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Imprint product and method for producing the same

Inactive Publication Date: 2011-12-08
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0015]It is an object of the present invention to provide an imprint product having a fine pattern on the surface, which is formed by transcribing a fine pattern on a mold surface with high dimensional accuracy. The object of the present invention is achieved by using a specific fluorine-containing cyclic olefin polymer and thereby optimizing the changes in the elastic modulus and shrinkage ratio of the resin during the heating and cooling processes in the manufacturing process for a nanoimprint product. Another object of the present invention is to provide a method for manufacturing an imprint product which can efficiently produce an imprint product with high dimensional accuracy, and is capable of obtaining an imprint product with a large area by simple and convenient processes; a method for producing a cured product in which a fine pattern has been transcribed onto the surface of a photocured resin by using the imprint product as a replica mold; and a resin composition for pattern transfer, which is capable of molding the imprint product of the present invention.
[0042]According to the present invention, since a specific fluorine-containing cyclic olefin polymer having a hydrocarbon structure in the main chain and a fluorine-containing aliphatic cyclic structure in a side chain is used, hydrogen bonding can be formed between the molecules or within the molecule, and thereby changes in the elastic modulus and shrinkage ratio of the resin during the heating and cooling processes in the production process of a nanoimprint imprint product can be optimized. Thus, an imprint product having a fine pattern formed on the surface, which is formed by transcribing a fine pattern of a mold surface with high dimensional accuracy, can be formed, and an imprint product with a large area can be obtained by simple and convenient processes. This imprint product is excellent in releasability and exhibits high production efficiency, such that the imprint product is industrially valuable.

Problems solved by technology

However, all of the above-described nanoimprint methods have problems that the shape accuracy of the fine pattern in an imprint product is decreased because the mold can not be smoothly released in a process of releasing the mold.
In this case, there is a problem in which the pattern accuracy of the mold is decreased due to unevenness of the thickness of the release agent layer, and there is also a problem in which the releasing agent layer becomes thinning when the mold is continuously used, and it is necessary to reapply the release agent on the mold, which lowers productivity.
Furthermore, a mold using silicone has a low elastic modulus, and it is difficult to imprint a pattern shape accurately as using such a mold.
However, when the fluorine content of these polymers is 60% by mass or less, their dimensional accuracy in terms of the depth, width and interval of convex structures is low and dimensional difference is large, because the elastic modulus is rapidly decreased at a temperature above the glass transition temperature, and after the polymer is subjected to press molding, when cooling rapidly, the shrinkage ratio is increased due to the decreased elastic modulus.
Furthermore, the fluorine resins must be decomposed when heated at temperature of 300° C. or higher to generate hydrogen fluoride gas, which associate with a high possibility of decomposition of the fluorine resins when heated at the temperature of 260° C. Thus, problems such as corrosion of the mold and peripheral devices, or environmental contamination, are caused.
Thus, there is a large problem in manufacturing an imprint product with a large area because of limitations on the area of the imprint product that can be industrially processed.

Method used

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  • Imprint product and method for producing the same
  • Imprint product and method for producing the same
  • Imprint product and method for producing the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of poly(1,1,2-trifluoro-2-trifluoromethyl-3,5-cyclopentylene ethylene)

[0167]A tetrahydrofuran solution of 5,5,6-trifluoro-6-(trifluoromethyl)bicyclo[2.2.1]hept-2-ene (100 g) and 1-hexene (268 mg) was mixed with a tetrahydrofuran solution of Mo (N-2,6-Pri2C6H3) (CHCMe2Ph) (OCMe(CFA2)2 (70 mg), and ring-opening metathesis polymerization was carried out at 70° C. The olefin moiety of the polymer thus obtained was subjected to a hydrogenation reaction using palladium alumina (5 g) at 160° C., and thus a tetrahydrofuran solution of poly(1,1,2-trifluoro-2-trifluoromethyl-3,5-cyclopentylene ethylene) was obtained.

