Detailed Action
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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 08/26/2024 and 01/13/2026 are being considered by the examiner.
Response to Amendment
Applicant’s Amendment to the claims filed 06/11/2026 has been considered and is entered.
Response to Arguments
Applicant’s amendments and arguments made in their Response overcome the Objection set forth in the prior office action.
Regarding the arguments made, the Examiner does not consider the arguments made regarding the -O-RALU functionality of the instant claims persuasive. The claim states that “RALU represents any one of a tertiary ether, tertiary carbonate, or acetal formed together with the adjacent oxygen atom” (examiner’s emphasis where bolded). As written, it seems clear that the R group in question does not represent any of the functional groups by itself, and there is only one “(the) adjacent oxygen atom” depicted in the claim. That is to say – the groups recited are made from the combination of the RALU group and the -O- linkage to the aromatic ring – the resultant ether/carbonate/acetal has the structure Ar-O- RALU where Ar is the aromatic ring depicted and RALU is as defined in the claim.
Hatakeyama defines an anion having an aromatic ring structure having a straight/branched alkoxy group thereon, wherein the alkoxy group may bear a tertiary alkyl group as was set forth in the prior office action – this Ar-O-R1 structure defines an ether. If the claimed ether group formed with RALU does not use the adjacent oxygen atom depicted in the claim, then it requires an unrecited and not-depicted “the” adjacent oxygen atom.
Regarding the structural limitation of I and O- RALU being on adjacent carbons - while this limitation is met by the reference furnished in the prior office action, a new grounds of rejection is being made so as to make the examiner’s position more explicit for clarity of the record. This action is thus non-final.
Claim Rejections - 35 USC § 103
Claim(s) 1-17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 20170351177 A1).
Regarding Claim 1 and 3-5, Hatakeyama discloses a chemically amplified resist composition comprising a sulfonium salt of an iodized benzoic acid as a quencher, where the quencher imparts improved LWR and high contrast to the composition and processed articles made therefrom.
Hatakeyama does not explicitly disclose an experimental example meeting the sum total of the limitations of the claims.
These limitations are met by the general disclosure of the reference.
The quencher (claim 4) of the reference is generally described by the formula (A) in [0021] and [0054].
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Where R1 is a hydroxyl group, C1-C6 straight/branched/cyclic alkoxy or alkyl group, C2-C6 straight/branched/cyclic acyloxy group, or other group described in the cited paragraph. X is a linking group or single bond.
R2-R4 are each independently a halogen, or a C1-C12 straight/branched/cyclic alkyl group or C6-C20 aryl or C7-C12 aralkyl group or C7-C12 aryloxyalkyl group in which at least one hydrogen or more may be substituted for a hydroxy halogen, or other group described in [054]
The formula meets the limitations of the claims for where:
Claimed Z+ is a sulfonium cation (claim 3) as per claimed cation-1 and R11’ to R13’ are each a hydrocarbon group having 1-20 carbon atoms (C1-12 alkyl or C6-C20 alkyl, or other group mentioned above)
The instant X is a single bond
The instant n1 is 0
The instant n3 is 1
R1n refers to an alkoxy group having a C4-C6 branched alkyl attachment thereon
Branched C4 groups comprise a small genus having 3 members – a person having ordinary skill in the art would immediately envision a t-Bu group from the genus of “branched C4 group”. Branched C5 groups similarly comprise a small number of species, of which one is a tertiary alkyl group. Branched C6 groups comprise a small number of species, of which two are tertiary alkyl groups. The reference explicitly depicts and names tBu structures elsewhere such as in cations at page 6 and anions at page 21.
The combination of the aryl ring, the oxygen linkage of the alkoxy group, and the alkyl group of the alkoxy group defines an ether.
R1 and I are not stereochemically locked – they may be on variable positions on the disclosed aryl group of the reference. There are only 5 positions on the aryl ring of the reference that can be substituted – when R1 and I are both present the number of substitution patterns where the R1 and I atoms are ortho to each other is sufficiently small that a person having ordinary skill in the art would be able to readily envision them. These chemical embodiments are substantially similar to one another (differing only by stereochemical arrangement) and would be expected to behave similarly to each other.
The sulfonium salt of the reference, when included in a photoresist composition, is asserted by the reference to improve the contrast and resolution as well as reduce the LWR of the composition ([0020]).
