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Photobase generator and photoresist composition containing same

A technology of photoresist and photobase generator, which is applied in photosensitive materials for photomechanical equipment, original parts for photomechanical processing, optics, etc., and can solve problems such as loss of contact holes and pattern collapse

Active Publication Date: 2020-10-16
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a result, the pattern profile will exhibit an undesired T-top shape, pattern collapse and loss of contact holes may occur, and the depth of iso-dense bias and focal edge may be at unacceptable levels

Method used

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  • Photobase generator and photoresist composition containing same
  • Photobase generator and photoresist composition containing same
  • Photobase generator and photoresist composition containing same

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0119] Example 1: Synthesis of NB-DiOC (C)

[0120]

[0121]

[0122] 1,1'-Carbonyldiimidazole (5.3 g; 1.0 eq.) was suspended in anhydrous DMF (60 mL) under nitrogen atmosphere generally as described in Scheme 1 above. The solution was cooled to 0°C and (2-nitrophenyl)methanol (5.0 g; 1.0 eq.) in anhydrous DMF (40 mL) was added slowly. After stirring at RT for 3 hours, dioctylamine (7.88 g; 1.0 eq.) was added. The mixture was stirred at 70°C for 20 hours. The reaction mixture was diluted with EA, washed with water. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude compound of the title compound was purified by flash chromatography (EtOAc / heptane).

example 2

[0123] Example 2: Synthesis of NB-DEHC (E)

[0124]

[0125] Triphosgene (1.16 g; 0.3 eq.) was suspended in anhydrous DCM (30 mL) under a nitrogen atmosphere generally as described above in Scheme 2. The solution was cooled to 0 °C. Then, (2-nitrophenyl)methanol (2.0 g; 1.0 eq.) and N,N-diisopropylethylamine (3.38 g; 2.0 eq.) in dry DCM (30 mL) were added. After stirring at RT for 3 hours, bis(2-ethylhexyl)amine (3.15 g; 1.0 eq.) was added slowly and it was stirred for 4 hours. The reaction mixture was washed with water and the organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude title compound was purified by flash chromatography (EtOAc / heptane).

example 3

[0126] Example 3: Synthesis of ANT-DEHC

[0127]

[0128] Triphosgene (2.137 g; 0.5 eq.) was suspended in anhydrous DCM (30 mL) under a nitrogen atmosphere generally as described in Scheme 3 above. The solution was cooled to 0 °C. Then, 9-(hydroxymethyl)anthracene (3.0 g; 1.0 eq.) and N,N-diisopropylethylamine (3.723 g; 2.0 eq.) in dry DCM (100 mL) were added. After stirring at RT for 3 hours, bis(2-ethylhexyl)amine (3.478 g; 1.0 eq.) was added slowly and it was stirred for 4 hours. The reaction mixture was washed with water and the organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude title compound was purified by flash chromatography (EtOAc / heptane).

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Abstract

wherein X1 is an optionally substituted aromatic group; R1 is a linker; and R2 and R3 are the same or different optionally substituted linear, branched or cyclic aliphatic group or an optionally substituted aromatic group, wherein at least one of R2 and R3 is an optionally substituted branched alkyl group having 4 or more carbon atoms.

Description

Background technique [0001] This invention relates to photobase generators for use in photoresist compositions. The photobase generator contains one or more branched chain alkyl groups that can provide enhanced surface activity. [0002] Photoresists are light-sensitive films used to transfer images to substrates. A coating layer of photoresist is formed on the substrate, and the photoresist layer is then exposed through a photomask to a source of activating radiation. After exposure, the photoresist is developed to provide a relief image that allows selective processing of the substrate. [0003] Considerable effort has been made to extend the practical resolving power of positive-tone resist development, including in immersion lithography. One such example includes negative tone development (NTD) of conventional positive tone chemically amplified photoresists, which leaves exposed areas made of insoluble resulting pattern. See, eg, U.S. 6,790,579. [0004] However, usi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G03F7/004G03F7/038C07C271/12C07C271/14
CPCC07C271/12C07C271/14G03F7/004G03F7/038C07C2603/14G03F7/0045G03F7/0046G03F7/0397G03F7/325C07C271/08G03F1/76G03F7/0382G03F7/0392H01L21/0274G03F7/2041G03F7/322
Inventor M·K·蒋E·H·柳C-Y·洪M·Y·金J-J·李D-J·洪D-Y·金H-J·林J·Y·安O-M·全
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC