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Modified phenolic resin for photoresist and preparation method thereof

A technology of phenolic resin and photoresist, which is applied in the field of modified phenolic resin for photoresist and its preparation, can solve the problem of high resolution of photoresist, good heat resistance, and difficulty of simultaneous resolution and heat resistance of phenolic resin Problems such as improvement are achieved to achieve the effect of high resolution, narrow molecular weight distribution, improved heat resistance and resolution

Active Publication Date: 2021-10-01
浙江自立高分子化工材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to improve the defect that the resolution and heat resistance of the existing phenolic resin for photoresist are difficult to be improved at the same time, the invention provides an improved modified phenolic resin for photoresist and its preparation method. A certain proportion of 4,4'-dihydroxydiphenyl ether and 2-hydroxyl 1-hydroxymethylnaphthalene (CAS No 5386-25-4) and a small amount of phenolic polyhydroxy Compared with the process control, a phenolic resin with a narrow molecular weight distribution has been obtained, which has good heat resistance and high resolution of the photoresist, which can be used in the photoresist for G-line and I-line semiconductors

Method used

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  • Modified phenolic resin for photoresist and preparation method thereof
  • Modified phenolic resin for photoresist and preparation method thereof
  • Modified phenolic resin for photoresist and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (S1) Add 70 parts of p-cresol, 110 parts of 37% formaldehyde aqueous solution and 1 g of sodium hydroxide to the reaction kettle, raise the temperature to 50°C for 2 hours, add dilute hydrochloric acid for neutralization, and wash the product until it is neutral for later use to obtain a prepolymer ;

[0038] (S2) The prepolymer obtained in step (S1), 50 parts of m-cresol, 8 parts of 3,5-xylenol, 15 parts of 2-hydroxyl 1-hydroxymethylnaphthalene, 160 parts of 37% formaldehyde, 0.9 part For oxalic acid, fully dissolve with 500 parts of ethylene glycol monomethyl ether, stir evenly, and continue to heat up to 90°C for 2 hours;

[0039] (S3) Continue to heat up to 95°C, slowly add 40 parts of ethylene glycol monomethyl ether dissolved with 6 parts of 4,4'-dihydroxydiphenyl ether and 0.5 part of oxalic acid, and react for 4 hours;

[0040] (S4) After cooling down to 75°C, add 0.5 parts of TrisP-PA and continue the reaction for 1 hour. The final product is washed with deion...

Embodiment 2-10

[0041] Embodiment 2-10, comparative example 1-3

[0042] Other conditions are the same as in Example 1, except that the amount of materials added is different. The mass parts of the materials in the example are listed in Table 1 below, and finally a modified phenolic resin is obtained.

[0043] Table 1

[0044]

[0045]

Embodiment 12

[0047] The formula is the same as that of Example 3, except that the four-step segmented reaction sequence is not used, but all the materials are added in one pot method, and then reacted at 90° C. for 6 hours.

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Abstract

The invention relates to a modified phenolic resin for photoresist. The modified phenolic resin is characterized by being prepared from the following raw materials through polycondensation: m-cresol, p-cresol, xylenol, 4,4'-dihydroxy diphenyl ether, 2-hydroxy-1-hydroxymethyl naphthalene, a phenolic polyhydroxy compound and formaldehyde. According to the preparation method, 4,4'-dihydroxy diphenyl ether and 2-hydroxy-1-hydroxymethyl naphthalene are used for replacing part of cresol, a small amount of phenolic polyhydroxy compound is added in the later stage of reaction, and according to a specific preparation process, the heat resistance and resolution ratio of the phenolic resin can be improved at the same time. The phenolic resin with excellent comprehensive performance is finally obtained, tests show that the softening temperature of the phenolic resin is about 140 DEG C, the weight-average molecular weight of the phenolic resin is 8000-15000, the Mw / Mn of the phenolic resin is 2-3, the molecular weight distribution of the phenolic resin is narrow, and as film-forming resin of I-line photoresist, the resolution of the photoresist can reach 0.45 [mu]m or above.

Description

technical field [0001] The invention relates to the field of polymer synthesis, in particular to a modified phenolic resin for photoresists and a preparation method thereof. Background technique [0002] Photoresist is the core material of the photolithography process. It is used as a film-forming material in the processing of fine graphics such as display panels, integrated circuits, and semiconductor discrete devices. It is mainly composed of photosensitive resins, photosensitizers, solvents, and additives. In order to improve the lithography resolution of photoresist, the exposure wavelength of photolithography process is shortened from 436nm of ultraviolet G line, 365nm of I line, to 248nm of KrF excimer laser, and then to 193nm of ArF excimer laser. The main film-forming resin required for the corresponding photoresist has also developed from cyclized rubber, polyvinyl alcohol cinnamate to novolak resin, and then to poly-p-hydroxystyrene, polyester cyclophatic acrylate ...

Claims

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Application Information

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IPC IPC(8): C08G8/24G03F7/004
CPCC08G8/24G03F7/004
Inventor 王富成苏志强赵鑫马铮
Owner 浙江自立高分子化工材料有限公司
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