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A photoresist composition comprising polyparahydroxystyrene polymer and acrylate copolymer

A technology of hydroxystyrene and adamantanol methacrylate, which is applied in the field of photoresist, can solve problems such as thick film cracking, and achieve the effect of improving flexibility

Active Publication Date: 2020-12-08
江苏汉拓光学材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This application adopts the method of increasing the molecular weight of the adamantane polymer and increasing the flexibility of its main chain, and blending with the classic PHS resin (such as ESCAP resin) at the same time, effectively solving the cracking problem of the thick film

Method used

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  • A photoresist composition comprising polyparahydroxystyrene polymer and acrylate copolymer
  • A photoresist composition comprising polyparahydroxystyrene polymer and acrylate copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] This embodiment relates to the synthesis of poly(p-hydroxystyrene) polymers, and its synthetic route is as follows:

[0076] Under nitrogen protection, 97.3g of 4-acetoxystyrene (ASM), 20.8g of styrene (ST) and 25.6g of tert-butyl acrylate (TBA) were added successively to a 500ml four-necked flask, and then added 3.3 g of initiator azobisisobutyronitrile (AIBN), tetrahydrofuran as a solvent, and then react at 65-70° C. for 18 hours. After removing the protective group from the reaction product, a terpolymer of 4-hydroxystyrene-styrene-butyl acrylate is obtained, the weight average molecular weight Mw is 29.7K, and the molecular weight distribution Mw / Mn is 2.3.

Embodiment 2

[0078] This embodiment relates to the synthesis of tetrapolymers comprising acrylate comonomers, and its synthetic route is as follows: In this embodiment, 2-ethyl-2-adamantanol methacrylate (CAS accession number: 209982-56 -9), 2-carbonyl-tetrahydrofuran-3-hydroxy-methacrylate (α-methacryloyloxy-γ-butyrolactone, CAS accession number: 195000-66-9), cedaryl alcohol methacrylate (CAS accession number: 132603 -01-1), the molar ratio of 3-hydroxy-1-adamantanol methacrylate (CAS accession number: 115372-36-6) is 40:25:10:25.

[0079] In a 500ml four-necked flask, sequentially add monomer 46.1g of 2-ethyl-2-adamantanol methacrylate, 19.8g of 2-carbonyl-tetrahydrofuran-3-hydroxy-methacrylate, 13.5g of cedar Alcohol methacrylate, 27.4g of 3-hydroxy-1-adamantanol acrylate, 1.52g of initiator AIBN and 200g of solvent 1,4-dioxane, completely dissolved at room temperature under the action of magnetic stirring Finally, under the protection of nitrogen, set the temperature of the oil bath ...

Embodiment 3

[0081] This example relates to the preparation of a photoresist composition using the 4-hydroxystyrene-styrene-butyl acrylate terpolymer according to Example 1 and the acrylate copolymer according to Example 2.

[0082] In a clean 250 ml polypropylene plastic bottle, add 9g of 4-hydroxystyrene-styrene-butyl acrylate terpolymer according to embodiment 1, 21g of acrylate tetrapolymer synthesized according to embodiment 2, 0.6 g of triphenylsulfonium perfluorobutylsulfonate, 0.04 g of trioctylamine, and 69.32 g of mixed solvent PGMEA / PGME (8:2). Then, fix the polypropylene plastic bottle including the above-mentioned materials on a mechanical vibrator, and vibrate at room temperature for 10-24 hours to fully dissolve the above-mentioned materials. Finally, it was filtered through a filter with a pore size of 0.2 micron to obtain the photoresist composition according to Example 3.

[0083] Photolithography experiment method and results: The photoresist composition prepared above ...

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Abstract

The present application relates to a photoresist composition comprising (a) acrylate copolymer; (b) poly(p-hydroxystyrene) polymer; (c) photoacid generator; (d) acid a quencher; and (e) a solvent. The beneficial effect of the present application is that by increasing the molecular weight of the acrylate copolymer and improving the flexibility of the molecular chain of the acrylate copolymer, and blending the acrylate copolymer with traditional poly(p-hydroxystyrene) polymers, the solution based on acrylate The cracking problem of the photoresist when the thickness is greater than or equal to 6 microns, so that the photoresist composition of the present application can meet the requirements of photolithography and etching at 248 nm with a thickness greater than or equal to 6 microns.

Description

technical field [0001] This application relates to the field of photoresist technology. In particular, the present application relates to a photoresist composition comprising a poly(p-hydroxystyrene) polymer and an acrylate copolymer. Background technique [0002] In the preparation of 3D NAND memory, a deep ultraviolet Deep UV (DUV248nm) photoresist with a thickness greater than or equal to 6 microns is required for multiple etching of steps in NAND. Traditional 248nm KrF photoresists are based on poly(p-hydroxystyrene) polymers, which have high UV absorption, and cannot perform effective photolithography when the thickness is greater than 5um, especially greater than or equal to 6 microns. [0003] In addition, acrylate-based photoresists are commonly used as ArF photoresists at 193nm. As far as the inventors are aware, there is no document reporting or disclosing a photoresist with a thickness greater than or equal to 6 micrometers and capable of photolithography at 248...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G03F7/039C08F212/14C08F212/08C08F220/18C08F220/20C08F220/30
CPCG03F7/039C08F212/14C08F220/18C08F220/20C08F220/1812C08F220/302C08F220/1818C08F212/08C08F220/1804
Inventor 毛国平霍建辉刘平陈英博韩政孙友松冉瑞成
Owner 江苏汉拓光学材料有限公司
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