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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 15 September 2025 has been entered.
Response to Arguments
Applicant’s arguments filed 15 September 2025 have been fully considered but they are not persuasive.
Applicant has amended instant claim 1 such that claim 1 recites that the DNQ-PAC is a single material or a mixture of materials in which a 2,1,5-diazonaphthoquinonesulfonate moiety having structure (10) forms at least one sulfonate ester with a phenolic compound, wherein said material is present from about 0.2 wt% total solids to 2.0 wt% of total solids, and further specifies the photoacid generator content. Claim 2 has also been amended to recite types of compounds that the photoacid generator may be. Applicant argues that the previous rejection of claim 1, made over Liu in view of Ota, should be withdrawn because a person having ordinary skill in the art (PHOSITA) would have no motivation to use a DNQ sulfonate PAC of structure (10) with the applicant’s component d) acrylic resin, which is aqueous base insoluble, absent impermissible hindsight of the Applicant’s composition to correct the deficiencies of Liu with Ota. The Applicant further argues that Liu and Ota are nonanalogous art. The Applicant additionally alleges unexpected results obtained by the claimed invention. These arguments will be addressed separately below. The Examiner acknowledges and has reviewed the Applicant’s submission of a Declaration under 37 CFR 1.132, filed on 15 September 2025.
In regards to the Applicant’s first argument that a PHOSITA would have no motivation to combine the teachings of Liu and Ota, Applicant argues that there would be no motivation for a PHOSITA to use a DNQ sulfonate PAC of structure (10) with the applicant’s component d) acrylic resin, which is aqueous base insoluble, absent impermissible hindsight of the Applicant’s composition to correct the deficiencies of Liu with Ota. In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). Liu outlines that the photosensitive composition may include diazonaphthoquinone (DNQ) sulfonate ester compounds (Liu, paragraph 0017). Liu does not specify examples of such compounds. Ota teaches that a 2,1,5-DNQ or 2,1,4-DNQ can be used in conjunction with the photosensitive composition (Ota, Col. 5 Line 27-39). The Applicant presumes (see page 14 of Applicant’s arguments filed 15 September 2025) that Liu includes this class of compounds because the 2,1,4-DNQ, as a sulfonate ester derivative, is known to produce a strong sulfonic acid. Applicant further argues that the 2,1,5-DNQ isomer only releases carboxylic acid, which can not affect cleavage of the Applicant’s acid labile group. Thus, Applicant argues, that the DNQ sulfonate esters, such as the claimed 2,1,5-DNQ isomer, are designed for use with base soluble novolak phenolic resins and would have no motivation to use such an isomer with the claimed acrylic resin, which is aqueous base insoluble. However, the Applicant’s arguments in this regard are not considered persuasive because Liu teaches that DNQ sulfonate ester compounds may be used in the composition, whilst providing no guidance suggesting that only particular DNQ sulfonate ester compounds may be utilized. Ota teaches that the 2,1,4-DNQ and 2,1,5-DNQ isomers are functional equivalents for producing photoresist composition. The Examiner recognizes there are differences between both prior art references and the instant application. However, given the disclosures of the prior art and the instant application, the invention recited by instant claim 1 is still considered prima facie obvious in view of Liu and Ota, at least using the rationale of 2143 I. E. (“Obvious to Try” rationale). For instance, Liu’s disclosure broadly states DNQ sulfonate ester compounds to be used, and thus a PHOSITA would find it “obvious to try” any isomer of DNQ sulfonate ester, as there is no suggestion by Liu that only certain isomers will work. Even if, arguendo, a PHOSITA interpreted Liu’s disclosure of DNQ sulfonate ester compounds to mean 2,1,4-DNQ sulfonate esters, it would have still been obvious to try 2,1,5-DNQ due to Ota teaching 2,1,4-DNQ and 2,1,5-DNQ isomers as being equivalents in photoresist compositions. Refer to MPEP 2144.06 II. Therefore, the combination of Liu and Ota does not rely upon impermissible hindsight reasoning and accordingly, Applicant’s arguments in this regard are not found to be persuasive.
