Resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-11614688-B2
Application number	US-202016799129-A
Country	US
Kind code	B2
Filing date	Feb 24, 2020
Priority date	Mar 22, 2019
Publication date	Mar 28, 2023
Grant date	Mar 28, 2023

Abstract

A chemically-amplified negative resist composition includes: (A) an acid generator containing an onium salt (s) shown by the following formula(e) (A-1) and/or (A-2); and (B) a base polymer containing repeating units shown by the following formulae (B1) and (B2). Thus, the present invention provides: a chemically-amplified negative resist composition which provides a pattern with high sensitivity, low LWR and CDU, and favorable profile; and a resist patterning process using the composition.

First claim

The invention claimed is:

1. A chemically-amplified negative resist composition comprising:
(A) an acid generator containing an onium salt(s) shown by the following formula(e) (A-1) and/or (A-2); and
(B) a base polymer containing repeating units shown by the following formulae (B1) and (B2),

wherein R 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a hydroxy group, an amino group, a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms optionally containing a fluorine atom, a chlorine atom, a bromine atom, a hydroxy group, an amino group, or an alkoxy group, an alkoxy group having 1 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, —NR 7 —C(═O)—R 8 , or —NR 7 —C(═O)—O—R 8 ; R 7 represents a hydrogen atom or a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms optionally containing a halogen atom, a hydroxy group, an alkoxy group, an acyl group, or an acyloxy group; R 8 represents a linear, branched, or cyclic alkyl group having 1 to 16 carbon atoms or alkenyl group having 2 to 16 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and optionally contains a halogen atom, a hydroxy group, an alkoxy group, an acyl group, or an acyloxy group; Z represents a single bond or a divalent linking group having 1 to 20 carbon atoms when “p” is 1, or a trivalent or tetravalent linking group having 1 to 20 carbon atoms when “p” is 2 or 3, the linking groups optionally containing an oxygen atom, a sulfur atom, or a nitrogen atom; Rf 1 to Rf 4 each independently represent a hydrogen atom, a fluorine atom, or a trifluoromethyl group, at least one of Rf 1 to Rf 4 is a fluorine atom or a trifluoromethyl group, and Rf 1 and Rf 2 optionally bond with each other to form a carbonyl group; R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a linear, branched, or cyclic alkyl group or oxoalkyl group having 1 to 12 carbon atoms, a linear, branched, or cyclic alkenyl group or oxoalkenyl group having 2 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group or aryloxoalkyl group having 7 to 12 carbon atoms, and some or all of hydrogen atoms of these groups are optionally substituted with a hydroxy group, a carboxyl group, a halogen atom, a cyano group, an amide group, a nitro group, a sultone group, a sulfone group, or a sulfonium salt-containing group, and carbon atoms of these groups are optionally interposed by an ether group, an ester group, a carbonyl group, a carbonate group, or a sulfonic acid ester group; R 2 and R 3 optionally bond with each other to form a ring with a sulfur atom bonded to R 2 and R 3 ; “m” represents an integer of 1 to 5; “n” represents an integer of 0 to 3; and “p” represents an integer of 1 to 3,

wherein R A represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group; R 11 and R 12 each independently represent a halogen atom, an acyloxy group having 2 to 8 carbon atoms optionally halogen-substituted, an alkyl group having 1 to 6 carbon atoms optionally halogen-substituted, or an alkoxy group having 1 to 6 carbon atoms optionally halogen-substituted; A 1 represents a single bond or a linear, branched, or cyclic alkylene group having 1 to 10 carbon atoms and optionally having an ether bond interposed in a carbon-carbon bond; W 1 represents a hydrogen atom, a monovalent aromatic group optionally having a substituent, or an aliphatic monovalent hydrocarbon group having 1 to 10 carbon atoms optionally having an ether bond, a carbonyl group, or a carbonyloxy group interposed in a carbon-carbon bond; Rx and Ry each independently represent a hydrogen atom, an alkyl group having 1 to 15 carbon atoms optionally substituted with a hydroxy group or an alkoxy group, or a monovalent aromatic group optionally having a substituent, given that not both of Rx and Ry are hydrogen atoms simultaneously, and Rx and Ry optionally bond with each other to form a ring with a carbon atom bonded to Rx and Ry; t 1 represents 0 or 1; x 1 represents an integer of 0 to 2; “a” represents an integer satisfying 0≤a≤5+2x 1 −b; “c” represents an integer satisfying 0≤c≤5+2x 1 −d; and “b” and “d” each represent an integer of 1 to 3.

2. The chemically-amplified negative resist composition according to claim 1 , wherein the base polymer further contains at least one repeating unit selected from a repeating unit shown by the following formula (B3) and a repeating unit shown by the following formula (B4):

wherein R 13 and R 14 each independently represent a hydroxy group, a halogen atom, an acetoxy group, an alkyl group having 1 to 8 carbon atoms optionally halogen-substituted, a primary alkoxy group having 1 to 8 carbon atoms optionally halogen-substituted, a secondary alkoxy group having 2 to 8 carbon atoms, an acyloxy group having 2 to 8 carbon atoms optionally halogen-substituted, or an alkylcarbonyloxy group having 2 to 8 carbon atoms optionally halogen-substituted; and “e” and “f” each independently represent an integer of 0 to 4.

3. The chemically-amplified negative resist composition according to claim 2 , wherein the base polymer contains a repeating unit shown by the following formula (B5) and a repeating unit shown by the following formula (B6):

wherein R A , Rx, Ry, W 1 , “b”, and “d” are as defined above. a crosslinking agent.

4. The chemically-amplified negative resist composition according to claim 3 , further comprising (C) a crosslinking agent.

5. A resist patterning process using the chemically-amplified negative resist composition according to claim 4 , comprising steps of:
forming a resist film by using the chemically-amplified negative resist composition on a substrate to be processed;
irradiating the resist film with a high energy beam to form a pattern; and
developing the resist film by using an alkaline developer.

6. A resist patterning process using the chemically-amplified negative resist composition according to claim 3 , comprising steps of:
forming a resist film by using the chemically-amplified negative resist composition on a substrate to be processed;
irradiating the resist film with a high energy beam to form a pattern; and
developing the resist film by using an alkaline developer.

7. The chemically-amplified negative resist composition according to claim 2 , further comprising (C) a crosslinking agent.

8. A resist patterning process using the chemically-amplified negative resist composition according to claim 7 , comprising steps of:
forming a resist film by using the chemically-amplified negative resist composition on a substrate to be processed;
irradiating the resist film with a high energy beam to form a pattern; and
developing the resist film by using an alkaline developer.

9. A resist patterning process using the chemically-amplified negative resist composition according to claim 2 , comprising steps of:
forming a resist film by using the chemically-amplified negative resist composition on a substrate to be processed;
irradiating the resist film with a high energy beam to form a pattern; and
developing the resist film by using an alkaline developer.

10. The resist patterning process according to claim 9 , wherein the high energy beam is an electron beam or an extre

Assignees

• Shinetsu Chemical Co

Inventors

• Taniguchi Ryosuke
• Watanabe Satoshi
• Fujiwara Takayuki
• Inoue Naoya

Classifications

• C08F212/24

  Phenols or alcohols · CPC title

• G03F7/162

  Coating on a rotating support, e.g. using a whirler or a spinner · CPC title

• G03F7/033

  the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers · CPC title

• G03F7/322

  Aqueous alkaline compositions · CPC title

• G03F7/0382 Primary

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