KR102051911B1 - High transmissional yellow dye for lcd and synthetic method thereof - Google Patents

Abstract

The present invention relates to a high-permeability yellow dye for LCD, a dye dispersion containing the dye, a coloring composition containing the dye dispersion, a color filter containing the coloring composition, and a method for producing the dye.

Description

High permeability yellow dye for LCD and manufacturing method thereof {HIGH TRANSMISSIONAL YELLOW DYE FOR LCD AND SYNTHETIC METHOD THEREOF}

The present invention relates to a high-permeability yellow dye for LCD, a dye dispersion containing the dye, a coloring composition containing the dye dispersion, a color filter containing the coloring composition, and a method for producing the dye.

The color filter used in the liquid crystal display device is used to implement a color image in the display device. The color filter may be manufactured by coating, curing, and patterning a pigment on a substrate using various methods. . The color filter is formed of three pixel portions of red, green, and blue on a transparent substrate such as glass, and color filters used in an image display device or a solid state image pickup device are typically red (R), green (G), and It has a coloring pattern of three primary colors of blue (B), and serves to color the light passing through or to separate it into three primary colors. Pigments displaying red, green, and blue are composed of fine particles, that is, pigments, and these pigments are used alone to obtain color display characteristics of a desired region. , Blue is displayed.

In recent years, the development of large-screen and high-definition technology for liquid crystal displays has progressed, and their use has been greatly expanded from notebook displays to desktop monitors and television monitors. In such a situation, color filters used for liquid crystal displays and the like are required to have high color purity. In particular, it is important to satisfy this required characteristic in a high definition display that enables high quality image display. Light passing through the color filter is colored with the color of each pixel, and the light of those colors is synthesized to form a color image. Therefore, a color filter having a pixel degree of very high purity with three colors of predetermined RGB which makes this possible is desired.

On the other hand, with the spread of digital cameras, camera-equipped mobile phones, and the like, the demand for solid-state imaging devices such as CCD image sensors has also increased significantly. As a color filter is used as a key device of such a display or an optical element, the demand for cost reduction along with the demand for high quality for the color filter is increasing.

The dye used for the color filter is required to have the following properties. That is, optical disturbances such as those having desirable light absorption characteristics in terms of color reproducibility, light scattering, which is a cause of lowering the contrast of the liquid crystal display, and color irregularity, which is a cause of color unevenness or roughness of the solid-state image pickup device, are caused. It is necessary to be able to be absent, to have suitable resistance, for example, heat resistance, light resistance, moist heat resistance, etc., under the environmental conditions used, and to be able to provide thin molar absorption coefficients by providing a large molar absorption coefficient.

There is an increasing demand for a liquid crystal display device having high image quality, i.e., contrast and color purity, and in order to improve contrast, the particle size of a pigment (such as an organic pigment) in the photosensitive resin composition for color filter formation is required to be smaller. Moreover, it is also important to increase the content rate of the pigment (organic pigment etc.) with respect to solid content of the said photosensitive resin composition for color purity improvement.

In recent years, further refinement is required in color filters for solid state image pickup devices such as CCDs. Therefore, in order to suppress the color nonuniformity by the coarse particle of a pigment | dye, refinement | miniaturization of a pigment | dye is desired.

The said dye and pigment used as a pigment need to have the following properties in common. That is, the thing which has preferable absorption characteristic in color reproducibility, the fastness under the environmental conditions used, for example, the thing with favorable resistance to oxidizing gases, such as light resistance, heat resistance, and ozone, etc. are mentioned. In addition, when a pigment is a pigment, it is also substantially insoluble in water and an organic solvent, and also has properties such as having good chemical fastness and not impairing desirable absorption characteristics in the molecular dispersed state even when used as particles. You need to be. The required properties can be controlled by the strength of the intermolecular interaction, but it is difficult to achieve compatibility because the required properties are in a trade off relationship.

