Radiation-sensitive resin composition and resist pattern-forming method

Patent metadata

Field	Value
Publication number	US-2016202608-A1
Application number	US-201615079753-A
Country	US
Kind code	A1
Filing date	Mar 24, 2016
Priority date	Sep 26, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

A radiation-sensitive resin composition comprises: a polymer, and a radiation-sensitive acid generator. The polymer comprises a structural unit comprising: an acid-labile group; and an oxoacid group or phenolic hydroxyl group protected by the acid-labile group. The acid-labile group is represented by formula (1). R 1 and R 2 each independently represent a divalent organic group having 1 to 20 carbon atoms. R 3 represents a monovalent group having 1 to 40 atoms and having at least one selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom. * denotes a binding site to the oxy group in the oxoacid group or phenolic hydroxyl group protected.

First claim

1 . A radiation-sensitive resin composition comprising:
a polymer comprising a structural unit comprising: an acid-labile group; and an oxoacid group or phenolic hydroxyl group protected by the acid-labile group; and a radiation-sensitive acid generator, wherein the acid-labile group is represented by formula (1):

wherein, in the formula (1),
R 1 and R 2 each independently represent a divalent organic group having 1 to 20 carbon atoms;
R 3 represents a monovalent group having 1 to 40 atoms and comprising an oxygen atom, a sulfur atom, a nitrogen atom or a combination thereof;
k is an integer of 0 to 4;
n is an integer of 1 to 13;
R 4 represents a halogen atom, a monovalent hydrocarbon group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms;
m is an integer of 0 to 12,
wherein a sum of m and n is no greater than 13,
in a case where n is no less than 2, a plurality of R 2 s are identical or different, and a plurality of R 3 s are identical or different, and
in a case where m is no less than 2, a plurality of R 4 s are identical or different; and

* denotes a binding site to the oxy group in the oxoacid group or phenolic hydroxyl group protected.

2 . The radiation-sensitive resin composition according to claim 1 , wherein the divalent organic group represented by R 1 in the formula (1) is represented by any one of formulae (a-1) to (a-3):

wherein,
in the formulae (a-1) to (a-3),
* denotes a binding site to the oxy group in the oxoacid group or phenolic hydroxyl group protected; and
** denotes a site bound to the aromatic ring in the formula (1),

in the formula (a-1),
R 5 and R 6 each independently represent a monovalent chain hydrocarbon group having 1 to 10 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 10 carbon atoms, a group having —COO— between two adjacent carbon atoms in the chain hydrocarbon group or the alicyclic hydrocarbon group, or a group obtained by substituting a part of hydrogen atoms included in the chain hydrocarbon group or the alicyclic hydrocarbon group with a fluorine atom or a hydroxy group; and
R 7 represents a single bond or a divalent hydrocarbon group having 1 to 18 carbon atoms,

in the formula (a-2),
R 8 represents a substituted or unsubstituted divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and

in the formula (a-3),
R 9 represents a substituted or unsubstituted tetravalent alicyclic hydrocarbon group having 5 to 20 ring atoms and having a double bond; and
R a and R b each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms.

3 . The radiation-sensitive resin composition according to claim 1 , wherein in the formula (1),
the monovalent group represented by R 3 is —OH, —COR, —COOR, —OCOCOOR or —CONR 2 ; and R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms.

4 . The radiation-sensitive resin composition according to claim 1 , wherein in the formula (1), the divalent organic group represented by R 2 is a substituted or unsubstituted alkanylidene group or a substituted or unsubstituted cycloalkanylidene group.

5 . The radiation-sensitive resin composition according to claim 1 , wherein the structural unit is represented by any one of formulae (1-1) to (1-3):

wherein, in the formulae (1-1) to (1-3),
Z represents the acid-labile group represented by the formula (1),

in the formula (1-1),
R 10 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group,

in the formula (1-2),
R 11 represents a hydrogen atom or a methyl group;
R 12 represents a single bond, —O—, —COO— or —COHN—;
R 13 represents a monovalent organic group having 1 to 10 carbon atoms; and
a is an integer of 0 to 4, wherein
in a case where a is no less than 2, a plurality of R 13 s are identical or different,

in the formula (1-3),
R 14 represents a hydrogen atom or a methyl group;
R 15 , R 16 and R 17 each independently represent a hydrogen atom, a halogen atom, a hydroxy group or a monovalent organic group having 1 to 20 carbon atoms, or at least two of one or more R 15 (s), one or more R 16 (s) and R 17 optionally taken together represent a ring structure having 3 to 20 ring atoms together with the carbon atom to which the at least two bond;
b is an integer of 1 to 4,
wherein in a case where b is no less than 2, a plurality of R 15 s are identical or different, and a plurality of R 16 s are identical or different;

R 18 represents a single bond or a divalent organic group having 1 to 20 carbon atoms, or R 17 and R 18 optionally taken together represent a ring structure having 3 to 20 ring atoms together with the carbon atom to which R 17 and R 18 bond.

6 . A resist pattern-forming method comprising:
applying the radiation-sensitive resin composition according to claim 1 directly or indirectly on a substrate to form a resist film; exposing the resist film; and developing the resist film exposed.

7 . The resist pattern-forming method according to claim 6 , wherein a radioactive ray used in the exposing is a KrF excimer laser beam, an electron beam or an extreme ultraviolet ray.

Assignees

• Jsr Corp

Inventors

• Namai Hayato

Classifications

• H10P76/20

  of masks comprising organic materials · 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

• G03F7/322

  Aqueous alkaline compositions · CPC title

• G03F7/2059

  using a scanning corpuscular radiation beam, e.g. an electron beam · CPC title

• G03F7/039 Primary

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