Resins for underlayers

Patent metadata

Field	Value
Publication number	US-9880469-B2
Application number	US-201514792968-A
Country	US
Kind code	B2
Filing date	Jul 7, 2015
Priority date	Jul 15, 2014
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

Polymeric reaction products of certain substituted tetraarylmethane monomers are useful as underlayers in semiconductor manufacturing processes.

First claim

What is claimed is:

1. A polymeric reaction product comprising polymerized units of one or more tetraaryl monomers of formula (1) and one or more monomers chosen from formulae (2) and (3):

wherein AG represents an activating group chosen from OR, NR 2 , and SR; Ar 1 , Ar 2 , Ar 3 and Ar 4 independently represent an aryl moiety; R is independently H, an optionally substituted C 1-30 alkyl, an optionally substituted C 2-30 alkenyl moiety, an optionally substituted C 2-30 alkynyl moiety, an optionally substituted C 7-30 aralkyl moiety, or an optionally substituted C 6-20 aryl moiety; R 1 , R 2 , R 3 , and R 4 are independently an optionally substituted C 1-30 alkyl, an optionally substituted C 2-30 alkenyl moiety, an optionally substituted C 2-30 alkynyl moiety, an optionally substituted C 7-30 aralkyl moiety, or an optionally substituted C 6-20 aryl moiety; a is an integer from 0 to 4; b, c, and d are independently integers from 0 to 5; R 5 is selected from the group consisting of H, optionally substituted C 1-60 aliphatic moiety, and optionally substituted C 5-60 aryl moiety; Ar 5 is an optionally substituted C 5-60 aryl moiety, each R 6 is independently chosen from H, optionally substituted C 1-60 aliphatic moiety, and optionally substituted C 5-60 aryl moiety, and X is OH, C 1-2 alkoxy group or a halogen; wherein at least one of Ar 1 , Ar 2 , Ar 3 and Ar 4 is an aryl moiety having 2 or more fused aromatic rings, and wherein none of Ar 1 , Ar 2 , Ar 3 and Ar 4 are taken together along with the carbon to which they are attached to form a 5 or 6-membered fused alicyclic ring.

2. The polymeric reaction product of claim 1 wherein AG is OR.

3. The polymeric reaction product of claim 1 wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 are independently chosen from phenyl, biphenyl, naphthalenyl, anthracenyl, phenanthrenyl, pyrenyl, tetracenyl, triphenylenyl, tetraphenyl, benzo[f]tetraphenyl, benzo[m]tetraphenyl, benzo[k]tetraphenyl, pentacenyl, perylenyl, benzo[a]pyrenyl, benzo[e]pyrenyl, benzo[ghi]perylenyl, coronenyl, quinolonyl, 7,8-benzoquinolinyl, fluorenyl, chrysenyl, triphenylenyl, and 12H-dibenzo[b,h]fluorenyl.

4. A composition comprising the polymeric reaction product of claim 1 , an organic solvent, and optionally one or more additives chosen from curing agents and surfactants.

5. The composition of claim 4 wherein the curing agent is an acid or a thermal acid generator.

6. A method of forming a patterned layer comprising disposing a layer of the composition of claim 4 on a substrate; removing organic solvent to form a polymeric underlayer; disposing a layer of a photoresist on the polymeric underlayer; 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 underlayer to expose portions of the substrate.

7. A tetraaryl methane monomer having the formula (1)

wherein AG represents an activating group chosen from OR, NR 2 , and SR; Ar 1 , Ar 2 , Ar 3 and Ar 4 independently represent an aryl moiety; R is independently H, an optionally substituted C 1-30 alkyl, an optionally substituted C 2-30 alkenyl moiety, an optionally substituted C 2-30 alkynyl moiety, an optionally substituted C 7-30 aralkyl moiety, or an optionally substituted C 6-20 aryl moiety; R 1 , R 2 , R 3 , and R 4 are independently an optionally substituted C 1-30 alkyl, an optionally substituted C 2-30 alkenyl moiety, an optionally substituted C 2-30 alkynyl moiety, an optionally substituted C 7-30 aralkyl moiety, or an optionally substituted C 6-20 aryl moiety; a is an integer from 0 to 4; and b, c, and d are independently integers from 0 to 5; wherein at least one of Ar 1 , Ar 2 , Ar 3 and Ar 4 is an aryl moiety having 2 or more fused aromatic rings, and wherein none of Ar 1 , Ar 2 , Ar 3 and Ar 4 are taken together along with the carbon to which they are attached to form a 5 or 6-membered fused alicyclic ring; wherein when AG is OR, R is not a H atom, and wherein when AG is NR 2 and one R is a H atom, the other R is not a C 6 aryl moiety.

