Composition and method for manufacturing device using same

Patent metadata

Field	Value
Publication number	US-11142495-B2
Application number	US-201716339525-A
Country	US
Kind code	B2
Filing date	Oct 13, 2017
Priority date	Oct 17, 2016
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

An onium salt and a composition having high sensitivity and excellent pattern characteristics such as LWR, which is preferably used for a resist composition for a lithography process using two active energy rays of a first active energy ray such as an electron beam or an extreme ultraviolet and a second active energy ray such as UV.

First claim

The invention claimed is:

1. An onium salt represented by any one selected from a following general formula (1), a following general formula (2), a following general formula (11), and a following general formula (12),

wherein:
in the general formula (1),
each of R 11 and R 12 is any one independently selected from the group consisting of: a linear, branched or cyclic alkyl group which may have a substituent (A), the alkyl group having 1 to 12 carbon atoms; a linear, branched or cyclic alkenyl group which may have the substituent (A), the alkenyl group having 1 to 12 carbon atoms; an aryl group which may have a substituent (B), the aryl group having 6 to 10 carbon atoms; and a heteroaryl group which may have the substituent (A), the heteroaryl group having 4 to 12 carbon atoms;
a number of carbon atoms of each of the alkyl group, the alkenyl group and the heteroaryl group does not include a number of carbon atoms of the substituent (A);
a number of carbon atoms of the aryl group does not include a number of carbon atoms of the substituent (B);
when the aryl group of R 11 and R 12 may have the substituent (B), the substituent (B) is selected from the group consisting of a hydroxy group, a cyano group, a mercapto group, a carboxy group, a carbonyl group, an alkoxy group (—OR), an acyl group (—COR), an alkoxycarbonyl group (—COOR), an amino group, an alkylamino group (—NHR), a dialkylamino group (—N(R) 2 ), a phosphino group, a silyl group, a halogen atom, a trialkylsilyl group (—Si—(R) 3 ); and a main chain of a polymer;
the R in the substituent (B) is the alkyl group having 1 to 20 carbon atoms;
when the alkyl group, the alkenyl group and the heteroaryl group may have the substituent (A), the substituent (A) is selected from the group consisting of group (—OR), an acyl group (—COR), an alkoxycarbonyl group (—COOR), an aryl group (—Ar), an aryloxy group (—OAr), an amino group, an alkylamino group (—NHR), a dialkylamino group (—N(R) 2 ), an arylamino group (—NHAr), a diarylamino group (—N(Ar) 2 ), an N-alkyl-N-arylamino group (—NRAr), a phosphino group, a silyl group, a halogen atom, a trialkylsilyl group (—Si—(R) 3 ), a silyl group substituting at least one alkyl group of the trialkylsilyl group with Ar, an alkylsulfanyl group (—SR), an arylsulfanyl group (—SAr) and a main chain of a polymer;
the R in the substituent (A) is the alkyl group having 1 to 20 carbon atoms;
the Ar in the substituent (A) is the aryl group having 1 to 20 carbon atoms;
any two or more of R 11 , R 12 and an aryl group bonded to a sulfonium group may be bonded each other directly with a single bond, or through any one selected from the group consisting of:

