Photoresist topcoat for a photolithographic process
AssigneeInternational Business Machines Corporation
InventorsRobert Allen, Ratnam Sooriyakumaran, Linda Sundberg
Life of this patent
Estimating the term…
Abstract
A composition that includes functionalized polyhedral oligomeric silsesquioxanes derivatives of the formulas TmR3 where m is equal to 8, 10 or 12 and QnMnR1,R2,R3 where n is equal to 8, 10 or 12 are provided. The functional groups include aqueous base soluble moieties. Mixtures of the functionalized polyhedral oligomeric silsesquioxanes derivatives are highly suitable as a topcoat for photoresist in photolithography and immersion photolithography applications.
Claims39
A resin composition, comprising:
- a QnMnR1,R2,R3 resin, wherein Q represents SiO4/2, MR1,R2,R3 represents R1,R2,R3SiO1/2, and n is equal to 8, 10 or 12;
- wherein R1 and R2 are independently selected from the group consisting of hydrogen, a linear alkyl group having 16 carbon atoms, a branched alkyl group having 2-12 carbon atoms, a cycloalkyl group having 3-17 carbon atoms, a fluorinated linear alkyl group having 2-12 carbon atoms, a fluorinated branched alkyl group having 2-12 carbon atoms, a fluorinated cycloalkyl group having 3-17 carbon atoms, a cycloalkyl substituted alkyl group having 4-23 carbon atoms and an alkyl substituted cycloalkyl group having 4-23 carbon atoms;
- wherein R3 is selected from the group consisting of a linear alkyl group having 1-6 carbon atoms, a branched alkyl group having 2-12 carbon atoms, a cycloalkyl group having 3-17 carbon atoms, a fluorinated linear alkyl group having 2-12 carbon atoms, a fluorinated branched alkyl group having 2-12 carbon atoms, a fluorinated cycloalkyl group having 3-17 carbon atoms, a cycloalkyl substituted alkyl group having 4-23 carbon atoms and an alkyl substituted cycloalkyl group having 4-23 carbon atoms;
- and
- wherein R3 includes either (a) a substituent Y1 group and a substituent Y2 group or (b) a substituent Y3 group, wherein Y1 and Y2 are each selected from the group consisting of hydrogen, —COOH, —COOR1—, —SO2OH, —C(CF3)2OH, —NHSO2R, —NHCOR1, wherein Y1 and Y2 cannot both be hydrogen, and wherein Y3 is selected from the group consisting of —CONHCO— and —CONOHCO—, each monovalent bond of said Y3 group bonded to different adjacent carbon atoms of said R3.
A resin composition, comprising:
- a TmR3 resin, wherein T represents R3 SiO3/2, and m is equal to 8, 10 or 12;
- wherein R3 is selected from the group consisting of a linear alkyl group having 1-6 carbon atoms, a branched alkyl group having 2-12 carbon atoms, a cycloalkyl group having 3-17 carbon atoms, a fluorinated linear alkyl group having 2-12 carbon atoms, a fluorinated branched alkyl group having 2-12 carbon atoms, a fluorinated cycloalkyl group having 3-17 carbon atoms, a cycloalkyl substituted alkyl group having 4-23 carbon atoms and an alkyl substituted cycloalkyl group having 4-23 carbon atoms;
- and
- wherein R3 includes either (a) a substituent Y1 group and a substituent Y group or (b) a substituent Y3 group, wherein Y1 and Y2 are each selected from the group consisting of hydrogen, —COOH, —COOR1—, —SO2OH, —C(CF3)2OH, —NHSO2R1, —NHCOR1, wherein Y1 and Y2 cannot both be hydrogen, and wherein Y3 is selected from the group consisting of —CONHCO— and —CONOHCO—, each monovalent bond of said Y3 group bonded to different adjacent carbon atoms of said R3.
A topcoat composition, comprising:
- a mixture of two or more resins, each resin of said mixture of two or more resins comprising different QnMnR1,R2,R3 resins, wherein Q represents SiO4/2, MR1,R2,R3 represents R1,R2,R3SiO1/2, and n is equal to 8, 10 or 12;
- wherein R1 and R2 are independently selected from the group consisting of hydrogen, a linear alkyl group having 1-6 carbon atoms, a branched alkyl group having 2-12 carbon atoms, a cycloalkyl group having 3-17 carbon atoms, a fluorinated linear alkyl group having 2-12 carbon atoms, a fluorinated branched alkyl group having 2-12 carbon atoms, a fluorinated cycloalkyl group having 3-17 carbon atoms, a cycloalkyl substituted alkyl group having 4-23 carbon atoms and an alkyl substituted cycloalkyl group having 4-23 carbon atoms;
- wherein R3 is selected from the group consisting of a linear alkyl group having 1-6 carbon atoms, a branched alkyl group having 2-12 carbon atoms, a cycloalkyl group having 3-17 carbon atoms, a fluorinated linear alkyl group having 2-12 carbon atoms, a fluorinated branched alkyl group having 2-12 carbon atoms, a fluorinated cycloalkyl group having 3-17 carbon atoms, a cycloalkyl substituted alkyl group having 4-23 carbon atoms and an alkyl substituted cycloalkyl group having 4-23 carbon atoms;
- and
- wherein R3 includes either (a) a substituent Y1 group and a substituent Y2 group or (b) a substituent Y3 group, wherein Y1 and Y2 are each selected from the group consisting of hydrogen, —COOH, —COOR1—, —SO2OH, —C(CF3)2OH, —NHSO2R1, —NHCOR1, wherein Y1 and Y2 cannot both be hydrogen, and wherein Y3 is selected from the group consisting of —CONHCO— and —CONOHCO—, each monovalent bond of said Y3 group bonded to different adjacent carbon atoms of said R3;
- and
- a casting solvent selected from the group consisting of a linear monohydroxyl alcohol having 4-10 carbon atoms, a branched chain monohydroxyl alcohol having 4-10 carbon atoms, a cyclic monohydroxyl alcohol having 4-10 carbon atom, a linear dihydroxyl alcohol having 4-10 carbon atoms, a branched chain dihydroxyl alcohol having 4-10 carbon atoms, a cyclic dihydroxyl alcohol having 4-10 carbon atoms, and combinations thereof.
