DEPROTECTION METHOD OF PROTECTED POLYMER

• US 20110086986A1
• Filed: 10/11/2010
• Published: 04/14/2011
• Est. Priority Date: 10/13/2009
• Status: Active Grant

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Watanabe, Satoshi, Domon, Daisuke, Masunaga, Keiichi, Watanabe, Takeru
• Granted Patent: US 8,273,830 B2
• Time in Patent Office: Days
• US Class Current: 525/380
• CPC Class Codes: C08F 212/18 Chlorine
• CPC Class Codes: C08F 212/22 Oxygen
• CPC Class Codes: C08F 212/32 containing two or more rings
• CPC Class Codes: C08F 220/18 with acrylic or methacrylic acids
• CPC Class Codes: C08F 220/1804 C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
• CPC Class Codes: C08F 220/1807 C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
• CPC Class Codes: C08F 220/1809 C9-(meth)acrylate
• CPC Class Codes: C08F 220/30 containing aromatic rings in the alcohol moiety
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 8/12 Hydrolysis
• CPC Class Codes: G03F 7/0382 the macromolecular compound being present in a chemically amplified negative photoresist composition
• CPC Class Codes: G03F 7/0392 the macromolecular compound being present in a chemically amplified positive photoresist composition
• CPC Class Codes: G03F 7/0397 the macromolecular compound having an alicyclic moiety in a side chain

Abstract

Provided is a method of deprotecting a protected polymer, the method being capable of, in the deprotection reaction of a polymer comprising a unit structure having a phenolic hydroxyl group protected with an acyl group, deacylating the polymer in a short period of time while maintaining the other structure, and being capable of taking out the deacylated polymer while highly suppressing contamination of the deacylated polymer with a substance other than the polymer taking part in the reaction. More specifically, provided is a method of deprotecting a protected polymer comprising at least a step of dissolving in an organic solvent the protected polymer comprising at least a unit structure having a phenolic hydroxyl group protected with an acyl group and a deprotecting reagent selected from primary or secondary amine compounds each having a ClogP value of 1.00 or less with the proviso that in the secondary amine compound, neither of the two carbon atoms coupled to the nitrogen atom of the amino group is tertiary. The primary or secondary amine compounds are each represented preferably by HNR¹_2-nR²_n (1).

Claims

1. A method of deprotecting a protected polymer, comprising at least a step of dissolving in an organic solvent the protected polymer comprising at least a unit structure having a phenolic hydroxyl group protected with an acyl group and a deprotecting reagent selected from the group consisting of primary and secondary amine compounds each having a ClogP value of 1.00 or less with the proviso that in the secondary amine compound, neither of the two carbon atoms coupled to the nitrogen atom of the amino group is tertiary, to deprotect the protected polymer.

2. The method of deprotecting a protected polymer according to claim 1, wherein said primary amine and secondary amine compounds are represented by the formula (1):

HNR¹_2-nR²_n 

 

(1)

wherein R¹ represents a hydrogen atom or a linear, branched or cyclic C_1-6 alkyl group, R² independently represents a linear, branched or cyclic C_2-7 alkyl group comprising at least one oxygen atom or at least one nitrogen atom, two R²s may be coupled to each other to form a cyclic structure comprising at least one oxygen atom and/or at least one nitrogen atom, and n stands for 1 or 2.

3. The method of deprotecting a protected polymer according to claim 2, wherein a part or all of R²_n in the formula (1) has a structure represented by the following formula (2):

4. The method of deprotecting a protected polymer according to claim 1, wherein said protected polymer further comprises a unit structure having an ester structure derived from an aliphatic alcohol.

5. A method of producing a base polymer for chemically amplified resist, comprising a step of:

carrying out the method of deprotecting as claimed in claim 1.

6. The method of deprotecting a protected polymer according to claim 2, wherein said protected polymer further comprises a unit structure having an ester structure derived from an aliphatic alcohol.

7. The method of deprotecting a protected polymer according to claim 3, wherein said protected polymer further comprises a unit structure having an ester structure derived from an aliphatic alcohol.

8. A method of producing a base polymer for chemically amplified resist, comprising a step of:

carrying out the method of deprotecting as claimed in claim 2.

9. A method of producing a base polymer for chemically amplified resist, comprising a step of:

carrying out the method of deprotecting as claimed in claim 3.

10. A method of producing a base polymer for chemically amplified resist, comprising a step of:

carrying out the method of deprotecting as claimed in claim 4.