Silicon-containing underlayers

Patent metadata

Field	Value
Publication number	US-10114288-B2
Application number	US-201615254935-A
Country	US
Kind code	B2
Filing date	Sep 1, 2016
Priority date	Sep 1, 2016
Publication date	Oct 30, 2018
Grant date	Oct 30, 2018

Abstract

Wet-strippable underlayer compositions comprising one or more silicon-containing polymers comprising a backbone comprising Si—O linkages, one or more organic blend polymers, and a cure catalyst are provided. These compositions are useful in the manufacture of various electronic devices.

First claim

What is claimed is:

1. A process comprising: (a) coating a substrate with a coating composition comprising one or more curable silicon-containing polymers comprising a backbone comprising Si—O linkages, one or more organic blend polymers, and one or more organic solvents to form a curable silicon-containing polymer layer on the substrate; (b) curing the silicon-containing polymer layer to form a siloxane underlayer; (c) disposing a layer of a photoresist on the siloxane 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 siloxane underlayer by wet stripping; wherein the organic blend polymer comprises as polymerized units one or more monomers of formula (1a) and one or more monomers of formula (2)

wherein ADG is an acid decomposable group; each R 1 is independently selected from the group consisting of H, C 1-4 alkyl, C 1-4 haloalkyl, halo, and CN; and R 2 is a monovalent organic residue having a lactone moiety.

2. The process of claim 1 wherein the monomer of formula (1a) has the formula (1b)

wherein R 5 is selected from the group consisting of a C 4-30 organic residue bound to the oxygen through a tertiary carbon, and a C 4-30 organic residue comprising an acetal functional group; and R 1 is selected from the group consisting of H, C 1-4 alkyl, C 1-4 haloalkyl, halo, and CN.

3. The process of claim 1 wherein the lactone moiety of R 2 is selected from the group consisting of a 5 to 7-membered ring, and a substituted 5 to 7-membered ring.

4. The process of claim 1 wherein the coating composition further comprises one or more cure catalysts.

5. The process of claim 1 wherein the one or more silicon-containing polymers comprise as polymerized units one or more monomers chosen from formulae (3), (4), (5a), and (5b)
R 3 SiY 3   (3)

SiY 1 4   (4)

R 5 2 SiY 2 2   (5a)

R 5 3 SiY 2   (5b)

wherein each Y, Y 1 and Y 2 is independently a hydrolyzable moiety selected from the group consisting of halo, C 1-10 alkoxy, and —O—C(O)—R 4 ; R 3 is selected from the group consisting of C 1-30 hydrocarbyl moiety, and substituted C 1-30 hydrocarbyl moiety; each R 4 is independently selected from the group consisting of H, OH, C 1-10 alkyl, and C 1-10 alkoxy; and each R 5 is independently selected from the group consisting of C 1-30 hydrocarbyl moiety, and substituted C 1-30 hydrocarbyl moiety.

6. The process of claim 5 wherein the one or more silicon-containing polymers comprise as polymerized units one or more units of formula (6) and optionally one or more units of formula (7)

wherein each R 7 is independently selected from the group consisting of C 1-30 hydrocarbyl moiety, substituted C 1-30 hydrocarbyl moiety, and OR 8 ; each R 8 is independently selected from the group consisting of H, Si(R 9 ) x O(R 10 ) y , C 1-30 hydrocarbyl moiety, and substituted C 1-30 hydrocarbyl moiety; each R 9 is independently selected from the group consisting of C 1-30 hydrocarbyl moiety and substituted C 1-30 hydrocarbyl moiety; each R 10 is independently selected from the group consisting of H, C 1-10 alkyl, and —C(O)—C 1-10 alkyl; each R 11 is independently selected from the group consisting of H, C 1-10 alkyl, and —C(O)—C 1-10 alkyl; n refers to the number of repeat units of formula (6) in the polymer and is an integer from 1 to 100; m refers to the number of repeat units of formula (7) in the polymer and is an integer from 0 to 50; x=0 to 3; Y=0 to 3, and x+y=3.

