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 .
Drawings
The drawings are objected to as failing to comply with 37 CFR 1.84(p)(5) because they include the following reference character(s) not mentioned in the description: (14) (as shown in Fig. 6). Corrected drawing sheets in compliance with 37 CFR 1.121(d), or amendment to the specification to add the reference character(s) in the description in compliance with 37 CFR 1.121(b) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
The Examiner notes that all the monomers and/or intermediates labeled in Figs. 3-7 as (1) through (19), with the exception of intermediate (14), as shown in Fig. 6, are defined within the specification. Appropriate correction should be made by the Applicant.
Claim Rejections - 35 USC § 102
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.
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) 1-9 and 14-20 are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over US 20230174471 A1 (hereby referred to as Ahn).
Regarding Claim 1 and 16, Ahn discloses an acetal-based polymer and a photoresist composition comprising the same. Ahn further teaches a pattern forming method (Ahn, paragraph 0146). The pattern forming method includes providing the photoresist film comprising the acetal-based polymer on a substrate (Ahn, paragraph 0149), selectively exposing the photoresist film to radiation through a photomask (Ahn, paragraph 0151), and developing the patterned photoresist layer using a developer solution (Ahn, paragraph 0153). The photoresist layer may be post-exposure baked (Ahn, paragraph 0152). The acetal moiety in the polymer chain included in the photoresist composition acts an acid labile functional group that is cleaved in response to light exposure in combination with an acid generator (Ahn, paragraph 0041). Thus, Ahn anticipates the invention according to instant claim 1. Ahn discloses that the acetal-based polymer is included with a photoacid generator and a quencher to form a photoresist composition (Ahn, paragraph 0132, 0137, and 0228-0229).
Regarding Claims 2, 15, and 17, Ahn discloses that the acetal-based polymer comprises an acetal-based compound polymerized with a first monomer having a polar group and a second monomer having an acid labile group (Ahn, paragraph 0069). The first monomer having a polar group has a structure represented by Formula 4 (Ahn, paragraph 0080) and the second monomer having an acid labile group has a structure represented by Formula 5 (Ahn, paragraph 0084), both of which are reproduced below.
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Formula 4 represents a styrene monomer and Formula 5 represents a (meth)acrylate monomer. At least one of the substituents on the benzyl ring in Formula 4 (R14 to R18) is a polar group (Ahn, paragraph 0081), such as a hydroxyl group (Ahn, paragraph 0082). In Formula 5, R24 represents an acid labile group (Ahn, paragraph 0085), such as a t-butyl group (Ahn, paragraph 0086). Furthermore, Ahn teaches that the acetal-based polymer may be an polymer represented by Formula 10 (Ahn, paragraph 0117), the structure of which is reproduced below.
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Formula 10 is a polymer which comprises an acid-labile group in the backbone (the acetal group), as well as a comonomer having an acidic leaving substituent (the repeat units denoted by the subscripts a1 and b2) and a comonomer having a polar substituent and/or a proton-donating substituent (the repeat units denoted by the subscripts b1 and a2). The polymer is a linear copolymer. Thus, Ahn anticipates the polymer according to instant claims 2 and 15.
Regarding Claim 3, Ahn discloses that in the acetal-based polymer represented by Formula 10, which is reproduced above, the molar ratio of the styrenic repeating unit and the methacrylic repeating unit (e.g. the second/third comonomer and the first comonomer, respectively) is 1:9 to 9:1 (Ahn, paragraph 0122). In an inventive example, Ahn discloses that the ratio of the styrenic and methacrylic repeating units was 1:1 (Ahn, paragraph 0214). In such an embodiment, the first comonomer has a molar ratio of 50% of the oligomer and the second (or third, since the styrenic monomer satisfies the definition of both the second and the third comonomer) has a molar ratio of 50% of the oligomer. Thus, Ahn anticipates the invention according to instant claim 3.
Regarding Claim 4, the polymer represented by Formula 10, which is reproduced above, comprises an acetal group as the acid-labile group. The polymer has an acetal group located at the chain center (Ahn, paragraph 0069).
Regarding Claim 5, Ahn discloses that the acetal-based polymer has a molecular weight of about 1,500 g/mol to 20,000 g/mol (Ahn, paragraph 0111). Ahn further teaches that the molecular weight may be varied to achieve desired properties such as mechanical properties and performance (Ahn, paragraph 0111). The molecular weight range taught by Ahn corresponds to an overlap with the number of oligomers recited by instant claim 5. In the alternative, one having ordinary skill in the art would be motivated to optimize the number of repeating units in the polymer to achieve desired mechanical properties of the polymer. Refer to MPEP 2144.05 II.
Regarding Claim 6, Ahn discloses that the acetal-based polymer includes a chain transfer agent (CTA) used for RAFT polymerization (Ahn, paragraph 0050).
Regarding Claim 7, Ahn discloses that the CTA used for RAFT polymerization may be a trithiocarbonate or a dithioester (Ahn, paragraph 0046, see Formulae 2 and 2a).
