KR100894135B1 - Organometallic complex compounds for organic light emitting display and display unit using thereof - Google Patents

Abstract

The present invention includes a silicon derivative ligand as a metal complex compound for an organic electroluminescent device represented by the following formula (1).

Therefore, the metal complex compound according to the present invention has a bulky ligand, thereby inhibiting intermolecular interactions, and thus has a high luminous efficiency, and injecting holes and electrons by introducing electron donors and electron pulling bodies into the ligands of the metal complex compound. It is possible to exhibit high luminescence properties by improving the transmission properties.

Description

Metal complex compounds for organic electroluminescent devices and organic light emitting display devices using the same

1 is a view showing an organic light emitting display device according to the present invention.

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

  1 organic light emitting display device 10 substrate

 20: first electrode 30: second electrode

100: organic thin film layer 110: first buffer layer

120: second buffer layer

The present invention relates to a metal complex compound for an organic light emitting device and an organic light emitting display device employing the same as a light emitting dopant, and more particularly, for an organic light emitting device that can be used as a light emitting layer forming material of an organic light emitting device. The present invention relates to a metal complex compound and an organic light emitting display device employing the same as a light emitting dopant.

Among the display devices, the organic light emitting display device (organic EL device) is a self-luminous display device capable of low voltage driving, a wide viewing angle, excellent contrast, and fast response speed. This has the advantage of being possible.

In 1987, Eastman Kodak Co., Ltd. developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987]. In 1987, C. W. Tang et al. Reported the device having practical performance for the organic electroluminescent device (Applied Physics Letters, Vol. 51, No. 12, 913-915 (1987)). The document describes a structure in which a thin film (hole transport layer) of a diamine derivative and a thin film (electron transport light emitting layer) of Alq3 (tris (8-hydroxy-quinolate) aluminum) are laminated as an organic layer.

In general, an organic EL device has a structure formed on a glass substrate in order of an anode made of a transparent electrode, an organic thin film including a light emitting region, and a metal electrode.

In this case, the organic thin film may include a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer or an electron injection layer, and may further include an electron blocking layer or a hole blocking layer due to the light emission characteristics of the light emitting layer.

When an electric field is applied to an organic EL device having such a structure, holes and electrons are injected from the anode and the cathode, respectively, and the injected holes and electrons are recombined in the light emitting layer via the respective hole transport layer and the electron transport layer to emit light excitons. To form.

The light emitting excitons formed emit light while transitioning to ground states. In this case, the light emitting layer (dopant) may be doped into the light emitting layer (host) to increase the efficiency and stability of the light emitting state.

In the organic EL device having the structure as described above, 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.

Recently, it has been known that phosphorescent light emitting materials as well as fluorescent light emitting materials can be used as light emitting materials of organic EL devices. (D. F.O'Brien et al., Applied Physics Letters, 74 (3), 442-444, 1999; M. A. Baldo et al., Applied Physics letters, 75 (1), 4-6,1999)

The phosphorescence emission is a mechanism in which electrons transfer from the ground state to the excited state, and then the singlet exciter is non-emissive to triplet excitons through intersystem crossing, and then the triplet excitons are emitted to the ground state. Is done.

At this time, the transition to the triplet excitons does not directly transition to the ground state (spin forbidden), since the process of transition to the ground state after the flipping of the electron spin (light emission time) than the fluorescence (lifetime) It has a longer characteristic.

That is, the emission duration of fluorescence emission is only several nanoseconds, but in the case of phosphorescence emission, it corresponds to several micro seconds, which is a relatively long time. In addition, in quantum mechanical terms, when the holes injected from the anode and the electrons injected from the cathode recombine to form a light-emitting excitons, the formation ratio of the singlet and triplet is 1: 3, and the triplet in the EL device is generated. Luminescent excitons are generated about three times more than singlet luminescent excitons.

Therefore, in the case of fluorescence, the probability of singlet excited state is 25% (triple state 75%) and there is a limit of luminous efficiency, whereas phosphorescence can be used to triplet 75% and singlet excited state 25%. Can be up to 100% internal quantum efficiency. Therefore, in the case of using the phosphorescent material, there is an advantage that can achieve a light emission efficiency about three times higher than the fluorescent light emitting material.

As a molecular structure that is easy to phosphorescence emission, it is a molecular structure that is easy to intercalate and introduces heavy metals such as Ir, Pt, Rh, and Pd into organic molecules. In this case, spin generated by heavy atom effect Spin-orbital coupling results in a mixture of triplet and singlet states, which allows forbidden transitions and effectively phosphorescent at room temperature.

Among these, the iridium organometallic complex has attracted attention as a material having excellent phosphorescence efficiency and phosphorescent materials using the same have been reported [Sergey Lamansky etc. Inorg. Chem., 40, 1704-1711, 2001 & J. Am. Chem. Soc. , 123, 4304-4312, 2001].

The phosphorescent organic metal complex has been mainly focused on the development of low-molecular materials that can form devices by vacuum evaporation, and in the case of polymer materials, the device is a wet process such as spin coating, inkjet printing, or casting. Can be configured.

The wet process using the polymer is easier to fabricate the device than the vacuum deposition method and has more advantages in terms of cost and size, but has a disadvantage in that the polymer material is lower than the low molecular material in terms of lifetime, luminous efficiency, and color purity.

Therefore, in order to overcome such a problem, there is a demand for the development of a material capable of constituting a device by a wet process with low molecular weight and high solubility.

An object of the present invention is to introduce a molecule having a bulk three-dimensional structure as a ligand of the metal complex compound Inhibition of intermolecular interactions can of course lead to increased solubility of the compounds. It is an object of the present invention to provide a metal complex compound for an organic light emitting device.

In addition, by providing an electron donor and an electron pulling body to the ligand of the metal complex compound for an organic light emitting device, there is provided a metal complex compound and an organic light emitting display device for an organic light emitting device having improved injection and transfer characteristics of holes and electrons. There is a purpose.

Metal complex compound for an organic light emitting device for achieving the present invention It includes a silicone derivative ligand represented by the following formula (1).

n is an integer of 3 to 3, and a and b are each independently 0 or 1.

In the above formula

M is a metal forming an octahedral complex,

The ring of formula 1 is each a ring containing a double bond or consisting of a single bond,

L is a bidentate ligand of a monovalent anion coordinated to M via sp ² carbon and a heteroatom, or a bidentate ligand coordinated via a non-covalent electron pair of a heteroatom and a heteroatom of a monovalent anion,

Y ¹ is a monodentate ligand coordinated via a non-covalent electron pair of heteroatoms, Y ² is a monodentate ligand coordinated with a nitrogen atom of sp ² carbon and monovalent anion,

X ¹ to X ⁸ each represent a carbon atom or a nitrogen atom, and when any one of X ¹ to X ⁸ represents a carbon atom, each of R ¹ to R ⁸ bonded to X ¹ to X ⁸ representing the carbon atom is the number of carbon atoms. The substituent bonded to the atom is shown. When X ¹ to X ⁸ specific to the shown nitrogen, oxygen or sulfur atom, represents a R ¹ to R ⁸ is a lone pair, each coupled to the X ¹ to X ^8, the substituent represented by R ¹ to R ⁸ are X It may form a ring bonded to ¹ to X ⁸ .

Substituents represented by R ¹ to R ⁸ are each independently a hydrogen atom, a substituted or unsubstituted C 6 or more aryl group, a substituted or unsubstituted C 2 or more heteroaryl group, a substituted or unsubstituted C 1 or more alkyl group , Substituted or unsubstituted C2 or more amino group, substituted or unsubstituted C1 or more alkoxy group, halogen atom, nitro group, substituted or unsubstituted C6 or more arylene group, substituted or unsubstituted C2 or more heteroaryl group A ethylene group, a substituted or unsubstituted alkylene group having 1 or more carbon atoms.

The substituent represented by R ¹ to R ⁸ is characterized in that selected from the silicon atoms of the formula (2), (3).

