Polymer and resist compound having same polymer

A polymer and resist technology, applied in organic chemistry, photoengraving process of pattern surface, photosensitive materials for opto-mechanical equipment, etc., can solve problems such as corrosion resistance reduction, pattern cracking, and problem deterioration , to achieve excellent contrast, prevent thickness loss, and improve the effect of

Active Publication Date: 2014-10-29
SK MATERIALS PERFORMANCE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For polarity switching, in the case of conventional 193nm photoresists that only require bulky acid-labile groups as above, the thickness loss is exacerbated by the high content of the above groups
In order to solve the above problems, if a thicker resist layer is used, other problems such as pattern cracking and focus loss may occur, so no practical solution can be given
In addition, the pattern cracking that occurs in the case of using a typical 193nm photoresist in NTD is due to the specific acid-labile groups that undergo polarity switching from the (meth)acrylate base polymer, especially alone. groups, such as cleavage of tertiary alkyl esters and acetal leaving groups, the problem is exacerbated by the generation of larger numbers of (meth)acrylic acid units in the exposed areas of the photoresist
In addition, in the case where such a conventional photoresist, which relies solely on the above-mentioned relatively polar acid-labile group for polarity switching, is used for NTD, there is another problem in that corrosion resistance is lowered.

Method used

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  • Polymer and resist compound having same polymer
  • Polymer and resist compound having same polymer
  • Polymer and resist compound having same polymer

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0196] In a jacketed (jacket) reactor of 1L, the air in the reactor was purged with nitrogen, and under a nitrogen atmosphere, 52g of norbornene (norbornene), 43g of γ-butyrolactone acrylate ( γ-butyrolactone acrylate), 40 g of ethoxy ethyl methacrylate (ethoxy ethyl methacrylate) were dissolved in 405 g of 1,4-dioxane (1,4-dioxane). While stirring the obtained solution, 12.8 g of dimethyl azobisisobutyrate (DMAB, dimethyl azobis butyronitrile) was added as an initiator, and the temperature of the oil bath was gradually raised to 75° C. Stir at 75°C for 3 hours. After the reaction was completed, the temperature of the reaction solution was lowered to normal temperature, and the precipitation reaction was performed using n-hexane, followed by vacuum filtration. The obtained filtrate was dried at 50° C. for one day to obtain 105 g of a polymer (10a).

[0197]

[0198] (In the above formula, the molar ratio (a:c:b) of each repeating unit is 0.3:0.3:0.6)

[0199] The prepare...

Synthetic example 2

[0203] In a 1L jacketed (jacket) reactor, use nitrogen to purge the air in the reactor (purge), under a nitrogen atmosphere, 36g of ethoxyethyl methacrylate (ethoxyethyl methacrylate), 52g of Norbornane carbolactone methacrylate and 51 g of adamantine methacrylate were dissolved in 405 g of 1,4-dioxane. While stirring the obtained solution, 16 g of dimethyl azobisisobutyrate (DMAB, dimethyl azobis butyronitrile) was added as an initiator, and the temperature of the oil bath was slowly raised to 75° C. Stir at °C for 3 hours. After the reaction was completed, the temperature of the reaction solution was lowered to normal temperature, and the precipitation reaction was performed using n-hexane, followed by vacuum filtration. The obtained filtrate was dried at 50° C. for one day to obtain 123 g of a polymer (10b).

[0204]

[0205] (In the above formula, the molar ratio (a:c:d) of each repeating unit is 0.33:0.33:0.33)

[0206] The prepared polymer was measured by gas chrom...

Synthetic example 3

[0210] In a 1L jacket (jacket) reactor, use nitrogen to purge (purge) the air in the reactor, under nitrogen atmosphere, 38g of tetrahydrofuran methacrylate (tetrahydropyran methacrylate), 52g of norbornanyl carbon lactone Norbornane carbolactone methacrylate and 51 g of hydroxyadamantane methacrylate were dissolved in 405 g of 1,4-dioxane. While stirring the obtained solution, 16 g of dimethyl azobisisobutyrate (DMAB, dimethyl azobis butyronitrile) was added as an initiator, and the temperature of the oil bath was slowly raised to 75° C. Stir at °C for 3 hours. After the reaction was completed, the temperature of the reaction solution was lowered to normal temperature, and the precipitation reaction was performed using n-hexane, followed by vacuum filtration. The obtained filtrate was dried at 50° C. for one day to obtain 115 g of a polymer (10c).

[0211]

[0212] (In the above formula, the molar ratio (a:c:d) of each repeating unit is 0.33:0.33:0.33)

[0213] The prep...

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Abstract

The invention provides a resist compound in a reverse development mode and a resist compound having the same polymer. During formation of a picture using photoetching technology and particular an NTD method, thickness reduction and decrease of the corrosion resistance of the resist caused by thickness reduction are prevented, thereby being beneficial for formation of a micro anti-corrosion picture excellent in light sensitivity and resolution. In particular, the improvement effect of contrast ratio is obvious.

Description

technical field [0001] The present invention relates to a polymer used for pattern formation by photolithography and a resist composition containing the polymer. Background technique [0002] Recently, in lithography technology, mass production (HVM, high volume manufacturing) using ArF immersion lithography technology (immersion) is being actively carried out, and technology development for realizing a line width of 50 nm or less is mainly carried out. In particular, research on negative-tone development (NTD, negative-tone development) has been actively conducted as a method for realizing a contact hole pattern with a line width of 30 nm. [0003] The NTD method differs from the conventional PTD (positive-tone development) method in that an organic solvent is used as a developer. That is, the acid-labile group (acid-labile group) is deprotected by generating acid in the exposed part, and the PTD method of washing with tetramethylammonium hydroxide (TMAH, tetramethylammoni...

Claims

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Application Information

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IPC IPC(8): C08F232/08C08F220/28C08F220/18C08F222/20C08F212/14G03F7/004G03F7/00
CPCC07C69/013G03F7/004G03F7/0045G03F7/0047
Inventor 朱炫相裵昌完安浩益吴贤锡
Owner SK MATERIALS PERFORMANCE CO LTD
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