Phthalimide phthalocyanine derivative as well as preparation method, pigment composition and application thereof

Abstract

The invention belongs to the technical field of organic pigment compositions, and discloses a phthalimide phthalocyanine derivative and a preparation method thereof, a pigment composition and application, the phthalimide phthalocyanine derivative has a structure as shown in formula I, M is a metal atom, L is a bridging group, and n is an integer from 1 to 8. The preparation method comprises the following steps: firstly, preparing a phthalocyanine fragment containing a phthalimide structure, and then assembling into the phthalocyanine derivative. The yield of the phthalimide derivative prepared by the method disclosed by the invention is greatly improved, and the phthalimide derivative has higher industrialization value; the variety of the phthalimide derivatives is rich, and the pigment composition with excellent performance can be optimized. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the technical field of organic pigment compositions, and in particular to a phthalimide phthalocyanine derivative and a preparation method thereof, a pigment composition and application thereof. Background Art

[0002] Organic pigments used in color filters have high brightness and contrast. This requires that the organic pigments have fine particle sizes, usually requiring the primary particles of organic pigments to be less than 100nm. The preparation of such fine organic pigments usually requires the addition of pigment derivatives.

[0003] Common pigment derivatives are pigment derivatives containing phthalimide structures. Patent document CN107430224A discloses a color filter prepared from a phthalocyanine pigment composition containing a phthalocyanine derivative with a multi-substituted phthalimide group, the brightness of which is improved, and at the same time, the heat resistance of the prepared color filter is also improved.

[0004] The preparation method of phthalocyanine derivatives containing phthalonitrile disclosed in the current technology is generally to react metal phthalocyanine or substituted metal phthalocyanine with polyformaldehyde and phthalimide in concentrated sulfuric acid. The actual situation is that phthalocyanine is easy to decompose in concentrated sulfuric acid. In particular, when the central atom of phthalocyanine is a zinc atom, zinc phthalocyanine or substituted zinc phthalocyanine has poor stability and will decompose in large quantities in the environment of concentrated sulfuric acid, making the yield of the derivative very low.

[0005] Based on the above technical problems, it is necessary to develop a new phthalocyanine derivative containing phthalimide and a preparation method to improve the yield of the derivative and give the pigment high brightness and high contrast. Summary of the invention

[0006] In view of the above shortcomings of the prior art, the present invention aims to provide a phthalimide phthalocyanine derivative and a preparation method thereof, a pigment composition and application thereof.

[0007] To achieve the above objectives, the technical solutions adopted are:

[0008] One of the purposes of the present invention is to provide a phthalimide phthalocyanine derivative having a structure shown in Formula I:

[0009]

[0010] Wherein, M is a metal atom, L is a bridging group, and n is an integer of 1-8.

[0011] Preferably, the metal atom is Cu or Zn, more preferably Zn.

[0012] Preferably, the bridging group is any one of a), b), c), d) of Formula II:

[0013]

[0014] The second object of the present invention is to provide a method for preparing the above-mentioned phthalimide phthalocyanine derivatives. The method comprises first preparing phthalocyanine fragments containing phthalimide structures, and then assembling them into phthalocyanine derivatives. Specifically, the method may be any one of the following methods.

[0015] Method 1: Prepare a phthalonitrile intermediate containing aniline, react it with hydroxymethylphthalimide to prepare a phthalonitrile phthalocyanine fragment containing phthalimide, and then react it with a metal salt under the action of a catalyst to prepare a metal phthalocyanine derivative.

[0016] Method 2: Hydroxymethylphthalimide is reacted with a hydroxylated aromatic ring to prepare an intermediate, which is then reacted with nitro-containing phthalonitrile to prepare a phthalonitrile phthalocyanine fragment containing phthalimide, and then reacted with a metal salt under the action of a catalyst to prepare a metal phthalocyanine derivative. The hydroxylated aromatic ring includes but is not limited to a phenyl aromatic ring and a naphthyl aromatic ring.