R ⁹ , R ¹⁰ and R ¹¹ are each independently hydrogen, halogen, R ¹³ , OR ¹³ , N (R ¹³ ) ₂ , P (R ¹³ ) ₂ , P (OR ¹³ ) ₂ , POR ¹³ , PO ₂ R ¹³ , PO ₃ R ¹³ , SR ¹³ , Si (R ¹³ ) ₃ , Si (CH ₃ ) ₂ R ¹³ , Si (Ph) ₂ R ¹³ , B (R ¹³ ) ₂ , B (OR ¹³ ) ₂ , C ( O) R ¹³ , C (O) OR ¹³ , C (O) N (R ¹³ ) ₂ , CN, NO ₂ , SO ₂ , SOR ¹³ , SO ₂ R ¹³ , SO ₃ R ¹³ ,

R ¹³ is independently hydrogen, a linear or branched alkyl group having 1 to 30 carbon atoms, an alkenyl group having 1 to 30 carbon atoms, an alkynyl group having 1 to 30 carbon atoms, a heteroalkyl group having 1 to 30 carbon atoms, and an aryl having 3 to 40 carbon atoms. A heteroaryl group having 3 to 40 carbon atoms; Wherein R ¹³ is optionally substituted by one or more substituents Z;

Z is independently hydrogen, halogen, R ¹⁴ , OR ¹⁴ , N (R ¹⁴ ) ₂ , P (R ¹⁴ ) ₂ , P (OR ¹⁴ ) ₂ , POR ¹⁴ , PO ₂ R ¹⁴ , PO ₃ R ¹⁴ , SR ¹⁴ , Si (R ¹⁴ ) ₃ , Si (CH ₃ ) ₂ R ¹⁴ , Si (Ph) ₂ R ¹⁴ , B (R ¹⁴ ) ₂ , B (OR ¹⁴ ) ₂ , C (O) R ¹⁴ , C ( O) OR ¹⁴ , C (O) N (R ¹⁴ ) ₂ , CN, NO ₂ , SO ₂ , SOR ¹⁴ , SO ₂ R ¹⁴ or SO ₃ R ¹⁴ ,

R ¹⁴ is independently hydrogen, a straight or branched alkyl group having 1 to 30 carbon atoms, an alkenyl group having 1 to 30 carbon atoms, an alkynyl group having 1 to 30 carbon atoms, a heteroalkyl group having 1 to 30 carbon atoms, an aryl group having 3 to 40 carbon atoms, Any of heteroaryl group having 3 to 40 carbon atoms,

R ¹² is substituted or unsubstituted aryl group having 6 or more carbon atoms, substituted or unsubstituted heteroaryl group having 2 or more carbon atoms, substituted or unsubstituted carbon group having 1 or more carbon atoms, substituted or unsubstituted C2 or more amino group, substituted or unsubstituted Any one of an alkoxy group having 1 or more carbon atoms, a halogen atom, a nitro group, a substituted or unsubstituted arylene group having 6 or more carbon atoms, a substituted or unsubstituted heteroarylene group having 2 or more carbon atoms, or a substituted or unsubstituted alkyl group having 1 or more carbon atoms. .

And L is any one selected from the following ligands.

On the other hand, the metal complex compound for an organic light emitting device according to the present invention is characterized in that the general formula 1 is represented by the following general formula (1a) or 1b, but the present invention is not limited to the following representative examples.

An organic electroluminescent display device for achieving the present invention comprises a first electrode formed on a substrate; An organic thin film layer formed on the first electrode and formed of a metal complex compound for an organic light emitting device; It includes a second electrode formed on the organic thin film layer.

Herein, the organic thin film layer is formed on the first electrode layer and includes a first buffer layer for injecting and transporting holes, a light emitting layer formed on the first buffer layer, and a second buffer layer formed on the light emitting layer and injecting and transporting electrons. It is characterized by including any one or more layers.

The first electrode may be a transparent conductive metal selected from indium tin oxide (ITO) and indium zinc oxide (IZO).

The substrate is characterized in that the glass substrate or a flexible substrate.

The light emitting layer may be formed by any one of a spin coating method, an ink jet method, a vacuum deposition method, and a casting method.

Hereinafter, it demonstrates more concretely based on the Example of this invention. However, the following examples are provided to help the understanding of the present invention, and the scope of the present invention is not limited thereto.

