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 .
Response to Arguments
Applicant’s Arguments regarding the rejections made over 35 USC 102(a)(2) and rejections over 35 USC 103 made in the prior office action are considered persuasive. As such all rejections are withdrawn,
After further search and consideration, however, the examiner makes a new grounds of rejection.
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(s) 1-3, 5 are is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Paraja et al (Miguel Paraja, M. Carmen Pérez-Aguilar, Carlos Valdés; The Pd-catalyzed synthesis of benzo-fused carbo- and heterocycles through carbene migratory insertion/carbopalladation cascades with tosylhydrazones. Chem. Commun. 2015; 51 (90): 16241–16243.)
As a matter of claim interpretation – the claims rejected herein recite “a compound” and are thus not required to be of a field of endeavor that is similar to the dependent claims. The dependent claims do not recite “a photoresist” until claim 15.
Regarding Claim 1-3, 5, Paraja disclsoses a palladium catalyzed cross-coupling reaction between o-iodoallylbenzene and tosylhydrazone s to arrive at benzo-fused carbocycles and heterocycles.
In Table 2, a set of experiments were performed to create indanes, using iodoenolethers and tosylhydrazones.
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Experiments 7k and 7l use the compound 6 where x is a methoxy group.
This compound meets the limitations of the claims where it has an aromatic core (phenylene ring), a halogen (iodine), an enol ether, and an acid labile group (the methoxy group)
The compound meets the limitations of claim 2 where:
Ar1 is a phenylene ring
X is I, a is 1
When X is I, claim 3 is met
L1 is a single bond, b is 1
R1 is a methoxy group (acid labile group)
L2 is a single bond, c is 1
R2 are each H
Claim(s) 1-2 and 4-5 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Takeuchi et al (US 20110263661 A1),
Regarding claims 1-2 and 4-5, Takeuchi discloses sphinosine-1 phosphate receptor modulators for treating a variety of disorders (Abstract).
As an intermediate step in the synthesis of one such receptor, ethyl 3-bromo-4 -(vinyloxy)benzoate is synthesized and isolated.[AltContent: rect]
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This compound meets the limitations of the claims where it has an aromatic core (phenylene ring), a halogen (bromine), an enol ether, and an acid labile group (the ethyl ester group)
The compound meets the limitations of claim 2 where:
Ar1 is a phenylene ring
X is Br, a is 1
L1 is a single bond, b is 1
R1 is an ethyl ester group (acid labile group)
L2 is a single bond, c is 1
R2 are each H
Allowable Subject Matter
Claims 6-17 are 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.
The claims objected to are directed to embodiments of the compound of claim 1, wherein the subscript c corresponding to the number of vinyl ether or halomethyl ether functionalities is 2, and where linking group L2 comprises a sulfonyl (-SO2-) group. Additionally, the claims are directed to a monomer made from the reaction of the compounds of claim 1 with a monomer precursor having a hydroxyl or carboxylic acid group, and a polymer made from the polymerization of the monomer, as well as a polymer made by reacting the compound of claim 1 with a polymer having hydroxyl or carboxylic acid groups in the sidechain. Further claims objected to include dependent claims comprising the polymer made from the compound of claim 1 where the polymer bears additional repeat units such as those having an acid-labile group, or other group, and a photoresist composition comprising the polymer and a solvent and a photoacid generator – as well as a pattern formation method using the photoresist composition.
The following is a statement of reasons for the indication of allowable subject matter:
The closest prior art is as follows:
Takeuchi et al (US 20110263661 A1)
Paraja et al (Chem. Comm. 2015)
Hatakeyama et al (US 20110294070 A1)
Hou et al (US 2022/0137509 A1)
Aqad et al (US 20190202955 A1)
Of the above references, only Takeuchi and Paraja disclose compounds that meet the limitations of the independent claim 1 and claims 2-5, detailing enol ether compounds as disclosed in the experimental examples. However, they fail to disclose or suggest any of the limitations of the dependent claims such as a photoresist or a polymer.
Hatakeyama, Hou, and Aqad all generally disclose vinyl compounds used for photoresist components, but the compounds disclosed and discussed are not similar to the compounds of claim 1 due to primarily being acrylates (not enol ethers or halomethyl ethers), and no discussion of a compound wherein 2 halomethyl ether or enol ether groups are present on a halo-substituted aryl/heteroaryl core bearing an acid labile group thereupon is given in these references. Further, there is no discussion of a compound meeting the limitations of the claim 1 wherein a sulfonyl group is present in any of the three aforementioned references. There is no locus between the references Hatakeyama, Hou, and/or Aqad and the two references that disclose the limitations of claims 1-5 that would enable a person having ordinary skill in the art to arrive at the claimed invention as the references are in different fields of endeavor. The subject matter of claims 6-17 appears novel and nonobvious over prior art but remains objected to as dependent from rejected claim 1.
Conclusion
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/A.P.T./Examiner, Art Unit 1737
/John S. Chu/Primary Examiner, Art Unit 1737
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