Method using silicon-containing underlayers
Methods of manufacturing electronic devices employing wet-strippable underlayer compositions comprising a condensate and/or hydrolyzate of a polymer comprising as polymerized units one or more first unsaturated monomers having a condensable silicon-containing moiety, wherein the condensable silicon-containing moiety is pendent to the polymer backbone, and one or more condensable silicon monomers are provided.
1. A composition comprising: (a) one or more solvents; and (b) a condensate and/or hydrolyzate of (i) one or more polymers comprising as polymerized units one or more first unsaturated monomers having a condensable silicon-containing moiety, wherein the condensable silicon-containing moiety is pendent to the polymer backbone, one or more second unsaturated monomers having a chromophore moiety, and one or more third unsaturated monomers being free of a condensable silicon-containing moiety and having the formula (3)
wherein Z is chosen from an acid decomposable group, a C 4-30 organic residue bound to the oxygen through a tertiary carbon, a C 4-30 organic residue comprising an acetal functional group, and a monovalent organic residue having a lactone moiety; and R 10 is independently chosen from H, C 1-4 alkyl, C 1-4 haloalkyl, halo, and CN, and (ii) one or more condensable silicon monomers, wherein the one or more polymers are free of a pendent aromatic ring having a substituent of the formula
where each Rx is independently H or a alkyl group of 1 to 15 carbons, where each Rx may be taken together form an aliphatic ring; Lg is H, an aliphatic monovalent hydrocarbon having 1 to 10 carbons, or a monovalent aromatic group; a1=0 or 1;
and * indicates the point of attachment to the aromatic ring.
2. The composition of claim 1 wherein at least one condensable silicon monomer has the formula (8)
Si(R 50 ) p (X) 4-p (8)
wherein p is an integer from 0 to 3; each R 50 is independently chosen from a C 1-30 hydrocarbyl moiety and a substituted C 1-30 hydrocarbyl moiety; and each X is independently chosen from halo, C 1-10 alkoxy, —OH, —O—C(O)—R 50 , and —(O—Si(R 51 ) 2 ) p2 —X 1 ; X 1 is independently chosen from halo, C 1-10 alkoxy, —OH, —O—C(O)—R 50 ; each R 51 is independently chosen from R 50 and X; and p2 is an integer from 1 to 10.
3. The composition of claim 1 wherein the condensable silicon-containing moiety has the formula
*-L-SiR 1 b Y 1 3-b
wherein L is a single covalent bond or a divalent linking group; each R 1 is independently chosen from H, C 1-10 -alkyl, C 2-20 -alkenyl, C 5-20 -aryl, and C 6-20 -aralkyl;
each Y 1 is independently chosen from halogen, C 1-10 -alkoxy, C 5-10 -aryloxy, C 1-10 -carboxy; b is an integer from 0 to 2; and * denotes the point of attachment to the polymer backbone.
4. The composition of claim 3 wherein L is a divalent linking group.
5. The composition of claim 4 wherein the divalent linking group comprises one or more heteroatoms chosen from oxygen and silicon.
6. The composition of claim 4 wherein the divalent linking group is an organic radical having from 1 to 20 carbon atoms and optionally one or more heteroatoms.
7. The composition of claim 3 wherein the divalent linking group has the formula —C(═O)—O-L 1 - wherein L 1 is a single covalent bond or an organic radical having from 1 to 20 carbon atoms.
8. The composition of claim 1 wherein at least one first unsaturated monomer has the formula (1)
wherein L is a single covalent bond or a divalent linking group; each R 1 is independently chosen from H, C 1-10 -alkyl, C 2-20 -alkenyl, C 5-20 -aryl, and C 6-20 -aralkyl;
each of R 2 and R 3 are independently chosen from H, C 1-4 alkyl, C 1-4 haloalkyl, halo, C 5-20 -aryl, C 6-20 aralkyl, and CN; R 4 is chosen from H, C 1-10 alkyl, C 1-10 haloalkyl, halo, C 5-20 -aryl, C 6-20 aralkyl, and C(═O)R 5 ; R 5 is chosen from OR 6 and N(R 7 ) 2 ; R 6 is chosen from H, and C 1-20 alkyl; each R 7 is independently chosen from H, C 1-20 alkyl, and C 6-20 aryl; each Y 1 is independently chosen from halogen, C 1-10 -alkoxy, C 5-10 -aryloxy, C 1-10 -carboxy; and b is an integer from 0 to 2.
9. The composition of claim 1 wherein the condensate and/or hydrolyzate further comprises as polymerized units one or more unsaturated monomers free of a condensable silicon-containing moiety having an acidic proton and having a pKa in water from −5 to 13.
10. The composition of claim 1 wherein the chromophore moiety is pendent from the polymer backbone.
11. The composition of claim 10 wherein the chromophore moiety is chosen from pyridyl, phenyl, naphthyl, acenaphthyl, fluorenyl, carbazolyl, anthracenyl, phenanthryl, pyrenyl, coronenyl, tetracenyl, pentacenyl, tetraphenyl, benzotetracenyl, triphenylenyl, perylenyl, benzyl, phenethyl, tolyl, xylyl, styrenyl, vinylnaphthyl, vinylanthracenyl, dibenzothiophenyl, thioxanthonyl, indolyl, and acridinyl.
12. A method comprising (a) coating a substrate with a composition of claim 1 ;
(b) curing the coating layer to form a polymeric underlayer; (c) disposing a layer of a photoresist on the polymeric underlayer; (d) pattern-wise exposing the photoresist layer to form a latent image; (e) developing the latent image to form a patterned photoresist layer having a relief image therein; (f) transferring the relief image to the substrate; and (g) removing the polymeric underlayer by wet stripping.
13. The method of claim 12 wherein the polymeric underlayer is removed by wet stripping.
14. The method of claim 12 further comprising disposing a bottom antireflective coating layer directly on the polymeric underlayer and then curing the antireflective coating layer and then disposing the photoresist layer directly on the cured antireflective coating layer.