KR101521483B1 - Boron complex for electroluminescent materials, method for preparing the same and organic light emitting diode comprising the same - Google Patents

Abstract

The present invention relates to a boron complex compound for an organic electroluminescent layer material, a method for producing the same, and an organic electroluminescent diode including the same. The boron complexes of the present invention exhibit excellent optical properties such as thermal stability, color purity and luminescence efficiency, and thus can be very usefully used as a red dopant of a light emitting layer in an OLED device.

Description

Technical Field The present invention relates to a boron complex compound for an organic electroluminescent layer material, a method for producing the same, and an organic electroluminescent diode including the same.

The present invention relates to a boron complex compound for an organic electroluminescent layer material, a method for producing the same, and an organic electroluminescent diode including the same.

Recently, a mobile phone, a TV, or a lighting device using the organic light emitting diode (OLED) has been developed in accordance with the remarkable development of an organic light emitting diode (OLED). In these electronic products, OLED devices are also a key part of the overall product quality. The criteria for the basic performance of the OLED device include driving voltage, power consumption, efficiency, brightness, contrast, response time, lifetime, color coordinates, and color purity. In general, an OLED is composed of an organic layer between a cathode and an anode, as shown in FIG. 1. The basic structure and operating principle of the OLED, the characteristics and requirements of the core organic material are described in " Physics and Advanced Technology, april 2005, pp 18-24 , Park Jong-wook ".

As shown in FIG. 1, the organic light emitting diode device includes a transparent ITO anode, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EL), a hole blocking layer (HBL) ETL), an electron injection layer (EIL), lithium or aluminum, but one or two organic layers such as a hole blocking layer may be omitted, if necessary. When a voltage is applied to both electrodes of the device, electrons are injected from the cathode to the electron injection layer, and holes are injected from the anode to the hole injection layer. The injected holes and electrons move to the light emitting layer through the electron transport layer and the hole transport layer, recombine to form an excited state, and return energy from the excited state to the ground state as much as the energy difference between the excited state and the ground state. . In the above structure, the light emitting layer is composed of a single material or two materials composed of a host / dopant system. The host / dopant system controls quantum efficiency and emission wavelength to improve color purity and the like This is a method that is widely adopted in device fabrication recently. The material of such a light emitting layer is roughly classified into fluorescence and phosphorescence. There are a method of doping phosphors (dopants) to phosphors (host), a method of increasing quantum efficiency by doping phosphors (dopants) (DCM, Rubrene, DCJTB or the like) is used to shift the emission wavelength. Attempts have been made to improve the emission wavelength, efficiency, driving voltage, lifetime and the like through such doping. On the other hand, in the above structure, the dopant layer emits light again and does not emit light. However, the emissive dopant (emitting layer) functioning to enhance the light efficiency and color purity of the emission spectrum by assisting energy transfer from the host to the dopant, assist dopant. Materials and OLED asymmetric materials are listed below for high efficiency emission efficiency of OLED devices.

Generally, materials for forming the light emitting layer have a structure such as anthracene, pyrene, fluorene, and spiropro lrene. The invention of a pyrene structure having an asymmetric structure according to the prior invention is disclosed in Korean Patent Application Nos. 10-2012-0128386, 10-2006-7024933, 10-2008-0133717, 10-2009-0071884, and 10-2009-0124172 And anthracene structures are described in Korean Patent Application Nos. 2010-7009408, 10-2008-0068226, 10-2008-0044369, 10-2007-009819, 10-2007-0019149, and 10-2007-0009973, Rhen structures are described in Korean Patent Application Nos. 2008-0049927, 10-2009-7009883, 10-2005-7013051, 10-2006-7010637, 10-2007-0008160, 10-2007-7015342 and 10-2008-0011491 have.

Also, a pyran-based compound having the following structure as a red fluorescent material (dopant) of an OLED is disclosed in J. Appl. Phys. 65, 1989.

In the meantime, Giselle et al. Have shown the possibility of using a boron complex (BODITERPY) as a dopant of an OLED light-emitting layer in the following documents (Synth. Met. Vol 146, 2004, pp11-15; Tetrahedron, Vol 67 ).

