IP Library Granted Patent US 10,882,839
Granted Patent B2
US 10,882,839 · App. 16/154,048 · Granted Jan 5, 2021

Salt and photoresist composition containing the same

Inventors: Tatsuro Masuyama (Osaka, JP); Natsuki Okada (Osaka, JP); Koji Ichikawa (Osaka, JP)
Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
C07D317/72C07D319/08C07D493/10G03F7/0045G03F7/0046G03F7/0397G03F7/2002G03F7/40
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Quick Facts
Patent No.
US 10,882,839
App. No.
16/154,048
Granted
Jan 5, 2021
Kind
B2
Abstract

A salt containing a group represented by the formula (aa): wherein X a and X b independently each represent an oxygen atom or a sulfur atom, a ring W represents a C3-C18 heterocycle which has a carbonate ester structure and which can have a substituent, and * represents a binding position is provided.

Claims (49)

1. A salt comprising an anion represented by formula (aa2):

wherein X a and X b independently each represent an oxygen atom or a sulfur atom,

a ring W represents a C3-C18 heterocycle which has a carbonate ester structure and which can have a substituent,

a ring W1 represents a C3-C18 non-aromatic hydrocarbon ring which can have a substitute and in which a methylene group can be replaced by —O—, —S—, —CO— or —SO 2 —,

L 1 represents a C1-C24 divalent saturated hydrocarbon group in which a hydrogen atom can be replaced by a fluorine atom or a hydroxyl group and in which a methylene group can be replaced by —O— or —CO—, and

Q 1 and Q 2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group.

2. The salt according to claim 1 ,

wherein the ring W1 represents an adamantane ring or a cyclohexane ring.

3. The salt according to claim 1 ,

wherein L 1 is represented by formula (b1-1) or (b1-2):

in which L b2 represents a single bond or a C1-C22 divalent saturated hydrocarbon group where a hydrogen atom may be replaced by a fluorine atom; L b3 represents a single bond or a C1-C22 divalent saturated hydrocarbon group where a hydrogen atom may be replaced by a hydroxyl group or a fluorine atom and where a methylene group may be replaced by an oxygen atom or carbonyl group, provided that total number of the carbon atoms of L b2 and L b3 is up to 22;

L b4 represents a C1-C22 divalent saturated hydrocarbon group where a hydrogen atom may be replaced by a fluorine atom; and L b5 represents a single bond or a C1-C22 divalent saturated hydrocarbon group where a hydrogen atom may be replaced by a hydroxyl group or a fluorine atom and where a methylene group may be replaced by an oxygen atom or carbonyl group, provided that the total carbon atoms of L b4 and L b5 is up to 22.

4. An acid generator comprising the salt according to claim 1 .

5. A photoresist composition comprising the acid generator according to claim 4 and a resin which comprises a structural unit having an acid-labile group.

6. The photoresist composition according to claim 5 further comprises a salt generating an acid weaker in acidity than an acid generated from the acid generator.

7. A process for producing a photoresist pattern comprising the following steps (1) to (5):

(1) a step of applying the photoresist composition according to claim 5 or 6 on a substrate,

(2) a step of forming a composition film by conducting drying,

(3) a step of exposing the composition film to radiation,

(4) a step of baking the exposed composition film, and

(5) a step of developing the baked composition film thereby forming a photoresist pattern.

8. A salt comprising a group represented by the formula (aa):

wherein X a and X b independently each represent an oxygen atom or a sulfur atom,

a ring W represented 1,3-dioxan-2-one ring, and

* represents a binding position.

9. The salt according to claim 8 , which comprises a cation and an anion having the group represented by formula (aa).

10. The salt according to claim 9 , wherein the anion having the group represented by formula (aa) is a sulfonate anion.

11. The salt according to claim 8 , which has a group represented by formula (aa1):

wherein X a , X b the ring W and * are as defined in claim 8 ,

a ring W1 represents a C3-C18 non-aromatic hydrocarbon ring which can have a substituent and in which a methylene group can be replaced by —O—, —S—, —CO— or —SO 2 —.

12. The salt according to claim 11 , which has an anion represented by formula (aa2):

wherein X a , X b , the ring W and the ring W1 are as defined in claim 11 ,

L 1 represents a C1-C24 divalent saturated hydrocarbon group in which a hydrogen atom can be replaced by a fluorine atom or a hydroxyl group and in which a methylene group can be replaced by —O— or —CO—, and

Q 1 and Q 2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group.

13. The salt according to claim 12 ,

wherein the ring W1 represents an adamantane ring or a cyclohexane ring.

14. The salt according to claim 12 ,

wherein L 1 is represented by formula (b1-1) or (b1-2):

in which L b2 represents a single bond or a C1-C22 divalent saturated hydrocarbon group where a hydrogen atom may be replaced by a fluorine atom; L b3 represents a single bond or a C1-C22 divalent saturated hydrocarbon group where a hydrogen atom may be replaced by a hydroxyl group or a fluorine atom and where a methylene group may be replaced by an oxygen atom or carbonyl group, provided that total number of the carbon atoms of L b2 and L b3 is up to 22;

L b4 represents a C1-C22 divalent saturated hydrocarbon group where a hydrogen atom may be replaced by a fluorine atom; and L b5 represents a single bond or a C1-C22 divalent saturated hydrocarbon group where a hydrogen atom may be replaced by a hydroxyl group or a fluorine atom and where a methylene group may be replaced by an oxygen atom or carbonyl group, provided that the total carbon atoms of L b4 and L b5 is up to 22.

15. An acid generator comprising the salt according to claim 8 .

16. A photoresist composition comprising the acid generator according to claim 15 and a resin which comprises a structural unit having an acid-labile group.

17. The photoresist composition according to claim 16 , which further comprises a salt generating an acid weaker in acidity than an acid generated from the acid generator.

18. A process for producing a photoresist pattern comprising the following steps (1) to (5):

(1) a step of applying the photoresist composition according to claim 16 or 17 on a substrate,

(2) a step of forming a composition film by conducting drying,

(3) a step of exposing the composition film to radiation,

(4) a step of baking the exposed composition film, and

(5) a step of developing the baked composition film thereby forming a photoresist pattern.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 8, 2018
From: MASUYAMA, TATSURO; OKADA, NATSUKI; ICHIKAWA, KOJI
To: SUMITOMO CHEMICAL COMPANY, LIMITED
Reel/Frame 047092/0630 →
Priority Claims (1)
JP 2017-200113 · Oct 16, 2017 · national
Continuity (1)
Related Publication 20190112286A1 · Apr 18, 2019