Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
The response of the applicant has been read and given careful consideration. Rejections of the previous action not repeated below are withdrawn based upon the amendments to the claims and the arguments of the applicant. Responses to the arguments of the applicant are presented after the first rejection they are directed to.
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 2 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
In claim 2, 2a can be a halogen, but in claim 1, the arylene cannot be halogen substituted (see most recent amendment)
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1-3,5-9 and 10-16 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20180267402
Hatakeyama et al. 20180267402 (cited by applicant) exemplifies sulfonium salts and iodonium salts on pages 62-64.
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Polymer 3 is exemplified on page 65.
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Examples 2-1 to 2-6 combine polymer 3 with sulfonium salts 6 to 11 (respectively) and solvents. Examples 2-7 to 2-10 combine polymer 3 with iodonium salts 1-4 and solvents. Examples 2-11 to 2-13, combine polymers 3, a photoacid generator, iodonium salt 4 and solvents.
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The resist composition in Table 2 was spin coated on a silicon substrate having a 13-nm coating of spin-on-hard-mask material SHB-A940 (Shin-Etsu Chemical Co., Ltd.) having a silicon content of 43 wt % and prebaked on a hotplate at 105° C. for 60 seconds to form a resist film of 60 nm thick. Using an EUV scanner NXE3300 (ASML, NA 0.33, σ0.9/0.6, quadrupole illumination), the resist film was exposed to EUV through a mask having a hole pattern with a pitch of 46 nm and a size of 27.6 nm+20% bias (on-wafer size). The resist film was baked (PEB) on a hotplate at the temperature shown in Table 2 for 60 seconds and developed in a 2.38 wt % TMAH aqueous solution for 30 seconds to form a hole pattern having a size of 23 nm [0157]. the positive resist composition is first applied onto a substrate on which an integrated circuit is to be formed (e.g., Si, SiO.sub.2, SiN, SiON, TiN, WSi, BPSG, SOG, or organic antireflective coating) or a substrate on which a mask pattern of a circuit is to be formed (e.g., Cr, CrO, CrON, MoSi.sub.2, or SiO.sub.2) [0136]. The resist film is then exposed to a desired pattern of high-energy radiation such as UV, deep-UV, EB, EUV, x-ray, soft x-ray, excimer laser light, γ-ray or synchrotron radiation, directly or through a mask having the desired pattern [0137]. The PAGs are bounded by formulae A-1 and A-2
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Herein R.sup.1 is a hydroxyl group, carboxyl group, C.sub.1-C.sub.6 straight, branched or cyclic alkyl or alkoxy group, C.sub.2-C.sub.6 straight, branched or cyclic acyloxy group, fluorine, chlorine, bromine, amino, —NR.sup.8—C(═O)—R.sup.9, or —NR.sup.8—C(═O)—O—R.sup.9, R.sup.8 is hydrogen or a C.sub.1-C.sub.6 straight, branched or cyclic alkyl group, R.sup.9 is a C.sub.1-C.sub.6 straight, branched or cyclic alkyl group or C.sub.2-C.sub.8 straight, branched or cyclic alkenyl group. R.sup.2 is a C.sub.2-C.sub.12 straight, branched or cyclic alkylene group or C.sub.6-C.sub.10 arylene group, at least one hydrogen in the alkylene group being optionally substituted by a halogen other than fluorine, at least one hydrogen in the arylene group being optionally substituted by a C.sub.1-C.sub.10 straight, branched or cyclic alkyl or alkoxy moiety, halogen other than fluorine, or hydroxyl moiety. R.sup.3, R.sup.4 and R.sup.5 are each independently fluorine, chlorine, bromine, iodine, C.sub.1-C.sub.12 straight, branched or cyclic alkyl group, C.sub.2-C.sub.12 straight, branched or cyclic alkenyl group, C.sub.6-C.sub.20 aryl group, or C.sub.7-C.sub.12 