Active light sensitive or radiation sensitive resin composition, active light sensitive or radiation sensitive film, mask blank provided with active light sensitive or radiation sensitive film, pattern forming method, method for manufacturing electronic device, electronic device and novel compound

Patent metadata

Field	Value
Publication number	US-10324374-B2
Application number	US-201615080714-A
Country	US
Kind code	B2
Filing date	Mar 25, 2016
Priority date	Sep 30, 2013
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

There is provided an active light sensitive or radiation sensitive resin composition which contains (A) an alkali soluble resin and (C) a cross-linking agent represented by the following General Formula (1-0).

First claim

What is claimed is:

1. An active light sensitive or radiation sensitive resin composition, comprising:
(A) an alkali soluble resin;
(B) a compound that generates an acid by irradiation with active light or radiation; and
(C) at least one cross-linking agent selected from the group of compounds represented by the following General Formula (1-0) or General Formula (1-1),

wherein, in the General Formula (1-0),
each of X 1 and X 2 independently represents a hydrogen atom, an alkyl group, a hydroxymethyl group, or an alkoxymethyl group,
each of Y 0 and Y 1 independently represents a carbon atom, a nitrogen atom, or an oxygen atom,
at least one of k X 1 's and n X 2 's is a hydroxymethyl group or an alkoxymethyl group, and at least one of Y 0 and Y 1 is a nitrogen atom substituted with the hydroxymethyl group or the alkoxymethyl group,
Y 2 represents a single bond or an alkylene group,
Z represents an m valent connecting group,
k is 3 when Y 0 is a carbon atom, is 2 when Y 0 is a nitrogen atom, and is 1 when Y 0 is an oxygen atom,
n is 2 when Y 1 is a carbon atom, is 1 when Y 1 is a nitrogen atom, and is 0 when Y 1 is an oxygen atom,
m represents an integer of 2 to 6, and
two of X 1 , X 2 , and Y 2 may be bonded to each other to form a ring, provided that, in a case where X 1 and Y 2 are bonded to each other to form a ring, Z is a connecting group selected from the group consisting of a linear or branched alkylene group, a cycloalkylene group an arylene group, an ether bond, a thioether bond, an amide bond, a urethane bond, a urea bond, and a group obtained by combining two or more thereof

wherein, in the General Formula (1-1),
R represents a hydrogen atom or an alkyl group,
each of X 1 and X 2 independently represents a hydrogen atom, an alkyl group, a hydroxymethyl group, or an alkoxymethyl group,
at least one of X 1 and n X 2 's is a hydroxymethyl group or an alkoxymethyl group, and at least one of a nitrogen atom substituted with X 1 and Y 1 is a nitrogen atom substituted with the hydroxymethyl group or the alkoxymethyl group,
Y 1 represents a carbon atom, a nitrogen atom, or an oxygen atom,
Y 2 represents a single bond or an alkylene group,
each of Y 3 and Y 4 independently represents a single bond, a carbon atom, a nitrogen atom, or an oxygen atom,
each of X 3 and X 4 independently represents a hydrogen atom or an alkyl group,
Z 2 represents a chain or cyclic saturated hydrocarbon group, an aromatic hydrocarbon group, or a group obtained by combining two or more thereof,
n is 2 when Y 1 is a carbon atom, is 1 when Y 1 is a nitrogen atom, and is 0 when Y 1 is an oxygen atom,
n1 is 0 when Y 3 is a single bond or an oxygen atom, is 1 when Y 3 is a nitrogen atom, and is 2 when Y 3 is a carbon atom,
n2 is 0 when Y 4 is a single bond or an oxygen atom, is 1 when Y 4 is a nitrogen atom, and is 2 when Y 4 is a carbon atom,
m represents an integer of 2 to 6, and
two of X 1 , X 2 , and Y 2 may be bonded to each other to form a ring, provided that, in a case where X 1 and Y 2 are bonded to each other to form a ring, Z 2 represents a chain or cyclic saturated hydrocarbon group, or an aromatic hydrocarbon group, and
wherein the molecular weight of the cross-linking agent (C) is 450 to 1500.

