Sulfonamide-containing topcoat and photoresist additive compositions and methods of use

Patent metadata

Field	Value
Publication number	US-9422445-B2
Application number	US-201514933851-A
Country	US
Kind code	B2
Filing date	Nov 5, 2015
Priority date	Feb 19, 2010
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

Provided are sulfonamide-containing compositions, topcoat polymers, and additive polymers for use in lithographic processes that have improved static receding water contact angles over those known in the art. The sulfonamide-containing topcoat polymers and additive polymers of the present invention include sulfonamide-substituted repeat units with branched linking group as shown in Formula (I):

First claim

We claim:

1. A composition comprising a homopolymer, the homopolymer comprising a repeat unit having a sulfonamide group and a branched linking group, according to Formula (I)

wherein,
R1 and R2 are independently selected from hydrogen and fluorine;
R3 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R4 is hydrogen;
R5 and R6 are methyl; and
R7 is fluorinated C1-C12 alkyl.

2. The composition of claim 1 , wherein R7 is selected from trifluoromethyl and perfluorobutyl.

3. A composition comprising a copolymer, the copolymer comprising:
a first repeat unit comprising a sulfonamide group and a branched linking group, according to Formula (I)

wherein,
R1 and R2 are independently selected from hydrogen and fluorine;
R3 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R4 is hydrogen;
R5 and R6 are methyl; and
R7 is fluorinated C1-C12 alkyl, and

a second repeat unit according to the following formula:

wherein,
R32 and R33 are independently selected from hydrogen and fluorine;
R34 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R35 is selected from the group consisting of C1-C12 fluorinated alkyl, C6-C20 fluorinated aryl, and C1-C20 fluorinated ether.

4. The composition of claim 3 , wherein R7 is selected from trifluoromethyl and perfluorobutyl.

5. The composition of claim 3 , wherein the first repeat unit constitutes at least 5 mole % of the copolymer.

6. The composition of claim 3 , wherein the first repeat unit constitutes at least 50 mole % of the copolymer.

7. A composition comprising a copolymer, the copolymer comprising:
a first repeat unit comprising a sulfonamide group and a branched linking group, according to Formula (I)

wherein,
R1 and R2 are independently selected from hydrogen and fluorine;
R3 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R4 is hydrogen;
R5 and R6 are methyl; and
R7 is fluorinated C1-C12 alkyl, and

a second repeat unit according to the following formula:

wherein:
R36 and R37 are independently selected from hydrogen and fluorine;
R38 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R39 is selected from C1-C12 alkylene and C6-C20 arylene.

8. The composition of claim 7 , wherein R7 is selected from trifluoromethyl and perfluorobutyl.

9. The composition of claim 7 , wherein the first repeat unit constitutes at least 5 mole % of the copolymer.

10. The composition of claim 7 , wherein the first repeat unit constitutes at least 20 mole % of the copolymer.

11. A composition comprising a copolymer, the copolymer comprising:
a first repeat unit comprising a sulfonamide group and a branched linking group, according to Formula (I)

wherein,
R1 and R2 are independently selected from hydrogen and fluorine;
R3 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R4 is hydrogen;
R5 and R6 are methyl; and
R7 is fluorinated C1-C12 alkyl, and

a second repeat unit according to the following formula:

wherein:
R40 and R41 are independently selected from hydrogen and fluorine;
R42 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R43 is a C4-C20 tertiary alkyl group.

12. The composition of claim 11 , wherein R7 is selected from trifluoromethyl and perfluorobutyl.

13. The composition of claim 11 , wherein the first repeat unit constitutes at least 5 mole % of the copolymer.

14. The composition of claim 11 , wherein the first repeat unit constitutes at least 30 mole % of the copolymer.

15. A composition comprising a terpolymer, the terpolymer comprising:
a first repeat unit comprising a sulfonamide group and a branched linking group, according to Formula (I)

wherein,
R1 and R2 are independently selected from hydrogen and fluorine;
R3 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R4 is hydrogen;
R5 and R6 are methyl; and
R7 is fluorinated C1-C12 alkyl,

a second repeat unit according to the following formula:

wherein,
R40 and R41 are independently selected from hydrogen and fluorine;
R42 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R43 is a C4-C20 tertiary alkyl group, and
a third repeat unit according to the following formula:

wherein,
R32 and R33 are independently selected from hydrogen and fluorine;
R34 is selected from the group consisting of hydrogen, fluorine, methyl, and trifluoromethyl;
R35 is selected from the group consisting of C1-C12 fluorinated alkyl, C6-C20 fluorinated aryl, and C1-C20 fluorinated ether.

16. The composition of claim 15 , wherein R7 is selected from trifluoromethyl and perfluorobutyl.

17. The composition of claim 15 , wherein the first repeat unit constitute at least 5 mole % of the terpolymer.

18. The composition of claim 15 , wherein the first repeat unit constitutes at least 20 mole % of the terpolymer.

Assignees

• IBM
• Central Glass Co Ltd
• Central Class Co Ltd

Inventors

• Sanders Daniel Paul
• Fujiwara Masaki
• Terui Yoshiharu

Classifications

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• C09D133/16 Primary

  Homopolymers or copolymers of esters containing halogen atoms · CPC title

• G03F7/0046 Primary

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/0392

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

• G03F7/0382

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