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 .
DETAILED ACTION
This Office action is based on the 18/659739 application originally filed May 09, 2024.
Amended claims 1-20, filed May 09, 2024, are pending and have been fully considered.
Claim Rejections - 35 USC § 102/103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1-20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jiang et al. (US 2019/0391486) hereinafter “Jiang”.
Regarding Claims 1-4
Jiang discloses in paragraph 0002, stable solutions of monoalkyl tin alkoxides and their hydrolysis and condensation products and particularly to the compositions of stable solutions and the methods to make them.
Jiang discloses in paragraph 0004, a method for preparing an adjusted precursor solution for a radiation patternable coating comprising a mixture of an organic solvent and a first monoalkyl tin trialkoxide (RSn(OR′)3) having a tin concentration that is from about 0.004 M to about 1.0 M.
Jiang discloses in paragraph 0016, the alkyl tin trialkoxide compositions can be represented by the formula RSn(OR′)3, where R and R′ are independently hydrocarbyl groups, such as an alkyl or a cycloalkyl with 1-31 carbon atoms with one or more carbon atoms optionally substituted with one of more heteroatom functional groups containing O, N, Si, Ge, Sn, Te, and/or halogen atoms or an alkyl or a cycloalkyl further functionalized with a phenyl or cyano group. In some embodiments, R′ can comprise ≤10 carbon atoms and can be, for example, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, or t-amyl. The R group can be a linear, branched, (i.e., secondary or tertiary at the metal-bonded carbon atom), or cyclic hydrocarbyl group. Each R group individually and generally has from 1 to 31 carbon atoms with 3 to 31 carbon atoms for the group with a secondary-bonded carbon atom and 4 to 31 carbon atoms for the group with a tertiary-bonded carbon atom. In particular, branched alkyl ligands can be desirable for some patterning compositions where the compound can be represented as R1R2R3CSn(OR′)3, where R1 and R2 are independently an alkyl group with 1-10 carbon atoms, and R3 is hydrogen or an alkyl group with 1-10 carbon atoms. In some embodiments R1 and R2 can form a cyclic alkyl moiety, and R3 may also join the other groups in a cyclic moiety. Suitable branched alkyl ligands can be, for example, isopropyl (R1 and R2 are methyl and R3 is hydrogen), tert-butyl (R1, R2 and R3 are methyl), tert-amyl (R1 and R2 are methyl and R3 is —CH2CH3), sec-butyl (R1 is methyl, R2 is —CH2CH3, and R3 is hydrogen), neopentyl (R1 and R2 are hydrogen, and R3 is —C(CH3)3), cyclohexyl, cyclopentyl, cyclobutyl, and cyclopropyl. Examples of suitable cyclic groups include, for example, 1-adamantyl (—C(CH2)3(CH)3(CH2)3 or tricyclo(3.3.1.13,7) decane bonded to the metal at a tertiary carbon) and 2-adamantyl (—CH(CH)2(CH2)4(CH)2(CH2) or tricyclo(3.3.1.13,7) decane bonded to the metal at a secondary carbon). In other embodiments hydrocarbyl groups may include aryl or alkenyl groups, for example, benzyl or allyl, or alkynyl groups. In other embodiments the hydrocarbyl ligand R may include any group consisting solely of C and H and containing 1-31 carbon atoms. In summary, some examples of suitable alkyl groups bonded to tin include, for example, linear or branched alkyl (i-Pr ((CH3)2CH—), t-Bu ((CH3)3C—), Me (CH3—), n-Bu (CH3CH2CH2CH2—)), cyclo-alkyl (cyclo-propyl, cyclo-butyl, cyclo-pentyl), olefinic (alkenyl, aryl, allylic), or alkynyl groups, or combinations thereof. In further embodiments suitable R groups may include hydrocarbyl groups substituted with hetero-atom functional groups including cyano, thio, silyl, ether, keto, ester, or halogenated groups or combinations thereof.