[0017] Preferably, the method 1 specifically comprises the following steps:

[0018] (a) adding nitrophthalonitrile, p-aminophenol and potassium carbonate to an N,N-dimethylformamide (DMF) solution, and reacting at a certain temperature to prepare phthalonitrile containing aniline; wherein the molar ratio of nitrophthalonitrile, p-aminophenol and potassium carbonate is 1:(1-3):(1-3), the reaction temperature is 10-100° C., and the reaction time is 2-48 h;

[0019] (b) adding hydroxymethylphthalimide to an 80% by mass ethanol aqueous solution, heating to boiling, then adding phthalonitrile containing aniline, reacting for 0.5-24 hours, cooling to room temperature, filtering, washing, and drying to obtain phthalonitrile units containing phthalimide;

[0020] (c) Phthalonitrile unit containing phthalimide, phthalonitrile and metal salt are mixed in a solvent and a catalyst, and reacted at a certain temperature to obtain a phthalocyanine derivative containing phthalimide. Wherein, the metal salt is zinc chloride, zinc acetate or cuprous chloride, the molar ratio of phthalonitrile containing phthalimide, phthalonitrile and metal salt is 1: (0-10): (0.2-3), the reaction temperature is 130-220°C, and the reaction time is 2-24h; the solvent is preferably n-pentanol, n-heptanol, nitrobenzene, o-dichlorobenzene, trichlorobenzene. When the solvent is n-pentanol or n-heptanol, the catalyst is preferably DBU (1,8-diazabicyclo[5.4.0]undec-7-ene); when the solvent is nitrobenzene, o-dichlorobenzene or trichlorobenzene, the catalyst is preferably ammonium molybdate.

[0021] Method 2 specifically includes the following steps:

[0022] (d) reacting hydroxymethylphthalimide with hydroxylated aromatic rings in concentrated sulfuric acid to prepare an intermediate containing hydroxyl and phthalimide units, wherein the molar ratio of hydroxymethylphthalimide to hydroxylated aromatic rings is (10-0.1):1, the reaction temperature is 0-120°C, and the reaction time is 4-48h;

[0023] (e) reacting the hydroxyl-containing and phthalimide-containing intermediate with nitrophthalonitrile to prepare a phthalocyanine fragment, wherein the specific steps are as described in (a) of the above method 1;

[0024] (f) preparing a phthalocyanine derivative from phthalonitrile containing phthalimide units, the specific steps are as described in (c) of the above method 1.

[0025] The third object of the present invention is to provide a pigment composition comprising the phthalimide phthalocyanine derivative and the phthalocyanine pigment.

[0026] Preferably, the mass ratio of the phthalimide phthalocyanine derivative to the phthalocyanine pigment is 0.1-50:100, preferably 0.1-10:100.

[0027] Preferably, the phthalocyanine pigment is any one of CI Pigment Blue 15, CI Pigment Blue 15:1, CI Pigment Blue 15:3, CI Pigment Blue 15:6, CI Pigment Green 7, CI Pigment Green 36, and CI Pigment Green 58.

[0028] Preferably, the pigment composition is prepared by mechanical mixing or kneading or a combination of the two.

[0029] The mechanical mixing refers to a method of mixing the phthalimide phthalocyanine derivative and the phthalocyanine pigment in a mixing device at a certain temperature for a certain time. The mixing device can be a mixer, a roller burnisher, an ultrafine grinder, etc. The mixing time is 1-100 hours and the mixing temperature is 0-200°C.

[0030] The kneading is a method of putting phthalocyanine pigment, phthalimide phthalocyanine derivative, inorganic salt and organic solvent into a kneading device for mixing and kneading. The kneading device used can be a kneader, a ball mill, a bead mill, a sand mill, an ultrafine crusher, etc.

[0031] The inorganic salt may be a water-soluble inorganic salt, such as sodium chloride, potassium chloride, sodium sulfate, etc. The particle size of the inorganic salt is 0.5-50 μm. The amount of the inorganic salt used, by weight, may be 1-100 parts, preferably 5-20 parts, relative to 1 part of the phthalocyanine pigment.

[0032] As the organic solvent, a water-soluble organic solvent can be used, for example, ethylene glycol, diethylene glycol, propylene glycol, glycerol, liquid polyethylene glycol, liquid polypropylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, etc. The amount of the organic solvent used, in parts by weight, can be 0.01-20 parts, preferably 1-10 parts, relative to 1 part of the phthalocyanine pigment.

