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US 8,507,179 B2Granted
Switchable antireflective coatings
AssigneeDow Corning Corporation
InventorsPeng-Fei Fu, Eric Moyer, Jason Suhr
Life of this patent
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Abstract
An antireflective coating compositions comprising (I) a silsesquioxane resin (II) a compound selected from photo-acid generators and thermal acid generators; and (III) a solvent wherein in the silsesquioxane resin contains a carboxylic acid forming group or a sulfuric acid forming group.
Claims12
An antireflective coating compositions comprising
- (I) a silsesquioxane comprising the units
- (Ph(CH2)rSiO(3-x)/2(OR′)x)m
- (HSiO(3-x)/2(OR′)x)n
- (MeSiO(3-x)/2(OR′)x)o
- (RSiO(3-x)/2(OR′)x)p
- (R1SiO(3-x)/2(OR′)x)q
- (II) a compound selected from photo-acid generators and thermal acid generators;
- and
- (III) a solvent
- wherein in the silsesquioxane resin Ph is a phenyl group, Me is a methyl group;
- R′ is hydrogen atom or a hydrocarbon group having from 1 to 4 carbon atoms;
- each R is a carboxylic acid forming group of general formula —R2C(O)OR3 or a sulfuric acid forming group of general formula —R2SO3R3 with optionally trace amounts of the corresponding carboxylic acid or sulfuric acid, wherein R2 is selected from alkylene groups having 1-10 carbon atoms and polyether groups having the general formula —(CH2)a[O(CH2)b]f— where a has a value of 1 to 12, b has a value of 2 to 6 and f has a value of 1 to 10 and R3 is a protecting group selected from t-butyl, trimethylsilyl, anhydride groups, methylthiomethyl ester, benzyloxymethyl ester, diphenylmethyl ester and p-methoxybenzyl ester;
- and each R1 is independently selected from substituted phenyl groups, ester groups, polyether groups;
- mercapto groups, sulfur-containing organic functional groups, hydroxyl producing group, aryl sulfonic ester groups, and reactive or curable organic functional groups;
- and r has a value of 0, 1, 2, 3, or 4;
- x has a value of 0, 1 or 2;
- m has a value of 0 to 0.95;
- n has a value of 0.05 to 0.95;
- o has a value of 0 to 0.95;
- p has a value of 0.05 to 0.5;
- q has a value of 0 to 0.95;
- and m+n+o+p+q≈1.
19 more elements
A method comprising
- (a) applying an antireflective coating composition comprising a silsesquioxane resin and a thermal acid generator on a substrate;
- (b) thermally curing the antireflective coating composition to produce a wet-etchable antireflective coating;
- (c) forming a resist coating over the antireflective coating;
- (d) exposing the resist to radiation;
- (e) developing the resist and the antireflective coating
- wherein the silsesquioxane resin comprises the units
- (Ph(CH2)rSiO(3-x)/2(OR′)x)m
- (HSiO(3-x)/2(OR′)x)n
- (MeSiO(3-x)/2(OR′)x)o
- (RSiO(3-x)/2(OR′)x)p
- (R1SiO(3-x)/2(OR′)x)q and
- where Ph is a phenyl group, Me is a methyl group;
- R′ is hydrogen atom or a hydrocarbon group having from 1 to 4 carbon atoms;
- each R is a carboxylic acid forming group of general formula —R2C(O)OR3 or a sulfuric acid forming group of general formula —R2SO3R3 with optionally trace amounts of the corresponding carboxylic acid or sulfuric acid, wherein R2 is selected from alkylene groups having 1-10 carbon atoms and polyether groups having the general formula —(CH2)a[O(CH2)b]f— where a has a value of 1 to 12, b has a value of 2 to 6 and f has a value of 1 to 10 and R3 is a protecting group selected from t-butyl, trimethylsilyl, anhydride groups, methylthiomethyl ester, benzyloxymethyl ester, diphenylmethyl ester and p-methoxybenzyl ester;
- and R1 is selected from substituted phenyl groups, ester groups, polyether groups;
- mercapto groups, sulfur-containing organic functional groups, hydroxyl producing group, aryl sulfonic ester groups, and reactive or curable organic functional groups;
- and r has a value of 0, 1, 2, 3, or 4;
- x has a value of 0, 1 or 2;
- wherein in the resin m has a value of 0 to 0.95;
- n has a value of 0.05 to 0.95;
- o has a value of 0 to 0.95;
- p has a value of 0.05 to 0.5;
- q has a value of 0 to 0.95;
- and m+n+o+p+q≈1.
21 more elements
A method comprising
- (a) forming an antireflective coating (ARC) on a substrate wherein the ARC composition comprises a silsesquioxane resin and a photo-acid generator;
- optionally (b) exposing the ARC to radiation to produce a wet-etchable antireflective coating;
- (c) forming a resist coating over the antireflective coating;
- (d1) exposing the resist and ARC to radiation;
- or, when (b) is performed, (d2) exposing the resist to radiation;
- (e) developing the resist and the antireflective coating
- wherein the silsesquioxane resin is comprised of the units
- (Ph(CH2)rSiO(3-x)/2(OR′)x)m
- (HSiO(3-x)/2(OR′)x)n
- (MeSiO(3-x)/2(OR′)x)o
- (RSiO(3-x)/2(OR′)x)p
- (R1SiO(3-x)/2(OR′)x)q and
- where Ph is a phenyl group, Me is a methyl group;
- R′ is hydrogen atom or a hydrocarbon group having from 1 to 4 carbon atoms;
- each R is a carboxylic acid forming group or a sulfuric acid forming group with optionally trace amounts of the corresponding carboxylic acid of general formula —R2C(O)OR3 or sulfuric acid of general formula —R2SO3R3, wherein R2 is selected from alkylene groups having 1-10 carbon atoms and polyether groups having the general formula —(CH2)a[O(CH2)b]f— where a has a value of 1 to 12, b has a value of 2 to 6 and f has a value of 1 to 10 and R3 is a protecting group selected from t-butyl, trimethylsilyl, anhydride groups, methylthiomethyl ester, benzyloxymethyl ester, diphenylmethyl ester and p-methoxybenzyl ester;
- and R1 is selected from substituted phenyl groups, ester groups, polyether groups;
- mercapto groups, sulfur-containing organic functional groups, hydroxyl producing group, aryl sulfonic ester groups, and reactive or curable organic functional groups;
- and r has a value of 0, 1, 2, 3, or 4;
- x has a value of 0, 1 or 2;
- wherein in the resin m has a value of 0 to 0.95;
- n has a value of 0.05 to 0.95;
- o has a value of 0 to 0.95;
- p has a value of 0.05 to 0.5;
- q has a value of 0 to 0.95;
- and m+n+o+p+q≈1.
22 more elements
Dependencies are inferred from the claim text.