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Photoimageable composition

a composition and composition technology, applied in the field of photoimageable compositions, can solve the problems of increasing resist thickness over diffusion steps on substrates, affecting the depth of focus of exposure tools, and affecting the accuracy of etching patterns, so as to achieve the effect of improving lithographic performance and lowering dissolution rates

Inactive Publication Date: 2005-02-03
SHIPLEY CO LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

It has been surprisingly found that the present silsesquioxane-containing polymers are suitable for use in bilayer resist systems and have lower dissolution rates than conventional silsesquioxane polymers. It has been further found that the present polymers have improved lithographic performance as compared to such conventional bilayer silsesquioxane polymers.

Problems solved by technology

However, at shorter wavelengths the depth of focus of the exposure tool, which may be an excimer stepper, or step and scan tool, may be adversely affected.
However, the major drawback of using a thin layer of resist is that the variation of resist thickness over a diffusion step on a substrate and into an etched pattern increases as the pattern size becomes smaller.
Therefore, in a single layer resist system, the lack of dimensional control on the wafer can create different line widths throughout the resist which reduces the quality of the electronic package.
However, this reaction is not highly reproducible and often gives crosslinked polymer.
Conventional silicon-containing polymers, such as the above discussed silsesquioxane polymers, for use in bilayer resist systems have dissolution rates that are too high.
Such high dissolution rates can negatively affect the lithographic performance of such bilayer resist systems.
However, such increased amount of blocking results in slower photospeeds and a reduced percentage of silicon in the resist.
Such reduced silicon content may adversely affect the etch resistance of the resist.

Method used

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Examples

Experimental program
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Effect test

example 1

Poly(4-hydroxybenzyl silsesquioxane) (254.7 g) is dissolved in 1000 mL dry acetone under nitrogen atmosphere in a dried 3 L flask (reactor). Methanesulfonyl chloride (23.8 g) is added and the reactor is cooled to 15° C. A solution of distilled triethylamine (21.9 g) and acetone (22 g) is gradually added dropwise over 20-30 minutes, maintaining a reaction temperature of less than 30° C. Stirring is continued for 3 hours, at which time the solution is added dropwise over 2 h. to 32 L of water, precipitating the polymer. The polymer is then collected by suction filtration, and suspended in 8 L of water with stirring at room temperature for 18 h. The solid is then collected by suction filtration, is washed with water until the effluent is pH neutral, air-dried for 48 h., and is then dried in vacuo for 24 h. at 70° C. to yield an off-white polymer, having the formula 95 mol % hydroxybenzylsilsesquioxane / 5 mol % mesylatedbenzylsilsesquioxane. Yield: 246 g (85% of theory). GPC data (RI de...

example 2

A polymer with a higher mesylation level of 22% per molar equivalent of hydroxybenzyl group is prepared by the method of Example 1, except that the following reagent and solvent proportions are used: poly(4-hydroxybenzyl silsesquioxane) (63.7 g) in 250 mL dry acetone; methanesulfonyl chloride (13.8 g) in 9.3 g acetone; and triethylamine (12.6 g) in 17.4 g acetone. A 1 L reaction flask is used. Workup volumes are 8 L deionized water for precipitation, and 2 L deionized water for slurrying. The resulting polymer has the formula 78 mol % hydroxybenzylsilsesquioxane / 22 mol % mesylatedbenzylsilsesquioxane. Yield: 61 g (71% of theory); GPC (RI detection): Mw=5,571, Mn=3,456; molecular weight polydispersity=1.61. Tg=97° C. Dissolution Rate (0.26 N TMAH)=5,591 Å / sec. The isolated polymer is typically between 21-23% methanesulfonated, as determined by 1H NMR and as shown by the following general formula where x=0.79-0.77 and y=0.21-0.23.

example 3

5% Mesylated poly(4-hydroxybenzyl silsesquioxane) (163.1 g) from Example 1 is dissolved in 750 mL dry acetone under nitrogen atmosphere in a dried 2 L flask (reactor). Di-t-butyl dicarbonate (65.5 g) is dissolved in 300 mL acetone and added to the reactor, followed by N,N-dimethylaminopyridine (“DMAP”, 0.25 g) dissolved in 2 mL acetone, and the resulting pale orange solution is stirred 25° C. for 25 h. The acetone solution of polymer is added dropwise over 2 h. to 24 L of water, precipitating the polymer. The polymer is then collected by suction filtration, is washed with water, and dried in vacuo at 20° C. to constant weight (ca. 72 h.) to yield an off-white polymer, having the formula 65 mol % hydroxybenzylsilsesquioxane / 5 mol % mesylatedbenzylsilsesquioxane / 30 mol % tert-butoxycarbonato benzylsilsesquioxane as shown by the following general formula where x=0.65, y=0.05 and z=0.3. Yield: 174 g (90% of theory). GPC data (RI detection): Mw=6,216; Mn=3,636; molecular weight polydisp...

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Abstract

Disclosed are photoimageable compositions containing silsesquioxane binder polymers and photoactive compounds, methods of forming relief images using such compositions and methods of manufacturing electronic devices using such compositions. Such compositions are useful as photoresists and in the manufacture of optoelectronic devices.

Description

BACKGROUND The present invention relates generally to photoimageable compositions. In particular, the present invention relates to photoimageable silsesquioxane compositions. Photoresists are photosensitive films used for transfer of images to a substrate. A coating layer of a photoresist is formed on a substrate and the photoresist layer is then exposed through a photomask to a source of activating radiation. The photomask has areas that are opaque to activating radiation and other areas that are transparent to activating radiation. Exposure to activating radiation provides a photoinduced chemical transformation of the photoresist coating to thereby transfer the pattern of the photomask to the photoresist-coated substrate. Following exposure, the photoresist is developed to provide a relief image that permits selective processing of a substrate. A photoresist can be either positive-acting or negative-acting. For most negative-acting photoresists, those coating layer portions tha...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G03C1/73G03C1/76G03C1/795G03F7/00G03F7/038G03F7/039G03F7/075G03F7/11G03F7/30G03F7/40H01L21/027
CPCG03F7/0005G03F7/001G03F7/0382G03F7/0392Y10S430/115Y10S430/106Y10S430/11Y10S430/108Y10S430/111G03F7/0757G03F7/039
Inventor GRONBECK, DANA A.BARCLAY, GEORGE G.LINEHAN, LEO L.XIONG, KAOKANAGASABAPATHY, SUBBAREDDY
Owner SHIPLEY CO LLC
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