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Phenolic hydroxyl resin and resist material

A technology of phenolic hydroxyl resin and novolac resin, which is applied in the field of resist materials and phenolic hydroxyl resins, can solve the problems of unusable, heat resistance, insufficient developability, inability to meet market requirements, etc., and achieve crack resistance Excellent performance and excellent alkali developability

Active Publication Date: 2021-09-17
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The most widely used phenolic hydroxyl group-containing resins for photoresist applications are cresol novolac-type resins, but they cannot meet the performance requirements of the recent market that is progressing in sophistication and diversification, and the heat resistance and developability are not sufficient. , In addition, when forming a thick film, cracks occur, so it cannot be used for thick film applications (see Patent Document 1)

Method used

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  • Phenolic hydroxyl resin and resist material
  • Phenolic hydroxyl resin and resist material
  • Phenolic hydroxyl resin and resist material

Examples

Experimental program
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Embodiment

[0150] Hereinafter, the present invention will be described in more detail with reference to specific examples. In addition, the number average molecular weight (Mn), weight average molecular weight (Mw), and polydispersity coefficient (Mw / Mn) of the synthetic|combined resin are the values ​​measured on the following GPC measurement conditions.

[0151] [Measurement conditions of GPC]

[0152] Measuring device: "HLC-8220GPC" manufactured by Tosoh Corporation

[0153] Column: Showa Denko "Shodex KF802" (8.0mmФ×300mm) + Showa Denko "Shodex KF802" (8.0mmФ×300mm)

[0154] + "ShodexKF803" made by Showa Denko Co., Ltd. (8.0mmФ×300mm) + "ShodexKF804" made by Showa Denko Co., Ltd. (8.0mmФ×300mm)

[0155] Column temperature: 40°C

[0156] Detector: RI (differential refractometer)

[0157] Data processing: "GPC-8020model II version 4.30" manufactured by Tosoh Corporation

[0158] Developing solvent: tetrahydrofuran

[0159] Flow rate: 1.0mL / min

[0160] Sample: A product obtained...

manufacture example 1 3

[0178] Production Example 1 Production of triarylmethane type compound (A-1)

[0179] 586.4 g of 2,5-xylenol and 244 g of 4-hydroxybenzaldehyde were put into a 3000 ml 4-necked flask equipped with a condenser, and dissolved in 1000 ml of 2-ethoxyethanol. After cooling in an ice bath and adding 30 ml of sulfuric acid, the mixture was heated to 100° C. with a mantle heater and reacted while stirring for 2 hours. After the reaction, water was added to the obtained solution to reprecipitate the crude product. The crude product was redissolved in acetone and reprecipitated with water, and the precipitate was filtered and vacuum-dried to obtain 421 g of a white crystal triarylmethane compound (A-1). pass 13 C-NMR confirmed the production of a compound represented by the following structural formula. The purity calculated from the GPC chart was a GPC purity of 98.2%. The GPC chart of triarylmethane type compound (A-1) is shown in figure 1 ,Will 13 The C-NMR diagram is shown in...

manufacture example 2

[0181] Production Example 2 Production of Novolak Resin Intermediate (M-1)

[0182] 174 g of a triarylmethane type compound (A-1) and 54 g of m-cresol were charged into a 3000 ml 4-necked flask equipped with a condenser, and then dissolved in 500 ml of 2-ethoxyethanol and 500 ml of acetic acid. After cooling in an ice bath and adding 50 ml of sulfuric acid, 33 g of 92% paraformaldehyde was added. The mixture was heated to 80° C. in an oil bath, and reacted while stirring for 10 hours. After the reaction, water was added to the obtained solution to reprecipitate the crude product. After redissolving the crude product in acetone and reprecipitating with water, the precipitate was filtered and vacuum-dried to obtain 213 g of a novolac resin intermediate (M-1) as a red powder. The number average molecular weight (Mn) of the novolac resin intermediate (M-1) was 1,937, the weight average molecular weight (Mw) was 12,822, and the polydispersity coefficient (Mw / Mn) was 6.62.

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Abstract

An object of the present invention is to provide a phenolic hydroxyl group-containing resin excellent not only in heat resistance and alkali developability, but also in crack resistance during thick film formation, a photosensitive composition containing the same, a curable composition, and a resist agent material, providing a phenolic hydroxyl-containing resin, characterized in that it has the following structural formula (1) or (2) [wherein R 2 , R 3 Each independently is any of an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, an alkoxy group, and a halogen atom. ] and the following structural formula (3) (where R 4 It is a hydrogen atom or an aliphatic hydrocarbon group having 1 to 7 carbon atoms. R 5 It is a hydrogen atom or an aliphatic hydrocarbon group having 8 to 24 carbon atoms. ) represented by the structural site (β) as a repeating unit, the R existing in the resin 2 , R 3 , R 5 At least one of them is an aliphatic hydrocarbon group having 8 to 24 carbon atoms.

Description

technical field [0001] The present invention relates to a phenolic hydroxyl group-containing resin that is excellent not only in heat resistance and alkali developability but also in crack resistance when forming a thick film, a photosensitive composition containing the same, a curable composition, and a resist material. Background technique [0002] In the field of photoresists, various resist pattern formation methods that are subdivided according to applications and functions have been developed one after another, and accordingly, the performance requirements for resin materials for resists have also become more advanced and diversified. . For example, a resin material for pattern formation is required to have high developability such that a fine pattern can be accurately formed in a highly integrated semiconductor with high productivity. In applications called underlayer films, anti-reflection films, BARC films, hard masks, etc., in addition to dry etching resistance an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G8/30
CPCC08G8/30C09B69/103C09B11/06C08G8/20C08L61/14G03F7/039
Inventor 今田知之佐藤勇介
Owner DIC CORP
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