DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-22 are pending.
The foreign priority application No.2022-0545623 filed on March 29, 2022 in Japan has been received and it is acknowledged.
Claim Rejections - 35 USC § 103
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 1-17 and 19-22 are rejected under 35 U.S.C. 103 as being unpatentable over Komuro et al. (US 2021/0341836) in view of Ichikawa et al. (US Patent 8,614,046) and in further view of Masubuchi et al. (US 2011/0177453).
With regard to claims 1 and 5, Komuro et al. teach the salt of formula (I):
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wherein R1, R2, and R3 may be a hydroxy group, -O-R10, -O-CO-O-R10, or -O-L1-CO-O-R10, L1 is an alkanediyl group having 1 to 6 carbon atoms, R10 is an acid labile group, R4-R9 each may independently be a halogen atom or an alkyl fluoride having 1 to 6 carbon atoms, X1, X2, and X3 are oxygen or sulfur, m1 is 1 to 5, m2, m3, m8, m9 are integers from 0 to 5, m4, m5, m6, and m7 are integers from 0 to 4, m1+m7 is between 1 and 7, m2+m8 is between 0 and 5, m3+m9 is between 0 and 5, and AI- is an organic anion (abstract, par.0005-0022).
Komuro et al. teach that the anion AI- may be a carboxylic acid anion (section (8) in par.0025), but fail to teach the carboxylate salt in claim 1.
Ichikawa et al. teach the salt of formula (I-Pa):
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, wherein ZPa+ represents an organic cation such as a sulfonium cation (abstract, column 5, lines 35 and 45-50).
Additionally, it is well-known in the art that incorporating an acid generator salt in a polymer chain increases the sensitivity and line edge roughness (LER)(abstract and par.0009 of Masubuchi et al.).
Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to use the carboxylic acid anion of formula:
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as the organic anion AI- in the salt of formula (I) of Komuro et al., in order to be able to incorporate the salt in a resist resin and improve the sensitivity and line edge roughness (LER) of the resist.
Ichikawa et al. further teach that the anion of formula:
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may be represented by formulas:
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(column 3, lines 30-40) or
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(column 5, lines 1-10)
A salt formula:
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wherein the anion AI- is
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is a carboxylate of formula (I) in claims 1 and 5, wherein R1, R2, and R3 may be a hydroxy group, -O-R10, -O-CO-O-R10, or -O-L1-CO-O-R10, L1 is an alkanediyl group having 1 to 6 carbon atoms, R10 is an acid labile group, R4-R9 each independently may be a halogen atom or an alkyl fluoride having 1 to 6 carbon atoms, X1, X2, and X3 are oxygen or sulfur, m1 is 1 to 5, m2, m3, m8, m9 are integers from 0 to 5, m4, m5, m6, and m7 are integers from 0 to 4, m1+m7 is between 1 and 7, m2+m8 is between 0 and 5, m3+m9 is between 0 and 5, Rbb1 is a hydrogen atom, a X10 is a single bond, L10 is a single bond, and X0 is an unsubstituted aromatic hydrocarbon with 6 carbon atoms.
The range of 0 to 4 for m4 includes the claimed range of 1 to 4 for m4.
A salt formula:
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wherein the anion AI- is
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is a carboxylate of formula (I) in claims 1 and 5, whereinR1, R2, and R3 may be a hydroxy group, -O-R10, -O-CO-O-R10, or -O-L1-CO-O-R10, L1 is an alkanediyl group having 1 to 6 carbon atoms, R10 is an acid labile group, R4-R9 each independently may be a halogen atom or an alkyl fluoride having 1 to 6 carbon atoms, A1, A2, and A3 are oxygen or sulfur, m1 is 1 to 5, m2, m3, m8, m9 are integers from 0 to 5, m4, m5, m6, and m7 are integers from 0 to 4, m1+m7 is between 1 and 7, m2+m8 is between 0 and 5, m3+m9 is between 0 and 5, Rbb1 is a methyl group, X0 is a hydrocarbon group with 10 carbon atoms, L10 is a single bond, and X10 is *-CO-O-**, * represents the bonding site to the carbon atom to which Rbb1 is bonded.
The range of 0 to 4 for m4 includes the claimed range of 1 to 4 for m4.
With regard to claims 2-4, Komuro et al. teach that X1, X2, and X3 are oxygen atoms (section (2) in par.0022).
