Actinic ray-sensitive or radiation-sensitive resin composition, resist film, using the same, pattern forming method, manufacturing method of electronic device, and electronic device

Patent metadata

Field	Value
Publication number	US-9551933-B2
Application number	US-201514605631-A
Country	US
Kind code	B2
Filing date	Jan 26, 2015
Priority date	Jul 27, 2012
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

There is provided an actinic ray-sensitive or radiation-sensitive resin composition comprising: (A) a resin containing a repeating unit represented by the first specific formula and a repeating unit represented by the second specific formula, wherein the content of the repeating unit represented by the first specific formula is 35 mol % or more based on all repeating units in the resin (A), a resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition.

First claim

The invention claimed is:

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:
(A) a resin containing a repeating unit represented by the following formula (1-1), a repeating unit represented by the following formula (1-2) and a repeating unit having a lactone structure, and
a compound capable of generating an acid upon irradiation with an actinic ray or radiation,
wherein the content of the repeating unit represented by the following formula (1-1) is 55 mol % or more based on all repeating units in the resin (A):

wherein in formula (1-1),
R 1 represents an alkyl group or a cycloalkyl group, which may have a substituent,
R 2 represents an alkyl group or a cycloalkyl group,
R 3 represents a hydrogen atom or an alkyl group, R 1 and R 2 may combine to form a ring,
Ra represents a hydrogen atom, an alkyl group, a cyano group or a halogen atom, and
L 1 represents a single bond or a divalent linking group;
in formula (1-2),
R 4 represents a substituent,
n 1 represents 1 or 2,
n 2 represents an integer of 0 to 4,
L 2 represents a single bond, —COO— or —CONR 5 —, and R 5 represents a hydrogen atom or an alkyl group.

2. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,
wherein Ra in formula (1-1) is a methyl group.

3. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,
wherein L 1 in formula (1-1) is a single bond.

4. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,
wherein the content of the repeating unit represented by formula (1-2) is at least 15 mol % based on all repeating units in the resin (A).

5. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,
wherein the repeating unit represented by formula (1-1) is a repeating unit represented by the following formula (1-11):

wherein R 2 , R 3 , L 1 and Ra have the same meanings as R 2 , R 3 , L 1 and Ra in formula (1-1),
R 11 represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyl group or a heterocyclic group, and R 11 and R 2 may combine to form a ring.

6. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 5 ,
wherein the repeating unit represented by formula (1-11) is a repeating unit represented by the following formula (1-12):

wherein in formula (1-12),
R 2 , R 3 , L 1 and Ra have the same meanings as R 2 , R 3 , L 1 and Ra in formula (1-1),
each of R 21 to R 23 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a heterocyclic group, each of at least two members of R 21 to R 23 independently represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a heterocyclic group, and
at least two of R 21 to R 23 may combine with each other to form a ring, or at least one of R 21 to R 23 may combine with R 2 to form a ring.

7. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,
wherein the repeating unit represented by formula (1-1) is a repeating unit represented by the following formula (1-13):

wherein in formula (1-13),
R 2 , R 3 , L 1 and Ra have the same meanings as R 2 , R 3 , L 1 and Ra in formula (1-1), each of R 24 to R 26 independently represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a heterocyclic group, and at least two of R 24 to R 26 may combine with each other to form a ring, or at least one of R 24 to R 26 may combine with R 2 to form a ring.

8. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,
wherein the repeating unit having a lactone structure in the resin (A) is a repeating unit represented by formula (2),
the content of the repeating unit represented by formula (1-1) is from 55 to 85 mol % based on all repeating units in the resin (A),
the content of the repeating unit represented by formula (1-2) is from 20 to 45 mol % based on all repeating units in the resin (A), and
the content of the repeating unit represented by formula (2) is from 1 to 40 mol % based on all repeating units in the resin (A):

wherein in formula (2),
each of L 3 and L 4 independently represents a single bond or a divalent linking group,
Y represents an atomic group capable of forming a lactone structure, and
Rb 0 represents a hydrogen atom, an alkyl group, a cyano group or a halogen atom.

9. A resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition claimed in claim 1 .

10. A pattern forming method comprising:
(i) a step of forming a film from the actinic ray-sensitive or radiation-sensitive resin composition claimed in claim 1 ,
(ii) a step of exposing the film, and
(iii′) a step of developing the exposed film by using an organic solvent-containing developer to form a negative pattern.

11. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , wherein the composition further contains a hydrophobic resin.

12. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , wherein in formula (1-2), L 2 represents —COO—.

13. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , wherein in formula (1-2), n 1 represents 2.

14. A pattern forming method comprising:
(i) a step of forming a film from the actinic ray-sensitive or radiation-sensitive resin composition claimed in claim 1 ,
(ii) a step of exposing the film, and
(iii) a step of developing the exposed film by using a developer to form a pattern.

15. The pattern forming method as claimed in claim 14 ,
wherein the exposure is performed using an X-ray, an electron beam or EUV.

16. A method for manufacturing an electronic device, comprising the pattern forming method claimed in claim 15 .

17. An actinic ray-sensitive or radiation-sensitive resin composition comprising:
(A) a resin containing a repeating unit represented by the following formula (1-1), a repeating unit represented by the following formula (1-2) and a repeating unit having a lactone structure, and
a compound capable of generating an acid upon irradiation with an actinic ray or radiation,
wherein the content of the repeating unit represented by the following formula (1-1) is 40 mol % or more based on all repeating units in the resin (A):

wherein in formula (1-1),
R 1 represents an alkyl group or a cycloalkyl group, which may have a substituent,
R 2 represents an alkyl group or a cycloalkyl group,
R 3 represents a hydrogen atom or an alkyl group, R 1 and R 2 may combine to form a ring,
Ra

Assignees

• Fujifilm Corp

Inventors

• Takizawa Hiroo
• Hirano Shuji
• Yokokawa Natsumi
• Nihashi Wataru

Classifications

• C08F212/24 Primary

  Phenols or alcohols · CPC title

• C08F212/30

  Sulfur · CPC title

• C08F212/22

  Oxygen · CPC title

• C08F212/32

  containing two or more rings · CPC title

• C08F212/20

  Fluorine · CPC title