Compound, active light sensitive or radiation sensitive resin composition, resist film using same, resist-coated mask blank, photomask, pattern forming method, method for manufacturing electronic device, and electronic device

Patent metadata

Field	Value
Publication number	US-9904167-B2
Application number	US-201514982759-A
Country	US
Kind code	B2
Filing date	Dec 29, 2015
Priority date	Jul 10, 2013
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

Provided is an active light sensitive or radiation sensitive resin composition which contains a compound (A) represented by General Formula (I) or (II):

in the formulae, each of Y 1 and Y 2 represents a monovalent organic group; each of M 1 + and M 2 + represents an organic onium ion; each of X 1 and X 2 represents a group that is represented by —S—, —NH—, or —NR 1 —; R 1 represents a monovalent organic group; each of n1 and n2 represents an integer of 1 or more; and R 1 and Y 1 or Y 2 may bond with each other to form a ring.

First claim

What is claimed is:

1. An active light sensitive or radiation sensitive resin composition comprising:
a compound (A) represented by General Formula (I) below,

 in the formula,
Y 1 represents a monovalent organic group;
M 1 + represents an organic onium ion;
X 1 represents a group which is represented by —S—, —NH—, or —NR 1 —; R 1 represents a monovalent organic group;
n1 represents an integer of 1 or more; and
R 1 and Y 1 may bond with each other to form a ring;

(B) a resin, and
a solvent,
wherein, in General Formula (I), Y 1 is a monovalent hydrocarbon group which has an alicyclic hydrocarbon structure having 5 or more carbon atoms.

2. The active light sensitive or radiation sensitive resin composition according to claim 1 ,
wherein, in General Formula (I), X 1 is a group which is represented by —NH— or —NR 1 —.

3. The active light sensitive or radiation sensitive resin composition according to claim 1 ,
wherein, in General Formula (I), X 1 is a group which is represented by —S—.

4. The active light sensitive or radiation sensitive resin composition according to claim 1 ,
wherein the resin (B) has a phenolic hydroxyl group.

5. The active light sensitive or radiation sensitive resin composition according to claim 4 ,
wherein the resin (B) is a resin which has a repeating unit represented by General Formula (1) below:

in General Formula (1),
R 11 represents a hydrogen atom, a methyl group, or a halogen atom;
B 1 represents a single bond or a divalent linking group;
Ar represents an aromatic ring; and
m1 represents an integer of 1 or more.

6. The active light sensitive or radiation sensitive resin composition according to claim 4 ,
wherein the resin (B) is a resin which has a repeating unit represented by General Formula (A) below:

in General Formula (A),
R 01 , R 02 , and R 03 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, or an alkoxycarbonyl group;
Ar 1 represents an aromatic ring group;
R 03 and Ar 1 may bond with each other to form a 5- or 6-membered ring with a main chain of the repeating unit represented by General Formula (A);
n Y's each independently represent a hydrogen atom or a group which is released due to an action of an acid;
at least one Y represents a group which is released due to an action of an acid; and n represents an integer of 1 to 4.

7. The active light sensitive or radiation sensitive resin composition according to claim 1 , further comprising:
an acid cross-linkable compound (C).

8. The active light sensitive or radiation sensitive resin composition according to claim 7 ,
wherein the compound (C) is a compound which has two or more hydroxymethyl groups or alkoxymethyl groups in a molecule.

9. The active light sensitive or radiation sensitive resin composition according to claim 1 ,
wherein the alicyclic hydrocarbon structure is a polycyclic alicyclic hydrocarbon structure.

10. A resist film formed using the active light sensitive or radiation sensitive resin composition according to claim 1 .

11. A resist-coated mask blank coated with the resist film according to claim 10 .

12. A photomask obtained by exposing and developing the resist-coated mask blank according to claim 11 .

13. A pattern forming method comprising:
exposing the resist film according to claim 10 ; and
developing the exposed film.

14. A pattern forming method comprising:
exposing the resist-coated mask blank according to claim 11 ; and
developing the exposed mask blank.

15. A method for manufacturing an electronic device, comprising:
forming a resist film on a substrate for use in the electronic device using the active light sensitive or radiation sensitive resin composition according to claim 1 ;
pattern-wise exposing the resist film; and
developing the exposed film by using a developer to form a pattern on the substrate.

16. A compound represented by General Formula (I-I) below:

in the formula,
X′ represents —S— or —NH—;
n′ represents an integer of 1 to 3;
Y′ represents an aryl group or a monovalent hydrocarbon group which has an alicyclic hydrocarbon structure having 5 or more carbon atoms; and
M′ + represents a sulfonium cation or an iodonium cation.

17. An active light sensitive or radiation sensitive resin composition comprising:
a compound (A) represented by General Formula (I) or (II) below,

 in the formulae,
each of Y 1 and Y 2 represents a monovalent organic group;
each of M 1 + and M 2 + represents an organic onium ion;
each of X 1 and X 2 represents a group which is represented by —S—;
each of n1 and n2 represents an integer of 1 or more; and
R 1 and Y 1 or Y 2 may bond with each other to form a ring;

(B) a resin; and
a solvent.

Assignees

• Fujifilm Corp

Inventors

• Tsuchimura Tomotaka

Classifications

• H10P76/2043

  using an anti-reflective coating · CPC title

• H10P76/20

  of masks comprising organic materials · CPC title

• G03F7/0382

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• C07D327/08

  [b,e]-condensed with two six-membered carbocyclic rings · CPC title