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Acid generators and photoresists comprising same

a technology of acid generators and photoresists, applied in the field of new photoresist compositions, can solve the problems that euv photoresist development remains a challenging issue in euvl technology implementation, and achieve the effects of reducing non-complexed base concentration, faster photospeed, and higher contras

Inactive Publication Date: 2019-07-25
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

These compositions demonstrate improved line width roughness, critical dimension uniformity, and exposure latitude, enabling the creation of submicron features with increased resolution and sensitivity, particularly beneficial for EUV imaging applications.

Problems solved by technology

EUV photoresist development continues to be a challenging issue for EUV Lithography (EUVL) technology implementation.

Method used

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  • Acid generators and photoresists comprising same
  • Acid generators and photoresists comprising same
  • Acid generators and photoresists comprising same

Examples

Experimental program
Comparison scheme
Effect test

example 1

on of Camphorsulfonate Silver Salt

[0084]

[0085]Silver oxide (2.74 g, 11.8 mmol) was added to a solution of camphorsulfonic acid (5.00 g, 21.5 mmol), in acetonitrile (50 mL), stirred at r.t. overnight, filtered and concentrated to afford the title compound (7.00 g, 95%) as a white solid. 1H NMR (300 MHz, (CD3)2SO) δ: 2.94 (d, J=14.6 Hz, 1H), 2.60-2.72 (m, 1H), 2.43 (d, J=14.6 Hz, 1H), 2.25 (dt, J=14.6, 3.6 Hz, 1H), 1.96 (t, J=4.5 Hz, 1H), 1.76-1.91 (m, 2H), 1.25-1.37 (m, 2H), 1.06 (s, 3H), 0.76 (s, 3H).

example 2

on of 3-Hydroxyadamantanecarboxylic Acid Silver Salt

[0086]

Silver oxide (5.79 g, 49.8 mmol) was added to a solution of 3-hydroxyadamantanecarboxylic acid (10.0 g, 51 mmol) in acetone (250 mL) and water (250 mL) and stirred at r.t. overnight. The precipitate was filtered, washed with 1:1 acetone:water (3×250 mL), MTBE (3×200 mL) and dried to afford the title compound (13.2 g, 86%) as an off white sold. 1H NMR (300 MHz, (CD3)2SO) δ: 4.36 (s, 1H), 2.50-2.54 (m, 2H), 1.20-1.78 (m, 12H).

example 3

on of 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium camphorsulfonate

[0087]

Camphorsulfonate silver salt (2.84 g, 8.34 mmol) in methanol (50 mL) and water (5 mL) was added to a solution of 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide in methanol (100 mL) and stirred at r.t. overnight. The reaction mixture was filtered, concentrated, diluted with dichloromethane (200 mL) and washed with water (3×200 mL) and concentrated to afford the title compound (4.4 g, 76%) as a white solid. 1H NMR (300 MHz, (CD3)2C0) δ: 8.87-8.55 (m, 4H), 7.96 (dt, J=7.5, 0.5 Hz, 2H), 7.74 (dt, J=7.5, 0.5 Hz, 2H), 7.59 (s, 2H), 4.53 (s, 2H), 3.13 (d, J=15.5 Hz, 1H), 3.00.3.09 (m, 1H), 2.61 (d, J=15 Hz, 1H), 2.28 (s, 6), 1.90-2.12 (m, 7H), 1.76 (d, J=15 Hz, 1H), 1.55-1.72 (m, 6H), 1.35-1.43 (m, 1H), 1.23-1.33 (m, 1H), 1.22 (s, 3H), 1.12 (s, 3H), 0.84 (t, J=7.5 Hz, 3H).

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Abstract

Acid generator compounds are provided that are particularly useful as a photoresist composition component. In one preferred aspect, photoresists are provided that comprise (i) a polymer; (ii) a first onium salt acid generator that produces a first acid upon exposure of the photoresist composition to activating radiation; and (iii) a second onium salt acid generator that 1) comprises a covalently bound acid-labile moiety and 2) produces a second acid upon exposure of the photoresist composition to activating radiation, wherein the first acid and second acid have pKa values that differ by at least 0.5.

Description

1. FIELD[0001]In one aspect, the present invention relates to new photoresist compositions that comprise a first onium salt acid generator; a second onium salt acid generator that comprises a covalently bound acid-labile moiety, and wherein the first and second onium salts upon exposure to activating radiation produce acids that have differing pKa values.2. INTRODUCTION[0002]Photoresists are photosensitive films for transfer of images to a substrate. They form negative or positive images. After coating a photoresist on a substrate, the coating is exposed through a patterned photomask to a source of activating energy such as ultraviolet light to form a latent image in the photoresist coating. The photomask has areas opaque and transparent to activating radiation that define an image desired to be transferred to the underlying substrate. A relief image is provided by development of the latent image pattern in the resist coating.[0003]Known photoresists can provide features having reso...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G03F7/004G03F7/039G03F7/038
CPCG03F7/0045G03F7/0397G03F7/0046G03F7/0382G03F7/0392G03F7/004G03F7/029G03F7/26H01L21/027
Inventor THACKERAY, JAMES W.LABEAUME, PAUL J.CAMERON, JAMES F.
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC