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 .
Election/Restrictions
Applicant’s election of Species A in the reply filed on June 22, 2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Therefore, claims 1-8 and 15-26 are pending, with claims 3-8 withdrawn from consideration as being directed to non-elected species.
Claims 9-14 have been canceled.
Claim Objections
Claims 15 and 18 are objected to because of the following informalities: the limitations “molecular weight of about 30 to about 2000” in claims 15 and 18 should be amended to read “molecular weight of about 30 to about 2000 g/mol”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
Claims 2 and 21-26 are 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 2 recites for the substituents R1 and R3 the broad recitations “hydrocarbon, substituted hydrocarbon”, and the claim also recites “aryl, heteroaryl” which are the narrower statements of the range/limitation.
It is well-known that an aryl group is a specific examples of hydrocarbon group, as evidenced in par.0026 of Noda et al. (US 2019/0332010).
A heteroaryl is a specific example of substituted hydrocarbon.
The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claims 21-26 are rejected as being dependent on the rejected claim 2.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraph of 35 U.S.C. 102 that forms 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.
Claims 1, 2, 15, 16, and 19-23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Nakano et al. (US 2001/0021482).
With regard to claims 1, 16, and 19, Nakano et al. teach a photoresist composition comprising a polymer, a photoacid generating agent, trimethylol propane trigycidyl ether, and a solvent (par.0059, Embodiment 15 in par.0064). The photoresist solution is coated onto a silicon substrate, and it is baked to form a photoresist film (par.0060). The photoresist film is exposed to radiation and it is developed to form a photoresist pattern (par.0062).
The trimethylol propane trigycidyl ether is represented by the formula:
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and it is an “additive comprising at least one cyclic ether group” in claims 1 and 19.
The mixture of a polymer and a photoacid generating agent is the “photoresist” in claims 1 and 19.
The step of coating the photoresist solution on a silicon substrate of Nakano et al. is the step of “coating a substrate with a photoresist solution that includes a photoresist and an additive” in claim 1, and to the step of “coating a substrate with a photoresist solution, wherein the photoresist solution comprises an additive” in claim 19 of the instant application.
The steps of baking to form a photoresist film, exposing the resist film, and developing the exposed resist film of Nakano et al. are the steps of “pre-baking the applied photoresist solution to form a photoresist layer, exposing the photoresist layer to radiation to pattern the photoresist layer, and developing the photoresist layer to obtain a patterned photoresist layer” in claims 16 and 19 of the instant application.
Therefore, the process in Embodiment 15 of Nakano et al. anticipates the methods in claims 1, 16, and 19 of the instant application.
With regard to claim 2, trimethylol propane trigycidyl ether of Nakano et al. is a compound of formula (1-A), wherein m=0, n=3, R1 is CH3-CH2-C- (hydrocarbon group), and L is -CH2-O-CH2- (a combination of -O- and hydrocarbon groups).
With regard to claim 15, trimethylol propane trigycidyl ether of Nakano et al. has a molecular weight of 212g/mol. This value is within the claimed range.
With regard to claim 20, trimethylol propane trigycidyl ether of Nakano et al. comprises epoxy groups, and the epoxy group is capable of ring opening under the action of an acid, as evidenced in par.0242 of Araki et al. (US 2005/0191578).
With regard to claim 21, the examiner would like to note that claim 2 allows for m=0, so R2 is optional for the compounds of Formulas (I-A) and (I-B). Therefore, the limitations regarding the substituent R2 are optional.
With regard to claim 22, trimethylol propane trigycidyl ether of Nakano et al. is a compound of formula (1-A), wherein R1 is CH3-CH2-C- (alkyl group with 3 carbon atoms).
With regard to claim 23, trimethylol propane trigycidyl ether of Nakano et al. is a compound of formula (1-A) wherein L is -CH2-O-CH2- (a combination of -O- and alkyl groups).
Claims 1, 2, 15, 16, and 19-24 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hokino et al. (US 2010/0203445).
With regard to claims 1, 16, and 19, Hokino et al. teach a photoresist composition comprising a polymer, photoacid generating agent, the compound CLO-2, a basic solvent and a solvent (Examples 1-10 in Table 3 in par.0402). The photoresist solution is coated onto a substrate, and it is baked to form a photoresist film (par.0397). The photoresist film is exposed to radiation and it is developed to form a photoresist pattern (par.0397).
The compound CLO-2 is represented by the formula:
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and it is an “additive comprising at least one cyclic ether group” in claims 1 and 19.
The mixture of a polymer, photoacid generating agent, and basic compound is the “photoresist” in claims 1 and 19.
The step of coating the photoresist solution on a substrate of Hokino et al. is the step of “coating a substrate with a photoresist solution that includes a photoresist and an additive” in claim 1, and to the step of “coating a substrate with a photoresist solution, wherein the photoresist solution comprises an additive” in claim 19 of the instant application.
The steps of baking to form a photoresist film, exposing the resist film, and developing the exposed resist film of Hokino et al. are the steps of “pre-baking the applied photoresist solution to form a photoresist layer, exposing the photoresist layer to radiation to pattern the photoresist layer, and developing the photoresist layer to obtain a patterned photoresist layer” in claims 16 and 19 of the instant application.
Therefore, the process in Examples 1-10 of Hokino anticipates the methods in claims 1, 16, and 19 of the instant application.
With regard to claim 2, the compound CLO-2 of Hokino et al. is a compound of formula (1-B), wherein m=0, n=3, R1 is CH3-CH2-C- (hydrocarbon group), L is -CH2-O-CH2- (a combination of -O- and hydrocarbon groups), Ra and Rb are alkylene groups with 1 carbon atom, R3 is -CH2-CH3 (a hydrocarbon group).
With regard to claim 15, the compound CLO-2 of Hokino et al. has a molecular weight of 428g/mol. This value is within the claimed range.
With regard to claim 20, the compound CLO-2 of Hokino et al. comprises oxetanyl groups, and an oxetanyl group is capable of ring opening under the action of an acid, as evidenced in par.0242 of Araki et al. (US 2005/0191578).
With regard to claim 21, the examiner would like to note that claim 2 allows for m=0, so R2 is optional for the compounds of Formulas (I-A) and (I-B). Therefore, the limitations regarding the substituent R2 are optional.
With regard to claim 22, the compound CLO-2 of Hokino et al. is a compound of formula (1-B), wherein R1 is CH3-CH2-C- (alkyl group with 3 carbon atoms).
With regard to claim 23, the compound CLO-2 of Hokino et al. is a compound of formula (1-B) wherein L is -CH2-O-CH2- (a combination of -O- and alkyl groups).
With regard to claim 24, the compound CLO-2 of Hokino et al. is a compound of formula (1-B) wherein R3 is -CH2-CH3 (alkyl group with 2 carbon atoms).
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 17 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Chang et al. (US 2017/0271150) in view of Nakano et al. (US 2001/0021482).
With regard to claim 17, Chang et al. teach a photoresist composition comprising a polymer, a metal complex, a multi-metallic complex, a photoacid generator, a quencher (base) and a solvent (par.0040). The photoresist is applied to a substrate as a solution (par.0025).
The photoresist composition of Chang et al. is a metallic photoresist.
Chang et al. teach that the multi-metallic complex may comprise a crosslinking group, such as an epoxy group (par.0040), but fail to teach an additive comprising at least one cyclic ether group.
Nakano et al. teach a photoresist composition comprising a polymer with epoxy groups R4, photoacid generating agent, and a multifunctional epoxy crosslinking compound (abstract). Nakano et al. specifically teach that the addition of an epoxy-containing crosslinking compound to a polymer comprising epoxy groups allows for improved resolution and for the formation of a fine pattern (Table 4 in par.0064, and par.0065).
It would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to include an epoxy-containing crosslinking compound in the photoresist of Chang et al., in order to form a fine pattern and improve the resolution.
An epoxy-containing crosslinking compound of Chang modified by Nakano is an additive comprising at least one cyclic ether group.
With regard to claim 18, Nakano et al. teach that the epoxy-containing crosslinking compound may be trimethylol propane triglycidylether (Example 15 in Table 4, par.0064). This compound has a molecular weight of 212 g/mol. This value is within the claimed range.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Takizawa et al. (US 2016/0147154) teach a radiation-sensitive composition comprising a resin (A) and a crosslinking agent (C)(abstract), wherein the crosslinking agent (C) may be represented by the formulas:
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398
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208
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116
134
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314
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216
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(par.0422).
Hatakeyama et al. (US 2006/0188809) teach a resist composition which may comprise a crosslinker compoun such as tris(2,3-epoxypropyl)isocyanurate, trimethylolmethane trigycidyl ether, trimethylolpropane trigycidyl ether, triethylolethane triglycidyl ether (par.0448).
Chen et al. (US 2021/0271164) teach a photoresist composition comprising a photoactive compound, a polymer, and a crosslinker. The crosslinker is a monomer, oligomer, or polymer including a structure of formula:
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(abstract). The photoresist composition may comprise:
- a phosphonic acid, such as phenylphosphonic acid (par.0068);
-a coloring agent, such as 3-ethyl-2-cyano-3,3-diphenyl acrylate and 2’-ethylhexyl-3,3’-diphenylacrylate (par.0072); or
-adhesion additives, such as g-methacryloxypropyl trimethoxysilane, vinyl trimethoxysilane, vinyltriacetoxysilane (par.0073).
Wang et al. (US 2014/0255851) teach a photoresist composition (abstract), and the photoresist composition may comprise N-methoxymethyl- or N-butoxymethyl-melamine (par.0037).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANCA EOFF whose telephone number is (571)272-9810. The examiner can normally be reached Mon-Fri 10am-6:30pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Niki Bakhtiari can be reached at (571)272-3433. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ANCA EOFF/Primary Examiner, Art Unit 1722
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