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Polymer, chemical range enlargement erosion resistant component and forming method

A technology of polymer and mixture, applied in the field of polymer, chemically amplified resist composition and formation, can solve the problems of uneven circuit, line obstacle, long dissolution time, etc.

Inactive Publication Date: 2006-02-22
MITSUBISHI CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] However, when the propylene-based series resin and the cycloalkenyl-based series resin are prepared with the resist solution, due to insufficient solubility, the dissolution time will be long or even insoluble, which makes the preparation of the resist solution very difficult.
In addition, the heat resistance of the acrylic series resins and cycloolefin series resins is insufficient. When using the acrylic series resins and cycloolefin series resins, after being treated by excimer laser lithography, resistance to heat will appear. Erosion-type local impurities, line obstacles, uneven circuits and short circuits, etc., have caused concerns for the semiconductor manufacturing industry

Method used

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  • Polymer, chemical range enlargement erosion resistant component and forming method
  • Polymer, chemical range enlargement erosion resistant component and forming method
  • Polymer, chemical range enlargement erosion resistant component and forming method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0367] In a 500ml eggplant-shaped flask equipped with a circulating cooling tube, add 2,5 dimethyl 2-(1-adamant compound)-1,3-dioxolan-4-one 25.0g (0.1 mol); add bromine 19.6 g (0.11 mol) of succinimide; 240 g of heptane was added, and the reaction temperature was raised to 60° C. while stirring to form a paste.

[0368] After stirring at 60° C. for about 2 hours, the color of the reaction solution turned brown, and after continuing to stir for 2 hours, the color of the reaction solution turned transparent. After cooling the reaction solution in an ice bath, filter to remove succinic acid imide, distill off the solvent, and purify the obtained transparent liquid with a column to obtain 5-bromo-2,5-dimethyl 2-(1-adamantine compound )-1,3-dioxolan-4-one 28.6g (Formula 18), (87% recovery).

[0369]

[0370] Elemental analysis: C54.56%, H6.64%, N0%, O14.73%.

[0371] Theoretical values: C54.72%, H6.43%, N0%, O14.58%.

[0372] Br content (flask combustion ion chromatography):...

Embodiment 2

[0380] In a 500ml eggplant-shaped flask equipped with a reflux cooling tube, add 22.2g (0.1mol ); add 21.4 g (0.12 mol) of bromosuccinimide; add 200 g of cyclohexane, and stir to form a paste while raising the reaction temperature to 60°C.

[0381] After stirring at 60° C. for about 2 hours, the color of the reaction solution turned brown, and continued stirring for another 2 hours, and the color of the reaction solution turned transparent. After cooling the reaction liquid in an ice bath, succinimide was removed by filtration, and the solvent was distilled off. The precipitated crystals were recrystallized with hexane to obtain 25.6 g of spiro[adamantane-2,2'-(5'-methanol-1',3'-dioxolan-4-one)] (Formula 20) , (85% recovery).

[0382]

[0383] Elemental analysis: C51.70%, H5.82%, N0%, O16.19%.

[0384] Theoretical values: C51.84%, H5.69%, N0%, O16.94%.

[0385] Br content (flask combustion ion chromatography): 25.4% (theoretical value 26.53%).

[0386] H-NMR (270MHz, -...

Embodiment 3

[0394] In a 500ml eggplant-shaped flask equipped with a reflux cooling tube, add spiro[norbornane-2,2'-(5'-methanol-1',3'-dioxolane-4'-one)] 18.2 g (0.1 mol); add 16.9 g (0.11 mol) of N-bromosuccinimide; add 280 g of cyclohexane, and stir to form a paste while raising the reaction temperature to 60°C.

[0395] After stirring at 60° C. for about 2 hours, the color of the reaction solution turned brown, and continued stirring for another 2 hours, and the color of the reaction solution turned transparent. After the reaction solution was cooled in an ice bath, the analysis result contained 25.1 g of spiro[norbornane-2,2'-(5'-methanol-1',3'-dioxolane-4'-one)], (Formula 22), (96% recovery).

[0396]

[0397] After transferring the obtained liquid into a 100 ml eggplant-shaped flask, 70.0 g (1.0 mol) of N·N-dimethylamide was added, followed by vigorous stirring at room temperature for 2 hours. The succinimide produced in the previous step was dissolved in N-dimethylamide while s...

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Abstract

The invention aims to provide a novel monopolymer and a preparation method thereof. The monopolymer has the polymerization characteristic suitable for the copolymerization with other monopolymers; and has excellent light transparency and heat stability, no loss of sensitivity, resolution and dry etching resistance, good solubility in organic solvents and small line edge roughness. The invention also provides a preparation method. The method is applicable for a resist composition used in deep ultraviolet excimer laser lithography and electron beam lithography, and patterns (samples) using the resist composition.

Description

[0001] The application date is October 22, 2002, the application number is 02146580.0, and the name of the invention is "5-methylene-1,3-dioxolane-4-one inducer, coincident body, chemically amplified resist Composition and Formation Method" divisional application. technical field [0002] The present invention relates to a kind of 5-methylene-1,3-dioxolane-4-ketone derivatives contained in bridged cyclic hydrocarbons and alkyl groups containing bridged cyclic hydrocarbons as resins for coatings, adhesives and inks Raw materials for resin components such as anticorrosion materials and their manufacturing methods, and polymers important in anticorrosion applications, especially an anticorrosion polymer suitable for fine processing using excimer lasers or electron beams, and the use of The resist composition of the polymer and its formation method. Background technique [0003] There are 5-methylene-1,3-dioxolan-4-one derivatives represented by the following general formula (1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/34C07D317/72C07D319/06C07D319/08C07D325/00C08G63/00G03F7/00C07D317/18C07D317/42C08F20/30C08F24/00G03F7/039
CPCC07D317/72Y10S430/106C08F24/00Y10S430/111C08F20/30Y10S430/143G03F7/0397G03F7/0392C07D317/18C07D317/42C07D317/34
Inventor 安齐龙一加门良启藤原匡之桑野英昭大竹敦百濑阳
Owner MITSUBISHI CHEM CORP
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