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US 7,022,457 B2Granted
Photoresists with hydroxylated, photoacid-cleavable groups
AssigneeE. I. Du Pont de Nemours and Company
InventorsWilliam Brown Farnham, Andrew Edward Feiring, Frank Leonard Schadt, III, Weiming Qiu
Life of this patent
Estimating the term…
Abstract
The present invention pertains to photoimaging and the use of photoresists (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The present invention also pertains to novel hydroxy ester-containing polymer compositions that are useful as base resins in resists and potentially in many other applications.
Claims29
A photoresist comprising
- a.) a polymer functionalized with at least one hydroxy ester functional group of the formula:
- —CO2—C(Me)2-C(Me)2-OH
- and
- b.) a photoactive component.
1 more element
A photoresist comprising
- a.) a polymer comprising at least one repeat unit derived from
- H2C═C(X)—CO2—C(Me)2-C(Me)2-OH
- wherein X=H, C1–C6 alkyl, F, or F-substituted C1–C6 alkyl;
- and
- b.) a photoactive component.
2 more elements
A copolymer comprising
- a.) a repeat unit containing at least one hydroxy ester functional group of the formula:
- —CO2—C(R1)(R2)—[C(R3)(R4)]n—C(R5)(R6)—OH,
- wherein
- n=0, 1, 2, 3,4 or 5;
- R1, R2=C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R1 and R2 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- R3, R4=H, C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R3 and R4 taken together fonn a 3- to 8-inembered ring, optionally substituted with an ether oxygen;
- R5, R6=H, C1–C6 alkyl, or C1–C6 alkyl substituted wit an ether oxygen;
- or R5 and R6 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- or R1 and R5 taken together with —[C(R3)(R4)]n—form a 4- to 8-membered ring, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- b.) a repeat unit derived from a polycyclic ethylenically unsaturated compound;
- and
- c.) a repeat unit derived from an ethylenically unsaturated compound selected from the group consisting of tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride, perfluoro-(2,2-dimethyl-1,3-dioxole), perfluoro-(2-methylene-4-methyl-1,3-dioxolane, CF2═CFO(CF2)tCF═CF2, where t is 1 or 2, and Rf′OCF═CF2, wherein Rf′ is a saturated fluoroalkyl group of from 1 to about 10 carbon atoms.
11 more elements
A photoresist comprising
- a.) a polymer comprising
- i) a repeat unit fimetionalized with at least one hydroxy ester functional group of the formula:
- —CO2—C(R1)(R2)—[C(R3)(R4)]n—C(R5)(R6)—OH,
- wherein
- n=0, 1, 2, 3, 4 or 5;
- R1, R2 =C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R1 and R2 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- R3, R4=H, C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R3 and R4 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- R5, R6 =H, C1–C6 aIkyl, or C1–C6 alkyl substituted with an ether oxygen;
- or R5 and R6 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- or R1 and R5 taken together with —[C(R3)(R4)]n— form a 4- to 8-membered ring, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- ii.) a repeat unit derived front at least one polycyclic ethylenically unsaturated compound;
- and
- iii.) a repeat unit derived from at least one ethylenically unsaturated compound selected from the group consisting of tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride, perfluoro-(2,2-dimethyl-1,3-dioxole), perfluoro-(2-methylene-4-methyl-1,3-dioxolane, CF2═CFO(CF2)tCF═CF2, where t is 1 or 2, and Rf′OCF═CF2, wherein Rf′ is a saturated fluoroalkyl group of from 1 to about 10 carbon atoms;
- and
- b.) a photoactive component
14 more elements
A copolymner comprising
- a.) a first repeat unit containing at least one hydroxy ester functional aroup of the formula:
- —CO2—C(R1)(R2)—[C(R3)(R4)]n—C(R5)(R6)—OH,
- wherein
- n=0, 1, 2, 3, 4 or 5;
- R1, R2=C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R1 and R2 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- R3, R4=H, C1–C6 alkyl, C1–C6 alykl substituted with an ether oxygen;
- or R3 and R4 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- R5, R6=H, C1–C6 alkyl, or C1–C6 alkyl substituted with an ether oxygen;
- or R5 and R6 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- or
- R1 and R5 taken together with —[C(R3)(R4)]n— form a 4- to 8-membered ring, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- b.) a second repeat unit derived from a polycyclic ethylenically unsaturated compound wherein the ethylenically unsaturated groups contained within the polycyclic moiety;
- and
- c.) a third repeat unit derived from an ethylenically unsaturated compound which contains at least one fluorine atom covalently attached to an ethylenically unsaturated carbon atom.
