US-12619147-B2 - Actinic ray-sensitive or radiation-sensitive resin composition, actinic ray-sensitive or radiation-sensitive film, pattern forming method, and method for manufacturing electronic device

US12619147B2US 12619147 B2US12619147 B2US 12619147B2US-12619147-B2

Abstract

An actinic ray-sensitive or radiation-sensitive resin composition containing (A) an acid-decomposable resin, (B) a compound represented by General Formula (b1), and (C) a compound represented by General Formula (c1), in which a ratio of a content of the compound (C) to a content of the compound (B) is from 0.01% by mass to 10% by mass. In the formulae, L represents a single bond or a divalent linking group. A represents a group that decomposes by the action of an acid. B represents a group that decomposes by the action of an acid, a hydroxy group, or a carboxy group. It should be noted that at least one B represents the hydroxy group or the carboxy group. n represents an integer from 1 to 5. X represents an (n+1)-valent linking group. M + represents a sulfonium ion or an iodonium ion.

Inventors

Taro MIYOSHI
Yasunori Yonekuta
Eiji Fukuzaki
Toshiya Takahashi

Assignees

FUJIFILM CORPORATION

Dates

Publication Date: 20260505
Application Date: 20220310
Priority Date: 20190930

Claims (15)

1 . An actinic ray-sensitive or radiation-sensitive resin composition comprising: (A) a resin having a group having a polarity that increases through decomposition by an action of an acid; (B) a compound represented by General Formula (b1), which generates an acid upon irradiation with actinic rays or radiation; and (C) a compound represented by General Formula (c1), which generates an acid upon irradiation with actinic rays or radiation, wherein a ratio of a content of the compound (C) to a content of the compound (B) is from 0.01% by mass to 10% by mass, in General Formula (b1), L represents a single bond or a divalent linking group, in a case where there are a plurality of L's, the plurality of L's may be the same as or different from each other, A represents a group that decomposes by an action of an acid, in a case where there are a plurality of A's, the plurality of A's may be the same as or different from each other, n represents an integer from 1 to 5, X represents an (n+1)-valent linking group, and M + represents a sulfonium ion or an iodonium ion, in General Formula (c1), L represents a single bond or a divalent linking group, in a case where there are a plurality of L's, the plurality of L's may be the same as or different from each other, n represents an integer from 1 to 5, X represents an (n+1)-valent linking group, M + represents a sulfonium ion or an iodonium ion, provided that L, n, X, and M + in General Formula (c1) are the same as L, n, X, and M + in General Formula (b1), respectively, and B in General Formula (c1) is different from A in General Formula (b1), B represents a group that decomposes by an action of an acid, a hydroxy group, or a carboxy group, and in a case where there are a plurality of B's, the plurality of B's may be the same as or different from each other, provided that at least one B represents the hydroxy group or the carboxy group, wherein the hydroxy group or the carboxy group of the at least one B in General Formula (c1) is disposed on a terminal site of the General Formula (c1).
2 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the compound (B) is represented by General Formula (b2) and the compound (C) is represented by General Formula (c2), in General Formula (b2), L represents a single bond or a divalent linking group, in a case where there are a plurality of L's, the plurality of L's may be the same as or different from each other, A represents a group that decomposes by an action of an acid, in a case where there are a plurality of A's, the plurality of A's may be the same as or different from each other, n represents an integer from 1 to 5, and M + represents a sulfonium ion or an iodonium ion, in General Formula (c2), L represents a single bond or a divalent linking group, in a case where there are a plurality of L's, the plurality of L's may be the same as or different from each other, n represents an integer from 1 to 5, M + represents a sulfonium ion or an iodonium ion, provided that L, n, and M + in General Formula (c2) are the same as L, n, and M + in General Formula (b2), respectively, B represents a group that decomposes by an action of an acid, a hydroxy group, or a carboxy group, and in a case where there are a plurality of B's, the plurality of B's may be the same as or different from each other, provided that at least one B represents the hydroxy group or the carboxy group.
