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Novel compound, radioactive ray sensitivity composition, solidified film and forming method thereof

A compound and radiation technology, used in the manufacture of semiconductor/solid-state devices, photosensitive materials for optomechanical equipment, instruments, etc., can solve the problems of insufficient solubility, insufficient transparency of the cured film, and inability to use, and achieve excellent solubility. , The effect of excellent surface hardness and high transparency

Active Publication Date: 2015-01-21
JSR CORPORATIOON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the above-mentioned oxime ester compound may have a certain absorption band in the visible region, and the transparency of the cured film obtained by using it as a photopolymerization initiator is insufficient.
Therefore, such cured films cannot be used in cured films that require high transparency in the visible region, such as liquid crystal displays.
In addition, the solubility of the above-mentioned oxime ester compound in the radiation-sensitive resin composition is insufficient, and there is room for improvement.

Method used

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  • Novel compound, radioactive ray sensitivity composition, solidified film and forming method thereof
  • Novel compound, radioactive ray sensitivity composition, solidified film and forming method thereof
  • Novel compound, radioactive ray sensitivity composition, solidified film and forming method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0132] (Preparation of radiation-sensitive composition)

[0133] The radiation-sensitive composition of the present invention is prepared by uniformly mixing the above-mentioned [A] photopolymerization initiator, [B] the polymerizable compound having an ethylenically unsaturated double bond, and the above-mentioned optionally added other components. This radiation-sensitive composition is preferably used in a solution state dissolved in an appropriate solvent. For example, [A] a photopolymerization initiator, [B] a polymerizable compound having an ethylenically unsaturated double bond, and optionally other components may be mixed in a solvent in a prescribed ratio to prepare a solution-state radiation-sensitive compound. sex composition.

[0134] As a solvent used in the preparation of the radiation-sensitive composition, each component capable of combining [A] a photopolymerization initiator, [B] a polymerizable compound having an ethylenically unsaturated double bond, and o...

Embodiment 1

[0163] [Example 1] (Synthesis of Compound (A-1))

[0164] Compound (A-1) (compound represented by the above formula (3)) was synthesized as the final product according to the following synthesis route.

[0165]

[0166] Step (I): Synthesis of intermediate (a)

[0167] Into a 300 ml eggplant-shaped flask, 8.5 g (61.5 mmol) of 5-norbornene-2-carboxylic acid was added, dissolved in 60 ml of ethanol, and replaced with nitrogen. Then, 0.5 g of 5% palladium-carbon was added, followed by catalytic reduction by hydrogen gas at 40° C. under normal pressure. After stirring for 16 hours, paper and Celite were placed in a suction filter, and suction filtration was performed. The filtrate was distilled off under reduced pressure to obtain 8.6 g of an intermediate (a).

[0168] Determination of the intermediate (a) 1 H-NMR, the results are as follows.

[0169] 1 H-NMR (solvent: CDCl 3 ) Chemical shift δ: 2.74ppm, 2.60ppm, (the peaks of the two isomers total 1H), 2.36ppm (1H), 2.06...

Embodiment 2

[0185] [Example 2] (Synthesis of compound (A-2))

[0186] In the step (I) of the synthetic route of the above-mentioned compound (A-1), except that the contact reduction is not carried out by hydrogen, it is carried out in the same manner as in Example 1 to obtain the compound (A-2) of Example 2 (the above formula (4 ) represented by the compound).

[0187] Determination of compound (A-2) 1 H-NMR, FT-IR, mass analysis, UV, the results are as follows.

[0188] 1 H-NMR (solvent: CDCl 3 ) Chemical shift δ: 8.81ppm, 8.75ppm (summation of the peaks of the two isomers 1H), 8.57ppm, 8.54ppm (summation of the peaks of the two isomers of 1H), 8.23ppm, 8.14ppm (the sum of the peaks of the two isomers isomer peak total 1H), 7.96ppm, 7.95ppm (two isomer peak total 1H), 7.44ppm (2H), 5.98ppm (2H), 4.40ppm (2H), 3.94ppm, 3.40ppm (two isomer peaks total 1H), 2.77ppm, 2.64ppm (both isomer peaks total 1H), 2.54ppm(3H), 2.37ppm(1H), 2.30ppm(3H), 2.06ppm(1H), 1.7~1.2ppm(8H)

[0189] FT-IR...

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PUM

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Abstract

The invention relates to a novel compound, a radioactive ray sensitivity composition, a solidified film and a forming method thereof. The invention aims to provide a compound, which has a high radiation susceptibility, good dissolvability in a radiation sensitivity composition and good transparency of solidified film when the compound is used as a photo polymerized initiator. A radiation sensitivity compound can obtain the solidified film with good transparency and surface hardness. The invention is a compound expressed in the following formula (1), where R4 is alicyclic alkyl with one part of or the whole hydrogen atoms being replaced by alkyl with 1-12 carbon atoms. The invention is the radiation sensitivity composition having the compound (A) as the photo polymerized initiator and the polymerized compound (B) having ethylene unsaturated double bonds. The radiation sensitivity composition preferably includes alkali soluble resin (C).

Description

technical field [0001] The present invention relates to a novel compound useful as a photopolymerization initiator, a radiation-sensitive composition comprising the same, a cured film formed from the composition, and a method for forming the same. Background technique [0002] Radiation-sensitive compositions have the advantages of being able to form cured products in large quantities and easily through the coating process, and are also easy to microfabricate the cured products. Therefore, in addition to liquid crystal displays, semiconductor device preparation materials, etc. It is widely used in permanent inks, photosensitive printing plates, etc. This 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 is coated on a glass substrate or the like to form a coating film, and then the c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C08F2/48G03F7/027G03F7/00
CPCC07D209/82C07D209/88G03F7/004G03F7/0045H01L21/027H01L21/0271
Inventor 岩沢晴生一户大吾
Owner JSR CORPORATIOON
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