12 more elements
A photoresist comprising
- a.) a polymer comprising
- i) a first repeat unit functionalized with at least one hydroxy ester functional group of the formula:
- —CO2—C(R1)(R2)—[C(R3)(R4)]n—C(R5)(R6)—OH,
- wherein
- n=0, 1, 2, 3, 4 or 5;
- R1, R2=C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R1 and R2 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- R3, R4=H, C1–C6 alky, C1–C6 alkyl substituted with an ether oxygen;
- or R3 and R4 taken together form a 3- to 8-membered membered ring, optionally substituted with an ether oxygen;
- R5, R6=H, C1–C6 alkyl, or C1–C6 alkyl substituted with an ether oxygen;
- or R5 and R6 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- or R1 and R5 taken together with —[C(R3)(R4)]n— form a 4-to 8-membered ring, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- ii.) a second repeat unit derived from at least one polycyclic ethylenically unsaturated compound wherein the ethylenically unsaturated group is contained within the polycyclic moiety;
- and
- iii.) a third repeat unit derived from at least one ethylenically unsaturated compound which contains at least one fluorine atom covalently attached to an ethylenically unsaturated carbon atom;
- and
- b.) a photoactive component.
14 more elements
A photoresist comprising
- a.) a polymer comprising:
- 1. at least one hydroxy ester functional group of the formula:
- —CO2—C(R1)(R2)—[C(R3)(R4)]n—C(R5)(R6)—OH,
- wherein
- n=0, 1, 2, 3, 4 or 5;
- R1, R2=C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R1 and R2 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- R3, R4=H, C1–C6 alky, C1–C6 alkyl substituted with an ether oxygen;
- or R3 and R4 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- R5, R6=H, C1–C6 alkyl, or C1–C6 alkyl substituted with an ether oxygen;
- or R5 and R6 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- or R1 and R5 taken together with —[C(R3)(R4)]n form a 4- to 8-membered ring, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- 2.) a repeat unit derived from NB-F-OH;
- and
- b.) a photoactive component.
12 more elements
A photoresist comprising
- a.) a polymer comprising at least one repeat unit derived from
- H2C═C(X)—CO2—C(R1)(R2)—[C(R3)(R4)]n—C(R5)(R6)—OH
- wherein
- X=H, C1–C6 alkyl, F, or F-substituted C1–C6 alkyl;
- n=0, 1, 2, 3, 4 or 5;
- R1, R2=C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R1 and R2 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- R3, R4=H, C1–C6 alky, C1–C6 alkyl substituted with an ether oxygen;
- or R3 and R4 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- R5, R6=H, C1–C6 alkyl, or C1–C6 alkyl substituted with an ether oxygen;
- or R5 and R6 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- or R1 and R5 taken together with —[C(R3)(R4)]n— form a 4- to 8-membered ring, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- b.) a repeat unit derived from NB-F-OH;
- and
- c.) a photoactive component.
12 more elements
A copolymer comprising
- a.) a repeat unit containing at least one hydroxy ester functional group of the formula:
- —CO2—C(R1)(R2)—[C(R3)(R4)]n—C(R5)(R6)—OH,
- wherein
- n=0, 1, 2, 3, 4 or 5;
- R1, R2=C1–C6 alkyl, C1–C6 alkyl substituted with an ether oxygen;
- or R1 and R2 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- R3, R4=H, C1–C6 alky, C1–C6 alkyl substituted with an ether oxygen;
- or R3 and R4 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen,
- R5, R6=H, C1–C6 alkyl, or C1–C6 alkyl substituted with an ether oxygen;
- or R5 and R6 taken together form a 3- to 8-membered ring, optionally substituted with an ether oxygen;
- or R1 and R5 taken together with —[C(R3)(R4)]n— form a 4- to 8-membered ring, provided that the carbon attached to R1 and R2 is not at a bridgehead position;
- b.) a repeat unit derived from a polycyclic ethylenically unsaturated compound which is selected from the group consisting of
- and
- c.) a repeat unit derived from an ethylenically unsaturated compound, which contains at least one fluorine atom covalently attached to an ethylenically unsaturated carbon atom.
11 more elements
A process for preparing a photoresist image on a substrate comprising, in order:
- (W) coating a substrate with a photoresist composition, wherein the photoresist composition comprises:
- a.) a polymer functionalized with at least one hydroxy ester functional group of the formula:
- —CO2—C(Me)2-(Me)2-OH,
- b.) at least one photoactive component;
- and
- c.) a solvent;
- (X) drying the coated photoresist composition to substantially remove the solvent and thereby to form a photoresist layer on the substrate;
- (Y) imagewise exposing the photoresist layer to form imaged and non-imaged areas;
- and
- (Z) developing the exposed photoresist layer having imaged and non-imaged areas to form the relief image on the substrate.
7 more elements
Dependencies are inferred from the claim text.