Rohm & Haas Electronic Materials LLC

Dupont Electronic Materials International, LLC

Irvinder Kaur

Cong Liu

Mingqi Li

Cheng-Bai Xu

Kevin Rowell

Doris H Kang

Xisen Hou

Emad Aqad

Gerhard Pohlers

Cheng Bai Xu

Deyan Wang

Jong Keun Park

Chunyi Wu

Gregory P Prokopowicz

Ke Yang

Huaxing Zhou

Jibin Sun

Joshua A Kaitz

Cecily Andes

Charlotte Cutler

Colin Liu

Doris Kang

A polymer, comprising a first repeating unit derived from a first monomer comprising a single ester acetal group, and a second repeating unit derived from a second monomer comprising a plurality of ester acetal groups.

Photoresist compositions and pattern formation methods

Photoresist topcoat compositions, comprising: a first polymer that is aqueous base soluble and is present in an amount of from 70 to 99 wt % based on total solids of the composition; a second polymer comprising a repeat unit of general formula (IV) and a repeat unit of general formula (V): wherein: Rindependently represents H, halogen atom, C1-C3 alkyl, or C1-C3 haloalkyl; Rrepresents linear, branched or cyclic C1 to C20 fluoroalkyl; Rrepresents linear, branched or cyclic C1 to C20 fluoroalkyl; Lrepresents a multivalent linking group; and m is an integer of from 1 to 5; wherein the second polymer is free of non-fluorinated side chains; and wherein the second polymer is present in an amount of from 1 to 30 wt % based on total solids of the composition and a solvent. The invention finds particular applicability in the manufacture of semiconductor devices.

Photoresist topcoat compositions and methods of processing photoresist compositions

Photoresist topcoat compositions comprise: a matrix polymer and a surface active polymer, wherein the surface active polymer comprises polymerized units of the following general formula (I): wherein: Rrepresents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, or a C1-C4 haloalkyl group; Rindependently represents a hydrogen atom or an optionally substituted alkyl group, wherein at least one Ris not a hydrogen atom, wherein the Rgroups taken together optionally form a cyclic structure, and wherein the total number of carbon atoms for the Rgroups taken together is from 2 to 20; Rrepresents an optionally substituted C1-C4 alkylene group, wherein an Rgroup optionally forms a cyclic structure with R; and Rindependently represents C1-C4 fluoroalkyl groups; wherein the total polymerized units of general formula (I) are present in the surface active polymer in an amount of 95 wt % or more based on total polymerized units of the surface active polymer; and wherein the surface active polymer is present in the composition in an amount of from 0.1 to 30 wt % based on total solids of the composition; and an organic-based solvent system comprising a plurality of organic solvents. The invention finds particular applicability in the manufacture of semiconductor devices.

Disclosed herein is a copolymer comprising first polymerized units of the formula (1);

Polymers useful as surface leveling agents

A pattern formation method, comprising: (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 overcoat composition over the photoresist pattern, wherein the pattern overcoat composition comprises a second polymer and an organic solvent, wherein the organic solvent comprises one or more ester solvents, wherein the ester solvent is of the formula R&#x2014;C(O)O&#x2014;R, wherein Ris a C3-C6 alkyl group and Ris a C5-C10 alkyl group; (d) baking the coated photoresist pattern; and (e) rinsing the coated photoresist pattern with a rinsing agent to remove the second polymer. The methods find particular applicability in the manufacture of semiconductor devices.

Pattern formation methods and photoresist pattern overcoat compositions

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

Photoresist topcoat compositions, comprising: a first polymer comprising a first repeat unit of general formula (I) and a second repeat unit of general formula (II): wherein: Rindependently represents H, F or optionally fluorinated C1 to C4 alkyl; Rrepresents optionally fluorinated linear, branched or cyclic C1 to C20 alkyl; Lrepresents a single bond or a multivalent linking group; and n is an integer of from 1 to 5; a second polymer comprising a first repeat unit of general formula (III) and a second repeat unit of general formula (IV): wherein: Rindependently represents H, F or optionally fluorinated C1 to C4 alkyl; Rrepresents linear, branched or cyclic C1 to C20 alkyl; Rrepresents linear, branched or cyclic C1 to C20 fluoroalkyl; Lrepresents a single bond or a multivalent linking group; and n is an integer of from 1 to 5; and a solvent. Coated substrates coated with the described topcoat compositions and methods of processing a photoresist composition are also provided. The invention finds particular applicability in the manufacture of semiconductor devices.

Provided are topcoat compositions that include: a matrix polymer; a surface active polymer; an ionic thermal acid generator comprising an anion and a cation, wherein the anion, the cation, or the anion and the cation are fluorinated; and a solvent. Also provided are coated substrates and pattern-forming methods which make use of the topcoat compositions. The invention has particular applicability in photolithographic processes as a photoresist topcoat layer in the manufacture of semiconductor devices.

Topcoat compositions containing fluorinated thermal acid generators

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

Acid generator compounds are provided that are particularly useful as a photoresist composition component. In one preferred aspect, acid generators are provided that comprise one or more hydrophilic moieties.

Growing community of inventors

Northborough, MA, United States of America

Irvinder Kaur