[0033] The kneading temperature may be between 20 and 150° C. The kneading time may be between 1 and 100 hours.

[0034] After kneading, the material is put into a large amount of water, filtered, washed and dried to obtain the pigment composition of the present invention.

[0035] A fourth object of the present invention is to provide an application of the pigment composition, wherein the pigment composition is applied to the fields of color filters, inks, coatings, plastics, etc.

[0036] Compared with the prior art, the present invention has the following beneficial effects:

[0037] (1) The yield of phthalimide derivatives is greatly improved, and has greater industrial value;

[0038] (2) The types of phthalimide derivatives are enriched, and pigment compositions with excellent performance can be optimized. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1is the MALDI-TOF mass spectrum of derivative 1;

[0040] Figure 2 is the MALDI-TOF mass spectrum of derivative 2;

[0041] Figure 3 2 are XRD patterns of pigment composition 2 and comparative pigment 2;

[0042] Figure 4 This is the MALDI-TOF mass spectrum of derivative 3. DETAILED DESCRIPTION

[0043] The following specific embodiments illustrate the implementation of the present invention, and those skilled in the art can easily understand other advantages and effects of the present invention from the contents disclosed in this specification. Although the description of the present invention will be introduced in conjunction with the preferred embodiment, this does not mean that the features of this invention are limited to this implementation. On the contrary, the purpose of introducing the invention in conjunction with the implementation is to cover other options or modifications that may extend based on the claims of the present invention. In order to provide a deep understanding of the present invention, the following description will include many specific details. The present invention can also be implemented without using these details. In addition, in order to avoid confusion or blurring the focus of the present invention, some specific details will be omitted in the description. It should be noted that the embodiments of the present invention and the features in the embodiments can be combined with each other without conflict.

[0044] Embodiment 1

[0045] 1. Synthesis of derivative 1

[0046] Derivative 1 has the structure shown below, wherein n = 1-4;

[0047]

[0048] To prepare intermediate 1, 50 g of 80% ethanol aqueous solution was heated to 80°C, 7.53 g of N-hydroxymethylbenzimide was added, stirred to dissolve, and then 4.53 g of 4-aminophthalonitrile was added. After reacting for 4 hours, the temperature was lowered, filtered, and the solid was recrystallized from ethanol / water solution to obtain 5.82 g of intermediate 1, with a yield of 61%.

[0049]

[0050] In a three-necked flask equipped with a mechanical stirrer, a condenser, and a thermometer, add 100 ml of nitrobenzene, 2.43 g of zinc chloride, 4.16 g of phthalonitrile, 5.00 g of intermediate 1, and 0.5 g of ammonium molybdate, heat to 190-200°C, keep warm for 5 hours, cool to 80°C, and filter while hot. Wash the filter cake with a small amount of hot nitrobenzene, then with methanol until the filtrate is colorless, then wash with 5% hot hydrochloric acid, water, and methanol, respectively, and finally dry at 70°C to obtain 6.18 g of dark green solid. The MALDI-TOF mass spectrometer detected five molecular ion peaks, corresponding to unsubstituted zinc phthalocyanine (theoretical molecular weight 576.08, measured molecular weight 576.01), monosubstituted zinc phthalocyanine (theoretical molecular weight 750.12, measured molecular weight 750.05), disubstituted zinc phthalocyanine (theoretical molecular weight 924.16, measured molecular weight 924.09), trisubstituted zinc phthalocyanine (theoretical molecular weight 1098.21, measured molecular weight 1098.15), and tetrasubstituted zinc phthalocyanine (theoretical molecular weight 1272.25, measured molecular weight 1272.19), as shown in Figure 5. Figure 1 shown.

[0051] 2. Preparation of Pigment Composition 1

[0052] Add 80g Pigment Green 58, 2.4g Derivative 1, 800g sodium chloride, and 120g diethylene glycol into a kneader, maintain the temperature at 80°C, and knead for 24h. Pour the kneaded material into water, wash with water until the conductivity is the same as that of water, and dry the material to obtain a pigment composition 1.

[0053] As a comparison, 82.4 g of Pigment Green 58, 800 g of sodium chloride, and 120 g of diethylene glycol were added to a kneader, the temperature was maintained at 80°C, and stirred for 24 hours. The kneaded material was poured into water, washed with water until the conductivity was the same as that of water, and the material was dried to obtain comparative pigment 1.