3 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the compound (B) is represented by General Formula (b3) and the compound (C) is represented by General Formula (c3), in General Formula (b3), L represents a single bond or a divalent linking group, in a case where there are a plurality of L's, the plurality of L's may be the same as or different from each other, A represents a group that decomposes by an action of an acid, in a case where there are a plurality of A's, the plurality of A's may be the same as or different from each other, o, p, and q each independently represent an integer from 0 to 5, provided that a sum of o, p, and q is from 1 to 5, and M + represents a sulfonium ion or an iodonium ion, in General Formula (c3), L represents a single bond or a divalent linking group, in a case where there are a plurality of L's, the plurality of L's may be the same as or different from each other, o, p, and q each independently represent an integer from 0 to 5, provided that a sum of o, p, and q is from 1 to 5, M + represents a sulfonium ion or an iodonium ion, provided that L, o, p, q, and M + in General Formula (c3) are the same as L, o, p, q, and M + in General Formula (b3), respectively, B represents a group that decomposes by an action of an acid, a hydroxy group, or a carboxy group, and in a case where there are a plurality of B's, the plurality of B's may be the same as or different from each other, provided that at least one B represents the hydroxy group or the carboxy group.
4 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the group represented by A, which decomposes by an action of an acid, is at least one group selected from the group consisting of a group represented by General Formula (T-1) and a group represented by General Formula (T-2), in General Formula (T-1), R 11 represents a hydrogen atom or an alkyl group, R 12 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and the alkyl group and the cycloalkyl group may each include an ether bond or a carbonyl bond, R 13 represents an alkyl group, a cycloalkyl group, or an aryl group, and the alkyl group and the cycloalkyl group may each include an ether bond or a carbonyl bond, R 11 and R 12 may be bonded to each other to form a ring, R 12 and R 13 may be bonded to each other to form a ring, and * represents a bond, and in General Formula (T-2), R 21 , R 22 , and R 23 each independently represent an alkyl group, two of R 21 to R 23 may be bonded to each other to form a ring, and * represents a bond.
5 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 4 , wherein the group represented by A, which decomposes by an action of an acid, is the group represented by General Formula (T-1).
6 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the ratio of the content of the compound (C) to the content of the compound (B) is from 0.01% by mass to 5% by mass.
7 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the sulfonium ion or the iodonium ion represented by M + has no nitrogen atom.
8 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the resin (A) includes a repeating unit represented by General Formula (I), in General Formula (I), R 41 , R 42 , and R 43 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, provided that R 42 may be bonded to Ar 4 to form a ring, and in this case, R 42 represents a single bond or an alkylene group, X 4 represents a single bond, —COO—, or —CONR 64 —, where R 64 represents a hydrogen atom or an alkyl group, L 4 represents a single bond or an alkylene group, Ar 4 represents an (n+1)-valent aromatic ring group, and in a case where Ar 4 is bonded to R 42 to form a ring, Ar 4 represents an (n+2)-valent aromatic ring group, and n represents an integer of 1 to 5.
9 . An actinic ray-sensitive or radiation-sensitive film formed of the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 .
10 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising an acid diffusion control agent.
11 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein the acid diffusion control agent has an onium salt (DC) which is a weak acid relative to a photoacid generator.
12 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 11 , wherein the onium salt (DC) is a compound represented by general formulas (d1-1) to (d1-3), in the formulae, R 51 is a hydrocarbon group which may have a substituent, Z 2c is a hydrocarbon group having 1 to 30 carbon atoms, which may have a substituent (provided that carbon adjacent to S is not substituted with a fluorine atom), R 52 is an organic group, Y 3 is a linear, branched, or cyclic alkylene group or an arylene group, Rf is a hydrocarbon group including a fluorine atom, and M + 's are each independently an ammonium cation, a sulfonium cation, or an iodonium cation.
13 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising a fluorine-containing compound having a group having a solubility in an alkali developer that increases upon decomposition by the action of the alkali developer.
14 . A pattern forming method comprising: a resist film forming step of forming a resist film using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ; an exposing step of exposing the resist film; and a developing step of developing the exposed resist film, using a developer.
15 . A method for manufacturing an electronic device, comprising the pattern forming method according to claim 14 .

