KR20070067775A - Iridium complex having luminescence property of ancillary ligand and organic electrophosphorescent substance using the same - Google Patents

Abstract

Provided are an iridium complex compound, which is capable of color control over the full luminescence region and has an excellent luminous efficiency, and an organic electrophosphorescent device using the same, which embodies full visible colors and white color through a photophysical process system. The iridium complex compound having a structure of a formula 1 follows a photophysical process luminescence mechanism in which an excitation from an iridium to a singlet state(MLCT^1, metal to ligand charge transfer) of the ligand(L) in the formula 1 occurs, inter-system crossing from the singlet state to a triplet state(MLCT^3) is generated by strong spin-orbit coupling, and inter-ligand energy transfer(ILET) to an energy level of an ancillary ligand(A) lower than the triplet state occurs.

Description

Iridium Complex having Luminescence Property of Ancillary Ligand and Organic Electrophosphorescent Substance Using the Same}

1 is a diagram of an "Inter-Ligand Energy Transfer" photophysical process system.

2 is a view showing the structure of the organic electrophosphorescent device of the present invention.

3 is a diagram showing the synthetic route of the final material.

4 is 1.0 × 10 ⁻⁵ M of a compound having a structure of Formula 30. A diagram showing the absorption and PL spectra of a dichloromethane solution and a film 5% doped with PMMA in PMMA.

5 is a diagram showing absorption and PL spectra of a 1.0 × 10 ⁻⁵ M dichloromethane solution of a compound having the structure of Formula 31 and a film doped with PMMA in 5% of the compound.

FIG. 6 is a diagram showing the absorption and PL spectra of a 1.0 × 10 ⁻⁵ M dichloromethane solution of a compound having the structure of Formula 13 and a film doped with PMMA at 5%.

7 is a diagram showing absorption and PL spectra of a 1.0 × 10 ⁻⁵ M dichloromethane solution of a compound having the structure of Formula 32 and a film doped with PMMA in 5% of the compound.

8 is a diagram showing absorption and PL spectra of a 1.0 × 10 ⁻⁵ M dichloromethane solution of a compound having the structure of Formula 33 and a film doped with PMMA in 5% of the compound.

FIG. 9 is a graph showing absorption and PL spectra of a 1.0 × 10 ⁻⁵ M dichloromethane solution of a compound having the structure of Formula 14 and a film doped with PMMA in 5% of the compound.

FIG. 10 is a diagram showing absorption and PL spectra of a 1.0 × 10 ⁻⁵ M dichloromethane solution of a compound having a structure of Formula 34 and a film doped with PMMA at 5%.

11 is a view showing the color coordinates of the eighth embodiment to the thirteenth embodiment.

12 is a view showing a light-emitting photograph of Example 8 to Example 13. FIG.

13 is a diagram showing the absorption and PL spectra of Comparative Example 1. FIG.

14 is a view showing a white electroluminescent device having a multi-layer structure as a conventional technology.

Field of invention

The present invention relates to an iridium complex compound and an organic electrophosphor device comprising the same, and more particularly, the present invention relates to a triplet emitter which is an iridium complex to which a photophysical process capable of providing red, green, blue and white electrophosphorescent devices is applied. (triplet emitter) and an organic electrophosphorescent device comprising the same.

Background of the Invention

The principle of a typical organic light emitting device is as follows. Holes injected from the anode into the valence band or HOMO of the hole injection layer proceed to the emitting layer through the hole transporting layer, and at the same time, the electron injection layer from the cathode The electron injected into the injection layer moves to the light emitting layer through an electron transporting layer and combines with the holes to form excitons. The exciton falls to the ground and emits light. Using the principle of the organic EL device, in 1987, Eastmann Kodak developed an organic light emitting device using TPD as the hole transport layer and Alq ₃ as the light emitting layer (Appl. Phys. Lett. 51, 913, 1987). .

The light emitting material refers to a material that absorbs energy in the form of electromagnetic radiation and emits the absorbed energy. Phosphorescent luminescent materials at room temperature store the energy absorbed for a considerable time and spontaneously release most of that energy. On the contrary, in the case of a fluorescent light emitting material, the energy spontaneously absorbed when exposed to excitation light emission energy is emitted as light emission energy within a very short time. A long-standing goal in the field of light emitting materials is to develop materials that emit light more efficiently at different wavelengths. In relation to phosphorescent light emitting materials, researches for increasing the amount of energy absorbed and emitted by a given amount of light emitting materials and researches for color correction are continuously conducted.

In the organic light emitting device, a fluorometer (CH Chen et. Al., Macromolecular Symposia, 125, pp. 1-48, 1997) and a phosphorescent luminescent material (S. Hoshino et. Al., Appl) are used to efficiently emit light at various wavelengths. Phys. Lett. 69, p. 224, 1996; MABaldo et. Al., Appl. Phys. Lett., 75, pp. 4-6, 1999; T. Tsutsui et. Al., Jpn, J. Appl. Phys. 38, L1502-L1504, 1999; C. Adachi et. Al., Appl. Phys. Lett., 77, pp. 904-906, 2000).

Excitons, which are molecules excited in fluorescence and phosphorescent luminescent materials, are different from each other in each case. The exciton, which emits light from the fluorescent light emitting material, is arranged in a symmetry in the ground state, and has a value of 1 equal to the spin state of the spin multiplicity. On the other hand, excitons that emit light from the phosphor emitters are arranged in anti-symmetry in the ground state, and the spin multiplicity has a value of 3. Here, excitons use the terms singlet and triplet for fluorescent and phosphorescent materials. During the operation of the OLED, electrical excitation produces 25% singlet excitons and 75% triplet excitons. Therefore, in the case of an OLED made of a fluorescent light emitting material, a large number of triplet excitons cannot be used and consumed as heat.