[0054] Pigment composition evaluation

[0055] (1) Material ratio

[0056]

[0057]

[0058] (2) Color paste preparation

[0059] Add the above-mentioned materials in order into a glass bottle, add 150 g of 0.3 mm zirconium balls, put the glass bottle into a shaker and shake for 24 hours, filter out the zirconium balls, and obtain the evaluation composition color paste 1.

[0060] As a comparison, comparative pigment 1 was used to replace pigment composition 1 in the above formula to prepare comparative color paste 1.

[0061] (3) Color paste evaluation

[0062] The particle size of nano pigment in the color paste was tested by a particle size analyzer, and the results are shown in Table 1;

[0063] Take 1 mL of the color paste and spin-coat it on a glass slide at a speed of 600 rpm. Place the coated glass slide on a hot plate at 90°C for 3 minutes and then place it in a 230°C oven for 30 minutes. Use a colorimeter and a contrast meter to test the color coordinates and contrast. The results are shown in Table 1.

[0064] Table 1. Comparison of color paste properties of Example 1 and Comparative Example 1

[0065] Sample name Viscosity D50(nm) D90(nm) Brightness Y Contrast Example 1 3.34 53.07 72.84 61.06 18284 Comparative Example 1 3.96 72.43 114.94 57.23 6901

[0066] As shown in Table 1, after adding derivative 1 to the pigment composition of Example 1, the viscosity of the prepared color paste is reduced, the particle size (D50, D90) is reduced, and the brightness Y and contrast are increased, which indicates that the pigment composition containing derivative 1 has excellent performance.

[0067] Embodiment 2

[0068] 1. Synthesis of derivative 2

[0069] Derivative 2 has the following structure,

[0070]

[0071] (1) Preparation of phthalonitrile intermediate containing aniline (intermediate 2)

[0072]

[0073] Add 200g DMF, 40g 4-nitrophthalonitrile, and 27.6g p-aminophenol into a 500mL three-necked flask, stir to dissolve, add 70g anhydrous potassium carbonate, heat to 50°C and react for 24h. Pour the material into 2000L ice water, adjust the pH to neutral, filter, and recrystallize from ethanol to obtain 9.43g of brown-grey product with a yield of 75.8%.

[0074] (2) Preparation of phthalonitrile intermediate containing phthalimide (Intermediate 3)

[0075]

[0076] 50 g of 80% ethanol aqueous solution was heated to 80° C., 6.33 g of N-hydroxymethylbenzimide was added, stirred to dissolve, and then 7.00 g of intermediate 2 was added. After reacting for 6 h, the temperature was lowered, filtered, and washed to obtain 6.64 g of intermediate 3 with a yield of 56.6%.

[0077] (3) Preparation of Pigment Derivative 2

[0078]

[0079] In a three-necked flask equipped with a mechanical stirrer, a condenser, and a thermometer, add 100 ml of nitrobenzene, 1.90 g of cuprous chloride, 3.25 g of phthalonitrile, 5.00 g of intermediate 3, and 0.5 g of ammonium molybdate, heat to 190-200°C, keep warm for 5 hours, cool to 80°C, and filter while hot. The filter cake is washed with a small amount of hot nitrobenzene, and then washed with methanol until the filtrate is colorless, and then washed with 5% hot hydrochloric acid, water, and methanol, respectively, and finally dried at 70°C to obtain 5.54 g of dark green solid. MALDI-TOF mass spectrometry detected three molecular ion peaks, corresponding to unsubstituted zinc phthalocyanine (theoretical molecular weight 575.08, measured molecular weight 575.01), monosubstituted zinc phthalocyanine (theoretical molecular weight 841.15, measured molecular weight 841.06), disubstituted zinc phthalocyanine (theoretical molecular weight 1107.22, measured molecular weight 1107.11), such as Figure 2 shown.

[0080] 2. Preparation of Pigment Composition 2

[0081] Add 80g of Pigment Blue 15:1, 4g of Derivative 2, 800g of sodium chloride, and 120g of diethylene glycol into a kneader, maintain the temperature at 80°C, and knead for 24h. Pour the kneaded material into water, wash with water until the conductivity is the same as that of water, and dry the material to obtain a pigment composition 2. Test the XRD pattern of the pigment composition 2. Figure 3 shown.

