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 .
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 08/15/2023 is being considered by the examiner.
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) 1-5 are is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Cui et al (US 20240019779, with filing date 05/20/2022).
Regarding Claim 1-5, Cui discloses compounds and photoresist compositions including these compounds, wherein the compounds of Cui are represented by formula (1) as presented in the abstract and at [0006]-[0010], [0021]-[0070].
In the synthetic examples at [0164]-[0186], the following reaction schemes are provided:
PNG
media_image1.png
270
736
media_image1.png
Greyscale
PNG
media_image2.png
226
590
media_image2.png
Greyscale
PNG
media_image3.png
262
748
media_image3.png
Greyscale
PNG
media_image4.png
234
590
media_image4.png
Greyscale
PNG
media_image5.png
482
620
media_image5.png
Greyscale
Each of the compounds SM2, SM3, and SM4 are isolated and characterized via proton-NMR as per [0164]-[0186] – these are not transient intermediates formed in-situ that remain un-isolated before being consumed in subsequent reactions.
SM2, SM3, and SM4 meet the limitations of the claim for where they are each compounds having a phenyl group core, a first substituent comprising an enol ether group, a second substituent comprising an acid labile group (the ester group), and a third substituent that is a halogen – iodine.
Further, these compounds meet the limitations of claims 2-5 for where, as per claimed Formula 1:
X is iodine (claim 3)
Subscript a is 1 or 2
L1 is a single bond
R1 is an ester (C(=O)-O-) linkage to an ethyl cyclohexyl or a dimethyl benzyl group (acid-cleavable from the ester linkage) (claim 4)
Subscript b is 1
L2 is an oxyethyl (O-CH2-CH2-) linkage
All R2 are each H
Subscript c is 1 (claim 5)
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claim(s) 8-17 are rejected under 35 U.S.C. 103 as being unpatentable over Cui et al (US 20240019779, with filing date 05/20/2022). as applied to claim 1 above, and further in view of Hatakeyama et al (US 20110294070).
Regarding claim 8-17, Cui discloses the limitations of the claim as discussed above regarding claim 1.
Cui however does not disclose a monomer comprising the reaction product of a compound according to claim 1 and a monomer precursor group comprising a polymerizable group and a group chosen from hydroxyl or carboxylic acid, wherein the reaction product comprises an acetal or ketal linker formed by the reaction of the enol ether or halomethyl ether of the compound and the hydroxyl/carboxylic acid group of the precursor. Cui does disclose that the monomers MD2-MD4 are made by forming an acetal linkage between the SM2-SM4 compounds and a hydroxyl-bearing component, but not one with a polymerizable group.
This limitation is met by Hatakeyama.
Hatakeyama discloses a monomer, polymer, chemically amplified resist, and method of patterning using such (Abstract).
The polymer of Hatakeyama is described from [0037]-[0108].
Preferred units in the polymer conform to formula (2), the polymerized embodiment(s) of an acrylate monomer conforming to formula (1) in [0041]:
PNG
media_image6.png
166
340
media_image6.png
Greyscale
Wherein R1 is a hydrogen or methyl, R2 is hydrogen or C1-C4 alkyl, R3 is an acid labile group. A synthetic method for making the monomers is discussed from [0044]-[0052], wherein a phenolic hydroxyl group is protected with a functionality – this makes the acid-labile group OR3. Exemplary acid labile groups are discussed and depicted from [0053]-[0075], where acid labile groups may be acetals. As discussed in [0075], acid labile groups may be introduced into the monomer before polymerization – such introduction allows for greater control over the amount of acid labile group introduced into the polymer.
The resultant product of a monomer conforming to formula (2) and the compounds SM2-SM4 of Cui would result in a compound that meets the limitations of claims 8 and 9 where:
P is a group having a phenyl linkage connected to an acrylate or methacrylate polymerizable moeity.
One of each R4 are each H and Me, respectively
L3 is a single bond
Subscript c is 1
X is iodine
Subscript a is 1 or 2
L1 is a single bond
R1 is an ester (C(=O)-O-) linkage to an ethyl cyclohexyl or a dimethyl benzyl group (acid-cleavable from the ester linkage)
Subscript b is 1
L2 is an oxyethyl (O-CH2-CH2-) linkage
The polymer resulting from polymerization of the monomer product of Cui and Hatakeyama meets the limitations of claim 10.
Hatakeyama also discloses at [0075] that the polymer of Hatakeyama may be polymerized and then afterwards an acid labile group may be introduced thereon. The resultant polymer bears the same structural components described above, meeting the limitations of claims 11 and 12. As the repeat unit described above is based on a phenolic acrylate/methacrylate, the vinyl group therein meets the limitations of the claim 13.
The polymer of Hatakeyama comprises further repeat units (b), which include those having lactone groups ([0076]-[0080] (claim 14).
The polymer of Hatakeyama is dissolved in a solvent such as cyclohexanone or another listed in [0110], along with an acid generator ([0112]) to form a photoresist composition ([0110]-[0118]) (claims 15 and 16). This photoresist composition is then used in a pattern formation method wherein it is applied onto a substrate, exposed to radiation, and then developed to provide a relief pattern (claim 17). The polymer resist of Hatakeyama is purported to improve acid diffusion characteristics at [0022] and [0024].
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention from routine experimentation with phenolic protection to incorporate the vinyl ether compounds of Cui into the monomer/polymer of Hatakeyama in pursuit of polymer/monomer having an acid labile group having multiple labile regions and thus improved acid diffusion characteristics.
Allowable Subject Matter
Claims 6 and 7 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.
The following is a statement of reasons for the indication of allowable subject matter:
The closest prior art is as follows:
Cui et al (US 20240019779 A1, filed 05/20/2022)
Hatakeyama et al (US 20110294070 A1)
Hou et al (US 2022/0137509 A1)
Aqad et al (US 20190202955 A1)
Of the above references, only Cui discloses a compound that meets the limitations of the independent claim 1, detailing enol ether compounds as disclosed in the experimental examples. 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 above references. The subject matter of claims 6 and 7 appears novel and nonobvious over prior art but remains objected to as dependent from rejected claim 1.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANDREW PRESTON TRAYWICK whose telephone number is (571)272-2982. The examiner can normally be reached Monday - Friday 8-5.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark Huff can be reached at 571-272-1385. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/A.P.T./Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734