However, when phosphors are used as light emitters in OLEDs, both singlet and triplet excitons can be used for luminescence by Forster and Dexter energy transfer. To this end, phosphorescent organic molecules are used as light emitting materials that are doped into a suitable host as a light emitting layer (Baldo, M. A. et al., Nature 1998, 395, 151-154.).

Color tuning studies for phosphors with high luminous efficiency have been ongoing (Tsuboyama, A., et al. J. Am. Chem. Soc. 2003, 125, 12971-12979., Thompson, ME Inorg.Chem. 2001, 40, 1704-1711., Samuel, IDW AdV.Mater. 2004, 16, 557-560., Chen, CH AdV.Mater. 2005, 17, 285-289., Thompson, ME Polyhedron 2004 , 23, 419-428., Graetzel, MJ Am. Chem. Soc. 2003, 125, 8790-8797.). However, organometallic compounds including phosphor iridium metal through the synthesis of cyclometallated ligands through the modification of new divalent monovalent anion ligands are difficult to synthesize due to the steric and electronic reasons of iridium dimer. For this reason, color tuning studies through auxiliary ligand modification have been actively conducted. However, there have been many efforts to introduce auxiliary ligands to date, but the shortcomings of color tuning and low phosphorescence quantum efficiency have been reported (Thompson, MEJ Am. Chem. Soc. 2001, 123, 4304). -4312., De Cola, D. Chem. Commun. 2004, 1774-1775., Forrest, SR Appl. Phys. Lett. 2001, 79, 2082-2084., Hong, J.-I. Organometallics 2005, 24, 1578-1585.).

In addition, the organic electroluminescent device is attracting attention as a next-generation flat panel display device or a surface light source because it is advantageous in terms of power efficiency and has high luminance and high viewing angle.

In order to meet the need as a backlight or illumination in such an organic electroluminescent element liquid crystal, it is very important to realize white light emission.

US Patent Publication No. 6,875,524 of Eastman Kodak Corporation discloses a technique of stacking several light emitting layers or introducing several doped common layers to implement a white electroluminescent device. In this case, however, the device manufacturing process cost increases.

In the Korean Patent Application Publication No. 2004-75043 of Universial Display Corporation, a white organic light emitting device was implemented using a platinum complex compound as an electron blocking layer as a phosphor complex and a host material and an iridium metal complex compound as a light emitting layer. The CIE coordinates (0.33, 0.33) showed a shortcoming.

Therefore, it is very urgent to identify photophysical process mechanisms that enable high-efficiency and tonal adjustment over the entire visible light area, to develop materials, and to develop white organic light emitting devices that reproduce low manufacturing costs and high color purity.

Accordingly, the present inventors have attempted to provide a new phosphor device capable of defining a color over the entire emission area by identifying a photophysical process system and introducing an auxiliary ligand into the lithium complex.

SUMMARY OF THE INVENTION An object of the present invention is to identify a photophysical process system and to provide a display device that exhibits high luminous efficiency and enables color adjustment over the entire emission area.

Another object of the present invention is to identify a photophysical process system and to provide a new iridium complex compound capable of coloration over the entire luminescence area by introducing an auxiliary ligand into the iridium complex.

Still another object of the present invention is to provide an organic electrophosphor device and a white organic electrophosphor device using a new iridium complex compound.

The above and other objects of the present invention can be achieved by the present invention described below.

Summary of the Invention

The present invention can provide a new organic electrophosphorescent device capable of color adjustment over the entire emission area by introducing a luminescent auxiliary ligand into the iridium complex represented by the following formula (1). In addition, it is possible to fabricate an organic electrophosphorescent device capable of realizing a full visible light region and white color using a photophysical process system.

[Formula 1]

Hereinafter, the content of the present invention will be described in detail below.

Detailed Description of the Invention

The present invention controls the light emission of the light emitting layer of the iridium complex represented by the following Chemical Formula 1 by using the "Inter-Ligand Energy Transfer" photophysical process system of Type II shown in FIG. By using the light emitting area adjusting method, a full visible light region or a white light emitting organic electroluminescent device can be manufactured. In addition, it is possible to provide a compound capable of high luminous efficiency and color tone over the entire emission area.

[Formula 1]

The L of the general formula (1) is used as a bicyclo ligand of iridium metal screen can cause the energy transfer to the ancillary ligand A, and this taking place ^first MLCT excited dfppy (2,4-difluorophenylpyridine) from iridium as a structure that is not the emission center This results in a very effective inter-system crossing (ISC) from MLCT ¹ to MLCT ³ by strong spin-orbit coupling.

 It is not the type I luminescent mechanism that the conventional iridium complex compound showed, but the correct selection of the auxiliary ligand (A), which is used as an auxiliary ligand of iridium and causes energy transfer from the cyclometallated ligand represented by L to be the luminescence center. Likewise, the method of adjusting the emission region can be provided through the "Inter-Ligand Energy Transfer" photophysical process system, and an organic electrophosphorescent device can be manufactured.

The compound used in the light emitting layer of the organic electroluminescent device is characterized by the structure of the formula (1) and L and A are independent of each other.

L of Formula 1 is a structure that can be used as a cyclometallated ligand of iridium to cause energy transfer to the auxiliary ligand A, L is a structure that does not become a light emitting center, and includes the structure of Formulas 2 to 6 do.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, X is N or -C (R ₆ )-, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are independent of each other, and are each hydrogen, (1) F, Cl, A group comprising a halogen atom of Br, I, (2) a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ and derivatives thereof, wherein R' is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen Atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ Arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (3) an alkyl group of C ₁ -C ₂₀ , (4) OR ", SR", NR "Groups comprising a hetero atom of ₂ and the Derivative (where R "is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ unsubstituted alkyl group, a substituted or unsubstituted C ₁ - C ₂₀ alkoxy group, a substituted or unsubstituted A substituted C ₆ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group , A substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), ( 5) aryl groups and derivatives thereof, and (6) fused ring groups.

