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Preparation of 248 nm deep ultraviolet photoresist film forming resin based on RAFT polymerization method

A technology of deep ultraviolet light and film-forming resin, which is applied in the direction of photosensitive materials, optics, and optomechanical equipment used in optomechanical equipment. And molecular weight, simple polymer structure and other issues, to achieve the effect of increasing light transparency, improving solubility, and broadening the application field

Active Publication Date: 2016-01-13
SUZHOU RUIHONG ELECTRONIC CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, photosensitive resins are mainly formed by traditional free radical polymerization, and traditional free radical polymerization is prone to side reactions such as free radical coupling, disproportionation, and chain transfer during the polymerization process, and it is usually difficult to control the molecular structure and molecular weight of the polymer. In most cases, only linear homopolymers and homeless copolymers can be obtained, and the obtained polymers have a simple structure and a wide molecular weight distribution (Mw / Mn>1.8), but the sequence structure and three-dimensional structure of the polymer cannot be controlled, which limits its Application range

Method used

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  • Preparation of 248 nm deep ultraviolet photoresist film forming resin based on RAFT polymerization method
  • Preparation of 248 nm deep ultraviolet photoresist film forming resin based on RAFT polymerization method
  • Preparation of 248 nm deep ultraviolet photoresist film forming resin based on RAFT polymerization method

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Experimental program
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Effect test

Embodiment 1

[0016] Synthesis of 248nm photoresist copolymer by RAFT method: according to the proportion of raw materials, add 4.379g p-acetoxystyrene (ASM), 0.937g styrene (St), 0.577g acrylic acid tertiary Butyl ester (TBA), 1.054g 2-methyl-2-adamantyl methacrylate (MAMA), 0.016g azobisisobutyronitrile (AIBN), 0.073g RAFT reagent and 13.06g solvent propylene glycol methyl ether acetate, to Nitrogen was passed through the flask for 30 minutes to remove oxygen, and then sealed, placed in an oil bath at 80°C for 20 hours, then 2.02 g of sodium methoxide and 10 g of methanol were added for alcoholysis for 5 hours, the resulting product was dissolved in acetone, water was used as a precipitant, and the precipitate was dissolved for 3 times. The solid was dried in a vacuum oven at 30°C to obtain a white solid. The RAFT method synthesizes this 248nm copolymer infrared spectrum as figure 2 shown.

[0017] figure 2 The middle a and b are the infrared spectra before and after the alcoholysis ...

Embodiment 2

[0021] Synthesis of 248nm photoresist copolymer by RAFT method: according to the proportion of raw materials, add 4.379g p-acetoxystyrene (ASM), 0.937g styrene (St), 0.577g acrylic acid tertiary Butyl ester (TBA), 1.054g 2-methyl-2-adamantyl methacrylate (MAMA), 0.016g azobisisobutyronitrile (AIBN), 0.1094g RAFT reagent and 13.06g solvent propylene glycol methyl ether acetate, to Nitrogen was passed through the flask for 30 minutes to remove oxygen, and then sealed, placed in an oil bath at 80°C for 20 hours, then 2.02 g of sodium methoxide and 10 g of methanol were added for alcoholysis for 5 hours, the resulting product was dissolved in acetone, water was used as a precipitant, and the precipitate was dissolved for 3 times. The solid was dried in a vacuum oven at 30°C to obtain a white solid. The 248nm copolymer red was synthesized by the RAFT method.

[0022] The preparation and development test of the photoresist composition, the mass percentages of each component are as ...

Embodiment 3

[0025] Synthesis of 248nm photoresist copolymer by RAFT method: according to the proportion of raw materials, add 4.379g p-acetoxystyrene (ASM), 0.937g styrene (St), 0.577g acrylic acid tertiary Butyl ester (TBA), 1.054g 2-methyl-2-adamantyl methacrylate (MAMA), 0.016g azobisisobutyronitrile (AIBN), 0.1458g RAFT reagent and 13.06g solvent propylene glycol methyl ether acetate, to Nitrogen was passed through the flask for 30 minutes to remove oxygen, and then sealed, placed in an oil bath at 80°C for 20 hours, then 2.02 g of sodium methoxide and 10 g of methanol were added for alcoholysis for 5 hours, the resulting product was dissolved in acetone, water was used as a precipitant, and the precipitate was dissolved for 3 times. The solid was dried in a vacuum oven at 30°C to obtain a white solid. The 248nm copolymer red was synthesized by the RAFT method.

[0026] The preparation and development test of the photoresist composition, the mass percentages of each component are as ...

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Abstract

The present invention discloses preparation of a 248 nm deep ultraviolet photoresist film forming resin based on a RAFT polymerization method, and belongs to the field of deep ultraviolet photoresists. According to the photoresist film forming resin, mainly 2-(dodecyl trithiocarbonate-yl)-2-methylpropanoic acid is adopted as a RAFT reagent, 4-acetoxy styrene, styrene, tert-butyl acrylate and 2-methyl-2-methacrylic acid adamantine ester are adopted as copolymerization monomers, 1-methoxy-2-propyl acetate is adopted as a reaction solvent to carry out solution polymerization under the condition of a free radical initiator so as to synthesize a low molecular weight distribution copolymer, a certain amount of sodium methoxide and methanol are added to carry out alcoholysis so as to obtain the copolymer having high transparency at 248 nm, and the copolymer is finally applied in the 248 nm photoresist. According to the present invention, the preparation is simple, the reaction conditions are mild, the molecular weight distribution of the obtained copolymer is narrow, the molecular weight can be well controlled, and the resin is suitable for 248 nm deep ultraviolet exposure.

Description

technical field [0001] The invention relates to the field of functional polymer materials, in particular to a RAFT method for preparing a copolymer with controllable molecular weight and distribution, which is applied to the field of 248nm deep ultraviolet photoresist. Background technique [0002] Photoresist, also known as photoresist, plays an important role in the microelectronics industry. It can be used to transfer circuit patterns to substrates to prepare microelectronic circuits by means of changes in its dissolution properties before and after exposure. [0003] Photoresist is mainly a light-sensitive mixed liquid composed of three main components: photosensitive resin, photosensitive agent and solvent. After the photosensitive resin is exposed to light, a chemical reaction can quickly occur in the exposed area, which makes the physical properties of the material, especially the solubility, change significantly. After appropriate development treatment, the soluble ...

Claims

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Application Information

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IPC IPC(8): C08F212/14C08F212/08C08F220/18C08F2/38G03F7/004G03F7/00
Inventor 刘敬成李虎刘晓亚穆启道郑祥飞刘仁纪昌炜
Owner SUZHOU RUIHONG ELECTRONIC CHEM CO LTD
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