# US 2015/0147698 A1 · Negative resist composition and pattern forming process

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- Number: US 2015/0147698 A1
- Document ID: US20150147698A1
- Status: Published application
- Kind: A1
- Application number: 14/552,937
- Filed: 2014-11-25
- Published: 2015-05-28
- Earliest claimed: 2013-11-28
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Jun Hatakeyama; Masayoshi Sagehashi
- Web page: https://patentgrep.com/patent/US20150147698A1

## CPC

- C08F 212/26: {Nitrogen}
- C08F 212/22: {Oxygen}
- C08F 220/26: Esters containing oxygen in addition to the carboxy oxygen
- C08F 220/303: {and one or more carboxylic moieties in the chain}
- C08L 35/00: Compositions of homopolymers or 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 carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/0382: {the macromolecular compound being present in a chemically amplified negative photoresist composition}
- G03F 7/0388: {with ethylenic or acetylenic bands in the side chains of the photopolymer}
- G03F 7/2037: {Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation}
- H10P 76/2041: {Photolithographic processes}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

A negative resist composition comprising a polymer comprising recurring units (a) of formula (1) and having a Mw of 1,000-500,000 as base resin is provided. R1 is H or methyl, X is a single bond or —C(═O)—O—R4—, R2 is a single bond or C1-C4 alkylene, R3 is C2-C8 alkylene, R4 is a single bond or C1-C4 alkylene, and 0<a≦1.0. The composition exhibits a high resolution due to controlled acid diffusion and forms a resist film which is unsusceptible to swell in the developer and hence to pattern collapse.

## Claims

### Claim 1

A negative resist composition comprising a polymer comprising recurring units (a) of the general formula (1) and having a weight average molecular weight of 1,000 to 500,000 as base resin,
wherein R1 is hydrogen or methyl, X is a single bond or —C(═O)—O—R4—, R2 is a single bond or C1-C4 alkylene group, R3 is a linear C2-C8 alkylene group, R4 is a single bond or C1-C4 alkylene group, and a is in the range: 0<a≦1.0.

### Claim 2 (depends on 1)

The negative resist composition of claim 1 wherein the polymer further comprises recurring units of at least one type selected from the group consisting of a vinylnaphthalene (b1), indene (b2), acenaphthylene (b3), chromone (b4), coumarin (b5), norbornadiene (b6), and vinylcarbazole (b7), as represented by the general formula (2):
wherein R5 is hydrogen or methyl, m is an integer of 0 to 2, n is an integer of 0 to 5, R110 to R116 are each independently hydrogen, C1-C30 alkyl, partially or entirely halo-substituted alkyl (the alkyl and halo-substituted alkyl optionally having an alkyl-substituted or unsubstituted hydroxyl or carboxyl group), hydroxyl, C1-C4 alkoxy, acyl, acyloxy, alkoxycarbonyl, C6-C10 aryl, halogen, or 1,1,1,3,3,3-hexafluoro-2-propanol group, Y is a single bond, —O—, —S—, —C(═O)—O—R6—, or —C(═O)—NH—R6—, R6 is a single bond or C1-C4 alkylene group, X0 is methylene, oxygen or sulfur atom; b1 to b7 are numbers in the range: 0≦b1<1.0, 0≦b2<1.0, 0≦b3<1.0, 0≦b4<1.0, 0≦b5<1.0, 0≦b6<1.0, 0≦b7<1.0, 0<b1+b2+b3+b4+b5+b6+b7<1.0, 0<a<1.0, and 0<a+b1+b2+b3+b4+b5+b6+b7≦1.0.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

The negative resist composition of claim 1, further comprising a basic compound and/or a surfactant.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 5)

The pattern forming process of claim 5 wherein the high-energy radiation is g-line of wavelength 430 nm, i-line of 365 nm, KrF excimer laser of 248 nm, EB, or soft X-ray in a wavelength range of 3 to 15 nm.

### Claim 7 (depends on 5)

The pattern forming process of claim 5 wherein the developer is an alkaline developer.