[Formula 6]

Although specific examples of the compounds of Formulas 2 to 6 have been mentioned as examples of L, they are not limited to these examples without departing from the spirit and scope of the present invention.

A of Formula 1 is used as a cyclometalating auxiliary ligand of iridium to induce energy transfer from a cyclometallating ligand represented by L, and includes a structure as follows.

A is an auxiliary ligand and is selected from the group consisting of compounds represented by the following Chemical Formulas 7 to 12 as bidentate ligands.

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Formulas 7 to 12, R ₁ , R ₂ , R ₃ , R _4, R _{5, and} R ₆ are each independently hydrogen, (1) F, Cl, Br, halogen atoms of I, (2) BR ' ₂ , a group comprising a hetero atom of PR ′ ₂ , SiR ′ ₃ and derivatives thereof, wherein R ′ is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ Alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted Selected from the group consisting of C ₂ -C ₂₀ heterocyclic groups.), (3) an alkyl group, (4) a group comprising hetero atoms of OR ″, SR ″, NR ″ ₂ and derivatives thereof, wherein R ″ is hydrogen Here, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ ring Aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (5) aryl group and derivatives thereof (6) a fused ring group, wherein X ₁ is a group represented by O, S, Se, CR ''' ₂ , wherein R''' is a hydrogen atom, a cyano group, group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ unsubstituted alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkyl alkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted Or an unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group, X ₂ is —NH -Or -NR- and selected from the group consisting of groups capable of bonding negatively charged iridium.

In addition, the present invention is an organic electrophosphorescent device comprising a light emitting layer consisting of an organic film between a pair of electrodes, wherein the light emitting layer is selected from the group consisting of the iridium complex compound of claim 1 and the iridium complex compound of formula 1-1 At least one iridium complex compound. The iridium complex compound of Formula 1-1 is excited in a singlet state (MLCT ¹ , metal to ligand change transter) to ligand (L) in iridium, and triplet state in singlet state by strong spin-orbit coupling ( Inter-system crossing (MLC) to MLCT ³ ) occurs and inter-ligand energy transfer (ILET) to a lower energy level of the auxiliary ligand (A ₂ ) than the triplet state. An organic electrophosphorescent device is provided, wherein the light emitting layer is a single light emitting layer that emits white light.

[Formula 1-1]

The ligand (L) is selected from the group consisting of compounds of Formulas 2 to 6;

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, X is N or -C (R ₆ )-, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are independent of each other, and are each hydrogen, (1) F, Cl, A group comprising a halogen atom of Br, I, (2) a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ and derivatives thereof, wherein R' is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen Atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ Arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (3) an alkyl group of C ₁ -C ₂₀ , (4) OR ", SR", NR "Groups comprising a hetero atom of ₂ and the Derivative (where R "is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ unsubstituted alkyl group, a substituted or unsubstituted C ₁ - C ₂₀ alkoxy group, a substituted or unsubstituted A substituted C ₆ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group , A substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), ( 5) aryl groups and derivatives thereof, and (6) fused ring groups;

[Formula 6]

In Formula 1-1, Auxiliary ligand A ₂ is represented by Formula 15 to Formula 29;

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

In Formulas 15 to 20, R ₁₁ , R ₂₁ , R ₃₁ , R _41, R _{51, and} R ₆₁ are each independently hydrogen, (1) halogen atoms of F, Cl, Br, I, and (2) BR ′. ₂ , a group comprising a hetero atom of PR ′ ₂ , SiR ′ ₃ and derivatives thereof, wherein R ′ is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ Alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted a C ₂ -C ₂₀ is selected from the group consisting of heterocyclic ring groups.), (3) alkyl group, (4) OR ", SR ", NR " group containing a hetero atom in the ₂ and derivatives thereof (where R" is Bovine atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (5) aryl group and the like Derivative, (6) a fused ring group, X ₁₁ is represented by O, S, Se, CR ''' ₂ where R''' is a hydrogen atom, a cyano group, a hydroxy group , Nitro group, halogen atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted Or an unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group, X ₂₁ is O, Representative of S, or C, and selected from the group consisting of groups capable of bonding negatively charged iridium;

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

In Formulas 21 to 26, X is O, S, or -C (R ₇ )-, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , and R ₇ are each independently of each other, and each of hydrogen, (1 ) A halogen atom of F, Cl, Br, I, (2) a group containing a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ and derivatives thereof, wherein R' is a hydrogen atom, a cyano group, or a hydroxyl group , Nitro group, halogen atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted Or an unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (3) alkyl group, (4) OR ", SR", NR " group and that containing the hetero atom of the ₂ Conductor (where R "is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ unsubstituted alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted A substituted C ₆ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group , A substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), ( 5) an aryl group and derivatives thereof, and (6) a fused ring group, wherein X 'is a group containing atoms of O, N, S, and C and having a negative charge to bond with iridium Selected from the group consisting of;

[Formula 27]

[Formula 28]

[Formula 29]

R ₁ in Formulas 27 to 29 is hydrogen, (1) an alkyl group. (2) a group comprising a hetero atom of OR ″, SR ″, NR ″ ₂ and a derivative thereof, wherein R ″ is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted Or an unsubstituted C ₂ -C ₂₀ heterocyclic group.), (3) an aryl group and its derivatives, and (4) a fused ring group, R ₂ , R ₃ , R ₄ are independent of each other and each comprises hydrogen, (1) a halogen atom of F, Cl, Br, I, (2) a group containing a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ , and Derivatives wherein R ′ is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted A substituted C ₆ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group , A substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), ( 3) an alkyl group, (4) a group comprising hetero atoms of OR ″, SR ″, NR ″ ₂ and derivatives thereof, wherein R ″ is a hydrogen atom, cyano group, hydroxy group, nitro group, halogen atom, substituted or unsubstituted A substituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or Unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl Amino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (5) aryl group and derivatives thereof, (6) condensation X '' is selected from the group consisting of fused ring groups, X '' is selected from the group consisting of groups containing O, N, S, C atoms and capable of bonding negatively charged iridium.