In response to applicant's argument that Liu and Ota are nonanalogous art, it has been held that a prior art reference must either be in the field of the inventor’s endeavor or, if not, then be reasonably pertinent to the particular problem with which the inventor was concerned, in order to be relied upon as a basis for rejection of the claimed invention. See In re Oetiker, 977 F.2d 1443, 24 USPQ2d 1443 (Fed. Cir. 1992). In this case, Liu is in the field of the inventor’s endeavor of photoresist imaging, specifically a positive working photosensitive material which may, without limitation, be useful on chalcophilic or reflective substrates (see Liu, paragraph 0001). Refer to paragraph 0001 of the instant application’s specification, which recites the same field of invention. Ota’s invention relates to photoresist compositions, specifically positive photoresist compositions suited for photofabrication (see Ota, Col. 1 Line 5-13). Ota states that the problem with which the inventors were concerned was to solve the issue of poor adhesion of the photoresist composition to substrates (Ota, Col. 1 Line 46-Col. 2 Line 2). The instant application similarly aims to solve the problems of poor and/or overly strong adhesion of the photoresist to the substrate (see paragraph 0002-0005), which is said to cause defective patterns. Thus, the problem that the inventors of the instant application were concerned with is similarly to the problem that the inventors of Ota’s invention were concerned with. Therefore, Liu is analogous art because Liu is from the same field of endeavor and Ota is analogous art because at least Ota is pertinent to the same problem that the inventor was concerned with, if not also from the same field of endeavor. The Applicant argues that Liu’s composition and Ota’s composition operate through entirely different mechanisms (see page 16 of the remarks filed 15 September 2025). Applicant proceeds to outline the differences in Liu’s and Ota’s acrylic resins, arguing that the references teach away from each other. However, the Examiner’s rejection does not rely upon switching the acrylic resin. The rejection relies upon using a specific DNQ sulfonate ester taught by Ota (the 2,1,5-DNQ isomer) in place of the broadly defined “DNQ sulfonate ester” taught by Liu. There is no other modification to Liu’s composition, and thus the prior art references are not considered to be teaching away from the claimed invention. Therefore, Applicant’s arguments in this regard are not considered persuasive.
In regards to the Applicant’s arguments regarding unexpected results, the Examiner has reviewed the declaration under 37 CFR 1.132 filed 15 September 2025. However, the issue of the results not be commensurate in scope with the claimed invention remains. MPEP 716.02(d) requires that "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." The Applicant cites Table 1 of the instant application’s specification and the declaration provides figures comparing Formulation 3 and Formulation 17 (the comparative example). The primary issue with the allegation of unexpected results is that the data provided to support such an allegation does not provide sufficient evidence that the results hold for the entire scope of the claim. For instance, Applicant’s results only demonstrate two DNQ-PAC compounds according to component a) as recited by instant claim 1 (NK-280 and PW-898). Furthermore, only one inventive example utilizes PW-898, thus failing to demonstrate advantageous results across the claimed range for this particular DNQ-PAC. The Formulation Examples all use the same heterocyclic thiol (1H-1,2,4-triazole-3-thiol), the same photoacid generator (NIT PAG), and the same Novolak resin (Novolak-3) (see paragraphs 0121-0128 of the instant application’s specification). In other words, the Examples provided by the Applicant only demonstrate results in a small subset of the scope of claim 1. The data provided by the Applicant does not sufficiently provide evidence of unexpected results for every variation of the claimed composition (such, but not limited to, different heterocyclic thiols, different photoacid generators, and different novolak polymers). The results shown by the Applicant do not support the allegations that the claimed invention provides unexpectedly superior results in view of the prior art. Therefore, the Applicant’s arguments in this regard are not found to be persuasive.
With the above points considered, Applicant’s arguments are not considered persuasive and therefore the previous rejections are not withdrawn at this time.
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.
Claim(s) 1-19 and 21-29 are rejected under 35 U.S.C. 103 as being unpatentable over US 2014/0154624 A1(hereby referred to as Liu) in view of US 5942369 A (hereby referred to as Ota).
Regarding Claims 1, 3-8 and 10-14, Liu discloses a positive working photosensitive material. The positive working photosensitive composition comprises at least one photoacid generator, a polymer comprising one or more (meth)acrylic repeat units, and a heterocyclic thiol compound (paragraph 0010). In one of the synthesis examples, Liu discloses the following polymer comprising (meth)acrylic repeat units (paragraph 0046).
