Aromatic resins for underlayers
Polyarylene resins and compositions containing them are useful as underlayers in semiconductor manufacturing processes.
1. A polyarylene resin comprising as polymerized units one or more first monomers of formula (1)
wherein Ar is a C 5-60 -aryl moiety; each Ar 3 and Ar 4 is independently a C 5-30 -aryl moiety; each R 1 is independently chosen from —OH and —C(═O)OR 3 ; each R 2 is independently chosen from C 1-10 -alkyl, C 1-10 -haloalkyl, C 5-30 -aryl, CN, and halo; R 3 =H or M; M=an alkali metal ion, an alkaline earth metal ion, or an ammonium ion; each a3 is independently 0 to 3; each a4 is independently 0 to 3; b1=1 to 4; b2=0 to 4; each c3 is independently 0 to 3; each c4 is independently 0 to 3; a3+a4=1 to 6; and b1+b2=2 to 6; and one or more second monomers comprising two or more cyclopentadienone moieties.
2. The polyarylene resin of claim 1 , wherein the first monomer has the formula
wherein Ar 1 is a C 5-30 aryl moiety; a1=0 to 3; and c1=0 to 3.
3. The polyarylene resin of claim 1 wherein a3+a4=2 to 4.
4. The polyarylene resin of claim 1 wherein b1+b2=2 to 4.
5. The polyarylene resin of claim 1 further comprising as polymerized units one or more third monomers of formula (13)
wherein Ar 7 is a C 5-30 -aromatic moiety; each Y 2 is independently a chemical bond or a divalent linking group chosen from —O—, —S—, —S(═O)—, —S(═O) 2 —, —C(═O)—, —(C(R 9 ) 2 ) z —, C 6-30 aryl, and —(C(R 9 ) 2 ) z1 —(C 6-30 aryl)-(C(R 9 ) 2 ) z2 ; each R is independently chosen from H or a C 5-30 -aryl moiety; each R 15 is independently chosen from C 1-4 -alkyl, C 1-4 -haloalkyl, C 1-4 -alkoxy, optionally substituted C 7-14 -aralkyl, and optionally substituted C 6-30 -aryl; b4=1 or 2;f=0 to 4; z is 1 to 10; z1 is 0 to 10; z2 is 0 to 10; and z2 is 0 to 10; and z1+z2=1 to 10.
6. The polyarylene resin of claim 5 wherein f=0.
7. The polyarylene resin of claim 1 wherein the one or more second monomers are chosen from one or more monomers of formula (9)
wherein each R 10 is independently chosen from H, C 1-6 -alkyl, or optionally substituted C 5-30 -aryl; and Ar 5 is an aromatic moiety having from 5 to 60 carbon atoms.
8. A composition comprising the polyarylene resin of claim 1 and one or more organic solvents.
9. A method of forming a patterned layer comprising:
(a) coating on a substrate a layer of the composition of claim 8 (b) removing organic solvent to form a polyarylene resin layer; (c) coating a layer of a photoresist on the polyarylene resin layer; (d) exposing the photoresist layer to actinic radiation through a mask; (e) developing the exposed photoresist layer to form a resist pattern; and (f) transferring the pattern to the polyarylene resin layer to expose portions of the substrate.
10. The method of claim 9 further comprising the steps of patterning the substrate; and then removing the patterned polyarylene resin layer.
11. The method of claim 9 further comprising the step of coating a silicon-containing layer over the polyarylene resin layer before step (c).
12. The method of claim 11 further comprising the step of transferring the pattern to the silicon-containing layer after step (c) and before step (d).