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Coumarin compound, pigment composition, color resist, and inkjet ink composition

A pigment composition and compound technology, applied in the direction of coumarin dyes, applications, inks, etc., can solve the problems of insufficient pigment dispersion, unstable quality of pigment dispersion liquid, difficulty in controlling the number and position of substituents, etc., and achieve easy manufacturing Effect

Pending Publication Date: 2019-10-11
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in these methods, it is difficult to control the number and position of substituents introduced into pigments whose structure is difficult to introduce sulfone groups, aminomethyl groups, phthalimidomethyl groups, etc.
As a result, the dispersion of the pigment becomes insufficient, and even a large amount of by-products that adversely affect the color tone are generated, and there are inconveniences such as unstable quality of the pigment dispersion liquid.
[0008] In addition, the pigment composition using Pigment Red (PigmentRed) 254, which has been widely used as a red pigment for color filters, has the problem of improving the transmittance.

Method used

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  • Coumarin compound, pigment composition, color resist, and inkjet ink composition
  • Coumarin compound, pigment composition, color resist, and inkjet ink composition
  • Coumarin compound, pigment composition, color resist, and inkjet ink composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1 (synthesis of the compound shown in No.2 of the specific example compound)

[0084] After dissolving 15.5 parts of C.I. Acid Yellow 184 in 300 parts of water in a reaction vessel, add concentrated hydrochloric acid to the solution at 20 to 30°C to set the pH to 0.5 to 1.0, and stir for a while at the same temperature / pH. Hour. The wet cake obtained by filtering the precipitated crystal was dried with an 80° C. hot air dryer to obtain 10.5 parts of the compound shown in Specific Example Compound No. 2. The maximum absorption wavelength λmax of this compound is 440 nm (NMP).

Synthetic example 1

[0085] Synthesis Example 1 (Preparation of Binder Resin A)

[0086] In a 500ml four-necked flask, 160 parts of methyl ethyl ketone, 10 parts of methacrylic acid, 33 parts of benzyl methacrylate, 1 part of α, α'-azobis (isobutyronitrile ), nitrogen was flowed into the flask for 30 minutes while stirring. Thereafter, the temperature was raised to 80° C., and the mixture was stirred at 80 to 85° C. for 4 hours. After the reaction, it was cooled to room temperature to obtain a colorless, transparent and uniform binder resin solution. It was made to precipitate in the 1:1 mixed solution of isopropanol and water, it filtered, the solid content was taken out, and it dried, and binder resin A was obtained. The obtained binder resin A had a polystyrene equivalent weight average molecular weight of 18,000 and an acid value of 152.

Embodiment 2

[0087] Embodiment 2 (preparation of the pigment composition of the present invention)

[0088] 10.0 parts of C.I. Pigment Red 254 as the organic pigment, 1.0 parts of the compound shown in No. 2 obtained in Example 1 as the compound of the present invention, and 1.8 parts of the adhesive obtained in Synthesis Example 1 as the binder resin. Mixture resin A, 10.0 parts of AJISPERPB881 (manufactured by Ajinomoto Fine-Techno Co., Ltd.) as a resin dispersant, and 82 parts of propylene glycol monomethyl ether acetate as a solvent were prepared, pre-mixed, and 0.3 mm of zirconia was used Beads were dispersed with a paint shaker for 60 minutes. The obtained dispersion was filtered through a 5 μm filter to prepare the pigment composition of the present invention.

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PUM

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Abstract

The invention relates to a coumarin compound and a pigment composition containing the coumarin compound. One of the problems to be solved by the present invention is to provide a pigment composition (pigment dispersion liquid) which is stable as a colorant for photoresists and inkjet inks for color filters without causing agglomeration, sedimentation, and increase in viscosity over time and in which an organic pigment is micronized and concentrated in concentration. The present invention for solving the problem is described below. The coumarin compound is represented by formula (1). In formula(1), R1 and R2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R3 to R10 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom, a carboxyl group or a sulfonic acid group, but at least one of R7 to R10 is a sulfonic acid group; X represents an oxygen atom, a sulfur atom or a divalent linking group-NR11-; and R11 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

Description

technical field [0001] The present invention relates to a coumarin compound (including its salt) suitable as a photoresist for color filters used in the manufacture of liquid crystal displays, imaging devices, etc., and inkjet printing inks; And a pigment composition excellent in transparency. Background technique [0002] Pigments are used as paints and printing inks, and in recent years they are used as colorants in photoresists for color filters and inkjet inks. Among properties such as heat resistance, weather resistance, and migration resistance, pigments are superior in terms of fastness compared to dyes. On the other hand, pigments have potential inconveniences such as agglomeration, sedimentation, viscosity increase over time, and color separation when mixed with different pigments when they are made into a composition. [0003] In addition, recently, in order to achieve high contrast of liquid crystal displays, miniaturization of imaging elements, high coloring an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C09B57/02C09B67/22G03F7/004G03F7/027C09D11/30C09D11/38
CPCC07D405/04C09B57/02C09B67/0033C09B67/0097G03F7/004G03F7/027C09D11/30C09D11/38C09B57/004G03F7/105C09D11/328C09D11/36G03F7/032
Inventor 吉本隆志竹内理恵龟谷纮
Owner NIPPON KAYAKU CO LTD
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