compound represented by [Formula 4-c] was synthesized according to Reaction Scheme 16 below.

[Reaction Scheme 16]

                         [Formula 4-c]

24.0 g (0.20 mol) of difluoropyridine and 240 ml of tetrahydrofuran were put into a 500 ml round bottom flask, and it cooled to minus 78 degreeC. 88.2 g (0.22 mol) of LDA was slowly added dropwise to this solution, stirred for 2 hours at the same temperature, and then 63.5 g (0.25 mol) of iodine was added slowly. The reaction product was warmed up to room temperature, and then stirred for 12 hours. Water (2L) was added to the reaction product, followed by stirring for 10 minutes. Extracted twice with ethyl acetate, the organic layer was removed and the solvent was removed and then recrystallized with hexane to synthesize [Formula 4-c]. (Yield 35.8 g 69%)

(4) Synthesis of Compound Represented by [Formula 4-d]

The compound represented by [Formula 4-d] was synthesized by the following [Scheme 17].

[Reaction Scheme 17]

                                    [Formula 4-d]

Magnesium 2.8 g (0.18 mol) and tetrahydrofuran (50 ml) were placed in a 500 ml round bottom flask, and 30.0 g (0.124 mol) of the compound represented by [Formula 4-c] obtained from [Scheme 16] was added to tetrahydrofuran. (240ml) and slowly added dropwise to reflux for 1 hour. After the temperature was lowered to room temperature, 12.5 g (0.18 mol) of 2-pyridinealdehyde was added to the reaction solution in tetrahydrofuran (100 ml), followed by stirring for 10 hours. The reactant was poured into a saturated aqueous ammonium chloride solution, the organic layer was dried and concentrated under reduced pressure, and the solid obtained by column chromatography separation with an ethyl acetate developing solvent was dried to prepare a compound represented by [Formula 4-d]. (Yield 18.5 g 67%)

(5) Synthesis of Compound Represented by [Formula 4-e]

The compound represented by [Formula 4-e] was synthesized by the following [Scheme 18].

[Reaction Scheme 18]

                                       [Formula 4-e]

In a 100 ml round bottom flask, 17.0 g (0.076 mol) of the compound represented by [Formula 4-d] obtained from [Scheme 17] was dissolved in methanol (50 ml) and sulfuric acid (10 ml), followed by 10% Pd / C (2 g). Put it in. Hydrogen was added at room temperature, stirred until the hydrogen was consumed, the catalyst was filtered off, neutralized with 10% aqueous sodium hydroxide solution, extracted with dichloromethane, and concentrated under reduced pressure. The solid obtained by separation by column chromatography with an ethyl acetate developing solvent was dried to prepare a compound represented by [Formula 4-e]. (Yield 7.72 g 49%)

(6) Synthesis of Compound Represented by [Formula 4-f]

The compound represented by [Formula 4-f] was synthesized according to Reaction Scheme 19 below.

Scheme 19

                                     [Formula 4-f]

[Formula 4-f] was synthesized by the same procedure as the synthesis of [Formula 1-c] of [Scheme 3] with the compound represented by [Formula 4-e] obtained from [Scheme 18]. (Yield 14.1 g 89.5%)

(7) Synthesis of Compound Represented by Formula 40

The compound represented by [Formula 40] was synthesized by the following [Scheme 20].

[Reaction Scheme 20]

                                   [Formula 40]

With the compound represented by [Chemical Formula 4-b] obtained from [Scheme 15] and [Chemical Formula 4-f] obtained from [Scheme 19], [Synthesis 7] through the same procedure as in [Scheme 7] A compound represented by the formula [40] was synthesized. (Yield 3.1g 53%)

MS (MALDI-TOF): m / z 736 [M] &lt; + &gt;; Anal. Calcd.

C ₃₁ H ₂₅ F ₄ IrN ₅ : C, 50.60; H, 3.42; N, 9.52.Found: C, 49.99.11; H, 3.38; N, 9.51.

