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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 11953,827
- Publication Date: April 09, 2024
- Appl. No: 16/858092
- Application Filed: April 24, 2020
- Assignees: Shin-Etsu Chemical Co., Ltd. (Tokyo, JP)
- Claim: 1. A molecular resist composition comprising: (A) a betaine type onium compound having a sulfonium cation moiety and a sulfonate anion moiety in a common molecule, the sulfonium cation moiety having a sulfur atom and a phenyl group substituted with an acid labile group of acetal form having the following formula (A′), the phenyl group being attached to the sulfur atom, and (B) an organic solvent, the resist composition being free of a base resin, [chemical expression included] wherein L 3 and L 4 are each independently a single bond, ether bond, ester bond, sulfonate bond, carbonate bond or carbamate bond, X L2 is a single bond or a C 1 -C 40 divalent hydrocarbon group which may contain a heteroatom, R a is hydrogen or a C 1 -C 20 monovalent hydrocarbon group which may contain a heteroatom, R b and R c are each independently a C 1 -C 40 monovalent hydrocarbon group which may contain a heteroatom, R b and R c may bond together to form a ring with the oxygen atoms to which they are attached and the intervening carbon atom.
- Claim: 2. The molecular resist composition of claim 1 wherein the betaine type onium compound has the formula (A): [chemical expression included] wherein a is an integer of 1 to 5, k is an integer of 0 to 3, Q 1 and Q 2 are each independently fluorine or a C 1 -C 6 fluoroalkyl group, Q 3 and Q 4 are each independently hydrogen, fluorine or a C 1 -C 6 fluoroalkyl group, L 1 and L 2 are each independently a single bond, ether bond, ester bond, sulfonate bond, carbonate bond, or carbamate bond, X L1 is a single bond or a C 1 -C 40 divalent hydrocarbon group which may contain a heteroatom, R 1 is an acid labile group of acetal form having the formula (A′), in case of a ≥2, R 1 may be identical or different and two R 1 may bond together to form a ring with the atoms to which they are attached, R 2 is a C 1 -C 50 monovalent hydrocarbon group which may contain a heteroatom, R 3 is a C 1 -C 50 divalent hydrocarbon group which may contain a heteroatom, any two of the phenyl group to which R 1 is attached, R 2 , and R 3 may bond together to form a ring with the sulfur atom to which they are attached.
- Claim: 3. The molecular resist composition of claim 2 wherein the betaine type onium compound has the formula (A-1): [chemical expression included] wherein a, k, Q 1 to Q 4 , L 1 , L 2 , X L1 , and R 1 are as defined above, R 2A and R 3A are each independently a C 1 -C 40 monovalent hydrocarbon group which may contain a heteroatom, b is an integer of 0 to 5, c is an integer of 0 to 4, in case of b ≥2, R 2A may be identical or different and two R 2A may bond together to form a ring with the atoms to which they are attached, in case of c≥2, R 3A may be identical or different and two R 3A may bond together to form a ring with the atoms to which they are attached.
- Claim: 4. The molecular resist composition of claim 3 wherein the betaine type onium compound has the formula (A-2): [chemical expression included] wherein a, b, c, Q 1 to Q 3 , L 1 , L 2 , X L1 , R 1 , R 2A , and R 3A are as defined above.
- Claim: 5. The molecular resist composition of claim 1 , further comprising (C) a surfactant.
- Claim: 6. The molecular resist composition of claim 1 , further comprising (D) a quencher.
- Claim: 7. A pattern forming process comprising the steps of applying the molecular resist composition of claim 1 onto a substrate to form a resist film thereon, exposing the resist film to high-energy radiation, and developing the exposed resist film in a developer.
- Claim: 8. The process of claim 7 wherein the high-energy radiation is i-line, KrF excimer laser, ArF excimer laser, EB, or EUV of wavelength 3 to 15 nm.
- Claim: 9. The molecular resist composition of claim 2 wherein the acid labile group of acetal form is selected from the group consisting of the following formulae: [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] wherein R a is as defined above.
- Claim: 10. The molecular resist composition of claim 1 wherein R b and R c bond together to form a ring with the oxygen atoms to which they are attached and the intervening carbon atom.
- Patent References Cited: 5786131 July 1998 Allen et al. ; 8227183 July 2012 Tsubaki et al. ; 8951718 February 2015 Tsubaki et al. ; 9291904 March 2016 Tsubaki et al. ; 9348220 May 2016 Aqad et al. ; 9465298 October 2016 Tsubaki et al. ; 20150140489 May 2015 Robinson ; 20170008982 January 2017 Hasegawa ; 20180059543 March 2018 Mitsui et al. ; 20200048191 February 2020 Suga et al. ; 20200319550 October 2020 Fukushima ; 20200379345 December 2020 Fukushima et al. ; 8-15865 January 1996 ; 2007-145797 June 2007 ; 2008-281974 November 2008 ; 2008-281975 November 2008 ; 4554665 September 2010 ; 5061484 October 2012 ; 2013-8020 January 2013 ; 5317181 October 2013 ; 2014-102334 June 2014 ; 2015-060034 March 2015 ; 2015-63472 April 2015 ; 5723802 May 2015 ; 5865725 February 2016 ; 2016-147879 August 2016 ; 6130109 May 2017 ; 6155013 June 2017 ; 2018-43977 March 2018 ; 2020169157 October 2020 ; 201821402 June 2018 ; I637939 October 2018
- Other References: Lawson et al., “Single Molecule Chemically Amplified Resists Based on Ionic and Non-ionic PAGs”, Proc. of SPIE, (2008), vol. 6923, 69230K. Cited in Specification. (10 pages). cited by applicant ; Dammel et al., “193 nm Immersion Lithography—Taking the Plunge”, Journal of Photopolymer Science and Technology, 2004, vol. 17, No. 4, pp. 587-601. (18 pages). cited by applicant ; Office Action dated Feb. 19, 2021, issued in TW Application No. 109110957 (counterpart to U.S. Appl. No. 16/839,402). (9 pages). cited by applicant ; Office Action dated Jul. 7, 2021, issued in KR Application No. 10-2020-0041166 (counterpart to U.S. Appl. No. 16/839,402), with English translation. (14 pages). cited by applicant ; Non-Final Office Action dated Mar. 16, 2022, issued in U.S. Appl. No. 16/839,402. (22 pages). cited by applicant ; Office Action dated Feb. 17, 2022, issued in counterpart KR application No. 10-2020-0063173, with English Translation. (10 pages). cited by applicant
- Assistant Examiner: Champion, Richard David
- Primary Examiner: Huff, Mark F.
- Attorney, Agent or Firm: WHDA, LLP
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