KR20150131807A - Dye comprising pyrromethene boron complex compound - Google Patents

Abstract

The present invention relates to a dye comprising a pyrromethene boron complex compound. The dye comprising a pyrromethene boron complex according to the present invention does not have fluorescence, has excellent light resistance, and absorbs light of a specific wavelength, thereby being used as a display dye.

Description

[0001] DYE COMPRISING PYRROMETHENE BORON COMPLEX COMPOUND [0002]

The present invention relates to a dye containing a novel pyromethene boron complex, and more particularly to a dye for display comprising a pyromethene boron complex capable of absorbing light having a specific wavelength, which is excellent in light resistance and has no fluorescence .

2. Description of the Related Art Flat panel displays such as a liquid crystal display (LCD), a plasma display (PDP), and an organic light emitting diode (OLED) are now widely used as household / industrial displays for television, mobile phones and personal computers.

Since a liquid crystal display (LCD) widely used as a flat panel display is a light-receiving device that displays an image by controlling the amount of light coming from the outside, a backlight unit of a backlight type capable of maintaining uniform brightness over the entire screen BLU: Back Light Unit) is required.

A backlight unit is a device that can display information by supplying lamp light to an LCD that can not emit light by itself, and is called a backlight unit on the back of the LCD.

In order to use the LCD backlight unit as a light source, it is necessary to make a white light source by mixing an appropriate light source. For example, white light is generated by combining red, green, and blue light sources, or white light is formed by mixing two types of light sources of blue and yellow.

The combination of red, green and blue light sources can provide more perfect white light, but is relatively costly. On the other hand, the combination of two types of light sources of blue and yellow can lower the cost, but the quality of white light is worse than that of the prior art.

In recent years, white light is formed by mixing two kinds of light sources of blue and yellow, which is a method which is somewhat lower in quality than a method using red, green, and blue three-way light but is easy in technology and process and low in manufacturing cost, A method of implementing colors is utilized.

An organic electroluminescent device (OLED) refers to a device that emits light by using an electroluminescent phenomenon that emits light when an electric current flows through an organic compound. OLEDs can be driven at low voltages, are thin, have wide viewing angles and fast response speeds, and are attracting attention as next generation flat panel displays.

In order to use the OLED as a light source of a display, a method of realizing white light as in an LCD is required. A white light is generated by combining red, green, and blue light sources, or a white light is formed by combining a yellow light emitting material with a blue OLED And how to implement colors with color filters. However, such a method of implementing a color by a color filter after forming white light has a problem in that quality is poor and unnecessary light is blocked, thereby increasing the color purity.

This phenomenon of lowering the quality of white light is due to the presence of light having a wavelength of 400 to 520 nm, preferably 500 to 520 nm, which does not appear in white light due to mixing of red, green and blue trivalent lights. When the light of the above-mentioned region exists, the color purity of the adjacent blue and green is lowered. Therefore, by selectively removing only unnecessary regions using a compound that absorbs the wavelength of the light region, excellent white light can be obtained through the combination of two light sources of blue and yellow.

Examples of the compound having an absorption property in the light region of 400 to 520 nm, preferably 500 to 520 nm, include cyanine compounds, rhodamine compounds, coumarin compounds, and porphyrin compounds. However, the cyanine compound, the rhodamine compound, and the coumarin compound have a wide absorption region, absorbing a part of light even at a wavelength outside the selected region, resulting in a large decrease in luminance and poor light resistance. Further, since the papyrin compound has a narrow light absorbing region and a high absorbance, it is structurally difficult to use it as a material for a color purity improving filter because large absorption occurs not only in the selective region but also in other regions.

On the other hand, the pyromethene-based boron complex has a narrow full width half maximum (FWHM), and thus it is possible to design various molecules without a separate light absorption region other than the main light absorption region, It is capable of selectively absorbing only the light region of 500 to 520 nm, and can realize an unexposed light and a high light resistance.

An object of the present invention is to provide a dye comprising a pyromethene boron complex compound which is free of fluorescence and is excellent in light resistance and capable of absorbing light of a specific wavelength.