Jiang further discloses in paragraph 0020, as presented in the Examples, the compositions described herein have been found to be stable for well over 6 weeks, which suggests significantly longer-term stability. Some compositions have been stable for over 8 months. These particularly stable compositions are based on monoalkyl tin tri(O-t-amyl) compounds. The alkoxy ligand O-t-amyl represents O—CCH3CH3CH2CH3. While other alkoxides can be used to practice the current invention, the monoalkyl tin t-amyl alkoxide compounds have been found to possess desirable properties with respect to preparation, purification, and subsequent manipulation and handling. Solutions with blends of compounds having different alkoxy ligands can also be used. Selection of appropriate alkoxy ligands may also be solvent dependent, though it would be expected that other alkoxy ligands should be able to yield at least comparable results
Jiang does not disclose a tin tetraalkoxide compound having the claimed formula (2). Therefore, Jiang has met the limitation of the present invention of having less than about 5 mol% of a tin tetraalkoxide compound having the claimed formula (2) (less than 5 mol% encompasses zero).
Jiang does not disclose a diorgano tin dialkoxide having the claimed formula (3). Therefore, Jiang has met the limitation of the present invention of having less than about 1 mol% of a diorgano tin dialkoxide having the claimed formula (3) (less than 1 mol% encompasses zero).
The claimed invention is anticipated by the reference because the reference teaches a composition which comprises all of the claimed components. In the alternative, no patentable distinction is seen to exist between the reference and the claimed invention absent evidence to the contrary.
In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Regarding Claims 5-15
Jiang discloses in paragraph 0004, a method for preparing an adjusted precursor solution for a radiation patternable coating comprising a mixture of an organic solvent and a first monoalkyl tin trialkoxide (RSn(OR′)3) having a tin concentration that is from about 0.004 M to about 1.0 M.
Jiang discloses in paragraph 0016, the alkyl tin trialkoxide compositions can be represented by the formula RSn(OR′)3, where R and R′ are independently hydrocarbyl groups, such as an alkyl or a cycloalkyl with 1-31 carbon atoms with one or more carbon atoms optionally substituted with one of more heteroatom functional groups containing O, N, Si, Ge, Sn, Te, and/or halogen atoms or an alkyl or a cycloalkyl further functionalized with a phenyl or cyano group. In some embodiments, R′ can comprise ≤10 carbon atoms and can be, for example, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, or t-amyl. The R group can be a linear, branched, (i.e., secondary or tertiary at the metal-bonded carbon atom), or cyclic hydrocarbyl group. Each R group individually and generally has from 1 to 31 carbon atoms with 3 to 31 carbon atoms for the group with a secondary-bonded carbon atom and 4 to 31 carbon atoms for the group with a tertiary-bonded carbon atom. In particular, branched alkyl ligands can be desirable for some patterning compositions where the compound can be represented as R1R2R3CSn(OR′)3, where R1 and R2 are independently an alkyl group with 1-10 carbon atoms, and R3 is hydrogen or an alkyl group with 1-10 carbon atoms. In some embodiments R1 and R2 can form a cyclic alkyl moiety, and R3 may also join the other groups in a cyclic moiety. Suitable branched alkyl ligands can be, for example, isopropyl (R1 and R2 are methyl and R3 is hydrogen), tert-butyl (R1, R2 and R3 are methyl), tert-amyl (R1 and R2 are methyl and R3 is —CH2CH3), sec-butyl (R1 is methyl, R2 is —CH2CH3, and R3 is hydrogen), neopentyl (R1 and R2 are hydrogen, and R3 is —C(CH3)3), cyclohexyl, cyclopentyl, cyclobutyl, and cyclopropyl. Examples of suitable cyclic groups include, for example, 1-adamantyl (—C(CH2)3(CH)3(CH2)3 or tricyclo(3.3.1.13,7) decane bonded to the metal at a tertiary carbon) and 2-adamantyl (—CH(CH)2(CH2)4(CH)2(CH2) or tricyclo(3.3.1.13,7) decane bonded to the metal at a secondary carbon). In other embodiments hydrocarbyl groups may include aryl or alkenyl groups, for example, benzyl or allyl, or alkynyl groups. In other embodiments the hydrocarbyl ligand R may include any group consisting solely of C and H and containing 1-31 carbon atoms. In summary, some examples of suitable alkyl groups bonded to tin include, for example, linear or branched alkyl (i-Pr ((CH3)2CH—), t-Bu ((CH3)3C—), Me (CH3—), n-Bu (CH3CH2CH2CH2—)), cyclo-alkyl (cyclo-propyl, cyclo-butyl, cyclo-pentyl), olefinic (alkenyl, aryl, allylic), or alkynyl groups, or combinations thereof. In further embodiments suitable R groups may include hydrocarbyl groups substituted with hetero-atom functional groups including cyano, thio, silyl, ether, keto, ester, or halogenated groups or combinations thereof.