7. The process of claim 1 further comprising coating a layer of a high carbon-content organic coating on the substrate prior to step (a).

8. The process of claim 1 wherein the wet stripping step comprises contacting the siloxane underlayer with a mixture of sulfuric acid and hydrogen peroxide or a mixture of ammonia and hydrogen peroxide.

9. The process of claim 1 wherein ADG is selected from the group consisting of —O—C 4-30 hydrocarbyl moiety where C 4-30 hydrocarbyl moiety is bonded to the oxygen atom through a secondary or tertiary carbon atom, a C 2-30 hydrocarbyl moiety having an anhydride moiety, a C 2-30 hydrocarbyl moiety having an imide moiety, and a C 4-30 organic residue comprising an acetal functional group.

10. A composition comprising: one or more curable silicon-containing polymers comprising a backbone comprising Si—O linkages; one or more organic blend polymers comprising as polymerized units one or more monomers of formula (1b) and one or more monomers of formula (2)

wherein R 5 is selected from the group consisting of a C 4-30 organic residue bound to the oxygen through a tertiary carbon, and a C 4-30 organic residue comprising an acetal functional group; each R 1 is independently selected from the group consisting of H, C 1-4 alkyl, C 1-4 haloalkyl, halo, and CN; and R 2 is a monovalent organic residue having a lactone moiety; and one or more cure catalysts.

11. The composition of claim 10 further comprising one or more organic solvents.

12. The composition of claim 10 wherein the one or more monomers of formula (1b) and the one or more monomers of formula (2) are in a mole ratio of 1:99 to 99:1.

13. The composition of claim 10 wherein the blend polymer further comprises as polymerized units one or more ethylenically unsaturated third monomers.

14. The composition of claim 10 wherein the lactone moiety of R 2 is selected from the group consisting of a 5 to 7-membered ring, and a substituted 5 to 7-membered ring.

15. The composition of claim 10 wherein the one or more silicon-containing polymers comprise as polymerized units one or more monomers selected from the group consisting of formulae (3), (4), (5a), and (5b)
R 3 SiY 3   (3)

SiY 1 4   (4)

R 5 2 SiY 2 2   (5a)

R 5 3 SiY 2   (5b)

wherein each Y, Y 1 and Y 2 is independently a hydrolyzable moiety selected from the group consisting of halo, C 1-10 alkoxy, and —O—C(O)—R 4 ; R 3 is selected from the group consisting of C 1-30 hydrocarbyl moiety, and substituted C 1-30 hydrocarbyl moiety; each R 4 is independently selected from the group consisting of H, OH, C 1-10 alkyl, and C 1-10 alkoxy; and each R 5 is independently selected from the group consisting of C 1-30 hydrocarbyl moiety, and substituted C 1-30 hydrocarbyl moiety.

16. The composition of claim 15 wherein the one or more silicon-containing polymers comprise as polymerized units one or more units of formula (6) and optionally one or more units of formula (7)

wherein each R 7 is independently selected from the group consisting of C 1-30 hydrocarbyl moiety, substituted C 1-30 hydrocarbyl moiety, and OR 8 ; each R 8 is independently selected from the group consisting of H, Si(R 9 ) x O(R 10 ) y , C 1-30 hydrocarbyl moiety, and substituted C 1-30 hydrocarbyl moiety; each R 9 is independently C 1-30 hydrocarbyl moiety or substituted C 1-30 hydrocarbyl moiety; each R 10 i

Assignees

• Rohm & Haas Elect Mat

Inventors

• Cutler Charlotte A
• Coley Suzanne M
• Ongayi Owendi
• Sullivan Christopher P
• Labeaume Paul J
• Cui Li
• Yamada Shintaro
• Li Mingqi
• Cameron James F

Classifications

• C08F20/32

  containing epoxy radicals · CPC title

• C08F220/24

  containing perhaloalkyl radicals · CPC title

• C08F220/282

  and containing two or more oxygen atoms · CPC title

• C08F220/325

  containing glycidyl radical, e.g. glycidyl (meth)acrylate · CPC title

• C08F220/1808

  C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate · CPC title