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 cancellation of claim 9 and addition of claims 16-17 is acknowledged.
Applicant's arguments filed 9 January 2026 have been fully considered but they are not persuasive.
Applicant has incorporated the limitations previously presented as claim 9 into independent claim 1. Claim 1 now recites the extinction coefficient of a film formed from the resist composition with respect to inspection light of wavelength 300 to 400 nm. Applicant argues that the previously cited prior art (Kotake and LaBeaume) fails to render obvious instant claim 1, as amended. Specifically, Applicant argues that the combination of Kotake and LaBeaume fails to render obvious the extinction coefficient recited by instant claim 1. Applicant argues that LaBeaume is silent about controlling the extinction coefficient (“k value”) of the resist composition and therefore, there would have been no motivation to replace the quencher of Kotake with the quencher of LaBeaume in order to obtain a resist composition capable of forming a film having a k value of up to 0.01. Applicant further argues that the resist composition taught by Kotake cannot form resist films having a k value of up to 0.01, citing comparative examples CR-2 to CR-4 as evidence. Comparative examples CR-2 to CR-4 are identical to each other except for the content of the onium salt compound used. For comparison, examples R-32 and R-33 of the instant application are identical to comparative examples CR-2 and CR-3, respectively, except that examples R-32 and R-33 utilize a different onium salt (inventive examples use Q-C, comparative examples use Q-D). The principal difference between onium salts Q-C and Q-D is that Q-C is a compound according to General Formula (A1) and Q-D is not. Referring to Table 8 of the instant application’s specification, it is apparent that the onium salt utilized strongly influences the k value in the claimed wavelength (compare resist compositions R-32 and R-33 with CR-2 and CR-3, respectively). Furthermore, the instant application states that onium salts having formula (A1) show k values up to 0.01 at any wavelength and up to 0.003 at wavelengths 400 nm, 355 nm, and 330 nm (see paragraph 0313 of the instant application’s specification). The instant application’s specification further suggests that onium salts having formula (A1) have desirable optical properties in the wavelength region of 300 to 400 nm (see paragraph 0114-0115 of the instant application’s specification). As the onium salt taught by LaBeaume satisfies formula (A1), and specifically includes a cation and anion taught by the instant application’s specification to be suitable, it stands to reason, based upon the Applicant’s own admissions, that a resist film formed of the composition obtained by replacing the onium salt taught by Kotake with the onium salt taught by LaBeaume satisfies the extinction coefficient value within the wavelength range recited by instant claim 1, as amended, as well as the extinction coefficient values recited by instant claims 16 and 17. Therefore, Applicant’s arguments are not found to be persuasive and the previous rejection is not withdrawn.
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) 1-8 and 10-17 are rejected under 35 U.S.C. 103 as being unpatentable over US 2018/0180992 A1 (hereby referred to as Kotake) in view of US 2015/0346599 A1 (hereby referred to as LeBeaume).
Regarding Claims 1-2 and 16-17, Kotake discloses a chemically amplified positive resist composition and a resist pattern forming process. The positive tone resist composition comprises a sulfonium compound and a base polymer adapted to be decomposed under the action of acid to increase its solubility in alkaline developer (Kotake, paragraph 0052). The sulfonium compound functions as a strong acid diffusion inhibitor, also referred to as an onium salt type quencher (Kotake, paragraph 0061-0062). The base polymer comprises repeat units having the formula (B1), which is reproduced below (Kotake, paragraph 0068).
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In formula (B1), RA is hydrogen, fluorine, methyl, or trifluoromethyl; R11 is each independently halogen, an optionally halogenated C2-C8 straight, branched or cyclic acyloxy group, optionally halogenated C1-C6 straight, branched or cyclic alkyl group, or optionally halogenated C1-C6 straight, branched or cyclic alkoxy group; A1 is a single bond or a C1-C10 straight, branced, or cyclic alkylene group in which an ether bond may intervene in a carbon-carbon bond; v is 0 or 1; w is an integer of 0 to 2; a is an integer in the range of 0 ≤ a ≤ 5+2w-b; and b is an integer of 1 to 3 (Kotake, paragraph 0069). It is apparent that formula (B1) of Kotake matches formula (B1) as recited by instant claim 1. Kotake discloses that the resist composition may further comprise a photoacid generator (PAG) in order that the composition function as a chemically amplified positive resist composition (Kotake, paragraph 0122). In particular, Kotake provides an inventive example (Example 1, see Table 1 on page 38 of Kotake) wherein the polymer (A1) is provided in an amount of 80 parts by weight, the onium compound (Q-1) is provided in an amount of 3 parts by weight, and the photoacid generator (PAG-A) is provided in an amount of 9 parts by weight. Thus, ratio of the amount of the photoacid generator with respect to the amount of the onium compound is less than 4 (
9
p
a
r
t
s
3
p
a
r
t
s
=
3
), the amount of photoacid generator is at least 5 parts by weight per 80 parts by weight of the polymer, and the total amount of the onium compound and the photoacid generator is at least 10 parts by weight per 80 parts by weight of the polymer (
3
p
a
r
t
s
+
9
p
a
r
t
s
=
12
p
a
r
t
s
). The structure of Polymer A1 is provided below (see paragraph 0162 and page 35 of Kotake).
