# US 7,745,094 B2 · Resist composition and patterning process using the same

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- Number: US 7,745,094 B2
- Document ID: US7745094B2
- Status: Granted
- Kind: B2
- Application number: 11/702,658
- Filed: 2007-02-06
- Published: 2007-08-16
- Granted: 2010-06-29
- Earliest claimed: 2006-02-13
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Inventors: Mutsuo Nakashima; Yoshitaka Hamada; Katsuya Takemura; Kazumi Noda
- Web page: https://patentgrep.com/patent/US7745094B2

## CPC

- G03F 7/0757: {Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence)}
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- Y10S 430/114: Initiator containing
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A resist composition is provided comprising a silicone resin, a photoacid generator, a nitrogen-containing organic compound, and a solvent. The silicone resin is obtained through cohydrolytic condensation of a mixture of three silane monomers containing a fluorinated norbornane group, an organic group having a carboxyl group protected with an acid labile group, and a lactone ring-bearing organic group, respectively. The resist composition has satisfactory resolution and overcomes the problem of a low selective etching ratio between resist film and organic film during oxygen reactive etching.

## Claims

### Claim 1

A resist composition comprising
(A) a silicone resin,
(B) an acid generator,
(C) an organic nitrogen-containing compound, and
(D) an organic solvent,
said silicone resin (A) being obtained through cohydrolytic condensation of a mixture comprising hydrolyzable silane monomers having the general formulae (1), (2) and (3):
wherein
is selected from the group consisting of the following formulae:
R4 is a C1-C6 hydrocarbon group with a straight, branched or cyclic structure,
R5 is an organic group selected from the group consisting of the following formulae:
wherein R12 is hydrogen, fluorine, methyl or trifluoromethyl, R13 is hydrogen, fluorine, methyl or trifluoromethyl, and Prot. is a protecting group selected from the group consisting of the following formulae:
wherein R9 is C1-C6 straight, branched or cyclic alkyl,
wherein R10 is C2-C6 straight, branched or cyclic alkyl, norbornyl or adamantyl, and Me is methyl, and
wherein R11 is C1-C6 straight or branched alkyl,
R6 is as defined for R4,
R7 is an organic group selected from the group consisting of the following formulae (5) and (6):
wherein Y is an oxygen atom, sulfur atom or methylene group,
R8 is as defined for R4,
X is hydrogen, chlorine, bromine, or a straight, branched or cyclic C1-C6 alkoxy group,
p is 0 or 1, q is 0 or 1, and r is 0 or 1.

### Claim 2 (depends on 1)

The resist composition of claim 1, wherein the silane monomer of formula (1) is a silane monomer having the structure (4):
wherein R4 and X are as defined above, and n is 0 or 1.

### Claim 3 (depends on 1)

The resist composition of claim 1, wherein in formula (3), R7 is an organic group having an alicyclic structure and a 5-membered lactone structure bonded thereto, and the silicon atom is bonded to one of carbon atoms in the alicyclic structure.

### Claim 4 (depends on 1)

The resist composition of claim 1, wherein the silane monomer of formula (3) is a silane monomer having the structure (5) or (6):
wherein Y is an oxygen atom, sulfur atom or methylene group, R8 and X are as defined above, n is 0 or 1, and m is 0 or 1.

### Claim 5 (depends on 1)

The resist composition of claim 1, wherein said mixture further comprises a hydrolyzable monomer having at least two hydrolyzable substituent groups other than formulae (1), (2) and (3).

### Claim 6 (depends on 1)

The resist composition of claim 1, wherein said mixture further comprises a compound having the general formula (7):
SiX4 (7)
wherein X is as defined above.

### Claim 7 (depends on 1)

A pattern forming process comprising the steps of:
forming a pattern on an aromatic-containing resin film using the resist composition of claim 1, and
etching the resin film through the resulting pattern as an etching mask for thereby patterning the resin film.

### Claim 8 (depends on 7)

The pattern forming process of claim 7, wherein the etching step uses a gas plasma containing oxygen.