Although the following compounds are mentioned as specific examples of the above Chemical Formula 1 (Chemical Formulas 13 and 14) and Chemical Formula 1-1 (Chemical Formulas 30 to 35), the present invention is not limited to these examples without departing from the spirit and scope of the present invention.

[Formula 13]

[Formula 14]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

Formula 13, Formula 14, and Formula 30 to Formula 34 show the synthesis methods in Synthesis Examples 3 to 9 of the following Examples as specific examples of the present invention.

The organic electrophosphorescent device having the organic film using the iridium complex compound of the present invention described above and a method of manufacturing the same will be described below.

2 is a cross-sectional view showing the structure of the organic electrophosphorescent device of the present invention. First, an anode is formed by coating a material for an anode (anode) 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), indium zinc oxide (IZO), tin oxide (SnO 2), and zinc oxide (ZnO) are used as the anode electrode material.

Vacuum injection or spin coating a hole injection layer material over the anode electrode. The hole injection layer material is not particularly limited, and TCTA, m-MTDATA, IDE406 (Idemitsu Co., Ltd.) represented by the following structural formulas, such as CuPc or Starburst type amines represented by the following structural formulas, may be used as the hole injection layer. Can be used.

The hole transport layer material is vacuum thermally deposited or spin coated on the hole injection layer to form the hole transport layer. The hole transport layer material is not particularly limited, and is represented by the following structural formula: N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'- Diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine, N, N'-di (naphthalen-1-yl) -N, N represented by the following structural formula '-Diphenylbenzidine: α-NPD), IDE320 (manufactured by Idemitsu Corp.), and the like.

Subsequently, a light emitting layer is introduced on the hole transport layer, and the light emitting layer material is not particularly limited, and at least one iridium complex compound selected from the group consisting of the iridium complex compound of Formula 1 and the iridium complex compound of Formula 1-1 may be used alone or as a dopant. Can be used. When the compound is used as a dopant, the co-vacuum vapor deposition may be performed on CBP, TCB, TCTA, dmCBP, Liq, TPBI, Balq, BCP and the like represented by the following structural formulas. In addition, the polymer matrix may further include, and the polymer matrix may include PVK (polyvinyl carbazole).

When at least one iridium complex compound selected from the group consisting of the iridium complex compound of Formula 1 and the iridium complex compound of Formula 1-1 is used as a dopant, the doping concentration thereof is not particularly limited, but considering luminous efficiency, etc. It is preferable to use 1-20 weight part with respect to a total weight of 100 weight part of a host and a dopant. Further, when one or more of the iridium complex compounds are used in order to enable color crystallization over the entire emission area, for example, when using the iridium complex compounds of the formulas (35) and (34), the mixing ratio is from 3 to 7 to 7. It is preferable that it is the ratio of 8: 2.

A hole blocking layer forms a thin film on the light emitting layer as a vacuum deposition method or a spin coating method. At this time, the hole blocking material used is not particularly limited, but should have an ionization potential higher than that of the light emitting compound while having electron transport ability, and typically, Balq, BCP, TPBI, and the like are used. The electron transport layer forms a thin film on the hole blocking layer as a vacuum deposition method or a spin coating method. It does not restrict | limit especially as an electron carrying layer material, Alq3 can be used.

In addition, an electron injection layer may be laminated on the electron transport layer, which does not particularly limit the material. As an electron injection layer, materials, such as LiF, NaCl, CsF, Li2O, BaO, Liq, can be used.

Then, the organic EL element is completed by forming a cathode electrode by vacuum thermal evaporation of a cathode forming metal on the electron injection layer. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) and the like. In addition, a transmissive cathode using ITO and IZO may be used to obtain a front phosphor.

The organic electrophosphorescent device of the present invention may further form one or two intermediate layers as needed on the anode electrode, hole injection layer, hole transport layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, and cathode electrode. Do. In addition to the above-mentioned layers, an electron blocking layer may also be formed.

The present invention will be further illustrated by the following examples, which are only described for the purpose of illustrating the present invention and are not intended to limit the protection scope of the present invention.

Example

The overall synthetic route of the iridium complex of the present invention is shown in FIG.

Synthesis Example 1

Preparation of 2- (2,4-difluorophenyl) pyridine (dfppy).

In a round bottom flask equipped with reflux cooler, 2-bromopyridine (2.01 mL, 21.1 mmol), 2,4-difluorophenylboronic acid (4.00 g, 25.3 mmol) and tetrakis (triphenylphosphine) palladium (0 ) (0.732 g, 0.633 mmol) was added and dissolved in 50 mL of THF. Then 30 mL of 2N Na ₂ CO ₃ solution was poured, and the reaction mixture was maintained at 70 ° C. for 1 day. After the reaction, the cooled reactant was poured into water, and the organic solution layer was extracted with water and dichloromethane (50 mL × 3 times). Then dried over anhydrous magnesium sulfate.

Silica gel column purification (n-hexane: ethyl acetate = 5: 1) to obtain a clear solution quantitatively. (4.07 g, 21.0 mmol). TLC, Rf = 0.5 (n-hexane: ethyl acetate = 5: 1); ¹ H-NMR δ 6.89 (m, 1H), 7.1 (m, 1H), 7.28 (m, 1H), 7.75 (m, 2H), 8.00 (m, 1H), 8.71 (d, J = 3.5, 1H ); HRMS (EI) calculated M ⁺ 191.0544; observed M ⁺ 191.0546.

