Photo-imaging Hardmask with Negative Tone for Microphotolithography

a microphotolithography and negative tone technology, applied in the field of microphotolithography, can solve the problems of difficult, if not impossible, inability to convert polysiloxane or polysilsesquioxane coatings into dielectric layers with trenches and vias, and achieve the effect of soluble or dispersibl

Inactive Publication Date: 2010-10-07
SUN SAM XUNYUN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows for easy creation of images on materials that can be easily removed without damaging them during manufacturing processes. It uses special photopolymers with specific chemical structures called acids which when exposed to light cause polymerization reaction between two different compounds like an ester group attached to each other through carbon atoms within their structure. These chemistries allow for easier removal after processing while maintaining good quality image formation over time.

Problems solved by technology

Technologies related to this patented technology involve improves upon conventional binary resist materials' ability towards increasing their contrast ratio compared to traditional nonvolatile organosilyl compounds like monoethanesulfonic acid diazide and bisphenolsimides. These techniques improve image quality but they also require higher dosage levels during processing which leads to reduced throughput rates when developing these masks. Additionally, certain types of light sources generate strong background signals, making them difficult to detect. To address these issues, new chemical structures called negativeous phase imagers were proposed.

Method used

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  • Photo-imaging Hardmask with Negative Tone for Microphotolithography
  • Photo-imaging Hardmask with Negative Tone for Microphotolithography
  • Photo-imaging Hardmask with Negative Tone for Microphotolithography

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Polysiloxane and Polysilsesquioxane Resin I

[0081]

TABLE 1Monomers for Polysiloxane and Polysilsesquioxane Resin I:Methyl trimethoxy silane (Gelest, Morrisville, PA)65.2 gramsTetraethoxy silane (Gelest, Morrisville, PA)26.6 gramsPhenyl trimethoxy silane (Gelest, Morrisville, PA)5.06 grams2-(3,4-Epoxycyclohexyl)ethyl trimethoxy silane1.57 grams(Gelest, Morrisville, PA)

[0082]Monomers in Table 1, together with 80 grams of propylene glycol methyl ether acetate (from Sigma Aldrich (Milwaukee, Wis.)), were mixed in a 500-mL three-neck round-bottom flask. Attached to the flask were distillation condenser, thermometer, and nitrogen inlet. Nitrogen flow was set at 200 milliliters per minute. With stirring, temperature of the mixture in the flask was raised to 95° C. in oil bath. Then, 50 grams of 3-nomal acetic acid were slowly added to the flask. Condensation reactions began. Volatile byproducts were distilled out of the flask and collected. Distillation completed in four hours. Hea

example 2

Synthesis of Polysiloxane and Polysilsesquioxane Resin II

[0083]

TABLE 2Monomers for Polysiloxane and Polysilsesquioxane Resin II:Methyl trimethoxy silane (Gelest, Morrisville, PA)67.8 gramsTetraethoxy silane (Gelest, Morrisville, PA)26.6 grams2-(3,4-Epoxycyclohexyl)ethyl trimethoxy silane3.14 grams(Gelest, Morrisville, PA)

[0084]Monomers in Table 2, together with 80 grams of propylene glycol methyl ether acetate (from Aldrich, Milwaukee, Wis.), were mixed in a 500-mL three-neck round-bottom flask. Attached to the flak were distillation condenser, thermometer, and nitrogen inlet. Nitrogen flow was set at 200 milliliters per minute. With stirring, temperature of the mixture in the flask was raised to 95° C. in oil bath. Then, 50 grams of 3-normal acetic acid were slowly added to the flask. Condensation reactions began. Volatile byproducts were distilled out of the flask and collected. Distillation completed in four hours. Heating stopped immediately after distillation is finished. Totally

example 3

Negative-Tone Photo-Imageable Hardmask Composition I

[0085]

TABLE 3Ingredients of Negative-tone Photo-imageable Hardmask Composition IResin I (from Example 1)38 gDiphenylsilanediol (Gelest, Morrisville, PA)0.2 gTriphenylsulfonium tris(trifluoromethyl)methide0.04 g(Ciba,Basel, Switzerland)Benzyltriethylammonium chloride0.01 g(Aldrich, Milwaukee, WI)Propylene glycol methyl ether acetate100 g

[0086]Composition I was made by mixing the ingredients in Table 3. When all the solids dissolved, the composition was filtered through a membrane with 0.02-micrometer pores. In the composition, film-modifier, that is diphenylsilanediol, is 5% of the resin by weight. Molar ratio of photoacid generator, that is triphenylsulfonium tris(trifluoromethyl)methide, to quencher, that is benzyltriethylammonium chloride, is 4 to 3. Photoacid generator load is 0.029% of total composition weight.

Lithographic Conditions for Composition I:Wafer spin speed for coating1500-3000 revolutions per minute for filmthickness o

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Abstract

Disclosed is a method of making polysiloxane and polysilsesquioxane hardmask layer photo-imageable with a negative tone. The method is based on a photosensitizer and film modifier. The film modifier reduces pore size of the hardmask films for diffusion control. The negative-tone photo-imageable hardmask is especially beneficial for forming trenches and vias on exposure tools of extreme UV and deep UV lithography. Compositions of negative-tone photo-imageable hardmask based on the chemistry of polysiloxane and polysilsesquioxanes are disclosed as well. Further disclosed are processes of using photo-imageable hardmasks to create isolated trenches or vias on semiconductor substrates with or without an intermediate layer.

Description

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Claims

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Application Information

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Owner SUN SAM XUNYUN
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