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The repeating unit of Polymer A1 having the subscript “a” corresponds to the repeating unit represented by formula (B1) recited by instant claim 1, wherein RA is hydrogen, a1 is 0, A1 is a single bond, a2 is 0, a3 is 0, and a4 is 1. This repeating unit constitutes 76 mol% of the polymer, thus satisfying by itself the limitation of instant claim 1 that the repeat units of aromatic ring structure is at least 65 mol% of the overall repeat units of the polymer. The additional repeating units increase the content of repeat units having an aromatic ring structure to 100 mol%.
However, Kotake is silent in regards to the onium compound having the formula of (A1), as recited by instant claim 1. LaBeaume teaches a photo-destroyable quencher and a photoresist composition comprising the same. The photo-destroyable quencher has the following structure:
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wherein X is iodine or sulfur; n is 2 when X is iodine and 3 when X is sulfur, each R1 is independently unsubstituted or substituted C1-40 hydrocarbyl, or two occurrences of R1 optionally are bonded to each other to form a ring; and each of R2 to R6 is independently hydrogen, unsubstituted or substituted C1-18 hydrocarbyl, halogen, nitro, C1-12 fluorinated alkyl, cyano, aldehyde (—C(O)H), C2-20 ester (—C(O)OR7, wherein R7 is C1-19 hydrocarbyl), C2-20 ketone (—C(O)R7, wherein R7 is C1-19 hydrocarbyl), C1-20 sulfonyl hydrocarbyl (—S(O)2R8, wherein R8 is C1-20 hydrocarbyl), or sulfonamide (—S(O)2NR9 2, wherein each occurrence of R9 is independently hydrogen or C1-20 hydrocarbyl); provided that at least one of R2, R3, R4, R5, and R6 is halogen, nitro, C1-12 fluorinated alkyl, cyano, aldehyde (—C(O)H), C2-20 ester (—C(O)OR7, wherein R7 is C1-19 hydrocarbyl), C2-20 ketone (—C(O)R7, wherein R7 is C1-19 hydrocarbyl), C1-20 sulfoxyl hydrocarbyl (—S(O)R8, wherein R8 is C1-20 hydrocarbyl), C1-20 sulfonyl hydrocarbyl (—S(O)2R9, wherein R9 is C1-20 hydrocarbyl), or sulfonamide (—S(O)2NR10 2, wherein each occurrence of R10 is independently hydrogen or C1-20 hydrocarbyl); and/or any one or more pairs of adjacent occurrences of R2, R3, R4, R5, and R6 are bonded to each other to form an unsubstituted or substituted ring (LeBeaume, paragraph 0019, see page 2). This structure is equivalent to the onium salt compound having the formula (A1), as recited by instant claim 1. In a specific embodiment, the photo-destroyable quencher has the structure reproduced below (LeBeaume, paragraph 0028, see page 7).
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The structure above is a specific embodiment of the onium salt compound having the formula (A1) recited by instant claim 1, wherein R1 to R5 is each a fluorine atom; Q+ is a sulfonium cation having the formula (A2); R11 to R13 is each a phenyl ring; and R11 and R12 are bonded together to form a ring with the sulfur atom to which they are attached. The sulfonium cation taught by LeBeaume is disclosed by the instant application as a suitable sulfonium cation (see page 15 of the instant application’s specification) and the anion taught by LeBeaume is disclosed by the instant application as a suitable anion (see page 13 of the instant application’s specification). The Examiner notes that the onium salt compound taught by LeBeaume further satisfies instant claim 2, as at least one of R1 to R5 is a group containing fluorine. The photoresist composition taught by LeBeaume comprises an acid-sensitive polymer, a photoacid generator, and the photo-destroyable quencher (LeBeaume, paragraph 0029). The photoresist composition may be a positive-tone type photoresist composition (LeBeaume, paragraph 0043 and 0058).