Under these circumstances, a technique of using a dye instead of a pigment as a dye has been proposed. When dyes are used instead of pigments, color filters for solid-state imaging devices are expected to achieve high resolution by eliminating problems of color unevenness and roughness, and optical characteristics such as contrast and haze in liquid crystal displays and organic EL displays. Is expected to improve.

However, dye-containing colored curable compositions have other problems as described below.

(1) The dye in the molecular dispersed state generally lacks light resistance and heat resistance as compared with the pigment forming the molecular aggregate. In particular, when forming a film of ITO (Indium Tin Oxide) which is widely used as an electrode of a liquid crystal display device or the like, there is a problem that the optical characteristic is changed by a high temperature process.

(2) The dyes in the molecular dispersed state generally lack solvent resistance as compared to pigments that form molecular aggregates.

(3) Dye tends to suppress a radical polymerization reaction, and in the system using radical polymerization as a hardening means, it is difficult to design a colored curable composition.

(4) Since the conventional dye has low solubility in aqueous alkali solution or organic solvent, it is difficult to obtain a colored curable composition having a desired spectrum.

(5) The dye often exhibits interaction with other components in the colored curable composition, making it difficult to control the solubility (developmentability) of the exposed portion and the non-exposed portion,

(6) When the molar extinction coefficient (ε) of dye is low, it is necessary to add a large amount of dye. Therefore, the amount of other components such as a polymerizable compound (monomer), a binder, or a photopolymerization initiator in the colored curable composition should be relatively reduced, so that the curability of the composition, heat resistance after curing, and developability are lowered.

Currently, metal halide phthalocyanine dyes and metal halide phthalocyanine pigments are generally used to form green pixel portions.

However, the transmission spectrum of the phthalocyanine-based dye as the main green dye has a form similar to the transmission spectrum required by the color filter, but the absorption is insufficient in the short wavelength region. Therefore, if the short wavelength region is completely absorbed, theoretically higher color reproducibility can be expected.

Accordingly, there is a need to develop a modified dye for a liquid crystal display color filter that can be used as a correction dye, such as a correction dye of green dye, which can effectively absorb the short wavelength region while overcoming the above disadvantages.

An object of the present invention is to provide a high-permeability yellow dye for LCD, a dye dispersion comprising the dye, a coloring composition comprising the dye dispersion, a color filter comprising the coloring composition and a method for producing the dye.

In the present invention, to develop a hybrid color photoresist (PR) suitable for a low-power LED BLU light source to replace the existing LCD color filter backlight (BLU) light source CCFL. To this end, it is necessary to develop high-durability yellow correction dyes that can effectively absorb short wavelengths in the 400-500 nm range as a complement to the main green dyes. We want to implement the spectrum.

An aspect of the present invention for achieving the above object is to provide a dye represented by the following formula (I).

Formula (I)

Wherein R is hydrogen, halogen, hydroxy, cyano, nitro, amino, amidino, carbonyl, carboxy, sulfonyl, substituted or unsubstituted C ₁ -C ₁₀ alkyl, substituted or unsubstituted C _2- C ₁₀ alkenyl, substituted or unsubstituted C ₂ to C ₁₀ alkynyl, substituted or unsubstituted C ₁ to C ₁₀ alkoxy, substituted or unsubstituted C ₃ to C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ ~ C ₁₀ cycloalkenyl, substituted or unsubstituted C ₃ ~ C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ ~ C ₁₀ heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy , Substituted or unsubstituted arylthio, substituted or unsubstituted hetero aryl.

Another aspect of the present invention for achieving the above object is to provide a dye represented by the following formula (II).

Formula (II)

Wherein R is hydrogen, halogen, hydroxy, cyano, nitro, amino, amidino, carbonyl, carboxy, sulfonyl, substituted or unsubstituted C ₁ -C ₁₀ alkyl, substituted or unsubstituted C _2- C ₁₀ alkenyl, substituted or unsubstituted C ₂ to C ₁₀ alkynyl, substituted or unsubstituted C ₁ to C ₁₀ alkoxy, substituted or unsubstituted C ₃ to C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ ~ C ₁₀ cycloalkenyl, substituted or unsubstituted C ₃ ~ C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ ~ C ₁₀ heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy , Substituted or unsubstituted arylthio, substituted or unsubstituted hetero aryl.

