JP2010008533A - Organic coloring matter for color filter, resist for color filter, and color filter - Google Patents

Abstract

[PROBLEMS] To maintain the dispersibility of a resist in a liquid state, and to leave a decomposition product in the coating film, and to reduce the performance of the coating film, to reduce the mass due to gasification, to the influence of the cured film, such as distortion of the coating film An organic dye for a color filter is provided. Also provided are a color filter resist and a color filter using an organic dye for a color filter.
An organic dye in which a side chain is broken at the time of exposure to a resist coating film or during post-baking, and an anion is generated by an acrylic acid derivative represented by the chemical formula (1) or a chemical formula (2), Acrylic acid derivatives or radicals are generated by the compound represented by the chemical formula (3).
[Selection figure] None

Description

  The present invention relates to an organic dye for a color filter of a display device, a resist using the same, and a color filter. In particular, the dispersibility of the resist is good, and the effect on a cured film due to deterioration in coating film performance or gasification. The present invention relates to an organic dye for a color filter with a small amount.

  The quality required for a color filter for a display device includes brightness, color characteristics, pattern shape, uniformity, developability, and the like. Improvement in brightness is important, and research is being conducted daily on resist materials for each color used in the manufacture of color filters. In most cases, the colorant used for each color resist is a pigment, and a dispersant is added to improve the dispersibility. However, it is difficult to satisfy the required quality such as the brightness and color characteristics of the color filter with one type of pigment corresponding to a certain color of the color filter. A resist having characteristics and the like is made. Since the color filter resist is made by mixing several kinds of pigments, it is difficult to prepare a resist with good dispersibility.

  Conventionally, as a dispersant for resist, for example, as disclosed in Patent Document 1, a dispersant having a pigment structure has been proposed. According to the publication, there are proposed dispersants having various types of pigment structures such as R (red), G (green), B (blue), V (violet), and Y (yellow). However, with these materials, although dispersibility is good, the pigment structure decomposes during exposure by UV irradiation or post-baking by heating, so that decomposition products remain in the coating film, resulting in a decrease in coating film performance and a decrease in mass due to gasification.・ There are concerns about distortion of the coating film.

  On the other hand, as disclosed in Patent Document 2, for example, the invention of the present application is also a device that is a dispersant having a pigment structure and that the decomposition of the pigment structure during post-baking by heating does not affect the coating film. It is done by the person. In Patent Document 2, although it is an invention that uses radical polymerization, the present invention is an invention that uses anionic polymerization.

  Further, as disclosed in, for example, Patent Document 3, the present inventor has devised a dispersant having a pigment structure and that the decomposition of the pigment structure during post-baking by heating does not affect the coating film. It has been broken. In patent document 3, although it is invention using a sulfonate ester, this invention is an invention using carbonate ester.

Patent documents are shown below.
JP 2005-266429 A Japanese Patent Application No. 2006-260308 Japanese Patent Application No. 2007-172002

  The present invention has been made in consideration of the technical background as described above. While maintaining the dispersibility of the color filter resist in the liquid state, a decomposition product remains in the coating film, and the coating film performance is improved. It is an object of the present invention to provide an organic dye for a color filter that has less influence on a cured film, such as a decrease in mass and a decrease in mass due to gasification and distortion of a coating film. It is another object of the present invention to provide a color filter resist containing the organic dye for a color filter and a color filter manufactured using the color filter resist.

  The invention according to claim 1 is a solvent-soluble dye, the side chain is broken at the time of exposure or post-baking of a resist film using the dye, and the acrylic acid derivative represented by the chemical formula (1) or An organic dye for a color filter, wherein an anion represented by the chemical formula (2) is generated.

  Further, in the invention according to claim 2, in the organic dye for a color filter according to the above invention, the generation of the acrylic acid derivative represented by the chemical formula (1) or the anion represented by the chemical formula (2) An organic dye for a color filter, which is caused by a compound represented by the chemical formula (3) as a base.

According to a third aspect of the present invention, in the organic dye for a color filter according to the invention, the colored dye represented by the chemical formula (3) is represented by the chemical formula (4) in which R is represented by C _n H _{2n + 1.} The organic dye for a color filter according to claim 2, wherein the organic dye is used.

  According to a fourth aspect of the present invention, there is provided a color filter resist comprising the organic dye for a color filter according to any one of the first to third aspects.

  The invention according to claim 5 is a color filter manufactured using the color filter resist according to claim 3.

  The organic dye for color filter of the present invention maintains the dispersibility of the resist in the liquid state, and remains decomposed in the coating film, resulting in a decrease in coating film performance, mass reduction due to gasification, and distortion of the coating film. It is an organic dye for color filters that has little effect on the cured film. In addition, the color filter dye of the present invention alone has a good dispersibility in a resist liquid state, and also has a function of dispersing a color filter dye having low dispersibility. By using the organic dye for a color filter of the present invention, it is possible to provide a color filter having little influence on a cured film such as a decrease in coating film performance, a decrease in mass due to gasification, and a distortion of the coating film.

Hereinafter, embodiments of the present invention will be described in detail.
The organic dye for a color filter according to the present invention has an acrylic acid derivative represented by the above chemical formula (1), wherein the side chain is broken at the time of exposure by UV irradiation to the resist coating film using the dye or post-baking by heating. The anion represented by the chemical formula (2) is generated, and the acrylic acid derivative or the anion is generated by the compound represented by the chemical formula (3).

