Pattern forming method, actinic ray-sensitive or radiation-sensitive resin composition, method for manufacturing electronic device, and electronic device

Patent metadata

Field	Value
Publication number	US-9952509-B2
Application number	US-201615200059-A
Country	US
Kind code	B2
Filing date	Jul 1, 2016
Priority date	Jan 29, 2014
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

The present invention relates to a pattern forming method including:
forming a film using an actinic ray-sensitive or radiation-sensitive resin composition that includes a (A) resin which has an increase in the polarity by the action of an acid, and thus, has a decrease in the solubility in a developer containing an organic solvent, a (B) compound capable of generating an acid upon irradiation with specific actinic ray or radiation, and a (C) solvent, exposing the film, and developing the exposed film using a developer including an organic solvent, in which the resin (A) has a structure in which a polar group is protected with a leaving group which decomposes to leave by the action of an acid, and the leaving group is a group represented by the following General Formula (I).

First claim

What is claimed is:

1. A pattern forming method comprising:
forming a film using an actinic ray-sensitive or radiation-sensitive resin composition including (A) a resin which has an increase in the polarity by the action of an acid, and thus, has a decrease in the solubility in a developer containing an organic solvent, (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation, represented by the following General Formula (ZI-3) or (ZI-4), (C) a solvent, and an onium salt composed of a relatively weak acid with respect to the acid generated from the compound (B) upon irradiation with actinic rays or radiation;
exposing the film; and
developing the exposed film using a developer including an organic solvent,
wherein the resin (A) has a structure in which a polar group is protected with a leaving group that decomposes to leave by the action of an acid, and the leaving group is a group represented by the following General Formula (I), and
wherein the onium salt is a compound represented by the following General Formulas (d1-1) to (d1-3) or a compound represented by the following General Formulas (C-1) to (C-3):

in General Formula (I), Z represents a group which is combined with a carbon atom to form a ring structure, Ra 1 to Ra 3 each independently represent an organic group, at least two members out of Ra 1 to Ra 3 may be bonded to each other to form a ring, and * represents a direct bond;

in General Formula (ZI-3), R 1c to R 5c each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a cycloalkylcarbonyloxy group, a halogen atom, a hydroxyl group, a nitro group, an alkylthio group, or an arylthio group,
R 6c and R 7c each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an aryl group,
Rx and Ry each independently represent an alkyl group, a cycloalkyl group, a 2-oxoalkyl group, a 2-oxocycloalkyl group, an alkoxycarbonylalkyl group, an allyl group, or a vinyl group,
among any two or more members out of R 1c to R 5c , R 5c and R 6c , R 6c and R 7c , R 5c and Rx, and Rx and Ry each may be bonded to each other to form a ring structure, and the ring structure may contain an oxygen atom, a sulfur atom, a ketone group, an ester bond, or an amide bond, and
Zc − represents a non-nucleophilic anion;

in General Formula (ZI-4), R 13 represents a group having a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkoxycarbonyl group, or a cycloalkyl group,
R 14 's, in the case where they are present in plural numbers, each independently represent a group having a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylsulfonyl group, a cycloalkylsulfonyl group, or a cycloalkyl group,
R 15 's each independently represent an alkyl group, a cycloalkyl group, or a naphthyl group, two R 15 's may be bonded to each other to form a ring, and the ring structure may contain an oxygen atom, a sulfur atom, a ketone group, an ester bond, or an amide bond,
l represents an integer of 0 to 2,
r represents an integer of 0 to 8, and
Z − represents a non-nucleophilic anion;

in General Formulas (d1-1) to (d1-3), R 51 is a hydrocarbon group which may have a substituent, Z 2c is a hydrocarbon group having 1 to 30 carbon atoms, which may have a substituent, provided that carbon adjacent to S is not substituted with a fluorine atom, R 52 is an organic group, Y 3 is a linear, branched, or cyclic alkylene group or arylene group, Rf is a hydrocarbon group containing a fluorine atom, and M + 's are each independently a sulfonium cation or an iodonium cation; and

in General Formulas (C-1) to (C-3),
R 1 , R 2 , and R 3 represent a substituent having 1 or more carbon atoms,
L 1 represents a divalent linking group that links a cationic moiety with an anionic moiety, or a single bond,
—X − represents an anionic moiety selected from —COO − , —SO 3 − , —SO 2 − , and —N − —R 4 , R 4 represents a monovalent substituent having a carbonyl group: —C(═O)—, a sulfonyl group: —S(═O) 2 —, or a sulfinyl group: —S(═O)— at a site for linking to an adjacent N atom,
R 1 , R 2 , R 3 , R 4 , and L 1 may be bonded to one another to form a ring structure, and in (C-3), two members out of R 1 to R 3 may be combined to form a double bond with an N atom.

2. The pattern forming method according to claim 1 , wherein the compound (B) is a compound capable of generating an acid represented by the following General Formula (II) upon irradiation with actinic ray or radiation:

in General Formula (II), R 1 and R 2 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group, and R 1 and R 2 , in the case where they are present in plural numbers, may be the same as or different from each other,
L represents a divalent linking group and L's in the case where they are present in plural numbers may be the same as or different from each other,
A represents a cyclic organic group,
x represents an integer of 0 to 20, and y represents an integer of 0 to 10.

3. The pattern forming method according to claim 1 , wherein the content of the compound (B) is more than 5% by mass with respect to the total solids content of the actinic ray-sensitive or radiation-sensitive resin composition.

4. The pattern forming method according to claim 2 , wherein the content of the compound (B) is more than 5% by mass with respect to the total solids content of the actinic ray-sensitive or radiation-sensitive resin composition.

5. The pattern forming method according to claim 1 , wherein the developer including an organic solvent is a developer containing at least one kind of solvent selected from a ketone-based solvent, an ester-based solvent, an alcohol-based solvent, an amide-based solvent, and an ether-based solvent.

6. A method for manufacturing an electronic device, comprising the pattern forming method according to claim 1 .

Assignees

• Fujifilm Corp

Inventors

• Kato Keita
• OU Keiyu
• Shirakawa Michihiro
• Goto Akiyoshi
• KOJIMA Masafumi

Classifications

• G03F7/2035

  simultaneous coating and exposure; using a belt mask, e.g. endless · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/322

  Aqueous alkaline compositions · CPC title

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title