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Fluoroalcohol containing molecular photoresist materials and processes of use

A photoresist and molecular glass technology, applied in the field of molecular glass photoresist, can solve the problems of high dissolution rate and incompatibility

Inactive Publication Date: 2013-08-21
IBM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another issue is that due to its high dissolution rate, several MG systems require dilute developer and are therefore incompatible with the traditional developer 0.26N Tetramethylammonium Hydroxide (TMAH)

Method used

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  • Fluoroalcohol containing molecular photoresist materials and processes of use
  • Fluoroalcohol containing molecular photoresist materials and processes of use
  • Fluoroalcohol containing molecular photoresist materials and processes of use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Example 1: In this example, 4-(1,1,1,3,3,3-hexafluoro- 2-Hydroxy-2-propyl)phenylresorcinolcalix[4]arene (structure 1 shown below).

[0086] Structure 1

[0087]

[0088] 4-(1,1,1,3,3,3-hexafluoro-2-hydroxyl-2-propyl)benzaldehyde (5 g, 0.018 mol), resorcinol (2 g, 0.018 mol) and Methanol (20 mL) was placed in a round bottom flask equipped with a stirrer. At room temperature, 5 ml of concentrated hydrochloric acid was added to the mixture, after which the reaction mixture was refluxed at 70°C for 18 hours. Completion of the reaction is determined by the disappearance of the carbonyl absorption peak of the aldehyde starting material using NMR or IR spectroscopy. The reaction solvent, methanol, was evaporated using a rotary evaporator, and the resulting material was precipitated several times with deionized water, and the product was identified by NMR spectroscopy in a yield of 4.5 g (68%). 1H-NMR (DMSO-d6): (ppm) 5.62 (s, CH, 4H), 6.16 (s, ArH, 4H), 6.21 (broad s, A...

Embodiment 2

[0089]Example 2: In this example, the 4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)phenylresorcinolcalix[4 ]arenes were selectively functionalized with tert-butoxycarbonyl (t-BOC) at the phenolic hydroxyl unit by a base-catalyzed reaction to generate 4-(1,1,1,3,3,3-hexafluoro -2-Hydroxy-2-propyl)phenylresorcinolcalix[4]arene (structure 2 shown below).

[0090] Structure 2

[0091]

[0092] 4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)phenylresorcinolcalix[4]arene (2 g, 0.0014 mol) and 4-bis Methylaminopyridine (0.06 g, 0.0005 mol) was dissolved in 25 mL of acetone in a round bottom flask equipped with a stirrer. Di-tert-butyl dicarbonate (2.39 g, 0.011 mol) was added slowly using a dropping funnel, followed by steady stirring. CO released immediately 2 Gas indicated the progress of the reaction, and the reaction mixture was stirred at room temperature for 8 hours. The solvent was reduced by evaporation, and the product was purified by column chromatography using aceton...

Embodiment 3

[0093] Example 3: In this example, the t-BOC-protected 4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)benzene comprising Example 2 Lithographic evaluation of photoresist compositions based on resorcinol calix[4]arene. The photoresist was prepared as 0.25 g of t-BOC-protected 4-(1,1,1,3,3,3-hexafluoro-2-hydroxyl in 5 g of propylene glycol monomethyl ether acetate (PGMEA) -2-propyl)phenylresorcinolcalix[4]arene (structure 2), 25 mg of triphenylthioperfluoro-1-butanesulfonate (photoacid generator), and 0.75 mg of organic Alkaline preparation. The solution was filtered through a 0.2 micron syringe filter.

[0094] The photoresist composition was spin-coated on a blank silicon wafer, and then baked at a temperature of 90° C. for 60 seconds to form a thickness of about 500 angstroms (50 nm). figure 1 The comparative curve at 248 nm in 0.26N TMAH developer is graphically illustrated as a function of 30 second post exposure bake temperature generated using an ASML stepper. As shown,...

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PUM

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Abstract

Phenolic molecular glasses such as calixarenes include at least one fluoroalcohol containing unit. The fluoroalcohol containing molecular glasses can be used in photoresist compositions. Also disclosed are processes for generating a resist image on a substrate using the photoresist composition.

Description

field of invention [0001] The present invention relates to molecular glass photoresists. Background of the invention [0002] As the minimum critical dimension continues to shrink below 50nm, the difficulty of simultaneously meeting critical performance criteria, sensitivity, resolution, and line edge roughness (LER) increases. The size of the polymer used in chemically amplified photoresists in general starts to affect performance at these sizes. For example, it is believed that the magnitude of the line edge roughness is directly related to the molecular weight of the basic polymer in the photoresist, therefore, some photoresists based on low molecular weight polymers or non-polymers have been proposed to address performance issues required by these advanced design rules. [0003] Molecular glass resists have attracted attention as potential candidates for next-generation resist materials. Despite their modest size, such small molecules, known as "molecular glasses" (MG...

Claims

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Application Information

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IPC IPC(8): C07C39/367G03F7/004G03F7/038G03F7/039
CPCC07C39/42C07C69/96C07C2603/92G03F7/0046G03F7/0382G03F7/0392G03F7/004G03F7/038G03F7/0381
Inventor E·A·德希尔瓦L·K·桑德伯格R·苏里亚库马兰G·布雷塔L·D·玻加诺W·辛斯伯格
Owner IBM CORP
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