Another object of the present invention is to provide a filter for a display comprising the dye.

According to the above object, the present invention provides a dye comprising a pyromethene boron complex represented by the following formula (1)

[Chemical Formula 1]

In the above formulas,

R ¹ to R ⁶ are each independently hydrogen, C _1-8 alkyl, C _1-6 alkoxy, C _6-20 aryl; C _1-6 alkyl substituted with halogen; C _6-20 aryl substituted with halogen; Or C _1-6 alkoxy substituted with halogen, wherein n is an integer from 0 to 6;

A is C _6-20 aryl.

The present invention also provides a filter for a display comprising the dye.

The dye containing the pyromethene boron complex represented by the formula (1) of the present invention is free of fluorescence, excellent in light resistance, and capable of absorbing light of a specific wavelength, and thus can be usefully used as a dye for a display.

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

The dyes of the present invention include pyromethene boron complexes represented by the following formula:

In the above formulas,

R ¹ to R ⁶ are each independently hydrogen; C _{1 - 8} alkyl; C _{1 - 6} alkoxy; C _{6 - 20} aryl; Substituted by halogen, C _{1 - 6} alkyl; Substituted by halogen, C _{6 - 20} aryl; Or substituted C _{1 -6} alkoxy, halogen, wherein n is an integer from 0 to 6;

A is C _6-20 aryl.

In the example of the dye according to the invention, wherein R ¹ to R ⁴ are each independently, hydrogen or C _{1 - 6} alkyl, and; R ⁵ is hydrogen; C _{1 - 8} alkyl; C _{6 - 20} aryl; Or a halogen-substituted C _{6 -20} aryl; R ⁶ is C _{1 - 6} alkyl, and, where n is an integer from 0 to 4; A is C _{6 - 20} aryl is.

In another example of the dye according to the present invention, the R ¹ to R ⁴ are each independently, hydrogen or C _{1 - 6} alkyl, and; R ⁵ is hydrogen; C _{1 - 8} alkyl; Phenyl; Or phenyl substituted with halogen; R ⁶ is C _{1 - 6} alkyl, and, where n is an integer of 0 or 1; A is a phenyl ring or a naphthalene ring.

In a further example of the dye according to the invention, wherein R ¹ to R ⁴ are each independently, hydrogen or C _{1 - 6} alkyl, and; R ⁵ is hydrogen; C _{1 - 8} alkyl; Phenyl or phenyl substituted by halogen; R ⁶ is C _{1 - 6} alkyl, and, where n is an integer of 0 or 1; A is a naphthalene ring.

The term " halogen ", as used herein, unless otherwise indicated, means fluorine, chlorine, bromine or iodine.

The term " alkyl ", as used herein, unless otherwise indicated, refers to straight or branched hydrocarbon residues.

As used herein, the term "alkoxy" refers to the group -ORa, wherein Ra is alkyl as defined above. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, t-butoxy and the like.

The term " aryl ", as used herein, unless otherwise indicated, refers to an aromatic group including phenyl, naphthyl, and the like.

Preferable examples of the pyromethene boron complexes may be represented by the following general formulas (1a) to (1j):

[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

≪ RTI ID = 0.0 &

[Formula 1e]

(1f)

[Formula 1g]

[Chemical Formula 1h]

[Formula 1i]

[Chemical Formula 1j]

The dye comprising the pyromethene boron complex compound represented by Formula 1 has a maximum absorption wavelength at the boundary of blue and green, and the maximum absorption wavelength may be a wavelength of 400 nm to 520 nm, preferably 500 nm to 520 nm. have.

The dyes containing the pyromethene boron complexes represented by the above formula (1) are excellent in light fastness. For example, the dye of the present invention is diluted with a toluene solution to a concentration of 1,000 ppm and exposed to an Xe lamp (650 W / m ² , 50 ° C) for 24 hours. The dye is then diluted to 10 ppm and then exposed to UV / VIS spectrophotometer , When the dye residual ratio at the maximum absorption wavelength is measured, the dye residual ratio is at least 90%, preferably at least 95%. The dye of the present invention was diluted with toluene to a concentration of 1,000 ppm and exposed to Xe Lamp (650 W / m ² , 50 ° C) for 64 hours. After diluting the dye to 10 ppm, UV / VIS spectrophotometer When the dye residual ratio at the maximum absorption wavelength is measured, the dye residual ratio is 80% or more, preferably 90% or more.

