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Acrylate film-forming resin containing adamantane structure, photoresist and preparation method

A technology of film-forming resin and acrylate, which is applied in the direction of photosensitive materials used in optomechanical equipment, etc., can solve the problems of poor adhesion between resin and substrate, poor dry etching resistance, high oxygen content, etc., and achieve excellent Anti-dry etching performance, excellent application effect, effect of improving solubility

Active Publication Date: 2022-03-04
四川华造宏材科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the linear structure of polymethacrylate polymer molecular chain and high oxygen content, it has some defects such as poor dry etching resistance and poor adhesion between resin and substrate in actual use.

Method used

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  • Acrylate film-forming resin containing adamantane structure, photoresist and preparation method
  • Acrylate film-forming resin containing adamantane structure, photoresist and preparation method
  • Acrylate film-forming resin containing adamantane structure, photoresist and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] The adamantane-containing acrylate film-forming resin polymer is prepared through the following steps:

[0059] Nitrogen flushed the reaction device for 20 minutes, and 0.6 g of 2-(methylthio) ethyl methacrylate (I-1), 6.1 g of 2-ethyl-2-adamantyl methacrylate (II- 1), 2.7g of 3-hydroxyl-1-adamantyl acrylate (III-2) and 0.3g of azobisisobutyronitrile were put into a 250mL round bottom flask and the device was sealed. Inject 100mL of tetrahydrofuran into the airtight container with a syringe, heat the oil bath to 65°C, and reflux for 24h to end the reaction. After concentrating the obtained mixed solution, drop it into 500mL of methanol:water=1:1 mixed solution to produce a white precipitate. After filtration, a white solid was obtained. Dissolve the solid with tetrahydrofuran, repeat precipitation three times to purify the polymer, and filter. The obtained white solid polymer was first placed in a fume hood to dry naturally for 24 hours, and then dried in a vacuum oven ...

Embodiment 2

[0067] The adamantane-containing acrylate film-forming resin polymer is prepared through the following steps:

[0068] The reaction apparatus was flushed with nitrogen for 20 minutes. 0.6g of 2-(methylthio) ethyl methacrylate (I-1), 2.6g of 3-hydroxyl-1-adamantyl acrylate (III-2) and 0.3g of azobisisobutyl Nitrile was put into a 250mL round-bottomed flask and the device was sealed. After sealing, nitrogen was replaced three times, and 8.0g of 2-methyl-2-adamantyl acrylate (II-2) and 100mL of tetrahydrofuran were injected into the airtight container through a syringe. , heated in an oil bath to 65°C, and refluxed for 24 hours to end the reaction. After concentrating the obtained mixed solution, it was dropped into 500 mL of methanol:water=1:1 mixed solution to produce a white precipitate. Dissolve the solid, repeat the precipitation three times to purify the polymer, filter, and place the obtained white solid polymer in a fume hood to dry naturally for 24 hours, then dry it in...

Embodiment 3

[0072] The adamantane-containing acrylate film-forming resin polymer is prepared through the following steps:

[0073] The reaction apparatus was flushed with nitrogen for 20 minutes. 0.6g of 2-(methylthio) ethyl methacrylate (I-1), 4.9g of 1-adamantyl acrylate (II-3), 2.6g of 3-hydroxyl-1-adamantane Acrylate (III-1) and 0.3g of azobisisobutyronitrile were put into a 250mL round-bottomed flask and the device was sealed. After sealing, the nitrogen was replaced three times, and 100mL of tetrahydrofuran was injected into the airtight container through a syringe, and the oil bath was heated to 65°C, reflux for 24 hours to end the reaction, concentrate the obtained mixed solution, drop it into 500mL methanol: water = 1:1 mixed solution, a white precipitate is produced, obtain a white solid after filtration, dissolve the solid with tetrahydrofuran, and repeatedly precipitate Purify the polymer three times, filter, and place the obtained white solid polymer in a fume hood to air dr...

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Abstract

The invention discloses acrylate film-forming resin containing an adamantane structure, photoresist and a preparation method, the film-forming resin has a structural formula shown as Im-co-IIn-co-IIIp, I is selected from a polar monomer containing a sulfur element, II is selected from a monomer containing an adamantane structure, III is selected from a hydrophilic monomer containing a hydroxyl group, co represents copolymerization, and the ratio of n to m to p is (10-20): (50-70): (20-30). The film-forming resin has excellent dry etching resistance, substrate adhesion and hydrophilicity, the solubility of photoresist in an alkaline developing solution after exposure is improved, the roughness of line edges is reduced, and the resolution and morphology of photoetching patterns can be effectively improved.

Description

technical field [0001] The invention relates to the technical field of photoresist, in particular to the technical field of DUV photoresist of acrylate film-forming resin. Background technique [0002] Smart devices are developing in the direction of more functions, and the core chips required are also progressing in a more refined direction. The lithography technology that restricts the chip manufacturing process has also undergone several generations of changes. According to the exposure light source, the lithography technology has gone through the G-line (436nm) and I-line (365nm) lithography of the initial high-pressure mercury lamp, to the KrF excimer laser (248nm), ArF excimer laser (193nm) and F2 excimer Laser (157nm) lithography, and now the development of EUV extreme ultraviolet (13.5nm) lithography. Among them, ArF excimer laser (193nm) immersion lithography technology is the most practical technology due to reasons such as economy. [0003] In the photolithograp...

Claims

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Application Information

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IPC IPC(8): C08F220/18C08F220/38C08F220/20G03F7/004
CPCC08F220/1812C08F220/1811G03F7/004C08F220/38C08F220/20
Inventor 盖景刚韦南君盖益诺孙义兴李一博
Owner 四川华造宏材科技有限公司
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