However, the above-mentioned conventional light emitting materials still have problems in terms of thermal stability and light stability, and are not satisfactory in terms of color purity and efficiency. Therefore, there is a desperate need for continuous research on these light emitting materials have.

The present inventors have completed the present invention by confirming compounds exhibiting excellent properties in terms of heat stability, color purity and efficiency, while conducting studies for synthesizing various boron complexes (BODIPY) derivatives and using them as dopants for OLED light emitting layers.

Accordingly, the present invention provides a boron complex compound for an organic electroluminescent layer material, a method for producing the same, and an organic electroluminescent diode including the same.

The present invention provides a boron complex compound for an organic electroluminescent layer material, a method for producing the same, and an organic electroluminescent diode including the same.

The boron complexes of the present invention exhibit excellent optical properties such as thermal stability, color purity and luminescence efficiency, and thus can be very usefully used as a red dopant of a light emitting layer in an OLED device.

1 is a schematic diagram showing a basic structure of an OLED light emitting device.
2 is a graph showing the ¹ H NMR spectrum of the compound of Formula 1-1.
Fig. 3 is a diagram showing the absorption spectrum of the compound of formula 1-1. Fig.
4 is a diagram showing the emission spectrum of the compound of the formula 1-1.
FIG. 5 is a graph showing the ¹ H NMR spectrum of the compound of Formula 1-2. FIG.
Fig. 6 is a diagram showing the absorption spectrum of the compound of the formula 1-2. Fig.
7 is a diagram showing the luminescence spectrum of the compound of the formula 1-2.
8 is a diagram showing the emission spectra of the compound of the formula 1-1, the compound of the formula 1-2 and AlQ ₃ .

The present invention provides a boron complex compound represented by formula (1);

[Chemical Formula 1]

In Formula 1,

R _1, R ₂ and R ₃ are each different and the same or independently, a H, C ₁ -C ₂₀ alkyl, hydroxy, a halogen, C ₁ -C ₂₀ alkoxy, C ₆ -C ₃₀ aryl, C ₁ - An alkylthio group of C ₂₀ , and an arylthio group of C ₆ -C ₃₀ ,

L ₁ , L ₂ and L ₃ represent a single bond connecting the ortho positions of the respective aryl groups to each other, which may or may not be present independently of each other,

n and m are each independently an integer of 0 to 30;

It is preferable that the boron complexing chemical represented by the above formula (1) is a compound represented by any of the following formulas (1-1) to (1-6).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

In addition,

1) reacting a compound of the formula 1-a and ethynyltrimethylsilane with CuI and Pd (PPh ₃ ) ₂ Cl ₂ in an organic solvent to obtain a compound of the formula 1-b;

2) reacting a compound of formula (I-b) with a mixed solution of KOH and MeOH in an organic solvent to obtain a compound of formula (I-c);

3) reacting the compound of formula 1-c and 2- (4-iodo-phenyl) -5,5-dimethyl- [1,3] dioxane with CuI and Pd (PPh ₃ ) ₂ Cl ₂ in an organic solvent To obtain a compound of formula (I-d);

4) reacting the compound of formula (I-d) with trifluoroacetic acid and water in an organic solvent to obtain the compound of formula (I-e); And

5) To 2,4-dimethyl-3-ethyl-1H-pyrrole and trifluoroacetic acid were added to the compound of the formula (I-e) in an organic solvent and stirred, and 2,3-dichloro-5,6-dicyano- , 4-benzoquinone, and BF ₃ to obtain a compound of formula (1);

And a method for producing the boron complex compound represented by the following reaction formula (1).

[Reaction Scheme 1]

In the above Reaction Scheme 1,

R ₁ , R ₂ , R ₃ , L ₁ , L ₂ , L ₃ , n and m are as defined in the above formula (1).

Hereinafter, a method for preparing the boron complex of the present invention will be described in detail.