The dyes comprising the pyromethene boron complexes can be used in the production of display filters, and thus the present invention also provides a filter for a display comprising the dyes.

The display filter may be formed by, for example, preparing a photosensitive coloring composition containing the dye, applying the photosensitive coloring composition on a substrate, heating the applied composition to form a film, A method of selectively exposing to light using a mask of a shape, then developing, and then heating and curing the developed film. However, the present invention is not limited thereto.

The dyes containing the pyromethene boron complexes represented by the above formula (1) may be used singly or in combination of two or more thereof. In addition, they may be used together with other auxiliary coloring agents such as pigments or dyes.

Hereinafter, the method for preparing the compound of formula (1) of the present invention will be described in detail.

The compound of Formula 1 of the present invention can be prepared as shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

In the above equations,

R ¹ to R ⁶ , A and n are the same as those mentioned in formula (1).

Step (1): Preparation of intermediate

Under a nitrogen atmosphere, 2 equivalents of the total amount of the compound (1) and / or the compound (1 '), 1 equivalent of the compound (2) and dichloromethane as the solvent are added to a 1 L round bottom flask and the mixture is stirred at room temperature for 12 to 36 hours. 5 equivalents of triethylamine (TEA) and 6 equivalents of boron trifluoride diethyl ether (BF ₃ OEt ₂ ) are added thereto, followed by stirring at room temperature for 2 to 6 hours. After completion of the reaction, water is added to separate the layers, and the organic layer is concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane to obtain the intermediate compound (3).

Step (2): Preparation of pyromethene boron complex

2 equivalents of aluminum chloride and dichloromethane as a solvent are added to 1 equivalent of the intermediate compound (3) obtained in the above step (1), and the mixture is stirred at room temperature for 1 to 20 minutes. 5 equivalents of the compound (4) For 1 minute to 1 hour. After completion of the reaction, water is added to separate the layers, and the organic layer is concentrated, and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane to obtain the compound of formula (1).

Example

Hereinafter, the present invention will be described in more detail with reference to the following Preparation Examples and Examples, but the present invention is not limited thereto.

Example 1: Synthesis of Compound (1a)

Step (1): Preparation of intermediate (1)

15.0 g (158 mmol) of 2,4-dimethylpyrrole, 6.2 g (79 mmol) of acetyl chloride and 450 ml of dichloromethane (DCM) were added to a 1 L round bottom flask under nitrogen atmosphere, and the mixture was stirred at room temperature for 24 hours. 55 ml of triethylamine (TEA) and 55 ml of boron triflouride diethyl ether (BF ₃ OEt ₂ ) were added thereto, followed by stirring at room temperature for 4 hours. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 9.4 g of an intermediate ) (Yield: 45%). The maximum absorption wavelength in the methyl ethyl ketone (MEK) of the intermediate (1) was 494 nm.

Step (2): Preparation of compound (1a)

1.3 g (10 mmol) of aluminum chloride (AlCl ₃ ) and 100 ml of dichloromethane were added to 1.3 g (5 mmol) of intermediate (1) obtained in the above step (1) and the mixture was stirred at room temperature for 5 minutes. 2.8 g (25 mmol) of hydroxybenzene was added thereto, and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.4 g of an orange solid compound (Yield: 83%). The maximum absorption wavelength was 500 nm in MEK.

Example 2: Compound of formula (Ib)

1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were added to 1.3 g (5 mmol) of the intermediate (1) obtained in the above step (1) of Example 1 and the mixture was stirred at room temperature for 5 minutes. 4.2 g (25 mmol) of butyl catechol were added and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.7 g of an orange solid (Yield: 87%). The maximum absorption wavelength was 500 nm in MEK.