A salt formula:
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wherein X1, X2, and X3 are oxygen atoms and the anion AI- is
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is a carboxylate of formula (I), wherein A1 is ***-X01-L01-, A2 is ***-X02-L02, and A3 is ***-X03-L03, wherein X01, X02, and X03 are oxygen atoms, L01, L02, and L03 are single bonds.
With regard to claim 6, Komuro et al. teach that the acid labile group R10 may be represented by the group (1a) or the group (2a):
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, wherein in formula (1a) Raa1, Raa2, and Raa3 each independently represent an alkyl group with 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 8 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, or an aromatic group having 6 to 18 carbon atoms which may have a substituent, or Raa2 and Raa3 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with carbon atoms to which Raa2 and Raa3 are bonded, and in formula (2a) Raa1’ and Raa2’ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, Raa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or Raa2’ and Raa3’ are bonded to each other to form a heterocyclic group having 3 to 20 carbon atoms together with C-Xa- to which Raa2’ and Raa3’ are bonded, and -CH2- included in the hydrocarbon group and the heterocyclic group may be replaced by -O- or -S-, Xa represents an oxygen atom or sulfur atom, *represents a bonding site (par.0022-0023).
With regard to claims 7-12, a salt formula:
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wherein the anion AI- is
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is a carboxylate of formula (I), wherein X10 is a single bond, L10 is a single bond, X0 is an unsubstituted phenylene group.
An unsubstituted phenylene group is an unsubstituted aromatic hydrocarbon with 6 carbon atoms in claims 7 and 8.
A salt formula:
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wherein the anion AI- is
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is a carboxylate of formula (I), wherein X0 is an adamantanediyl group, L10 is a single bond, and X10 is *-CO-O-**, * represents the bonding site to the carbon atom to which Rbb1 is bonded.
An adamantanediyl group is an aliphatic hydrocarbon group with 10 carbon atoms in claim 7, and an alicyclic hydrocarbon with 10 carbon atoms in claim 8.
With regard to claims 13-17, Komuro et al. teach an acid generator comprising the salt, and a resist composition comprising the acid generator and a resin having an acid-labile group (sections (10) and (11) in par.0028).
Masubuchi et al. teach incorporating an acid generator salt in a polymer chain (abstract and par.0009 of Masubuchi et al.).
Ichikawa et al. also teach a polymer comprising a structural unit derived from the salt having the carboxylate anion with unsaturated double bond (column 41, lines 61-63), and resist compositions comprising resins having structural units derived from the from the salt having the carboxylate anion with unsaturated double bond and structural units with acid-labile groups (Examples 20, 21, 23, 24, 27, and 28 in Table 1, column 114, and the formulas of the resins B in columns 105-113, column 49, lines 39-43).
With regard to claim 19, Komuro et al. teach that the resin having an acid-labile group is at least one selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2):
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and
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, wherein La1 and La2 each represent -O- or *-O-(CH2)k1-CO-O-, k1 represents an integer of 1 to 7, * represents a bond to -CO-, Ra4 and Ra5 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, Ra6 and Ra7 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkenyl having 2 to 8 carbon atoms, an alicyclic hydrocarbon having 3 to 18 carbon atoms, an aromatic hydrocarbon having 6 to 18 carbon atoms, or a group obtained by combining these groups, m1 =0-14, n1=0-10, and m1’=0-3 (par.0028-0034).
The structural units represented by formulas (a1-1) and (a1-2) of Komuro et al. are equivalent to the structural units of formulas (a1-1) and (a1-2) in claim 19.
With regard to claim 20, Komuro et al. teach that the resin having an acid-labile group includes a structural unit of formula (a2-A):
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, wherein Ra50 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, Ra51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkoxycarbonyl having 2 to 4 carbon atoms, alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group, Aa50 represents a single bond or *-Xa51-(Aa52-Xa52)-, *represents a bond to carbon atoms to which Ra50 is bonded, Aa52 represents an alkanediyl group having 1 to 6 carbon atoms, Xa51 and Xa52 each independently represent -O-, -CO-O-, or -O-CO-, nb represents 0 or 1, mb represents an integer from 0 to 4 (par.0034-0041).
With regard to claim 21, Komuro et al. teach that the resist composition may also comprise an acid generator (B) of formula (B1):
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, wherein Qb1 and Qb2 each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, Lb1 represent a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, -CH2- included in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, Y represent a methyl group which may have a substituent or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, -CH2- included in the alicyclic hydrocarbon group may be replaced by -O-, -S(O)2-, or -CO-. and Z1+ represents an organic cation (par.0271-0276).