In step 1) , CuI and Pd (PPh ₃ ) ₂ Cl ₂ are added to the compound of formula (I-a ) in the first sonogashira coupling reaction, and then ethynyltrimethylsilane is added. Thereafter, the mixture is stirred for 6 to 10 hours while maintaining the temperature at 40 to 50 ° C. After stirring, the solution is cooled and filtered to obtain the compound of formula (I-b).

Step 2) is a step of deprotecting the trimethylsilyl protecting group to slowly add a mixed solution of KOH and MeOH to an organic solvent in which the compound of the formula (1-b) is dissolved and stirring at room temperature for 30 minutes to 2 hours to obtain Compound.

Step 3) is a second sonogashira coupling reaction in which CuI and Pd (PPh ₃ ) ₂ Cl _{2 are added} to the compound of formula 1-c and then 2- (4-iodo-phenyl) -5,5-dimethyl - [1,3] dioxane. Thereafter, the mixture is stirred for 6 to 10 hours while maintaining the temperature at 40 to 50 ° C. After stirring, the solution is cooled and filtered to obtain the compound of formula (I-d).

Step 4) is an acetal deprotection reaction. The compound of formula (I-d) is added to an organic solvent, trifluoroacetic acid is added, the mixture is heated to 60 to 80 ° C and stirred for 1 hour to obtain a compound of formula .

In step 5) , the compound of formula (I-e) is dissolved in an organic solvent by a cyclization reaction, a DDQ oxidation reaction, and a BF ₃ complexation reaction. Then, 2,4-dimethyl- The roset acid is added and stirred for 10 hours. Thereafter, 2,3-dicloro-5,6-dicyano-1,4-benzoquinone (DDQ) is added and stirring is performed for 1 to 5 hours, BF ₃ and triethylamine are added and the mixture is stirred for 8 to 15 hours, 1-1.

The organic solvent used in the steps 1) to 5) may be at least one selected from the group consisting of tetrachloroethane, dimethylacetamide, triethylamine, dimethylformamide, chloroform, methylene chloride, ethyl acetate, methanol, hexane, acetonitrile, toluene, , Pentane, acetone, dimethyl sulfoxide, tetrahydrofuran, or dimethyl formaldehyde.

In addition,

A dopant comprising the compound of Formula 1; And

And an organic light-emitting diode light-emitting layer.

The amount of the dopant containing the compound of Formula 1 is preferably 0.01 to 20% by weight based on the total weight of the composition.

In addition to the dopant of the light emitting layer, an emission assist dopant may be used to improve light efficiency and color purity.

Thus, the dopant may be a dopant that additionally includes a luminescent assist dopant that assists energy transfer from the host to the dopant.

The content of the light-emitting assistant dopant is preferably 0.01 to 50% by weight based on the total weight of the composition.

The boron complex compound of the present invention can be used as a dopant material of a light emitting layer composed of a host / dopant of an organic light emitting diode device used for display, illumination, electronic paper and the like. In this system, organic compounds having various structures having AlQ ₃ or a derivative thereof and a fluorene group can be used as the host, and not only are they excellent in light emission characteristics such as color purity and efficiency, but also are not specific to the host used, Can be combined with. Therefore, the present invention is not limited to the type of host used.

In addition,

a) a substrate;

b) an ITO cathode (anode) disposed on the substrate;

c) a hole injection layer disposed on the cathode (anode);

d) a hole transport layer disposed on the hole injection layer;

e) an emission layer disposed directly above the hole transport layer;

f) an electron transport layer disposed on the light emitting layer;

g) an electron injection layer disposed on the electron transport layer; And

h) an anode (cathode) disposed on the electron injection layer,

E) the light emitting layer comprises a dopant comprising the compound of Formula 1; And an organic light emitting diode (OLED) element, wherein the organic light emitting diode (OLED) comprises a host and a composition for an organic light emitting diode light emitting layer.

When the boron complex compound according to the present invention is used as a light emitting layer material in an OLED device, it is possible to manufacture a device having excellent thermal stability, long lifetime, and excellent color purity and luminous efficiency. Such a light emitting layer device provides a core part of many electric / electronic products such as a display, an electronic paper, a lighting device and the like.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited by the examples.