[0168]The solution was added to methanol, and a white polymer was separated by filtration and was dried. Thus, 99 g of a polymer was obtained. The hydrogenation rate was 100%, the weight average molecular weight (Mw) was 127,000, the molecular weight distribution (Mw / Mn) was 1.70, and the glass transition temperature was 109° C. The fluorine atom content rate was 52.3% b...

example 2

Synthesis of poly(1,1,2-trifluoro-2-trifluoromethyl-3,5-cyclopentylene ethylene)

[0170]The synthesis was carried out in the same manner as in Example 1, except that the catalyst was changed to Mo(N-2,6-Pri2C6H3)(CHCMe2Ph)(OBut)2 (50 mg), and thus poly(1,1,2-trifluoro-2-trifluoromethyl-3,5-cyclopentylene ethylene) was obtained (98 g). The hydrogenation rate was 100%, the weight average molecular weight (Mw) was 83,000, the molecular weight distribution (Mw / Mn) was 1.73, and the glass transition temperature was 108° C. The fluorine atom content rate was 52.3% by mass.

[0171]Subsequently, a powder of the hydrogenated polymer thus obtained was treated by heat pressing, and thus a heat pressed sheet having a thickness of 0.37 mm was produced. From the results of the dynamic mechanical analysis by tensile mode carried out, it was found that a flat region of variation in storage modulus or loss modulus in the range of temperature which is not less than the glass transition temperature lies i...

example 3

Synthesis of poly(1,2-difluoro-1-trifluoromethyl-2-perfluoroethyl-3,5-cyclopentylene ethylene)

[0172]The synthesis was carried out in the same manner as in Example 1, except that the monomer was changed to 5,6-difluoro-5-trifluoromethyl-6-perfluoroethylbicyclo[2.2.1]hep t-2-ene (50 g), and the catalyst was changed to Mo (N-2,6-Pri2C6H3) (CHCMe2Ph) (OBut)2 (17 mg), and thus poly(1,2-difluoro-1-trifluoromethyl-2-perfluoroethyl-3,5-cyclopentylene ethylene) was obtained (49 g). The hydrogenation rate was 100%, the weight average molecular weight (Mw) was 95,000, the molecular weight distribution (Mw / Mn) was 1.52, and the glass transition temperature was 110° C. The fluorine atom content rate was 59.7% by mass.

[0173]Subsequently, a powder of the hydrogenated polymer thus obtained was treated by heat pressing, and thus a heat pressed sheet having a thickness of 0.37 mm was produced. From the results of the dynamic mechanical analysis by tensile mode carried out, it was found that a flat re...

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Abstract

Provided is an imprint product, which is for transcribing a fine pattern of a mold surface and which contains a fluorine-containing cyclic olefin polymer containing repeating unit represented by formula (1) and having a fluorine atom content rate of 40% to 75% by mass.

Description

TECHNICAL FIELD[0001]The present invention relates to an imprint product in which a fine pattern is formed, and a method for producing the same.BACKGROUND ART[0002]A resin molding product having a fine pattern is useful such as an optical element (such as a micro lens array, an optical waveguide, an optical switch, a Fresnel zone plate, a binary optical element, a blaze optical element, a photonic crystal), an antireflection filter, a biochip, a microreactor chip, a recording medium, a display material, a catalyst support, or the like. In recent years, there has been a demand for further refinement of such patterns, along with a demand for miniaturization of devices. As a method for manufacturing a resin molding product having such a fine structure on the surface, there has been suggested a method for manufacturing an imprint product having a fine pattern formed thereon by transcribing the pattern on a mold having a fine pattern to a resin, that is, a so-called nanoimprint method (f...

Claims

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Application Information

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IPC IPC(8): C08F36/20B29C59/16B29C59/02B29C33/42
CPCB82Y10/00B82Y40/00C08G61/08C08G2261/146B29C59/005C08G2261/418C08L65/00G02B3/0031G03F7/0002C08G2261/3324H01L21/0274
Inventor SUNAGA, TADAHIROODA, TAKASHIONISHI, HITOSHI
Owner MITSUI CHEM INC
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