Kotake and LeBeaume are analogous art because both references pertain to photoresist compositions comprising quenchers, photoacid generators, and polymers. It would have been obvious to one having ordinary skill in the art before the filing date of the instant application to use the onium salt photo-destroyable quencher taught by LeBeaume in place of the onium salt compound in the positive-type photoresist composition disclosed by Kotake because the onium salt photo-destroyable quencher taught by LeBeaume provides increased solution stability, decreased water absorption, and increased lithographic critical dimension (CD) uniformity when provided in a photoresist composition (LeBeaume, paragraph 0018). The Examiner notes that Kotake and LeBeaume are both silent in regards to an extinction coefficient. However, the composition obtained by combining the teachings of Kotake and LeBeaume includes each of the chemical species of the positive resist composition according to instant claim 1. Furthermore, the composition obtained by combining the teachings of Kotake and LeBeaume comprises Polymer A1 (80 parts by weight), photoacid generator PAG-A (9 parts by weight), and the onium compound taught by LeBeaume reproduced below (3 parts by weight) (refer to Example 1 of Kotake, as shown in Table 1 on Page 38).
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The Examiner notes that Polymer A1 is identical to Polymer A-1 of the instant application (compare the structure on page 35 of Kotake with the structure shown on page 55 of the instant application’s specification) and PAG-A of Kotake is identical to PAG-A of the instant application (compare the structure on page 37 of Kotake with the structure shown on page 57 of the instant application’s specification). The compositions shown in the instant application’s inventive examples (see Table 1 on page 57 of the instant application’s specification) comprise the same polymer in the same amount and the same photoacid generator in a very similar amount. The difference between the inventive examples of the instant application and the composition obtained by combining Kotake and LeBeaume is that the inventive examples of the instant application do not utilize the onium salt compound depicted above. However, the onium salt compound depicted above is indicated by the instant application as a suitable onium salt compound for the photoresist composition (the sulfonium cation taught by LeBeaume is shown on page 15 of the instant application’s specification and the anion taught by LeBeaume is shown on page 13 of the instant application’s specification). Thus, whilst not explicitly stated by either Kotake or LeBeaume, one having ordinary skill in the art would expect that the composition obtained by combining the teachings of Kotake and LeBeaume, as described above, forms a resist film having an extinction coefficient of up to 0.01 (and, per the instant application’s specification paragraphs 0114-0118 and Tables 2 and 8, likely below 0.005 as well) relative to inspection light of wavelength 300 to 400 nm due to the composition obtained by combining Kotake and LeBeaume having similar or identical components in similar or identical amounts as the instant application’s composition. When the above proposed substitution is made, a chemically amplified positive resist composition according to instant claims 1-2 and 16-17 is obtained.
Regarding Claim 3, Kotake discloses that when the repeating units (B1) are free of a linker (that is, when v is 0 and A1 is a single bond in Kotake’s formula (B1), which is equivalent of a1 being 0 and A1 being a single bond in the instant application’s formula (B1)), the repeating units include one or more repeating units derived from 3-hydroxystyrene, 4-hydroxystyrene, 5-hydroxy-2-vinylnaphthalene, and 6-hydroxy-2-vinylnaphthalene (Kotake, paragraph 0070). Notable, 3-hydroxystyrene and 4-hydroxystyrene, when polymerized, yield repeating units equivalent to formula (B1-1) as recited by instant claim 1, for the case that a4 is equal to 1 and RA is hydrogen. Particularly, Polymer A1, whose structure is provided above, utilizes a repeating unit derived from 4-hydroxystyrene. Thus, Kotake discloses a repeating unit having the formula (B1-1).
Regarding Claim 4, Kotake discloses that the base polymer should preferably further comprise units having an acidic functional group protected with an acid labile group in order for the resist composition serve as a positive resist composition wherein the exposed region of a resist film is dissolved in alkaline aqueous solution (Kotake, paragraph 0073). For the recurring units which are protected with an acid labile group, repeating units having the formula (B2) (reproduced below) are most preferred (Kotake, paragraph 0074).