Jiang does not disclose a tin tetraalkoxide compound having the claimed formula (2). Therefore, Jiang has met the limitation of the present invention of having less than about 5 mol% of a tin tetraalkoxide compound having the claimed formula (2) (less than 5 mol% encompasses zero).
Jiang does not disclose a diorgano tin dialkoxide having the claimed formula (3). Therefore, Jiang has met the limitation of the present invention of having less than about 1 mol% of a diorgano tin dialkoxide having the claimed formula (3) (less than 1 mol% encompasses zero).
Jiang discloses in paragraph 0022, suitable solvents generally comprise alcohols that are liquids at room temperature. Generally, the solvents are at least 50 weight percent alcohols with any remaining organic solvent liquids being soluble in the alcohol, such as an alkane (such as pentane or hexane), an aromatic hydrocarbon (such as toluene), ether (such as diethyl ether, C2H5OC2H5), or mixtures thereof. In some embodiments, the solvent is at least 90 weight percent alcohol, and the solvent can be effectively alcohol with just trace impurities of other compounds. Suitable alcohols are generally monomeric alcohols with a melting point of no more than about 10° C., such as methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, branched versions thereof, and mixtures thereof. For alcohols with three or more carbon atoms, a large number of branched isomers are available. The examples are based on a branched hexanol, specifically 4-methyl-2-pentanol, which can also be referred to as methyl isobutyl carbinol. Similar results are expected with other alcohols, and the results are not believed to be particularly alcohol dependent, although the specific stabilization may have some quantitative dependence on the alcohol, which can be checked empirically based on the teachings herein.
Jiang discloses in paragraph 0029, a batch of stock solvent is obtained, and an aliquot of the batch is checked for water content. As a general matter, a selected concentration of water would be selected to exceed the range of water concentrations of the solvent grade being used so that adjustment of the water content can be adjusted through water addition. However, such a selected water content should be selected to also provide desired shelf life for the precursor solution, which depends on the composition of the monoalkyl tin trialkoxide. Generally, the amount of water selected can also depend on the concentration of tin in the precursor solution.
Jiang discloses in paragraph 0031, stability of the precursor solutions can be evaluated with respect to changes relative to the initial solution. Specifically, a solution, as evaluated in an unstirred resting solution, can be described herein to have lost stability if phase separation occurs with the production of large sol particles or if the solution visible particulates are formed. Based on the processing approaches described herein, the solutions can be stable for at least about 42 days without additional mixing, in further embodiments at least about three months, and in other embodiments at least about six months. A person of ordinary skill in the art will recognize that additional ranges of stabilization times are contemplated. Suitable solutions generally can be formulated with sufficient stabilization times that the solutions can be commercially distributed with appropriate shelf lives.
Jiang discloses in paragraph 0033, the adjusted solutions with the selected water content within a specified tolerance should then be stored in a sealed container or other circumstances to avoid exposure to ambient air that can alter the water content. With sufficient stabilization, the containers of monoalkyl tin trialkoxides can be distributed in the containers to locations for the performance of lithographic patterning.