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From left to right, the repeat units depicted in the above polymer correspond to the repeat units (1), (6), (2), (4), and (5) as recited by instant claim 1. The repeat units in the above polymer also correspond to repeat units (1), (6a), (2a), (4a), and (5), respectively, as recited by instant claim 13. The structure corresponds to a polymer wherein repeat unit (1) is present in an amount of 7.5% (by mol), repeat unit (6) is present in an amount of 10% (by mol), repeat unit (2) is present in an amount of 17.5% (by mol), repeat unit (4) is present in an amount of 30% (by mol), and repeat unit (5) is present in an amount of 35% (by mol), which satisfies the requirements of instant claim 1. The heterocyclic thiol compound utilized by Liu is represented by either formula (3) or (4) (paragraph 0010). Specific examples of the thiol compound are provided in paragraphs 0014-0016 of Liu, wherein the specific examples include those recited by instant claim 8. Further, the examples utilize 1,3,5-triazine-2,4-6-trithiol (see paragraphs 0059-0062), which is recited by instant claim 8. The composition may further comprise a novolak polymer (paragraph 0021), and Liu discloses that the novolak polymers used had a dissolution rate in 2.38% aqueous TMAH (tetramethylammonium hydroxide) solution of more than 50 angstroms/sec (paragraph 0029 and 0050). The Examiner notes that a 2.38% aqueous solution of TMAH has a molar concentration of 0.26 M. Liu discloses that the composition includes a photoacid generator (paragraph 0017). Liu discloses that diazonaphthoquinone sulfonate esters may be used as the photoacid generator, and that two or more types of photoacid generators may be used in combination (paragraph 0017). Liu does not explicitly describe the amount of photoacid generator present in the composition, but Liu teaches specific examples of formulations (paragraph 0059-0068). Formulation 10, for instance, teaches a composition comprising 45% solids, wherein the solids comprise the novolak resin, an acrylic polymer, a plasticizer, a photoacid generator (PAG), a heterocyclic thiol, and a surfactant (paragraph 0068). The total mass of solids is about 100.19 grams. The total amount of PAG represents 0.7885 grams of the solids, which is equivalent to about 0.79 wt% of total solids.
However, Liu does not disclose the DNQ-type compounds recited by instant claims 1 and 3-6. Ota teaches a positive photoresist composition. The composition taught by Ota comprises an alkali-soluble novolak resin, an alkali-soluble acrylic resin containing several repeating units, a quinonediazide group-containing compound, and a solvent (Ota, Col. 2 Line 5-18). Ota teaches that the quinonediazide group-containing compound is synthesized by reacting a naphthoquinonediazide group-containing sulfonic acid with one of (i) a polyhydroxybenzophenone, (ii) a bis(poly)hydroxyphenylalkane, (iii) a tris (hydroxyphenyl)methane, (iv) a bis(cyclohexylhydroxyphenyl)(hydroxyphenyl)methane, (v) an aromatic compound having a phenolic hydroxyl group, or (vi) a novolak resin (Ota, Col. 5 Line 27-Col. 6 Line 37). The same section of Ota teaches specific examples of each of these types of compounds. When these compounds react with the naphthoquinonediazide group-containing sulfonic acid, the DNQ PACs recited by instant claims 1 and 3-6 are obtained. Ota further teaches that the DNQ PAC compounds may be used singly or in combination of two or more (Ota, Col. 6 Line 48-51).
Liu and Ota are analogous art because both references pertain to positive photosensitive compositions. It would have been obvious to one having ordinary skill in the art at the time of the filing date of the instant application to include the quinonediazide group-containing compounds taught by Ota in the photosensitive composition disclosed by Liu because the inclusion of a quinonediazide group-containing compound yields a photoresist composition that has good substrate adhesion and exhibits sufficient patterning resolution (Ota, Col. 2 Line 19-27). Furthermore, the quinonediazide group-containing compound offers improved pattern transfer performance when used in a photosensitive composition (Ota, Col. 6 Line 52-60). As noted above, Liu suggests photoacid generators make up about 0.79 wt% of total solids in the composition, and thus the combination of the DNQ-PAC compound with another photoacid generator would satisfy the ranges recited by instant claim 1.
Regarding Claim 2, Liu discloses that the photoacid generator may be a diazonaphthoquinone sulfonate ester in combination with onium salts, dicarboximidyl sulfonate esters, oxime sulfonate esters, diazo(sulfonyl methyl) compounds, disulfonyl methylene hydrazine compounds, nitrobenzyl sulfonate esters, biimidazole compounds, diazomethane derivatives, glyoxime derivatives, β-ketosulfone derivatives, disulfone derivatives, sulfonic acid ester derivatives, imidoyl sulfonate derivatives, and/or halogenated triazine compounds (paragraph 0017).
