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Cyclodextrin inclusion compound molecular glass photoresist

A cyclodextrin inclusion compound and molecular glass technology, applied in the field of photoresist, can solve the problem of resin solubility, irregular sawtooth, stuck neck, etc., to solve the stuck neck problem, improve the dry corrosion resistance, structure regular effect

Pending Publication Date: 2022-07-22
南通林格橡塑制品有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, in order to meet the requirements of anti-etching, the resin structure usually contains macromolecule anti-etching groups with ester ring structure, such as adamantane, norbornane and other structures, but when the rigid structural group is introduced into the polymer, it will not be used in the developing process. When the film-forming resin has a large relative molecular weight and a wide molecular weight distribution, it is easy to cause high-precision lines to collapse, and the edges of the lines are rough. In addition, most of the raw materials of KrF, ArF, and EUV photoresists are controlled by chemical giants in Japan, Germany, and the United States, so the synthesis of KrF, ArF, and EUV photoresists by using imported monomers cannot be obtained from Solve the problem of stuck neck at the source

Method used

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  • Cyclodextrin inclusion compound molecular glass photoresist
  • Cyclodextrin inclusion compound molecular glass photoresist
  • Cyclodextrin inclusion compound molecular glass photoresist

Examples

Experimental program
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Effect test

Embodiment 1

[0041] In a nitrogen-filled state, each glucose unit contains 1.6-2 methyl β-cyclodextrin (methyl β-cyclodextrin) 14.3 g (about 11 mmol), and 1-adamantanol 2 g (about 13 mmol) Mixed, heated to 250°C in a sealed state, shaken for 30 min and cooled to room temperature to obtain an inclusion resin containing 1-adamantanol by cyclodextrin; take 13.1 g (about 9 mmol) of the inclusion resin and 4-dimethylamino Pyridine 6.6g (about 54mmol) was dissolved in 300ml of anhydrous tetrahydrofuran, and then 18g (about 82mmol) of di-tert-butyl carbonic anhydride was added and stirred at room temperature for 20 hours. After 20 hours of stirring, an appropriate amount of deionized water was injected, the sediment was collected, and rinsed with sufficient deionized water. It was then dissolved in ethyl acetate, washed with saturated brine; dried over anhydrous magnesium sulfate, the solution was filtered and concentrated, and vacuum-dried at 50° C. for 12 hours to obtain molecular glass film-for...

Embodiment 2

[0044] Dissolve 13 g (about 10 mmol) of β-cyclodextrin (methyl β-cyclodextrin) containing 1.6 to 2 methyl groups in each glucose unit in 200 ml of deionized water, then add a saturated solution of o-carborane in tetrahydrofuran, and heat up. To 60 ℃ of stirring for 20 hours, the water is distilled off at a high temperature in a vacuum, and the obtained solid will be removed with chloroform to remove excess o-carborane to obtain a cyclodextrin inclusion o-carborane inclusion resin; get this inclusion resin 13g (about 9mmol) and 6.6g (about 54mmol) of 4-dimethylaminopyridine were dissolved in 300ml of anhydrous tetrahydrofuran, and then 18g (about 82mmol) of di-tert-butyl carbonate was added at room temperature and stirred for 20 hours. , rinsed with sufficient deionized water, dissolved in ethyl acetate, and washed with saturated brine; then dried over anhydrous magnesium sulfate, the solution was filtered and concentrated, and vacuum-dried at 50 °C for 12 hours to obtain a mole...

Embodiment 3

[0047] Dissolve 13 g (about 10 mmol) of β-cyclodextrin (methyl β-cyclodextrin) containing 1.6 to 2 methyl groups in each glucose unit into 200 ml of deionized water to form a solution, and then add 1,1 ferrocene formic acid 5.2 g (about 19 mmol) was dissolved in 100 ml of tetrahydrofuran, mixed into methyl β-cyclodextrin aqueous solution, heated to 50° C., stirred under 30KHz ultrasonic vibration for 20 hours, spray-dried, and the obtained solid was removed with chloroform to remove excess 1,1-dioxane ferrocene carboxylic acid to obtain an inclusion resin containing 1,1 ferrocene carboxylic acid with cyclodextrin; take 14.2 g (about 9 mmol) of the inclusion resin and 6.6 g (about 54 mmol) of 4-dimethylaminopyridine and dissolve it in 300 ml add 18 g (about 82 mmol) of di-tert-butyl carbonic anhydride, stir at room temperature for 20 hours, inject an appropriate amount of deionized water, collect the sediment, rinse with sufficient deionized water, dissolve in ethyl acetate, use...

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Abstract

The invention discloses a cyclodextrin inclusion compound molecular glass photoresist, and belongs to the technical field of semiconductor microelectronic chemistry. The photoresist contains cyclodextrin inclusion compound film-forming resin, a photoacid generator, an auxiliary agent and a solvent. The cyclodextrin inclusion compound is an inclusion compound which takes a cyclodextrin derivative as a main body resin and an anti-corrosion molecule with an ester ring and an aromatic ring as a guest material. The cyclodextrin derivative has corrosion resistance, and keeps the characteristics of single molecular weight, good film-forming property and high glass transition temperature (Tg) of the cyclodextrin derivative; the film-forming resin has very high transparency in 248nm and 193nm of a deep ultraviolet region and 13.5 nm of extreme ultraviolet, and KrF, ArF and EUV photoresists prepared by matching the film-forming resin with a photoacid generator (PAG), an auxiliary agent and a solvent can meet the requirements of a photoetching process of a large-scale integrated circuit. In addition, the core raw materials adopted by the invention are all from the country, so that the clamping problem of the DUV semiconductor photoresist and the raw materials thereof can be thoroughly solved from the source.

Description

technical field [0001] The invention relates to a photoresist used in ultra-large-scale integrated circuit chips, in particular to a photoresist using a single ultraviolet light below 248 nm as an exposure light source, and belongs to the technical field of semiconductor microelectronic chemistry. Background technique [0002] Photoresist, also known as photoresist, refers to an etching-resistant film material whose solubility changes under irradiation or radiation of ultraviolet light, electron beam, ion beam, X-ray, etc. In recent years, with the trend of miniaturization, light weight and portability of electronic and electrical products, the integration of VLSI chips has become higher and higher, and the wavelength of the lithography exposure light source of semiconductor chips has been continuously shortened, from 365nm (i-line) Developed to 248nm (KrF), 193nm (ArF) and 13nm (EUV). In order to improve the sensitivity of the photoresist, the current mainstream KrF, ArF, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/004
CPCG03F7/004
Inventor 曾伟
Owner 南通林格橡塑制品有限公司
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