Synthesis Example 5 Preparation of Compound Represented by Formula 75

(1) Synthesis of Compound Represented by [Formula 5-a]

The compound represented by [Formula 5-a] was synthesized by the following [Scheme 21].

Scheme 21

                     [Formula 5-a]

[Scheme 5-a] was synthesized through the same procedure as that of [Scheme 1-a] in [Scheme 1]. (Yield 15.0 g 91.5%)

(2) Synthesis of Compound Represented by [Formula 5-b]

The compound represented by [Formula 5-b] was synthesized by the following [Scheme 22].

[Reaction Scheme 22]

                          [Formula 5-b]

In a 100 ml round bottom flask, formic acid (40 ml) was added slowly 23.4 g (0.135 mol) of 2-bromo-5-aminopyridine at 0 ° C. or lower, followed by 34 ml (0.420 mol) of formaldehyde 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 obtained by separation by column chromatography with a dichloromethane developing solvent was dried to prepare a compound represented by [Formula 5-b]. (Yield 10.4 g 40%).

(3) Synthesis of Compound Represented by [Formula 5-c]

The compound represented by [Formula 5-c] was synthesized by the following [Scheme 23].

[Reaction Scheme 23]

                            [Formula 5-c]

Into a 250 ml round bottom flask, 10.0 g (0.049 mol) of the compound represented by [Formula 5-b] obtained from [Scheme 22] and 100 ml of tetrahydrofuran were added thereto, and then 24.5 g of 1.6M normal butyllithium (0.060) at -78 ° C. mol) was slowly added dropwise and stirred for 1 hour. 4.4 g (0.060 mol) of N, N-dimethylformamide was added dropwise at the same temperature, followed by stirring at room temperature for 8 hours. The organic layer was separated using water and ethyl acetate, concentrated under reduced pressure, and separated by column chromatography using hexane and ethyl acetate as a developing solvent to obtain a compound represented by [Formula 5-c]. (Yield 5.1g 69.3%)

(4) Synthesis of Compound Represented by [Formula 5-d]

The compound represented by [Formula 5-d] was synthesized by the following [Scheme 24].

Scheme 24

                                   [Formula 5-d]

With the compound represented by [Formula 4-c] obtained from [Scheme 16] and [Formula 5-c] obtained from [Scheme 23], the same procedure as in [Synthesis 4-d] of [Scheme 17] A compound represented by [Formula 5-d] was prepared. (Yield 18.6 g 56.8%)

(5) Synthesis of Compound Represented by [Formula 5-e]

The compound represented by [Formula 5-e] was synthesized by the following [Scheme 25].

Scheme 25

                                [Formula 5-e]

A compound represented by [Formula 5-e] was prepared by the same procedure as the synthesis of [Formula 4-e] of [Scheme 18] with the compound represented by [Formula 5-d] obtained from [Scheme 24]. . (Yield 7.9 g 56.3%)

(6) Synthesis of Compound Represented by [Formula 5-f]

The compound represented by [Formula 5-f] was synthesized by the following [Scheme 26].

Scheme 26

                                   [Formula 5-f]

The compound represented by [Formula 5-f] was synthesized by the same procedure as the synthesis of [Formula 1-c] of [Scheme 3] using the compound represented by [Formula 5-e] obtained from [Scheme 25]. . (Yield 7.4 g 85.3%)

(7) Synthesis of Compound Represented by Formula 75

The compound represented by [Formula 75] was synthesized by the following [Scheme 27].

Scheme 27

                                    (75)

With the compound represented by [Formula 5-f] obtained from the [Scheme 26] and [Formula 5-a] obtained from the [Scheme 21] through the same procedure as the synthesis of [Scheme 7] of [Scheme 4] A compound represented by the formula [75] was synthesized. (Yield 1.9g 45.8%)

MS (MALDI-TOF): m / z 853 [M] &lt; + &gt;; Anal. Calcd.

C ₃₆ H ₃₈ F ₄ IrN ₇ O: C, 50.69; H, 4.49; N, 11.50.Found: C, 50.18.11; H, 4.40; N, 11.48.

