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US 11,142,495 B2Granted
Composition and method for manufacturing device using same
AssigneeToyo Gosei Co., Ltd.
InventorsYusuke Suga, Satoshi Enomoto
Life of this patent
Estimating the term…
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.
Claims15
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 R11 and R12 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 R11 and R12 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 R11, R12 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 R11, R12 and the aryl group bonded to the sulfonium group are bonded;
- at least one methylene group in R11 and R12 may be substituted with a divalent hetero atom-containing group;
- each of R13 and R14 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 R13 and R14 have 1 to 12 carbon atoms when R13 and R14 have a carbon atom, and these groups may have the substituent (A);
- the substituent (A) of R13 and R14 is the same as the substituent (A) of R11 and R12,
- each of R15 and R16 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;
- R15 and R16 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 R15 and R16 may be substituted with a divalent hetero atom-containing group;
- the substituent (A) of R15 and R16 is the same as the substituent (A) of R11 and R12,
- L2 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;
- L3 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 R13 to R16, L2, L3, Y, h to k and X− is independently selected from a same option as each of R13 to R16, L2, L3, Y, h to k and X− in the formula (1);
- R17 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
- R17 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 R17 and the aryl group bonded to the iodonium group;
- in the general formula (11),
- each of R11 to R16, L2, Y, h to k and X− is independently selected from a same option as each of R11 to R16, L2, Y, h to k and X− in the formula (1);
- and
- each of L4 and L5 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 R13 to R17, L2, Y, h to k and X− is independently selected from a same option as each of R13 to R17, L2, Y, h to k and X− in the formula (2);
- and
- each of L4 and L5 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.
96 more elements
Dependencies are inferred from the claim text.