[0082] For comparison, add 84g of pigment blue 15:1, 800g of sodium chloride, and 120g of diethylene glycol into the kneader, maintain the temperature at 80°C, and stir for 24h. Pour the kneaded material into water, wash with water until the conductivity is the same as that of water, and dry the material to obtain comparative pigment 2. Test the XRD pattern of comparative pigment 2, as shown in Figure 3 As shown. Figure 3 It can be seen that the pigment combination 2 is transformed into the ∈ crystal form, while the comparative pigment 2 is still the α crystal form.

[0083] 3. Evaluation of pigment composition

[0084] (1) Material ratio

[0085]

[0086] (2) Color paste preparation

[0087] Add the above-mentioned materials in order into a glass bottle, add 150 g of 0.3 mm zirconium balls, put the glass bottle into a shaker and shake for 24 hours, filter out the zirconium balls, and obtain the evaluation composition - color paste 2.

[0088] As a comparison, comparative pigment 2 was used to replace pigment composition 2 in the above formula to prepare comparative color paste 2.

[0089] (3) Color paste evaluation

[0090] The particle size of the nano pigment in the color paste was tested using a particle size analyzer, and the data is shown in Table 2.

[0091] 1 mL of the color paste was taken and spin-coated on a glass slide at a speed of 600 rpm. The coated glass slide was placed on a heating plate at 120°C for 2 min and then placed in an oven at 230°C for 30 min. The brightness and contrast were tested. The results are shown in Table 2.

[0092] Table 2. Comparison of color paste properties of Example 2 and Comparative Example 2

[0093]

[0094] As can be seen from Table 2, after adding the pigment derivative in Example 2, the viscosity becomes smaller, the particle size becomes smaller, and the brightness and contrast of the color paste are significantly improved.

[0095] Embodiment 3

[0096] 1. Synthesis of derivative 3

[0097]

[0098] (1) Preparation of intermediate 4 by reaction of hydroxymethylphthalimide with phenol

[0099]

[0100] 37.6 g of hydroxymethylphthalimide and 10.0 g of phenol were added to 50 g of THF, and 300 g of concentrated sulfuric acid was slowly added after stirring for 30 minutes, and stirred at room temperature for 24 hours. The system was poured into ice water, filtered, washed, and dried to obtain 23.48 g of a white product with a yield of 87.2%.

[0101] (2) The intermediate 4 is reacted with 4-nitrophthalonitrile to prepare the phthalonitrile intermediate 5 containing phthalimide.

[0102]

[0103] In a 250mL three-necked flask, add 100g DMF, 10.0g 4-nitrophthalonitrile, and 16.0g intermediate 4, stir to dissolve, add 17g anhydrous potassium carbonate, heat to 80°C and react for 24h. Pour the material into 1000L ice water, adjust the pH to neutral, filter, and recrystallize from ethanol to obtain 7.68g of the product, with a yield of 76.8%.

[0104] (3) Preparation of Pigment Derivative 3

[0105] In a three-necked flask equipped with a mechanical stirrer, a condenser, and a thermometer, 100 ml of nitrobenzene and 1.0 g of zinc chloride were added, heated to 100°C, and then 10 g of intermediate 5 and 1 g of ammonium molybdate were added, and the mixture was heated to 190-200°C, kept warm for 5 hours, cooled to 80°C, and filtered while hot. The filter cake was washed with a small amount of hot nitrobenzene, and then washed with methanol until the filtrate was colorless, and then washed with 5% hot hydrochloric acid, water, and methanol, respectively, and finally dried at 70°C to obtain 7.12 g of derivative 3, with a yield of 68.37%. The molecular weight was 1580.82 (theoretical value 1580.31) according to MALDI-TOF mass spectrometry.

[0106] 2. Preparation of Pigment Composition 3

[0107] 80 g of Pigment Green 58, 2.4 g of Derivative 3, 800 g of sodium chloride, and 120 g of diethylene glycol were added to a kneader, and the temperature was maintained at 80° C. and kneaded for 24 h. The kneaded material was poured into water, washed with water until the conductivity was the same as that of water, and the material was dried to obtain a pigment composition 3.