The dye may be to absorb a wavelength region of 400 nm to 500 nm.

Specifically, the dye of formula (I) or formula (II) may absorb a wavelength range of 480 nm or less, and more preferably, absorb a wavelength range of 450 nm to 480 nm.

The dye may be used as a correction dye of the green dye.

The transmission spectrum of the phthalocyanine-based green dye has a form similar to the transmission spectrum required by the color filter, but absorption in the short wavelength region does not occur properly. Therefore, there is a need for a correction dye that can absorb shorter wavelengths more completely to complement the transmission spectrum. By using a correction dye, the color reproducibility can be increased, and specifically, a yellow correction dye having excellent durability capable of effectively absorbing a wavelength region of 480 nm or less is required. However, dyes and pigments that generally exhibit yellow color exhibit low heat and light resistance because they absorb high energy in the short wavelength region compared to other colors. In order to solve this problem, the present invention provides a coronene diimide-based yellow correction dye that satisfies high heat resistance and high light resistance, and a yellow dye capable of effectively absorbing a short wavelength region by variously changing their structure.

Coronene diimide is a yellow-orange dye having a maximum absorption wavelength in the range of 430-530 nm, and exhibits excellent heat resistance and very sharp absorption spectrum. When the aromatic structure of perylene is extended in the long molecular axis direction, such as terylene and quaterylene, the absorption spectrum is long, as is well known, and the molar extinction coefficient is increased. However, when the aromatic structure is extended in the direction of the short molecular axis, the maximum absorption wavelength is shortened to 100 nm while maintaining the high molar extinction coefficient of perylene. These coronene derivatives are very rigid because they have a very rigid structure with stability similar to that of perylene and have a high intensity yellow color. In general, the molar extinction coefficient of the organic pigment increases with the size of the aromatic structure, but it is very difficult to synthesize a yellow pigment having a high color intensity because it is connected to the long wavelength of the absorption peak.

In the coronene diimide-based dye of the present invention, the bulky group has a planar surface of the perylene body due to steric hindrance with the carbonyl group at the 3,4,9,10 position by introducing a bulky group including a benzene ring through imidization at both ends. Will be distorted. This has the effect of preventing the intermolecular association of the coronene body to enhance the solubility of the dye. In addition, a bulky functional group such as isopropyl group may be present at the ortho position of the benzene ring portion connected to the coronene body to maximize this effect. Such coronene terminal partial substitution has little effect on the UV-visible absorption spectrum of the dye because the conjugation node is present in the nitrogen atom so that the conjugation of the coronene body is not extended.

Imidization at both terminal positions also has the effect of effectively enhancing solubility in organic solvents. In addition, by introducing bisimide groups at both ends and additionally introducing a bulky group at the bay position of the main body to further impart steric hindrance, solubility may be further improved. When a bulky group is introduced, such as a derivative in which the aryl group is substituted at the bay position, not only the bulky aryl group is distorted from the coronene body but also the planarity of the coronene body itself is broken, thereby improving solubility by 100 times or more compared to the derivative substituted only at the terminal portion. It can work. The principle can be expressed as follows.

Another aspect of the present invention for achieving the above object is to provide a dye dispersion comprising the dye.

Another aspect of the present invention for achieving the above object is to provide a coloring composition comprising the dye dispersion.

Another aspect of the present invention for achieving the above object is to provide a color filter, characterized in that formed using the coloring composition.

Another aspect of the present invention for achieving the above object is (a) adding a halogen to the phenylene-3,4,9,10-tetracarboxy dianhydride to form a first intermediate; (b) adding and reacting an aniline derivative to the first intermediate to form a second intermediate; (C) to provide a method for producing a dye comprising the step of forming a dye compound by the addition of a phenyl vinyl boronic acid derivative to the second intermediate.

The first intermediate may be represented by the following general formula (III), wherein R 'or R' 'may be each independently selected from the group consisting of hydrogen and halogen, provided that R' or R '' are all Except for hydrogen).

Formula (III)

The second intermediate may be represented by the following formula (IV), wherein R 'or R''are each independently selected from the group consisting of hydrogen and halogen, provided that R' or R '' are all hydrogen R is hydrogen, halogen, hydroxy, cyano, nitro, amino, amidino, carbonyl, carboxy, sulfonyl, substituted or unsubstituted C ₁ -C ₁₀ alkyl, substituted or unsubstituted C ₂ to C ₁₀ alkenyl, substituted or unsubstituted C ₂ to C ₁₀ alkynyl, substituted or unsubstituted C ₁ to C ₁₀ alkoxy, substituted or unsubstituted C ₃ to C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ to C ₁₀ cycloalkenyl, substituted or unsubstituted C ₃ to C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ to C ₁₀ heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted Aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted hetero aryl It may be selected from the group.

Formula (IV)

The dye production method of the present invention allows dyes to be produced in high yields under simple synthetic conditions by one-step reactions without incidental reactions.

The preparation method may further include (d) purifying the dye after step (c).

In order to provide a green dye corresponding to a low power type LED BLU light source to replace the existing CCFL BLU, the present invention provides a highly durable yellow color correction dye that can effectively absorb short wavelength regions by supplementing the main pigment dye. Coloration with green dyes can provide an optimal green color filter. In addition, the dye synthesized in the present invention is improved to have suitable physical properties for photoresist for LCD, such as having a high solubility (high light resistance, high heat resistance) suitable for the current LCD process while having a solubility suitable for conventional pigment type solvent (PGMEA). . In particular, Cd2 was excellent in color characteristics and heat resistance. In addition, it has strong fluorescence characteristics, which may be useful in other fields besides color filters.

The present invention provides high permeability yellow dyes for LCDs while at the same time providing optimal synthesis and mass synthesis techniques.

Figure 1 shows the structure of the coronene diimide dyes Cd1 and Cd2 provided in the present invention.
2 is a graph showing UV-VIS absorption spectral peaks of the synthesized dyes Cd1 and Cd2.
3 shows a transmission spectrum of a spin coated color filter.
4 shows a CIE 1931 chromaticity diagram of a spin coated color filter.
5 is a TGA (Thermogravimetric Analyzer) graph of the synthesized dyes Cd1 and Cd2.
Figure 6a is a ¹³ C-NMR results confirming the synthesis of the dye Cd1.
6B is a ¹ H-NMR result confirming the synthesis of the dye Cd1.
7A shows ¹³ C-NMR results confirming the synthesis of dye Cd2.
7B is a ¹ H-NMR result confirming the synthesis of the dye Cd2.
8A is a MALDI-TOF result confirming the synthesis of dye Cd1.
8B is a MALDI-TOF result confirming the synthesis of dye Cd1 (enlarged view).
9A is a MALDI-TOF result confirming the synthesis of dye Cd1.
9B is a MALDI-TOF result confirming the synthesis of dye Cd1 (enlarged view).

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily practice the present invention. As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention.

1. Synthesis of Dyes

(1) bromination reaction

16 g (0.0407 mol) of perylene-3,4,9,10-tetracarboxy dianhydride, 0.39 g (0.00152 mol) of iodine and 225 ml of 98% sulfuric acid were stirred at room temperature for 2 hours. The temperature was raised to 80 ° C. and bromine 4.6 ml (0.09 mol) was added slowly over 2 hours. The reaction was carried out for 16 hours while maintaining the temperature, and then cooled to room temperature and the remaining bromine was removed with nitrogen gas. The precipitate was slowly poured into 2000 ml of distilled water in a cold water bath and filtered under reduced pressure. It was washed several times with distilled water until the pH was 7 and dried in a vacuum oven. Substances produced during this synthesis are 1-bromoperylene-3,4,9,10-tetracarboxy dianhydride substituted with one bromine and 1,7-dibromoperylene-3,4 substituted with two bromines. , 9,10-tetracarboxy dianhydride is mixed. The bromination reaction is carried out as follows.