Example 1. Preparation of the compound of the formula 1-1

[Formula 1-1]

1-1. Preparation of N, N-diphenyl-4 - [(trimethylsilyl) ethynyl] aniline

CuI (0.0251 g, 0.135 mmol) was added to a solution of tetrahydrofuran (THF) / triethylamine (TEA) (1: 1) in which N, N-diphenyl-4-iodophenyl aniline (1 g, 2.7 mmol) And 0.094 g (0.135 mmol) of palladium triphenylphosphine dichloride (Pd (PPh ₃ ) ₂ Cl ₂ ) were added, followed by ethynyltrimethylsilane (0.26 g, 2.7 mmol). The mixture was stirred for 8 hours while maintaining the temperature at 45 캜. After stirring, the solution was cooled and filtered to obtain a black solid product, N, N-diphenyl-4 - [(trimethylsilyl) ethynyl] aniline (0.89 g, yield: 97%).

¹ H NMR (chloroform-d ₁ )? 0.24 (s, 9H), 6.92 (m, 2H), 7.09 (m, 6H), 7.28 (m, 6H)

1-2. Preparation of N, N-diphenyl-4-ethynyl aniline

A solution of KOH / MeOH (0.164 g / 2 ml) was added to a THF solution prepared by dissolving N, N-diphenyl-4 - [(trimethylsilyl) ethynyl] aniline (1 g, 2.94 mmol) The mixture was slowly added dropwise using a dropping funnel and stirred at room temperature for 1 hour. The solvent was concentrated under reduced pressure to obtain a black solid product, N, N-diphenyl-4-ethynylaniline (0.65 g, yield: 78%).

_{^{1 H NMR (chloroform-d 1}} ) δ 3.06 (s, 1H), 7.03 (m, 2H), 7.12 (m, 6H), 7.32 (m, 6H) ppm.

1-3. Preparation of N, N-diphenyl- {4- [4- (5,5-dimethyl- [1,3] dioxan-2-yl) -phenylethynyl] phenyl} aniline.

CuI (0.0251 g, 0.135 mmol) and Pd (0.15 mmol) were added to a THF / TEA (1: 1) solution prepared by dissolving N, N-diphenyl-4-ethynylaniline (PPh ₃ ) ₂ Cl ₂ (0.094 g, 0.135 mmol) was added followed by 2- (4-iodo-phenyl) -5,5-dimethyl- [1,3] dioxane (0.86 g, 3.74 mmol) Followed by stirring for 8 hours while maintaining the temperature at 45 ° C. After stirring, the mixture was separated and purified by chromatography (n-hexane: dichloromethane = 4: 1 (v / v)) to obtain a dark green solid product N, N-diphenyl- {4- [4- (5,5- - [1,3] dioxan-2-yl) -phenylethynyl] phenyl} aniline (0.99 g, yield: 58%).

¹ H NMR (chloroform-d ₁ )? 0.79-0.86 (m, 3H), 1.20-1.28 (m, 3H), 3.66-3.78 (m, 4H), 5.38 10H) ppm.

1-4. (4-ethynyl-N, N-diphenyl aniline) -benzoaldehyde.

Phenyl] ethan yl] phenyl} aniline prepared in the above 1-3 (1 g (0.15 mmol)) and N, N-diphenyl- {4- [4- , 2.1 mmol) was added to 20 ml of THF, trifluoroacetic acid was added, and the mixture was heated to 70 占 폚 and stirred for 1 hour. After stirring, the mixture was separated and purified by chromatography (n-hexane: dichloromethane = 4: 1 (v / v)) to obtain pale green solid product (4-ethynyl-N, N-diphenyl aniline) 0.65 g, yield: 78%).

¹ H NMR (chloroform-d ₁ )? 0.80-0.84 (t, 2H), 1.24-1.28 (d, J = 5 Hz, 2H), 3.65-3.80 (d, J = 10 Hz, 4H), 5.44 , 2H), 6.92-7.25 (m, 4H), 7.66-7.91 (m, 8H), 10.01 (s, 1H) ppm.

