Photodecomposable bases and photoresist compositions

{
  "publication_number": "US8614047B2",
  "country": "US",
  "kind": "B2",
  "title": "Photodecomposable bases and photoresist compositions",
  "abstract": "Provided are novel symmetrical and asymmetrical bifunctional photodecomposable bases (PDBs) with dicarboxylate anion groups that show increased imaging performance. Also provided are photoresist compositions prepared with the bifunctional dicarboxylated PDBs and lithography methods that use the photoresist compositions of the present invention.",
  "claims": [
    "1. A composition comprising at least one dicarboxylate anion photodecomposable base (PDB), a resist polymer, and pinane acetate p-toluenesulfonate as an acid amplifier, wherein the PDB is fluorinated and/or asymmetrical.",
    "2. The composition of claim 1, wherein the at least one PDB comprises bis(triphenylsulfonium) tetrafluorodiglycolic acid (BisTPS TFDGA).",
    "3. The composition of claim 1, wherein the at least one PDB comprises bis(triphenylsulfonium) 2-ketoglutaricacid (BisTPS 2KGA).",
    "4. The composition of claim 1, wherein the at least one PDB is fluorinated and has at least one structure selected from the group consisting of Structures 1, 2, and 5:",
    "5. The composition of claim 1, wherein the at least one PDB is asymmetrical and has at least one structure selected from the group consisting of Structures 7-10:",
    "6. The composition of claim 1, wherein the resist polymer is selected from the group consisting of poly(p-hydroxystyrene)-methyl adamantyl methacrylate (PHS MAdMA) and poly(p-hydroxystyrene)-2-ethyl-2-adamantyl methacrylate (PHS EAdMA).",
    "7. The composition of claim 1, further comprising a photoacid generator (PAG).",
    "8. The composition of claim 7, wherein the PAG is selected from the group consisting of sulfonium salts, halonium salts, α,α′-bis-sulfonyl-diazomethanes, trifluoromethanesulfonate esters of imides, trifluoromethanesulfonate esters of hydroxyimides, nitrobenzyl sulfonate esters, sulfonyloxynaphthalimides, pyrogallol derivatives, alkyl disulfones, s-triazine derivatives, and sulfonic acid generators.",
    "9. The composition of claim 8, wherein the PAG is the sulfonium salt triphenylsulfonium perfluorobutanesulfonate.",
    "10. A method of patterning a substrate comprising the steps of: (a) applying, over a substrate, a photoresist comprising the composition of claim 1, and a photoacid generator (PAG); (b) post-application baking of the photoresist; (c) exposing the photoresist to radiation; (d) post-exposure baking of the photoresist; and (e) developing the exposed resist with an aqueous base solution.",
    "11. The method of claim 10, wherein the substrate is selected from the group consisting of a metal conductor layer, a ceramic insulator layer, and a semiconductor wafer.",
    "12. The method of claim 10, wherein the photoresist is exposed with radiation selected from the group consisting of DUV optical radiation, ion-beam projection, x-ray radiation, electron beam (e-beam) radiation, focused beam radiation, and EUV radiation.",
    "13. A composition comprising: at least one dicarboxylate anion photodecomposable base (PDB) having at least one structure selected from the group consisting of Structures 3, 4, and 6: a resist polymer; and pinane acetate p-toluenesulfonate as an acid amplifier.",
    "14. The composition of claim 13, wherein the resist polymer is selected from the group consisting of poly(p-hydroxystyrene)-methyl adamantyl methacrylate (PHS MAdMA) and poly(p-hydroxystyrene)-2-ethyl-2-adamantyl methacrylate (PHS EAdMA).",
    "15. The composition of claim 13, further comprising a photoacid generator (PAG).",
    "16. The composition of claim 15, wherein the PAG is selected from the group consisting of sulfonium salts, halonium salts, α,α′-bis-sulfonyl-diazomethanes, trifluoromethanesulfonate esters of imides, trifluoromethanesulfonate esters of hydroxyimides, nitrobenzyl sulfonate esters, sulfonyloxynaphthalimides, pyrogallol derivatives, alkyl disulfones, s-triazine derivatives; and sulfonic acid generators.",
    "17. The composition of claim 16, wherein the PAG is the sulfonium salt triphenylsulfonium perfluorobutanesulfonate.",
    "18. A method of patterning a substrate comprising the steps of: (a) applying, over a substrate, a photoresist comprising the composition of claim 13, and a photoacid generator; (b) post-application baking of the photoresist; (c) exposing the photoresist to radiation; (d) post-exposure baking of the photoresist; and (e) developing the exposed resist with an aqueous base solution.",
    "19. The method of claim 18, wherein the substrate is selected from the group consisting of a metal conductor layer, a ceramic insulator layer, and a semiconductor wafer.",
    "20. The method of claim 18, wherein the photoresist is exposed with radiation selected from the group consisting of DUV optical radiation, ion-beam projection, x-ray radiation, electron beam (e-beam) radiation, focused beam radiation, and EUV radiation.",
    "21. A composition comprising at least one dicarboxylate anion photodecomposable base (PDB) comprising bis(triphenylsulfonium) tetrafluorodiglycolic acid (BisTPS TFDGA).",
    "22. The composition of claim 21, further comprising a resist polymer.",
    "23. The composition of claim 22, wherein the resist polymer is selected from the group consisting of poly(p-hydroxystyrene)-methyl adamantyl methacrylate (PHS MAdMA) and poly(p-hydroxystyrene)-2-ethyl-2-adamantyl methacrylate (PHS EAdMA).",
    "24. The composition of claim 22, further comprising a photoacid generator (PAG).",
    "25. The composition of claim 24, wherein the PAG is selected from the group consisting of sulfonium salts, halonium salts, α,α′-bis-sulfonyl-diazomethanes, trifluoromethanesulfonate esters of imides, trifluoromethanesulfonate esters of hydroxyimides, nitrobenzyl sulfonate esters, sulfonyloxynaphthalimides, pyrogallol derivatives, alkyl disulfones, s-triazine derivatives, and sulfonic acid generators.",
    "26. The composition of claim 25, wherein the PAG is the sulfonium salt triphenylsulfonium perfluorobutanesulfonate.",
    "27. The composition of claim 22, further comprising an acid amplifier.",
    "28. The composition of claim 27, wherein the acid amplifier is pinane acetate p-toluenesulfonate.",
    "29. A composition comprising at least one dicarboxylate anion photodecomposable base (PDB), wherein the PDB has a structure selected from the group consisting of Structures (1), (4)-(7), (9) and (10):."
  ],
  "cpc": [
    "C07C 55/08",
    "C07C 229/24",
    "C07C 55/12",
    "C07C 55/14",
    "C07C 55/32",
    "C07C 59/21",
    "C07C 59/245",
    "C07C 59/295",
    "C07C 59/315",
    "C07C 59/347",
    "C07D 241/04",
    "G03F 7/0045",
    "G03F 7/0046",
    "G03F 7/0397"
  ],
  "assignees": [
    "AYOTHI RAMAKRISHNAN",
    "HINSBERG WILLIAM D",
    "SWANSON SALLY A",
    "WALLRAFF GREGORY M",
    "IBM",
    "JSR CORP"
  ],
  "filing_date": "2011-08-26",
  "publication_date": "2013-12-24",
  "grant_date": "2013-12-24",
  "priority_date": "2011-08-26",
  "application_number": "US-201113219599-A",
  "family_id": "47744208",
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}