US 2020/0048191 A1 · COMPOSITION AND METHOD FOR MANUFACTURING DEVICE USING SAME

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.

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, the alkyl group having 1 to 12 carbon atoms;
a linear, branched or cyclic alkenyl group which may have a substituent, the alkenyl group having 1 to 12 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;
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;
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 a substituent;
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 a substituent, the alkyl group having 1 to 12 carbon atoms;
a linear, branched or cyclic alkenyl group which may have a substituent, the alkenyl group having 1 to 12 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;
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;
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 h is 1, 0 to 6 when h is 2, and 0 to 8 when h is 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;
and
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 a substituent;
and a heteroaryl group which may have a substituent;
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.

88 more elements

Description24,202 words

Summary15,569 words

#An embodiment of the present invention relates to a composition. Another embodiment of the present invention relates to a method of manufacturing a device using the composition.

#In recent years, by making full use of a photolithography technique using a photoresist, manufacturing of a display device such as a liquid crystal display (LCD) and an organic EL display (OLED), and formation of semiconductor elements are active. As an active energy ray, i-line having a wavelength of 365 nm, and light such as h-line (405 nm) and g-line (436 nm) having a longer wavelength than i-line are widely used for the packaging of the electronic component and the electronic product.

#Since a device integration has developed, a demand for miniaturization of lithography technology has been increased, a light having a very short wavelength such as KrF excimer laser (wavelength 248 nm), ArF excimer laser (wavelength 193 nm), extreme ultraviolet (EUV, wavelength 13.5 nm) and an electron beam (EB) tends to be used for exposure. Since the lithography techniques using these short wavelength lights, especially EUV or electron beam, can allow manufacturing by single patterning, a demand for a resist composition having high sensitivity to EUV, the electron beam or the like may further increase in the future.

Detailed description8,633 words

#Hereinafter, the present invention will be described in more detail by examples, but the present invention is not limited by these examples at all.

#4-Bromothioanisole (8.0 g) is dissolved in tetrahydrofuran (32 g), and a 1 mol/L THF solution (39 ml) of methylmagnesium bromide is added dropwise thereto at 5° C. or lower. After dropwise addition, a mixture is stirred at 35° C. for 30 minutes to obtain a THF solution of 4-methylsulfanylphenylmagnesium bromide. 4-Fluorobenzoyl chloride (7.0 g) is dissolved in THF (15 g), the THF solution of 4-methylsulfanylphenylmagnesium bromide is added dropwise thereto at 10° C. or lower, and a mixture is stirred at 25° C. for 1 hour. After stirring, 10% by mass of aqueous solution (50 g) of ammonium chloride is added thereto at 20° C. or lower, a mixture is further stirred for 10 minutes, and an organic layer is extracted with ethyl acetate (80 g). An extract is washed with water, and then ethyl acetate and tetrahydrofuran are evaporated to obtain a crude crystal. The crude crystal is recrystallized with ethanol (120 g) to obtain 4-fluoro-4′-methylsulfanylbenzophenone (6.1 g).

#4-Fluoro-4′-methylsulfanylbenzophenone (6.0 g) obtained in Synthesis Example 1 is dissolved in DMF (30 g), thiophenol (3.2 g) and potassium carbonate (4.0 g) are added thereto, and a mixture is stirred at 70° C. for 4 hours. After stirring, pure water (90 g) is added thereto, a mixture is further stirred for 10 minutes, and an organic layer is extracted with toluene (60 g). An extract is washed three times with water, and then toluene is evaporated to obtain a crude crystal. The crude crystal is recrystallized with ethanol (40 g) to obtain 4-methylsulfanyl-4′-phenylsulfanylbenzophenone (5.6 g).

Facts

Application

16/339,525Filed 13 Oct 2017

Priority

JP 2016-20378017 Oct 2016

Published

13 Feb 2020

Term ends

Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07C 381/12
Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00: sulfonium compounds
C07C 43/315
Compounds having [IMAGE cpc-sch-C07C-0958.gif] groups: containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
C07D 317/22
Radicals substituted by singly bound oxygen or sulfur atoms: etherified
C07D 333/76
Condensed with carbocyclic rings or ring systems: dibenzothiophenes

Composition and method for manufacturing device using same

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Composition and method for manufacturing device using same

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Abstract

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Claims15

Description24,202 words

Drawings

Classification16 codes

Life of this patent

Description24,202 words