Novel compound, photopolymerization initiator containing said compound, and photosensitive resin composition containing said photopolymerization initiator

A photosensitive resin and compound technology, applied in the field of photosensitive resin compositions, can solve the problems of low quantum efficiency, unsolved nature of polyimide precursor polymerization, etc., and achieve the effect of reducing the reaction start temperature

Inactive Publication Date: 2020-07-24
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the absorption wavelength of the photobase generator used in the examples in the literature is less than 350 nm overlapping with the absorption wavelength of the polyimide precursor, so the quantum efficiency of cracking is low, and the thermosetting reaction after light irradiation needs to be The high temperature above 200°C does not solve the essential problem of the polymerization of polyimide precursors

Method used

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  • Novel compound, photopolymerization initiator containing said compound, and photosensitive resin composition containing said photopolymerization initiator
  • Novel compound, photopolymerization initiator containing said compound, and photosensitive resin composition containing said photopolymerization initiator
  • Novel compound, photopolymerization initiator containing said compound, and photosensitive resin composition containing said photopolymerization initiator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0213] Synthesis of the compound shown in the formula (1) of the present invention of embodiment 1

[0214] (step 1) synthesis of the intermediate compound shown in formula (31)

[0215] After adding and dissolving 10 parts of water and 53 parts of ethanol to 1.9 parts of potassium cyanide, ultrasonic treatment was performed in a nitrogen atmosphere to degas the reaction liquid. 10 parts of 4-(methylthio)benzaldehyde represented by following formula (30) was dripped at this solution, and it heated to 80 degreeC and started reaction. After stirring for 30 minutes, the reaction liquid was cooled to 3° C., and the precipitated crystals were recovered by suction filtration. The recovered crystals were purified by recrystallization using a large amount of ethanol to obtain 7.6 parts of an intermediate compound represented by the following formula (31).

[0216]

[0217] (step 2) synthesis of the intermediate compound shown in formula (32)

[0218] In a flask equipped with a s...

Embodiment 2

[0223] Synthesis of the compound shown in the formula (1) of the present invention in embodiment 2

[0224] (Step 4) Synthesis of the compound (photopolymerization initiator C-2) of the present invention represented by the following formula (C-2)

[0225] Except for using 2-acryloyloxyethyl isocyanate (KarenzAOI manufactured by Hedenko Co., Ltd.) to replace 2-methacryloyloxyethyl isocyanate, the rest are obtained in the same manner as step 3 to obtain the following formula (C-2) The represented compound of the present invention (initiator C-2) is 6.4 parts.

[0226]

Embodiment 3 and 4、 comparative example 2 to 5

[0238] (Examples 3 and 4, Comparative Examples 2 to 5 preparation of photosensitive resin composition)

[0239] Each component was mixed according to the compounding quantity shown in Table 2, and the photosensitive resin composition was obtained.

[0240] (Curing test of photosensitive resin composition)

[0241] After coating the photosensitive resin compositions of Examples 3 and 4 and Comparative Examples 2 to 5 on the Si substrate by spin coating, they were dried by prebaking (PREBAKE) at 100°C for 2 minutes on a hot plate to obtain a film thickness 10 μm resin composition layer. Then, exposure was performed using a high-pressure mercury lamp contact aligner (Conduct Aligner), and irradiated at 800mJ / cm 2 (365nm) UV light. Then, developing treatment was carried out by dipping method using PGMEA (23°C, 30 seconds), and the remaining film rate was evaluated by measuring the film thickness after development with a stylus type film thickness measuring device (film thicknes...

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Abstract

The purpose of the present invention is to provide: a novel compound which has excellent solvent solubility and compatibility with a resin, and which can generate bases and radicals with high efficiency by being irradiated with active energy rays; a photopolymerization initiator which contains said novel compound; and a photosensitive resin composition which contains said photopolymerization initiator and from which a cured product can be obtained that has high sensitivity and no metal corrosion. This novel compound is represented by formula (1). In formula (1), R1, R2, R3, R5 and R6 representa hydroxyl group or an alkoxy group. The R4's independently represent an organic group containing a thioether bond. R7 and R9 independently represent a hydrogen atom or an alkyl group with 1 to 4 carbons. R8 represents an alkylene group or an arylene group. X represents an oxygen atom or a sulfur atom.

Description

technical field [0001] The present invention relates to a novel compound, a photopolymerization initiator containing the compound and generating bases and radicals by irradiation with active energy rays, and a photosensitive resin composition containing the photopolymerization initiator. Background technique [0002] A photoacid generator that generates a strong acid by irradiation with active energy rays such as light, infrared rays, electron rays, or X-rays, or a chemically amplified resist in which the photoacid generator is blended into a resin component has been conventionally known, and used for various purposes. [0003] This kind of chemically amplified resist acts on the resin component by the strong acid generated by the irradiation of active energy rays as a catalyst, and changes the solubility of the resin to the developer to form a pattern. Various resist materials have been developed for the purpose of increasing sensitivity and resolution, but the combination...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/22C08F2/50C08F20/36
CPCC08F2/50C07C323/22C07C2601/14C08F20/38C07C323/32C08F20/36C07C323/62C08F20/60C08G59/063
Inventor 寺田究桑原博一
Owner NIPPON KAYAKU CO LTD
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