Antireflective composition for photoresists
View Patent ↗The invention relates to an antireflective coating composition for a photoresist layer comprising a polymer, a crosslinking agent and an acid generator, where the polymer comprises at least one unit of structure 1, where, A is a nonaromatic linking moiety, R′ and R″ are independently selected from hydrogen, Z and W—OH, where Z is a (C 1 -C 20 ) hydrocarbyl moiety and W is a (C 1 -C 20 ) hydrocarbyl linking moiety, and, Y′ is independently a (C 1 -C 20 ) hydrocarbyl linking moiety. The invention further relates to a process for imaging the antireflective coating composition.
1. An antireflective coating composition for a photoresist layer, where the antireflective coating composition comprises a polymer, a crosslinking agent and a thermal acid generator, further where the polymer comprises at least one unit of structure 2,
where,
B is a single bond or C 1 -C 6 nonaromatic aliphatic moiety,
R′ and R″ are independently selected from hydrogen, Z and W—OH, where Z is a (C 1 -C 20 ) hydrocarbyl moiety and W is a (C 1 -C 20 ) hydrocarbyl linking moiety, and,
Y′ is independently a (C 1 -C 20 ) hydrocarbyl linking moiety.
2. The composition of claim 1 , where W is selected from substituted or unsubstituted aliphatic (C 1 -C 20 ) alkylene group, substituted or unsubstituted thia-alkylene aliphatic (C 1 -C 20 ) group, substituted or unsubstituted cycloalkylene, alkoxy alkylene, hetero cycloalkylene, and mixtures thereof.
3. The composition of claim 1 where Y′ is selected from methylene, ethylene, propylene, butylene, phenylethylene, alkylnitroalkylene, neopentylene, alkylenearylate, dithiaoctylene, bromonitroalkylene, phenylene, naphthylene, derivatives of phenylene, derivatives of naphthylene, and derivatives of anthracylene.
4. The composition of claim 1 , where Y′ is selected from 1-phenyl-1,2-ethylene, neopentylene, ethylenephenylate, 2-bromo-2-nitro-1,3-propylene, 2-bromo-2-methyl-1,3-propylene, polyethyleneglycol, 1-phenylate-1,2-ethylene, 1-benzylate-1,2-ethylene, —CH 2 OCH 2 —, CH 2 CH 2 OCH 2 CH 2 —, —CH 2 CH 2 SCH 2 CH 2 —, —CH 2 CH 2 SCH 2 CH 2 SCH 2 CH 2 —, propylenephenyl acetate, 2-propylenephenyl acetate (—CH 2 CH 2 (CH 2 CO 2 CH 2 Ph), propylene phenyl ether (—CH 2 CH 2 (CH 2 OPh), propylene phenolate (—CH 2 CH 2 (CH 2 CO 2 Ph), propylene naphthoate, propylenephthalimide, propylenesuccinimide, propylene crotylidene acetate (—CH 2 CH 2 (CH 2 CO 2 CHCHCHCHCH 3 ).
5. The composition of claim 1 , where the crosslinking agent is selected from melamines, methylols, glycolurils, polymeric glycolurils, hydroxy alkyl amides, epoxy and epoxy amine resins, blocked isocyanates, and divinyl monomers.
6. The composition of claim 1 , where the thermal acid generator is selected from alkyl ammonium salts of organic acids, phenolic sulfonate esters, nitrobenzyl tosylates, and metal-free iodonium and sulfonium salts.
7. The composition of claim 1 , where the polymer is partially crosslinked polymer.
8. The composition of claim 1 , where the composition further comprises other polymers selected from polyhydroxystyrene, novolak, polyarylate and polymethylmethacrylate.
9. An article comprising a substrate with a layer of antireflective coating composition of claim 1 and thereon a coating of photoresist comprising a polymer and a photoactive compound.
10. A process for forming an image comprising,
a) coating and baking a substrate with the antireflective coating composition of claim 3 ;
b) coating and baking a photoresist film on top of the antireflective coating;
c) imagewise exposing the photoresist;
d) developing an image in the photoresist;
e) optionally, baking the substrate after the exposing step.
11. The process of claim 10 , where the photoresist is imagewise exposed at wavelengths between 130 nm to 250 nm.
12. The process of claim 10 , where the photoresist comprises a polymer and a photoactive compound.
13. The process of claim 10 , where the antirefleotive coating is baked at temperatures greater than 90° C.
14. The composition of claim 1 , where Z is selected from substituted or unsubstituted aliphatic (C 1 -C 20 ) alkyl group, substituted or unsubstituted aliphatic (C 1 -C 20 ) cycloalkyl group, substituted or unsubstituted aliphatic (C 1 -C 20 ) aryl group, and substituted or unsubstituted aliphatic (C 1 -C 20 ) alkylenearyl group.
15. The composition of claim 1 , where W—OH is selected from methanol, ethanol, propanol, isopropanol, 1-butanol, isobutanol, 2-methyl-2-butanol, 2-methyl-1-butanol, 3-methyl-1-butanol, tertiary butanol, cyclopentanol, cyclohexanol, 1-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 1-n-octanol, 2-n-octanol, and 1-phenyl-1-ethanol.
16. The composition of claim 1 , where R′ and R″ are independently W—OH, where W is a (C 1 -C 20 ) hydrocarbyl linking moiety.
17. An antireflective costing composition for a photoresist layer, where the antireflective coating composition comprises a polymer, a crosslinking agent and a thermal acid generator, further where the polymer comprises at least one unit of structure 2,
where, B is a single bond or C 1 -C 6 nonaromatic aliphatic moiety, R′ and R″ are independently selected from hydrogen, Z and W—OH, where Z is a (C 1 -C 20 ) hydrocarbyl moiety and W is a (C 1 -C 20 ) hydrocarbyl linking moiety, and,
Y′ is independently a (C 1 -C 20 ) hydrocarbyl linking moiety, and where the composition further comprises a photoacid generator.
18. An antireflective coating composition for a photoresist layer where the antireflective coating composition comprises a polymer, a crosslinking agent and a thermal acid generator, further where the polymer comprises at least one unit of structure
where R′ and R″ are independently selected from hydrogen, Z and W—OH, where Z is a (C 1 -C 20 ) hydrocarbyl moiety and W is a (C 1 -C 20 ) hydrocarbyl linking moiety, and, Y′ is independently a (C 1 -C 20 ) hydrocarbyl linking moiety.
19. The composition of claim 18 where W is independently selected from substituted or unsubstituted aliphatic (C 1 -C 20 ) alkylene group, substituted or unsubstituted thia-alkylene aliphatic (C 1 -C 20 ) group, substituted or unsubstituted cycloalkylene, alkoxy alkylene, hetero cycloalkylene, and mixtures thereof, and where Y′ is selected from methylene, ethylene, propylene, butylene, phenylethylene, alkylnitroalkylene, neopentylene, alkylenearylate, dithiaoctylene, bromonitroalkylene, phenylene, naphthylene, derivatives of phenylene, derivatives of naphthylene, and derivatives of anthracylene.
20. An antireflective coating composition for a photoresist layer where the antireflective coating composition comprises a polymer, a crosslinking agent and a thermal acid generator, further where the polymer comprises at least one unit selected from