Example 1 Synthesis of Formula 1a

Dissolve 10.0 g (1.1 eq, 31.03 mmol) of 9- (4-bromophenyl) -9H-carbazole in 70 ml of diethyl ether under nitrogen, and then n-butyllithium (1.6 M in n-Hexane) at -78 ^o C. Slowly add 22.3 ml (1.15 eq 32.44 mmol) dropwise.

The mixture was stirred at -78 ° C for 30 minutes, then heated to room temperature, and then further stirred for 10-20 minutes.

In another reaction vessel, 3.64 g (1.0 eq, 28,21 mmol) of dichloromethylsilane was added to 50 ml of diethyl ether and lowered to -78 ^° C.

The lithium reactant prepared above was slowly added dropwise through a cannula and then stirred for 30 minutes, followed by raising the temperature to room temperature and stirring for 3 hours.

In another reaction vessel, 7.32 g (1.1 eq, 31.03 mmol) of 1,4-dibromobenzene was dissolved in 50 ml of diethyl ether under nitrogen, followed by n-butyllithium (1.6 M in n-Hexane) at -78 ^o C. Slowly add 22.3 ml (1.15eq, 32.44 mmol) dropwise.

The mixture was stirred at -78 ^o C for 30 minutes, then heated to room temperature and further stirred for 10-20 minutes. After first lowering the temperature of the reactant to −78 ^° C., the iridium compound is slowly added dropwise through a cannula and then stirred for 30 minutes. And further stirred for 6 hours at room temperature.

After completion of the reaction, the mixture was extracted with diethyl ether, and the organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate is separated by silica gel column chromatography, and then recrystallized in nucleic acid to form intermediate 1 of white crystals.

Intermediate 1 was 5.0 g (1.0 eq, 10.95 mmol) and 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyridine 3.39 After dissolving g (1.1eq, 12.04 mmol) in 60 ml of tetrahydrofuran, 40 ml of a 2-molar concentration potassium carbonate solution was added dropwise.

0.38 g (0.03 eq, 0.33 mmol) of tetra (triphenylphosphino) palladium was added dropwise with the catalyst to reflux for 12 hours.

After completion of the reaction, tetra (triphenylphosphino) palladium was removed through celite filtration, followed by extraction with diethyl ether.

The organic layer may be dried over anhydrous magnesium sulfate, concentrated, and separated by silica gel column chromatography to form intermediate 2.

The intermediate 2 was prepared by adding 100 ml of glycerol to 1.77 g (2.0 eq, 3.34 mmol) and 1.0 g (1.0 eq, 1.43 mmol) of bis (2-phenylpyridine) acetoacetonatoiridium, and then at 200 ^° C. under nitrogen gas. Reflux for 24 hours.

The reaction solution was poured into 800 ml of distilled water, stirred for about 10 minutes, washed with distilled water and filtered under reduced pressure.

After the crystal obtained after the filter is dissolved in chloroform again, it is separated by silica gel comlum chromatography to form an iridium complex having a bulk particle structure, that is, a silicon derivative ligand which is a bulk ligand.

Example 2 Synthesis of Formula 1b

Synthesis of Intermediate 1: Same as Example 1

Intermediate 1 was dissolved 5.0g (1.0eq, 10.95 mmol) in 50 ml of tetrahydrofuran, and then 7.53 ml (1.1 eq, 12.04 mmol) of n-butyllithium (1.6M in n-Hexane) at -78 ^o C. Slowly add dropping.

2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2.05 g (1.1 eq, 12.04 mmol) was added dropwise, the temperature was raised to room temperature, and then under nitrogen. Stir for 8 hours.

After completion of the reaction, the mixture was extracted with diethyl ether, and the organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate can be separated by silica gel column chromatography to form intermediate 3.

5.0 g (2.1 eq, 9.93 mmol) and 1.84 g (1.0 eq, 4.72 mmol) of 1- (3'-pyridyl-2-yl) phenyl-3,5-dibromobenzene were added to the intermediate 3 with tetrahydrofuran 60. After dissolving in ml, 40 ml of 2 molar concentration aqueous potassium carbonate solution was added dropwise.

0.16 g (0.03 eq, 0.14 mmol) of tetra (triphenylphosphino) palladium is added dropwise with the catalyst to reflux for 12 hours.