Synthesis Example 6 Preparation of Compound Represented by Formula 199

(1) Synthesis of Compound Represented by [Formula 6-a]

The compound represented by [Formula 6-a] was synthesized by the following Reaction Scheme 28.

Scheme 28

                    [Formula 6-a]

[Scheme 6-a] was synthesized through the same procedure as the synthesis of [Scheme 1-a] of [Scheme 1]. (Yield 13.6 g 83.6%)

(2) Synthesis of Compound Represented by [Formula 6-b]

The compound represented by [Formula 6-b] was synthesized by the following [Scheme 29].

Scheme 29

                                   [Formula 6-b]

Into a 250 ml round bottom flask, 20.0 g (0.105 mol) of 1-bromo-2,6-fluorobenzene, 17.8 g (0.062 mol) of 1,3-dibromo-5,5-dimethylhydantoin and dichloromethane were added. After stirring, 18.7 g (0.124 mol) of trichloromethanesulfonic acid was added thereto, followed by stirring at room temperature for 5 hours. After neutralizing with an aqueous sodium carbonate solution and then removing the solvent by distillation under reduced pressure and distillation under reduced pressure, a compound represented by [Formula 6-b] was synthesized using column chromatography as a hexane developing solvent. (Yield 26.4 g 92.5%)

(3) Synthesis of Compound Represented by [Formula 6-c]

The compound represented by [Formula 6-c] was synthesized by the following [Scheme 30].

Scheme 30

                                            [Formula 6-c]

25.0 g (0.092 mol) of the compound represented by [Formula 6-b] obtained from the above [Scheme 29], 2-5.9 g (0.110 mol) of 4-methoxypyridine borate, tetrakistriphenylphosphinepalladium in a 1 L round bottom flask 2.1g (0.002mol), potassium carbonate 24.3g (0.184mol), THF (500ml) and water (250ml) was added to reflux for 12 hours. The solution was cooled to room temperature, the organic layer was separated, concentrated under reduced pressure, and the solid obtained by column chromatography using hexane and ethyl acetate as a developing solvent was dried to prepare a compound represented by [Formula 6-c]. . (Yield 20.4 g 74%)

(4) Synthesis of Compound Represented by [Formula 6-d]

The compound represented by [Formula 6-d] was synthesized by the following [Scheme 31].

Scheme 31

                                   [Formula 6-d]

In a 500 ml round bottom flask, 20.0 g (0.067 mol) of a compound represented by [Formula 6-c] obtained from the above [Scheme 30], 12.0 g (0.080 mol) of xylene boronic acid, 1.5 g of tetrakistriphenylphosphinepalladium ( 0.001 mol), potassium carbonate 17.7g (0.134mol), THF (400 ml) and water (200ml) was added to reflux for 12 hours. The solution was cooled to room temperature, the organic layer was separated, concentrated under reduced pressure, and the solid obtained by column chromatography using hexane and ethyl acetate as a developing solvent was dried to prepare a compound represented by [Formula 6-d]. . (Yield 18.5g 85.2%)

(5) Synthesis of Compound Represented by [Formula 6-e]

The compound represented by [Formula 6-e] was synthesized by the following [Scheme 32].

Scheme 32

                                         [Formula 6-e]

Using the compound represented by [Formula 6-d] obtained from [Scheme 31] through the same procedure as the synthesis of [Formula 1-c] of [Scheme 3] to synthesize the compound represented by [Formula 6-e] It was. (Yield 10.6 g 65.9%)

(6) Synthesis of Compound Represented by Formula 199

The compound represented by [Formula 199] was synthesized by the following [Scheme 33].

Scheme 33

                                        [Formula 199]

With the compound represented by [Formula 6-e] obtained from the [Scheme 32] and [Formula 6-a] obtained from the [Scheme 28] through the same procedure as the synthesis of [Scheme 7] of [Scheme 4] 199] was synthesized. (Yield 1.9g 45.8%)

MS (MALDI-TOF): m / z 1000 [M] &lt; + &gt;; Anal. Calcd.