Synthesis Example 2

Preparation of [(dfppf) ₂ Ir (μ-Cl)] ₂ .

IrCl ₃ H ₂ O.HCl (Aldrich) (0.702 g, 2.35 mmol) and dfppy (2.00 g, 10.5 mmol) were dissolved in 2-EtOEtOH: H ₂ O = 60 mL: 20 mL and 140 ° C for 20 hours. At reflux and cooled. After cooling, the mixture was washed with acetone: ethanol = 60 mL: 60 mL and the yellow precipitate was filtered off. The product obtained above was recrystallized from n-hexane: toluene = 10 mL: 25 mL to give yellow crystals (2.28 g, 1.88 mmol). Yield 85%. HRMS (FAB) calculated M ⁺ 1216.0509; observed M ⁺ 1216.0499.

Synthesis Example 3

Preparation of Formula 30.

[(dfppf) ₂ Ir (μ-Cl)] ₂ (0.500 g, 0.411 mmol), sodium carbonate (0.479 g, 4.52 mmol) and 2.6 equivalents of 6-methylpicolinate were added to 30 mL of 2 Dissolved with EtOEtOH. After the gas was removed, the nitrogen atmosphere was maintained. The temperature was raised to 140 ° C. and the reaction mixture was stirred for 12 hours. After completion of the reaction, the cooled reaction mixture was poured into EtOAc (150 mL) and extracted with water (100 mL × 3 times) to remove 2-EtOEtOH. Silica gel column purification was carried out using ethyl acetate as a developing solvent, and crystals were obtained by recrystallization with ether: n-hexane = 10 mL: 40 mL. Iridium (III) bis (2- (2,4-difluorophenyl) pyridinato-N, C ^{2 '} ) (6-methylpicolinate) (0.530 g, 91%). ¹ H-NMR δ 1.99 (s, 3H), 5.37 (dd, J = 8.8, 2.2, 1H), 5.79 (dd, J = 8.9, 2.4, 1H), 6.39 (m, 2H), 6.99 (t, J = 7.5, 1H), 7.17 (t, J = 7.0, 1H), 7.31 (d, J = 7.7, 1H), 7.60 (d, J = 5.3, 1H), 7.79 (m, 2H), 7.86 (d , J = 7.7, 1H), 8.28 (m, 2H), 8.69 (d, J = 6.8, 1H); MS (FAB) m / z 710 (M ⁺ + 1), 573, 154, 136. Anal. Calcd for C ₂₉ H ₁₈ F ₄ IrN ₃ O ₂ : C, 49.15; H, 2.56; N, 5.93. Found: C, 48.94; H, 2. 44; N, 6.10.

Synthesis Example 4

Preparation of Formula 31.

The same synthesis method as in Synthesis Example 3 was used except that quinaldinate was used as an auxiliary ligand. Iridium (III) bis (2- (2,4-difluorophenyl) pyridinato-N, C ^{2 '} ) (quinaldinate) (0.569 g, 93%). ¹ H-NMR δ5.43 (d, J = 8.8, 1H), 5.94 (d, J = 8.8, 1H), 6.47 (m, 2H), 6.86 (t, J = 6.6, 1H), 7.12 (t, J = 7.0, 1H), 7.38 (m, 1H), 7.59 (m, 2H), 7.69 (t, J = 8.3, 1H), 7.76 (t, J = 7.9, 1H), 7.89 (m, 2H), 8.19 (d, J = 8.8, 1H), 8.31 (d, J = 9.0, 1H), 8.44 (m, 1H), 8.53 (m, 1H), 8.67 (d, J = 5.0, 1H); MS (FAB) m / z 746 (M ⁺ + 1), 573, 154. Anal. Calcd for C ₃₂ H ₁₈ F ₄ IrN ₃ O ₂ : C, 51.61; H, 2. 44; N, 5.64. Found: C, 51.66; H, 2. 34; N, 5.80.

Synthesis Example 5

Preparation of Formula 13.

The same synthesis method as in Synthesis Example 3 was used except that picolinamide was used as an auxiliary ligand. Iridium (III) bis (2- (2,4-difluorophenyl) pyridinato-N, C ^{2 '} ) (picolinamide) (0.518 g, 91%). ¹ H-NMR δ5.61 (d, J = 9.0, 1H), 5.86 (d, J = 8.8, 1H), 6.44 (m, 1H), 6.94 (m, 1H), 7.12 (t, J = 6.8, 1H), 7.32 (m, 1H), 7.44 (d, J = 5.1, 1H), 7.74 (m, 4H), 7.88 (m, 1H), 8.26 (m, 3H), 8.85 (d, J = 5.1, 1H); MS (FAB) m / z 695 (M ⁺ + 1), 573, 136. Anal. Calcd for C ₂₈ H ₁₇ F ₄ IrN ₄ O: C, 48.48; H, 2.47; N, 8.08. Found: C, 48.74; H, 2. 44; N, 8.30.

Synthesis Example 6

Preparation of Formula 32.

The same synthesis method as in Synthesis Example 3 was used except that isoquinolinate was used as an auxiliary ligand. Iridium (III) bis (2- (2,4-difluorophenyl) pyridinato-N, C ^{2 '} ) (isoquinolinate) (0.593 g, 97%). ¹ H-NMR δ5.58 (dd, J = 8.5, 2.3, 1H), 5.85 (dd, J = 8.7, 2.2, 1H), 6.46 (m, 2H), 6.91 (t, J = 6.0, 1H), 7.17 (t, J = 6.4, 1H), 7.42 (d, J = 5.7, 1H), 7.76 (m, 9H), 8.24 (d, J = 8.6, 1H), 8.31 (d, J = 9.3, 1H) , 8.80 (d, J = 6.2, 1 H), 10.23 (m, 1 H); MS (FAB) m / z 746 (M ⁺ + 1), 573,154. Anal. Calcd for C ₃₂ H ₁₈ F ₄ IrN ₃ O ₂ : C, 51.61; H, 2. 44; N, 5.64. Found: C, 51.49; H, 2.54; N, 5.77.

