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.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on February 02, 2026 has been entered.
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 Arguments
Applicant's arguments filed on December 29, 2025 have been fully considered but they are not persuasive.
On pages 14-17 of the Remarks the applicant argues rejection of claims 1-17 and 19-22 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).
On pages 14-15, the applicant notes that Komuro et al. disclose salts of general formula (I) wherein AI- is an organic cation, and Ichikawa et al. teach anions including a polymerizable group. On page 16 the applicant argues that Komuro et al. does not teach that the anions of Ichikawa and Masubuchi may be used as anion in the salt of formula (I).
The applicant further argues that there is no motivation to apply the anions of Ichikawa et al. and Masubuchi et al. to the salt of Komuro et al.
The examiner would like to note that Komuro et al. teach that the salt of formula (I) has an organic anion AI-, wherein AI- may be a carboxylic acid anion (abstract, par.0022, section (8) in par.0025).
Ichikawa et al. teach a salt comprising a carboxylic acid anion and the organic cation Zpa+ (abstract. Par.0007). The organic cation Zpa+ may be a sulfonium cation of formula:
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wherein PB-PD may be C6-C36 aromatic hydrocarbon atoms which can have one or more substituents (par.0024).
Therefore, Komuro et al. and Ichikawa et al. both teach salts with sulfonium cations and carboxylic acid anions. This would motivate one of ordinary skill to use the anion of Ichikawa et al. as the anion AI- in combination with a sulfonium cation in the salt of formula (I) of Komuro et al.
Masubuchi et al. is relied on to show that incorporating an acid generator salt in a polymer chain increases the sensitivity and line edge roughness (abstract and par.0009 of Masubuchi et al.).
Therefore, using the carboxylic acid cation comprising a polymerizable group of Ichikawa et al. as the anion AI- in the salt of formula (I) of Komuro et al. allows for the salt (I) to be incorporated in the polymer chain and increases the sensitivity and the line edge roughness of the photoresist.
On page 16 of the Remarks the applicant argues that Komuro et al. do not specifically disclose the cation in formula (I) in claim 1, because Komuro et al. do not teach a halogen atom or a haloalkyl group as R4 in addition to a hydroxy group or a group including an acid-labile group as R1 on one benzene ring.
The examiner would like to note that 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 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, and AI- is an organic anion (abstract, par.0005-0022).
The range of 0-4 for m4 includes the range of 1-4 for m4 in claim 1.
Therefore, Komuro et al. provides motivation to have a benzene ring comprising a group R1 and between 1 and 4 groups R4, wherein R1 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, and R4 each independently represent a halogen atom, or an alkyl fluoride having 1 to 6 carbon atoms.
Therefore, the rejection of claims 1-17 and 19-22 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) is maintained.
Conclusion
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/ANCA EOFF/ Primary Examiner, Art Unit 1722