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US 2014/0193752 A1Published application
Stabilized acid amplifiers
AssigneeThe Research Foundation of State University of New York
InventorsRobert L. Brainard, Brian Cardineau
Life of this patent
Estimating the term…
Abstract
There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography. Other embodiments are also disclosed.
Claims28
A compound of formula I
- wherein
- G1 is selected from —N+(CH3)3, —(CH2)—N+(CH3)3, —(CH2)—NO2, —CH2(CN), —CH(CN)2, —(CH2)0-1SO2(C1-C8)hydrocarbon, —C6F5, —Si(CH3)3, halogen, —CiHj(halogen)k, and CsHt(halogen)u-E, wherein i is 1-2, j is 0-3, k is 1-5, and the sum of j plus k is 2i+1;
- and wherein s is 1-2, t is 0-2, u is 1-4, and the sum of t plus u is 2s;
- E is selected from —(C1-C6)alkyl, aryl, (C1-C6)haloalkyl, haloaryl, haloaryl(C1-C2)alkyl, and aryl(Ct—C2)alkyl;
- G2 is selected from hydrogen, —CF3, —N+(CH3)3, halogen and (C1-C10)hydrocarbon;
- A is selected from the following moieties:
- wherein
- M is —O—, —S— or —NR90—;
- R10 is chosen from (C1-C8)saturated hydrocarbon;
- (C1-C8)saturated hydrocarbon substituted with halogen, cyano or nitro;
- (C1-C8)silaalkane;
- —O—(C1-C8)saturated hydrocarbon;
- —O—(C1-C8)saturated hydrocarbon substituted with halogen, cyano or nitro;
- —S—(C1-C8)saturated hydrocarbon;
- —S—(C1-C8)saturated hydrocarbon substituted with halogen, cyano or nitro;
- and optionally substituted phenyl;
- R20 is chosen from H, (C1-C6) hydrocarbon and (C1-C6) hydrocarbon substituted with nitro or cyano, or taken together with the carbon to which they are attached, R10 and R20 form a three- to eight-membered ring;
- R40 is chosen from H, (C1-C6)alkyl, —C(═O)(C1-C6)alkyl, —C(═O)(C1-C6)alkenyl, —C(═O)(C1-C6)haloalkyl, benzyl, substituted benzyl, —C(═O)phenyl, —C(═O)substituted phenyl, —SO2-phenyl, —SO2(substituted)phenyl and Q;
- or, when M is O or S, R10 and R40 together with the carbons to which they are attached form a four- to eight-membered ring optionally substituted with one or more (C1-C6) hydrocarbon groups;
- R50 is chosen from H, (C1-C6) hydrocarbon, nitro, cyano, (C1-C6) hydrocarbon substituted with nitro or cyano, and (C1-C6)silaalkane, or together with the carbons to which they are attached, R10 and R50 form a (C3-C8) hydrocarbon ring;
- or, when M is O or S, R20 and R50 together with the carbons to which they are attached form a three- to eight-membered ring optionally substituted with one or more (C1-C6) hydrocarbon groups;
- R90 is chosen from H, (C1-C6)alkyl, —C(═O)(C1-C6)alkyl and phenyl, or together with the nitrogen to which they are attached, R40 and R90 may form a nitrogen heterocycle, with the proviso that one of R40 and R90 must be an acyl, and when R40 and R90 together with the nitrogen to which they are attached form a heterocycle, the heterocyle must contain one or two α-oxo substituents;
- and
- wherein
- Rw, Rx and Ry are chosen independently in each instance from hydrogen, (C1-C10) hydrocarbon and (C1-C8) silaalkane;
- R100 is chosen from hydrogen and (C1-C20) hydrocarbon;
- or
- any two of R100, Rw, Rx, Ry and G2, taken together with the carbons to which they are attached, form a (C5-C8) hydrocarbon ring which may be substituted with (C1-C8)hydrocarbon, with the proviso that the C═C double bond above is not contained within a phenyl ring;
