# US 2024/0201588 A1 · Organic salt, photoresist composition including the same, and pattern formation method using the same

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- Number: US 2024/0201588 A1
- Document ID: US20240201588A1
- Status: Published application
- Kind: A1
- Application number: 18/192,316
- Filed: 2023-03-29
- Published: 2024-06-20
- Earliest claimed: 2022-11-11
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Hana KIM; Beomseok KIM; Kyuhyun IM; Yoonhyun KWAK; Hyeran KIM
- Web page: https://patentgrep.com/patent/US20240201588A1

## CPC

- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- C07C 65/10: Salicylic acid
- C07C 69/84: of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C 309/12: containing esterified hydroxy groups bound to the carbon skeleton
- C07C 311/09: the carbon skeleton being further substituted by at least two halogen atoms
- C07C 391/02: having selenium atoms bound to carbon atoms of six-membered aromatic rings
- C07C 395/00: Compounds containing tellurium
- G03F 7/0382: {the macromolecular compound being present in a chemically amplified negative photoresist composition}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- C07C 2603/74: Adamantanes
- Y02E 10/549: Organic PV cells
- 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
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Provided are an organic salt represented by Formula 1, a photoresist composition including the same, and a pattern method using the same: wherein X+, Y−, and R11 to R13 in Formula 1 are understood by referring to the specification.

## Claims

### Claim 1

An organic salt represented by Formula 1:
wherein, in Formula 1,
X+ is Se+ or Te+;
R11 to R13 are each independently a linear, branched, or cyclic C1-C20 monovalent hydrocarbon group which optionally includes a heteroatom;
at least one of R11 to R13 includes at least one iodine (I);
adjacent two of R11 to R13 are optionally bonded to each other to form a ring; and
Y− is a counter anion.

### Claim 2 (depends on 1)

The organic salt of claim 1, wherein
X+ is Te+.

### Claim 3 (depends on 1)

The organic salt of claim 1, wherein
R11 to R13 are each independently a C1-C20 alkyl group, a C3-C20 cycloalkyl group, or a C6-C20 aryl group, and
R11 to R13 are each independently unsubstituted or substituted with deuterium, halogen, a cyano group, a hydroxyl group, a carboxyl group, an ester moiety, an ester sulfate moiety, a carbonate moiety, a lactone moiety, a sultone moiety, a carboxylic anhydride moiety, a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C1-C20 alkoxy group, a C3-C20 cycloalkyl group, a C6-C20 aryl group, or a combination thereof.

### Claim 4 (depends on 1)

The organic salt of claim 1, wherein
at least one of R11 to R13 is a C6-C20 aryl group substituted with at least one I.

### Claim 5 (depends on 1)

The organic salt of claim 1, wherein
only one of R11, R12, or R13 includes at least one I;
R11 and R12 each include at least one I, and R13 does not include I; or
R11 to R13 each include at least one I.

### Claim 6 (depends on 1)

The organic salt of claim 1, wherein
the organic salt includes one I, two I, or three I.

### Claim 7 (depends on 1)

The organic salt of claim 1, wherein
the organic salt is represented by Formula 1-1:
wherein, in Formula 1-1,
R11a to R11e are each independently hydrogen, halogen, or a linear, branched, or cyclic C1-C20 monovalent hydrocarbon group which optionally includes a heteroatom,
at least one of R11a to R11e, R12, and R13 includes at least one I, and
adjacent two of R11a to R11e, R12, and R13 are optionally bonded to each other to form a ring.

### Claim 8 (depends on 7)

The organic salt of claim 7, wherein
at least one of R11a to R11e is I.