Synthesis Example 7

Preparation of Formula 33.

The same synthesis method as in Synthesis Example 3 was used except that pyrazinate was used as an auxiliary ligand. Iridium (III) bis (2- (2,4-difluorophenyl) pyridinato-N, C ^{2 '} ) (pyrazinate) (0.538 g, 94%). ¹ H-NMR δ5.52 (dd, J = 8.8, 2.6, 1H), 5.82 (dd, J = 8.4, 2.4, 1H), 6.47 (m, 2H), 7.03 (t, J = 7.0, 1H), 7.24 (m, 1H), 7.42 (m, 1H), 7.78 (m, 1H), 7.83 (t, J = 8.3, 1H), 8.27 (d, J = 8.3, 1H), 8.32 (d, J = 8.8 , 1H), 8.70 (m, 1H), 8.74 (d, J = 2.7, 1H), 9.50 (d, J = 1.3, 1H); MS (FAB) m / z 697 (M ⁺ + 1), 573, 154. Anal. Calcd for C ₂₇ H ₁₅ F ₄ IrN ₄ O ₂ : C, 46.62; H, 2. 17; N, 8.05. Found: C, 46.60; H, 2. 32; N, 8.10.

Synthesis Example 8

Preparation of Formula 14.

The same synthesis method as in Synthesis Example 3 was used except that pyrazinamide was used as an auxiliary ligand. Iridium (III) bis (2- (2,4-difluorophenyl) pyridinato-N, C ^{2 '} ) (pyrazineamide) (0.519 g, 91%). ¹ H-NMR δ5.56 (d, J = 6.4, 1H), 5.83 (d, J = 8.4, 1H), 6.46 (m, 2H), 7.00 (t, J = 6.2, 1H), 7.17 (t, J = 6.2, 1H), 7.42 (d, J = 4.4, 1H), 7.71 (m, 1H), 7.79 (t, J = 7.5, 2H), 8.28 (m, 2H), 8.63 (d, J = 3.9 , 1H), 8.80 (d, J = 5.0, 1H), 9.44 (s, 1H); MS (FAB) m / z 696 (M ⁺ + 1), 573, 154. Anal. Calcd for C ₂₇ H ₁₆ F ₄ IrN ₅ O: C, 46.68; H, 2. 32; N, 10.08. Found: C, 46.94; H, 2. 32; N, 9.86.

Synthesis Example 9

Preparation of Formula 34.

The same synthesis method as in Synthesis Example 3 was used except that quinoxalinate was used as an auxiliary ligand. Iridium (III) bis (2- (2,4-difluorophenyl) pyridinato-N, C ^{2 '} ) (quinoxalinate) (0.533 g, 87%). ¹ H-NMR (600 MHz) δ5.41 (dd, J = 6.5, 2.1, 1H), 5.94 (d, J = 6.5, 2.1, 1H), 6.45 (m, 1H), 6.54 (m, 1H), 6.91 (t, J = 6.4, 1H), 7.17 (t, J = 6.4, 1H), 7.49 (t, J = 7.5, 1H), 7.54 (d, J = 5.7, 1H), 7.72 (m, 2H) , 7.82 (m, 2H), 8.21 (d, J = 4.2, 1H), 8.23 (d, J = 4.2, 1H), 8.33 (d, J = 4.3, 1H), 8.64 (d, J = 2.9, 1H ); MS (FAB) m / z 747 (M ⁺ + 1), 573, 154. Anal. Calcd for C ₃₁ H ₁₇ F ₄ IrN ₄ O ₂ : C, 49.93; H, 2. 30; N, 7.51. Found: C, 49.94; H, 2.53; N, 7.86.

Example 1

UV-vis (ultraviolet-visible) and PL (Photoluminescence) in a thin film state by doping the iridium complex 5 wt% PMMA polymer in the CH ₂ Cl ₂ solution of the iridium complex represented by the formula (30) prepared according to the synthesis example The properties were examined and the resulting UV-vis and PL spectra are shown in FIG. 3.

Examples 2-7

Instead of the compound of Example 1, the compound represented by the formula (31), formula (13), formula (32), formula (33), formula (14) and formula (34), respectively, was prepared in the same manner as in Example 1 to prepare a thin film of UV-vis and PL The characteristics were examined and the results are sequentially shown in FIGS. 4 to 9.

Example 8

In the CH ₂ Cl ₂ solution, the PMMA polymer was doped with 5 wt% of the iridium complex compounds 35 and 34 in an iridium complex compound at a ratio of 3: 7, and PL (Photoluminescence) characteristics in the thin film state were examined. As a result, CIE (0.45, 0.39) was emitted.

Example 9

In the CH ₂ Cl ₂ solution, the PMMA polymer was doped with 5 wt% of the iridium complex compounds 35 and 34 in an iridium complex compound at a ratio of 4: 6, and the PL (Photoluminescence) characteristics in the thin film state were examined. As a result, CIE (0.43, 0.38) was emitted.

Example 10

In the CH ₂ Cl ₂ solution, the PMMA polymer was doped with 5 wt% of the iridium complex compounds 35 and 34 in an iridium complex compound at a ratio of 5: 5, and the PL (Photoluminescence) characteristics in the thin film state were examined. As a result, CIE (0.39, 0.38) was emitted.

Example 11

In the CH ₂ Cl ₂ solution, the PMMA polymer was doped with 5 wt% of the iridium complex compounds 35 and 34 to the PMMA in a ratio of 6: 4, and the PL (Photoluminescence) characteristics of the PMMA were examined. As a result, white light emission of CIE (0.33, 0.38) was performed.

