KR20140052501A - Method for mnufacturing of blue phosphorescence composition and organic light emittin diode comprising the same - Google Patents

Abstract

A method for manufacturing a blue phosphorescent composition represented by chemical formula 1 according to an embodiment of the present invention includes a step of reacting iridium dimer ([IrL_2Cl]_2) linked by a chlorine atom by enhancing the concentration of a ligand 2 to 100 times higher than the concentration of an iridium reactant at 100-300°C for 1 minute to 10 hours using microwaves.

Description

TECHNICAL FIELD [0001] The present invention relates to a method of manufacturing a blue phosphorescent compound, and an organic electroluminescent device including a blue phosphorescent compound. BACKGROUND ART < RTI ID = 0.0 >

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device, and more particularly, to a novel method for producing a blue phosphorescent compound and an organic electroluminescent device including a blue phosphorescent compound.

The image display device that realizes various information on the screen is a core technology of the information communication age and it is becoming thinner, lighter, more portable and higher performance. In recent years, along with the development of an information society, various types of display apparatuses have been increasingly demanded, and various kinds of displays such as a liquid crystal display (LCD), a plasma display panel (PDP), an electro luminescent display (ELD) Research on devices is actively under way. Among them, an organic light emitting diode (OLED) is an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode). When electrons and holes are injected into the organic light emitting layer, It is a device that emits.

The organic electroluminescent device is a self-luminous type that emits light by itself and does not require a backlight for light emission, and can be made thinner than an LCD having a separate light source, and can be manufactured in a bendable form. In addition, it has advantages of easy pattern formation and mass production by membrane fabrication technology, self-luminous device is excellent in luminance and field angle characteristics, has fast response speed, low driving voltage (less than 10V) and high color recall Have.

The organic electroluminescent device can realize blue, green, and red light emitting devices depending on how the light emitting layer is formed. In the light emitting material, excitons are formed by recombination of electrons and holes injected from both electrodes, and light is generated while stabilizing to the ground state. An exciton blocking layer having excellent stability may be used to prevent the exciton formed at this time from being quenched. The exciton has 1: 3 ratio of singlet and triplet. In case of fluorescence, only singlet exciton is used. In case of phosphorescence, both singlet and triplet can be used to obtain better luminous efficiency. Since the phosphorescent material can have a very high quantum efficiency as compared with the fluorescent material, it has been widely studied as an important method for increasing the efficiency of the organic electroluminescent device and lowering the power consumption.

2001, 40, 1704-1711, J. Am. Chem. Soc. 2001, 123, 4304-7111, 2002) 4312), various iridium complexes have been synthesized and various studies have been conducted on their luminescence phenomena. In 1974 M. nonoyame developed the synthesis of chloride bridged iridium dimer and then synthesized various chloride bridged iridium dimers and synthesized iridium complexes with three bidentate ligands. Chem. Soc. 1984, 106, 6647-6653, Inorg. Chem. 1993, 32, 3081-3087)

In 2001, ME Thompson and co-workers synthesized an iridium complex with an ancillary ligand by reacting chloride bridged iridium dimer with acetylacetone. The resulting iridium complex was reacted with a (CΛN) ₃ Ir ligand to introduce three bidentate ligands (CΛN) ₃ Ir was reported. A chloride bridged iridium dimer was synthesized by using 4,6-difluorophenyl pyridine and reacted with 2-picolinic acid to synthesize an iridium complex Firpic with blue phosphorescence. Chem. Soc. 2001, 123, 4304-4312, Appl. Phys. Lett. 2001, 79 (13), 2082-2084)

In 2001, DuPont synthesized fac-tris-cyclometalated arylpyridine Ir complexes with IrCl ₃ and fluorinated 2-arylpyridine in the presence of AgO ₂ CCF ₃ (Chem. Commun. 2001, 1494-1495, WO 02/02714 A2 ) in addition, Ir (acac) using a ₃ Ir (ppy) ₃ derivative in one step synthesis method and (Inorg. Chem. 1991, 30 , 1685-1687, WO 2002/60910, US 7790888 B2, J. Am. Chem. 1994, 33, 545-550, Adv. Mater. 2003, 15 (1) (2003), 125, 12971-12979), a method of synthesizing iridium complexes using a chloride bridged iridium dimer and AgSO ₃ CF ₃ has also been reported 11), 884-888), and a synthetic method using tridecane as a solvent has also been developed (US 2008/0297033 A1).