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In Formula (B2), RA is as defined for Formula (B1), R12 is each independently halogen, an optionally halogenated C2-C8 straight, branched or cyclic acyloxy group, optionally halogenated C1-C6 straight, branched or cyclic alkyl group, or optionally halogenated C1-C6 straight, branched or cyclic alkoxy group, A2 is a single bond or C1-C10 straight, branched or cyclic alkylene group in which an ether bond may intervene in a carbon-carbon bond, s is 0 or 1, t is an integer of 0 to 2, c is an integer satisfying: 0≤c≤5+2t−e, d is 0 or 1, e is an integer of 1 to 3, in case of e=1, X is an acid labile group, and in case of e=2 or 3, X is hydrogen or an acid labile group, at least one X being an acid labile group (Kotake, paragraph 0025). The aforementioned Polymer A1 disclosed by Kotake (and reproduced above) comprises a repeat unit of this type (the bottom most repeating unit).
Regarding Claim 5, Kotake discloses that the polymer preferably further comprises recurring units of at least one type selected from units having the formulae (B3), (B4), and (B5) (Kotake, paragraph 0026). The structures of each of formula (B3) to (B5) are reproduced below.
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The variable groups of each of these structures are defined in paragraph 0026 of Kotake. In particular, Polymer A1 (reproduced above) includes a repeating unit having the structure of formula (B3), wherein f has a value of 0.
Regarding Claim 6, Kotake discloses that it is preferred that the polymer further comprises recurring units of at least one type selected from units having the formulae (B6) to (B13) (Kotake, paragraph 0027). Formulas (B6) to (B13) of Kotake are analogous to Formulas (B6) to (B13) as recited by instant claim 6. Polymers P1 and P2 (see page 37 of Kotake) include one or more of these repeating units in combination with a repeating unit according to formula (B1). Examples 1-13 through 1-18, 1-20 through 1-23, and 1-31 through 1-35 utilize a polymer having at least one of these repeating units in a photoresist composition (see Table 1 on pages 38-39 of Kotake).
Regarding Claim 7, Kotake discloses that the positive resist composition may further comprise a fluorinated polymer comprising recurring units having the formula (C1) and recurring units of at least one type selected from units having the formulae (C2), (C3), (C4), and (C5) (Kotake, paragraph 0028). Formula (C1) is analogous to formula (D1) as recited by instant claim 7, whilst Formulae (C2), (C3), (C4), and (C5) are analogous to formulae (D2), (D3), (D4), and (D5), respectively, as recited by instant claim 7. Examples 1-5 to 1-7 (see Table 1 on Page 38 of Kotake) utilize such a polymer in combination with an onium salt, Polymer A1, and a photoacid generator.
Regarding Claim 8, Kotake discloses that the positive resist composition may further comprise an organic solvent (Kotake, paragraph 0029). In the Examples (see Example 1 in Table 1 on Page 38 of Kotake), PGMEA (propylene glycol monomethyl ether acetate) and EL (ethyl lactate) are used (Kotake, paragraph 0163).
Regarding Claim 10, Kotake discloses a resist pattern forming process comprising the steps of applying the resist composition onto a processable substrate to form a resist film thereon, exposing the resist film patternwise to high-energy radiation, and developing the resist film in an alkaline developer to form a resist pattern (Kotake, paragraph 0129).
Regarding Claim 11, Kotake discloses that the high-energy radiation source used to pattern the resist film is preferably EUV or EB (Kotake, paragraph 0131).
Regarding Claim 12, Kotake discloses that the substrate that the resist composition is applied to is a substrate for IC fabrication (such as Cr, CrO, CrON, MoSi2, SiN, SiON, TiN, WSi, BPSG, SOG, or organic antireflective coating), or a substrate for mask circuit fabrication (such as Cr, CrO, CrON, MoSi2, Si, SiO, or SiO2) (Kotake, paragraph 0130). Thus, Kotake discloses a substrate containing at least one element selected from chromium (Cr), silicon (Si), tantalum (Ta), molybdenum (Mo), cobalt (Co), nickel (Ni), tungsten (W), and tin (Sn). In the examples, the resist composition is spin coated onto a mask blank having the outermost surface of silicon oxide (Kotake, paragraph 0165).
Regarding Claim 13, Kotake discloses, in an inventive example, that the resist composition is applied to a mask blank having an outermost surface of silicon oxide (Kotake, paragraph 0165).
Regarding Claims 14 and 15, Kotake discloses an inventive example wherein the resist composition is spin coated onto a silicon wafer and baked to form a resist film (Kotake, paragraph 0170). An anti-charging (i.e. antistatic) film is disposed over the resist film (Kotake, paragraph 0170). Following exposure from an EB writing system, a patterned mask blank is obtained (Kotake, paragraph 0171-0172).
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JAYSON D COSGROVE whose telephone number is (571)272-2153. The examiner can normally be reached Monday-Friday 10:00-18:00.
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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.
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/JAYSON D COSGROVE/Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734