[0108] As a comparison, 82.4 g of Pigment Green 58, 800 g of sodium chloride, and 120 g of diethylene glycol were added to a kneader, maintained at 80°C, and stirred for 24 hours. The kneaded material was poured into water, washed with water until the conductivity was the same as that of water, and dried to obtain comparative pigment 3.

[0109] 3. Evaluation of pigment composition

[0110] (1) Material ratio

[0111]

[0112] (2) Color paste preparation

[0113] Add the above-mentioned materials in order into a glass bottle, add 150 g of 0.3 mm zirconium balls, put the glass bottle into a shaker and shake for 24 hours, filter out the zirconium balls, and obtain the evaluation composition - color paste 3.

[0114] As a comparison, comparative pigment 3 was used to replace pigment composition 3 in the above formula to prepare comparative color paste 3.

[0115] (3) Color paste evaluation

[0116] The particle size of the nano pigment in the color paste was tested using a particle size analyzer, and the results are shown in Table 3.

[0117] 1 mL of the color paste was taken and spin-coated on a glass slide at a speed of 600 rpm. The coated glass slide was placed on a heating plate at 120°C for 2 min and then placed in an oven at 230°C for 30 min. The brightness and contrast were tested. The results are shown in Table 3.

[0118] Table 3. Comparison of color paste properties of Example 3 and Comparative Example 3

[0119] Sample name Viscosity D50(nm) D90(nm) Brightness Y Contrast Example 3 3.37 55.80 74.56 61.49 17404 Comparative Example 3 3.96 72.43 114.94 57.23 6901

[0120] As can be seen from Table 3, after adding the pigment derivative in Example 3, the viscosity becomes smaller, the particle size becomes smaller, and the brightness and contrast of the color paste are significantly improved.

[0121] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims

1. A phthalimide phthalocyanine derivative, characterized in that: It has the structure shown in Formula I: Wherein, M is a metal atom, L is a bridging group, and n is an integer of 1-8.

2. The phthalimide phthalocyanine derivative according to claim 1, characterized in that: The metal atom is Cu or Zn; The bridging group is any one of a), b), c), and d) of Formula II:

3. A method for preparing a phthalimide phthalocyanine derivative according to any one of claims 1 to 2, characterized in that: The method comprises the following steps: firstly preparing phthalocyanine fragments containing phthalimide structures, and then assembling them into phthalocyanine derivatives.

4. The method for preparing the phthalimide phthalocyanine derivative according to claim 3, characterized in that: The method comprises the following steps: firstly preparing a phthalonitrile intermediate containing aniline, then reacting with hydroxymethylphthalimide to prepare a phthalonitrile phthalocyanine fragment containing phthalimide, and then reacting with a metal salt under the action of a catalyst to prepare a metal phthalocyanine derivative.

5. The method for preparing a phthalocyanine derivative according to claim 3, characterized in that: The method comprises the following steps: reacting hydroxymethylphthalimide with a hydroxylated aromatic ring to prepare an intermediate, reacting the intermediate with phthalonitrile containing a nitro group to prepare a phthalonitrile phthalocyanine fragment containing phthalimide, and then reacting the intermediate with a metal salt under the action of a catalyst to prepare a metal phthalocyanine derivative.

6. The method for preparing a phthalocyanine derivative according to claim 5, characterized in that: The hydroxylated aromatic ring is a phenyl aromatic ring or a naphthyl aromatic ring.

7. A pigment composition, characterized in that The invention comprises the phthalimide phthalocyanine derivative according to any one of claims 1 to 2 and a phthalocyanine pigment.

8. The pigment composition according to claim 7, characterized in that The mass ratio of the phthalimide phthalocyanine derivative to the phthalocyanine pigment is 0.1-50:

100.

9. The pigment composition according to claim 7, characterized in that The phthalocyanine pigment is any one of CI Pigment Blue 15, CI Pigment Blue 15:1, CI Pigment Blue 15:3, CI Pigment Blue 15:6, CI Pigment Green 7, CI Pigment Green 36, and CI Pigment Green 58.

10. Use of the pigment composition according to any one of claims 7 to 9, characterized in that: The pigment composition is applied to the fields of color filters, inks, coatings and plastics.

Images