Example 12

In the CH ₂ Cl ₂ solution, the PMMA polymer was doped with 5 wt% of the iridium complex compounds 35 and 34 to the PMMA in a ratio of 7: 3, and the PL (Photoluminescence) characteristics in the thin film state were examined. As a result, CIE (0.30, 0.38) was emitted.

Example 13

In the CH ₂ Cl ₂ solution, the PMMA polymer was doped with 5 wt% of the iridium complex compounds 35 and 34 in the ratio of 8: 2 to the PMMA, and the PL (Photoluminescence) characteristics of the thin film were examined. As a result, CIE (0.23, 0.37) was emitted.

[Formula 35]

[Formula 34]

Comparative Example 1

In the CH ₂ Cl ₂ solution, the PMMA polymer was doped with 5 wt% of the iridium complex compounds 35 and 36, which are iridium complex compounds, at a ratio of 6: 4, and the PL (Photoluminescence) characteristics in the thin film state were examined. As a result, light emission in a form different from the photophysical process of the present invention was performed.

[Formula 36]

As can be seen from the results of Examples 1 to 7, it was shown that the photoluminescent process system of the interligand energy transfer was able to achieve excellent luminous efficiency and color tone in the entire visible light region.

In addition, as shown in the results of Examples 8 to 13, when the auxiliary ligands of the present invention to which the photophysical process system of interligand energy transfer is applied, the luminous efficiency is excellent and color tone and electrophosphorescence in the entire visible light region are excellent. The device is possible.

According to the present invention, the introduction of an auxiliary ligand into the iridium complex based on the photophysical process system enables color correction over the entire luminescence region, and can provide new phosphorescent materials having excellent luminescence efficiency, and high luminescence efficiency. It is possible to provide an excellent organic electrophosphorescent device through a photophysical process system that enables color adjustment over the entire emission area.

Claims (11)

In iridium, the singlet state to the ligand (L) of formula 1 (MLCT ¹ excitation occurs with a metal to ligand change transter, and an inter-system crossing (ISC) from a singlet state to a triplet state (MLCT ³ ) occurs due to strong spin-orbit coupling. An iridium complex compound having the structure of Formula 1 characterized by following a photophysical process luminescent mechanism of inter-ligand energy transfer (ILET) at a lower energy level of the auxiliary ligand (A) than the antistate: [Formula 1]

In Formula 1, A ₁ is a heterocyclic ring containing nitrogen, and a pyridyl group, a pyrimidyl group, a triazine group, an imidazole group, and a pyrrole, wherein L is a ligand R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ are independent of one another and each comprises hydrogen, (1) a halogen atom of F, Cl, Br, I, (2) a group containing a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ , and derivatives thereof R 'is a hydrogen atom, cyano group, hydroxy group, nitro group, halogen atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C _6- C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocycle group consisting guneu From is selected.), (3) alkyl group, (4) a _{C 1 -C 20 OR ", SR} ", " group and derivatives thereof containing heteroatoms of ₂ (where R" NR is a hydrogen atom, a cyano group, Hydroxy group, nitro group, halogen atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or Unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl Amino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (5) aryl group and derivatives thereof, (6) condensation Selected from the group consisting of fused ring groups; The ligand (L) is selected from the group consisting of compounds of the following formulas (2) to (6): [Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, X is N or -C (R ₆ )-, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are independent of each other, and are each hydrogen, (1) F, Cl, A group comprising a halogen atom of Br, I, (2) a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ and derivatives thereof, wherein R' is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen Atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ Arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (3) an alkyl group of C ₁ -C ₂₀ , (4) OR ", SR", NR "Groups comprising a hetero atom of ₂ and the Derivative (where R "is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ unsubstituted alkyl group, a substituted or unsubstituted C ₁ - C ₂₀ alkoxy group, a substituted or unsubstituted A substituted C ₆ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group , A substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), ( 5) aryl groups and derivatives thereof, and (6) fused ring groups: [Formula 6]

A is an auxiliary ligand and selected from the group consisting of compounds represented by the following Chemical Formulas 7 to 12 as a bidentate ligand; [Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

In Formulas 7 to 12, R ₁ , R ₂ , R ₃ , R _4, R _{5, and} R ₆ are each independently hydrogen, (1) F, Cl, Br, halogen atoms of I, (2) BR ' ₂ , a group comprising a hetero atom of PR ′ ₂ , SiR ′ ₃ and derivatives thereof, wherein R ′ is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ Alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted a C ₂ -C ₂₀ is selected from the group consisting of heterocyclic ring groups.), (3) alkyl group, (4) OR ", SR ", NR " group containing a hetero atom in the ₂ and derivatives thereof (where R" is hydrogen Here, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl hwandoen Groups, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (5) aryl group and derivatives thereof, (6) selected from the group consisting of fused ring groups, wherein X ₁ is a group represented by O, S, Se, CR ''' ₂ wherein R''' is a hydrogen atom, a cyano group, or a hydroxy group , a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ unsubstituted alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkyl alkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted Or an unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group, X ₂ is —NH -, -NR- and selected from the group consisting of groups capable of bonding negatively charged iridium. The iridium complex compound of claim 1, wherein the iridium complex compound is a compound represented by the following Formula 13 or Formula 14. [Formula 13]

[Formula 14]

An organic electrophosphorescent device comprising a light emitting layer made of an organic film between a pair of electrodes, wherein the light emitting layer comprises at least one iridium complex compound selected from the group consisting of the iridium complex compound of claim 1. Organic electrophosphorescent element. The organic electrophosphorescent device according to claim 3, wherein the light emitting layer comprises an iridium complex compound selected from the group consisting of Formula 13, Formula 14, and mixtures thereof. [Formula 13]

[Formula 14]