1-5. Preparation of the compound of formula 1-1.

(4-ethynyl-N, N-diphenyl aniline) -benzoaldehyde (0.2 g, 0.536 mmol) prepared in 1-4 above was dissolved in dichloromethane and then 2,4- Pyrrole (0.15 ml, 1.304 mmol) was added, followed by 3 drops of trifluoroacetic acid and stirring for 10 hours. Then, 2,3-dicyclo-5,6-dicyano-1,4-benzoquinone (DDQ) was added thereto, followed by stirring for 3 hours. BF ₃ (2 ml) and triethylamine (10 ml) (0.22 g, yield: 66%) as a red solid product.

The ¹ H NMR spectrum, the absorption spectrum and the emission spectrum of the compound of the formula (1-1) are shown in FIG. 2 to FIG. 4, respectively.

As shown in FIG. 3, the absorption spectrum of the compound of Formula 1-1 showed the best absorption at 524 nm, and the absorbance corresponds to the HOMO-LUMO band gap energy of the dopant.

As shown in FIG. 4, the luminescence spectrum showed the best luminescence at 551 nm. The luminescent characteristics determine the color purity, which is very close to an ideal green light source (545 nm).

_{^{1 H NMR (chloroform-d 1}} ) δ 0.86-0.99 (m, 6H), 1.24-1.55 (m, 6H), 2.30-2.54 (m, 8H), 7.25-7.45 (d, J = 8.71 Hz, 2H) , 7.60-7.62 (d, J = 8.25 Hz, 2H), 7.78-7.80 (d, J = 8.71 Hz, 2H) ppm.

Example 2. Preparation of the compound of the formula 1-2.

[Formula 1-2]

2-1. Preparation of 9- (4-iodophenyl) carbazole.

Butoxide (0.05 g, 10 mmol) and CuI (0.0251 g, 10 mmol) in toluene (20 mL) in which carbazole (2 g, 5.9 mmol) g, 0.135 mmol), and 1,4-iodobenzene was slowly added thereto and stirred. After stirring for 6 hours, filter paper and diatomaceous earth were placed in a Buchner funnel, filtered and concentrated under reduced pressure. Ethanol was added to the concentrated solution and stirred to produce a solid. The resulting solid was filtered and dried at 60 ° C to obtain 0.87 g (yield: 40%) of 9- (4-iodophenyl) carbazole as a white solid.

¹ H NMR (chloroform-d ₁ )? 7.24-7.24 (dd, J = 5 Hz, 2H), 7.27-7.30 (m, 4H), 7.33-7.34 (m, 4H) ppm.

2-2. Preparation of 9- (4-trimethylsilylethynylphenyl) carbazole.

A solution of CuI (0.0251 g, 0.135 mmol) and Pd (PPh ₃ ) was added to a solution of 9- (4-iodophenyl) carbazole (1 g, 2.7 mmol) prepared in the above 2-1 in THF / TEA ) ₂ Cl ₂ (0.094 g, 0.135 mmol) was added, followed by ethynyltrimethylsilane (0.26 g, 2.7 mmol). The mixture was stirred for 8 hours while maintaining the temperature at 45 ° C. After stirring, the solution was cooled and filtered to obtain a black solid product, 9- (4-trimethylsilylethynylphenyl) carbazole (0.89 g, yield: 97%).

_{^{1 H NMR (chloroform-d 1}} ) δ 0.31 (s, 9H), 7.34-7.28 (m, 2H), 7.43-7.40 (m, 4H), 7.56-7.51 (m, 2H), 7.73-7.69 (m, 2H), 8.17-8.12 (m, 2H) ppm.

2-3. Preparation of 9- (4-ethynylphenyl) carbazole.

To the THF solution in which the 9- (4-trimethylsilylethynylphenyl) carbazole (1 g, 2.94 mmol) prepared in the above 2-2 was dissolved, KOH / MeOH (0.164 g / 2 ml) solution was slowly added dropwise using a drop funnel And the mixture was stirred at room temperature for 1 hour. The solvent was concentrated under reduced pressure to obtain 0.73 g (yield: 94%) of 9- (4-ethynylphenyl) carbazole as a black solid product.

