# US 2021/0240078 A1 · Photo-decomposable compound, photoresist composition including the same, and method of manufacturing integrated circuit device

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- Number: US 2021/0240078 A1
- Document ID: US20210240078A1
- Status: Published application
- Kind: A1
- Application number: 17/005,636
- Filed: 2020-08-28
- Published: 2021-08-05
- Earliest claimed: 2020-01-29
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Sumin KIM; Hyunwoo KIM; Sukkoo HONG; Yechan KIM; Juyoung KIM; Jinjoo KIM; Juhyeon PARK; Hyunji SONG; Songse YI
- Web page: https://patentgrep.com/patent/US20210240078A1

## CPC

- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- C07C 309/12: containing esterified hydroxy groups bound to the carbon skeleton
- C07C 381/12: Sulfonium compounds
- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- C07C 2601/08: the ring being saturated
- C07C 2603/74: Adamantanes
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- 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
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A photo-decomposable compound includes an anion component including an adamantyl group and a cation component including a C5 to C40 cyclic hydrocarbon group and forming a complex with the anion component. At least one of the adamantyl group and the cyclic hydrocarbon group has a substituent, which decomposes by acid and generates an alkali soluble group. The substituent includes an acid-labile protecting group. A photoresist composition includes a chemically amplified polymer, the photo-decomposable compound, and a solvent. To manufacture an integrated circuit (IC) device, a photoresist film is formed using the photoresist composition on a feature layer, a first area of the photoresist film is exposed to generate a plurality of acids from the photo-decomposable compound in the first area, the chemically amplified polymer is deprotected due to the plurality of acids, and the first area is removed to form a photoresist pattern.

## Claims

### Claim 1

A photo-decomposable compound, comprising:
an anion component including an adamantyl group; and
a cation component including a C5 to C40 cyclic hydrocarbon group, the cation component forming a complex with the anion component,
wherein:
at least one of the adamantyl group and the C5 to C40 cyclic hydrocarbon group has a substituent,
the substituent decomposes in response to exposure to an acid to generate an alkali soluble group, and
the substituent includes an acid-labile protecting group.

### Claim 2 (depends on 1)

The photo-decomposable compound as claimed in claim 1, wherein the acid-labile protecting group is a substituted or unsubstituted t-butyl group or a C3 to C30 substituted or unsubstituted tertiary alicyclic group.

### Claim 3 (depends on 1)

The photo-decomposable compound as claimed in claim 1, wherein:
the acid-labile protecting group includes a first substituent,
the first substituent includes a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a halogen atom, a C1 to C10 halogenated alkyl group, a hydroxyl group, an unsubstituted C6 to C30 aryl group, or a C6 to C30 aryl group,
at least one carbon atom included in the first substituent is substituted with a halogen atom or a heteroatom-containing group.

### Claim 4 (depends on 1)

The photo-decomposable compound as claimed in claim 1, wherein:
the substituent has one of the following structures:
—C(═O)OR1
*—OC(═O)OR1
*—OAc,
in which:
R1 is the acid-labile protecting group and includes a substituted or unsubstituted t-butyl group and a C3 to C30 substituted or unsubstituted tertiary alicyclic group,
Ac is an acetal protecting group, and
* indicates a bonding site.

### Claim 5 (depends on 4)

The photo-decomposable compound as claimed in claim 4, wherein:
R1 is a C3 to C30 substituted or unsubstituted tertiary alicyclic group, and
the C3 to C30 substituted or unsubstituted tertiary alicyclic group includes an alicyclic hydrocarbon group, which includes a group in which two hydrogen atoms are excluded from a C3 to C6 monocycloalkane.

### Claim 6 (depends on 4)

The photo-decomposable compound as claimed in claim 4, wherein:
R1 is a C3 to C30 substituted or unsubstituted tertiary alicyclic group, and
the C3 to C30 substituted or unsubstituted tertiary alicyclic group includes an alicyclic hydrocarbon group, which includes a group in which two hydrogen atoms are excluded from a C7 to C12 polycycloalkane.

### Claim 7 (depends on 1)

The photo-decomposable compound as claimed in claim 1, wherein:
the substituent is connected to the adamantyl group,
the photo-decomposable compound is represented by Formula 1,
in Formula 1,
Ra is the substituent, and is represented by *—C(═O)OR1, in which R1 is the acid-labile protecting group and includes a substituted or unsubstituted t-butyl or a C3 to C30 substituted or unsubstituted tertiary alicyclic group,
Ya is a C1 to C20 divalent linear or cyclic hydrocarbon group,
m is an integer of 1 to 5,
M− is —SO3− or —CO2−, and
A+ is the cation component.

### Claim 8 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein R1 is one of the following structures:
in which * indicates a bonding site.

### Claim 9 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein R1 is one of the following structures:
in which * indicates a bonding site.

