Actinic ray-sensitive or radiation-sensitive resin composition, pattern forming method, and method of manufacturing electronic device

Patent metadata

Field	Value
Publication number	US-11640113-B2
Application number	US-201916368522-A
Country	US
Kind code	B2
Filing date	Mar 28, 2019
Priority date	Sep 29, 2016
Publication date	May 2, 2023
Grant date	May 2, 2023

Abstract

Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin including a repeating unit (a) represented by Formula (1); (B) a compound that generates an acid by irradiation with actinic rays or radiation; and (C) an organic solvent. A concentration of solid contents of the actinic ray-sensitive or radiation-sensitive resin composition is 4 mass % or less. (in the formula, R11 and R12 each independently represent a hydrogen atom, a halogen atom, or a monovalent organic group. R13 represents a hydrogen atom, a halogen atom, or a monovalent organic group or is a single bond or an alkylene group, and is bonded to L or Ar in the formula to form a ring. L represents a single bond or a divalent linking group. Ar represents an aromatic ring group. n represents an integer of 2 or more.)

First claim

What is claimed is:

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:
(A) a resin including a repeating unit (a) represented by Formula (1), a repeating unit (b) represented by Formula (A1-1) below having an acid-decomposable group in which a protective group leaves due to an action of an acid to generate a polar group, and any one of a repeating unit (c) represented by Formula (A2) below or a repeating unit (d) represented by Formula (A3) below;
(B) a compound that generates an acid by irradiation with actinic rays or radiation; and
(C) an organic solvent,
wherein the concentration of solid contents of the composition is 4 mass % or less,
Formula (1) is as follows;

in Formula (1),
R 11 and R 12 each independently represents a hydrogen atom, a halogen atom, or a monovalent organic group,
R 13 represents a hydrogen atom, a halogen atom, or a monovalent organic group or is a single bond or an alkylene group, and is bonded to L or Ar in the formula to form a ring,
L represents a single bond or a divalent linking group,
Ar represents an aromatic ring group, and
n represents an integer of 2 or more,
Formula (A1-1) is as follows:

in Formula (A1-1),
Xa 1 represents a hydrogen atom or an alkyl group,
T represents a single bond or a divalent linking group,
two of Rx 1 , Rx 2 and Rx 3 are bonded to each other to form a cycloalkyl group, and a remaining group represents an alkyl group, a cycloalkyl group, or a phenyl group, and
Rx 1 , Rx 2 , and Rx 3 each only includes carbon atoms and hydrogen atoms, and the total number of carbon atoms included in Rx 1 , Rx 2 , and Rx 3 is 4 to 11, and

Formulas (A2) and (A3) are as follows:

in Formula (A2),
R 61 , R 62 , and R 63 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, here, R 62 may be bonded to Ar 6 or L 6 to form a ring, and R 62 in this case represents a single bond or an alkylene group,
X 6 represents a single bond, —COO—, or —CONR 64 —, and R 64 represents a hydrogen atom or an alkyl group,
L 6 represents a single bond or a divalent linking group, and in a case of forming a ring with R 62 , L 6 represents a trivalent linking group,
Ar 6 represents a (m+1)-valent aromatic ring group, and in a case where Ar 6 is bonded to R 62 to form a ring, Ar 6 represents a (m+2)-valent aromatic ring group,
Y 2 represents a hydrogen atom or a group that leaves by an action of an acid, and in a case where m≥2, a plurality of Y 2 's may be identical to or different from each other, here, at least one of Y 2 's represents a group that leaves due to an action of an acid, and
m represents an integer of 1 to 4,
in Formula (A3),
R 41 , R 42 , and R 43 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, R 42 may be bonded to L 4 to form a ring, and R 42 in this case represents an alkylene group,
X 4 represents a single bond, —COO—, or —CONR 44 —, and R 44 represents a hydrogen atom or an alkyl group,
L 4 represents a single bond or a divalent linking group, and in a case of forming a ring with R 42 , L 4 represents a trivalent linking group,
R 44 and R 45 represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyl group, or a heterocyclic group,
M 4 represents a single bond or a divalent linking group,
Q 4 represents an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, and
at least two of Q 4 , M 4 , or R 44 may be bonded to each other to form a ring.

2. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the resin (A) further contains a repeating unit (e) having a lactone structure.

3. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 2 ,
wherein a repeating unit having a lactone structure represented by Formula (AII) is contained as the repeating unit (e),

in Formula (AII),
Rb 0 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms,
Ab represents a single bond, an alkylene group, a divalent linking group having a monocyclic or polycyclic alicyclic hydrocarbon structure, an ether bond, an ester bond, a carbonyl group, a carboxyl group, or a divalent group obtained by combining these, and
V represents a group represented by any one of Formulae (LC1-1) to (LC1-17),

in Formulae (LC1-1) to (LC1-17),
Rb 2 represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 4 to 7 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, a carboxyl group, a halogen atom, a hydroxyl group, a cyano group, or an acid-decomposable group,
n 2 represents an integer of 0 to 4, and in a case where n 2 is 2 or more, a plurality of Rb 2 's may be identical to or different from each other, and the plurality of Rb 2 's which are present may be bonded to each other to form a ring.

4. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the concentration of solid contents is from 0.3 mass % to 4 mass %.

5. A pattern forming method comprising:
forming actinic ray-sensitive or radiation-sensitive film including the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ;
exposing the actinic ray-sensitive or radiation-sensitive film; and
developing the actinic ray-sensitive or radiation-sensitive film after exposure.

6. The pattern forming method according to claim 5 ,
wherein a film thickness of the actinic ray-sensitive or radiation-sensitive film before exposure is 5 to 80 nm.

7. A method of manufacturing an electronic device comprising:
the pattern forming method according to claim 5 .

8. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein T in Formula (A1-1) is a single bond.

9. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein T in Formula (A1-1) is an arylene group.

10. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,
wherein the compound (B) is represented by Formula (ZI),

in Formula (ZI),
R 201 , R 202 , and R 203 each independently represents an organic group, provided that two of R 201 to R 203 may be bonded to each other to form a ring structure and may contain an oxygen atom, a sulfur atom, an ester bond, an amide bond, or a carbonyl group in the ring, and
Z − represents a non-nucleophilic anion represented by Formula (AN1),

Assignees

• Fujifilm Corp

Inventors

• Tsubaki Hideaki
• Furutani Hajime
• Kaneko Akihiro
• Nihashi Wataru
• Hirano Shuji

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• G03F7/38

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• G03F7/039 Primary

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/0382

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title