Regarding Claim 8, Ahn discloses that the second polymerizable monomer having an acid labile group (which is analogous to the first comonomer of the instant application) is an alkyl acrylate monomer (Ahn, paragraph 0084-0086, see Formula 5).
Regarding Claim 9, Ahn discloses that the first polymerizable having a polar group (which is analogous to the second and/or third comonomer of the instant application) is a styrene monomer having a polar group such as a hydroxyl group, an acetal group, or an ester group (Ahn, paragraph 0080-0082, see Formula 4).
Regarding Claim 14, Ahn discloses that the acetal-based polymer is terminated with the RAFT chain transfer agent (Ahn, paragraph 0097-0099).
Regarding Claims 18-20, Ahn discloses that the acetal-based polymer is produced by using a RAFT agent into which an acid-labile group is introduced, to have a structure with an acetal group located at the chain center (Ahn, paragraph 0069). The acetal-based compound is then reacted with a first polymerizable monomer having a polar group and a second polymerizable monomer having an acid labile group to obtain the acetal-based polymer (Ahn, paragraph 0069). Refer to paragraphs 0182-0206 of Ahn for a specific example of the process. The acetal group (the acid-labile group) is attached to a spacer core (Ahn, paragraph 0182) and may be further reacted with a chain extending compound (Ahn, paragraph 0207-0212). The RAFT initiator comprises two reactive groups (Ahn, paragraph 0189).
Claim(s) 10-13 are rejected under 35 U.S.C. 103 as being unpatentable over US 20230174471 A1 (hereby referred to as Ahn) in view of JP 2013101222 A (hereby referred to as JP ‘222).
Regarding Claims 10-11, Ahn discloses an acetal-based polymer comprising an acid-labile group, a monomer having an acid leaving group, and a monomer having a polar group (refer to Formula 10 above). However, Ahn is silent in regards to the polar group-containing comonomer being an acrylate monomer having a polar substituent.
JP ‘222 teaches a resist composition for forming a resist pattern. The resist composition comprises a polymeric material whose solubility in developer changes due to the action of an acid (JP ‘222, paragraph 0015 of the English translation). The polymeric material may comprise a repeating unit containing a polar group (JP ‘222, paragraph 0132 of the English translation). The repeating unit having a polar group is preferably represented by formula (a3-1) (JP ‘222, paragraph 0219 of the English translation, refer to the formula on page 86 of JP ‘222). The repeating unit may be derived from acrylic acid (JP ‘222, paragraph 0226 of the English translation and formulas (a3-11) to (a3-13) on page 87 of JP ‘222). Specific examples of suitable repeating units are depicted on page 89-90 of JP ‘222 (JP ‘222, paragraph 0232 of the English translation), wherein the repeating units are (meth)acrylate monomers containing a polar substituent containing one or more oxygen atoms.
Ahn and JP ‘222 are analogous art because both references pertain to resist compositions and polymers included in the same. It would have been obvious to one having ordinary skill in the art before the filing date of the instant application to include a comonomer that is an acrylate with a polar substituent, as taught by JP ‘222, in the acetal-based polymer disclosed by Ahn because the inclusion of a polar substituent in the photoresist polymer yields increased polarity, which contributes to improved resolution of the developed pattern (JP ‘222, paragraph 0217 of the English translation).
Regarding Claims 12-13, Ahn discloses an acetal-based polymer comprising an acid-labile group, a monomer having an acid leaving group, and a monomer having a polar group (refer to Formula 10 above). However, Ahn is silent in regards to acetal-based polymer comprising a monomer having a photoacid generating substituent and/or a quenching substituent.
JP ‘222 teaches a resist composition for forming a resist pattern. The resist composition comprises a polymeric material whose solubility in developer changes due to the action of an acid (JP ‘222, paragraph 0015 of the English translation). The polymer comprises a constituent unit (a0) that includes a group represented by general formula (a0-1) or (a0-2) (JP ‘222, paragraph 0018 of the English translation, see page 10 of JP ‘222). An example of such a constituent unit is represented by formula (a0-11) (JP ‘222, paragraph 0081 of the English translation, see page 32 of JP ‘222), which is an acrylate-based repeating unit having a photoacid generating substituent. The content of the photoacid generating substituent-containing monomer in the entire polymer is preferably between 1 to 50 mol% based on the total constituent units of the polymer (JP ‘222, paragraph 0131 of the English translation).
Ahn and JP ‘222 are analogous art because both references pertain to resist compositions and polymers included in the same. It would have been obvious to one having ordinary skill in the art before the filing date of the instant application to include a comonomer that has a photoacid generating substituent, as taught by JP ‘222, in the acetal-based polymer disclosed by Ahn because the inclusion of a photoacid generating substituent in the photoresist polymer provides improved lithography characteristics such as sensitivity and resolution, as well as improved solubility in the photoresist solvent (JP ‘222, paragraph 0131 of the English translation).
Conclusion
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/JAYSON D COSGROVE/Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734
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