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Light-absorbing polymers and application thereof to antireflection film

A polymer, light absorption technology, applied in the direction of radiation-absorbing coatings, coatings, photosensitive materials for opto-mechanical equipment, etc. Controlling coating thickness and other issues

Inactive Publication Date: 2000-06-28
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Among these methods, the method of dispersing the light-absorbing dye in the resist has problems in that the sensitivity of the resist is lowered, and the resist layer becomes thinner during the development and sublimation of the dye during the baking process.
On the one hand, there are problems with the use of inorganic antireflective coatings, such as difficulty in precisely controlling the coating thickness, difficulty in forming a coating with a uniform thickness, requiring special equipment for vacuum deposition, poor adhesion to resist films, and in order to Another dry etching process is required to transfer the pattern
Furthermore, the method of dispersing a light-absorbing dye in an antireflective coating has a problem that, after the antireflective coating is formed by spin coating, the dye is separated from the polymer, the dye is eluted into the resist solvent, and The dye sublimes into the resist film during baking
However, such an antireflection coating material for DUV does not exist at present, especially it has the same characteristics as AZ  -BAR Li  Similar or greater simultaneous coverage with other excellent properties such as excellent light absorption properties, etch properties and adhesion to substrates

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]7.2g of 1-naphthol was dissolved in 300g of cyclohexanone, then at room temperature and under stirring, gradually added 17.4g of commercially purchased poly(maleic anhydride-co-methyl vinyl ether) powder (18459-4 , produced by Aldrich Co.). After adding, the reaction mixture was heated to 140° C., and after reacting at this temperature for 4 hours, the reaction solution was cooled to 100° C. or a lower temperature, and then 13.7 g of N-(2,4-dinitrobenzene was added base) phenylenediamine (disperse yellow 9), and the reaction mixture solution was heated to 140° C. for 4 hours. Then, the reaction solution was cooled to room temperature, and the reaction solution was precipitated with isopropanol. The precipitate was collected by filtration and dried under vacuum to obtain 31 g of polymer solid. The GPC analysis that adopts the dimethylformamide that adds lithium chloride as mobile phase and polyethylene oxide as standard substance shows that the weight-average molecular ...

Embodiment 2

[0042] Dissolve 9.7 g of 9-hydroxyanthracene in 320 g of cyclohexanone, then gradually add 17.4 g of commercially purchased poly(maleic anhydride-co-methyl vinyl ether) powder (18459-4 , produced by Aldrich Co.). After adding, the reaction mixture was heated to 140° C., and after reacting at this temperature for 4 hours, the reaction solution was cooled to 100° C. or a lower temperature, and then 13.7 g of N-(2,4-dinitrobenzene was added base) phenylenediamine (disperse yellow 9), and the reaction solution was heated to 140° C. for 4 hours. Then, the reaction solution was cooled to room temperature, and the reaction solution was precipitated with isopropanol in a conventional manner. The precipitate was dried under vacuum to obtain 33 g of polymer solid. The GPC analysis that adopts the dimethylformamide that adds lithium chloride as mobile phase and polyethylene oxide as standard substance shows that the weight-average molecular weight (Mw) of the polymer obtained is 54,000...

Embodiment 3

[0043] The phenol of 4.7g is dissolved in the cyclohexanone of 280g, then under stirring at room temperature, add gradually the poly(maleic anhydride-co-methyl vinyl ether) powder (18459-4, by Aldrich Co. production). After adding, the reaction mixture was heated to 140° C., and after reacting at this temperature for 4 hours, the reaction solution was cooled to 100° C. or a lower temperature, and then 9.65 g of 1-aminoanthracene was added, and then the reaction solution was heated at 140° C. C for 4 hours. Thereafter, the reaction solution was cooled to room temperature, and the reaction solution was precipitated with isopropanol in a conventional manner. The obtained precipitate was dried in vacuo to obtain 25 g of polymer solid. The GPC analysis that adopts the dimethylformamide that adds lithium chloride as mobile phase and polyethylene oxide as standard substance shows that the weight-average molecular weight (Mw) of the polymer obtained is 50,000, and the number-average...

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Abstract

A high-performance antireflection film which highly absorbs a given light, e.g., far ultraviolet, tenaciously adheres to substrates upon film formation, is satisfactory in covering, and eliminates the influence of standing waves in the production of integrated circuits; novel light-absorbing polymers for forming the antireflection film; and a process for producing the polymers. One of the polymers is produced by esterifying a copolymer comprising carboxylic anhydride groups and / or dicarboxylic acid groups such as maleic acid as basic repeating units with a hydroxylated aromatic chromophore. The unreacted carboxylic acid groups or acid anhydride groups remaining in the esterified light-absorbing polymer may be amidated and / or imidized with an aminated aromatic compound. These polymers each is dissolved in an organic solvent comprising an alcohol, aromatic hydrocarbon, ketone, ester, or combination of these, and the solution is applied to a substrate and then baked to form an antireflection film.

Description

field of invention [0001] The present invention relates to a kind of light-absorbing polymer and the application of anti-reflection coating thereof, in particular, the present invention relates to the light-absorbing polymer suitable for forming anti-reflection coating in the production of micro components such as integrated circuit components by photolithography Object, as well as the preparation method of the polymer, the film-forming composition containing the light-absorbing polymer and the antireflection coating formed therefrom. Background technique [0002] In the field of producing integrated circuit components, in order to achieve a higher degree of integration in the production process of integrated circuit components, people have been conducting research on reducing the processing size miniaturization in the lithography process; in recent years, this technology has been developed to be able to perform sub- Micron-scale microprocessing. In this lithographic method...

Claims

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Application Information

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IPC IPC(8): H01L21/027C08F8/14C08F8/30C08F8/32C08F222/02C08F222/04C09D5/32G03F7/09G03F7/11
CPCC08F8/30C09D5/32G03F7/091C08F8/14C08F220/00
Inventor 康文兵西胁良典木村健松尾祥子田中初幸
Owner MERCK PATENT GMBH
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