In 2009, S. Suzuki and co-workers reported the synthesis of iridium complexes with three CΛN ligands by reacting a chloro bridged iridium dimer and a CΛN ligand in the presence of mesitylene solvent and AgOTf (WO 2009/011447 A2) ) ₃ was synthesized in a single step in ethylene glycol solvent (CΛN) ₃ Ir complex (Inorg. Chem., 48, 1030-1037, US 2008/0297033 A1). In 2008, BASF reported that imidazolium salt can be reacted with a base to form a carbene derivative, which can then be reacted with [Ir (COD) Cl] ₂ to synthesize an iridium complex with three carbenes incorporated (US 2008/0018221 A1, US 2009/0096367 A1), and in 2010, the synthesis of iridium complexes with three carbene derivatives was reported using Ag ₂ CO ₃ and Na ₂ CO ₃ (Eur. J. Inorg. -933).

However, as described above, various methods for synthesizing an organic iridium compound have been introduced, but synthesis is not performed as in the literature, and synthesis yield varies greatly depending on the type of ligand. Particularly, when a ligand having a steric hindrance is used, a phenomenon that synthesis yield is very low is observed, and it has been difficult to separate and purify by various by-products. In addition, even if most of the reactions are short, it takes more than 1 day and 4 to 5 days long. Therefore, it is necessary to improve the existing synthesis method to synthesize Iridium complexes more effectively.

The present invention provides a method for producing a blue phosphorescent compound with improved synthesis yield of an iridium compound and an organic electroluminescent device including a blue phosphorescent compound.

According to one embodiment of the present invention, there is provided a method for preparing a blue phosphorescent compound represented by the following formula (1), which comprises reacting an iridium dimer [IrL ₂ Cl] ₂ ) and the ligand are reacted for 1 minute to 10 hours with the concentration of the iridium reactant being 2 to 100 times higher than the concentration of the iridium reactant.

[Chemical Formula 1]

Wherein X ₁ , X ₂ , X ₃ and X ₄ are each independently selected from a nitrogen atom or a carbon atom and A is a 5- to 6-membered nitrogen heteroaromatic group consisting of X ₁ -X ₂ -N Group, and B is a 5- to 6-membered aromatic or heteroaromatic group consisting of CX ₃ -X ₄ . X ₅ -L 1 -X ₆ is a 2-position ligand, X ₅ and X ₆ are each independently selected from a carbon atom, a nitrogen atom or an oxygen atom, and L 1 is an atomic group forming a two-terminal ligand. n is an integer of 1 to 3, a is an integer of 0 to 3, and b is an integer of 0 to 3.

And, Ra and Rb are each independently, hydrogen, D, F, Cl, of Br halogen, CF _3, cyano group, C1 to alkyl groups of C18, C1 to alkoxy groups, C6 or more substituted or unsubstituted aromatic group ring of C18 , A substituted or unsubstituted aliphatic cyclic group of C5 or more, an amine group of C1 to C18, an amine group substituted with an aromatic group of C6 or more, an amine group substituted with a aliphatic cyclic group of C5 or more, an alkyl group of C1 to C18, And a silyl group substituted with a C5 or more heterobicyclic group, and Rc and Rd are each independently selected from the group consisting of hydrogen, a C1 to C18 alkyl group, a C1 to C18 alkoxy group, An aromatic group, a substituted or unsubstituted aliphatic cyclic group of C 5 or more, an amine group of C 1 to C 18, an amine group substituted with an aromatic group of C 6 or more, an amine group substituted with a aliphatic cyclic group of C 5 or more, Or it consists of any one selected from the silyl group substituted with a silyl group, C5 or more release ring group substituted with one aromatic group of C6, except the case where Rc and Rd are both hydrogen.

