Resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-9958776-B2
Application number	US-201615390855-A
Country	US
Kind code	B2
Filing date	Dec 27, 2016
Priority date	Dec 28, 2015
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

A resist composition comprising a base polymer and a phosphazene salt compound offers a high dissolution contrast, minimal LWR, and dimensional stability on PPD.

First claim

The invention claimed is:

1. A resist composition comprising a base polymer and a phosphazene salt compound having the formula (A):

wherein R 1 to R 7 are each independently hydrogen, or a C 1 -C 24 straight, branched or cyclic alkyl group, C 2 -C 24 straight, branched or cyclic alkenyl group, C 2 -C 24 straight, branched or cyclic alkynyl group, or C 6 -C 20 aryl group, which may contain an ester, ether, sulfide, sulfoxide, carbonate, carbamate, sulfone, halogen, amino, amide, hydroxy, thiol or nitro moiety, a pair of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , or R 6 and R 7 may bond together to form a ring, or a pair of R 2 and R 3 , R 4 and R 5 , or R 6 and R 7 , taken together, may form a double bond or a group having the formula (A)-1, R 1 may be a group having the formula (A)-2,

wherein R 8 to R 17 are each independently hydrogen, or a C 1 -C 24 straight, branched or cyclic alkyl group, C 2 -C 24 straight, branched or cyclic alkenyl group, C 2 -C 24 straight, branched or cyclic alkynyl group, or C 6 -C 20 aryl group, a pair of R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 14 and R 15 , or R 16 and R 17 may bond together to form a ring, or a pair of R 8 and R 9 , R 10 and R 11 , or R 12 and R 13 , taken together, may form a double bond or a group having the formula (A)-1,
A − is an anion selected from the group consisting of hydroxide, chloride, bromide, iodide, nitrate, nitrite, chlorate, chlorite, perchlorate, hydrogencarbonate, dihydrogenphosphate, hydrogensulfate, thiocyanate, hydrogenoxalate, cyanide, iodate ions, and anions of the formulae (M-1) and (M-2):

wherein R 18 is hydrogen, or a C 1 -C 30 straight, branched or cyclic alkyl group, C 2 -C 30 straight, branched or cyclic alkenyl group, C 2 -C 30 straight, branched or cyclic alkynyl group, C 6 -C 20 aryl group, C 7 -C 20 aralkyl group, or C 3 -C 20 aromatic or aliphatic heterocycle-containing group, which may contain an ester, ether, sulfide, sulfoxide, carbonate, carbamate, sulfone, halogen, amino, amide, hydroxy, thiol or nitro moiety, with the proviso that R 18 does not contain a group of the formula (A)-3:

wherein Ar is a C 6 -C 16 aromatic group, R 21 and R 22 are each independently hydrogen, hydroxy, alkoxy, C 1 -C 6 straight, branched or cyclic alkyl group, or C 6 -C 10 aryl group, R 19 is fluorine, or a C 1 -C 10 straight, branched or cyclic fluoroalkyl group or fluorophenyl group, which may contain a hydroxy, ether, ester or alkoxy moiety, R 20 is hydrogen, or a C 1 -C 10 straight, branched or cyclic alkyl group, C 2 -C 10 straight, branched or cyclic alkenyl group, C 2 -C 10 straight or branched alkynyl group, or C 6 -C 10 aryl group, which may contain a hydroxy, ether, ester or alkoxy moiety,
wherein the carboxylate anion having formula (M-1) is selected from the group consisting of the following formulae:

2. The resist composition of claim 1 , further comprising an acid generator capable of generating sulfonic acid, sulfonimide or sulfonmethide.

3. The resist composition of claim 1 , further comprising an organic solvent.

4. The resist composition of claim 1 wherein the base polymer comprises recurring units having the formula (a1) or recurring units having the formula (a2):

wherein R 31 and R 33 are each independently hydrogen or methyl, R 32 and R 34 are each independently an acid labile group, X is a single bond, ester group, phenylene group, naphthylene group or a C 1 -C 12 linking group containing lactone ring, and Y is a single bond or ester group.

5. The resist composition of claim 4 , further comprising a dissolution inhibitor.

6. The resist composition of claim 4 which is a chemically amplified positive resist composition.

7. The resist composition of claim 1 wherein the base polymer is free of an acid labile group.

8. The resist composition of claim 7 , further comprising a crosslinker.

9. The resist composition of claim 7 which is a chemically amplified negative resist composition.

10. The resist composition of claim 1 wherein the base polymer comprises recurring units of at least one type selected from the formulae (f1) to (f3):

wherein R 51 , R 55 and R 59 each are hydrogen or methyl,
R 52 is a single bond, phenylene, —O—R 63 —, or —C(═O)—Y 1 —R 63 —, Y 1 is —O— or —NH—, R 63 is a C 1 -C 6 straight, branched or cyclic alkylene or alkenylene group which may contain a carbonyl, ester, ether or hydroxyl moiety, or phenylene group,
R 53 , R 54 , R 56 , R 57 , R 58 , R 60 , R 61 , and R 62 are each independently a C 1 -C 12 straight, branched or cyclic alkyl group which may contain a carbonyl, ester or ether moiety, or a C 6 -C 12 aryl group, C 7 -C 20 aralkyl group or mercaptophenyl group,
A 1 is a single bond, -A 0 -C(═O)—O—, -A 0 -O— or -A 0 -O—C(═O)—, A 0 is a C 1 -C 12 straight, branched or cyclic alkylene group which may contain a carbonyl, ester or ether moiety,
A 2 is hydrogen or trifluoromethyl,
Z 1 is a single bond, methylene, ethylene, phenyle

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Ohashi Masaki

Classifications

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/0382

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title

• G03F7/168

  Finishing the coated layer, e.g. drying, baking, soaking · CPC title

• G03F7/0397 Primary

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title