(2) imidization reaction

1,7-dibromoperylene-3,4,9,10-tetracarboxy dianhydride 8 g (0.0145 mol), 2,6-diisopropylaniline 8.28 g (0.0467 mol), acetic acid 4.6 ml N-methyl It was put in 100 ml of pyrrolidone and refluxed at 120 ° C. under nitrogen gas for 96 hours. When the reaction was completed, slowly poured into 1000 ml of distilled water to precipitate, and the resulting precipitate was filtered under reduced pressure. It was washed several times with distilled water until the pH was 7 and dried in a vacuum oven. The dried product was purified by column using dichloromethane, N, N'-bis (2,6-diisopropylphenyl) -1,7-dibromoperylene-3,4,9,10 tetracarboxydiimide Could get

N, N'-bis (2,6-diisopropylphenyl) was subjected to the imidization reaction under the same stoichiometry and conditions using 1-bromoperylene-3,4,9,10-tetracarboxy dianhydride. -1-bromoperylene-3,4,9,10 tetracarboxydiimide was obtained.

The imidation reaction is carried out as follows.

(3) benzene ring formation reaction

N, N'-bis (2,6-diisopropylphenyl) -1,7-dibromoperylene-3,4,9,10-tetracarboximide (1.0 g, 1.15 mmol) was dried ethanol ( 5.79 ml), benzene (33.12 ml), water (8.13 ml) co-solvent, and then 1-phenyl vinyl boronic acid (0.68 g, 4.6 mmol), Pd (PPh ₃ ) ₄ (66.57 mg, 5.0 mol%), Na ₂ CO ₃ (1.2 g, 11.5 mmol) was added sequentially under nitrogen gas. After reacting at 80 ° C. for 120 hours, the reaction product was quenched by adding water and extracted several times with CH ₂ Cl ₂ . The extracted organic layer was dried over MgSO ₄ several times and evaporated under reduced pressure to remove the solvent. The obtained crude solid was purified by column chromatography on silica gel with 100% CH ₂ Cl ₂ . A second band containing a yellow compound was received to give the product. The resulting compound was the following diphenylcoronene tetracarboxydiimide (Cd1).

N, N'-bis (2,6-diisopropylphenyl) -1-bromoperylene-3,4,9,10 tetracarboxydiimide (1.0 g, 1.27 mmol), 1-phenyl vinyl boronic acid (0.38 g, 2.54 mmol), Pd (PPh ₃ ) ₄ (66.57 mg, 5.0 mol%), and Na ₂ CO ₃ (1.2 g, 11.5 mmol) were subjected to the same reaction and purification as above except for monophenyl Benzoperylene tetracarboxydiimide (Cd2) was obtained.

: Cd1

: Cd1

Yield 52.1%; Mp> 300 ° C. (decomp.).

¹ H NMR (500 MHz, CDCl ₃ ): δ = 1.24 (d, J = 6.5 Hz, 24H), 2.99 (septet, J = 40.0 Hz, 4H), 7.42 (d, J = 8.5 Hz, 4H), 7.54 (t, J = 9.2 Hz, 2H), 7.70 (t, J = 9.0 Hz, 2H), 7.76 (t, J = 13.5 Hz, 4H), 7.97 (t, J = 10.2 Hz, 4H), 9.27 (s , 2H), 10.17 (s, 2H), 10.22 (s, 2H);

¹³ C NMR (126 MHz, CDCl ₃ ): δ = 23.98, 24.34, 29.52, 29.92, 122.20, 122.38, 124.00, 124.26, 124.39, 124.49, 125.21, 129.03, 129.35, 129.42, 129.93, 130.05, 130.37, 130.44, 131. , 131.21, 131.46, 131.76, 139.38, 139.49, 142.93, 143.13, 145.96, 146.07, 164.99, 165.13;

MALDI-TOF MS: m / z 911.07 (100%, [M + H ⁺ ]); Found: C, 84.52; H, 5. 45; N, 3.10%. Calc. for C ₆₄ H ₅₀ N ₂ O ₄ : C, 84.37; H, 5.53; N, 3.07%.

