Silicon-containing underlayers

Patent metadata

Field	Value
Publication number	US-11733609-B2
Application number	US-202117370541-A
Country	US
Kind code	B2
Filing date	Jul 8, 2021
Priority date	Nov 10, 2017
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

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.

First claim

What is claimed is:

1. A composition comprising: (a) one or more solvents; (b) a condensate and/or hydrolyzate of (i) one or more condensed silicon-containing 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 a backbone of the polymer, the one or more first unsaturated monomers having the formula (1)

wherein L is a single bond or a divalent linking group; each R 1 is independently chosen from H, C 1-10 -alkyl, C-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, halogen, C 5-20 -aryl, C 6-20 aralkyl, and CN; R 4 is chosen from H, C 1-10 alkyl, C 1-10 haloalkyl, halogen, 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, and C 1-10 -carboxy; and b is an integer from 0 to 2 and (ii) one or more condensable silicon monomers; wherein the condensate and/or hydrolyzate further comprises as polymerized units one or more second unsaturated monomers free of a condensable silicon-containing moiety, wherein at least one second unsaturated monomer has the formula

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, halogen, and CN, and (c) one or more crosslinkers free of Si—O linkages.

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 halogen, 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 halogen, C 1-10 alkoxy, —OH, and —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 2 wherein p=0 or 1.

4. The composition of claim 1 wherein L is a divalent linking group.

5. 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.

6. The composition of claim 4 wherein the divalent linking group has the formula —C(═O)—O-L 1 - wherein L 1 is a single bond or an organic radical having from 1 to 20 carbon atoms.

7. The composition of claim 1 wherein at least one second unsaturated monomer has an acidic proton and having a pKa in water from −5 to 13.

8. The composition of claim 1 wherein the condensate and/or hydrolyzate further comprises as polymerized units one or more unsaturated monomers having a chromophore moiety.

9. The composition of claim 8 wherein the chromophore moiety is pendent from the polymer backbone.

10. A method comprising (a) coating a substrate with the composition of claim 1 to form a coating layer; (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.

11. The method of claim 10 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 halogen, 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 halogen, C 1-10 alkoxy, —OH, and —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.

12. The method of claim 10 wherein L is a divalent linking group having the formula —C(═O)—O-L 1 - wherein L 1 is a single bond or an organic radical having from 1 to 20 carbon atoms.

13. The method of claim 10 wherein the condensate and/or hydrolyzate further comprises as polymerized units one or more unsaturated monomers having a chromophore moiety.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Cutler Charlotte A
• Cui Li
• Yamada Shintaro
• Labeaume Paul J
• Coley Suzanne M
• Cameron James F
• Greene Daniel

Classifications

• G03F7/0752 Primary

  in non photosensitive layers or as additives, e.g. for dry lithography · CPC title

• C08F230/08

  containing silicon · CPC title

• C08F230/085

  the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title

• G03F7/162

  Coating on a rotating support, e.g. using a whirler or a spinner · CPC title