Pattern formation method, active light-sensitive or radiation-sensitive resin composition, resist film, production method for electronic device using same, and electronic device

Patent metadata

Field	Value
Publication number	US-2016147154-A1
Application number	US-201615011813-A
Country	US
Kind code	A1
Filing date	Feb 1, 2016
Priority date	Aug 1, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

There are provided a pattern formation method, including:
(1) forming a film using an active light-sensitive or radiation-sensitive resin composition; (2) exposing the film to active light or radiation; and (3) developing the exposed film using a developer including an organic solvent, wherein the active light-sensitive or radiation-sensitive resin composition contains a resin (A) having specific repeating units, and a crosslinking agent (C).

First claim

What is claimed is:

1 . A pattern formation method, comprising:
(1) forming a film using an active light-sensitive or radiation-sensitive resin composition; (2) exposing the film to active light or radiation; and (3) developing the exposed film using a developer including an organic solvent, wherein the active light-sensitive or radiation-sensitive resin composition contains a resin (A) having a repeating unit represented by General Formula (I) and a repeating unit represented by any one of General Formulas (II) to (IV), and a crosslinking agent (C),

wherein, in General Formula (I), each of R 41 , R 42 , and R 43 independently represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group; here, R 42 may be bonded to Ar 4 to form a ring, and R 42 in this case represents a single bond or an alkylene group; X 4 represents a single bond, —COO—, or —CONR 44 —, and, in the case of forming a ring with R 42 , represents a trivalent connecting group; R 44 represents a hydrogen atom or an alkyl group: L 4 represents a single bond or an alkylene group; Ar 4 represents an (n+1) valent aromatic ring group, and, in the case of being bonded to R 42 to form a ring, represents an (n+2) valent aromatic ring group; and n represents an integer of 1 to 4,

wherein, in General Formula (II), each of R 61 , R 62 , and R 63 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 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 a divalent aromatic ring group, and, in the case of being bonded to R 62 to form a ring, represents a trivalent aromatic ring group; R 3 represents 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 3 represents a single bond or a divalent connecting group; Q 3 represents an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group; and at least two of Q 3 , M 3 , and R 3 may be bonded to each other to form a ring,
wherein, in General Formula (III), each of R 51 , R 52 , and R 53 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group; R 52 may be bonded to L 5 to form a ring, and R 52 in this case represents an alkylene group; L 5 represents a single bond, or an alkylene group, —COO-L 1 -, —O-L 1 -, or a divalent connecting group selected from the groups formed by combining two or more thereof, and L 1 represents an alkylene group or a cycloalkylene group; here, in a case where L 5 is bonded to R 52 to form a ring, L 5 represents a trivalent connecting group; R 54 represents an alkyl group, and each of R 55 and R 56 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group; and R 55 and R 56 may be bonded to each other to form a ring; however, R 55 and R 56 do not represent a hydrogen atom at the same time in any case, and
wherein, in General Formula (IV), each of R 71 , R 72 , and R 73 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group; R 72 may be bonded to L 7 to form a ring, and R 72 in this case represents an alkylene group; L 7 represents a single bond or a divalent connecting group, and in the case of forming a ring with R 72 , represents a trivalent connecting group; R 74 represents 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 connecting 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 , and R 74 may be bonded to each other to form a ring.

2 . The pattern formation method according to claim 1 ,
wherein the crosslinking agent (C) is a compound having a hydroxymethyl group, an alkoxymethyl group, an oxirane ring, or an oxetane ring.

3 . The pattern formation method according to claim 2 ,
wherein the crosslinking agent (C) is a phenol derivative, a urea-based compound, or a melamine-based compound, having a hydroxymethyl group or an alkoxymethyl group.

4 . The pattern formation method according to claim 1 ,
wherein the content of the crosslinking agent (C) is 3% by mass to 65% by mass with respect to the total solid content in the active light-sensitive or radiation-sensitive resin composition.

5 . The pattern formation method according to claim 1 ,
wherein the resin (A) has the repeating unit represented by General Formula (II), and R 3 in General Formula (II) is a group having 2 or more carbon atoms.

6 . The pattern formation method according to claim 5 ,
wherein the resin (A) has the repeating unit represented by General Formula (II), and R 3 in General Formula (II) is a group represented by the following General Formula (II-2), and

wherein, in General Formula (II-2), each of Ra 81 , R 82 , and R 83 independently represents an alkyl group, an alkenyl group, a cycloalkyl group, or an aryl group; n81 represents 0 or 1; and at least two of R 81 to R 83 may be connected to each other to form a ring.

7 . The pattern formation method according to claim 1 ,
wherein the resin (A) has a repeating unit represented by General Formula (III), and the repeating unit represented by General Formula (III) is a repeating unit represented by the following General Formula (III-1), and

wherein, in General Formula (III-1), each of R 1 and R 2 independently represents an alkyl group, each of R 11 and R 12 independently represents an alkyl group, and R 13 represents a hydrogen atom or an alkyl group; R 11 and R 12 may be connected to each other to form a ring, and R 11 and R 13 may be connected to each other to form a ring; Ra represents a hydrogen atom, an alkyl group, a cyano group, or a halogen atom, L 5 represents a single bond, or an alkylene group, —COO-L 1 -, —O-L 1 -, or a divalent connecting group selected from the groups formed by combining two or more thereof, and L 1 represents an alkylene group or a cycloalkylene group.

8 . The pattern formation method according to claim 7 ,
wherein R 11 and R 12 in General Formula (III-1) are connected to each other to form a ring.

9 . The pattern formation method according to claim 1 ,
wherein the bond between X 4 and L 4 in General Formula (I) is a single bond.

10 . The pattern formation method according to claim 1 ,
wherein the content of the repeating unit represented by General Formula (I) is 10 mol % to 40 mol % of the entirety of repeating units in the resin (A).

11 . The pattern formation method according to claim 1 ,
wherein the active light-sensitive or radiation-sensitive resin composition further includes a compound (B) that generates an acid by active light or radiation.

12 . The pa

Assignees

• Fujifilm Corp

Inventors

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

Classifications

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/26

  Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence) · CPC title

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/327

  Non-aqueous alkaline compositions, e.g. anhydrous quaternary ammonium salts · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title