: Cd2

: Cd2

Yield 66.8%; Mp> 300 ° C. (decomp.).

¹ H NMR (500 MHz, CDCl ₃ ): δ = 1.21 (d, J = 7.0 Hz, 24H), 2.84 (septet, J = 38.5 Hz, 4H), 7.38 (dd, J = 26.2 Hz, 4H), 7.52 (m, J = 18.4 Hz, 2H), 7.61 (t, J = 9.9 Hz, 1H), 7.67 (t, J = 14.5 Hz, 2H), 7.77 (t, J = 9.4 Hz, 2H), 8.81 (s , 1H), 9.22 (d, J = 8.2 Hz, 2H), 9.49 (d, J = 10.8 Hz, 2H), 9.56 (s, 1H), 9.63 (s, 1H);

¹³ C NMR (126 MHz, CDCl ₃ ): δ = 24.25, 24.32, 29.55, 29.92, 122.41, 122.60, 123.22, 123.62, 123.71, 124.30, 124.42, 124.49, 124.73, 124.88, 126.08, 128.02, 128.10, 128.93, 128.93 , 129.31, 129.72, 129.86, 129.88, 130.00, 130.25, 130.75, 130.92, 130.96, 131.10, 133.50, 133.94, 134.29, 135.21, 138.91, 143.15, 145.91, 145.96, 164.17, 164.26, 164.35;

MALDI-TOF MS: m / z 811.09 (100%, [M + H ⁺ ]); Found: C, 83.12; H, 5.58; N, 3.42%. Calc. for C ₅₆ H ₄₆ N ₂ O ₄ : C, 82.94; H, 5.72; N, 3.45%.

2. Preparation of Dye-Based Inks and Color Filters

The dye-based ink for color filters consisted of cyclohexanone (3.2 g), an acrylic binder (1.4 g) and a dye (0.1 g). The prepared dye-based ink was coated on a transparent glass substrate using a MIDAS System SPIN-1200D spin coater. The coating speed started at 100 rpm for 5 seconds, increased to 500 rpm and held for 20 seconds. The dye coated color filter was dried at 80 ° C. for 20 minutes and postbaked at 230 ° C. for 1 hour.

3. Spectroscopic Characterization of Dyes

The UV-VIS absorption peaks of the coronene diimide dyes synthesized in Table 1 and FIG. 2 are shown. Cd2 showed the strongest main absorption peak at 472 nm, which is due to the general vibrating structure of perylene and gives this dye a strong vivid yellow color. The shape of this main peak was very similar to that of Cd1, but about 22 nm of hypsochromic shift was observed. The extinction coefficient of Cd2 at 472 nm (ε = 65,688 M ^-1 cm ^-1 ) was similar to that of Cd1 at 494 nm (ε = 66,000 M ^-1 cm ^-1 ) and the absorption coefficient of coronene at 428 nm. (ε = 62,000 M ⁻¹ cm ⁻¹ ). Cd1 showed the strongest main absorption peak at much shorter wavelengths with a minor absorption line at 512 nm (426 nm, ε = 59,988 M ^-1 cm ^-1 ). The shape of these absorption peaks is similar to the absorption peaks of the coronene derivatives, and the extent to which the distance between the maximum absorption lines is slightly different. The minor absorption line at about 512 nm causes the Cd1 to be somewhat hazy in solution compared to the much brighter, greener Cd2. As shown in the graph, these two dyes are suitable for use as calibration dyes, especially dye Cd2, which shows a very strong and sharp absorption peak just before 500 nm, making it ideal for use as a yellow dye for LCD color filters.

