# US 2019/0377261 A1 · Actinic ray-sensitive or radiation-sensitive resin composition, resist film, pattern forming method, and method for manufacturing electronic device

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- Number: US 2019/0377261 A1
- Document ID: US20190377261A1
- Status: Published application
- Kind: A1
- Application number: 16/546,867
- Filed: 2019-08-21
- Published: 2019-12-12
- Earliest claimed: 2017-03-31
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Kyohei Sakita; Mitsuhiro Fujita; Takumi Tanaka; Keishi Yamamoto; Akiyoshi Goto; Keita Kato
- Web page: https://patentgrep.com/patent/US20190377261A1

## CPC

- 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 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- H10P 76/2041: {Photolithographic processes}
- G03F 7/168: {Finishing the coated layer, e.g. drying, baking, soaking}
- G03F 7/2006: {using coherent light; using polarised light}
- G03F 7/2041: {in the presence of a fluid, e.g. immersion; using fluid cooling means}
- G03F 7/325: {Non-aqueous compositions}
- G03F 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)}
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- 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

An actinic ray-sensitive or radiation-sensitive resin composition contains a resin having an acid-decomposable group whose polarity increases through decomposition by the action of an acid, an acid generator A capable of generating a first acid upon irradiation with actinic rays or radiation, and an acid generator B capable of generating a second acid upon irradiation with actinic rays or radiation, and the first acid and the second acid satisfy predetermined requirements.

## Claims

### Claim 1

An actinic ray-sensitive or radiation-sensitive resin composition comprising:
a resin having an acid-decomposable group whose polarity increases through decomposition by the action of an acid;
an acid generator A capable of generating a first acid upon irradiation with actinic rays or radiation; and
an acid generator B capable of generating a second acid upon irradiation with actinic rays or radiation,
wherein the second acid is capable of decomposing the acid-decomposable group and has a larger pKa than the first acid, and
in a case where a decomposition reaction rate of the acid-decomposable group by the first acid is defined as k0 and a decomposition reaction rate of the acid-decomposable group by the second acid is defined as k′0, k′0/k0 is more than 0.05 and 0.90 or less,
provided that k0 and k′0 are determined as follows:
an actinic ray-sensitive or radiation-sensitive resin film having a film thickness T formed by applying an actinic ray-sensitive or radiation-sensitive resin composition including the resin, a test acid generator A which is an onium salt including an anion of the first acid and a triphenylsulfonium cation, and a solvent onto a substrate is subjected to exposure at 99 positions while increasing an exposure dose from 1 mJ/cm2 with an interval of 0.3 mJ/cm2 using an ArF excimer laser, the film after the exposure is subjected to a baking treatment at 90° C. for 60 seconds, and the film thickness after the exposure treatment is calculated; thereafter, the film is subjected to a development treatment with butyl acetate for 30 seconds and the film thickness of the film after the development treatment at each exposed position is calculated; points corresponding to the film thickness and the exposure dose after the development treatment at each exposed position are plotted in an orthogonal coordinate having the film thicknesses on the vertical axis and the exposure doses on the horizontal axis, a line obtained by connecting the plotted points is created, and coordinates E0.4 and E0.8 on the horizontal axis at points where the vertical axes on the line become Film thickness T×0.4 and Film thickness T×0.8, respectively, are each calculated; next, points corresponding to the film thickness and the exposure dose after the exposure treatment at each exposed position are plotted in an orthogonal coordinate having the film thicknesses on the vertical axis and the exposure doses on the horizontal axis, a line obtained by connecting the plotted points is created, and an absolute value of an inclination of a straight line obtained by connecting points at which the horizontal axes on the line become E0.4 and E0.8, respectively, is taken as k0; and
next, k′0 is determined by the same calculation method as k0 using an actinic ray-sensitive or radiation-sensitive resin film having a film thickness T formed by applying an actinic ray-sensitive or radiation-sensitive resin composition including the resin, a test acid generator B which is an onium salt including an anion of the second acid and a triphenylsulfonium cation, and a solvent onto a substrate, and k′0/k0 is calculated.

### Claim 2 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1,
wherein a pKa of the first acid is −3.50 or more.

### Claim 3 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1,
wherein a molecular weight of the second acid is 250 or more.

### Claim 4 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1,
wherein the acid generator A and the acid generator B have a cation structure containing a sulfonium ion.

### Claim 5 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1,
wherein at least one of the acid generator A or the acid generator B is a compound represented by General Formula (ZI-3),
in General Formula (ZI-3), R1 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or an alkenyl group, R2 and R3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an aryl group, and Rx and Ry each independently represent an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a 2-oxoalkyl group, a 2-oxocycloalkyl group, an alkoxycarbonylalkyl group, an alkoxycarbonylcycloalkyl group, an allyl group, or a vinyl group;
R2 and R3 may be linked to each other to form a ring, and R1 and R2 may be linked to each other to form a ring, Rx and Ry may be linked to each other to form a ring, and a ring structure formed by mutual linking of Rx and Ry may include an oxygen atom, a nitrogen atom, a sulfur atom, a ketone group, an ether bond, an ester bond, or an amide bond; and
Z− represents an anion.

### Claim 6 (depends on 1)

A resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1.

### Claim 7 (depends on 1)

A pattern forming method comprising:
forming a resist film using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1;
exposing the resist film; and
developing the exposed resist film using a developer.

### Claim 8 (depends on 7)

A method for manufacturing an electronic device, comprising the pattern forming method according to claim 7.