Aromatic resins for underlayers
View Patent ↗Polymeric reaction products of certain aromatic alcohols with certain diaryl-substituted aliphatic alcohols are useful as underlayers in semiconductor manufacturing processes.
1. A polymeric reaction product of one or more first monomers of the formula (1)
wherein Ar 1 and Ar 2 independently represent an aromatic moiety; R 1 and R 2 are independently selected from (C 1 -C 20 )alkyl, (C 2 -C 20 )alkenyl, (C 2 -C 20 )alkynyl, (C 6 -C 30 )aryl, (C 7 -C 30 )aralkyl and (C 7 -C 30 )alkaryl; X 1 is selected from OH, SH and OR 3 ; R 3 is (C 1 -C 20 )alkyl; and each of n1 and n2 is an integer independently selected from 0 to 5; wherein R 1 and R 2 may be taken together to form a 5- to 7-membered fused ring; one or more second monomers of the formula (2)
wherein Ar 3 and Ar 4 independently represent an aromatic; R 4 is selected from hydroxy, (C 1 -C 20 )alkyl, (C 1 -C 20 )alkoxy, (C 2 -C 20 )alkenyl, (C 2 -C 20 )alkynyl, mercapto, (C 1 -C 20 )alkylthio, (C 6 -C 30 )aryl, (C 7 -C 30 )aralkyl and (C 7 -C 30 )alkaryl; R 5 is selected from (C 1 -C 20 )alkyl, (C 2 -C 20 )alkenyl, (C 2 -C 20 )alkynyl, (C 6 -C 30 )aryl, (C 7 -C 30 )aralkyl and (C 7 -C 30 )alkaryl; X 2 is selected from OH, SH and OR 6 ; R 6 is (C 1 -C 20 )alkyl; n3 is an integer from 0 to 4; and n4 is an integer from 0 to 5; wherein R 4 and R 5 may be taken together to form a 5- to 7-membered fused ring; and optionally one or more third monomers of formula (3)
wherein R 7 is selected from hydroxy, (C 1 -C 20 )alkyl, (C 1 -C 20 )alkoxy, (C 2 -C 20 )alkenyl, (C 2 -C 20 )alkynyl, mercapto, (C 1 -C 20 )alkylthio, (C 6 -C 30 )aryl, (C 7 -C 30 )aralkyl and (C 7 -C 30 )alkaryl; R 8 is selected from (C 1 -C 20 )alkyl, (C 2 -C 20 )alkenyl, (C 2 -C 20 )alkynyl, and (C 7 -C 30 )aralkyl; X 3 is selected from OH, SH and OR 9 ; R 9 is (C 1 -C 20 )alkyl; and Ar 5 is an aromatic moiety.
2. The polymeric reaction product of claim 1 wherein Ar 1 is the same as Ar 2 .
3. The polymeric reaction product of claim 1 wherein Ar 3 is different from Ar 4 .
4. The polymeric reaction product of claim 3 wherein Ar 3 represents an aryl moiety having from 3 to 7 fused aromatic rings and Ar 4 represents an aryl moiety having from 2 to 4 fused aromatic rings.
5. The polymeric reaction product of claim 1 wherein at least one of Ar 3 and Ar 4 represents an aryl moiety having at least 4 fused aromatic rings.
6. The polymeric reaction product of claim 1 wherein each of n1 and n2 is independently selected from 0 to 2.
7. A method of making the polymeric reaction product of claim 1 comprising reacting the one or more first monomers with the one or more second monomers in the presence of an acid catalyst in an organic solvent.
8. A composition comprising the polymeric reaction product of claim 1 , organic solvent, and optionally one or more additives chosen from curing agents, crosslinking agents, and surfactants.
9. A process of forming a patterned layer comprising disposing a layer of the composition of claim 8 on a substrate; removing organic solvent to form a polymeric reaction product layer; disposing a layer of a photoresist on the polymeric reaction product layer; exposing the photoresist layer to actinic radiation through a mask; developing the exposed photoresist layer to form a resist pattern; and transferring the pattern to the polymeric reaction product layer to expose portions of the substrate.
10. The process of claim 9 further comprising the steps of patterning the substrate; and then removing the patterned polymeric reaction product layer.
11. The process of claim 9 further comprising the steps of disposing a conformal silicon-containing layer over the patterned polymeric reaction product layer and exposed portions of the substrate; partially etching the silicon-containing layer to expose a top surface of the patterned polymeric reaction product layer and a portion of the substrate.