After completion of the reaction, tetra (triphenylphosphino) palladium was removed through celite filtration, and then extracted with dimethyl ether.

The organic layer may be dried over anhydrous magnesium sulfate, concentrated, and separated by silica gel column chromatography to form intermediate 4.

100 ml of glycerol was added to 3.28 g (2.0 eq, 3.34 mmol) and 1.0 g (1.0 eq, 1.43 mmol) of bis (2-phenylpyridine) acetoacetonato iridium in Intermediate 4, followed by 24 at 200 ^o C under nitrogen gas. Reflux for time.

The reaction solution was poured into 800 ml of distilled water, stirred for about 10 minutes, washed with distilled water and filtered under reduced pressure. After the crystal obtained after the filter is dissolved in chloroform again, it is separated by silica gel comlum chromatography to form an iridium complex having a bulk particle structure, that is, a silicon derivative ligand which is a bulk ligand.

OLED device characteristics evaluation

The organic electroluminescent device can be fabricated using the metal complex compound for an organic electroluminescent device obtained from the present invention as a light emitting plate.

1 is a view showing an organic light emitting display device according to the present invention.

Referring to FIG. 1, an organic light emitting display device 1 includes a first electrode 20 made of a transparent conductive metal oxide, an organic thin film layer 100 including a light emitting region, and a second electrode 30 of a second electrode. It can be formed in a structure formed on the substrate 10 in order.

The substrate 10 may be used as a glass substrate or a flexible substrate having flexibility. The substrate is a Corning (15Ω / cm ² (1200 Å), forming a first electrode 20 on the substrate 10 and is formed in a size of 20mm x 20mm x 0.7mm.

 The first electrode 20 may use indium-tin-oxide (ITO) or indium-zn-oxide (IZO) as a transparent conductive metal oxide.

The substrate 10 on which the first electrode 20 is formed is ultrasonically cleaned in isopropyl alcohol and pure water for 5 minutes, and then UV ozone cleaned for 30 minutes.

PEDOT (poly (ethylenedioxy) thiophene) is spin coated to form the organic thin film layer 100 on the first electrode (20). In this case, the organic thin film layer 100 may include a light emitting layer 120, a first buffer layer 110, and a second buffer layer 130.

The first and second buffer layers 110 and 130 may include at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, or an electron injection layer, and may have an electron blocking layer or a hole blocking layer due to light emission characteristics of the light emitting layer 120. And the like may be further included.

Here, an embodiment will be described in which a hole blocking layer and an electron transporting layer are formed in the second buffer layer 130 without introducing the first buffer layer 110.

The light emitting layer 120 on the PEDOT forms a polyvinylcarbazole (PVK) and CBP (4,4'-N, N'-dicarbazolebiphenyl) (45:55) as a host, and a dopant metal complex compound according to the present invention. (1% to 30%, preferably 7%) and spin coating to a thickness of 500 kPa.

In addition, Balq is vacuum-deposited on the light emitting layer 120 to form a hole blocking layer having a thickness of 50 Å. Subsequently, Alq3 is vacuum deposited on the hole blocking layer to form an electron transport layer having a thickness of 200 kHz.

LiF 10kV (electron injection layer) and Al 1000kV (cathode) are sequentially vacuum deposited on the electron transport layer to form the second electrode 30 of LiF / Al metal to manufacture the organic light emitting display device 1. Can be.

When holes and electrons are injected from the first electrode 20 and the second electrode 30 when an electric field is applied to the organic light emitting display device 1, the injected holes and electrons are electrons of the organic thin film layer 100. The light emitting excitons may be formed by recombination in the light emitting layer 120 through the transport layer.

The light emitter can emit light while transitioning to ground states.

In the present invention, in the organic light emitting display device 1 in which the organic thin film layer 100 including the metal complex compound of Chemical Formula 1 as a light emitting material is provided between the first electrode 20 and the second electrode 30, At least one of the constituent layers of the organic thin film layer 100 contains the metal complex compound according to the present invention.

In order to understand the characteristics of the organic light emitting display device manufactured as described above, the initial driving voltage (turn-on voltage), the maximum luminance (cd / m ² ), and the driving voltage (Von) and current at the luminance of 1000 cd / m ² , respectively Efficiency (cd / A) and power efficiency (lm / W) were measured, and these results are shown in [Table 1].