C ₅₀ H ₄₃ F ₄ IrN ₄ O ₂ : C, 60.05; H, 4.33; N, 5.60.Found: C, 59.89; H, 4.27; N, 5.63.

Examples 1 to 6 Fabrication of Organic Electroluminescent Device

The light emitting area of the ITO glass was patterned to have a size of 2 mm x 2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), mCP + compound (10%) prepared by the present invention ( 300 Å), Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å) were formed in this order, and measured at 0.4 mA.

[DNTPD]

[NPD]

[mCP]

[Alq ₃ ]

Comparative Example 1

An organic light emitting display device for a comparative example was manufactured in the same manner except for using FIrpic as the following blue phosphorescent dopant material instead of the organometallic compound prepared by the present invention in the device structure of Examples 1 to 6.

[FIrpic]

division Host Dopant External quantum efficiency (%) Luminous color Comparative Example 1 mCP FIrpic 9.1 blue Example 1 mCP Formula 7 9.7 blue Example 2 mCP Formula 10 10.2 blue Example 3 mCP Formula 17 9.6 blue Example 4 mCP Formula 40 10.8 blue Example 5 mCP Formula 75 10.1 blue Example 6 mCP Formula 199 9.8 blue

As shown in <Examples 1 to 6>, <Comparative Example 1> and [Table 1], the organic compound obtained by the present invention exhibits excellent external quantum efficiency as compared to FIrpic, which is widely used as a phosphorescent material. It can be seen that it can be usefully used for a display device, a display device and lighting.

Claims (10)

An organometallic compound represented by the following [Formula 1]:
[Formula 1]

In [Formula 1],
Ar ₁ And Ar ₃ are each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,
Ar ₂ is a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms containing at least one nitrogen atom,
R is 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, a substituted or unsubstituted carbon atom 1 to 40 alkylamino groups, substituted or unsubstituted arylamino groups having 6 to 40 carbon atoms, substituted or unsubstituted heteroarylamino groups having 3 to 40 carbon atoms, substituted or unsubstituted alkylsilyl groups having 1 to 40 carbon atoms, substituted or Unsubstituted C6-C40 arylsilyl group, substituted or unsubstituted C6-C40 aryl group, substituted or unsubstituted C3-C40 aryloxy group, substituted or unsubstituted C3-C40 hetero An aryl group, a germanium group, phosphorus and boron;
L is a single bond or a substituted or unsubstituted alkylene having 1 to 4 carbon atoms,
n is an integer of 0-3. The method of claim 1,
The organometallic compound is an organometallic compound, characterized in that any one selected from the group represented by the following [Formula 2] to [Formula 6]:
[Formula 2] [Formula 3] [Formula 4]

[Formula 5] [Formula 6]

X, Y, Z and R are the same as the definition of R in [Formula 1],
L is a single bond or a substituted or unsubstituted alkylene having 1 to 4 carbon atoms,
o, p and q are each independently integers of 0 to 4,
n is an integer of 0-3. The method of claim 1,
remind

Is an organometallic compound, characterized in that any one selected from the group represented by [LS 1] to [LS 32]:
[LS 1] [LS 2] [LS 3] [LS 4] [LS 5] [LS 6]

[LS 7] [LS 8] [LS 9] [LS 10] [LS 11] [LS 12] [LS 13]

[LS 14] [LS 15] [LS 16] [LS 17] [LS 18] [LS 19] [LS 20]

[LS 21] [LS 22] [LS 23] [LS 24] [LS 25] [LS 26] [LS 27]

[LS 28] [LS 29] [LS 30] [LS 31] [LS 32]

The method of claim 1,
remind

Is an organometallic compound, characterized in that any one selected from the group represented by [LS 33] to [LS 42]:
[LS 33] [LS 34] [LS 35] [LS 36] [LS 37]

[LS 38] [LS 39] [LS 40] [LS 41] [LS 42]

