# US 7,465,528 B2 · Positive-working photosensitive composition and pattern forming method using the same

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- Number: US 7,465,528 B2
- Document ID: US7465528B2
- Status: Granted
- Kind: B2
- Application number: 11/581,407
- Filed: 2006-10-17
- Published: 2007-04-19
- Granted: 2008-12-16
- Earliest claimed: 2005-10-17
- Assignees: FUJIFILM Corporation
- Inventors: Fumiyuki Nishiyama; Kunihiko Kodama
- Web page: https://patentgrep.com/patent/US7465528B2

## CPC

- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- Y10S 430/122: Sulfur compound containing
- Y10S 430/123: Sulfur in heterocyclic ring
- 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 positive-working photosensitive composition that includes (A) a resin containing repeating units having diamantane structures and capable of decomposing under action of an acid to increase solubility in an alkali developer, (B) a compound capable of generating a specific organic acid upon irradiation with an actinic ray or radiation, and (C) a solvent.

## Claims

### Claim 1

A positive-working photosensitive composition comprising:
(A) a resin that comprises a repeating unit having a diamantane structure and can decompose under action of an acid to increase solubility in an alkali developer, and wherein the resin (A) has a weight-average molecular weight of 3,000 to 30,000 and a dispersion degree of 1.4 to 2.1;
(B) a compound that can generate an organic acid represented by formula (2), (3), (3′), (4) or (5) upon irradiation with an actinic ray or radiation; and
(C) a solvent,
in formula (2), Rf represents an organic group having a fluorine atom, R represents a hydroxyl group or an organic group, Ar represents an aromatic group, 1 represents an integer of 1 to 6, m represents an integer of 0 to 4, and n represents an integer of 0 to 4, provided that m+n is an integer of 1 or above,
in formulae (3) and (3′), A1 represents a divalent linkage group, A2 and A3 each independently represents a single bond, an oxygen atom or —N(Rx)—, Rx represents a hydrogen atom, an aryl group, an alkyl group or a cycloalkyl group, A4 represents a single bond or —C(═O)—, Ra represents a hydrogen atom or an organic group, p represents 2 or 3, Rb represents a p-valent linkage group, and when A3 is —N(Rx)—, Ra and Rx, or Rb and Rx may combine with each other to form a ring,
in formulae (4) and (5), Y represents an alkylene group substituted with at least one fluorine atom, and Rc represents an alkyl group or a cycloalkyl group.

### Claim 2 (depends on 1)

The positive-working photosensitive composition according to claim 1,
wherein the resin (A) has a weight-average molecular weight of 6,500 to 27,000 and a dispersion degree of 1.50 to 2.03.

### Claim 3 (depends on 1)

The positive-working photosensitive composition according to claim 1,
wherein the resin (A) further comprises a repeating unit having an adamantane structure.

### Claim 4 (depends on 1)

The positive-working photosensitive composition according to claim 1, wherein the resin (A) further comprises an acid-indecomposable repeating unit.

### Claim 5 (depends on 1)

The positive-working photosensitive composition according to claim 1, wherein the solvent (C) comprises an alkylene glycol monoalkyl ether carboxylate.

### Claim 6 (depends on 5)

The positive-working photosensitive composition according to claim 5,
wherein the solvent (C) further comprises at least one additional solvent selected from solvents each having at least one functional group selected from a hydroxyl group, a ketone group, a lactone group, an ester group, an ether group or a carbonate group.

### Claim 7 (depends on 6)

The positive-working photosensitive composition according to claim 6,
wherein the alkylene glycol monoalkyl ether carboxylate is propylene glycol monomethyl ether acetate, and
said at least one additional solvent is at least one solvent selected from propylene glycol monomethyl ether, cyclohexanone, γ-butyrolactone, butyl acetate or ethyl lactate.

### Claim 8 (depends on 1)

The positive-working photosensitive composition according to claim 1, wherein the resin (A) is a resin synthesized by drop polymerization.

### Claim 9 (depends on 1)

A pattern forming method comprising:
forming a photosensitive film from the positive-working photosensitive composition according to claim 1; and
exposing and developing the photosensitive film.