With regard to claim 22, Komuro et al. teach a method for producing a pattern, the method comprising the steps of:
-applying the resist composition on a substrate;
-drying the applied resist composition to form a composition layer;
-exposing the composition layer;
-heating the exposed composition layer; and
-developing the heated composition layer (par.0041-0046).
Allowable Subject Matter
Claim 18 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Komuro et al. (US 2021/0341836) fail to teach the resist composition in claim 18.
There are no prior art teachings that would motivate one of ordinary skill in the art to modify Kumoro et al. and obtain the resist composition in claim 18.
Response to Amendment
The Declaration under 37 CFR 1.132 filed on June 10, 2026 is insufficient to overcome the rejection of claims 1-17 and 19-22 based upon Komuro et al. (US 2021/0341836) in view of Ichikawa et al. (US Patent 8,614,046) and in further view of Masubuchi et al. (US 2011/0177453) as set forth in the last Office action because the evidence submitted in the Declaration is not commensurate in scope with the claimed invention.
The Reference Examples 3 and 4 in the Declaration show unexpected superior results for photoresist compositions comprising the resin A4-A2, wherein the resin A4-A2 is represented by the formula:
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(pages 6 and 7 of the Declaration).
The last repeating unit of the resin A4-A2 is derived from a carboxylate of formula (I) in claim 1, wherein m2=0, m3=0, m5=0, m6=0, m7=0, m8=0, m9=0, m1=1, m4=2, A1 is a hydrocarbon group with 2 carbon atoms wherein a -CH2- group is substituted with -O-, R4 is I, R1 is -OR10, R10 is an acid labile group of formula -CH2-O-CH2-CH3, Rbb1 is an alkyl group with 1 carbon atom, X10 is *-CO-O-**, L10 is a hydrocarbon with 6 carbon atoms and containing an iodine atom as substituent, and X0 is a single bond.
However, claim 1 allows for a carboxylate of formula (I):
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Examples of alkanediyl groups L1 are provided in par.0010 of the specification, and examples of acid labile groups R10 are provided in par.0011-0018 of the specification.
Par.0019-0023 of the specification provides examples of groups R4-R9.
Par.0024-0028 of the specification provides examples of groups A1-A3.
Examples of 142 cations of the compound of formula (I) are shown in par.0030-0038 of the specification.
Par.0039-0043 of the specification show examples of groups X0 in the anion of the compound of formula (I).
Par.0044 of the specification shows examples of groups Rbb1 and X10.
Par.0045-0049 of the specification show examples of groups L10.
Par.0050 shows 27 examples of the anions of the compound of formula (I).
Therefore, the compound of formula (I) in claim 1 may be represented by a large number of combinations of anions and cations. The resin A4-A2 in the Declaration under 37 CFR 1.132 filed on June 10, 2026 is not sufficient to show unexpected superior results of the claimed compound.
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980) (Claims were directed to a process for removing corrosion at "elevated temperatures" using a certain ion exchange resin (with the exception of claim 8 which recited a temperature in excess of 100°C). Appellant demonstrated unexpected results via comparative tests with the prior art ion exchange resin at 110°C and 130°C. The court affirmed the rejection of claims 1-7 and 9-10 because the term "elevated temperatures" encompassed temperatures as low as 60°C where the prior art ion exchange resin was known to perform well. The rejection of claim 8, directed to a temperature in excess of 100°C, was reversed.). See also In re Peterson, 315 F.3d 1325, 1329-31, 65 USPQ2d 1379, 1382-85 (Fed. Cir. 2003) (data showing improved alloy strength with the addition of 2% rhenium did not evidence unexpected results for the entire claimed range of about 1-3% rhenium); In re Grasselli, 713 F.2d 731, 741, 218 USPQ 769, 777 (Fed. Cir. 1983) (Claims were directed to certain catalysts containing an alkali metal. Evidence presented to rebut an obviousness rejection compared catalysts containing sodium with the prior art. The court held this evidence insufficient to rebut the prima facie case because experiments limited to sodium were not commensurate in scope with the claims.). (MPEP 716.02(d) Unexpected Results Commensurate in Scope With Claimed Invention)
Response to Arguments
Applicant's arguments filed on June 10, 2026 have been fully considered but they are not persuasive.
On page 5 of the Remarks the applicant argues that the carboxylate salts combining the specified cations and anions of the instant application provide excellent CD uniformity (CDU), as demonstrated by the Examples provided in the specification and in the Declaration under 37 CFR 1.132.