an oxygen atom; a sulfur atom; a nitrogen atom-containing group; and a methylene group to form a ring structure with a sulfur atom bonded to R 11 , R 12 and the aryl group bonded to the sulfonium group are bonded;
at least one methylene group in R 11 and R 12 may be substituted with a divalent hetero atom-containing group;
each of R 13 and R 14 is any one independently selected from the group consisting of: an alkyl group; a hydroxy group; a mercapto group; an alkoxy group; an alkylcarbonyl group; an arylcarbonyl group; an alkoxycarbonyl group; an aryloxycarbonyl group; an arylsulfanylcarbonyl group; an arylsulfanyl group; an alkylsulfanyl group; an aryl group; a heteroaryl group; an aryloxy group; an alkylsulfinyl group; an arylsulfinyl group; an alkylsulfonyl group; an arylsulfonyl group; a (meth)acryloyloxy group; a hydroxy(poly)alkyleneoxy group; an amino group; a cyano group; a nitro group; and a halogen atom, where R 13 and R 14 have 1 to 12 carbon atoms when R 13 and R 14 have a carbon atom, and these groups may have the substituent (A);
the substituent (A) of R 13 and R 14 is the same as the substituent (A) of R 11 and R 12 ,
each of R 15 and R 16 is any one independently selected from the group consisting of: a linear, branched or cyclic alkyl group which may have the substituent (A), the alkyl group having 1 to 12 carbon atoms; a linear, branched or cyclic alkenyl group which may have the substituent (A), the alkenyl group having 1 to 12 carbon atoms; an aryl group which may have the substituent (A), the aryl group having 6 to 14 carbon atoms; and a heteroaryl group which may have the substituent (A), the heteroaryl group having 4 to 12 carbon atoms;
R 15 and R 16 may be bonded each other directly with a single bond or through any one selected from the group consisting of: an oxygen atom; a sulfur atom; and an alkylene group to form a ring structure;
at least one methylene group in R 15 and R 16 may be substituted with a divalent hetero atom-containing group;
the substituent (A) of R 15 and R 16 is the same as the substituent (A) of R 11 and R 12 ,
L 2 is any one selected from the group consisting of: a direct bond; a linear, branched or cyclic alkylene group having 1 to 12 carbon atoms; an alkenylene group having 1 to 12 carbon atoms; an arylene group having 6 to 14 carbon atoms; a heteroarylene group having 4 to 12 carbon atoms; and a group in which these groups are bonded through an oxygen atom, a sulfur atom or a nitrogen atom-containing group;
L 3 is selected from the group consisting of: a direct bond; a methylene group; a sulfur atom; a nitrogen atom-containing group; and an oxygen atom;
Y is an oxygen atom or a sulfur atom;
each of h and i is independently an integer of 1 to 3;
j is an integer of 0 to 4 when his 1, 0 to 6 when h is 2, and 0 to 8 when his 3;
k is an integer of 0 to 5 when i is 1, 0 to 7 when i is 2, and 0 to 9 when i is 3;
X − is a monovalent counter anion;
in the general formula (2),
each of R 13 to R 16 , L 2 , L 3 , Y, h to k and X − is independently selected from a same option as each of R 13 to R 16 , L 2 , L 3 , Y, h to k and X − in the formula (1);
R 17 is any one selected from the group consisting of: an aryl group which may have the substituent (A); and a heteroaryl group which may have the substituent (A); and
R 17 and an aryl group bonded to an iodonium group may be bonded each other to form a ring structure with an iodine atom bonded to R 17 and the aryl group bonded to the iodonium group;
in the general formula (11),
each of R 11 to R 16 , L 2 , Y, h to k and X − is independently selected from a same option as each of R 11 to R 16 , L 2 , Y, h to k and X − in the formula (1); and
each of L 4 and L 5 is any one independently selected from the group consisting of: a direct bond; an alkenylene group having 2 carbon atoms; an alkynylene group having 2 carbon atoms; and a carbonyl group;
in the general formula (12),
each of R 13 to R 17 , L 2 , Y, h to k and X − is independently selected from a same option as each of R 13 to R 17 , L 2 , Y, h to k and X − in the formula (2); and
each of L 4 and L 5 is any one independently selected from the group consisting of: a direct bond; an alkenylene group having 2 carbon atoms; an alkynylene group having 2 carbon atoms; and a carbonyl group.

2. The onium salt of claim 1 , wherein the onium salt is represented by any one selected from the general formula (11) and the general formula (12).

3. The onium salt of claim 1 , wherein the onium salt is represented by a following general formula (6),

where:
in the general formula (6),
each of R 11 to R 16 , X − and Y is independently selected from a same option as each of R 11 to R 16 , X − and Y in the general formula (1);
R 18 is any one selected from the group consisting of: an alkyl group; a hyd

Assignees

• Toyo Gosei Co Ltd

Inventors

• Suga Yusuke
• Enomoto Satoshi

Classifications

• C07C381/12 Primary

  Sulfonium compounds · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• C07D317/22

  etherified · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• G03F7/203

  comprising an imagewise exposure to electromagnetic radiation or corpuscular radiation · CPC title