[Table 1] Absorption peak of coronene diimide dye

4. Spectrum and Color Characteristics of Spin Coated Color Filters

Because of the smaller particle size of the dye dissolved in the medium, the dye-based color filter shows better transmittance than the pigment-based color filter, resulting in less light scattering. In particular, Cd2 may exhibit an ideal transmission spectrum when used as a calibration yellow dye (Table 2, FIG. 3). Main dyes for greens, such as DC-G, have a bluish bluish green color through a wide range of wavelengths.

: DC-G

DC-G

However, dye compositions containing Cd2 show sharp transmission spectra that change rapidly just before 500 nm, as can be seen in FIG. 3. Therefore, vivid and clean green color can be obtained by mixing Cd2. When mixed with the coronene diimide-based yellow dye, the λ _max of the color filter shifts about 20 nm red, resulting in a smaller green dye requirement to approximate the green color for conventional LCD color filters. Table 3 and FIG. 4 show the coordinate values of the spin coated color filter. Upon mixing Cd2 the x value of DC-G was close to the green coordinates (0.274, 0.572) of the conventional LCD color filter.

TABLE 2 Transmittance of spin coated color filters

[Table 3] Color difference index of color coordinate and spin coated color filter corresponding to CIE 1931 chromaticity diagram

5. Heat resistance characterization of dye

Although dyes have better optical properties than pigments, they are difficult to use as LCD color filters because of their low heat resistance. Dyes suitable for use as color filters should be able to withstand weight loss at 220 ° C., the highest temperature in the current LCD manufacturing process.

Thermo Gravimetric Analyzer (TGA) The heat resistance of the synthesized dye was measured using a TA Instruments Thermogravimetric Analyzer 2050 (FIG. 5). The heat resistance test was performed by measuring the change in mass reduction rate (w%) by heating the temperature from 10 ° C./min to 50 ° C. to 400 ° C. and passing the isothermal section at 220 ° C. for 30 minutes.

The synthesized new dyes Cd1 and Cd2 basically have a harder structure than other yellow dyes, and thus have excellent heat resistance, but the heat resistance was different depending on the degree of introduction of substituents. In the case of Cd2, which is a monophenyl benzoperylene structure, the mass reduction in the isothermal section is less than 3%, which shows particularly sufficient heat resistance to be applied as a color filter.

4. Solubility Analysis of Dyes

The coronene derivatives Cd1 and Cd2 showed very good solubility in almost all organic solvents such as dichloromethane, hexane, toluene. This is because the phenyl groups substituted at the bay position of coronene, as intended in the design of the dye, are distorted with respect to the aromatic structure of the main body to impart steric hindrance to prevent dye-to-dye association. In addition, by introducing a bulky functional group including a benzene ring at both ends, the solubility of the solubility is also analyzed to have a twisted structure with respect to the plane of the main body due to the steric hindrance with the carbonyl groups in the 3,4,9,10 positions.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements of those skilled in the art using the basic concepts of the present invention defined in the following claims are also provided. It belongs to the scope of rights.

Claims (9)

Dye represented by the following formula (I):
Formula (I)

here,
R is hydrogen, halogen, hydroxy, cyano, nitro, amino, amidino, substituted or unsubstituted C ₁ -C ₁₀ alkyl, substituted or unsubstituted C ₂ -C ₁₀ alkenyl, substituted or unsubstituted C ₂ to C ₁₀ alkynyl, substituted or unsubstituted C ₁ to C ₁₀ alkoxy, substituted or unsubstituted C ₃ to C ₁₀ cycloalkyl, substituted or unsubstituted C ₃ to C ₁₀ cycloalkenyl, substituted or unsubstituted Substituted C ₃ -C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ heterocycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted Or unsubstituted hetero aryl. delete The dye according to claim 1, wherein the dye absorbs a wavelength region of 400 nm to 500 nm. The dye according to claim 1, wherein said dye is used as a correction dye of green dye. Dye dispersion containing the dye of Claim 1. It contains the dye dispersion of Claim 5, The coloring composition characterized by the above-mentioned. It is formed using the coloring composition of Claim 6, The color filter characterized by the above-mentioned. delete delete

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