### Claim 9 (depends on 1)

The organic salt of claim 1, wherein
the organic salt is represented by Formula 1-11 or Formula 1-12:
wherein, in Formulae 1-11 and 1-12,
R11a to R11e, R12a to R12e, and R13a to R13e are each independently: hydrogen; halogen; or a linear, branched or cyclic C1-C20 monovalent hydrocarbon group which optionally includes a heteroatom,
at least one of Rii a to Rule is I,
b12a and b13a are each an integer from 1 to 4,
A11 and Au are each absent or a benzene ring,
L11 is a single bond, O, S, CO, SO, SO2, CRR′, or NR,
R and R′ are each independently hydrogen, deuterium, halogen, a hydroxyl group, a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C1-C20 alkoxy group, a C3-C20 cycloalkyl group, or a C3-C20 cycloalkoxy group, and
adjacent two of R11a to R11e, R12a to R12e, and R13a to R13e are optionally linked to each other to form a condensed ring.

### Claim 10 (depends on 1)

The organic salt of claim 1, wherein
Y− is represented by at least one of Formulae 2-1 to 2-4:
wherein, in Formulae 2-1 to 2-4,
L21 to L23 are each independently a single bond or CRR′,
R and R′ are each independently hydrogen, deuterium, halogen, a hydroxyl group, a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C1-C20 alkoxy group, a C3-C20 cycloalkyl group, or a C3-C20 cycloalkoxy group,
n21 to n23 are each independently 1, 2, or 3,
x21 and x22 are each independently 0 or 1, and
R21 to R23 are each independently: hydrogen; halogen; or a linear, branched, or cyclic C1-C20 monovalent hydrocarbon group which optionally includes a heteroatom.

### Claim 11 (depends on 1)

The organic salt of claim 1, wherein
Y− is represented by one of Formulae 2-21 to 2-23:
wherein, in Formulae 2-21 to 2-23,
L21 and L22 are each independently a single bond or CXaXb,
Xa and Xb are each independently hydrogen, halogen, a C1-C20 alkyl group, or a C1-C20 halogenated alkyl group,
n21 and n22 are each independently 1, 2, or 3,
R21a, R22a, and R21b are each independently: a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a tricyclodecanyl group, a tetracyclododecanyl group, a phenyl group, or a naphthyl group, each unsubstituted or substituted with halogen, a hydroxyl group, a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C3-C20 cycloalkyl group, a C6-C20 aryl group, a C3-C20 heteroaryl group, or a combination thereof.

### Claim 12 (depends on 1)

The organic salt of claim 1, wherein
the organic salt represented by Formula 1 is selected from Group I:

### Claim 13 (depends on 12)

The organic salt of claim 12, wherein
Y− is represented by one of Formulae 2-21 to 2-23:
wherein, in Formulae 2-21 to 2-23,
L21 and L22 are each independently a single bond or CXaXb;
Xa and Xb are each independently hydrogen, halogen, a C1-C20 alkyl group, or a C1-C20 halogenated alkyl group,
n21 and n22 are each independently 1, 2, or 3,
R21a, R22a, and R21b are each independently: a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a tricyclodecanyl group, a tetracyclododecanyl group, a phenyl group, or a naphthyl group, each unsubstituted or substituted with halogen, a hydroxyl group, a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C3-C20 cycloalkyl group, a C6-C20 aryl group, a C3-C20 heteroaryl group, or a combination thereof.

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 14)

The photoresist composition of claim 14, wherein
the organic salt is configured to be a photodegradable compound that generates an acid upon when exposed to light.

### Claim 16 (depends on 14)

The photoresist composition of claim 14, further comprising:
a quencher.

### Claim 17 (depends on 14)

The photoresist composition of claim 14, further comprises:
a photoacid generator configured to generate an acid when exposed to light,
wherein the organic salt is configured to be a photodegradable compound that generates an acid when exposure to light and, before the exposure, to act as a quenching base to neutralize the acids.

### Claim 18 (depends on 14)

The photoresist composition of claim 14, wherein
an amount of the organic salt is about 0.1 parts by weight to about 40 parts by weight based on 100 parts by weight of the base resin.

### Claim 19 (depends on 14)

A pattern formation 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; and
developing an exposed photoresist film using a developing solution.

### Claim 20 (depends on 19)

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