2. The active light sensitive or radiation sensitive resin composition according to claim 1 ,
wherein the cross-linking agent (C) is represented by the following General Formula (1),

wherein, in the formula,
R represents a hydrogen atom or an alkyl group,
each of X 1 and X 2 independently represents a hydrogen atom, an alkyl group, a hydroxymethyl group, or an alkoxymethyl group,
Y 1 represents a carbon atom, a nitrogen atom, or an oxygen atom,
Y 2 represents a single bond or an alkylene group,
Z represents an m valent connecting group,
n is 2 when Y 1 is a carbon atom, is 1 when Y 1 is a nitrogen atom, and is 0 when Y 1 is an oxygen atom,
m represents an integer of 2 to 6, and
two of X 1 , X 2 , and Y 2 may be bonded to each other to form a ring, provided that, in a case where X 1 and Y 2 are bonded to each other to form a ring, Z is a connecting group selected from the group consisting of a linear or branched alkylene group, a cycloalkylene group, an arylene group, an ether bond, a thioether bond, an amide bond, a urethane bond, a urea bond, and a group obtained by combining two or more thereof.

3. The active light sensitive or radiation sensitive resin composition according to claim 2 ,
wherein, in General Formula (1), Z is represented by the following General Formula (2), and

wherein, in the formula,
each of Y 3 and Y 4 independently represents a single bond, a carbon atom, a nitrogen atom, or an oxygen atom,
each of X 3 and X 4 independently represents a hydrogen atom or an alkyl group,
when Y 3 and Y 4 are single bonds or oxygen atoms, each of n1 and n2 is 0, when Y 3 and Y 4 are nitrogen atoms, each of n1 and n2 is 1, and when Y 3 and Y 4 are carbon atoms, each of n1 and n2 is 2,
Z 2 represents a chain or cyclic saturated hydrocarbon group, an aromatic hydrocarbon group, or a group obtained by combining two or more thereof,
m2 represents an integer of 2 to 6, and corresponds to m in General Formula (1), and
* represents a linking site with Y 2 in General Formula (1).

4. The active light sensitive or radiation sensitive resin composition according to claim 3 ,
wherein, in General Formula (2), m2 is 2 or 3.

5. The active light sensitive or radiation sensitive resin composition according to claim 3 ,
wherein, in General Formula (2),
Z 2 represents a cyclic saturated hydrocarbon group, an aromatic hydrocarbon group, or a combination of a cyclic saturated hydrocarbon group and an aromatic hydrocarbon group.

6. The active light sensitive or radiation sensitive resin composition according to claim 2 ,
wherein, in General Formula (1), m is 2 or 3.

7. The active light sensitive or radiation sensitive resin composition according to claim 1 ,
wherein the compound (B) that generates an acid by irradiation with active light or radiation is a sulfonium salt.

8. An active light sensitive or radiation sensitive film which is formed of the active light sensitive or radiation sensitive resin composition according to claim 1 .

9. A mask blank provided with the active light sensitive or radiation sensitive film according to claim 8 .

10. A pattern forming method, comprising:
a step of forming a film by applying the active light sensitive or radiation sensitive resin composition claim 1 to a substrate;
a step of exposing the film; and
a step of forming a negative-type pattern by developing the exposed film.

11. A method for manufacturing an electronic device, comprising:
the pattern forming method according to claim 10 .

12. The active light sensitive or radiation sensitive resin composition according to claim 1 ,
wherein the compound (B

Assignees

• Fujifilm Corp

Inventors

• Yamaguchi Shuhei
• Tsuchimura Tomotaka
• Yokokawa Natsumi
• Takahashi Koutarou

Classifications

• C07C275/26

  having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings · CPC title

• G03F7/0382

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

• C07C275/24

  containing six-membered aromatic rings · CPC title

• C07D333/76

  Dibenzothiophenes · CPC title

• C07D235/26

  Oxygen atoms · CPC title