Actinic ray-sensitive or radiation-sensitive resin composition, actinic ray-sensitive or radiation-sensitive film, mask blank provided with actinic ray-sensitive or radiation-sensitive film, pattern forming method, method for manufacturing electronic device, electronic device, and compound

Patent metadata

Field	Value
Publication number	US-10011576-B2
Application number	US-201615176810-A
Country	US
Kind code	B2
Filing date	Jun 8, 2016
Priority date	Feb 18, 2014
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

The actinic ray-sensitive or radiation-sensitive resin composition includes a crosslinking agent having a polarity converting group and an alkali-soluble resin, in which the polarity converting group is a group capable of decomposing by the action of an alkaline aqueous solution to generate a carboxylic acid or sulfonic acid on the side having a crosslinking group.

First claim

What is claimed is:

1. An actinic ray-sensitive or radiation-sensitive resin composition, comprising:
a crosslinking agent having a polarity converting group; an alkali-soluble resin; and
a compound capable of generating an acid upon irradiation with actinic rays or radiation,
wherein the polarity converting group is a group capable of decomposing by the action of an alkaline aqueous solution to generate a carboxylic acid or sulfonic acid which is bonded to a structure having the crosslinking group,
wherein the alkali-soluble resin includes a repeating unit represented by the following General Formula (II) and a repeating unit represented by the following General Formula (3A), and
wherein the crosslinking agent is a compound represented by General Formula (1), or a compound in which two to five structures represented by General Formula (1) are connected via a linking group or a single bond represented by L in General Formula (3),

wherein in General Formula (II),
R 2 represents a hydrogen atom, a methyl group which may have a substituent, or a halogen atom,
B′ represents a single bond or a divalent organic group,
Ar′ represents an aromatic ring group, and
m represents an integer of 1 or more,

in General Formula (3A),
R 13 represents a hydrogen atom or a methyl group,
X represents a non-acid-decomposable polycyclic alicyclic hydrocarbon structure bonded directly or via a divalent linking group to the oxygen,
Ar 1 represents an aromatic ring, and
m2 is an integer of 1 or more,

wherein in General Formula (1), R 1 represents a structure represented by any one of General Formulae (4) to (8), or a group containing the structure represented by any one of General Formulae (4) to (8), each of R 2 to R 6 independently represents a hydrogen atom, an organic group having 1 to 50 carbon atoms, or a binding site to a linking group or a single bond represented by L in General Formula (3), provided that at least one of R 2 to R 6 is a structure represented by General Formula (2), and at least one of R 1 to R 6 is a structure represented by any one of General Formulae (4) to (8), or a group containing the structure represented by any one of General Formulae (4) to (8),
in General Formula (2), R 7 represents a hydrogen atom or an organic group having 1 to 30 carbon atoms, and * represents a binding site in any one of R 2 to R 6 , and
in General Formula (3), L represents a linking group or a single bond, * represents a binding site in any one of R 2 to R 6 , and k is an integer of 2 to 5,

wherein in General Formula (4), C1 represents a hydrocarbon group having 1 to 15 carbon atoms and forms a monocyclic or polycyclic ring together with the —COO— group in the formula,
in General Formula (5), C2 represents a hydrocarbon group having 1 to 15 carbon atoms and forms a monocyclic or polycyclic ring together with the —SO 3 — group in the formula,
in General Formula (6), each X 1 independently represents a hydrogen atom or a substituent, R 8 represents an alkyl group or an aryl group, and 1 represents an integer of 0 to 7, provided that in the case where R 8 is an alkyl group, the structure represented by General Formula (6) has at least one electron withdrawing group, and in the case where R 8 in this case is an alkyl group which does not have an electron withdrawing group, 1 is 1 or more, and at least one X 1 is an electron withdrawing group,
in General Formula (7), each X 2 independently represents a hydrogen atom or a substituent, R 9 represents an alkyl group or an aryl group, and m represents an integer of 0 to 7,
in General Formula (8), each X 3 independently represents a hydrogen atom or a substituent, R 10 represents an alkyl group or an aryl group, and n represents an integer of 0 to 7, and
in General Formulae (4) to (8), * represents a binding site.

2. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the linking group L in General Formula (3) is a group selected from an alkylene group, an arylene group, a carboxylic acid ester bond, an ether bond, and combinations thereof.

3. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , wherein the alkali-soluble resin includes at least a repeating unit represented by the following General Formula (12), as the repeating unit represented by General Formula (II),

wherein in General Formula (12),
R 12 represents a hydrogen atom or a methyl group, and
Ar represents an aromatic ring group.

4. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising a basic compound or ammonium salt compound whose basicity is decreased upon irradiation with actinic rays or radiation.

5. An actinic ray-sensitive or radiation-sensitive film comprised of the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 .

6. A mask blank provided with the actinic ray-sensitive or radiation-sensitive film according to claim 5 .

7. A pattern forming method, comprising:
forming the actinic ray-sensitive or radiation-sensitive film according to claim 5 ;
exposing the film; and
developing the exposed film using a developer to form a pattern.

8. The pattern forming method according to claim 7 , wherein the exposure is carried out using X-rays, an electron beam, or EUV.

9. A method for manufacturing an electronic device, comprising the pattern forming method according to claim 7 .

10. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising a resin containing a repeating unit having an acid-crosslinkable group, represented by the following General Formula (1),

wherein in General Formula (1),
R 1 represents a hydrogen atom, a methyl group, or a halogen atom,
R 2 and R 3 represent a hydrogen atom, an alkyl group, or a cycloalkyl group,
L represents a divalent linking group or a single bond,
Y represents a substituent except for a methylol group,
Z represents a hydrogen atom or a substituent,
m represents an integer of 0 to 4,
n represents an integer of 1 to 5, and
m+n is 5 or less.

11. A compound represented by the following General Formula (1), or a compound in which two or three structures represented by General Formula (1) are connected via a linking group or a single bond represented by L in General Formula (3a),

wherein in General Formula (1), R 1 represents a structure represented by General Formula (4), or a group containing the structure represented by General Formula (4), each of R 2 to R 6 independently represents a hydrogen atom, an organic group having 1 to 50 carbon atoms, or a binding site in w

Assignees

• Fujifilm Corp

Inventors

• Yamaguchi Shuhei
• Takahashi Koutarou
• Tsuchimura Tomotaka
• Yokokawa Natsumi
• Mochizuki Hidehiro

Classifications

• C07D307/33 Primary

  in position 2, the oxygen atom being in its keto or unsubstituted enol form · CPC title

• G03F1/22

  Masks or mask blanks for imaging by radiation of 100nm or shorter wavelength, e.g. X-ray masks, extreme ultraviolet [EUV] masks; Preparation thereof · CPC title

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• C08F12/22

  Oxygen · CPC title

• C09D125/18

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title