Method of producing polymeric compound, resist composition and method of forming resist pattern

Patent metadata

Field	Value
Publication number	US-9469712-B2
Application number	US-201414205986-A
Country	US
Kind code	B2
Filing date	Mar 12, 2014
Priority date	Mar 18, 2013
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

A method of producing a copolymer, including copolymerizing a monomer (am0) containing a partial structure represented by formula (am0-1) shown below, a monomer (am1) containing an acid decomposable group which exhibits increased polarity by the action of acid and a monomer (am5) containing an —SO 2 — containing cyclic group in the presence of a nitrogen-containing compound (X) having a conjugated acid with an acid dissociation constant of less than 10 (in the formula, *0 to *4 each represents a valence bond).

First claim

What is claimed is:

1. A method of producing a copolymer, comprising:
copolymerizing a monomer (am0) containing a partial structure represented by formula (am0-1) shown below, a monomer (am1) containing an acid decomposable group which exhibits increased polarity by the action of acid and a monomer (am5) containing an —SO 2 — containing cyclic group in the presence of a nitrogen-containing compound (X) having a conjugated acid with an acid dissociation constant of less than 10:

wherein *0 to *4 each represents a valence bond.

2. The method according to claim 1 , wherein the monomer (am0) is a monomer containing a partial structure represented by general formula (am0-2) shown below:

wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Y 1 represents a single bond or a divalent linking group; *1 to *4 each represents a valence bond.

3. The method according to claim 1 , wherein the monomer (am0) is a monomer represented by general formula (am0-2-1) or (am0-2-2) shown below:

wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Y 1 represents a single bond or a divalent linking group; *2′ and *4′ represent valence bonds which are mutually bonded to form a ring; R 0 represents a hydrogen atom, an alkyl group, an acid dissociable group, a lactone-containing cyclic group, a carbonate-containing cyclic group, a polar group-containing aliphatic hydrocarbon group or an acid non-dissociable cyclic group; n1 represents 0 or 1; and n2 represents 1 or 2.

4. The method according to claim 3 , wherein *2′ and *4′ represent valence bonds which are mutually bonded via an alkylene group which may have a substituent, so as to form a monocyclic group.

5. The method according to claim 4 , wherein the monocyclic group has 4 to 8 atoms.

6. The method according to claim 4 , wherein the substituent is an oxygen atom.

7. The method according to claim 1 , wherein the nitrogen-containing compound (X) is at least one compound selected from the group consisting of a compound represented by general formula (X1) shown below and a compound represented by general formula (X2) shown below:

wherein R 1 to R 3 each independently represents a hydrogen atom, an alkyl group of 1 to 15 carbon atoms which may have a substituent, a fluorinated alkyl group which may have a substituent or an aryl group, provided that two of R 1 to R 3 may be mutually bonded to form a ring, and at least one of R 1 to R 3 represents a fluorinated alkyl group, an aryl group or an aryl group containing a fluorine atom; R 4 is a group which forms an aromatic ring with the nitrogen atom bonded to the R 4 group; R 5 represents an alkyl group of 1 to 15 carbon atoms which may have a substituent, a halogen atom or an aryl group; and y represents an integer of 0 to 5.

8. The method according to claim 7 , wherein, in general formula (X1), at least one of R 1 to R 3 represents an aryl group or an aryl group containing a fluorine atom, and in general formula (X2), R 4 is a group which forms a pyridine ring, a pyrimidine ring, an azepine ring, a pyrazine ring, a quinoline ring, a benzoquinoline ring, an oxazole ring or an isooxazole ring with the nitrogen atom bonded to the R 4 group.

9. The method according to claim 2 , wherein the nitrogen-containing compound (X) is at least one compound selected from the group consisting of a compound represented by general formula (X1) shown below and a compound represented by general formula (X2) shown below:

wherein R 1 to R 3 each independently represents a hydrogen atom, an alkyl group of 1 to 15 carbon atoms which may have a substituent, a fluorinated alkyl group which may have a substituent or an aryl group, provided that two of R 1 to R 3 may be mutually bonded to form a ring, and at least one of R 1 to R 3 represents a fluorinated alkyl group, an aryl group or an aryl group containing a fluorine atom; R 4 is a group which forms an aromatic ring with the nitrogen atom bonded to the R 4 group; R 5 represents an alkyl group of 1 to 15 carbon atoms which may have a substituent, a halogen atom or an aryl group; and y represents an integer of 0 to 5.

10. The method according to claim 9 , wherein in general formula (X1), at least one of R 1 to R 3 represents an aryl group or an aryl group containing a fluorine atom, and in general formula (X2), R 4 is a group which forms a pyridine ring, a pyrimidine ring, an azepine ring, a pyrazine ring, a quinoline ring, a benzoquinoline ring, an oxazole ring or an isooxazole ring with the nitrogen atom bonded to the R 4 group.

11. The method according to claim 3 , wherein the nitrogen-containing compound (X) is at least one compound selected from the group consisting of a compound represented by general formula (X1) shown below and a compound represented by general formula (X2) shown below:

wherein R 1 to R 3 each independently represents a hydrogen atom, an alkyl group of 1 to 15 carbon atoms which may have a substituent, a fluorinated alkyl group which may have a substituent or an aryl group, provided that two of R 1 to R 3 may be mutually bonded to form a ring, and at least one of R 1 to R 3 represents a fluorinated alkyl group, an aryl group or an aryl group containing a fluorine atom; R 4 is a group which forms an aromatic ring with the nitrogen atom bonded to the R 4 group; R 5 represents an alkyl group of 1 to 15 carbon atoms which may have a substituent, a halogen atom or an aryl group; and y represents an integer of 0 to 5.

12. The method according to claim 11 , wherein in general formula (X1), at least one of R 1 to R 3 represents an aryl group or an aryl group containing a fluorine atom, and in general formula (X2), R 4 is a group which forms a pyridine ring, a pyrimidine ring, an azepine ring, a pyrazine ring, a quinoline ring, a benzoquinoline ring, an oxazole ring or an isooxazole ring with the nitrogen atom bonded to the R 4 group.

13. The method according to claim 4 , wherein the nitrogen-containing compound (X) is at least one compound selected from the group consisting of a compound represented by general formula (X1) shown below and a compound represented by general formula (X2) shown below:

wherein R 1 to R 3 each independently represents a hydrogen atom, an alkyl group of 1 to 15 carbon atoms which may have a substituent, a fluorinated alkyl group which may have a substituent or an aryl group, provided that two of R 1 to R 3 may be mutually bonded to form a ring, and at least one of R 1 to R 3 represents a fluorinated alkyl group, an aryl group or an aryl group containing a fluorine atom; R 4 is a group which forms an aromatic ring with the nitrogen atom bonded to the R 4 group; R 5 represents an alkyl group of 1 to 15 carbon atoms which may have a substituent, a halogen atom or an aryl group

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Hirano Tomoyuki
• Utsumi Yoshiyuki
• Tsuchiya Junichi
• Hori Yoichi

Classifications

• C08F224/00 Primary

  Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F218/00; cyclic anhydrides of unsaturated acids C08F220/00, C08F222/00) · CPC title

• C08F228/06

  by a heterocyclic ring containing sulfur · CPC title

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title

• G03F7/0397

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

• C08F216/10

  Carbocyclic compounds · CPC title