Description

CROSS REFERENCE TO RELATED APPLICATIONS This is a continuation of International Application No. PCT/JP2020/034762 filed on Sep. 14, 2020 and claims priority from Japanese Patent Application No. JP2019-179944 filed on Sep. 30, 2019 and Japanese patent application No. 2020-094650 filed on May 29, 2020, the entire contents of which are incorporated herein by reference. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an actinic ray-sensitive or radiation-sensitive resin composition, an actinic ray-sensitive or radiation-sensitive film, a pattern forming method, and a method for manufacturing an electronic device. More specifically, the present invention relates to an actinic ray-sensitive or radiation-sensitive resin composition, an actinic ray-sensitive or radiation-sensitive film, a pattern forming method, and a method for manufacturing an electronic device, each of which is suitably used for an ultra-microlithography process applicable to a process for manufacturing an ultra-large scale integration (LSI) and a high-capacity microchip, a process for creating a mold for a nanoimprint, a process for manufacturing a high-density information recording medium, and the like, and other photofabrication processes. 2. Description of the Related Art In processes for manufacturing semiconductor devices such as an integrated circuit (IC) and an LSI, microfabrication by lithography using a photoresist composition has been performed in the related art. In recent years, along with the high integration of integrated circuits, the formation of ultrafine patterns in a submicron region or quarter micron region has been required. Along with this, the exposure wavelength also tends to be shortened from g-line to i-line, and further to KrF excimer laser light, and an exposure machine using an ArF excimer laser having a wavelength of 193 nm as a light source is currently being developed. In addition, the development of a so-called liquid immersion method in which a liquid having a high refractive index (hereinafter also referred to as an “immersion liquid”) is filled between a projection lens and a sample as a technique for further enhancing a resolving power has been in progress since the related art. Furthermore, at present, the development of lithography using electron beams (EB), X-rays, extreme ultraviolet rays (EUV), or the like in addition to excimer laser light is also in progress. Along with this, resist compositions which are effectively sensitive to various actinic rays or radiations have been developed. For example, a resist composition containing a resin having an acid-decomposable group, a salt consisting of a specific cation and a specific anion having an acid-decomposable group as an acid generator, and a salt consisting of a specific cation and a specific anion, which are each different from the cation and the anion in the salt, is described in JP2013-41257A. SUMMARY OF THE INVENTION However, in recent years, performance required for a resist composition has been further enhanced due to further miniaturization of a pattern formed, and the like. In view of the circumstances, an object of the present invention is to provide an actinic ray-sensitive or radiation-sensitive resin composition which is excellent in a resolution and a line width roughness (LWR) performance and can reduce development defects and etching defects; and an actinic ray-sensitive or radiation-sensitive film, a pattern forming method, and a method for manufacturing an electronic device, each using the actinic ray-sensitive or radiation-sensitive resin composition. The present inventors have found that the object can be accomplished by the following configurations. [1] An actinic ray-sensitive or radiation-sensitive resin composition comprising: (A) a resin having a group having a polarity that increases through decomposition by an action of an acid;(B) a compound represented by General Formula (b1), which generates an acid upon irradiation with actinic rays or radiation; and(C) a compound represented by General Formula (c1), which generates an acid upon irradiation with actinic rays or radiation,in which a ratio of a content of the compound (C) to a content of the compound (B) is from 0.01% by mass to 10% by mass. In General Formula (b1), L represents a single bond or a divalent linking group. In a case where there are a plurality of L's, the plurality of L's may be the same as or different from each other. A represents a group that decomposes by an action of an acid. In a case where there are a plurality of A's, the plurality of A's may be the same as or different from each other. n represents an integer from 1 to 5. X represents an (n+1)-valent linking group. M+ represents a sulfonium ion or an iodonium ion. In General Formula (c1), L represents a single bond or a divalent linking group. In a case where there are a plurality of L's, the plurality of L's may be the same as or different from each other. n rep