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Thiopene-containing photo acid generators for photolithography

A technology of photoacid generator and thiophene, which is applied in the field of photoacid generator containing thiophene and chemically amplified resist composition, and can solve the problem of high absorption

Inactive Publication Date: 2008-11-12
GLOBALFOUNDRIES INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in general, such photoacid generators absorb too much when exposed to wavelengths shorter than 220 nm.

Method used

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  • Thiopene-containing photo acid generators for photolithography
  • Thiopene-containing photo acid generators for photolithography
  • Thiopene-containing photo acid generators for photolithography

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Synthesis of dimethyl-(2-thienyl)sulfonium perfluorobutane sulfonate

[0064] To a mixture containing 1.07g (0.0082mol) of 2-(methylthio)thiophene and 3.55g (0.0246mol) of methyl iodide in 20ml of nitromethane at room temperature, add 3.34 to 50ml of nitromethane. g (0.0082mol) silver perfluorobutane sulfonate solution. The resulting mixture was stirred at room temperature for about 15 hours. The reaction mixture was filtered through Celite to remove any white precipitate therefrom. The filtrate was concentrated to about 10ml, and then precipitated into 120ml of ether. The white solid was collected by vacuum filtration and further purified by recrystallization with hexane / ethyl acetate. The final yield is 2.83 g (78%). The product was identified by NMR spectroscopy, and the product was dimethyl-(2-thienyl)sulfonium perfluorobutane sulfonate. The melting point is 75°C.

[0065]

Embodiment 2

[0067] Absorbency of photo acid generator (PAG) containing thiophene

[0068] 5.25 g of cycloolefin-maleic anhydride copolymer was dissolved in 34.4 g of propylene glycol monomethyl ether acetate (PGMEA). Divide the solution into two equal parts. Add 0.052 g (0.00012 mol) dimethyl-(2-thienyl)sulfonium perfluorobutane sulfonate to one portion. After the PAG is completely dissolved, both solutions are filtered through a 0.2 m pore size filter. The obtained filtrate was spin-coated on a quartz substrate, and then baked on a hot plate at about 130°C for about 60 seconds. Cary 400B io UV visible spectrophotometer was then used to measure the absorbance of the two films at 193nm. The difference between the measured two membrane absorbance is 0.03μm -1 This is caused by dimethyl-(2-thienyl)sulfonium perfluorobutane sulfonate (0.0045 mol% relative to the polymer).

[0069] For comparison, the absorbency of dimethyl(4-tolyl)sulfonium perfluorobutane sulfonate was measured in the same way. ...

Embodiment 3

[0071] Etching evaluation

[0072] For the etching test, the following materials expressed in parts by weight were combined to prepare a photoresist composition containing dimethyl-(2-thienyl)sulfonium perfluorobutane sulfonate (PAG) .

[0073] Propylene glycol monomethyl ether acetate 87.34

[0074] Poly(1-methylcyclopentyl-5-norbornene-2-carboxylate-co-5-norbornene 11

[0075] (Spirolactone-co-5-norbornene-2-carboxylic acid)

[0076] Dimethyl-(2-thienyl)sulfonium perfluorobutane sulfonate 0.33

[0077] 2,5-bis(adamatane-1-carboxyoxy)-2,5-dimethylhexane 1.32

[0078] Tetrabutylammonium hydroxide 0.011

[0079] A photoresist composition was spin-coated (within 30 seconds) on a layer of anti-reflective material (AR19, Shipley Company) coated on a silicon wafer. The photoresist layer was soft-baked on a vacuum hot plate at about 130° C. for about 60 seconds to form a film with a thickness of about 0.4 μm. The silicon wafer was then exposed to 193nm radiation (Nikonstepper, 0.6NA). T...

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Abstract

Thiophene-containing photo acid generators having either of the following general formulas:wherein at least one of R<1>, R<2 >or R<3 >is thiophene or thiophene that is substituted with alkyl, alkoxy or cycloalkyl, and the remaining R<1>, R<2 >or R<3>, not containing a thiophene moiety, are independently selected from the group consisting of alkyl, cycloalkyl and aryl, or at least one of R<1>, R<2 >or R<3 >are joined together to form a cyclic moiety having from about 4 to about 8 ring carbon atoms; and Y is a counter ion, are disclosed as well as the use thereof as a component of a chemically amplified resist composition. In addition to the thiophene-containing photo acid generator, the inventive composition includes a chemically amplified base polymer, a solvent, an optional photosensitizer, an optional base, an optional dissolution modifying agent and an optional surfactant.

Description

Technical field [0001] The present invention relates to photolithography. More specifically, the present invention relates to photo acid generators containing thiophene that can effectively generate photo acids when exposed to UV light. The present invention also relates to chemically amplified resist compositions comprising the thiophene-containing photoacid generator of the present invention as a component thereof. Background technique [0002] In the field of semiconductor production, photolithography has always been the mainstream method in patterning semiconductor devices. In a typical existing photolithography method, UV light is projected onto a silicon wafer coated with a thin layer of photoresist through a mask that defines a specific circuit diagram. After exposure to UV light, baking is performed to induce a photochemical reaction that can change the solubility of the exposed area of ​​the photoresist. Then, using a suitable developer, usually an aqueous alkaline solut...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G03F7/004G03C5/00C07C381/00C07C315/00C07C331/00C07D333/34G03F7/038G03F7/039H01L21/027
CPCG03F7/0045G03F7/0397C07C381/00C07C2103/74G03F7/0382Y10S430/122C07D333/34C07C2603/74G03F7/004
Inventor 李文杰普什卡拉·R·瓦拉纳西陈光军
Owner GLOBALFOUNDRIES INC
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