The organic electroluminescent device according to claim 3, wherein the light emitting layer comprises 1 to 20 parts by weight of the at least one iridium complex compound as a dopant based on 100 parts by weight of the total of the host and the dopant. The device of claim 3, wherein the light emitting layer further comprises PVK, which is a polymer matrix. In an organic electrophosphorescent device comprising a light emitting layer made of an organic film between a pair of electrodes, the light emitting layer is at least one iridium selected from the group consisting of the iridium complex compound of claim 1 and the iridium complex compound of formula 1-1 A single light emitting layer comprising a complex compound; And The iridium complex compound is excited from the iridium to the ligand (L) in a singlet state (MLCT ¹ , metal to ligand change transter), and from the singlet state to the triplet state (MLCT ³ ) by strong spin-orbit coupling. Inter-system crossing (ISC) occurs and photophysical inter-ligand energy transfer (ILET) to lower energy levels of the auxiliary ligand (A ₂ ) than the triplet state Following the process light emitting mechanism; An organic electrophosphor device which emits white light: [Formula 1-1]

The ligand (L) is selected from the group consisting of compounds of Formulas 2 to 6; [Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, X is N or -C (R ₆ )-, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are independent of each other, and are each hydrogen, (1) F, Cl, A group comprising a halogen atom of Br, I, (2) a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ and derivatives thereof, wherein R' is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen Atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ Arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (3) an alkyl group of C ₁ -C ₂₀ , (4) OR ", SR", NR " group containing a hetero atom, and ₂ Derivative (where R "is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ unsubstituted alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted A substituted C ₆ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group , A substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), ( 5) aryl groups and derivatives thereof, and (6) fused ring groups; [Formula 6]

In Formula 1-1, Auxiliary ligand A ₂ is represented by Formula 15 to Formula 29; [Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

In Formulas 15 to 20, R ₁₁ , R ₂₁ , R ₃₁ , R _41, R _{51, and} R ₆₁ are each independently hydrogen, (1) halogen atoms of F, Cl, Br, I, and (2) BR ′. ₂ , a group comprising a hetero atom of PR ′ ₂ , SiR ′ ₃ and derivatives thereof, wherein R ′ is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ Alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted a C ₂ -C ₂₀ is selected from the group consisting of heterocyclic ring groups.), (3) alkyl group, (4) OR ", SR ", NR " group containing a hetero atom in the ₂ and derivatives thereof (where R" is Bovine atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (5) aryl group and the like Derivative, (6) a fused ring group, X ₁₁ is represented by O, S, Se, CR ''' ₂ where R''' is a hydrogen atom, a cyano group, a hydroxy group , Nitro group, halogen atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted Or an unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group, X ₂₁ is O, Representative of S, or C, and selected from the group consisting of groups capable of bonding negatively charged iridium; [Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

In Formulas 21 to 26, X is O, S, or -C (R ₇ )-, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , and R ₇ are each independently of each other, and each of hydrogen, (1 ) A halogen atom of F, Cl, Br, I, (2) a group containing a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ and derivatives thereof, wherein R' is a hydrogen atom, a cyano group, Period, nitro group, halogen atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted A C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, a substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, A substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (3) alkyl group, (4) OR ", SR", NR "group, and those containing a hetero atom in the ₂ Conductor (where R "is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ unsubstituted alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted A substituted C ₆ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group , A substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), ( 5) an aryl group and derivatives thereof, and (6) a fused ring group, wherein X 'is a group containing atoms of O, N, S, and C and having a negative charge to bond with iridium Selected from the group consisting of; [Formula 27]

[Formula 28]

[Formula 29]

R ₁ in Formulas 27 to 29 is hydrogen, (1) an alkyl group. (2) a group comprising a hetero atom of OR ″, SR ″, NR ″ ₂ and a derivative thereof, wherein R ″ is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted Or an unsubstituted C ₂ -C ₂₀ heterocyclic group.), (3) an aryl group and its derivatives, and (4) a fused ring group, R ₂ , R ₃ , R ₄ are independent of each other and each comprises hydrogen, (1) a halogen atom of F, Cl, Br, I, (2) a group containing a hetero atom of BR ' ₂ , PR' ₂ , SiR ' ₃ , and Derivatives wherein R ′ is a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted A substituted C ₆ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group , A substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or a substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), ( 3) an alkyl group, (4) a group comprising hetero atoms of OR ″, SR ″, NR ″ ₂ and derivatives thereof, wherein R ″ is a hydrogen atom, cyano group, hydroxy group, nitro group, halogen atom, substituted or unsubstituted A substituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or Unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₁ -C ₂₀ alkyl Amino group, substituted or unsubstituted C ₆ -C ₂₀ arylamino group, or substituted or unsubstituted C ₂ -C ₂₀ heterocyclic group.), (5) aryl group and derivatives thereof, (6) condensation Is selected from the group consisting of fused ring groups, X '' is selected from the group consisting of groups containing O, N, S, C atoms and capable of bonding negatively charged iridium. The organic electroluminescent device according to claim 7, wherein the light emitting layer comprises an iridium complex compound selected from the group consisting of iridium complex compounds represented by the following Chemical Formulas 13, 14, 30, and 35, and mixtures thereof. [Formula 13]

[Formula 14]

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

The organic electroluminescent device according to claim 7, wherein the light emitting layer comprises 1 to 20 parts by weight of the at least one iridium complex compound as a dopant based on 100 parts by weight of the total of the host and the dopant. The optical device of claim 7, wherein the light emitting layer further comprises PVK which is a polymer matrix. The organic compound of claim 7, wherein the at least one iridium complex compound applied to the light emitting layer is a mixture of the following iridium complex compounds of Formula 35 and Formula 34 in a ratio of 3: 7 to 8: 2. Electric phosphor: [Formula 34]

[Formula 35]

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