The molar ratio of the ligand to the iridium dimer ([IrL ₂ Cl] ₂ ) connected by the chlorine atom is 1: 2 to 1:80.

The reaction is carried out in a temperature range of 180 to 230 ° C.

The reaction is carried out for 1 to 30 minutes.

In addition, the organic electroluminescent device according to an embodiment of the present invention includes an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode, And the blue phosphorescent compound according to the method.

The blue phosphorescent compound is used as a dopant of the light emitting layer.

The blue phosphorescent compound is doped in the light emitting layer at a weight ratio of 0.1 to 50%.

The method of synthesizing a blue phosphorescent compound according to an embodiment of the present invention uses an microwave to reach an optimum reaction condition in a short time, and since a microwave is utilized as a reaction energy source together with a high temperature reaction state, generation of by- And the synthesis yield of the iridium compound can be improved.

1 is a view illustrating an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, various embodiments of the present invention will be described in detail with reference to the accompanying drawings.

1 is a view illustrating an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent device 100 according to an embodiment of the present invention includes an anode 110, a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, An electron injecting layer 160, and a cathode 170. [0033]

The anode 110 may be any one of indium tin oxide (ITO), indium zinc oxide (IZO), and zinc oxide (ZnO). When the anode 110 is a reflective electrode, the anode 110 may have a reflective layer made of any one of aluminum (Al), silver (Ag), and nickel (Ni) under the layer made of any one of ITO, IZO, .

The hole injection layer 120 may function to smoothly inject holes from the anode 110 into the light emitting layer 140. The hole injection layer 120 may be formed of cupper phthalocyanine (CuPc), poly (3,4) -ethylenedioxythiophene (PEDOT) polyaniline and NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine), but the present invention is not limited thereto.

The thickness of the hole injection layer 120 may be 1 to 150 nm. If the thickness of the hole injection layer 120 is 1 nm or more, the hole injection characteristics can be prevented from being degraded. If the thickness is 150 nm or less, the thickness of the hole injection layer 120 is too thick, There is an advantage that it is possible to prevent the drive voltage from rising.

The hole transport layer 130 plays a role of facilitating the transport of holes and may be formed by using NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine), TPD (N, N'- N, N'-bis- (phenyl) -benzidine), s-TAD, and MTDATA (4,4 ', 4 "-tris (N-3-methylphenyl-N-phenylamino) -triphenylamine) But it is not limited thereto.

The thickness of the hole transport layer 130 may be 1 to 150 nm. Here, if the thickness of the hole transport layer 130 is 5 nm or more, the hole transport property can be prevented from being lowered. If the thickness is 150 nm or less, the thickness of the hole transport layer 130 is too thick, There is an advantage that the driving voltage can be prevented from rising.

The light emitting layer 140 may be formed of a material that emits blue light, and may be formed using a phosphorescent material. In this embodiment, a substance emitting blue light will be described.

The light emitting layer 140 of the present invention may be composed of a blue phosphorescent compound represented by the following general formula (1).

[Chemical Formula 1]

Wherein X ₁ , X ₂ , X ₃ and X ₄ are each independently selected from a nitrogen atom or a carbon atom and A is a 5- to 6-membered nitrogen heteroaromatic group consisting of X ₁ -X ₂ -N Group, and B is a 5- to 6-membered aromatic or heteroaromatic group consisting of CX ₃ -X ₄ . X ₅ -L 1 -X ₆ is a 2-position ligand, X ₅ and X ₆ are each independently selected from a carbon atom, a nitrogen atom or an oxygen atom, and L 1 is an atomic group forming a two-terminal ligand. n is an integer of 1 to 3, a is an integer of 0 to 3, and b is an integer of 0 to 3.