aralkyl or aryloxoalkyl group, at least one hydrogen in the foregoing groups being optionally substituted by a hydroxyl, carboxyl, halogen, oxo, cyano, amide, nitro, sultone, sulfone or sulfonium salt-containing moiety, or at least one carbon in the foregoing groups being optionally substituted by an ether, ester, carbonyl, carbonate or sulfonate moiety, or R.sup.3 and R.sup.4 may bond together to form a ring with the sulfur atom to which they are attached. R.sup.6 and R.sup.7 are each independently trifluoromethyl, a C.sub.6-C.sub.10 aryl group, C.sub.2-C.sub.6 straight, branched or cyclic alkenyl group, or C.sub.2-C.sub.6 straight, branched or cyclic alkynyl group, at least one hydrogen in the foregoing groups being optionally substituted by a halogen, trifluoromethyl, C.sub.1-C.sub.10 straight, branched or cyclic alkyl or alkoxy, hydroxyl, carboxyl, C.sub.2-C.sub.10 straight, branched or cyclic alkoxycarbonyl, nitro or cyano moiety. X.sup.1 is a single bond, or a (p+1)-valent C.sub.1-C.sub.20 linking group which may contain an ether, carbonyl, ester, amide, sultone, lactam, carbonate, halogen, hydroxyl or carboxyl moiety. X.sup.2 is an ether group or —NR.sup.10—, R.sup.10 is hydrogen or C.sub.1-C.sub.4 straight or branched alkyl group, m is an integer of 1 to 5, n is an integer of 0 to 3, and p is an integer of 1 to 3 [0019]. Useful PAG cations are disclosed on pages 5-21. Exemplified anions bounded by A-12 and A-2 are disclosed on pages 21-29. The base polymer is described at [0061-0089]. Other useful PAGs are discussed at [0090-0114]. The addition of quenchers is disclosed [0115-0119]. The addition of surfactants is disclosed [0126]. Water repelling polymers such as those disclosed in JP 2007-297590 and JP 2008111103 [0132-0133]. Useful acid labile groups bounded by formula a1 and a2
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and
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are taught at [0062-0068]. Repeating units with hydroxy containing moieties
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are taught at [0069]. Repeating unit with adhesive moieties for the polymer
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are taught at [0069--0071]. Repeating units with fused rings such as
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are disclosed at [0072].
The addition of quenchers is disclosed. These include onium salts which are not fluorinated at the carbon alpha to the sulfonic acid moiety, onium salts of carboxylic acids, imides, methides [0117-0118].
The hydroxyphenyl acrylate repeating unit is bounded by formula B1, where A1 is a single bond, Ra is methyl, a3 is 0, a4 is 1 and a2 is 0.
Sulfonium salt 6 meets the limitations of formula A1, where q is 3, L2 is an ester, X1 is bond, L1 is a bond, m is 0, R2 is propylene (a c3 alkylene) and R3 is phenyl and R4 and R5 are C6 hydrocarbyl/phenyl groups which are linked
Sulfonium salt 9 meets the limitations of formula A1, where q is 3, L2 is an ester, X1 is bond, L1 is a bond, m is 0, R2 is iodobutylene (a c4 alkylene substituted with a halogen) and R3 is phenyl and R4 and R5 are C6 hydrocarbyl/phenyl groups which are linked
Sulfonium salt 10 meets the limitations of formula A1, where q is 3, L2 is an ester, X1 is bond, L1 is a bond, m is 0, R2 is phenylene (a c6 arylene/hydrocarbylene) and R3 is phenyl and R4 and R5 are C6 hydrocarbyl/phenyl groups which are linked
Sulfonium salt 10 meets the limitations of formula A1, where q is 3, L2 is an ester, X1 is bond, L1 is a bond, m is 0, R2 is methyl isopropyl phenylene (a c6 arylene/hydrocarbylene with alkyl substituents) and R3 is phenyl and R4 and R5 are C6 hydrocarbyl/phenyl groups which are linked
Iodonium salt 1 meets the limitations of formula A2, where q is 3, L2 is an ester, X1 is bond, L1 is a bond, m is 0, R2 is propylene (a c3 alkylene) and R6 and R7 are phenyl.