_{^{1 H NMR (chloroform-d 1}} ) δ 3.19 (s, 1H), 7.33-7.29 (m, 2H), 7.44-7.42 (m, 4H), 7.57-7.55 (m, 2H), 7.75-7.73 (m, 2H), 8.17-8.14 (m, 2H) ppm.

2-4. Preparation of 9- {4- [4- (5,5-dimethyl- [1,3] dioxan-2-yl) -phenylethynyl] -phenyl} carbazole.

To a solution of 9- (4-ethynylphenyl) carbazole (1 g, 3.74 mmol) prepared in 2-3 above in THF / TEA (1: 1) solution dissolved CuI (0.0251 g, 0.135 mmol) and Pd ₃ ) ₂ Cl ₂ (0.094 g, 0.135 mmol) was added and then 2- (4-iodo-phenyl) -5,5-dimethyl- [1,3] dioxane (0.86 g, 3.74 mmol) Lt; 0 > C and stirred for 8 hours. After stirring, the mixture was separated and purified by chromatography (n-hexane: dichloromethane = 4: 1 (v / v)) to obtain an orange solid product, 9- {4- [4- (5,5- ] Dioxan-2-yl) -phenylethynyl] -phenyl} carbazole (yield: 58%).

_{^{1 H NMR (chloroform-d 1}} ) δ 0.82 (s, 3H), 1.24-1.30 (m, 3H), 3.68-3.77 (d, J = 4.5 Hz, 4H), 5.41 (s, 1H), 7.21-7.57 (m, 10H), 8.12-8.14 (d, J = 10 Hz, 2H) ppm.

2-5. Preparation of 4- (4-carbazol-9-yl-phenylethynyl) -benzaldehyde.

Phenylethynyl] -phenyl} carbazole (1 g, 2.09 mmol), prepared in 2-4 above, was added dropwise to a solution of 9- {4- [4- (5,5-dimethyl- [1,3] dioxan- Was added to 20 ml of THF, and trifluoroacetic acid (10 ml) and H ₂ O (15 ml) were added. The mixture was heated to 70 ° C and stirred for one hour. After stirring, the mixture was separated and purified by chromatography (n-hexane: dichloromethane = 4: 1 (v / v)) to obtain 4- (4-carbazol-9-yl- phenylethynyl) -benzaldehyde (0.65 g, yield: 78%).

_{^{1 H NMR (chloroform-d 1}} ) δ 7.21-7.32 (m, 6H), 7.40-7.81 (m, 6H), 7.89-7.92 (d, J = 10 Hz, 2H), 8.13-8.15 (d, J = 10 Hz, 2H), 10.04 (s, 1H) ppm.

2-6. Preparation of compounds of general formula 1-2.

4- (4-carbazol-9-yl-phenylethynyl) -benzaldehyde (0.2 g, 0.539 mmol) prepared in 2-5 above was dissolved in dichloromethane and 2,4-dimethyl- Pyrrole (0.15 ml, 1.304 mmol) was added, and 3 drops of trifluoroacetic acid was added, followed by stirring for 10 hours. After adding DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) to the solution and stirring for 3 hours, 10 ml of BF ₃ and triethylamine (TEA) To obtain a red compound (1-22 g, yield: 68%).

The ¹ H NMR spectrum, the absorption spectrum and the emission spectrum of the compound of the formula (1-2) are shown in FIGS. 5 to 7, respectively.

As shown in FIG. 6, the absorption spectra of the compound of Formula 1-2 showed the best absorption at 526 nm, and the absorption spectrum of the dopant was related to the energy transfer efficiency between the host and dopant (guest) It can be seen that it matches well with a host emitting a wavelength around 520 nm.

As shown in FIG. 7, the luminescence spectrum showed the best luminescence at 552 nm. The luminescent characteristics determine the color purity, which is very close to an ideal green light source (545 nm).