Jiang discloses in paragraph 0034, the monoalkyl trialkoxide solutions are used to form a hydrated coating of monoalkyl tin ox hydroxo composition. The further hydrolysis to form this composition can be performed during deposition through exposure to atmospheric water of through the delivery of some water vapor or following deposition through the addition of a sufficient amount of water. The hydrolyzed coating can be subjected to a drying step that can involve heating of the coating. Radiation, electromagnetic or electron beam, generally can be directed to the dried coated substrate through a mask or a radiation beam can be controllably scanned across the substrate to form a latent image in the coating. Various additional processing steps, such as heating steps and development, can be performed to pattern the coating in either a positive tone or negative tone image. These organometallic patterning compositions provide especially promising properties for the advance of EUV patterning into the formation of finer patterning features.
The claimed invention is anticipated by the reference because the reference teaches a composition which comprises all of the claimed components. In the alternative, no patentable distinction is seen to exist between the reference and the claimed invention absent evidence to the contrary.
In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Regarding Claims 16-20
Jiang discloses in paragraph 0004, a method for preparing an adjusted precursor solution for a radiation patternable coating comprising a mixture of an organic solvent and a first monoalkyl tin trialkoxide (RSn(OR′)3) having a tin concentration that is from about 0.004 M to about 1.0 M.
Jiang discloses in paragraph 0016, the alkyl tin trialkoxide compositions can be represented by the formula RSn(OR′)3, where R and R′ are independently hydrocarbyl groups, such as an alkyl or a cycloalkyl with 1-31 carbon atoms with one or more carbon atoms optionally substituted with one of more heteroatom functional groups containing O, N, Si, Ge, Sn, Te, and/or halogen atoms or an alkyl or a cycloalkyl further functionalized with a phenyl or cyano group. In some embodiments, R′ can comprise ≤10 carbon atoms and can be, for example, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, or t-amyl. The R group can be a linear, branched, (i.e., secondary or tertiary at the metal-bonded carbon atom), or cyclic hydrocarbyl group. Each R group individually and generally has from 1 to 31 carbon atoms with 3 to 31 carbon atoms for the group with a secondary-bonded carbon atom and 4 to 31 carbon atoms for the group with a tertiary-bonded carbon atom. In particular, branched alkyl ligands can be desirable for some patterning compositions where the compound can be represented as R1R2R3CSn(OR′)3, where R1 and R2 are independently an alkyl group with 1-10 carbon atoms, and R3 is hydrogen or an alkyl group with 1-10 carbon atoms. In some embodiments R1 and R2 can form a cyclic alkyl moiety, and R3 may also join the other groups in a cyclic moiety. Suitable branched alkyl ligands can be, for example, isopropyl (R1 and R2 are methyl and R3 is hydrogen), tert-butyl (R1, R2 and R3 are methyl), tert-amyl (R1 and R2 are methyl and R3 is —CH2CH3), sec-butyl (R1 is methyl, R2 is —CH2CH3, and R3 is hydrogen), neopentyl (R1 and R2 are hydrogen, and R3 is —C(CH3)3), cyclohexyl, cyclopentyl, cyclobutyl, and cyclopropyl. Examples of suitable cyclic groups include, for example, 1-adamantyl (—C(CH2)3(CH)3(CH2)3 or tricyclo(3.3.1.13,7) decane bonded to the metal at a tertiary carbon) and 2-adamantyl (—CH(CH)2(CH2)4(CH)2(CH2) or tricyclo(3.3.1.13,7) decane bonded to the metal at a secondary carbon). In other embodiments hydrocarbyl groups may include aryl or alkenyl groups, for example, benzyl or allyl, or alkynyl groups. In other embodiments the hydrocarbyl ligand R may include any group consisting solely of C and H and containing 1-31 carbon atoms. In summary, some examples of suitable alkyl groups bonded to tin include, for example, linear or branched alkyl (i-Pr ((CH3)2CH—), t-Bu ((CH3)3C—), Me (CH3—), n-Bu (CH3CH2CH2CH2—)), cyclo-alkyl (cyclo-propyl, cyclo-butyl, cyclo-pentyl), olefinic (alkenyl, aryl, allylic), or alkynyl groups, or combinations thereof. In further embodiments suitable R groups may include hydrocarbyl groups substituted with hetero-atom functional groups including cyano, thio, silyl, ether, keto, ester, or halogenated groups or combinations thereof.