- or
- G1 and A, together with the carbon to which they are attached, can form a non-aromatic, 5- or 6-membered ring D:
- wherein Rg represents one or two substituents independently selected in each instance from hydrogen, -M-R40, (C1-C10)hydrocarbon, hydroxyl and RhCH2COO—, wherein Rh is chosen from halogen, hydroxyl, a polymer and an oligomer;
- and wherein G3 is selected from —N+(CH3)2, —(CH)—NO2, —CH(CN), —C(CN)2, —Si(CH3)2—, —CiHj(halogen)k, and CsHt(halogen)u-E, wherein i is 1-2, j is 0-3, k is 1-5, and the sum of j plus k is 2i;
- and wherein s is 1-2, t is 0-2, u is 1-4, and the sum of t plus u is 2s minus 1;
- and wherein RA and RB can each be selected independently from hydrogen, (C1-C6)alkyl and benzyl;
- R30 is chosen from
- (a) —CnHmFp wherein n is 1-8, m is 0-16, p is 1-17 and the sum of m plus p is 2n+1;
- (b) —CH2C(═O)-Q;
- (c) —CF2CH2OQ;
- (d) —CF2C(═O)-Q;
- (e) —CF2CH2C(═O)—R31, wherein R31 is selected from CH═CH2, CCH3═CH2, CHQCH2Q and CCH3QCH2Q;
- wherein Z is a direct bond, CH2, CHF or CF2;
- R60 is chosen from —CF3, —OCH3, —NO2, F, Cl, Br, —CH2Br, —CH═CH2, —OCH2CH2Br, -Q, —O-Q, —OCH2CH2-Q, —OCH2CH2O-Q, —CH(O)CH2-Q, —OC═OCH═CH2, —OC═OCCH3═CH2, —OC═OCHQCH2Q, and —OC═OCCH3QCH2Q;
- R70 represents from one to four substituents chosen independently in each instance from H, —CF3, —OCH3, —CH3, —NO2, F, Br, Cl, —CiHj(halogen)k, and CsHt(halogen)u-E, wherein i is 1-2, j is 0-3, k is 1-5, and the sum of j plus k is 2i+1;
- and wherein s is 1-2, t is 0-2, u is 1-4, and the sum of t plus u is 2s;
- E is selected from —(C1-C6)alkyl, aryl, (C1-C6)haloalkyl, haloaryl, haloaryl(C1-C2)alkyl, and aryl(C1-C2)alkyl;
- (g) —(CH2)qCl, wherein q is an integer from 1 to 8;
- (h) —CF2C(═O)NHC6H4R60;
- (i) —CH2C(═O)NHC6H4R60;
- and
- (j) —CHFC(═O)NHC6H4R60;
- and
- Q is a polymer or oligomer.
49 more elements
4-10. (canceled)
13-14. (canceled)
18-22. (canceled)
24-32. (canceled)
34-37. (canceled)
A compound of formula
- wherein
- G1 is selected from —N+(CH3)3, —(CH2)—N+(CH3)3, —(CH2)—NO2, —CH2(CN), —CH(CN)2, —(CH2)0-1SO2(C1-C8)hydrocarbon, —C6F5, —Si(CH3)3, halogen, —CiHj(halogen)k, and CsHt(halogen)u-E, wherein i is 1-2, j is 0-3, k is 1-5, and the sum of j plus k is 2i+1;
- and wherein s is 1-2, t is 0-2, u is 1-4, and the sum of t plus u is 2s;
- E is selected from —(C1-C6)alkyl, aryl, (C1-C6)haloalkyl, haloaryl, haloaryl(C1-C2)alkyl, and aryl(C1-C2)alkyl;
- R10 is chosen from (C1-C8)saturated hydrocarbon;
- (C1-C8)saturated hydrocarbon substituted with halogen, cyano or nitro;
- (C1-C8)silaalkane and optionally substituted phenyl;
- R20 is chosen from H, (C1-C6) hydrocarbon and (C1-C6) hydrocarbon substituted with nitro or cyano, or taken together with the carbon to which they are attached, R10 and R20 form a (C3-C8) hydrocarbon ring;
- R50 is chosen from H, (C1-C6) hydrocarbon, nitro, cyano, (C1-C6) hydrocarbon substituted with nitro or cyano, and (C1-C6)silaalkane, or together with the carbons to which they are attached, R10 and R50 form a (C3-C8) hydrocarbon ring;
- R30a is chosen from H, F and (C1-C6) hydrocarbon;
- and
- R30b is chosen from H and F.
9 more elements
(canceled)
44-46. (canceled)
(canceled)
Dependencies are inferred from the claim text.