# US 2024/0199540 A1 · Carboxylate salt, photoresist composition including the same, and method of forming pattern using the photoresist composition

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- Number: US 2024/0199540 A1
- Document ID: US20240199540A1
- Status: Published application
- Kind: A1
- Application number: 18/312,825
- Filed: 2023-05-05
- Published: 2024-06-20
- Earliest claimed: 2022-11-30
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Hoyoon PARK; Hana KIM; Kyuhyun IM; Haengdeog KOH; Yoonhyun KWAK; Hyeran KIM; Changheon LEE
- Web page: https://patentgrep.com/patent/US20240199540A1

## CPC

- C07C 323/09: having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C 311/08: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C 311/21: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- G03F 7/0042: {with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists (G03F7/075 takes precedence)}
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/2004: {characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light}
- G03F 7/2059: {using a scanning corpuscular radiation beam, e.g. an electron beam}
- C07C 2601/16: the ring being unsaturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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)

## Abstract

Provided are a carboxylate salt represented by Formula 1, a photoresist composition including the same, and a pattern forming method using the same: wherein A11, L11, L12, a11, a12, R11 to R13, b13, n11, n12, and M+ in Formula 1 are defined as described in the specification.

## Claims

### Claim 1

A carboxylate salt represented by Formula 1:
wherein, in Formula 1,
A11 is a C1-C30 cyclic hydrocarbon group that optionally includes a heteroatom,
L11 and L12 are each independently a single bond or a divalent linking group,
a11 and a12 are each independently an integer from 0 to 4,
R11 to R13 are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxy group, a linear, branched, or cyclic C1-C20 monovalent hydrocarbon group that optionally includes a heteroatom, or —N(Q1)(Q2),
Q1 and Q2 are each independently hydrogen, deuterium, a linear, branched, or cyclic C1-C20 monovalent hydrocarbon group that optionally includes a heteroatom,
b13 is an integer from 0 to 10,
an adjacent two of R11, R12, R13, L11, and L12 are optionally bonded to each other to form a ring,
an adjacent two of a plurality of R13 are optionally bonded to each other to form a ring,
n11 and n12 are each independently an integer from 1 to 10, and
M+ is a counter cation.

### Claim 2 (depends on 1)

The carboxylate salt of claim 1, wherein A11 is a C3-C20 cycloalkyl group, a C3-C20 heterocycloalkyl group, a C3-C20 cycloalkenyl group, a C3-C20 heterocycloalkenyl group, a C6-C20 aryl group, or a C1-C20 heteroaryl group.

### Claim 3 (depends on 1)

The carboxylate salt of claim 1, wherein L11 and L12 are each independently a single bond, O, C(═O), C(═O)O, OC(═O), C(═O)NH, NHC(═O), a linear, branched, or cyclic C1-C30 divalent hydrocarbon group that optionally includes a heteroatom.

### Claim 4 (depends on 1)

The carboxylate salt of claim 1, wherein
a11 is 0.

### Claim 5 (depends on 1)

The carboxylate salt of claim 1, wherein R12 is hydrogen or deuterium.

### Claim 6 (depends on 1)

The carboxylate salt of claim 1, wherein n11 and n12 are each independently 1 or 2.

### Claim 7 (depends on 1)

The carboxylate salt of claim 1, wherein
M+ is a substituted or unsubstituted sulfonium cation, a substituted or unsubstituted iodonium cation, or a substituted or unsubstituted ammonium cation.

### Claim 8 (depends on 1)

The carboxylate salt of claim 1, wherein M+ is represented by any one of Formulae 2-1 to 2-3:
wherein, in Formulae 2-1 to 2-3,
R21 to R24 are each independently a linear, branched, or cyclic C1-C30 monovalent hydrocarbon group that optionally includes a heteroatom, and
an adjacent two of R21 to R24 are optionally bonded to each other to form a ring.