Iodonium salt 2 meets the limitations of formula A2, where q is 3, L2 is an ester, X1 is bond, L1 is a bond, m is 0, R2 is propylene (a c3 alkylene) and R6 and R7 are t-butylphenyl.
Iodonium salt 3 meets the limitations of formula A2, where q is 3, L2 is an ester, X1 is bond, L1 is a bond, m is 0, R2 is propylene (a c3 alkylene) and R6 is phenyl and R7 is fluorophenyl.
Iodonium salt 4 meets the limitations of formula A2, where q is 3, L2 is an ester, X1 is bond, L1 is a bond, m is 0, R2 is phenylene (a c6 arylene/hydrocarbylene) and R6 is phenyl and R7 is triimethylphenyl.
Hatakeyama et al. 20180267402 does not exemplify the full range of PAGs embraced by the teachings of A-1 or A-2 polymers with the acid labile repeating units bounded by B2-1 (claim 3), polymers with repeating units bounded by B2-2 (claims 4), polymers with repeating units bounded by formulae B3, B4 or B5 (claim 5) polymers with the full range of bound/pendant PAGs (claims 6), the use of electron beam exposure, or the use of the resist applied to a photomask substrate.
With respect to claims 1-3,5,6,8-9 and 11-13, it would have been obvious to modify composition of the cited examples by replacing the acid labile methylcyclohexylacrylate used in the polymer with a phenolic acid labile repeating unit bounded by formula a2 and one of AL-1 to AL-3 at [0048--0055] and to replace the lactone containing acrylate with
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based upon the equivalence at [0062-0068] with a reasonable expectation of forming a useful resist and when patterned as in the examples a useful resist pattern. This would result in a resist polymer where the aromatic containing repeating units make up more than 60 mol% of the resist. polymer composition (claims 3,5,7) .
With respect to claims 1-3,5,6,8,9 and 10-13, in addition to the basis above it would have been obvious to modify the composition of the cited examples by replacing at least a portion of the anion of sulfonium salts 6-11 or iodonium salts 1-4 with other iodized anions, such as any of those exemplified at pages 21-29, including those the sulfonic acid moiety attached directly to a phenyl ring, with a reasonable expectation of forming a useful resist and when patterned as in the examples a useful resist pattern.
With respect to claims 1-3,56,8,9 and 10-13, in addition to the basis above it would have been obvious to modify composition of the cited examples by replacing at least a portion of the bound PAG with other disclosed PAG moieties, such as those disclosed at [0074-0082] with a reasonable expectation of forming a useful resist and when patterned as in the examples a useful resist pattern.
With respect to claims 1-3,5,6,8,9 and 10-13, in addition to the basis above it would have been obvious to modify the composition of the cited examples by exposing the resist using electron beam exposure in place of the EUV used based upon the disclosed equivalence at [0137] with a reasonable expectation of forming a useful resist pattern
With respect to claims 1-3,5,6,8,9 and 11-13, in addition to the basis above it would have been obvious to modify composition of the cited examples by replacing at least a portion of the acid labile group used in the polymer with a phenolic acid labile repeating unit bounded by formula a2 and one of AL-1 to AL-3 at [0062--0068] with a reasonable expectation of forming a useful resist and when patterned as in the examples a useful resist pattern.
With respect to claims 1-3,5,6,8,9 and 11-13, in addition to the basis above it would have been obvious to modify composition of the cited examples by replacing at least a portion of the hydroxy substituted to a repeating unit such as
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disclosed at [0069-0071] with a reasonable expectation of forming a useful resist and when patterned as in the examples a useful resist pattern.
With respect to claims 1-3,5,6,8,9 and 11-13, in addition to the basis above it would have been obvious to modify composition of the cited examples by replacing adding a repeating unit selected from
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disclosed at [0074] with a reasonable expectation of forming a useful resist and when patterned as in the examples a useful resist pattern.