Example  3: Compound of formula 1c

1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were added to 1.3 g (5 mmol) of Intermediate (1) obtained in the above step (1) of Example 1 and the mixture was stirred at room temperature for 5 minutes. 4.0 g (25 mmol) of dihydroxynaphthalene was added thereto, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, water was added thereto to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.5 g of an orange solid (Yield: 77%). The maximum absorption wavelength was 500 nm in MEK.

Example 4: Synthesis of Compound (1d)

Step (1): Preparation of intermediate (2)

15.0 g (158 mmol) of 2,4-dimethylpyrrole, 14.0 g (79 mmol) of n -octyl chloride and 450 ml of dichloromethane were added to a 1 L round bottom flask under nitrogen atmosphere, and the mixture was stirred at room temperature for 24 hours. 55 ml of triethylamine (TEA) and 55 ml of boron trifloride diethyl ether were added thereto, followed by stirring at room temperature for 4 hours. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 9.4 g of intermediate ) (Yield: 45%). The maximum absorption wavelength of the intermediate (2) was 495 nm in MEK.

Step (2): Preparation of compound (1d)

1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were added to 1.8 g (5 mmol) of Intermediate (2) obtained in the above step (1), and the mixture was stirred at room temperature for 5 minutes. Then, 1,2-dihydroxybenzene 2.8 g (25 mmol), and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.5 g of the compound of the formula (1d) (Yield: 72%). The maximum absorption wavelength was 501 nm in MEK.

Example 5: Compound of formula (Ie)

Step (1): Preparation of intermediate (3)

Under a nitrogen atmosphere, 16.8 g (177 mmol) of 2,4-dimethylpyrrole, 12.4 g (88 mmol) of benzoyl chloride and 500 ml of dichloromethane were added to a 1 L round bottom flask and the mixture was stirred at room temperature for 24 hours. 62 ml of triethylamine and 62 ml of boron triflouride diethyl ether were added thereto, followed by stirring at room temperature for 4 hours. Subsequently, water was added thereto to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 11.2 g of an intermediate (3) (Yield: 39%). The maximum absorption wavelength was 499 nm in MEK.

Step (2): Preparation of the compound of formula (Ie)

1.6 g (5 mmol) of the intermediate (3) obtained in the above step (1), 1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were added and the mixture was stirred at room temperature for 5 minutes. Then, 1,2-dihydroxybenzene 2.8 g (25 mmol), and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.5 g of an orange solid compound (Yield: 74%). The maximum absorption wavelength was 505 nm in MEK.

Example 6: Compound of formula (1f)

After the carried out into the intermediate (3) 1.6 g (5 mmol ), aluminum chloride, 1.3 g (10 mmol) and dichloromethane 100 ml obtained in Step 4 of Example 1 was stirred for 5 min at room temperature, 4- tert - butyl 4.2 g (25 mmol) of catechol were added, and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added thereto to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.8 g of an orange solid compound (Yield: 80%). The maximum absorption wavelength was 504 nm in MEK.

Example 7: Compound of formula 1g

1.6 g (5 mmol) of the intermediate (3) obtained in the step (1) of Example 4, 1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were added and the mixture was stirred at room temperature for 5 minutes. 4.0 g (25 mmol) of hydroxy naphthalene was added thereto, and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added thereto to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.8 g of a compound of the formula (1g) (Yield: 82%). The maximum absorption wavelength was 505 nm in MEK.

Example 8: Compound of formula (Ih)

Step (1): Preparation of intermediate (4)

7.1 g (75 mmol) of 2,4-dimethylpyrrole, 10.1 g (38 mmol) of 4-iodobenzoyl chloride and 250 ml of dichloromethane were placed in a 500 ml round-bottomed flask under nitrogen atmosphere, and the mixture was stirred at room temperature for 24 hours. 26 ml of triethylamine and 26 ml of boron trifloride diethyl ether were added thereto, followed by stirring at room temperature for 4 hours. Subsequently, water was added thereto to separate the layers. The organic layer was concentrated, and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 5.0 g of Intermediate (4) (Yield: 29%). The maximum absorption wavelength was 501 nm in MEK.

