Developer, pattern forming method, and electronic device manufacturing method

Patent metadata

Field	Value
Publication number	US-10562991-B2
Application number	US-201715849690-A
Country	US
Kind code	B2
Filing date	Dec 21, 2017
Priority date	Jun 23, 2015
Publication date	Feb 18, 2020
Grant date	Feb 18, 2020

Abstract

Provided is a pattern forming method including the successive steps of: a resist film forming step of forming a resist film using an actinic ray-sensitive or radiation-sensitive composition; an exposure step of exposing the resist film; a step of developing the exposed resist film using a developer, and a step of rinsing the developed resist film using a rinsing liquid containing an organic solvent. The developer includes a ketone-based or ether-based solvent having a branched alkyl group. The organic solvent contained in the rinsing liquid includes an ether-based solvent having a branched alkyl group.

First claim

What is claimed is:

1. A pattern forming method comprising the successive steps of:
a resist film forming step of forming a resist film using an actinic ray-sensitive or radiation-sensitive composition,
an exposure step of exposing the resist film,
a step of developing the exposed resist film using a developer, and
a step of rinsing the developed resist film using a rinsing liquid containing an organic solvent,
wherein the developer includes a ketone-based or ether-based solvent having a branched alkyl group, the ketone-based or ether-based solvent has 6 or more carbon atoms and 1 heteroatom, and
the organic solvent contained in the rinsing liquid includes an ether-based solvent having a branched alkyl group.

2. The pattern forming method according to claim 1 , wherein the actinic ray-sensitive or radiation-sensitive composition contains a resin containing a repeating unit represented by General Formula (1):

in General Formula (1),
A represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, or a cyano group,
R represents a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group, an aralkyl group, an alkoxy group, an alkylcarbonyloxy group, an alkylsulfonyloxy group, an alkyloxycarbonyl group, or an aryloxycarbonyl group; in the case where there are a plurality of R's, they may be the same or different; and in the case of having a plurality of R's, they may form a ring in cooperation with each other,
a represents an integer of 1 to 3, and
b represents an integer of 0 to (3-a).

3. The pattern forming method according to claim 1 , wherein the exposure is carried out using electron beams or extreme ultraviolet rays.

4. An electronic device manufacturing method, comprising:
the pattern forming method according to claim 1 .

5. The pattern forming method according to claim 1 , wherein the actinic ray-sensitive or radiation-sensitive composition contains a resin containing a repeating unit represented by General Formula (VI):

in General Formula (VI),
R 61 , R 62 , and R 63 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, meanwhile, R 62 and Ar 6 may be bonded to each other to form a ring, and R 62 in this case represents a single bond or an alkylene group,
X6 represents a single bond, —COO—, or —CONR 64 —, R 64 represents a hydrogen atom or an alkyl group,
L 6 represents a single bond or an alkylene group,
Ar 6 represents an (n+1)-valent aromatic ring group, and Ar 6 represents an (n+2)-valent aromatic ring group in the case of being bonded to R 62 to form a ring,
in the case of n≥2, Y 2 's each independently represent a hydrogen atom or a group capable of leaving by the action of an acid, provided that at least one of Y 2 's represents a group capable of leaving by the action of an acid,
n represents an integer of 1 to 4.

6. The pattern forming method according to claim 1 , wherein the organic solvent contained in the rinsing liquid further includes undecane or diisobutyl ketone.

7. The pattern forming method according to claim 1 , wherein the developer includes diisobutyl ketone, diisobutyl ether, methyl isopropyl ketone, methyl isopentyl ketone, diisopentyl ether or dipropylene glycol methyl-n-propyl ether.

8. A pattern forming method comprising the successive steps of:
a resist film forming step of forming a resist film using an actinic ray-sensitive or radiationsensitive composition,
an exposure step of exposing the resist film,
a step of developing the exposed resist film using a developer, and
a step of rinsing the developed resist film using a rinsing liquid containing an organic solvent,
wherein the developer is selected from a group of consisting of:
2-isopropylcyclohexanone, 3-isopropylcyclohexanone, 4-isopropylcyclohexanone, 2-isopropylcycloheptanone, 3-isopropylcycloheptanone, 4-isopropylcycloheptanone, 2-isopropylcyclooctanone;
diisohexyl ketone, methyl isopentyl ketone, ethyl isopentyl ketone, propyl isopentyl ketone, diisopentyl ketone, methyl isobutyl ketone, ethyl isobutyl ketone, propyl isobutyl ketone, diisobutyl ketone, diisopropyl ketone, ethyl isopropyl ketone, and methyl isopropyl ketone;
cyclopentyl isopropyl ether, cyclopentyl sec-butyl ether, cyclopentyl tert-butyl ether, cyclohexyl isopropyl ether, cyclohexyl sec-butyl ether, cyclohexyl tert-butyl ether;
diisohexyl ether, methyl isopentyl ether, ethyl isopentyl ether, propyl isopentyl ether, diisopentyl ether, methyl isobutyl ether, ethyl isobutyl ether, propyl isobutyl ether, diisobutyl ether, diisopropyl ether, ethyl isopropyl ether, methyl isopropyl ether, and dipropylene glycol methyl-n-propyl ether,
the organic solvent contained in the rinsing liquid includes an ether-based solvent having a branched alkyl group.

9. The pattern forming method according to claim 8 , wherein the actinic ray-sensitive or radiation-sensitive composition contains a resin containing a repeating unit represented by General Formula (1):

in General Formula (1),
A represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, or a cyano group,
R represents a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group, an aralkyl group, an alkoxy group, an alkylcarbonyloxy group, an alkylsulfonyloxy group, an alkyloxycarbonyl group, or an aryloxycarbonyl group; in the case where there are a plurality of R's, they may be the same or different; and in the case of having a plurality of R's, they may form a ring in cooperation with each other,
a represents an integer of 1 to 3, and
b represents an integer of 0 to (3-a).

10. The pattern forming method according to claim 8 , wherein the exposure is carried out using electron beams or extreme ultraviolet rays.

11. An electronic device manufacturing method, comprising:
the pattern forming method according to claim 8 .

12. The pattern forming method according to claim 8 , wherein the actinic ray-sensitive or radiation-sensitive composition contains a resin containing a repeating unit represented by General Formula (VI):

in General Formula (VI),
R 61 , R 62 , and R 63 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group, meanwhile, R 62 and Ar 6 may be bonded to each other 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 —, R 64 represents a hydrogen atom or an alkyl group,
L 6 represents a single bond or an alkylene group,
Ar 6 represents an (n+1)-valent aromatic ring group, and Ar 6 represents an (n+2)-valent aromatic ring group in the case of being bonded to R 62 to form a ring,
in the case of n≥2, Y 2 's each independently represent a hydrogen atom or a group capable of leaving by the action of an acid, provided that at least one of Y 2 's represents a group capable of leaving by the action of an acid,
n represents an integer of 1 to 4.

13. The pattern f

Assignees

• Fujifilm Corp

Inventors

• Tsubaki Hideaki
• Tsuchihashi Toru
• Nihashi Wataru

Classifications

• C08F212/24 Primary

  Phenols or alcohols · CPC title

• C08F212/32

  containing two or more rings · CPC title

• C08F212/22

  Oxygen · CPC title

• H10P76/00

  Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography · CPC title

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title