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Novel compound and radiation sensitive composition comprising the same

A technology of compound and carbon number, which is applied in the field of radiation-sensitive compositions, can solve the problems of not considering the transparency of the cured film, insufficient solubility, etc., and achieve the effects of good solubility, pollution inhibition, and high transparency

Active Publication Date: 2011-08-24
JSR CORPORATIOON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since this oxime ester compound is a photoinitiator for forming a colored resist film, the transparency of a cured film using this photoinitiator is not considered.
In addition, it is considered that the above-mentioned oxime ester compounds have insufficient solubility in radiation-sensitive compositions, and there is room for improvement.

Method used

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  • Novel compound and radiation sensitive composition comprising the same
  • Novel compound and radiation sensitive composition comprising the same
  • Novel compound and radiation sensitive composition comprising the same

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0119]

[0120] The radiation-sensitive composition of the present invention can be prepared by well-mixing the aforementioned [A] photopolymerization initiator, [B] the polymerizable compound having an ethylenically unsaturated double bond, and the aforementioned other optional components. The radiation-sensitive composition is preferably used in a solution state dissolved in an appropriate solvent. For example, a radiation-sensitive composition in a solution state can be prepared by mixing [A] a photopolymerization initiator, [B] a polymerizable compound having an ethylenically unsaturated double bond, and other components optionally added in a solvent at a predetermined ratio. .

[0121] As the solvent used in the preparation of the radiation-sensitive composition, each component capable of uniformly dissolving [A] the photopolymerization initiator, [B] the polymerizable compound having an ethylenically unsaturated double bond, and other optional components can be used. ...

Synthetic example A-1

[0151][Synthesis Example A-1] (Synthesis of Compound (A-1))

[0152] Compound (A-1) (compound represented by the above formula (2)) was synthesized as the final product (viii) according to the following synthesis route.

[0153]

[0154] In the formula, Me is a methyl group, and Ac is an acetyl group.

[0155] Step (I): Synthesis of intermediate (ii) by condensation of 1-(4-fluorophenyl)-oct-1-one (i) and carbazole

[0156] A cooling tube was installed in a 1 L three-necked flask, and 50 g (299 mmol) of carbazole was dissolved in 500 mL of dimethyl sulfoxide under a nitrogen atmosphere. 63 g (284 mmol) of 1-(4-fluorophenyl)-oct-1-one and 103 g (748 mmol) of potassium carbonate were added thereto, and heated and stirred at a reaction temperature of 135° C. for 12 hours. The reaction solution was poured into ice, the precipitated solid was suction filtered, and the solid was washed with distilled water. The crude crystals obtained here were recrystallized from tert-butyl m...

Synthetic example A-2

[0182] [Synthesis Example A-2] (Synthesis of Compound (A-2))

[0183] The compound represented by the above formula (4) is synthesized by changing the synthesis route of the above (A-1). In the step (II) of the synthetic route of above-mentioned (A-1), in the eggplant type flask of 200mL, add the 4-trimethylsilyl-2-methylbenzoic acid of 33.7g (162mmol) and 193g (1620mmol) ) thionyl chloride, stirred at room temperature 25°C, and then, 1 mL of dimethylformamide was added, followed by stirring for 20 hours. The reaction liquid was distilled off under reduced pressure to obtain 36.7 g of 4-trimethylsilyl-2-methylbenzoyl chloride.

[0184] In a 2L eggplant-shaped flask, add 59.8g (162mmol) of the intermediate (ii) obtained above, then add 1000mL of dichloromethane to dissolve the intermediate (ii), add 75.6g (567mmol) of aluminum chloride, and pass through the ice After cooling, the temperature of the reaction solution was lowered to 10°C. A solution in which 36.7 g (162 mmol) ...

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Abstract

The invention relates to a novel compound and a radiation sensitive composition comprising the same. The invention aims at providing a novel compound, the compound is characterized by low sublimation, high radiation sensitivity as a photopolymerization initiator, and excellent dissolubility; and aims at providing a radiation sensitive composition capable of forming solidified films advantaged by high surface hardness and transparency. A first scheme is the compound represented by the following formula (I). A second scheme is a radiation sensitive composition, comprising: [A] the compound as the photopolymerization initiator, and [B] a polymerization compound provided with vinyl unsaturated double bonds. The radiation sensitive compound preferably further comprises [C] alkali soluble resin.

Description

technical field [0001] The present invention relates to a novel compound useful as a photopolymerization initiator and a radiation-sensitive composition containing the novel compound. Background technique [0002] Radiation-sensitive compositions are widely used in photocuring in addition to being used as materials for liquid crystal devices and semiconductor devices because they can easily form cured products in large quantities through coating processes, and are easy to microfabricate the cured products. Sex ink, photosensitive printing plate, etc. Such a radiation-sensitive composition typically contains a polymerizable compound having an ethylenically unsaturated bond and a photopolymerization initiator. In the above-mentioned cured product forming process, the radiation-sensitive composition can be coated on a glass substrate or the like to form a coating, and then the coating can be exposed by an exposure device having a mercury lamp to form a cured film as a cured pr...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07F7/10C07F9/28C08F2/48G03F7/004G03F7/027
CPCG03F7/031C07D209/82C07D209/86H10K85/636
Inventor 岩泽晴生一户大吾
Owner JSR CORPORATIOON
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