Rohm & Haas Electronic Materials LLC

Kevin Rowell

Cong Liu

Irvinder Kaur

Cheng-Bai Xu

Mingqi Li

Gerhard Pohlers

Xisen Hou

Cheng Bai Xu

Jong Keun Park

Shintaro Yamada

Seung-Hyun Lee

Thomas A Estelle

Wenyan Yin

Colin Liu

Photoresist pattern trimming compositions comprise a polymer, an aromatic sulfonic acid, and an organic-based solvent system, wherein the aromatic sulfonic acid is of general formula (I): wherein: Arrepresents an aromatic group; Rindependently represents a halogen atom, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted carbocyclic aryl, substituted or unsubstituted heterocyclic aryl, substituted or unsubstituted alkoxy, or a combination thereof, wherein adjacent Rgroups together optionally form a fused ring structure with Ar; a represents an integer of 2 or more; and b represents an integer of 1 or more, provided that a+b is at least 3 and is not greater than the total number of available aromatic carbon atoms of Ar, and two or more of Rare independently a fluorine atom or a fluoroalkyl group bonded directly to an aromatic ring carbon atom.

Photoresist pattern trimming compositions and pattern formation methods

Photoresist pattern trimming compositions comprise a polymer, an aromatic sulfonic acid, and an organic-based solvent system, wherein the polymer comprises polymerized units of general formulas (I) and (II): wherein: X independently represents a halogen atom; Q represents a single bond, &#x2014;O&#x2014;, or &#x2014;C(O)O&#x2014;; Rindependently represents hydrogen, a halogen atom, C1-C12 alkyl or C1-C12 fluoroalkyl; Rrepresents C1-C3 alkyl or C1-C3 fluoroalkyl; and m is an integer from 0 to 4; and wherein the polymerized units of general formula (I) are present in the polymer in an amount of 10 to 90 mol % and the polymerized units of general formula (II) are present in the polymer in an amount from 10 to 60 mol %, based on total polymerized units of the polymer. The photoresist pattern trimming compositions and their use in pattern formation methods find particular applicability in the manufacture of semiconductor devices.

Pattern-formation methods comprise: (a) providing a substrate; (b) forming a photoresist pattern over the substrate; (c) applying a pattern treatment composition to the photoresist pattern, the pattern treatment composition comprising a solvent mixture comprising a first organic solvent and a second organic solvent, wherein the first organic solvent has a boiling point that is greater than a boiling point of the second organic solvent, and wherein the first organic solvent has a boiling point of 210&#xb0; C. or more; and (d) thereafter heating the photoresist pattern. The methods find particular applicability in the manufacture of semiconductor devices.

Pattern-formation methods

Provided are ionic thermal acid generators of the following general formula (I): wherein: Arrepresents an optionally substituted carbocyclic or heterocyclic aromatic group; W independently represents a group chosen from carboxyl, hydroxy, nitro, cyano, C1-5 alkoxy and formyl; X is a cation; Y independently represents a linking group; Z independently represents a group chosen from hydroxyl, fluorinated alcohols, esters, optionally substituted alkyl, C5 or higher optionally substituted monocyclic, polycyclic, fused polycyclic cycloaliphatic, or aryl, which may optionally comprise a heteroatom, provided at least one occurrence of Z is a hydroxyl group; a is an integer of 0 or greater; b is an integer of 1 or greater; provided that a+b is at least 1 and not greater than the total number of available aromatic carbon atoms of the aromatic group. Also provided are photoresist pattern trimming compositions and methods of trimming a photoresist pattern using the trimming compositions. The thermal acid generators, compositions and methods find particular applicability in the manufacture of semiconductor devices.

Thermal acid generators and photoresist pattern trimming compositions and methods

Provided are methods of trimming a photoresist pattern. The methods comprise: (a) providing a semiconductor substrate; (b) forming a photoresist pattern on the substrate, wherein the photoresist pattern is formed from a chemically amplified photoresist composition comprising: a matrix polymer comprising an acid labile group; a photoacid generator; and a solvent; (c) coating a photoresist trimming composition on the substrate over the photoresist pattern, wherein the trimming composition comprises: a matrix polymer, an aromatic acid that is free of fluorine; and a solvent; (d) heating the coated substrate, thereby causing a change in polarity of the photoresist matrix polymer in a surface region of the photoresist pattern; and (e) contacting the photoresist pattern with a rinsing agent to remove the surface region of the photoresist pattern, thereby forming a trimmed photoresist pattern. The methods find particular applicability in the manufacture of semiconductor devices.

Photoresist pattern trimming methods

Provided are ionic thermal acid generators comprising an anion of an aromatic sulfonic acid comprising one or more fluorinated alcohol group and a cation. Also provided are photoresist pattern trimming compositions that include an ionic thermal acid generator, a matrix polymer and a solvent, and methods of trimming a photoresist pattern using the trimming compositions. The thermal acid generators, compositions and methods find particular applicability in the manufacture of semiconductor devices.

Methods of trimming a photoresist pattern comprise: (a) providing a semiconductor substrate; (b) forming a photoresist pattern over the semiconductor substrate, wherein the photoresist pattern is formed from a photoresist composition comprising: a first polymer comprising acid labile groups; and a photoacid generator; (c) coating a pattern trimming composition over the photoresist pattern, wherein the pattern trimming composition comprises a second polymer and a solvent system, wherein the solvent system comprises one or more monoether solvents in a combined amount of 50 wt % or more based on the solvent system; (d) heating the coated semiconductor substrate, thereby causing a change in solubility of a surface region of the photoresist pattern in a rinsing agent to be applied; and (e) contacting the photoresist pattern with a rinsing agent to remove the surface region of the photoresist pattern, thereby forming a trimmed photoresist pattern. The methods find particular applicability in the manufacture of semiconductor devices.

Pattern trimming methods

Photoresist pattern trimming compositions comprise: a polymer that is soluble in a 0.26 normality aqueous tetramethylammonium hydroxide solution; and a solvent system, wherein the solvent system comprises one or more monoether solvents in a combined amount of from 50 to 98 wt % based on the solvent system. The compositions find particular applicability in the manufacture of semiconductor devices.

Pattern trimming compositions and methods

Photoresist pattern trimming compositions are provided. The compositions comprise: a matrix polymer, an aromatic sulfonic acid and a solvent, wherein the aromatic sulfonic acid comprises one or more fluorinated alcohol group. Also provided are methods of trimming a photoresist pattern using the trimming compositions. The compositions and methods find particular applicability in the manufacture of semiconductor devices.

Photoresist pattern trimming compositions and methods

New ionic thermal acid generator compounds are provided. Also provided are photoresist compositions, antireflective coating compositions, and chemical trim overcoat compositions, and methods of using the compositions.

Ionic thermal acid generators for low temperature applications

Provided are compositions and methods for trimming a photoresist pattern. The photoresist pattern trimming composition comprises: a matrix polymer comprising a unit formed from a monomer of the following general formula (I): wherein: Ris chosen from hydrogen, fluorine, C-Calkyl and C-Cfluoroalkyl; Ris chosen from C-Calkylene; and Ris chosen from C-Cfluoroalkyl; an aromatic acid that is free of fluorine; and a solvent. The compositions and methods find particular applicability in the manufacture of semiconductor devices.

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Brighton, MA, United States of America

Kevin Rowell