A topcoat composition, comprising:
- a mixture of two or more resins, each resin of said mixture of two or more resins comprising different TmR3 resins, wherein T represents R3SiO3/2, and m is equal to 8, 10 or 12;
- wherein R3 is selected from the group consisting of a linear alkyl group having 1-6 carbon atoms, a branched alkyl group having 2-12 carbon atoms, a cycloalkyl group having 3-17 carbon atoms, a fluorinated linear alkyl group having 2-12 carbon atoms, a fluorinated branched alkyl group having 2-12 carbon atoms, a fluorinated cycloalkyl group having 3-17 carbon atoms, a cycloalkyl substituted alkyl group having 4-23 carbon atoms and an alkyl substituted cycloalkyl group having 4-23 carbon atoms;
- and
- wherein R3 includes either (a) a substituent Y1 group and a substituent Y2 group or (b) a substituent Y3 group, wherein Y1 and Y2 are each selected from the group consisting of hydrogen, —COOH, —COOR1—, —SO2OH, —C(CF3)2OH, —NHSO2R1, —NHCOR1, wherein Y1 and Y2 cannot both be hydrogen, and wherein Y3 is selected from the group consisting of —CONHCO— and —CONOHCO—, each monovalent bond of said Y3 group bonded to different adjacent carbon atoms of said R3;
- and
- a casting solvent selected from the group consisting of linear monohydroxyl alcohols having 4-10 carbon atoms, branched chain monohydroxyl alcohols having 4-10 carbon atoms, cyclic monohydroxyl alcohols having 4-10 carbon atoms, linear dihydroxyl alcohols having 4-10 carbon atoms, branched chain dihydroxyl alcohols having 4-10 carbon atoms, cyclic dihydroxyl alcohols having 4-10 carbon atoms, and combinations thereof.
A topcoat composition, comprising:
- a mixture of two or more different resins, wherein each resin of said mixture of two or more different resins is selected from the group consisting of QnMnR1,R2,R3 resins and TmR3 resins, wherein Q represents SiO4/2, MR1,R2,R3 represents R1,R2,R3SiO1/2, n is equal to 8, 10 or 12, T represents R3SiO3/2, and m is equal to 8, 10 or 12, wherein a first resin of said mixture of two or more different resins is a QnMnR1,R2,R3 resin and a second resin of said mixture of two or more different resins is a TmR3;
- wherein R1 and R2 are independently selected from the group consisting of hydrogen, a linear alkyl group having 1-6 carbon atoms, a branched alkyl group having 2-12 carbon atoms, a cycloalkyl group having 3-17 carbon atoms, a fluorinated linear alkyl group having 2-12 carbon atoms, a fluorinated branched alkyl group having 2-12 carbon atoms, a fluorinated cycloalkyl group having 3-17 carbon atoms, a cycloalkyl substituted alkyl group having 4-23 carbon atoms and an alkyl substituted cycloalkyl group having 4-23 carbon atoms;
- wherein R3 is selected from the group consisting of a linear alkyl group having 1-6 carbon atoms, a branched alkyl group having 2-12 carbon atoms, a cycloalkyl group having 3-17 carbon atoms, a fluorinated linear alkyl group having 2-12 carbon atoms, a fluorinated branched alkyl group having 2-12 carbon atoms, a fluorinated cycloalkyl group having 3-17 carbon atoms, a cycloalkyl substituted alkyl group having 4-23 carbon atoms and an alkyl substituted cycloalkyl group having 4-23 carbon atoms;
- and
- wherein R3 includes either (a) a substituent Y1 group and a substituent Y2 group or (b) a substituent Y3 group, wherein Y1 and Y2 are each selected from the group consisting of hydrogen, —COOH, —COOR1—, —SO2OH, —C(CF3)2OH, —NHSO2R1, —NHCOR1, wherein Y1 and Y2 cannot both be hydrogen, and wherein Y3 is selected from the group consisting of —CONHCO— and —CONOHCO—, each monovalent bond of said Y3 group bonded to different adjacent carbon atoms of said R3;
- and
- a casting solvent selected from the group consisting of a linear monohydroxyl alcohol having 4-10 carbon atoms, a branched chain monohydroxyl alcohol having 4-10 carbon atoms, a cyclic monohydroxyl alcohol having 4-10 carbon atom, a linear dihydroxyl alcohol having 4-10 carbon atoms, a branched chain dihydroxyl alcohol having 4-10 carbon atoms, a cyclic dihydroxyl alcohol having 4-10 carbon atoms, and combinations thereof.
A method of forming an image in a photoresist layer, comprising:
- (a) providing a substrate;
- (b) forming said photoresist layer over said substrate;
- (c) forming a topcoat over said photoresist layer, wherein said topcoat layer includes at least one silicon containing material, includes no polymeric materials, or includes at least one silicon containing material and no polymeric materials;
- (d) exposing said photoresist to radiation through a photomask having opaque and clear regions, said opaque regions blocking said radiation and said clear regions being transparent to said radiation, said radiation changing the chemical composition of regions of said photoresist layer exposed to said radiation forming exposed and unexposed regions in said photoresist layer;
- and
- (e) removing either said exposed regions of said photoresist layer or said unexposed regions of said layer.
Dependencies are inferred from the claim text.