As described above, although the metal complex compound used in the organic thin film layer 100 of the present invention is an organic electroluminescent display device manufactured by spin coating, which is a wet process rather than vacuum deposition, the color coordinates of x, y = [0.31, 0.61 ] To x, y = [0.32, 0.61], and emits light corresponding to pure green, and the luminous efficiency at 1000 cd / m ² is 18.45 cd / A to 18.96 cd / A, which is Ir (mppy). It was measured better than 3.

In addition, the power efficiency was 7.25 lm / w to 7.45 lm / w was better than the reference material.

In addition, the initial driving voltage is very low, 4.0V to 4.4V, and the maximum luminance is also 11,140 cd / m ² to 12,790 cd / m ^{2 It} is confirmed that the electrical stability is also improved.

As described above, the organic light emitting device using the metal complex compound according to the present invention introduces molecules having a bulk three-dimensional structure into the ligand of the metal complex compound, thereby increasing the distance between molecules, thereby decreasing crystallinity. The intermolecular interaction is suppressed to improve the electrical characteristics such as power efficiency, initial driving voltage, and light emission characteristics.

Also green Unlike Ir (ppy) ₃ or Ir (ppy) ₂ (acac), which is known to be effective among phosphorescent organic metal complex compounds, the metal complex compounds of the present invention exhibit excellent solubility characteristics in organic solvents such as toluene, chloroform, and chlorobenzene. Indicates.

Accordingly, the metal complex compound for an organic light emitting display device of the present invention is expected to be useful as a light emitting material of an organic light emitting display device.

The metal complex compound for an organic light emitting device according to the present invention is introduced into the ligand of the metal complex compound by introducing a molecule having a bulk three-dimensional structure as a ligand of the metal complex compound, as well as the effect of increasing the solubility of the compound thereby There is.

In addition, an organic light emitting display device manufactured using a metal complex compound for an organic light emitting device has an effect of improving the injection / transmission characteristics of holes and electrons by introducing an electron donor and an electron pulling body into a ligand of the metal complex compound. There is.

Claims (12)

A metal complex compound for an organic electroluminescent device comprising a silicon derivative ligand represented by Formula 1 below:

In Chemical Formula 1 n is an integer of 1 to 3, a and b are each independently 0 or 1, The ring of Formula 1 is each a ring containing a double bond or consisting of a single bond, M is a metal forming an octahedral complex, L is a bidentate ligand of a monovalent anion coordinated to M via sp ² carbon and a heteroatom, or a bidentate ligand coordinated via a non-covalent electron pair of a heteroatom and a heteroatom of a monovalent anion, Y ¹ is a monodentate ligand coordinated via a non-covalent electron pair of heteroatoms, Y ² is a monodentate ligand coordinated with a nitrogen atom of sp ² carbon and monovalent anion, X ¹ to X ⁸ each represent a carbon atom or a nitrogen atom, and when one selected from X ¹ to X ⁸ is a carbon atom, each of R ¹ to R ⁸ bonded to X ¹ to X ⁸ representing a carbon atom is respectively represented by the carbo atom; When the substituent is bonded and X ¹ to X ⁸ is selected from a nitrogen, oxygen or sulfur atom, R ¹ to R ⁸ bonded to X ¹ to X ⁸ each independently represent a non-covalent electron pair, and R ¹ to R substituents represented by ⁸ 's may be bonded to form a ring X ¹ to X ^8, The substituents represented by R ¹ to R ⁸ are each independently a hydrogen atom, an aryl group having 6 or more carbon atoms, a heteroaryl group having 2 or more carbon atoms, an alkyl group having 1 or more carbon atoms, an amino group having 2 or more carbon atoms, an alkoxy group having 1 or more carbon atoms, a halogen atom, A nitro group, an arylene group having 6 or more carbon atoms, a heteroarylene group having 2 or more carbon atoms, an alkylene group having 1 or more carbon atoms, However, at least one of the substituents represented by R ¹ to R ⁸ is selected from substituents containing silicon atoms represented by the following general formula (2) and (3),