Step (2): Preparation of compound of formula (Ih)

2.3 g (5 mmol) of the intermediate (4) obtained in the above step (1), 1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were added and the mixture was stirred at room temperature for 5 minutes. Then, 1,2-dihydroxybenzene 2.8 g (25 mmol), and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 2.1 g of a compound of the formula (1h) (Yield: 79%). The maximum absorption wavelength was 506 nm in MEK.

Example  9: Compound of formula (I)

Step (1): Preparation of intermediate (5)

6.1 g (75 mmol) of 2-methylpyrrole, 5.3 g (38 mmol) of benzoyl chloride and 250 ml of dichloromethane were placed in a 1 L round bottom flask under a nitrogen atmosphere, and the mixture was stirred at room temperature for 24 hours. 26 ml of triethylamine and 26 ml of boron trifloride diethyl ether were added thereto, followed by stirring at room temperature for 4 hours. After completion of the reaction, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 4.5 g of Intermediate (5) (Yield: 40%). The maximum absorption wavelength was 509 nm in MEK.

Step (2): Preparation of the compound of formula (I)

1.5 g (5 mmol) of intermediate (5), 1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were placed in the above step (1), and the mixture was stirred at room temperature for 5 minutes. 2.8 g of 1,2-dihydroxybenzene (25 mmol) were added, and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.5 g of a compound of formula (I) (Yield: 84%). The maximum absorption wavelength was 515 nm in MEK.

Example 10: Preparation of Compound (Ij)

Step (1): Preparation of intermediate (6)

6.1 g (75 mmol) of 2-methylpyrrole, 6.0 g (38 mmol) of 4-fluorobenzoyl chloride and 250 ml of dichloromethane were added to a 1 L round bottom flask under nitrogen atmosphere, and the mixture was stirred at room temperature for 24 hours. 26 ml of triethylamine and 26 ml of boron trifloride diethyl ether were added thereto, followed by stirring at room temperature for 4 hours. Subsequently, water was added thereto to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 3.8 g of an orange solid (6) (Yield: 32%). The maximum absorption wavelength was 510 nm in MEK.

Step (2): Preparation of the compound of formula (lj)

1.6 g (5 mmol) of intermediate (6), 1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were placed in the above step (1), and the mixture was stirred at room temperature for 5 minutes. Then, 2.8 g of 1,2-dihydroxybenzene (25 mmol) were added, and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added thereto to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.5 g of an orange solid compound (Yield: 78%). The maximum absorption wavelength was 516 nm in MEK.

Comparative Example 1: Preparation of Comparative Compound 1

Step (1): Preparation of intermediate (1 ')

9.2 g (75 mmol) of 2,4-dimethyl-3-ethylpyrrole, 3.0 g (38 mmol) of acetyl chloride and 250 ml of dichloromethane were placed in a 1 L round bottom flask under a nitrogen atmosphere, and the mixture was stirred at room temperature for 24 hours. 26 ml of triethylamine and 26 ml of boron trifloride diethyl ether were added thereto, followed by stirring at room temperature for 4 hours. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane to obtain 3.9 g of an intermediate (1 ') as a red solid (yield: 32%). The maximum absorption wavelength was 517 nm in MEK.

Step (2): Preparation of Comparative Compound 1

1.6 g (5 mmol) of the intermediate (1 ') obtained in the above step (1), 1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were added and stirred at room temperature for 5 minutes. Then, 1,2-dihydroxybenzene 2.8 g (25 mmol), and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added to separate the layers. The organic layer was concentrated, and then a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) was conducted to obtain 1.5 g of Comparative Compound 1 as an orange solid (Yield: 75 %). The maximum absorption wavelength was 523 nm in MEK

Comparative Example 2: Preparation of Comparative Compound 2

Step (1): Preparation of intermediate (2 ')

9.2 g (75 mmol) of 2,4-dimethyl-3-ethylpyrrole, 6.7 g (38 mmol) of 4-chlorobenzoyl chloride and 250 ml of dichloromethane were placed in a 1 L round bottom flask under nitrogen atmosphere and stirred at room temperature for 24 hours Respectively. 26 ml of triethylamine and 26 ml of boron trifloride diethyl ether were added thereto, followed by stirring at room temperature for 4 hours. Subsequently, water was added thereto to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain red intermediate (2 ') 6.5 g (yield: 41%). The maximum absorption wavelength was 523 nm in MEK.

