Preparation method of resin for photoresist

A technology of photoresist and resin, which is applied in the field of polymer resin preparation, can solve problems such as the introduction of impurities, limit the process of industrialization, and high toxicity, and achieve the effects of precise molecular weight control, simple implementation, and excellent application performance

Inactive Publication Date: 2019-06-28
NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The solvents commonly used in traditional ATRP polymerization reactions, such as toluene, etc., have limited their industrialization process due to their high toxicity.
In recent years, by using other solvents for ATRP polymerization, the polymerization can be effectively promoted, but the controllability of the reaction is reduced
[0006] At present, the preparation of photoresist resin is mainly based on free radical polymerization, and changing the molecular weight by increasing the initiator will cause the introduction of impurities, which will adversely affect the quality of photoresist

Method used

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  • Preparation method of resin for photoresist
  • Preparation method of resin for photoresist

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The preparation method of photoresist resin comprises the following steps:

[0041] (1) Take 35.62ml of tetrahydrofuran with water content of 200ppm into the reaction bottle, and heat it to 50-80°C for later use;

[0042] (2) Dissolve 9.87g of butyrolactone methacrylate, 7.05g of 3-hydroxy-2-adamantyl methacrylate, 15g of 1-ethylcyclohexyl methacrylate and 3.5g of azobisisobutyronitrile in In the THF of 74.83ml, obtain the THF solution of raw material;

[0043] (3) adding the tetrahydrofuran solution of the raw material obtained in step (2) dropwise into the preheated tetrahydrofuran containing moisture in step (1), and reacting at reflux at a constant temperature of 70 to 80°C for 15 hours;

[0044] (4) After the reaction is completed, cool to room temperature, precipitate the resin with n-hexane, filter and dry to obtain the resin for photoresist (1).

[0045] (5) The photoresist resin (1) can be obtained by GPC test, Mw=8900, PDI=1.62.

Embodiment 2

[0047] The preparation method of photoresist resin comprises the following steps:

[0048] (1) Take 35.62ml of tetrahydrofuran with water content of 400ppm into the reaction bottle, and heat it to 50-80°C for later use;

[0049] (2) Dissolve 9.87g of butyrolactone methacrylate, 7.05g of 3-hydroxy-2-adamantyl methacrylate, 15g of 1-ethylcyclohexyl methacrylate and 3.5g of azobisisobutyronitrile in In the THF of 74.83ml, obtain the THF solution of raw material;

[0050] (3) adding the tetrahydrofuran solution of the raw material obtained in step (2) dropwise into the preheated tetrahydrofuran containing moisture in step (1), and reacting under constant temperature reflux at 70-80°C for 15 hours;

[0051] (4) After the reaction is completed, cool to room temperature, precipitate the resin with n-hexane, filter and dry to obtain the resin for photoresist (2).

[0052] (5) The photoresist resin (2) can be obtained by GPC test, Mw=9200, PDI=1.57.

Embodiment 3

[0054] The preparation method of photoresist resin comprises the following steps:

[0055] (1) Take 35.62ml of tetrahydrofuran with water content of 500ppm into the reaction bottle, and heat it to 50-80°C for later use;

[0056] (2) Dissolve 9.87g of butyrolactone methacrylate, 7.05g of 3-hydroxy-2-adamantyl methacrylate, 15g of 1-ethylcyclohexyl methacrylate and 3.5g of azobisisobutyronitrile in In the THF of 74.83ml, obtain the THF solution of raw material;

[0057] (3) adding the tetrahydrofuran solution of the raw material obtained in the step (2) dropwise into the preheated tetrahydrofuran containing moisture in the step (1), and reacting at a constant temperature of 70 to 80° C. for 15 hours under reflux;

[0058] (4) After the reaction is completed, cool to room temperature, precipitate the resin with n-hexane, filter and dry to obtain the resin for photoresist (3).

[0059] (5) The photoresist resin (3) can be obtained by GPC test, Mw=9300, PDI=1.47.

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Abstract

The invention discloses a preparation method of resin for photoresist. The preparation method is characterized in that the resin is prepared by the steps of dissolving one or more monomers with acid active groups and one or more monomers with polar groups into a solvent containing a certain amount of moisture, and carrying out ATRP reaction in the presence of an initiator. The preparation method comprises the following steps: (1) heating the solvent containing a certain amount of moisture to 50-80 DEG C, so as to obtain a preheated organic solvent containing moisture; (2) dissolving the monomers and an initiator into the organic solvent containing the same moisture with the organic solvent in the step (1), so as to obtain a raw material solution; (3) dropwise adding the raw material solution into the preheated organic solvent containing moisture, and carrying out content-temperature reflux reaction at 50-80 DEG C for 10-30 hours; and (4) cooling to the room temperature, precipitating resin with a non-polar solvent, filtering, and drying, so as to obtain the resin for the photoresist, wherein the moisture content in the solvent is 1ppm-1500ppm. According to the preparation method, the molecular weight of the polymer resin is regulated through the regulation of the water content, so that other impurities are not introduced, and the control of the molecular weight is relatively precise.

Description

technical field [0001] The invention relates to the preparation of a polymer resin, in particular to a preparation method of the resin used for photoresists. Background technique [0002] Photoresist is a key material in the manufacture of advanced integrated circuits today. The film-forming material of the photoresist is various photoresist resins. KrF photoresist mainly uses poly(p-hydroxystyrene) resin as the film-forming material. Since the main structure of the resin is benzene ring, it has absorption at 193nm. All, ArF photoresist film-forming resin materials are mainly transparent (meth)acrylic resins at 193nm. At the same time, with the miniaturization of components, the photolithographic patterns that need to be produced are getting smaller and smaller. Making small-scale patterns requires photoresists with lower molecular weight and more uniform molecular weight distribution to maintain excellent performance. Therefore, it is extremely important to master the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/18C08F220/20C08F2/06C08F2/38G03F7/004
Inventor 樊丹祝晓岚马潇顾大公毛智彪陈鹏
Owner NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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