And, Ra and Rb are each independently, hydrogen, D, F, Cl, of Br halogen, CF _3, cyano group, C1 to alkyl groups of C18, C1 to alkoxy groups, C6 or more substituted or unsubstituted aromatic group ring of C18 , A substituted or unsubstituted aliphatic cyclic group of C5 or more, an amine group of C1 to C18, an amine group substituted with an aromatic group of C6 or more, an amine group substituted with a aliphatic cyclic group of C5 or more, an alkyl group of C1 to C18, And a silyl group substituted with a C5 or more heterobicyclic group, and Rc and Rd are each independently selected from the group consisting of hydrogen, a C1 to C18 alkyl group, a C1 to C18 alkoxy group, An aromatic group, a substituted or unsubstituted aliphatic cyclic group of C 5 or more, an amine group of C 1 to C 18, an amine group substituted with an aromatic group of C 6 or more, an amine group substituted with a aliphatic cyclic group of C 5 or more, Or it consists of any one selected from the silyl group substituted with a silyl group, C5 or more release ring group substituted with one aromatic group of C6, except the case where Rc and Rd are both hydrogen.

The iridium compound has largely a facial and meridional stereoisomer, and it is generally known that the hibernation structure is better in luminous efficiency and color. In order to obtain the hibernation structure as the main product in the synthesis process, the reaction should be carried out at a high temperature of 180 ° C or higher. However, when a ligand having a substituent capable of causing steric hindrance to Rc or Rd, such as the compound of the formula (1), is used, a low yield is observed in the conventional synthesis method. Microwave was introduced to improve synthesis yield.

Typical chemical reactions raise the temperature by heating the reaction vessel. In fact, the outer wall of the reaction vessel is higher than the internal temperature and a temperature higher than 180 ° C is applied to the surface, which promotes the production of by-products. This effect becomes greater the higher the reaction temperature. On the other hand, the microwave generates dipole rotation or ionic conduction, so that the optimal reaction condition is reached in a short time without any difference in temperature between the inner wall and the outer wall, and microwave is used as a reaction energy source It is possible to inhibit the formation of by-products generated in the reaction and improve the synthesis yield of the iridium compound. A more detailed synthesis method will be described later.

The blue phosphorescent compound may be used as a dopant of the light emitting layer 140, and the blue phosphorescent compound may be doped to the light emitting layer 140 at a weight ratio of 0.1 to 50%.

The electron transport layer 150 serves to smooth the transport of electrons and is made of at least one selected from the group consisting of Alq3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq, But is not limited thereto.

The thickness of the electron transport layer 150 may be 1 to 50 nm. If the thickness of the electron transporting layer 150 is 1 nm or more, the electron transporting property can be prevented from being degraded. If the thickness is 50 nm or less, the thickness of the electron transporting layer 150 is too thick, There is an advantage that the driving voltage can be prevented from rising.

The electron injection layer 160 serves to smooth the injection of electrons and may include Alq3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq or SAlq.

The thickness of the electron injection layer 160 may be 1 to 50 nm. If the thickness of the electron injection layer 160 is 1 nm or more, there is an advantage that the electron injection characteristics can be prevented from being degraded. If the thickness is 50 nm or less, the thickness of the electron injection layer 150 is too thick, There is an advantage that it is possible to prevent the drive voltage from rising.

The cathode 170 is an electron injection electrode and may be made of magnesium (Mg), calcium (Ca), aluminum (Al), silver (Ag), or an alloy thereof having a low work function. Here, the anode 170 may be formed to have a thickness thin enough to transmit light when the organic electroluminescent device is a front or both-side light emitting structure, and when the organic electroluminescent device is a back light emitting structure, It can be formed thick enough.

