# US 8,771,923 B2 · Radiation-sensitive composition

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- Number: US 8,771,923 B2
- Document ID: US8771923B2
- Status: Granted
- Kind: B2
- Application number: 13/719,264
- Filed: 2012-12-19
- Published: 2013-05-02
- Granted: 2014-07-08
- Earliest claimed: 2006-09-08
- Assignees: Jsr Corporation
- Applicants: JSR Corporation
- Inventors: Nobuji Matsumura; Daisuke Shimizu; Toshiyuki Kai
- Web page: https://patentgrep.com/patent/US8771923B2

## CPC

- G03F 7/004: Photosensitive materials (G03F7/12, G03F7/14 take precedence)
- C07C 309/12: containing esterified hydroxy groups bound to the carbon skeleton
- C07C 381/12: Sulfonium compounds
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- 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)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A radiation-sensitive composition includes a low-molecular-weight compound, a solvent and a radiation-sensitive acid-generator other than the low-molecular-weight compound. The low-molecular-weight compound has one or more acid-dissociable groups which decompose by an action of an acid to enhance solubility in an alkaline developing solution and one or more radiation-sensitive acid-generating groups which generate an acid upon application of an active ray or radiation per molecule. The low-molecular-weight compound has a polystyrene-reduced number-average molecular weight (Mn) measured by gel permeation chromatography (GPC) of 500 to 4,000. The low-molecular-weight compound is not obtained from chain growth polymerization of a monomer with an unsaturated bond. A content of the low-molecular-weight compound is 80 mass % or more of 100 mass % of a total solid component of the radiation-sensitive composition. The low-molecular-weight compound is a compound shown by a following formula (1).

## Claims

### Claim 1

A radiation-sensitive composition comprising:
a low-molecular-weight compound having one or more acid-dissociable groups which decompose by an action of an acid to enhance solubility in an alkaline developing solution and one or more radiation-sensitive acid-generating groups which generate an acid upon application of an active ray or radiation per molecule, and having a polystyrene-reduced number-average molecular weight (Mn) measured by gel permeation chromatography (GPC) of 500 to 4,000, wherein the low-molecular-weight compound is not obtained from chain growth polymerization of a monomer with an unsaturated bond;
a solvent; and
a radiation-sensitive acid-generator other than the low-molecular-weight compound,
wherein a content of the low-molecular-weight compound is 80 mass % or more of 100 mass % of a total solid component of the radiation-sensitive composition, and
wherein the low-molecular-weight compound is a compound shown by a following formula (1),
wherein
A represents
an aliphatic group having 1 to 50 carbon atoms,
an aromatic group having 6 to 50 carbon atoms,
an organic group consisting of said aliphatic and said aromatic group, or
a group having a valence which is a sum of l+m+n and which has two or more of the aliphatic group represented by A, the aromatic group represented by A, or the organic group represented by A;
X represents —O—, —CH2C(═O)—O—, —C(═O)—O—, —OC(O)O—, or —Ar1—O—, wherein Ar1 represents a 1,4-phenylene group;
R1 represents an acid-dissociable group which is a substituted or unsubstituted tertiary hydrocarbon group having 4 to 12 carbon atoms or a substituted or unsubstituted acetal group;
Y represents —CH2—C(═O)—O—R2—, wherein R2 represents a substituted or unsubstituted methylene group or a substituted or unsubstituted alkylene group having 2 to 30 carbon atoms;
l is an integer from 1 to 4;
m is an integer from 1 to 3;
n is an integer from 0 to 10; and
Z is an organic group shown by a formula (2), a formula (3), a formula (4), or a formula (5) and, in a case where m is 2 or 3, the organic groups represented by Z are either a same or different,
wherein
M1+ in the formula (2) represents a monovalent onium cation;
M2+ in the formula (3) represents a monovalent onium cation;
R3 in the formula (3) and the formula (5) represents a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted aryl group having 1 to 15 carbon atoms;
P in the formula (4) represents a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms or a substituted or unsubstituted arylene group having 2 to 10 carbon atoms; and
Q in the formula (5) represents a group shown by a formula (6), a formula (7), or a formula (8),
wherein an amount of the radiation-sensitive acid generator is from 0.1 to 10 parts by mass for 100 parts by mass of the low-molecular-weight compound.

### Claim 2 (depends on 1)

The radiation-sensitive composition according to claim 1, further comprising an acid diffusion controller shown by
wherein
each R16 is independently a hydrogen atom or a substituted or unsubstituted alkyl group, aryl group, or aralkyl group;
each of R17 to R21 is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted alicyclic hydrocarbon group; and
X− represents OH−, R22OH−, or R22COO−, wherein R22 is a monovalent organic group.

### Claim 3 (depends on 2)

The radiation-sensitive composition according to claim 2, wherein an amount of the acid diffusion controller is from 0.1 to 1 part by mass for 100 parts by mass of an amount of the low-molecular-weight compound.

### Claim 4 (depends on 1)

The radiation-sensitive composition according to claim 1, wherein M1+ in the formula (2) is a sulfonium cation, an iodonium cation, a phosphonium cation, a diazonium cation, an ammonium cation, or a pyridinium cation.

### Claim 5 (depends on 1)

The radiation-sensitive composition according to claim 1, wherein M2+ in the formula (3) is a group shown by a formula (3-1), a formula (3-2), a formula (3-3), or a formula (3-4),
wherein
each R4 independently represents an alkyl group, an alkoxyl group, a trifluoromethyl group, or a fluorine atom; and
k is independently an integer of 0 to 3.