8. A tetraaryl monomer having the general formula (1-2):

AG represents an activating group chosen from OR, NR2, and SR; Ar 1 , Ar 2 , Ar 3 and Ar 4 independently represent an aryl moiety; R is independently H, an optionally substituted C 1-30 alkyl, an optionally substituted C 2-30 alkenyl moiety, an optionally substituted C 2-30 alkynyl moiety, an optionally substituted C 7-30 aralkyl moiety, or an optionally substituted C 6-20 aryl moiety; R 1 , R 2 , R 3 , and R 4 are independently an optionally substituted C 1-30 alkyl, an optionally substituted C 2-30 alkenyl moiety, an optionally substituted C 2-30 alkynyl moiety, an optionally substituted C 7-30 aralkyl moiety, or an optionally substituted C 6-20 aryl moiety; any 2 of Ar 1 , Ar 2 , Ar 3 and Ar 4 may be taken together along with the carbon to which they are attached to form a 5 or 6-membered fused alicyclic ring; a is an integer from 0 to 4; b is an integer from 0 to 5; and c″ and d″ are independently integers from 0 to 4; wherein when AG is NR 2 , the two groups are nor aryl moieties simultaneously.

9. A polymeric reaction product comprising polymerized units of one or more tetraaryl monomers of claim 8 and one or more monomers chosen from formulae (2) and (3):

wherein R 5 is selected from the group consisting of H, optionally substituted C 1-60 aliphatic moiety, and optionally substituted C 5-60 aryl moiety; Ar 5 is an optionally substituted C 5-60 aryl moiety; each R 6 is independently selected from the group consisting of H, optionally substituted C 1-60 aliphatic moiety, and optionally substituted C 5-60 aryl moiety; and X is OH, C 1-2 alkoxy group or a halogen.

10. A composition comprising the polymeric reaction product of claim 9 , an organic solvent, and optionally one or more additives chosen from curing agents and surfactants.

11. A method of forming a patterned layer comprising disposing a layer of the composition of claim 10 on a substrate; removing organic solvent to form a polymeric underlayer; disposing a layer of a photoresist on the polymeric underlayer; 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 underlayer to expose portions of the substrate.

12. A polymer comprising a repeat unit of formula (4)

wherein AG represents an activating group chosen from OR, NR 2 , and SR; Ar 1 , Ar 2 , Ar 3 and Ar 4 independently represent an aryl moiety; R is independently H, an optionally substituted C 1-30 alkyl, an optionally substituted C 2-30 alkenyl moiety, an optionally substituted C 2-30 alkynyl moiety, an optionally substituted C 7-30 aralkyl moiety, or an optionally substituted C 6-20 aryl moiety; R 1 , R 2 , R 3 , and R 4 are independently an optionally substituted C 1-30 alkyl, an optionally substituted C 2-30 alkenyl moiety, an optionally substituted C 2-30 a

Assignees

• Rohm & Haas Elect Mat
• Rohm & Haas Elect Materials Korea Ltd
• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Aqad Emad
• Li Mingqi
• Yamada Shintaro
• Cho Sung Wook

Classifications

• C07C39/17

  containing other rings in addition to the six-membered aromatic rings {, e.g. cyclohexylphenol} · CPC title

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title

• G03F7/094 Primary

  Multilayer resist systems, e.g. planarising layers · CPC title

• C07C2603/52

  containing five condensed rings · CPC title

• C07C2603/24

  Anthracenes; Hydrogenated anthracenes · CPC title