Hereinafter, Synthesis Examples and Examples of the blue phosphorescent compound of the present invention will be described in detail in Synthesis Examples and Examples below. However, the following Synthesis Examples and Examples are illustrative of the present invention, and the present invention is not limited to the following Examples.

Example 1: (Ir (tpz) ₃ )

[Ir (tpz) ₂ Cl] ₂ Synthesis of

(Ozone) pyrazole (TPz, 2.2 eq.) And Ir ₃ .3H ₂ O (1 eq.) Were dissolved in a mixed solution of 2-ethoxyethanol and distilled water in a ratio of 3: Lt; / RTI > The reaction mixture was cooled to room temperature and excess distilled water was added. The reaction mixture was filtered under reduced pressure, and washed with distilled water (X3) and hexane (X3). Diethyl ether was added to the precipitate and subjected to sonication for 30 minutes, followed by filtration under reduced pressure to obtain a brown solid.

Synthesis Example 1: Synthesis of iridium complex (Ir (tpz) ₃ )

The earlier synthesis [Ir (tpz) ₂ Cl] into a ₂ (1 eq) and tpz (50 eq.), AgOTf (2.2 equiv.) To a microwave vessel (microwave vessel), the reaction mixture was reacted at 220 ℃ 5 minutes, room temperature , The precipitate which was not soluble with Celite 545 was removed, and the resultant was separated by silica column chromatography (CH ₂ Cl ₂ ). Petroleum ether was added to the separated compound, and the insoluble solid was filtered under reduced pressure to obtain Ir (tpz) ₃ .

Synthesis Example 2: Iridium complex (Ir (tpz) ₃ )

_{[Ir (tpz) 2 Cl]} 2 (1 equivalent), tpz (50 eq.) And K ₂ gu 2 a CO ₃ (10 eq.) Was added to a round bottom flask (2-neck round flask), and the reaction mixture at 220 ℃ After reacting for 24 hours, the temperature was lowered to room temperature, the precipitate which was not soluble with Celite 545 was removed, and the reaction product was separated by silica column chromatography (CH ₂ Cl ₂ ). Petroleum ether was added to the separated compound, and the insoluble solid was filtered under reduced pressure to obtain Ir (tpz) ₃ .

Synthesis Example 3: IrCl ₃ The iridium complex (Ir (tpz) ₃ )

After gave IrCl ₃ and 3 (H ₂ O) (1 eq.), Place the tpz (50 equiv.) And AgOTf (3.1 equiv.) In a microwave vessel, the reaction mixture was reacted at 220 ℃ 5 minutes, lowering the temperature to room temperature, The precipitate that did not dissolve with Celite 545 was removed and separated by silica column chromatography (CH ₂ Cl ₂ ). Petroleum ether was added to the separated compound, and the insoluble solid was filtered under reduced pressure to obtain Ir (tpz) ₃ .

The following Table 1 shows the results of synthesizing iridium compounds by substituting the ligands tpz with ppz in the foregoing Synthesis Examples 1 to 3 and varying the ligand equivalence, the base source, the base equivalent, the solvent and the reaction time The reaction yield was shown. In the following Table 1, MV represents a microwave reaction and Heat represents a thermal reaction. Ir dimer is the [Ir (tpz) ₂ Cl] ₂ described above, and Neat represents a solvent-free reaction.

# division Ir source Ligand Ligand equivalent base source base equivalent Solvent Reaction time reaction
Yield One MW IrCl ₃ TPz 50 AgOTf 3.1 Neat 5min / 2 MW Ir dimer TPz 50 AgOTf 2.2 Neat 5min 38% 3 MW Ir dimer TPz 50 AgOTf 2.2 Neat 10 min 43% 4 HEAT Ir dimer TPz 50 K ₂ CO ₃ 10 Neat 2day 40% 5 HEAT Ir dimer TPz 2.4 K ₂ CO ₃ 10 glycerol 2day 11% 6 HEAT IrCl ₃ ppz 3.6 AgOTf 3.1 glycerol 2day / 7 MW Ir dimer ppz 50 AgOTf 2.2 Neat 5min 69% 8 MW Ir dimer ppz 50 AgOTf 2.2 Neat 10 min 62% 9 HEAT Ir dimer ppz 2.4 K ₂ CO ₃ 10 glycerol 2day 70%

