Polymer compound, positive resist composition, laminate, and resist patterning process

Patent metadata

Field	Value
Publication number	US-9944738-B2
Application number	US-201615206684-A
Country	US
Kind code	B2
Filing date	Jul 11, 2016
Priority date	Aug 5, 2015
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

A polymer compound containing a repeating unit shown by the formula (1c) and one or more repeating units selected from a repeating unit shown by the formula (2) and a repeating unit shown by the formula (3),

wherein M b + represents a sulfonium cation shown by the formula (a) or an iodonium cation shown by the formula (b),

This polymer compound is suitable as a base resin of a resist composition capable of forming a resist film that allows pattern formation with extremely high resolution, small LER, and excellent rectangularity.

First claim

The invention claimed is:

1. A polymer compound comprising a repeating unit shown by the formula (1c) and at least one repeating unit selected from the group consisting of a repeating unit shown by the formula (2) and a repeating unit shown by the formula (3),

wherein R 1 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group; A represents a single bond or a linear divalent hydrocarbon group having 1 to 30 carbon atoms or a branched or cyclic divalent hydrocarbon group having 3 to 30 carbon atoms, in which the hydrocarbon group may contain a heteroatom, and a part or all of hydrogen atoms in the hydrocarbon group may be substituted with a group containing a heteroatom; “n” represents 0 or 1, provided that “n” is 0 when A is a single bond; and M b + represents a sulfonium cation shown by the formula (a) or an iodonium cation shown by the formula (b),

wherein R 100 , R 200 , R 300 , R 400 , and R 500 independently represent a heteroatom or a linear monovalent hydrocarbon group having 1 to 20 carbon atoms or a branched or cyclic monovalent hydrocarbon group having 3 to 20 carbon atoms, in which the hydrocarbon group may contain a heteroatom, and a part or all of hydrogen atoms in the hydrocarbon group may be substituted with a group containing a heteroatom; and two or more of R 100 , R 200 , and R 300 may be bonded to each other to form a ring together with the sulfur atom in the formula,

wherein G represents a single bond or an alkylene group having 1 to 10 carbon atoms and optionally containing an ether oxygen atom; D represents a single bond, or a linear aliphatic hydrocarbon group having 1 to 10 carbon atoms or a branched or cyclic aliphatic hydrocarbon group having 3 to 10 carbon atoms with a valency of v+1, in which the aliphatic hydrocarbon group may contain an ether oxygen atom, a carbonyl group, or a carbonyloxy group, and a part or all of hydrogen atoms in the aliphatic hydrocarbon may be substituted with a fluorine atom; R 1 is as defined above; R 2 represents a hydrogen atom, a halogen atom, a linear acyloxy group having 2 to 8 carbon atoms, a branched or cyclic acyloxy group having 3 to 8 carbon atoms, a linear alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, a linear alkoxy group having 1 to 6 carbon atoms, or a branched or cyclic alkoxy group having 3 to 6 carbon atoms, in which a part or all of hydrogen atoms in the acyloxy group, the alkyl group, and the alkoxy group may be substituted with halogen; Rf 1 and Rf 2 each represent an alkyl group having 1 to 6 carbon atoms and containing at least one fluorine atom, and Rf 1 may bond to D to form a ring together with the carbon atom to which these groups are bonded; “g” represents an integer of 0 to 3; “h” and “v” each represent 1 or 2; “p” and “r” each represent 0 or 1, provided that “p” is 1 and G is a single bond when “r” is 0; “t” and “u” each represent an integer of 0 to 2; “b” represents an integer of (5+2t−g); and “c” represents an integer of (5+2u−h).

2. The polymer compound according to claim 1 , further comprising at least one repeating unit selected from the group consisting of a repeating unit shown by the formula (4) and a repeating unit shown by the formula (5),

wherein R 3 and R 4 each represent a hydrogen atom, a halogen atom, a linear acyloxy group having 2 to 8 carbon atoms, a branched or cyclic acyloxy group having 3 to 8 carbon atoms, a linear alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, a linear alkoxy group having 1 to 6 carbon atoms, or a branched or cyclic alkoxy group having 3 to 6 carbon atoms, in which a part or all of hydrogen atoms in the acyloxy group, the alkyl group, and the alkoxy group may be substituted with halogen; “i” and “j” represent an integer of 0 to 3; “d” represents an integer of 0 to 5; and “e” represents an integer of 0 to 3.

3. The polymer compound according to claim 1 , further comprising a repeating unit shown by the formula (U-2),

wherein R 1 , R 2 , G, “p”, and “t” are as defined above; “x” represents 0 or 1; “y” represents an integer of 1 to 3; “q” represents an integer of (5+2t−y); X represents a hydrogen atom or an acid-labile group, provided that at least one X is an acid-labile group.

4. The polymer compound according to claim 2 , further comprising a repeating unit shown by the formula (U-2),

wherein R 1 , R 2 , G, “p”, and “t” are as defined above; “x” represents 0 or 1; “y” represents an integer of 1 to 3; “q” represents an integer of (5+2t−y); X represents a hydrogen atom or an acid-labile group, provided that at least one X is an acid-labile group.

5. A positive resist composition comprising the polymer compound according to claim 1 .

6. A positive resist composition comprising the polymer compound according to claim 2 .

7. A positive resist composition comprising the polymer compound according to claim 3 .

8. A positive resist composition comprising the polymer compound according claim 4 .

9. The positive resist composition according to claim 5 , further comprising a compound capable of generating an acid by irradiation with a high energy beam.

10. The positive resist composition according to claim 6 , further comprising a compound capable of generating an acid by irradiation with a high energy beam.

11. The positive resist composition according to claim 7 , further comprising a compound capable of generating an acid by irradiation with a high energy beam.

12. The positive resist composition according to claim 8 , further comprising a compound capable of generating an acid by irradiation with a high energy beam.

13. The positive resist composition according to claim 5 , further comprising a polymer compound that contains a repeating units shown by the formula (6) and a repeating unit containing at least one fluorine atom,

wherein R 5 represents a hydrogen atom or a methyl group; R 6 and R 7 represent a hydrogen atom or a linear, branched, or cyclic hydrocarbon group having 1 to 5 carbon atoms and optionally containing a heteroatom; X 1 represents a single bond, —C(═O)O—, or —C(═O)NH—; “z” represents 0 or 1; “m” represents an integer of 1 to 3; and “s” represents an integer of (5+2z−m).

14. The positive resist composition according to claim 9 , further comprising a polymer compound that contains a repeating units shown by the formula (6) and a repeating unit containing at least one fluorine atom,

wherein R 5 represents a hydrogen atom or a methyl group; R 6 and R 7 represent a hydrogen atom or a linear, branched, or cyclic hydrocarbon group having 1 to 5 carbon atoms and optionally containing a heteroatom; X 1 represents a single bond, —C(═O)O—, or —C(═O)NH—; “z” represents 0 or 1; “m” represents an integer of

Assignees

• Shinetsu Chemical Co

Inventors

• Domon Daisuke
• Watanabe Satoshi
• Masunaga Keiichi
• Kotake Masaaki

Classifications

• C08F20/38 Primary

  Esters containing sulfur · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/093

  characterised by antistatic means, e.g. for charge depletion · CPC title

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title