On pages 5-6 of the Remarks the applicant shows that a resist composition comprises the compound I-1270 shows improved CDU when compared to resists comprising the compounds IX-2 and IX-3, wherein the compound I-1270 is represented by the formula:
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.
The compounds of formulas IX-2 and IX-3 are not compounds of formula (I) in claim 1, and the compound of formula I-1270 is a compound of formula (I) in claim 1, wherein m2=0, m3=0, m5=0, m6=0, m7=0, m8=0, m9=0, m1=1, m4=2, A1 is a hydrocarbon group with 1 carbon atom wherein -CH2- group is substituted with -O-, R4 is I, R1 is -OR10, R10 is an acid labile group of formula -CH(CH3)-O-CH2-CH3, Rbb1 is an alkyl group with 1 carbon atom, X10 is *-CO-O-**, L10 is a hydrocarbon with 10 carbon atoms, and X0 is a single bond.
On pages 7-8 of the Remarks the applicant shows that the resist composition comprising resin A1 has improved CDU when compared to a resist composition comprising the resin A1-X1.
The resin A1-X1 comprises a repeating unit that is not derived from a compound within the scope of claim 1.
The resin A1 comprises a repeating unit derived from the salt I-1270 of formula
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, which is a compound of formula (I) in claim 1, wherein m2=0, m3=0, m5=0, m6=0, m7=0, m8=0, m9=0, m1=1, m4=2, A1 is a hydrocarbon group with 1 carbon atom wherein -CH2- group is substituted with -O-, R4 is I, R1 is -OR10, R10 is an acid labile group of formula -CH(CH3)-O-CH2-CH3, Rbb1 is an alkyl group with 1 carbon atom, X10 is *-CO-O-**, L10 is a hydrocarbon with 10 carbon atoms, and X0 is a single bond.
On pages 8-10 of the Remarks the applicant shows that resist compositions comprising the resins A4 and A4-A2 show excellent CDU.
The resin A4 comprises a repeating unit derived from the monomer I-2944 of formula:
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, which is a compound of formula (I) in claim 1, wherein m2=0, m3=0, m5=0, m6=0, m7=0, m8=0, m9=0, m1=1, m4=2, A1 is a hydrocarbon group with 2 carbon atoms wherein a -CH2- group is substituted with -O-, R4 is I, R1 is -OR10, R10 is an acid labile group of formula -CH2-O-CH2-CH3, Rbb1 is an alkyl group with 1 carbon atom, X10 is *-CO-O-**, L10 is a hydrocarbon with 10 carbon atoms, and X0 is a single bond.
The resin A4-A2 comprises a repeating unit derived from the monomer I-A2 of formula:
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, which is a compound of formula (I) in claim 1, wherein m2=0, m3=0, m5=0, m6=0, m7=0, m8=0, m9=0, m1=1, m4=2, A1 is a hydrocarbon group with 2 carbon atoms wherein a -CH2- group is substituted with -O-, R4 is I, R1 is -OR10, R10 is an acid labile group of formula -CH2-O-CH2-CH3, Rbb1 is an alkyl group with 1 carbon atom, X10 is *-CO-O-**, L10 is a hydrocarbon with 6 carbon atoms and iodine atoms substituents, and X0 is a single bond.
However, claim 1 allows for a carboxylate of formula (I):
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Examples of alkanediyl groups L1 are provided in par.0010 of the specification, and examples of acid labile groups R10 are provided in par.0011-0018 of the specification.
Par.0019-0023 of the specification provides examples of groups R4-R9.
Par.0024-0028 of the specification provides examples of groups A1-A3.
Examples of 142 cations of the compound of formula (I) are shown in par.0030-0038 of the specification.
Par.0039-0043 of the specification show examples of groups X0 in the anion of the compound of formula (I).
Par.0044 of the specification shows examples of groups Rbb1 and X10.
Par.0045-0049 of the specification show examples of groups L10.
Par.0050 shows 27 examples of the anions of the compound of formula (I).
Therefore, the compound of formula (I) in claim 1 may be represented by a large number of combinations of anions and cations. The examples of resist composition using the compounds of formula I-1270,I-2944, and I-A2 are not sufficient to show unexpected superior results of the claimed compound (MPEP 716.02(d) Unexpected Results Commensurate in Scope With Claimed Invention).
Conclusion
THIS ACTION IS MADE FINAL. 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.
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/ANCA EOFF/ Primary Examiner, Art Unit 1722
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