Positive resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-9429843-B2
Application number	US-201514598549-A
Country	US
Kind code	B2
Filing date	Jan 16, 2015
Priority date	Jan 24, 2014
Publication date	Aug 30, 2016
Grant date	Aug 30, 2016

Abstract

A positive resist composition is provided comprising a polymer comprising recurring units having a carboxyl or phenolic hydroxyl group substituted with an acid labile group and recurring units of caramel furanone ester, and having a Mw of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.

First claim

The invention claimed is:

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

wherein R 1 is hydrogen or methyl, R 2 is methyl or ethyl, and X is a single bond, a C 1 -C 12 linking group having an ester radical, ether radical or lactone ring, phenylene group or naphthylene group.

2. The resist composition of claim 1 wherein the polymer comprises recurring units (a) and acid labile group-substituted recurring units (b1) and/or (b2), as represented by the general formula (2):

wherein R 1 , R 2 and X are as defined above, R 3 and R 5 each are hydrogen or methyl, R 4 and R 8 each are an acid labile group, R 6 is a single bond or a straight or branched C 1 -C 6 alkylene group, R 7 is hydrogen, fluorine, trifluoromethyl, cyano, or straight, branched or cyclic C 1 -C 6 alkyl 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 having an ester radical, ether radical or lactone ring, phenylene group or naphthylene group, Y 2 is a single bond, —C(═O)—O— or —C(═O)—NH—, a, b1 and b2 are numbers in the range: 0<a<1.0, 0≦b1<1.0, 0≦b2<1.0, 0<b1+b2<1.0, and 0.1≦a+b1+b2≦1.0.

3. The resist composition of claim 2 wherein the polymer further comprises recurring units (c) having an adhesive group selected from the class 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 sulfur or NH and c is a number in the range: 0<c≦0.9 and 0.2≦a+b1+b2+c≦1.0.

4. The resist composition of claim 3 wherein in addition to the recurring units (a), (b1) and/or (b2), and (c), the polymer further comprises recurring units of at least one type selected from sulfonium salt units (d1) to (d3) represented by the general formula (3):

wherein R 20 , R 24 , and R 28 each are hydrogen or methyl, R 21 is a single bond, phenylene, —O—R—, or —C(═O)—Y 0 —R—, Y 0 is oxygen or NH, R is a straight, branched or cyclic C 1 -C 6 alkylene group, alkenylene or phenylene group, which may contain a carbonyl, ester, ether or hydroxyl radical, 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 radical, or a C 6 -C 12 aryl, C 7 -C 20 aralkyl, or thiophenyl group, Z 0 is a single bond, methylene, ethylene, phenylene, fluorophenylene, —O—R 32 —, or —C(═O)—Z 1 —R 32 —, Z 1 is oxygen or NH, R 32 is a straight, branched or cyclic C 1 -C 6 alkylene group, alkenylene or phenylene group, which may contain a carbonyl, ester, ether or hydroxyl radical, M − is a non-nucleophilic counter ion, d1, d2 and d3 are in the range: 0≦d1≦0.5, 0≦d2≦0.5, 0≦d3≦0.5, 0<d1+d2+d3≦0.5, and 0.2≦a+b1+b2+c+d1+d2+d3≦1.0.

5. The resist composition of claim 1 , further comprising an organic solvent and an acid generator, the composition being a chemically amplified resist composition.

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

7. A pattern forming process comprising the steps of applying the positive 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 having a wavelength of 3 to 15 nm.

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Hasegawa Koji

Classifications

• G03F7/0392

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

• C08F24/00

  Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F18/00; cyclic anhydrides of unsaturated acids C08F20/00, C08F22/00) · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• C08F28/02

  by a bond to sulfur · CPC title

• G03F7/30

  Imagewise removal using liquid means · CPC title