IP Library Granted Patent US 9,527,809
Granted Patent B2
US 9,527,809 · App. 14/868,408 · Granted Dec 27, 2016

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

Inventors: Natsumi Yokokawa (Shizuoka, JP); Hiroo Takizawa (Shizuoka, JP); Shuji Hirano (Shizuoka, JP); Wataru Nihashi (Shizuoka, JP); Hideaki Tsubaki (Shizuoka, JP)
Assignee: FUJIFILM Corporation
C07C381/12C07D309/12C07D317/22G03F7/0045G03F7/0046G03F7/038G03F7/039G03F7/0392G03F7/0397G03F7/20G03F7/2004G03F7/2041G03F7/2059G03F7/325H01L21/0275
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Quick Facts
Patent No.
US 9,527,809
App. No.
14/868,408
Granted
Dec 27, 2016
Kind
B2
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.

Claims (70)

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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2015
From: YOKOKAWA, NATSUMI; TAKIZAWA, HIROO; HIRANO, SHUJI; NIHASHI, WATARU; TSUBAKI, HIDEAKI
To: FUJIFILM CORPORATION
Reel/Frame 036741/0656 →
Priority Claims (1)
JP 2013-075196 · Mar 29, 2013 · national
Continuity (2)
Continuation PCTJP2014055678 · Mar 5, 2014
Related Publication 20160024005A1 · Jan 28, 2016