Jiang further discloses in paragraph 0020, as presented in the Examples, the compositions described herein have been found to be stable for well over 6 weeks, which suggests significantly longer-term stability. Some compositions have been stable for over 8 months. These particularly stable compositions are based on monoalkyl tin tri(O-t-amyl) compounds. The alkoxy ligand O-t-amyl represents O—CCH3CH3CH2CH3. While other alkoxides can be used to practice the current invention, the monoalkyl tin t-amyl alkoxide compounds have been found to possess desirable properties with respect to preparation, purification, and subsequent manipulation and handling. Solutions with blends of compounds having different alkoxy ligands can also be used. Selection of appropriate alkoxy ligands may also be solvent dependent, though it would be expected that other alkoxy ligands should be able to yield at least comparable results
Jiang does not disclose a tin tetraalkoxide compound having the claimed formula (2). Therefore, Jiang has met the limitation of the present invention of having less than about 5 mol% of a tin tetraalkoxide compound having the claimed formula (2) (less than 5 mol% encompasses zero).
Jiang does not disclose a diorgano tin dialkoxide having di(2-methylpropenyl)tin dialkoxide. Therefore, Jiang has met the limitation of the present invention of having less than about 1 mol% of di(2-methylpropenyl)tin dialkoxide having the claimed formula (3) (less than 1 mol% encompasses zero).
The claimed invention is anticipated by the reference because the reference teaches a composition which comprises all of the claimed components. In the alternative, no patentable distinction is seen to exist between the reference and the claimed invention absent evidence to the contrary.
In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Jilek et al. (US 2022/0411446) discloses in the abstract, organotin compounds are presented that are represented by the formula RSnL3, wherein R is a deuterated hydrocarbyl group and L is a hydrolysable ligand. Two different synthesis techniques are described for synthesizing these compositions. A first method involves reacting a primary halide hydrocarbyl compound (R—X, where X is a halide atom) with an organometallic composition comprising SnL3 moieties associated with metal cations M, where M is an alkali metal, alkaline earth metal, and/or pseudo-alkaline earth metal (Zn, Cd, or Hg), and L is either an amide ligand resulting in an alkali metal tin triamide compound or an acetylide ligand resulting in an alkali metal tin triacetylide, to form correspondingly a monohydrocarbyl tin triamide (RSn(NR′2)3) or a monohydrocarbyl tin triacetylide (RSn(C≡CRs)3). An alternative approach involves reacting a Grignard reagent RMgX with SnL4 in a solution comprising an organic solvent to form a monoorgano tin tralkylamide, a monoorgano tin trialkoxide, monoorgano tin tri acetylide or monoorgano tin tricarboxylate. The compositions are useful for radiation patterning, especially with EUV radiation.
Edson et al. (US 2019/0315782) discloses in the abstract, a pure composition comprises a monoalkyltin trialkoxide compound represented by the chemical formula RSn(OR')3 or a monoalkyl tin triamide compound represented by the chemical formula RSn(NR'2)3 and no more than 4 mole% dialkyltin compounds relative to the total tin amount, where R is a hydrocarbyl group with 1-31 carbon atoms, and wherein R' is a hydrocarbyl group with 1-10 carbon atoms. Methods are described for the formation of the pure compositions. A solid composition comprises a monoalkyl triamido tin compound represented by the chemical formula RSn-(NR'COR")3, where R is a hydrocarbyl group with 1-31 carbon atoms, and where R' and R" are independently a hydrocarbyl group with 1-10 carbon atoms. The compositions are suitable for the formation of resist compositions suitable for EUV patterning in which the compositions have a high EUV absorption.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LATOSHA D HINES whose telephone number is (571)270-5551. The examiner can normally be reached Monday thru Friday 9:00 AM - 6:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem Singh can be reached at 571-272-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Latosha Hines/Primary Examiner, Art Unit 1771
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