With respect to claims 1-3,5,6 and 8-16, in addition to the basis above it would have been obvious to modify the composition of the cited examples by coating the resist on a substrate on which a mask circuit pattern is to be formed such as Cr, CrO, CrON, MoSi.sub.2, or SiO.sub.2, rather than the wafer to facilitate the formation of a patterned photomask as disclosed at [0136] with a reasonable expectation of forming a useful resist pattern. The mask formed can be transmissive or reflective (Cr, being a metal is reflective).
In the response of 3/17/2026, the applicant argues that Hatakeyama et al. 20180267402 does not use onium salts in any of the examples. This is incorrect. The examiner does agrees that they are not used in examples in combination with a polymer having at least 60 mol% of the aromatic containing monomers. The applicant argues that resist. patterns with good regularity and fidelity is achieved by this combination. The examiner points out that there is no comparative data using a polymer with less than 60 mol% content in the record. The comparative examples use polymer A-1 which is also used in the inventive examples such as 1-1. So there does not seem to be a basis for the unexpected results relative to the closest prior art. Also the claims are considerably broader than any alleged showing as the claims doe not recite any amounts for the polymer, photoacid generator, quenchers or fluorinated polymer in the resists similar to those used in the inventive examples. There will be some criticality in the amounts of these. The rejection as modified stands. The numbering in the header included a typographical error, which has been corrected. The statements of obviousness in the previous action under this heading included claims 14-16 (in bold) which were not included in the heading.
Claims 1-3,5,6, and 8-16 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20180267402, in view of Harada et al. JP 2008111103 and/or Kaneko et al. JP 2007297590.
Harada et al. JP 2008111103 (machine translation attached) teaches fluorinated polymers to increase water repellency. Repeating units disclosed include those on pages 30 or 69.
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Kaneko et al. JP 2007297590 (machine translation attached) teaches fluorinated polymers to be added to resists. These include the monomers/repeating units disclosed on pages 11,12,14-
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Hatakeyama et al. 20180267402 does not exemplify a range of different fluorinated polymers.
In addition to the basis above, the examiner holds that it would have been obvious to one skilled in the art to modify resist compositions which are either exemplified or rendered obvious by Hatakeyama et al. 20180267402 by adding a fluorinated monomer such as those taught by Harada et al. JP 2008111103 and/or Kaneko et al. JP 2007297590 based upon the direction to the fluorinated polymers taught in these references at [0132-0133].
The examiner relied upon the response above as no further arguments were advanced by the applicant.
Claims 1-16 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20180267402, in view of Harada et al. JP 2008111103 and/or Kaneko et al. JP 2007297590, further in view of Hasegawa et al. 20130084527.
Hasegawa et al. 20130084527 teaches resist polymers which include repeating units bounded by
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where R.sup.1 and R.sup.2 each are a straight, branched or cyclic C.sub.1-C.sub.8 alkyl, C.sub.6-C.sub.10 aryl, or C.sub.2-C.sub.10 alkenyl group, which may contain an oxygen or sulfur atom, R.sup.3 is fluorine or trifluoromethyl, and m is an integer of 1 to 5 [0033-0035]. Specific monomers leading to this repeating unit are disclosed on pages 6-8. It is generally believed that fluorine atoms have high absorption relative to EUV of 13.5 nm wavelength and thus exert a sensitizing or sensitivity enhancing effect. It is thus expected that sensitivity is improved by introducing fluorine into the protective group. However, if fluorine is introduced into the acid labile group in the form of tertiary alkyl group, the stability of an intermediate cation of deprotection reaction is substantially reduced by the electron attracting effect of fluorine, and as a consequence, neither olefin formation nor deprotection reaction occurs. However, a tertiary acid labile group having a fluorinated aromatic group exhibits appropriate reactivity for deprotection because the intermediate cation has optimum stability [0031].
The combination of Hatakeyama et al. 20180267402 combined with Harada et al. JP 2008111103 and/or Kaneko et al. JP 2007297590 does not teach a repeating unit bounded by B2-2 of instant claim 4.
It would have been obvious to one skilled int the art to modify resists rendered obvious by the combination of Hatakeyama et al. 20180267402 with Harada et al. JP 2008111103 and/or Kaneko et al. JP 2007297590 by adding other acid labile repeating units known to be useful in resists, such as those bounded by formula 2 and/or exemplified on pages 6-8 of Hasegawa et al. 20130084527 with a reasonable expectation of forming a useful resist and after exposure and development a useful resist pattern.