Regarding Claim 9, Liu discloses that the photoacid generator may be one of onium salts, dicarboximidyl sulfonate esters, oxime sulfonate esters, diazo(sulfonyl methyl) compounds, disulfonyl methylene hydrazine compounds, nitrobenzyl sulfonate esters, biimidazole compounds, diazomethane derivatives, glyoxime derivatives, β-ketosulfone derivatives, disulfone derivatives, sulfonic acid ester derivatives, imidoyl sulfonate derivatives, halogenated triazine compounds, diazonaphthoquinone sulfonate esters or combinations thereof (paragraph 0017). Thus, it would have been obvious to use one or more of these photoacid generator compounds in the composition obtained from the combination of Liu and Ota.
Regarding Claim 15, the polymer disclosed by Liu (depicted above in the rejection of claims 1 and 13) utilizes a t-butyl group as the acid cleavable group. Liu also discloses that the acid cleavable group (defined as G in Liu) may be a t-butyl group, a tetrahydropyran-2-yl group, a tetrahydrofuran-2-yl group, a 4-methoxytetrahydropyran-4-yl group, a 1-ethoxyethyl group, a 1-butoxyethyl group, a 1-propoxyethyl group, a 3-oxocyclohexyl group, a 2-methyl-2-adamantyl group, a 2-ethyl-2-adamantyl group, a 8-methyl-8-tricyclo[5.2.1.0 2,6]decyl group, a 1,2,7,7-tetramethyl-2-norbornyl group, a 2-acetoxymenthyl group, a 2-hydroxymethyl group, a 1-methyl-1-cyclohexylethyl group, a 4-methyl-2-oxotetrahydro-2H-pyran-4-yl group, a 2,3-dimethylbutan-2-yl group, a 2,3,3-trimethylbutan-2-yl group, a 1-methyl cyclopentyl group, a 1-ethyl cyclopentyl group, a 1-methyl cyclohexyl group, 1-ethyl cyclohexyl group, a 1,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-yl group, a 2-ethyl-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl group, a 2,6,6-trimethylbicyclo[3.1.1]heptan-2-yl group, a 2,3-dimethylpentan-3-yl group, or a 3-ethyl-2-methylpentan-3-yl group (paragraph 0032). Thus, it would have been obvious to use any of these acid cleavable groups in the polymer used in the photosensitive composition obtained from the combination of Liu and Ota.
Regarding Claims 16-17, the polymer disclosed by Liu (depicted above in the rejection of claims 1 and 13) utilizes a t-butyl group as the acid cleavable group. The other repeat units depicted in the polymer correspond to components (1a), (6b), (2b), and (4b), respectively, as recited by instant claim 16. As noted above, Liu discloses that the acid cleavable group may be a different moiety, such as a 1-ethyl cyclopentyl group (Liu, paragraph 0032). Furthermore, Liu provides a synthesis example wherein the polymer comprises a 1-ethyl cyclopentyl group as the acid cleavable group (see Synthesis Example 4, paragraph 0048 of Liu). Thus, it would have been obvious to replace the t-butyl group in the polymer disclosed by Liu (depicted above) with a 1-ethyl cyclopentyl group because Liu recognizes this group as a known alternative and functional equivalent for the acrylic polymer used in the composition obtained from the combination of Liu and Ota. See MPEP 2144.06 II. In this alternative embodiment, wherein the t-butyl group in the polymer depicted above is replaced with a 1-ethyl cyclopentyl group, the polymer has the compositional makeup the satisfies the ranges of repeat units recited by instant claim 17.
Regarding Claim 18, Liu discloses that the polymer may further comprise a styrenic repeat unit having the same structure as that recited by instant claim 18 (paragraph 0022). The styrenic repeat unit disclosed by Liu is equivalent in that R4 of Liu corresponds to R14 of instant claim 18 when R4 is chosen to be H or CH3, and R5 and R6 of Liu corresponds to R14’ and R14’’, respectively, wherein R5 and R6 can be the same or different and are chosen from H, OH, OCOOR7, or OCOCOOR7, wherein R7 is an acid cleavable group, such as t-butyl (Liu, paragraph 0022). Thus, it would have been obvious to include a styrenic repeat unit in the polymer disclosed by Liu in the composition obtained from the combination of Liu and Ota.
Regarding Claim 19, Liu discloses that the polymer may further comprise monomer repeat units that impart etching resistance, modify the dissolution characteristics of the polymer, modify photosensitivity, modify adhesion, or impart other useful characteristics (paragraph 0023). Such monomers may include lactones (paragraph 0023), including mevalonic lactone methacrylate (paragraph 0024). While Liu does not include an example comprising the instantly claimed monomer units, as Liu teaches their suitability, it would have been obvious to the ordinarily skilled artisan before the effective filing date of the instant application, in the absence of unexpected results, to have included them with the expected effect of imparting useful characteristics and thereby arrive at the instantly claimed composition according to instant claim 19.