The broken side chain has reactivity, and when an acrylate ester is formed, anionic polymerization starts with moisture in the air and integrates with the coating film. When an anion is generated, it is integrated with the coating film as it is. Therefore, the broken side chain is generally not emitted outside the coating film. According to the present invention, the dispersibility can be enhanced without impairing the color characteristics of the resist, and the side chain decomposed during exposure or post-bake binds to the resin in the coating film, so that the coating film due to residual decomposition products It is possible to obtain a color filter that does not impair the properties of the cured film, such as performance degradation, mass reduction due to gasification, and distortion of the coating film.

Below, the organic pigment | dye for color filters of this invention is demonstrated. The chemical formula (3) is a general formula of the colored dye of the present invention, and Pig is a pigment residue, which indicates a general pigment residue. For example, diketopyrrolopyrrole pigment residue, azo pigment, phthalocyanine pigment, anthraquinone pigment, dioxazine pigment, perylene pigment, indigo pigment, quinophthalone pigment, etc. are used. Absent. R is an alkyl group represented by C _n H _{2n + 1} such as CH ₃ , C ₂ H ₅ , C ₃ H _7, etc. If the carbon number is small, whitening occurs when it is incorporated into the coating film. Preferably, n = 2-22, and more preferably n = 3-8. Further, a plurality of side chains from the pigment structure in the chemical formula (3) may exist.

  Although the example of a specific pigment | dye is shown with a diketopyrrolopyrrole-type pigment by Chemical formula (5), this invention is not limited to these.

  Substances other than the resist pigment used in the present invention include resins and additives. Examples of the resin include thermoplastic resins, thermosetting resins, active energy ray curable resins, and monomers and oligomers are also included. The additive includes a catalyst, a curing agent, an auxiliary agent, a stabilizer, a solvent and the like necessary for each polymerization.

  Desirable resin forms are UV curable resins, such as urethane and epoxy reactive oligomers, pentaerythritol and trimethylolpropane polyfunctional monomers (acrylates and methacrylates), and 1,6-hexanediol. Bifunctional monomers including di (meth) acrylate, ethylene glycol and bisphenol-A, or monofunctional monomers such as isobornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, phenoxyethyl (meth) acrylate, etc. Photopolymerization initiators such as 1-cyclohexyl phenyl ketone, benzyldimethyl ketal, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, diethylthioxanthone, (bis) acylphos Sensitizers such as In'okishido, composed of a solvent or the like. These are not limited to those listed here, and several types may be used in combination.

  Pigments used in the present invention include Pigment Red 177, Pigment Red 254, Pigment Orange 43, Pigment Orange 71, Pigment Green 36, Pigment Yellow 150, Pigment Blue 16 and Pigment Blue P15. Or it can be used even if it mixes several types, However, It is not restricted to these.

  The resist of the present invention is prepared by mixing these substances, but may be pulverized using a pulverizer. Further, the color filter of the present invention can be prepared by a general method, and a black matrix, an overcoat, etc. can be provided as required.

Although the present invention will be described only in the presently most preferred embodiment, the present invention is not limited to this.
<Example 1>
Pigment Red 254 series red resist is prepared, and Pigment Red
What added 60 mass parts of dispersing agents represented by Chemical formula (5) with respect to 100 mass parts of 254 was made into the sample of Example 1, and confirmed that the dispersibility was favorable.

<Comparative Example 1>
Similarly, Pigment Red 254-based red resist was prepared, and 60 parts by mass of the dispersant represented by the chemical formula (6) was added to 100 parts by mass of Pigment Red 254. Was confirmed to be good.

  For evaluation, TG / DTA (differential heat / calorific value simultaneous measurement device) was used, and the weight loss at the aging temperature of the cured film was compared. The prepared cured film was allowed to stand at 20 ° C. for 1 day, weighed 20 mg, sealed with an aluminum pan, held at 20 ° C. for 5 minutes in a nitrogen atmosphere, and then heated to 250 ° C. at 5 ° C./minute.

  Moreover, GC / MS (gas chromatography / mass spectrometer) was used, and the components generated at the aging temperature of the cured film were compared. The prepared cured film was allowed to stand at 20 ° C. for 1 day, and 2 mg was weighed and thermally decomposed at 230 ° C. Helium gas was used for the analysis, the injection temperature was 280 ° C., and m / z = 17 to 550 was measured.

  The results are shown in Table 1. The TG / DTA data shows weight loss from 20 ° C. to 230 ° C., and the GC / MS data shows the total area value of Example 1 relative to Comparative Example 1.

Claims (5)

It is a solvent-soluble dye, and the side chain is broken during exposure or post-baking of a resist film using the dye, and is represented by an acrylic acid derivative represented by the chemical formula (1) or the chemical formula (2) An organic dye for a color filter, wherein an anion is generated.

The formation of the acrylic acid derivative represented by the chemical formula (1) or the anion represented by the chemical formula (2) is caused by the compound represented by the chemical formula (3) having Pig as a pigment residue. Item 1. An organic dye for a color filter according to Item 1.

Formula colored dye represented by formula (3) is, R is C _n H _{2n +} alkyl group of formula represented by ₁ (4) according to claim 2, wherein the color filter for organic dye, characterized in that.

  A color filter resist comprising the organic dye for a color filter according to any one of claims 1 to 3.   A color filter manufactured using the color filter resist according to claim 4.