### Claim 9 (depends on 1)

The carboxylate salt of claim 1, wherein M+ is represented by any one of Formulae 2-11 to 2-13:
wherein, in Formulae 2-11 to 2-13,
R21a to R21e are each independently hydrogen, deuterium, a halogen, a cyano group, a hydroxy group, a linear, branched, or cyclic C1-C20 monovalent hydrocarbon group that optionally includes a heteroatom,
R22 to R24 are each independently a linear, branched, or cyclic C1-C30 monovalent hydrocarbon group that optionally includes a heteroatom, and
an adjacent two of R21a to R21e and R22 to R24 are optionally bonded to each other to form a ring.

### Claim 10 (depends on 1)

The carboxylate salt of claim 1, wherein M+ is selected from any structure represented in Group II:

### Claim 11 (depends on 1)

The carboxylate salt of claim 1, wherein
the carboxylate salt represented by Formula 1 is represented by one of Formulae 1-1 to 1-3:
where, in Formulae 1-1 to 1-3,
X11 to X14 are each any atom,
the respective indicates a single bond or a double bond,
A11, L11, a11, M+, R13, n11, and b13 are defined the same as A11, L11, a11, M+, R13, n11, and b13 in Formula 1,
R11a and R11b are each defined the same as R11 in Formula 1,
R12a and R12b are each defined the same as R12 in Formula 1,
L12a and L12b are each defined the same as L12 in Formula 1, and
a12a and a12b are each defined the same as a12 in Formula 1.

### Claim 12 (depends on 1)

The carboxylate salt of claim 1, wherein the carboxylate salt represented by Formula 1 is represented by any one of Formulae 1-11 to 1-15:
wherein, in Formulae 1-11 to 1-15,
X11 to X16 are each any atom,
the respective indicates a single bond or a double bond,
A11, L11, L12, a11, a12, M+, R11 to R13, n11, n12, and b13 are defined the same as A11, L11, L12, a11, a12, M+, R11 to R13, n11, n12, and b13 in Formula 1,
R11a and R11b are each defined the same as R11 in Formula 1,
R12a and R12b are each defined the same as R12 in Formula 1,
L12a and L12b are each defined the same as L12 in Formula 1, and
a12a and a12b are each defined the same as a12 in Formula 1.

### Claim 13 (depends on 1)

The carboxylate salt of claim 1, wherein the carboxylate salt represented by Formula 1 is selected from any salt represented in Group I:
wherein, in Group I,
M+ is a counter cation.

### Claim 14 (depends on 1)

A photoresist composition comprising:
the carboxylate salt of claim 1; an organic solvent; and
a base resin.

### Claim 15 (depends on 14)

The photoresist composition of claim 14, further comprising:
a photoacid generator,
wherein the carboxylate salt is a photodegradable compound that is configured to generate an acid by being exposed to light exposure and act as a quenching base for neutralizing an acid before light exposure. 16 The photoresist composition of claim 14, wherein the carboxylate salt is a photodegradable compound that is configured to generate an acid by being exposed to light exposure.

### Claim 17 (depends on 16)

The photoresist composition of claim 16, further comprising:
a quencher.

### Claim 18 (depends on 14)

The photoresist composition of claim 14, wherein
an amount of the carboxylic acid is in a range of 0.1 parts by weight to 40 parts by weight based on 100 parts by weight of the base resin.

### Claim 19 (depends on 14)

A method of forming a pattern, the method comprising:
forming a photoresist film by applying the photoresist composition of claim 14 on a substrate;
exposing at least a portion of the photoresist film to high energy rays to provide an exposed photoresist film; and
developing the exposed photoresist film using a developing solution.

### Claim 20 (depends on 19)

The method of claim 19, wherein the exposing is performed by irradiating ultraviolet (UV) rays, deep ultraviolet (DUV) rays, extreme ultraviolet (EUV) rays, and/or electron beam (EB) rays.