Regarding Claims 21-25, Liu discloses that the novolak resin is obtained from the condensation of a phenolic compound, such as phenol, o-cresol, m-cresol, p-cresol, 2-5-xylenol and the like, with an aldehyde compound such as formaldehyde in the presence of an acid or multivalent metal-ion catalyst (paragraph 0029). The novolak polymer is preferably formed from m-cresol to obtain a dissolution rate of 1000 angstroms/sec in a TMAH solution (paragraph 0029). Exemplary cresylic novolak polymers may comprise, for instance, 0-60 mol% p-cresol, 0-20 mol% o-cresol, and 0-80 mol% m-cresol (paragraph 0030). In some embodiments, the polymer may comprise 50-100 mol% of the m-cresol (paragraph 0030). The novolak resin disclosed by Liu is produced using similar or identical components as the novolak resin of the instant invention (compare paragraph 0029-0030 of Liu with paragraph 0057-0058 of the instant application’s specification). Thus, it would be expected that the novolak resin disclosed by Liu inherently possesses the same repeating units as those recited by instant claims 21-23. Likewise, it would be expected that the novolak resin disclosed by Liu would have a solid content between 10 to 90 wt% due to the similar or identical synthesis method. Therefore, it would be obvious to have a novolak resin having the characteristics recited by instant claims 21-25 in the composition disclosed by the combination of Liu and Ota.
Regarding Claims 26-28, Liu discloses that the photosensitive composition is applied to a substrate by spin coating the composition (paragraph 0056-0057). The photosensitive composition is soft baked and then exposed with radiation to image the photosensitive layer (paragraph 0057-0058). Following the imaging, the photoresist is post exposure baked and then developed using a TMAH solution (paragraph 0058). Liu further discloses that the substrate may be a copper substrate, which is a chalcophile material (paragraph 0056). Thus, it would have been obvious to form a positive relief image using the composition obtained from the combination of Liu and Ota.
Regarding Claim 29, this claim is drawn to the intended use of the photosensitive composition. Furthermore, Liu discloses the use of the photosensitive composition to form a positive relief image (Liu, paragraph 0013). Thus, it would have been obvious to use the composition obtained from the combination of Liu and Ota to form a positive relief image.
Claim(s) 20 is rejected under 35 U.S.C. 103 as being unpatentable over US 2014/0154624 A1(hereby referred to as Liu) in view of US 5942369 A (hereby referred to as Ota) as applied to claim 1 above, and further in view of US 2003/0057610 A1 (hereby referred to as Kunita).
Regarding Claim 20, the combination of Liu and Ota discloses a photosensitive composition comprising an acrylic polymer, a heterocyclic thiol compound, a photoacid generator, a novolak resin, and a DNQ-PAC, as discussed above in regards to the rejection of instant claim 1. Liu further discloses that the acrylic polymer may contain additional monomer repeat units, including lactones (Liu, paragraph 0023-0024).
However, neither Liu nor Ota disclose a lactone repeat unit according to instant claim 20. Kunita teaches a positive image-forming material. The image-forming material taught by Kunita comprises an alkali-soluble resin comprising a (meth)acrylic repeating unit (Kunita, paragraph 0039). Kunita teaches that the resin may further contain a lactone structure, including units (a3) and (a5), which are depicted below (Kunita, paragraph 0135).
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The above structures (a3) and (a5) are equivalent to the lactone structure recited by instant claim 20, in the case that R15 and m recited by instant claim 20 are CH3 and 2, respectively.
Liu, Ota, and Kunita are analogous art because each reference pertains to positive photosensitive compositions. It would have been obvious to one having ordinary skill in the art at the time of the filing date of the instant application to include a lactone monomer having the structure of (a3) or (a5), as taught by Kunita, in the acrylic polymer included in the composition obtained from the combination of Liu and Ota because including a lactone structure such as (a3) or (a5) in the acrylic polymer can improve the solubility of the resin in an alkaline solution (see Kunita, paragraph 0129).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. JPH07152152A teaches positive resist compositions that include a photosensitizer containing a quinonediazide sulfonic acid ester of a phenolic compound. The Examiner’s understanding is that the compounds taught by JPH07152152A include the NK-280 DNQ-PAC utilized by the instant application. The Applicant should consider this prior art when formulating a future response.
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/JAYSON D COSGROVE/Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734
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