Aromatic resins for underlayers

Patent metadata

Field	Value
Publication number	US-9334357-B2
Application number	US-201514701463-A
Country	US
Kind code	B2
Filing date	Apr 30, 2015
Priority date	Apr 30, 2014
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

Polymeric reaction products of certain aromatic alcohols with certain diaryl-substituted aliphatic alcohols are useful as underlayers in semiconductor manufacturing processes.

First claim

What is claimed is:

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.

Assignees

• Rohm & Haas Elect Mat
• Rohm & Haas Elect Mat

Inventors

• Han Seon-Hwa
• Cho Sung Wook
• Pyun Hae-Kwang
• Lee Jung-June
• Yamada Shintaro

Classifications

• C09D165/00

  Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers · CPC title

• G03F7/405

  Treatment with inorganic or organometallic reagents after imagewise removal · CPC title

• G03F7/09

  characterised by structural details, e.g. supports, auxiliary layers (supports for printing plates in general B41N) · CPC title

• C08G2261/314

  Condensed aromatic systems, e.g. perylene, anthracene or pyrene · CPC title

• G03F7/11

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