The method of claim 1,
An organometallic compound, characterized in that any one compound selected from the group represented by the following [Formula 7] to [Formula 214]:
[Formula 7] [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] [Formula 28] [Formula 29] [Formula 30]

[Formula 31] [Formula 32] [Formula 33] [Formula 34]

[Formula 35] [Formula 36] [Formula 37] [Formula 38]

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

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

[Formula 47] [Formula 48] [Formula 49] [Formula 50]

[Formula 51] [Formula 52] [Formula 53] [Formula 54]

[Formula 55] [Formula 56] [Formula 57] [Formula 58]

[Formula 59] [Formula 60] [Formula 61] [Formula 62]

[Formula 63] [Formula 64] [Formula 65] [Formula 66]

[Formula 67] [Formula 68] [Formula 69] [Formula 70]

[Formula 71] [Formula 72] [Formula 73] [Formula 74]

[Formula 75] [Formula 76] [Formula 77] [Formula 78]

[Formula 79] [Formula 80] [Formula 81] [Formula 82]

[Formula 83] [Formula 84] [Formula 85] [Formula 86]

[Formula 87] [Formula 88] [Formula 89] [Formula 90]

[Formula 91] [Formula 92] [Formula 93] [Formula 94]

[Formula 95] [Formula 96] [Formula 97] [Formula 98]

[Formula 99] [Formula 100] [Formula 101] [Formula 102]

[Formula 103] [Formula 104] [Formula 105] [Formula 106]

[Formula 107] [Formula 108] [Formula 109] [Formula 110]

[Formula 111] [Formula 112] [Formula 113] [Formula 114]

[Formula 115] [Formula 116] [Formula 117] [Formula 118]

[Formula 119] [Formula 120] [Formula 121] [Formula 122]

[Formula 123] [Formula 124] [Formula 125] [Formula 126]

[Formula 127] [Formula 128] [Formula 129] [Formula 130]

[Formula 131] [Formula 132] [Formula 133] [Formula 134]

[Formula 135] [Formula 136] [Formula 137] [Formula 138]

[Formula 139] [Formula 140] [Formula 141] [Formula 142]

[Formula 143] [Formula 144] [Formula 145] [Formula 146]

[Formula 147] [Formula 148] [Formula 149] [Formula 150]

[Formula 151] [Formula 152] [Formula 153] [Formula 154]

[Formula 155] [Formula 156] [Formula 157] [Formula 158]

[Formula 159] [Formula 160] [Formula 161] [Formula 162]

[Formula 163] [Formula 164] [Formula 165] [Formula 166]

[Formula 167] [Formula 168] [Formula 169] [Formula 170]

[Formula 171] [Formula 172] [Formula 173] [Formula 174]

[Formula 175] [Formula 176] [Formula 177] [Formula 178]

[Formula 179] [Formula 180] [Formula 181] [Formula 182]

[Formula 183] [Formula 184] [Formula 185] [Formula 186]

[Formula 187] [Formula 188] [Formula 189] [Formula 190]

[Formula 191] [Formula 192] [Formula 193] [Formula 194]

[Formula 195] [Formula 196] [Formula 197] [Formula 198]

[Formula 199] [Formula 200] [Formula 201] [Formula 202]

[Formula 203] [Formula 204] [Formula 205] [Formula 206]

[Formula 207] [Formula 208] [Formula 209] [Formula 210]

[Formula 211] [Formula 212] [Formula 213] [Formula 214]

Anode;
Cathode; And
An organic electroluminescent device having a layer interposed between the anode and the cathode, the layer comprising the organometallic compound of any one of claims 1 to 5. The method according to claim 6,
The layer containing the organometallic compound is an organic light emitting device, characterized in that the light emitting layer between the anode and the cathode. The method of claim 7, wherein
An organic electroluminescent device further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the anode and the cathode. The method of claim 8,
At least one layer selected from 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 molecule deposition method or a solution process. The method according to claim 6,
The organic electroluminescent device is an organic electroluminescent device, characterized in that used for a display device, a display device, or a device for monochrome or white illumination.

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