R ⁹ , R ¹⁰ and R ¹¹ are each independently R ¹³ , OR ¹³ , N (R ¹³ ) ₂ , P (R ¹³ ) ₂ , P (OR ¹³ ) ₂ , POR ¹³ , PO ₂ R ¹³ , PO ₃ R ¹³ , SR ¹³ , Si (R ¹³ ) ₃ , Si (CH ₃ ) ₂ R ¹³ , Si (Ph) ₂ R ¹³ , B (R ¹³ ) ₂ , B (OR ¹³ ) ₂ , C (O) R ¹³ , C (O) OR ¹³ , C (O) N (R ¹³ ) ₂ , SOR ¹³ , SO ₂ R ¹³ , and SO ₃ R ¹³ Any one selected from, R ¹³ is independently a linear or branched alkyl group having 1 to 30 carbon atoms, an alkenyl group having 1 to 30 carbon atoms, an alkynyl group having 1 to 30 carbon atoms, a heteroalkyl group having 1 to 30 carbon atoms, an aryl group having 3 to 40 carbon atoms, and carbon atoms 3 to 40 heteroaryl groups; Wherein R ¹³ is substituted by one or more substituents Z, Z is independently R ¹⁴ , OR ¹⁴ , N (R ¹⁴ ) ₂ , P (R ¹⁴ ) ₂ , P (OR ¹⁴ ) ₂ , POR ¹⁴ , PO ₂ R ¹⁴ , PO ₃ R ¹⁴ , SR ¹⁴ , Si ( R ¹⁴ ) ₃ , Si (CH ₃ ) ₂ R ¹⁴ , Si (Ph) ₂ R ¹⁴ , B (R ¹⁴ ) ₂ , B (OR ¹⁴ ) ₂ , C (O) R ¹⁴ , C (O) OR ¹⁴ , Any one selected from C (O) N (R ¹⁴ ) ₂ , SOR ¹⁴ , SO ₂ R ^14, and SO ₃ R ¹⁴ , R ¹⁴ is any one selected from an aryl group having 3 to 40 carbon atoms and a heteroaryl group having 3 to 40 carbon atoms, R ¹² is any one selected from an amino group having 2 or more carbon atoms, an alkoxylene group having 1 or more carbon atoms, an arylene group having 6 or more carbon atoms, a heteroarylene group having 2 or more carbon atoms, and an alkylene group having 1 or more carbon atoms. The method of claim 1, A and b are pentagonal rings with a = b = 0 when 0, and with a = b = 1 or a = 0, b = 1 or a = 1, b = 0 when the ring is hexagonal A metal complex compound for organic electroluminescent devices. The method of claim 1, Formula 1 is an organic complex compound for an organic light emitting device, characterized in that the aromatic ring. The method of claim 1, Wherein L is a metal complex compound for an organic light emitting device, characterized in that any one selected from the following ligands.

The method of claim 1, The metal atom (M) forming the octahedral complex in Formula 1 is iridium metal complex compound for an organic light emitting device. Formula 1 is specifically a metal complex compound for an organic light emitting device, characterized in that represented by the formula (1a) or (1b).

A first electrode formed on the substrate; An organic thin film layer formed on the first electrode and formed of a metal complex compound for organic light emitting devices according to claims 1 to 6; An organic light emitting display device comprising a second electrode formed on the organic thin film layer. The method of claim 7, wherein The organic thin film layer A first buffer layer formed on the first electrode layer to inject and transport holes, a light emitting layer formed on the first buffer layer, and a second buffer layer formed on the light emitting layer and injecting and transporting electrons; An organic light emitting display device comprising a. The method of claim 7, wherein The first electrode is an organic light emitting display device, characterized in that the transparent conductive metal selected from ITO, IZO. The method of claim 7, wherein The substrate is an organic light emitting display device, characterized in that the glass substrate or a flexible substrate. The method of claim 7, wherein And the light emitting layer is formed by one of a spin coating method, an ink jet method, a casting method, and a vacuum deposition method. The method of claim 7, wherein The light emitting layer is an organic light emitting display device, characterized in that 1% to 10% of the metal complex compound is mixed with a dopant.

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