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Phenolic hydroxyl group-containing resin, photosensitive composition, resist film, curable composition, and cured product

A technology of phenolic hydroxyl resin and phenolic resin, which is applied in the fields of optics, optomechanical equipment, instruments, etc., and can solve problems that are difficult to balance heat resistance and alkali dissolution speed

Pending Publication Date: 2021-09-03
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is a problem that it is difficult to balance heat resistance and alkali dissolution rate, which are important characteristics for thick film resists.

Method used

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  • Phenolic hydroxyl group-containing resin, photosensitive composition, resist film, curable composition, and cured product
  • Phenolic hydroxyl group-containing resin, photosensitive composition, resist film, curable composition, and cured product
  • Phenolic hydroxyl group-containing resin, photosensitive composition, resist film, curable composition, and cured product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0255] Hereinafter, the present invention will be specifically described by examples and comparative examples.

[0256] It should be noted that the number average molecular weight (Mn) of the resin prepared in the examples, the weight average molecular weight (MW), and multi-dispersion degrees (MW / Mn) are measured by the following GPC measurement conditions.

[0257] [GPC measurement conditions]

[0258] Measurement device: "HLC-8220GPC" by Dong Cao Co., Ltd.

[0259] Column: Shoex KF802 "(8.0mmф × 300mm) + Shoe Electrical Co., Ltd. (8.0mmф × 300mm) + Shoe Electric Co., Ltd. (8.0mmф ×) (8.0mmф ×) (8.0mmф × 300mm) + Shoe Electronic Co., Ltd. (SHODEX KF802" (8.0mф × 300mm) 300mm) + "Shodex KF804" (8.0mmф × 300mm) made by Showa Electric Co., Ltd.

[0260] Column temperature: 40 ° C

[0261] Detector: ri (differential refractometer)

[0262] Data Processing: "GPC-8020 Model II version 4.30" made by Dong Cao Co., Ltd.

[0263] Expand solvent: tetrahydrofuran

[0264] Flow rate: 1.0ml...

Synthetic example 1

[0283] Synthesis Example 1 Synthesis of phenolic trigonid compound containing carboxylic acid

[0284] To the 2000 ml of the four-mouth flask provided with a cooling tube, 2,5-dimethylphenol was investigated, 4-formylbenzoic acid 150 g (1 mol) was dissolved in 500 ml of acetic acid. After 5 ml of sulfuric acid was added to the ice bath, the heater was heated with a cover heater for 2 hours at 100 ° C, and stirring was carried out. After the reaction, the resulting solution was redditized with water to give a crude product. The crude product was then dissolved in acetone, and then the resulting product was filtered after further use water, and the resulting product was taken as vacuum, and the precursor compound (A-1) 283 g of a pale pink crystal was obtained.

[0285] For the resulting precursor compound (A-1), 13 The C-NMR spectroscopy determines that it is confirmed that it is a compound represented by the following structural formula. In addition, the GPC purity calculated from...

manufacture example 1

[0287] Production Example 1 Synthesis of Phenolic Varcies Phenolic Resins containing carboxylic acids

[0288] The precursor compound (A-1) 188 g, 92% polyformaldehyde (B-1) 16 g was introduced into the 1000 ml of the four-mouth flask provided, and was dissolved in 500 ml of acetic acid. After 10 ml of sulfuric acid was added over the ice bath, he was heated to 80 ° C with an oil bath, and the mixture was stirred for 4 hours. After the reaction is completed, water is added to the resulting solution to re-precipitate the crude product. The crude product was then dissolved in acetone, and then the precipitate was filtered, and the phenolic varnoid phenol resin resin (C-1) of the orange powder was filtered.

[0289] The number average molecular weight (Mn) of the obtained phenolic varomidic phenol resin (C-1) was 3946, the weight average molecular weight (MW) was 8504, and the multispice degrees (Mw / Mn) were 2.16.

[0290] GPC spectrum of the obtained phenolic varnish phenol resin ...

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Abstract

The present invention addresses the problem of providing a phenolic hydroxyl group-containing resin having superior heat resistance and, when being used as a resist material, exhibits excellent alkali developing properties. Provided is a phenolic hydroxyl group-containing resin which is a reaction product of: an alcohol compound (X); and a novolac type phenol resin (C), of which essential reaction materials are an aliphatic aldehyde (B) and an aromatic compound (A) represented by formula (1). In formula (1): R1 and R2 each represent an aliphatic hydrocarbon group having 1-9 carbon atoms, an alkoxy group, an aryl group, an aralkyl group, or a halogen atom; m, n, and p each represent an integer of 0-4; R3 represents a hydrogen atom, an aliphatic hydrocarbon group having 1-9 carbon atoms, or a structural moiety having, on a hydrocarbon group, at least one substituent selected from alkoxy groups, halogen groups, and a hydroxyl group; and R4 represents a hydroxyl group, an aliphatic hydrocarbon group having 1-9 carbon atoms, an alkoxy group, or a halogen atom.

Description

Technical field [0001] The present invention relates to a phenolic hydroxyl group resin, a photosensitive composition, a resist film, the curable composition and a cured product. Background technique [0002] In the field of photoresists, have developed a method for forming a purpose, a variety of functions subdivided resist pattern. Accordingly, the performance requirements for the resist resin material and also sophistication diversification. For example, as a resist for producing IC, LSI and other semiconductor manufacturing apparatus such as an LCD display, for producing printing original plate or the like used in known to use an alkali-soluble resin and 1,2-naphthoquinone diazide compound other positive-type photosensitive agent obtained photoresist. [0003] Examples of the alkali-soluble resin, proposed a positive type photoresist composition using a cresol novolac epoxy resin obtained (e.g., refer to Patent Documents 1 and 2). [0004] Cresol novolac epoxy resin obtained ...

Claims

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Application Information

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IPC IPC(8): C08G8/04C08G8/28G03F7/038
CPCC08G8/04G03F7/038C08G8/28C08G8/18G03F7/0392
Inventor 今田知之长田裕仁
Owner DIC CORP
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