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Polymer and corrosion resistant material

A technology of polymers and compounds, applied in the field of polyhydroxystyrene derivatives, can solve the problems of substrate dependence, poor solvent retention ability, and poor adhesion during the delay period of poor resolution

Inactive Publication Date: 2004-04-07
WAKO PURE CHEMICAL INDUSTRIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, like the aforementioned resist materials, since the groups removed by acid are also tert-butyl, tert-butoxycarbonyl, tetrahydropyranyl, etc., these resist materials also have problems of poor resolution and delay period. and substrate dependence etc disadvantages
[0008] As mentioned earlier, the existing chemically amplified resist materials cannot be practically applied because they still have many problems, such as the poor heat resistance of the polymer used as the main component, poor adhesion to the substrate, and resistance to nearly 248.4nm Poor light transmission, poor solvent retention, insufficient chemical enhancement, poor resolution due to uneven development rate during development, pattern size and shape changes over time (so-called "problem during delay") , poor storage stability, unclear focus boundary, poor mask linearity, footing (pattern bottom is wider) and dross, pattern sidewall rough, substrate dependent, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0330] Synthesis of poly[p-(1-ethoxyethoxy)styrene / p-hydroxystyrene]

[0331] (1) Suspend 15.9 g of poly(p-tert-butoxystyrene) [manufactured by Nippon Soda Co., Ltd.; Mw about 21,000; molecular weight distribution (dispersion index) 1.16] in isopropanol and add 30 ml concentrated hydrochloric acid, followed by reflux and stirring for 4 hours. After cooling, the reaction solution was poured into 3000 ml of water for crystallization. Crystal precipitates were filtered off, washed with water and dried under reduced pressure to obtain 10.5 g of poly(p-hydroxystyrene) white powder crystals.

[0332] (2) The poly(p-hydroxystyrene) obtained in (1) above was dissolved in 80 ml of ethyl acetate in an amount of 8 g and 2.4 g of ethyl vinyl ether. After adding a catalytic amount of pyridinium p-toluenesulfonate, the reaction was stirred at room temperature for 2 hours. After the reaction, the reaction solution was concentrated at room temperature under reduced pressure, and the residu...

preparation Embodiment 2

[0334] Synthesis of poly[p-(1-methoxyethoxy)styrene / p-hydroxystyrene].

[0335] The poly(p-hydroxystyrene) obtained by the method described in Preparation Example 1 (1) was reacted in an amount of 8 g and 2.2 g of methyl vinyl ether in the same manner as described in Preparation Example 2 (1). And aftertreatment, obtain the white powder of 8.6g poly [p-(1-methoxyethoxy) styrene / p-hydroxystyrene] without crystallization. The ratio of p-(1-methoxyethoxy)styrene to p-hydroxystyrene in the resulting polymer was about 4:6 as measured by 'H-NMR. Its Mw is about 17000 and its dispersion index is 1.16 (GPC method, polystyrene as calibration).

preparation Embodiment 3

[0337] Synthesis of poly[p-(1-ethoxyethoxy)styrene / p-hydroxystyrene / p-isobutoxycarbonyloxystyrene].

[0338] (1) Poly(p-hydroxystyrene) [manufactured by Nippon Soda Co., Ltd.; Mw about 8200, dispersion index 1.05] was dissolved in 70 ml of ethyl acetate in an amount of 18.0 g. Then, 3.5 g of diisobutyl dicarbonate synthesized from isobutyl chlorocarbonate and 3.0 g of triethylamine were added, and the reaction was carried out at room temperature for 4 hours. After the reaction, ethyl acetate was distilled off under reduced pressure and the residue was dissolved in 70 ml of acetone. After pouring 1000 ml of water, crystals precipitated out. The crystal precipitate was filtered off, washed with water and dried under reduced pressure to obtain 13.5 g of white powder crystals of poly(p-hydroxystyrene / p-isobutoxycarbonyloxystyrene). The ratio of p-hydroxystyrene units to p-isobutoxycarbonyloxystyrene units was about 92:8 as measured by 'H-NMR.

[0339] (2) The poly(p-hydroxystyr...

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Abstract

A polymer of polyhydroxystyrene derivative containing an acetal or ketal group which can easily be eliminated in the presence of an acid in the molecule and having a very narrow molecular weight distribution gives a resist material suitable for forming ultrafine patterns excellent in resolution, heat resistance, mask linearity, and other properties without causing problems of delay time and the like.

Description

technical field [0001] The present invention relates to a polyhydroxystyrene derivative having an acetal group or a ketal group which is easily removed in the presence of an acid in its molecule, especially a polyhydroxystyrene derivative which has a narrow molecular weight distribution and can be used as a resist material Polyhydroxystyrene derivatives of functional polymers. Background technique [0002] As semiconductor devices become increasingly densely integrated, the wavelengths used for light sources for finer processing, especially for exposure devices for photolithography, are getting shorter and shorter. The use of far ultraviolet rays (300nm or less), KrF excimer laser beams (248.4nm) and the like have been studied. However, no resist material particularly suitable for these wavelengths has been found. [0003] For example, as a resist material that can be used for KrF excimer laser beams and extreme ultraviolet light sources, it is required to have high transm...

Claims

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Application Information

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IPC IPC(8): G03F7/004C08F212/14C08K5/41C08L25/16G03F7/039H01L21/027
CPCG03F7/0045Y10S430/106C08F212/14G03F7/039C08F212/24C08F212/22C09D125/18
Inventor 浦野文良藤江启利大野桂二
Owner WAKO PURE CHEMICAL INDUSTRIES
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