Referring to Table 1 above, tpz capable of causing steric hindrance and ppz having no steric hindrance were used as ligands. In the case of Ir (ppz) ₃ without steric hindrance, high synthesis yields of 60% or more were obtained regardless of MW and heat. In the case of Ir (tpz) ₃ with impairment, a thermal reaction using an organic solvent (# 5) yielded a low yield of 11%. When excess ligand (tpz) %, But the reaction time was longer than 2 days. When the reaction was conducted using microwaves (# 3, # 4), the synthesis yields of 38 to 43% were confirmed during a short reaction time of 5 minutes and 10 minutes.

Therefore, in the case of Examples 2, 3, 7 and 8 in which an iridium compound was synthesized through a microwave reaction, it was confirmed that the reaction time was greatly reduced to within 10 minutes as compared with the thermal reaction.

Example 2: (Ir (p (bp) pz) ₃ )

Synthesis Example 4: Synthesis of iridium complex (Ir (tpz) ₃ )

[Ir (p (bp) pz ) 2 Cl] 2 (1 equivalent), p (bp) pz (50 eq.) And insert the AgOTf (2.2 equiv.) In a microwave vessel, the reaction mixture was reacted at 220 ℃ 5 minutes. After lowering the temperature to room temperature, the precipitate which did not dissolve with Celite 545 was removed and separated by silica column chromatography (CH ₂ Cl ₂ ). Petroleum ether was added to the separated compound, and the insoluble solid was filtered under reduced pressure to obtain (Ir (tpz) ₃ ).

Synthesis Example 5: Synthesis of Ir (acac) ₃ The iridium complex (Ir (tpz) ₃ )

Compound p (bp) pz (4.5 equivalents) and Iridium (III) acetylacetonate (1 equivalent) were added to a 25 ml round bottom flask and the reaction mixture was vacuum dried for 30 minutes and the reaction flask was filled with nitrogen gas Repeat) ethylene glycol to the reaction mixture (ethylene glycol) insert after 48 hours at 200 ℃, and after semi lowering the temperature to room temperature, remove the precipitate insoluble in celite 545, and the silica and purified by column chromatography with (CH ₂ Cl ₂ ). Petroleum ether was added to the separated compound, and the insoluble solid was filtered under reduced pressure to obtain (Ir (tpz) ₃ ).

The following Table 2 shows the synthesis yields of the iridium compounds synthesized according to Synthesis Examples 4 and 5 described above. Synthetic Example 4 is shown in # 10 and Synthesis Example 4 is shown in # 11 using thermal reaction instead of microwave. , And Synthesis Example 5 is shown in # 12. Ir dimer represents [Ir (p (bp) pz) ₂ Cl] ₂ .

# division Ir source Ligand Ligand equivalent base source base equivalent Solvent reaction
time reaction
Yield 10 MW Ir dimer p (bp) pz 50 AgOTf 2.2 Neat 10 min 33% 11 Heat Ir dimer p (bp) pz 50 K ₂ CO ₃ 10 Neat 2day 17% 12 Heat Ir (acac) ₃ p (bp) pz 4.5   X   X Ethylene Glycol 2day 5%

Referring to Table 2 above, the synthesis yield of 33% when using microwaves (# 10) was confirmed. However, as a result of the thermal reaction without microwave, the synthesis yields were different according to the Ir source, but the synthesis yields were very low, ie, 17% (# 1113) for IrCl ₃ and 5% for Ir (acac) ₃ (# 12). Compared with Ir (tpz) ₃ and Ir (ppz) ₃ , Ir (p (bp) pz) ₃ has a biphenyl group with larger steric hindrance.

