Compound, actinic ray-sensitive or radiation-sensitive resin composition, resist film, and pattern formation method, and method for manufacturing electronic device using same, and electronic device

Patent metadata

Field	Value
Publication number	US-9527809-B2
Application number	US-201514868408-A
Country	US
Kind code	B2
Filing date	Sep 29, 2015
Priority date	Mar 29, 2013
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

There is provided an actinic ray-sensitive or radiation-sensitive resin composition containing a compound represented by the following formula (1) or (2), and the formula (1) and (2) are defined as herein,

and a resist film comprising the actinic ray-sensitive or radiation-sensitive resin composition, and a pattern forming method comprising a step of exposing the resist film, and a step of developing the exposed film, and a method for manufacturing an electronic device, comprising the pattern forming method, and an electronic device manufactured by the manufacturing method of an electronic device.

First claim

The invention claimed is:

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:
a resin;
a solvent; and
a compound represented by the following formula (1) or (2):

wherein
each of R 1 to R 5 independently represents an organic group having a carbon number of 30 or less, at least two members out of R 1 to R 3 may combine with each other to form a ring,
each of at least one of R 1 to R 3 and at least one of R 4 and R 5 has at least one group selected from the group consisting of groups represented by the following formulae (I), (III) to (IV), and
Z − represents a non-nucleophilic anion:

wherein in formulae (I), (III) to (IV),
R 11 represents a hydrogen atom or an alkyl group,
R 12 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group,
R 13 represents an alkyl group, a cycloalkyl group or an aryl group,
R 12 and R 13 may combine with each other to form a ring,
L 3 represents a trivalent linking group,
each of R 31 and R 34 independently represents a hydrogen atom or an alkyl group,
each of R 32 and R 35 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group,
each of R 33 and R 36 independently represents an alkyl group, a cycloalkyl group or an aryl group,
R 32 and R 33 may combine with each other to form a ring,
R 35 and R 36 may combine with each other to form a ring,
L 4 represents a trivalent linking group,
each of R 41 and R 42 independently represents a hydrogen atom or an alkyl group,
R 41 and R 42 may combine with each other to form a ring, and
* represents a bond.

2. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 ,
wherein in formulae (1) and (2), Z − represents a sulfonate anion.

3. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 2 ,
wherein in formulae (1) and (2), Z − represents a benzenesulfonate anion.

4. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , wherein the resin has a group represented by any one of formulae (I), (III) to (IV) and the following formulae (II) and (V):

wherein in formula (II) and formula (V),
each of R 21 to R 24 independently represents an alkyl group,
R 25 represents a hydrogen atom or an alkyl group, at least two members out of R 23 to R 25 may combine with each other to form a ring, provided that R 21 and R 22 do not combine with each other to form a ring and at least one of R 21 and R 22 does not combine with at least one of R 23 to R 25 to form a ring,
Ar represents a divalent aromatic ring group,
each of R 51 and R 52 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a monovalent aromatic ring group, or a group formed by combining an alkylene group and a monovalent aromatic ring group,
M represents a single bond or a divalent linking group,
Q represents an alkyl group, a cycloalkyl group that may contain a heteroatom, a monovalent aromatic ring group that may contain a heteroatom, an amino group, an ammonium group, a mercapto group, a cyano group or an aldehyde group,
two members out of Q, M and R 51 may combine to form a ring, and
* represents a bond.

5. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 4 ,
wherein the resin is a resin having a group represented by formula (I) or (II).

6. The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1 , containing a compound represented by formula (1).

7. A resist film comprising the actinic ray-sensitive or radiation-sensitive resin composition claimed in claim 1 .

8. A pattern forming method comprising:
a step of forming the resist film of claim 7 on a substrate;
a step of exposing the resist film;
a step of developing the exposed film.

9. The pattern forming method as claimed in claim 8 ,
wherein the exposure is performed using an electron beam or an extreme-ultraviolet ray.

10. The pattern forming method as claimed in claim 8 ,
wherein the development is performed using a developer containing an organic solvent.

11. A method for manufacturing an electronic device, comprising employing the pattern forming method claimed in claim 8 to form a pattern on an inorganic substrate or a coating-type inorganic substrate suitable for use in process of producing a semiconductor, a liquid crystal device or a circuit board.

12. A compound represented by formula (1):

wherein
each of R 1 to R 3 independently represents an aryl group having a carbon number of 30 to less, at least two members out of R 1 to R 3 may combine with each other to form a ring,
at least one of R 1 to R 3 has at least one group selected from the group consisting of groups represented by the following formula (I), (III) to (IV),
Z − represents a sulfonate anion:

wherein in formulae (I), (III) to (IV),
R 11 represents a hydrogen atom or an alkyl group,
R 12 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group,
R 13 represents an alkyl group, a cycloalkyl group or an aryl group,
R 12 and R 13 may combine with each other to form a ring,
L 3 represents a trivalent linking group,
each of R 31 and R 34 independently represents a hydrogen atom or an alkyl group,
each of R 32 and R 35 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group,
each of R 33 and R 36 independently represents an alkyl group, a cycloalkyl group or an aryl group,
R 32 and R 33 may combine with each other to form a ring,
R 35 and R 36 may combine with each other to form a ring,
L 4 represents a trivalent linking group,
each of R 41 and R 42 independently represents a hydrogen atom or an alkyl group,
R 41 and R 42 may combine with each other to form a ring, and
* represents a bond.

Assignees

• Fujifilm Corp

Inventors

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

Classifications

• G03F7/2059

  using a scanning corpuscular radiation beam, e.g. an electron beam · CPC title

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · 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