A person having ordinary skill would have found it obvious arrive at the claimed invention prior to the effective filing date in view of the disclosure of the reference by using the taught sulfonium salt of Hatakeyama to arrive at a photoresist displaying improved contrast and resolution.
Regarding Claim 2, the reference Hatakeyama meets the limitations of the claims as discussed above regarding claim 1. The reference does not provide a specific experimental example meeting the claim limitations as set forth.
However, these limitations are met by the general disclosure of the reference.
The reference discusses the quencher as covered above regarding claim 1. In particular examples, the reference discloses ester and alkoxy functionalities upon the phenyl group of the quencher’s anion (R1). For examples, see pages 21 and 22. These groups function as acid-labile moieties that interact with excess acid beyond the function of the carboxylate group in the quencher.
Elsewhere, the reference discloses acid labile groups, when discussing the base polymer and the inclusion of groups on monomers bearing-acid labile moieties. At [0066], AL-1 through AL-3 are discussed:
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Where AL-1 and AL-2:
R13 and R16 are each independently a monovalent hydrocarbon group having 1-40 carbon atoms that may be, for example a straight/branched/cyclic alkyl and be substituted with a heteroatom such as O, S, N, or F.
R14 and R15 are each independently H or a C1-C20 monovalent hydrocarbon group, for example a straight/branched/cyclic alkyl and be substituted with a heteroatom such as O, S, N, or F.
Subscript A1 is 0-10
The formula groups above, applied to the -R1n group where R1 is an alkoxy group as discussed above regarding claim 1, meets the limitations of the claim where:
ALU-1
Subscript t is 1
R21-R23’ are each a C1-C6 hydrocarbyl group and may be bonded to form a ring
The reference comprises a C4-C36 hydrocarbyl group that is branched or cyclic, and the R1 of the sulfonium salt may be alkyl group that is further substituted with an ester group having a C1-C6 straight or branched alkyl group
ALU-2
R24 and R25’ are each independently H or a C1-C10 monovalent hydrocarbon group, for example a straight/branched/cyclic alkyl and be substituted with a heteroatom such as O or S, and may be bonded to form a C2-C20 hydrocarbyl group that may be substituted.
R26 is a monovalent hydrocarbon group having 1-40 carbon atoms that may be, for example a straight/branched/cyclic alkyl and be substituted with a heteroatom such as O, S
Xa is O.
At [0049], the reference asserts that LWR improved by reducing agglomeration of the polymer and/or acid generator, and this is most effectively done by reducing the differences between hydrophobic and hydrophilic properties of the polymer and the acid generator. Incorporating acid-labile groups from the polymer sidechains taught by the reference into the quencher would reduce the hydrophobicity and hydrophilicity difference between the two components and improve LWR
A person having ordinary skill in the art would find it obvious to arrive at the claimed invention by modifying the chemical functionality of the R1n alkoxy embodiment to correspond to an acid labile group in order to further improve the acid-diffusion control capabilities of the quencher compound and improve the LWR of the composition.
Regarding Claim 6-9, 11-13, and 15-17, the reference Hatakeyama meets the limitations of the claims as discussed above regarding claim 1. The reference does not provide a specific experimental example meeting the claim limitations as set forth.
However, these limitations are met by the general disclosure of the reference.
The chemically amplified photoresist composition of Hatakeyama comprises the quencher salt as described above regarding claims 1 and 3-5, and further comprises an acid generator as described from [0091]-[0115] (claim 6), where the salt cation conforms to the general formula (1) and salt anions may be one of (1A)-(1D), where (1A) is a sulfonic acid anion, (1B) is a sulfonyl imide acid anion, and (1C) is a sulfonyl methide acid anion – exposure to induce acid generation would necessarily generate the corresponding acid (claim 7).
The composition comprises an organic solvent as described from [0119]-[0120] (claim 8).
The composition comprises a base polymer, described from [0061]-[0090] (claim 9)
The composition may be a negative or positive-type chemically amplified composition, where the base polymer’s composition changes to best suit the negative/positive processing as described at [0084]-[0089] (claims 11 and 12). When the base polymer is present in a negative resist composition, an acid-labile group is not essential and may be excluded, as per [0084] (claim 13).
The resist composition comprises a surfactant, as per [0117]-[0121] (claim 15).