The examiner relied upon the response above as no further arguments were advanced by the applicant.
Claims 1-3 and 5-17 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20180267402, in view of Fujiwara et al. 20210149301 and/or Masunaga et al. 20160299428.
Fujiwara et al. 20210149301 teaches the use of acid diffusion inhibitors to prevent the diffusion of the acid generated by the photoacid generator through the resist. Suitable salts for preventing acid diffusion include onium salts of α-no-fluorinated sulfonic acids and carboxylic acids include onium salt compounds having the formulae (8A) and (8B).
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In formula (8A), R.sup.q1 is hydrogen, methoxy, or a C.sub.1-C.sub.40 hydrocarbyl group which may contain a heteroatom, exclusive of the group wherein hydrogen bonded to the carbon atom at α-position relative to the sulfo group is substituted by fluorine or fluoroalkyl. In formula (8B), R.sup.q2 is hydrogen, hydroxyl or a C.sub.1-C.sub.40 hydrocarbyl group which may contain a heteroatom. In formulae (8A) and (8B), Mq.sup.+ is an onium cation, which is preferably selected to from cations having the formulae (9A), (9B) and (9C) [0161-0176]. The use of betaines of weak onium salts to prevent acid diffusion is disclosed. Examples include
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[0178-0179].
Masunaga et al. 20160299428 teaches onium salts having the structure
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Herein R.sup.01, R.sup.02, R.sup.03 and R.sup.04 are each independently hydrogen, -L-CO.sub.2.sup.−, or a straight C.sub.1-C.sub.20, branched or cyclic C.sub.3-C.sub.20 monovalent hydrocarbon group which may be substituted with or separated by a heteroatom, or a pair of R.sup.01 and R.sup.02, R.sup.02 and R.sup.03, or R.sup.03 and R.sup.04 may bond together to form a ring with the carbon atoms to which they are attached. L is a single bond or a straight C.sub.1-C.sub.20, branched or cyclic C.sub.3-C.sub.20 divalent hydrocarbon group which may be substituted with or separated by a heteroatom. R.sup.05 is hydrogen or a straight C.sub.1-C.sub.20, branched or cyclic C.sub.3-C.sub.20 monovalent hydrocarbon group which may be substituted with or separated by a heteroatom. Z.sup.+ is a sulfonium cation or an iodonium cation [0060-0066]. These are used to control the diffusion of the acid [0182-0183] and examples.
In addition to the basis above, it would have been obvious to one skilled in the art to modify the compositions and processes using them rendered obvious by the teachings of Hatakeyama et al. 20180267402 by adding known quenchers/weak acids such as those disclosed by Fujiwara et al. 20210149301 and/or Masunaga et al. 20160299428 to control the diffusion of the photogenerated acid based upon the direction in Hatakeyama et al. 20180267402 at [0117-0118].
Claims 1-6 and 8-17 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20180267402, in view of Harada et al. JP 2008111103 and/or Kaneko et al. JP 2007297590, in combination with Hasegawa et al. 20130084527 and further in view of Fujiwara et al. 20210149301 and/or Masunaga et al. 20160299428.
In addition to the basis above, it would have been obvious to one skilled in the art to modify the compositions and processes using them rendered obvious by the teachings of Hatakeyama et al. 20180267402, Hasegawa et al. 20130084527 combined with Harada et al. JP 2008111103 and/or Kaneko et al. JP 2007297590 by adding known quenchers/weak acids such as those disclosed by Fujiwara et al. 20210149301 and/or Masunaga et al. 20160299428 to control the diffusion of the photogenerated acid based upon the direction in Hatakeyama et al. 20180267402 at [0117-0118].
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Martin J Angebranndt whose telephone number is (571)272-1378. The examiner can normally be reached 7-3:30 pm EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark F Huff can be reached at 571-272-1385. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 April 21, 2026
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