¹ H NMR (chloroform-d ₁ )? 0.82-1.55 (m, 6H), 2.15-2.51 (m, 6H), 3.68-3.83 7.63 (m, 8 H) ppm.

8 shows the emission spectra of the compound of the formula 1-1, the compound of the formula 1-2 and the AlQ ₃ used as the host.

As shown in FIG. 8, the luminescence spectra of the compounds of formulas (1-1) and (1-2) significantly overlap with the luminescence spectrum of AlQ ₃ , indicating that the energy transfer between the dopant and the host occurs well.

Claims (10)

delete A boron complex compound represented by the formula (1-1) or (1-2).
[Formula 1-1]

[Formula 1-2]

1) reacting a compound of the formula 1-a and ethynyltrimethylsilane with CuI and Pd (PPh ₃ ) ₂ Cl ₂ in an organic solvent to obtain a compound of the formula 1-b;
2) reacting a compound of formula (I-b) with a mixed solution of KOH and MeOH in an organic solvent to obtain a compound of formula (I-c);
3) reacting the compound of formula 1-c and 2- (4-iodo-phenyl) -5,5-dimethyl- [1,3] dioxane with CuI and Pd (PPh ₃ ) ₂ Cl ₂ in an organic solvent To obtain a compound of formula (I-d);
4) reacting the compound of formula (I-d) with trifluoroacetic acid and water in an organic solvent to obtain the compound of formula (I-e); And
5) To 2,4-dimethyl-3-ethyl-1H-pyrrole and trifluoroacetic acid were added to the compound of the formula (I-e) in an organic solvent and stirred, and 2,3-dichloro-5,6-dicyano- , 4-benzoquinone and BF ₃ to obtain a compound of the following formula 1-1 or 1-2:
And a method for producing the boron complex represented by the following Reaction Scheme 1:
[Reaction Scheme 1]

In the above Reaction Scheme 1,
R ₁ , R ₂ and R ₃ are aryl groups,
L ₁ , L ₂ and L ₃ represent a single bond connecting the ortho positions of the respective aryl groups to each other,
n and m are integers of 1.
[Formula 1-1]

[Formula 1-2]

4. The method of claim 3, wherein the organic solvent is selected from the group consisting of tetrachloroethane, dimethylacetamide, triethylamine, dimethylformamide, chloroform, methylene chloride, ethyl acetate, methanol, hexane, acetonitrile, toluene, benzene, , Dimethylsulfoxide, tetrahydrofuran, or dimethylformaldehyde. The method for producing a boron complex compound according to claim 1, A dopant comprising a compound of formula 1-1 or 1-2; And a host, wherein the composition for organic light emitting diode light emitting layer comprises:
[Formula 1-1]

[Formula 1-2]

6. The composition for an organic light emitting diode light emitting layer according to claim 5, wherein the dopant comprising the compound of Formula 1-1 or 1-2 is present in an amount of 0.01 to 20% by weight based on the total weight of the composition. The composition for an organic light emitting diode light emitting layer according to claim 5, wherein the dopant is a dopant additionally comprising a light emitting assistant dopant for facilitating energy transfer from the host to the dopant. 8. The composition for an organic light emitting diode light emitting layer according to claim 7, wherein the content of the light emitting assistant dopant is 0.01 to 50% by weight based on the total weight of the composition. The composition for an organic light emitting diode light emitting layer according to claim 5, wherein the host is selected from AlQ ₃ or a derivative thereof, or an organic compound having a fluorene group. a) a substrate;
b) an ITO cathode (anode) disposed on the substrate;
c) a hole injection layer disposed on the cathode (anode);
d) a hole transport layer disposed on the hole injection layer;
e) an emission layer disposed directly above the hole transport layer;
f) an electron transport layer disposed on the light emitting layer;
g) an electron injection layer disposed on the electron transport layer; And
h) an anode (cathode) disposed on the electron injection layer,
E) the light emitting layer comprises a dopant comprising a compound of the following general formula 1-1 or 1-2; And an organic light emitting diode (OLED) element, wherein the organic light emitting diode (OLED)
[Formula 1-1]

[Formula 1-2]

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