Resist composition and pattern forming process

Patent metadata

Field	Value
Publication number	US-9720324-B2
Application number	US-201615210025-A
Country	US
Kind code	B2
Filing date	Jul 14, 2016
Priority date	Jul 28, 2015
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

A resist composition is provided comprising a polymer comprising recurring units (a) having an oxazolidinedione, thioxooxazolidinone, thiazolidinedione or thioxothiazolidinone structure and recurring unit (b1) having an acid labile group-substituted carboxyl group and/or recurring units (b2) having an acid labile group-substituted phenolic hydroxyl group. The resist composition suppresses acid diffusion, exhibits a high resolution, and forms a pattern of satisfactory profile with low edge roughness.

First claim

The invention claimed is:

1. A resist composition comprising as base resin a polymer comprising recurring units represented by the formula (a) and recurring units having a carboxyl group substituted with an acid labile group and/or recurring units having a phenolic hydroxyl group substituted with an acid labile group, the polymer having a weight average molecular weight of 1,000 to 500,000,

wherein R 1 is hydrogen or methyl, R 2 and R 3 are each independently hydrogen or a straight, branched or cyclic C 1 -C 6 alkyl group, X 1 is a single bond, a C 1 -C 12 linking group containing an ester moiety, ether moiety or lactone ring, phenylene or naphthylene group, X 2 and X 3 are each independently oxygen or sulfur, and a is a positive number in the range: 0<a<1.0.

2. The resist composition of claim 1 wherein the recurring units having a carboxyl group substituted with an acid labile group are represented by the formula (b1) and the recurring units having a phenolic hydroxyl group substituted with an acid labile group are represented by the formula (b2):

wherein R 4 and R 6 are each independently hydrogen or methyl. R 5 and R 9 are each independently an acid labile group, R 7 is a single bond or a straight or branched C 1 -C 6 alkylene group, R 6 is hydrogen, fluorine, trifluoromethyl, cyano, or a straight, branched or cyclic C 1 -C 6 alkyl, acyl, alkoxy, acyloxy or alkoxycarbonyl group, p is 1 or 2, q is an integer of 0 to 4, Y 1 is a single bond, a C 1 -C 12 linking group containing an ester moiety, ether moiety or lactone ring, phenylene or naphthylene group, Y 2 is a single bond, —C(═O)—O— or —C(═O)—NH—, b1 and b2 are numbers in the range: 0≦b1<1.0, 0≦b2<1.0, and 0<b1+b2<1.0.

3. The resist composition of claim 1 wherein the polymer further comprises recurring units having an adhesive group selected from the group consisting of hydroxyl, carboxyl, lactone ring, carbonate, thiocarbonate, carbonyl, cyclic acetal, ether, ester, sulfonic acid ester, cyano, amide, and —O—C(═O)-G- wherein G is —S— or —NH—.

4. The resist composition of claim 1 wherein the polymer further comprises recurring units of at least one type selected from recurring units represented by the formulae (d1) to (d3):

wherein R 20 , R 24 , and R 28 are each independently hydrogen or methyl, R 21 is a single bond, phenylene, —O—R A —, or —C(═O)—Y 0 —R A —, Y 0 is —O— or —NH—, R A is a straight, branched or cyclic C 1 -C 6 alkylene or alkenylene group which may contain a carbonyl, ester, ether or hydroxyl moiety, or phenylene group, R 22 , R 23 , R 25 , R 26 , R 27 , R 29 , R 30 , and R 31 are each independently a straight, branched or cyclic C 1 -C 12 alkyl group which may contain a carbonyl, ester or ether moiety, or a C 6 -C 12 aryl, C 7 -C 20 aralkyl, or meroaptophenyl group, Z 1 is a single bond, a straight, branched or cyclic C 1 -C 12 alkylene or C 2 -C 12 alkenylene group which may contain an ether moiety, ester moiety or lactone ring, or C 6 -C 10 arylene group, Z 2 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, —O—R 32 —, or —C(═O)—Z 3 —R 32 —, Z 3 is —O— or —NH—, R 32 is a straight, branched or cyclic C 1 -C 12 alkylene or C 2 -C 12 alkenylene group which may contain a carbonyl, ester, ether or hydroxyl moiety, or phenylene group, M − is a non-nucleophilic counter ion, d1, d2 and d3 are numbers in the range: 0≦d1≦0.5, 0≦d2≦0.5, 0≦d3≦0.5, and 0<d1+d2+d3≦0.5.

5. The resist composition of claim 1 , further comprising an acid generator and an organic solvent.

6. The resist composition of claim 5 , further comprising a basic compound and/or a surfactant.

7. A pattern forming process comprising the steps of applying the resist composition of claim 1 onto a substrate to form a coating, baking, exposing the coating to high-energy radiation, and developing the exposed coating in a developer.

8. The process of claim 7 wherein the high-energy radiation is i-line, KrF excimer laser, ArF excimer laser, electron beam or soft X-ray of wavelength 3 to 15 nm.

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Hasegawa Koji

Classifications

• G03F7/0382

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

• C08F226/06

  by a heterocyclic ring containing nitrogen · CPC title

• C08F28/02

  by a bond to sulfur · CPC title

• C08F18/22

  Esters containing nitrogen · CPC title

• G03F7/2055

  for the production of printing plates; Exposure of liquid photohardening compositions · CPC title