Step (2): Preparation of Comparative Compound 2

2.1 g (5 mmol) of the intermediate (2 ') obtained in the above step (1), 1.3 g (10 mmol) of aluminum chloride and 100 ml of dichloromethane were added and stirred at room temperature for 5 minutes. Then, 1,2-dihydroxybenzene 2.8 g (25 mmol), and the mixture was stirred at room temperature for 30 minutes. Subsequently, water was added to separate the layers. The organic layer was concentrated and then subjected to column chromatography using a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) to obtain 1.7 g of Comparative Compound 2 as an orange solid (Yield: 72%). The maximum absorption wavelength was 529 nm in MEK

Test Example

Test Example 1: Measurement of maximum absorption wavelength, extinction coefficient and half width

The compound of Examples 1 to 10, the intermediate (1) prepared in Step (1) of Example 1, the intermediate (3) prepared in Step (1) of Example 5, and the compounds of Comparative Examples 1 and 2 After diluting with a methyl ethyl ketone (MEK) solvent to a concentration of 10 ppm, the maximum absorption wavelength was measured with a UV / VIS spectrophotometer (Perkinelmer, Lamda25).

Absorbance Units obtained by measuring a solution having a gram extinction coefficient (ml / g · cm) of 10 ppm by a cuvette having an optical path length of 10 mm were calculated according to the Beer's law. Further, the half width (nm), which is a region where the absorption at each maximum absorption wavelength was half, was measured.

Test Example 2: Calculation of fluorescence quantum yield (PL)

The compound of Examples 1 to 10, the intermediate (1) prepared in Step (1) of Example 1, the intermediate (3) prepared in Step (1) of Example 5, and the compounds of Comparative Examples 1 and 2 After diluting with methanol and measuring PL (Perkinelmer, LS-55), the fluorescence quantum yield (Ф) was calculated.

The compound of Examples 1 to 10, the intermediate (1) prepared in the step (1) of Example 1, the intermediate (3) prepared in the step (1) of Example 5, and the intermediate And 2, the maximum absorption wavelength, extinction coefficient, half band width and fluorescence quantum yield in MEK were shown.

Compound structure Maximum absorption wavelength (nm) Extinction coefficient
( ml / g · cm ) Half width (nm) Fluorescent quantum
Yield (Ф) Example 1

500 2.0 × 10 ⁵ 22 Not measured
Not
(nd) Example 2

500 1.9 × 10 ⁵ 22 nd Example 3

500 2.1.x10 ⁵ 21 nd Example 4

501 1.8X10 ⁵ 23 nd Example 5

505 2.1.x10 ⁵ 20 nd Example 6

504 2.0 × 10 ⁵ 21 nd Example 7

505 2.0 × 10 ⁵ 20 nd Example 8

506 1.8X10 ⁵ 22 nd Example 9

515 2.2 X 10 ⁵ 21 nd Example 10

516 2.0 × 10 ⁵ 22 nd Example 1
In step (1)
Intermediate (1)

494 2.9 × 10 ⁵ 21 0.95 Example 5
In step (1)
Intermediate (3)

499 2.1.x10 ⁵ 20 0.65 Comparative Example 1

523 1.8X10 ⁵ 22 nd Comparative Example 2

529 1.7 X 10 ⁵ 24 nd

Test Example 3: Evaluation of light resistance

The compound of Examples 1 to 4, the intermediate (1) prepared in the step (1) of Example 1 and the intermediate (3) prepared in the step (1) of Example 5 were dissolved in a toluene solution at a concentration of 1,000 ppm And then exposed to a Xe lamp (650 W / m ² , 50 ° C) for 24 hours and 64 hours, respectively.