### Claim 10 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein R1 is one of the following structures:
in which * indicates a bonding site.

### Claim 11 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein R1 is one of the following structures:
in which * indicates a bonding site.

### Claim 12 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein R1 is one of the following structures:
in which * indicates a bonding site.

### Claim 13 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein R1 is one of the following structures:
wherein * indicates a bonding site.

### Claim 14 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein Ya is a C1 to C5 substituted or unsubstituted alkylene group, a C5 to C20 divalent monocyclic or condensed alicyclic hydrocarbon group, or a C5 to C20 divalent monocyclic or condensed aromatic hydrocarbon group.

### Claim 15

(canceled)

### Claim 16 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein Ya is one of the following structures:
in which:
* indicates a bonding site,
r is an integer of 0 to 2, and
RY1, RY2, RY3, and RY4 are each independently a C1 to C10 linear or branched alkyl group, a cyclopropyl group, a cyclopentyl group, or a cyclohexyl group.

### Claim 17

(canceled)

### Claim 18 (depends on 7)

The photo-decomposable compound as claimed in claim 7, wherein A+ has the following structure:
in which:
each R11 is *—OC(═O)—(CF2)kCF3, in which k is an integer of 0 to 10 and * indicates a bonding site, and
n1, n2, and n3 are each independently an integer of 0 to 2, at least one of n1, n2, and n3 being 1 or 2.

### Claim 19 (depends on 1)

The photo-decomposable compound as claimed in claim 1, wherein:
the substituent is connected to the cyclic hydrocarbon group,
the photo-decomposable compound is represented by Formula 2:
in Formula 2,
Rb is the substituent, and is represented by *—C(═O)OR1, in which R1 is the acid-labile protecting group and includes a substituted or unsubstituted t-butyl or a C3 to C30 substituted or unsubstituted tertiary alicyclic group,
Ya is a C1 to C20 divalent linear or cyclic hydrocarbon group,
m is an integer of 1 to 5,
n1, n2, and n3 are each independently an integer of 0 to 2, at least one of n1, n2, and n3 being 1 or 2,
Rc is a C1 to C10 alkyl group, a C1 to C10 alkoxy group, a halogen atom, a C1 to C10 halogenated alkyl group, a hydroxyl group, an unsubstituted C6 to C30 aryl group, or a C6 to C30 aryl group in which at least one carbon atom included in Rc is substituted with a halogen atom or a heteroatom-containing group,
p is an integer of 0 to 2, and
M− is —SO3− or —CO2−.

### Claim 20 (depends on 1)

The photo-decomposable compound as claimed in claim 1, wherein:
the substituent is connected to each of the adamantyl group and the cyclic hydrocarbon group,
the photo-decomposable compound is represented by Formula 3:
in Formula 3,
each of Rb and Rd is the substituent, and is represented by *—C(═O)OR1, in which R1 is the acid-labile protecting group and includes a substituted or unsubstituted t-butyl or a C3 to C30 substituted or unsubstituted tertiary alicyclic group,
Ya is a C1 to C20 divalent linear or cyclic hydrocarbon group,
m is an integer of 1 to 5,
n1, n2, and n3 are each independently an integer of 0 to 2, at least one of n1, n2, and n3 being 1 or 2,
q is 1 or 2, and
M− is —SO3− or —CO2−.

### Claim 21

A photoresist composition, comprising:
a chemically amplified polymer;
a solvent; and
a photo-decomposable compound that includes an anion component including an adamantyl group and a cation component including a C5 to C40 cyclic hydrocarbon group, the cation component forming a complex with the anion component, wherein:
at least one of the adamantyl group and the C5 to C40 cyclic hydrocarbon group has a substituent that decomposes by an action of acid and generates an alkali soluble group, and
the substituent includes an acid-labile protecting group.

### Claim at position 22

22-33. (canceled)

### Claim 34

A method of manufacturing an integrated circuit (IC) device, the method comprising:
providing a substrate that includes a feature layer;
forming a photoresist film on the feature layer, wherein:
the photoresist film includes a chemically amplified polymer, a photo-decomposable compound, and a solvent,
the photo-decomposable compound has an anion component including an adamantyl group and a cation component including a C5 to C40 cyclic hydrocarbon group and forming a complex with the anion component,
at least one of the adamantyl group and the C5 to C40 cyclic hydrocarbon group has a substituent,
the substituent decomposes in response to an acid to generate an alkali soluble group, and
the substituent includes an acid-labile protecting group;
exposing a first area of the photoresist film to generate a plurality of acids from the photo-decomposable compound in the first area, and deprotecting the chemically amplified polymer due to the plurality of acids, the first area being a portion of the photoresist film;
removing the exposed first area of the photoresist film using a developer to form a photoresist pattern, the photoresist pattern including a non-exposed area of the photoresist film; and
processing the feature layer using the photoresist pattern.

### Claim at position 24

35-40. (canceled)