The composition is treated as per a patterning process described from [0143]-[0141], where the resist composition is deposited upon a substrate, baked to remove solvent, exposed to radiation, post-exposure baked, and developed (claim 16). Exposures may be performed with a radiation source such as from a UV source, deep-UV, EUV, electron beam, z-ray, soft-x-ray, or KrF or ArF excimer laser light as described in [0136] and at [0030] (claim 17).
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the time of filing, incorporating the quencher and the various components disclosed by the reference to arrive at a chemically amplified positive or negative resist having improved LWR and contrast imparted by the chemical components present therein.
Regarding Claim 10, Hatakeyama discloses the limitations of the claim as discussed above regarding claim 1 above. Hatakeyama however does not disclose the limitations of the instant claim in a particular experimental embodiment.
These limitations are met by the general disclosure of the reference.
The composition of Hatakeyama comprises a base polymer, described from [0061]-[0090].
Two particular subunits are (a1) and (a2):
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Where:
RA is H or Me
Y1 is a single bond, phenylene group, naphthalene group, ester group, or C1-C12 group that may have a lactone ring
Y2 is a single bond or ester bond
R11 and R12 are each an acid labile group.
Both (a1) and (a2) may be present or each may be present singly.
Exemplary units meeting the limitations of the above claims are depicted at [0064]-[0068].
The above formulas meet the limitations of the instant claims where:
RA is H or Me
Y1 is a single bond, phenylene group, naphthalene group, ester group, or C1-C12 group that may have a lactone ring
Y2 is a single bond
R14 is a C1 alkanediyl group having an ester group substituted therein
Y3 is a single bond
Subscript b is 0
Subscript a is 1
R11 and R12 are each an acid labile group
Acid labile groups are described from [0065]-[0068]
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the time of filing, incorporating the quencher, monomer subunits of the base polymer, and the other components disclosed by the reference to arrive at a chemically amplified positive or negative resist having improved LWR and contrast imparted by the chemical components present therein.
Regarding Claim 14, Hatakeyama discloses the limitations of the claim as discussed above regarding claim 1 above. Hatakeyama however does not disclose the limitations of the instant claim in a particular experimental embodiment.
These limitations are met by the general disclosure of the reference.
The composition of Hatakeyama comprises a base polymer, described from [0061]-[0090].
In a preferred embodiment, at least one of recurring units (f1)-(f3) are present in the base polymer, where multiple instances of the units may also be present ([0075]-[0083]):
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RA is H or Me
R21 is a single bond, phenylene group or -O-R31 or -C(=O)-Q1-R31 where Q1 is -O- or -NH-
R31 is a C1-C6 straight/branched/cyclic alkylene group or C2-C6 alkenylene group or phenylene group which may be substituted with carbonyl, ester, ether, or hydroxyl
R23-R29 are each independently a C1-C12 straight/cyclic/branched alkyl group which may be substituted with carbonyl, ester, or ether, or a C6-C20 aryl group
Z1 is a single bond or other group described in [0076] such as a carboxylic ester having a Z11 attachment group where Z11 is a C1-C12 alkyl group that may be substituted.
A is a H or CF3
Z2 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, or other group such as -O-R32
The above subunits meet the limitations of the claim for where:
Claimed (f1) corresponds to the reference’s (f1)
RA is H or Me
Z1 corresponds to reference R21 at single bond, phenylene, or the R31-bearing ether, ester, and/or amide group
R21 and R22 correspond to R23 and R22 in the reference
M- is a nonnucleophilic anion
Claimed (f2) corresponds to the reference’s (f2) where:
Z2 is an ester bond
Z3 is a single bond
Z4 is a 2,2,2-trifluoro-1,1-ethanedyl group (reference A is a CF3)
R23-R25 correspond to R24-R26
Claimed (f3) corresponds to the reference’s (f3) where:
Z5 corresponds to reference’s Z2
R26-R28 corresponds to R27-R29
Exemplary compounds are disclosed in the structures of [0077] and [0078].
The inclusion of these subunits in the polymer is effective in restraining acid diffusion and improving edge roughness.
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the filing date by incorporating one or more of the subunits f1-f3 into the base polymer so as to restrain acid diffusion and improve edge roughness in a finished patterned product.
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.
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/A.P.T./Examiner, Art Unit 1737
/John S. Chu/Primary Examiner, Art Unit 1737
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