Polymer, resist composition containing polymer, and method for manufacturing device using same

Patent metadata

Field	Value
Publication number	US-10781276-B2
Application number	US-201615763600-A
Country	US
Kind code	B2
Filing date	Sep 29, 2016
Priority date	Oct 1, 2015
Publication date	Sep 22, 2020
Grant date	Sep 22, 2020

Abstract

An object of the present invention is to provide a polymer used for a resist composition having high absorption efficiency for a particle beam or an electromagnetic wave, and excellence in sensitivity, resolution and pattern performance characteristics, and provide a resist composition containing the polymer and a method of manufacturing a device using thereof.
The polymer comprises: a unit A; and a unit B, wherein the unit A has an onium salt structure and generates a first radical by irradiation with a particle beam or an electromagnetic wave, the unit B has a radical generating structure containing at least one multiple bond which is between a carbon atom and a carbon atom or between a carbon atom and a heteroatom, and generates a second radical by irradiation with a particle beam or an electromagnetic wave, and the multiple bond is not one contained in a benzenoid aromatic.

First claim

The invention claimed is:

1. A polymer, comprising:
a unit A; and
a unit B,
wherein: the unit A has an onium salt structure and generates a first radical by irradiation with a particle beam or an electromagnetic wave;
the unit B has a radical generating structure containing at least one multiple bond selected from the group consisting of: a multiple bond between a carbon atom and a carbon atom; and a multiple bond between a carbon atom and a heteroatom;
the unit B generates a second radical by irradiation with a particle beam or an electromagnetic wave;
the multiple bond in the radical generating structure is not a multiple bond contained in a benzenoid aromatic;
the polymer does not comprise a unit having an acid dissociable group whose solubility in a water-soluble developer is enhanced by an acid; and
the unit B is represented by at least one of following general formulas (III) to (V),

wherein, in the general formulas (III) to (V),
R 1 is any one selected from the group consisting of:

a hydrogen atom;
a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms; and
a linear, branched or cyclic alkenyl group having 1 to 6 carbon atoms, and
where at least one hydrogen atom in the alkyl group and the alkenyl group in R 1 may be substituted with a fluorine atom;
L is any one selected from the group consisting of: a carbonyloxy group, a phenylenediyl group, a naphthalenediyl group, a phenylenediyloxy group, a naphthalenediyloxy group, a phenylenediylcarbonyloxy group, a naphthalenediylcarbonyloxy group, a phenylenediyloxycarbonyl group and a naphthalenediyloxycarbonyl group;
Sp is any one selected from the group consisting of:

a direct bond;
a linear, branched or cyclic alkylene group which may have a substituent, the alkylene group having 1 to 6 carbon atoms; and
a linear, branched or cyclic alkenylene group which may have a substituent, the alkenylene group having 1 to 6 carbon atoms, and
where at least one methylene group in the Sp may be substituted with a divalent heteroatom-containing group;
each R 3 is independently any one selected from the group consisting of:

a hydrogen atom;
a hydroxy group;
—R a , where R a is a linear, branched or cyclic alkyl group which may have a substituent, the alkyl group having 1 to 12 carbon atoms, and at least one methylene group in R a may be substituted with a divalent heteroatom-containing group;
—OR a ;
a group where at least one carbon-carbon single bond in R a is substituted with a carbon-carbon double bond; and
—R b , where R b is an aryl group which may have a substituent, the aryl group having 6 to 14 carbon atoms, or R b is a heteroaryl group which may have a substituent, the heteroaryl group having 4 to 12 carbon atoms,
where two of R 3 may form a ring structure with each other through a direct single bond, or any one selected from the group consisting of an oxygen atom, a sulfur atom and a methylene group;
R 4 is any one selected from the group consisting of: —R a ; —R b ; —OR a ; —SR a ; —OR b ; —SR b ; —OC(═O)R a ; —OC(═O)R b ; —C(═O)OR a ; —C(═O)OR b ; —OC(═O)OR a ; —OC(═O)OR b ; —NHC(═O)R a ; —NR a C(═O)R a ; —NHC(═O)R b ; —NR b C(═O)R b ; —NR a C(═O)R b ; —NR b C(═O)R a ; —N(R a ) 2 ; —N(R b ) 2 ; —N(R a )(R b ); —SO 3 R a ; —SO 3 R b ; —SO 2 R a ; —SO 2 R b ; a group where at least one carbon-carbon single bond in R a is substituted with a carbon-carbon double bond; and a nitro group,
n 1 is an integer of 1 to 3, m 1 is an integer of 0 to 4 when n 1 is 1, m 1 is an integer of 0 to 6 when n 1 is 2, and m 1 is 0 to 8 when n 1 is 3; and
R 5 is any one selected from the group consisting of:

a linear, branched or cyclic alkylene group which may have a substituent, the alkylene group having 1 to 12 carbon atoms;
a linear, branched or cyclic alkyleneoxy group which may have a substituent, the alkyleneoxy group having 1 to 12 carbon atoms;
a linear, branched or cyclic alkenylene group which may have a substituent, the alkenylene group having 1 to 12 carbon atoms;
a linear, branched or cyclic alkenyleneoxy group which may have a substituent, the alkenyleneoxy group having 1 to 12 carbon atoms;
an arylene group which may have a substituent, the arylene group having 6 to 14 carbon atoms; and
a heteroarylene group which may have a substituent, the heteroarylene group having 4 to 12 carbon atoms, and
where at least one methylene group in R 5 may be substituted with a divalent heteroatom-containing group.

2. The polymer of claim 1 , wherein the unit A is represented by a following general formula (I),

wherein, in the general formula (I), M + is a sulfonium ion or an iodonium ion,
X − is a monovalent anion,
L is any one selected from the group consisting of: a carbonyloxy group, a phenylenediyl group, a naphthalenediyl group, a phenylenediyloxy group, a naphthalenediyloxy group, a phenylenediylcarbonyloxy group, a naphthalenediylcarbonyloxy group, a phenylenediyloxycarbonyl group and a naphthalenediyloxycarbonyl group,
Sp is any one selected from the group consisting of:

a direct bond;
a linear, branched or cyclic alkylene group which may have a substituent, the alkylene group having 1 to 6 carbon atoms; and
a linear, branched or cyclic alkenylene group which may have a substituent, the alkenylene group having 1 to 6 carbon atoms, and
where at least one methylene group in the Sp may be substituted with a divalent heteroatom-containing group, and
R 1 is any one selected from the group consisting of:

a hydrogen atom;
a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms; and
a linear, branched or cyclic alkenyl group having 1 to 6 carbon atoms, and
where at least one hydrogen atom in the alkyl group and the alkenyl group in R 1 may be substituted with a fluorine atom.

3. The polymer of claim 2 , wherein the unit A is represented by a following formula (II),

wherein, in the general formula (II), R 1 , L, Sp and X − are the same as those in the general formula (I),
R 2a is any one selected from the group consisting of:

a linear, branched or cyclic alkylene group which may have a substituent, the alkylene group having 1 to 6 carbon atoms;
a linear, branched or cyclic alkenylene group which may have a substituent, the alkenylene group having 1 to 6 carbon atoms;
an arylene group which may have a substituent, the arylene group having 6 to 14 carbon atoms;
a heteroarylene group which may have a substituent, the heteroarylene group having 4 to 12 carbon atoms; and
a direct bond, and
where at least one methylene group in R 2a may be substituted with a divalent heteroatom-containing group, and
each of R 2b is independently any one selected from the group consisting of:

a linear, branched or cyclic alkyl group which may have a substituent, the alkyl group having 1 to 6 carbon atoms;
a linear, branched or cyclic alkenyl group which may have a substituent, the alkenyl group having 1 to 6 carbon atoms;
an aryl group which may have a substituent, the aryl group having 6 to 14 carbon atoms; and
a heteroaryl group which may have a substituent, the heteroaryl group having 4 to 12 carbon atoms, and
where at least one methylene group in R 2b may be substituted with a divalent heteroatom-containing group, and two selected from R

Assignees

• Toyo Gosei Co Ltd

Inventors

• Enomoto Satoshi
• Yoshino Takumi

Classifications

• C08F220/38 Primary

  Esters containing sulfur · CPC title

• C08F220/303

  and one or more carboxylic moieties in the chain · CPC title

• C08F220/302

  and two or more oxygen atoms in the alcohol moiety · CPC title

• C08F212/22

  Oxygen · CPC title

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title