After that, it was diluted to a concentration of 10 ppm, and the retention rate of the coloring matter at each maximum absorption wavelength was measured using a UV / VIS spectrophotometer (Perkinelmer, Lamda25), and it is shown in Table 2.

(%) At the maximum absorption wavelength after 24 hours light resistance test (%) At the maximum absorption wavelength after 64 hours light resistance test Example 1 95 93 Example 2 99 90 Example 3 99 93 Example 4 98 95 Intermediate (1) 75 21 Intermediate (3) 81 37

As can be seen from Table 1, the pyromethene boron complex according to the present invention has a maximum absorption wavelength in the range of 480 to 520 nm, and a narrow half width. Therefore, the color purity of blue and green of the display to which the display filter including the same is applied Can be selectively enhanced.

From Table 1, it can be confirmed that the pyromethene boron complex according to the present invention has no fluorescence. From Table 2, it can be seen that the pyromethene boron complex according to the present invention has excellent light resistance.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is clearly understood that the same is by way of illustration and example only and is not to be taken by way of limitation, It is to be understood that the invention may be practiced within the scope of the appended claims.

Claims (9)

A dye comprising a pyromethene boron complex represented by the following formula (1):
[Chemical Formula 1]

In the above formulas,
R ¹ to R ⁶ are each independently hydrogen; C _{1 - 8} alkyl; C _{1 - 6} alkoxy; C _{6 - 20} aryl; Substituted by halogen, C _{1 - 6} alkyl; Substituted by halogen, C _{6 - 20} aryl; Or substituted C _{1 -6} alkoxy, halogen, wherein n is an integer from 0 to 6;
A is C _6-20 aryl.
The method according to claim 1,
R ¹ to R ⁴ are each independently hydrogen or C _1-6 alkyl;
R ⁵ is hydrogen; C _{1 - 8} alkyl; C _{6 - 20} aryl; Or substituted by halogen, C _{6 - 20} aryl;
R ⁶ is C _{1 - 6} alkyl, and, where n is an integer from 0 to 4;
A is a C _6-20 aryl.
The method according to claim 1,
R ¹ to R ⁴ are each independently hydrogen or C _1-6 alkyl;
R ⁵ is hydrogen; C _{1 - 8} alkyl; Phenyl; Or phenyl substituted with halogen;
R ⁶ is C _{1 - 6} alkyl, and, where n is an integer of 0 or 1;
A is a phenyl ring or a naphthalene ring.
The method according to claim 1,
R ¹ to R ⁴ are each independently hydrogen or C _1-6 alkyl;
R ⁵ is hydrogen; C _{1 - 8} alkyl; Phenyl; Or phenyl substituted with halogen;
R ⁶ is C _{1 - 6} alkyl, and, where n is an integer of 0 or 1;
A is a naphthalene ring.
The method according to claim 1,
Wherein the pyromethene boron complex is any one selected from the group consisting of compounds represented by the following formulas (1a) to (1j):
[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

≪ RTI ID = 0.0 &

[Formula 1e]

(1f)

[Formula 1g]

[Chemical Formula 1h]

[Formula 1i]

And
[Chemical Formula 1j]

.
The method according to claim 1,
Wherein the dye has a maximum absorption wavelength of 400 to 520 nm.
The method according to claim 1,
The dye was diluted with a toluene solution to a concentration of 1,000 ppm and exposed to Xe lamp (650 W / m ² and 50 ° C) for 24 hours. The dye was diluted to 10 ppm, and then the maximum was measured using a UV / VIS spectrophotometer Wherein a dye residual ratio at the absorption wavelength is measured, wherein the dye residual ratio is at least 90%.
The method according to claim 1,
The dye was diluted with a toluene solution to a concentration of 1,000 ppm and exposed to Xe lamp (650 W / m ² and 50 ° C) for 64 hours. The dye was diluted to 10 ppm, and then the maximum was measured using a UV / VIS spectrophotometer Wherein the dye residual ratio at the absorption wavelength is 80% or more.
9. A filter for a display comprising a dye according to any one of claims 1 to 8.