Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Phenolic hydroxyl group-containing resin and resist material

A technology of phenolic hydroxyl resin and hydrocarbon group, applied in the field of phenolic hydroxyl resin, can solve the problems of low coatability, low fluidity, insufficient surface smoothness, etc., and achieve high heat resistance and dry etching resistance, fluidity excellent effect

Active Publication Date: 2019-05-21
DIC CORP
View PDF9 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Naphthol novolac-type resins are characterized by excellent dry etching resistance due to the rigid naphthalene skeleton, but due to their low fluidity, the applicability to the substrate surface with unevenness is low, and the surface smoothness of the obtained film is also poor. insufficient

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Phenolic hydroxyl group-containing resin and resist material
  • Phenolic hydroxyl group-containing resin and resist material
  • Phenolic hydroxyl group-containing resin and resist material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] The manufacture of embodiment 1 phenolic hydroxyl resin (1)

[0122]152 parts by mass of the bis-naphthol compound (a1), 31 parts by mass of cyanuric chloride, and 500 parts by mass of methyl ethyl ketone obtained before were charged into a 1000-ml 4-necked flask equipped with a condenser, and stirred and dissolved. After heating to about 50°C to 70°C, 52 parts by mass of triethylamine was added dropwise over 60 minutes. After completion of the dropwise addition, stirring was continued at 70° C. for 5 hours. Next, 200 parts by mass of water was added to dissolve triethylamine hydrochloride, and liquid separation was performed, and the water layer was discarded. Furthermore, after washing twice with the same amount of water, the methyl ethyl ketone was recovered by distillation, and the mixed solvent of methanol / water=10 / 1 (mass ratio) was used for reprecipitation twice, and the precipitate was recovered and dried under reduced pressure to obtain 113 parts by mass of p...

Embodiment 2

[0123] The manufacture of embodiment 2 phenolic hydroxyl resin (2)

[0124] In Example 1, except having changed the addition amount of the bis-naphthol compound (a1) from 152 mass parts to 114 mass parts, it carried out similarly to Example 1, and obtained 92 mass parts of phenolic hydroxyl-containing resins (2). The obtained phenolic hydroxyl group-containing resin (2) has a number average molecular weight (Mn) of 1,013, a weight average molecular weight (Mw) of 1,252, a polydispersity coefficient (Mw / Mn) of 1.24, and a number average molecular weight (Mn) of 500 or less The content is 2.8%. In addition, the content of the polynuclear compound (A) in the phenolic hydroxyl group-containing resin (2)) was 37.9%, and the total content of the polynuclear compound (A) and the compound (B) was 61.5%.

Embodiment 3、4 and comparative example 1、2

[0130] The phenolic hydroxyl group-containing resin obtained in Examples 1 and 2 and Comparative Production Examples 1 and 2 were evaluated in the following manner. The results are shown in Table 1.

[0131] Manufacture of thermosetting compositions

[0132] 1.6 parts by mass of resin containing phenolic hydroxyl group, 0.4 parts by mass of curing agent ("1,3,4,6-tetrakis(methoxymethyl) glycoluril" manufactured by Tokyo Chemical Industry Co., Ltd.), 0.1 part by mass of p-toluenesulfonic acid It was dissolved in 100 parts by mass of propylene glycol monomethyl ether acetate, and this was filtered through a 0.2 μm membrane filter to obtain a thermosetting composition.

[0133] Evaluation of sublimation resistance

[0134] The previously obtained thermosetting composition was coated on a 5-inch silicon wafer with a spinner, and dried on a hot plate at 110° C. for 180 seconds in an environment having an oxygen concentration of 20% by volume. Next, heat curing was performed at 2...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
polydispersity indexaaaaaaaaaa
thicknessaaaaaaaaaa
polydispersity indexaaaaaaaaaa
Login to View More

Abstract

The purpose of the invention is to provide: a phenolic hydroxyl group-containing resin that has excellent flowability and provides excellent heat resistance and dry etching resistance in a cured product; and a curable composition and a resist material containing the resin. Provided is a phenolic hydroxyl group-containing resin which is a reaction product of a bisnaphthol compound (a1) representedby structural formula (1) (wherein X represents a C1-14 hydrocarbon group, R1s each independently represent an aliphatic hydrocarbon group, an alkoxy group, a halogen atom, an aryl group or an aralkylgroup, m is 0, 1 or 2, and n is an integer of 0 or 1 to 4) and a cyanuric halide (a2), the phenolic hydroxyl group-containing resin having a polydispersity (Mw / Mn) within a range from 1.01 to 1.30.

Description

technical field [0001] The present invention relates to a phenolic hydroxyl-containing resin having excellent fluidity and high heat resistance and dry etching resistance of a cured product, a curable composition containing the resin, and a resist material. Background technique [0002] In the field of photoresist, various resist pattern forming methods classified according to application and function have been successively developed, and accordingly, the required performance of resin materials for resists has also been advanced and diversified. For example, a resin material for pattern formation is required to have high developability such that a fine pattern can be formed on a highly integrated semiconductor accurately and with high productivity. In applications such as underlayer films, antireflection films, BARC films, hard masks, etc., dry etching resistance, low reflectivity, and high fluidity that can cope with uneven substrate surfaces are required. In addition, in ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C08G8/36C07D251/34C08G65/34G03F7/032
CPCC07D251/34C08G8/36C08G65/34G03F7/032G03F7/0045
Inventor 今田知之长江教夫
Owner DIC CORP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com