As described above, in the method of synthesizing a blue phosphorescent compound according to an embodiment of the present invention, an optimal reaction condition is reached in a short time using a microwave, and since a microwave is utilized as a reaction energy source together with a high temperature reaction state, And the synthesis yield of the iridium compound can be improved.

While the present invention has been described in connection with what is presently considered to be practical exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It will be understood that the invention may be practiced. It is therefore to be understood that the embodiments described above are to be considered in all respects only as illustrative and not restrictive. In addition, the scope of the present invention is indicated by the following claims rather than the detailed description. Also, all changes or modifications derived from the meaning and scope of the claims and their equivalents should be construed as being included within the scope of the present invention.

100: organic electroluminescent device 110: anode
120: Hole injection layer 130: Hole transport layer
140: light emitting layer 150: electron transporting layer
160: electron injection layer 170: cathode

Claims (7)

The blue phosphorescent compound represented by the following general formula (1)
The concentration of the iridium dimer ([IrL ₂ Cl] ₂ ) and the ligand connected by the chlorine atom is 2 to 100 times higher than the concentration of the iridium reactant by using microwave under the temperature range of 100 to 300 ° C for 1 minute to 10 hours Lt; RTI ID = 0.0 > phosphorescent < / RTI >
[Chemical Formula 1]

Wherein X ₁ , X ₂ , X ₃ and X ₄ are each independently selected from a nitrogen atom or a carbon atom and A is a 5- to 6-membered nitrogen heteroaromatic group consisting of X ₁ -X ₂ -N Group, and B is a 5- to 6-membered aromatic or heteroaromatic group consisting of CX ₃ -X ₄ . X ₅ -L 1 -X ₆ is a 2-position ligand, X ₅ and X ₆ are each independently selected from a carbon atom, a nitrogen atom or an oxygen atom, and L 1 is an atomic group forming a two-terminal ligand. n is an integer of 1 to 3, a is an integer of 0 to 3, and b is an integer of 0 to 3.
And, Ra and Rb are each independently, hydrogen, D, F, Cl, of Br halogen, CF _3, cyano group, C1 to alkyl groups of C18, C1 to alkoxy groups, C6 or more substituted or unsubstituted aromatic group ring of C18 , A substituted or unsubstituted aliphatic cyclic group of C5 or more, an amine group of C1 to C18, an amine group substituted with an aromatic group of C6 or more, an amine group substituted with a aliphatic cyclic group of C5 or more, an alkyl group of C1 to C18, And a silyl group substituted with a C5 or more heterobicyclic group, and Rc and Rd are each independently selected from the group consisting of hydrogen, a C1 to C18 alkyl group, a C1 to C18 alkoxy group, An aromatic group, a substituted or unsubstituted aliphatic cyclic group of C 5 or more, an amine group of C 1 to C 18, an amine group substituted with an aromatic group of C 6 or more, an amine group substituted with a aliphatic cyclic group of C 5 or more, Or it consists of any one selected from the silyl group substituted with a silyl group, C5 or more release ring group substituted with one aromatic group of C6, except the case where Rc and Rd are both hydrogen.
The method according to claim 1,
Wherein the molar ratio of the iridium dimer ([IrL ₂ Cl] ₂ ) connected with the chlorine atom to the ligand is 1: 2 to 1: 80.
The method according to claim 1,
Wherein the reaction is carried out at a temperature ranging from 180 to 230 < 0 > C.
The method according to claim 1,
Wherein the reaction is carried out for 1 to 30 minutes.
In an organic electroluminescent device comprising an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode,
Wherein the light emitting layer comprises the blue phosphorescent compound according to the manufacturing method of any one of claims 1 to 4.
6. The method of claim 5,
Wherein the blue phosphorescent compound is used as a dopant of the light emitting layer.
The method according to claim 6,
And the blue phosphorescent compound is doped in the light emitting layer at a weight ratio of 0.1 to 50%.

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