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Fluorine-based surfactant, coating composition, resist composition, and cured product

A surfactant, fluorine-based technology, applied in the direction of coating, pattern surface photoengraving process, instruments, etc., can solve the problem of uneven abnormal detection, inability to distinguish between normal and abnormal products, and finished color filter products rate reduction, etc.

Active Publication Date: 2016-11-09
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when the colored pattern obtained using the color filter pixel-forming composition described in Patent Document 1 is exposed to the alkaline developing solution used in the aforementioned developing step, there is a phenomenon that the colored pattern (coating film) discolors ( water stains)
This type of water stain disappears after post-baking, so there is no problem with the product, but in the visual inspection of the patterned surface after development, it is detected as unevenness, and there is a problem that normal products cannot be distinguished from abnormal products.
Therefore, if the inspection sensitivity of the inspection device is lowered in the visual inspection, the yield of the final color filter product will decrease as a result, which becomes a problem.

Method used

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  • Fluorine-based surfactant, coating composition, resist composition, and cured product
  • Fluorine-based surfactant, coating composition, resist composition, and cured product
  • Fluorine-based surfactant, coating composition, resist composition, and cured product

Examples

Experimental program
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preparation example Construction

[0155] Examples of the method for preparing the pigment dispersion include a method through (3) a colorant kneading and dispersing step and a fine dispersion step, a method using only the fine dispersion step, and the like. In the above-mentioned kneading and dispersing step, (3) a colorant, (1) part of the alkali-soluble resin, and if necessary, the above-mentioned dispersant are mixed and kneaded. The machinery used for kneading can be enumerated: two-roll mill, three-roll mill, ball mill, drum sieve, disperser, kneader, compound motion kneader, homogenizer, mixer, single-screw or twin-screw extruder etc., by using these kneaders to disperse while applying a strong shearing force, the colorant can be dispersed. In addition, for the (3) coloring agent, it is preferable to refine the particle size by a salt mill method or the like before performing the above-mentioned kneading.

[0156] On the other hand, in the fine dispersion step, a solvent is added to the composition cont...

Embodiment 1

[0169] Example 1 (synthesis of fluorosurfactant)

[0170] 47.5 g of 2-propanol as a solvent and 25.6 g of 3-hydroxy-1-adamantyl methacrylate were put into the nitrogen-substituted flask, and it heated up to 40 degreeC, stirring under nitrogen flow. Next, 5.3 g of 2,2'-bipyridine and 1.9 g of cuprous chloride were charged, and stirred for 30 minutes while keeping the inside of the flask at 40°C. Then, 3.3 g of ethyl 2-bromoisobutyrate was added and reacted at 40° C. for 2 hours under a nitrogen stream to obtain a polymer segment having a bridged ring hydrocarbon skeleton. Next, 45.9 g of 2-(tridecafluorohexyl)ethyl methacrylate was added to the reaction system containing the polymer segment, and reacted at 40° C. for 5 hours to obtain a reactant. Next, 30 g of activated alumina was added to the obtained reactant and stirred. After filtering activated alumina, the solvent was distilled off under reduced pressure to obtain the fluorine-based surfactant (1) of the present invent...

Embodiment 2

[0171] Embodiment 2 (same as above)

[0172] 81.7 g of 2-propanol as a solvent and 40.5 g of 3-hydroxy-1-adamantyl methacrylate were charged into the nitrogen-substituted flask, and the temperature was raised to 40° C. while stirring under a nitrogen stream. Next, 7.3 g of 2,2'-bipyridine and 1.5 g of cuprous chloride were charged, and stirred for 30 minutes while keeping the inside of the flask at 40°C. Then, 2.5 g of ethyl 2-bromoisobutyrate was added and reacted at 40° C. for 2 hours under a nitrogen stream to obtain a polymer segment having a bridged ring hydrocarbon skeleton. Next, 13.7 g of 2-(tridecafluorohexyl)ethyl methacrylate was added to the reaction system containing this polymer segment, and the mixture was reacted at 40° C. for 5 hours to obtain a reactant. Next, 30 g of activated alumina was added to the obtained reactant and stirred. After filtering activated alumina, the solvent was distilled off under reduced pressure to obtain the fluorine-based surfactan...

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Abstract

The objective of the present invention is to provide: a fluorine-based surfactant that obtains a coating film that does not easily change color (does not easily form water stains) even if exposed to alkaline solutions or acidic solutions. The fluorine-based surfactant is characterized by being a block copolymer containing: a polymer segment (A1) obtained using polymerizable monomers including a polymerizable monomer (a1) having a polymerizable unsaturated group and a fluorinated alkyl group having 1-6 carbon atoms to which a fluorine atom is directly bonded; and a polymer segment (A2) obtained using polymerizable monomers including a polymerizable monomer (a2) having a polymerizable unsaturated group and a bridged cyclic hydrocarbon skeleton.

Description

technical field [0001] The present invention relates to a fluorine-based surfactant capable of obtaining a coating film that does not easily change color (susceptible to water spotting) even when exposed to an alkaline solution or an acidic solution, and a coating composition and a protective agent ( resist) compositions and cured products of these compositions. Background technique [0002] Color filters used in color liquid crystal display devices and organic EL display devices generally have red (R), green (G), and blue (B) pixels, and a black matrix is ​​formed between them for the purpose of improving display contrast. (BM) basic structure. In production of a color filter, generally, a protective agent composition is applied on a glass substrate by a coating method such as spin coating or slit coating, dried, exposed using a mask, and then developed to form a colored pattern. [0003] The above-mentioned development uses an alkaline developing solution as a developing...

Claims

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Application Information

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IPC IPC(8): C08F293/00C09D7/12C09D201/00G02B5/20G03F7/004
CPCG02B5/20G03F7/0007G03F7/0046G03F7/0048C08F293/005C09D7/40C08F20/18C08F20/22C08F2/30C08F220/1811C08F220/1818C09D7/65C08F8/24C08F32/00C09D201/00
Inventor 清水良平笹本慎高野启
Owner DIC CORP