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, see pages 5-6, filed 24 August 2026, with respect to the rejection(s) of claim(s) 1-6 under 35 U.S.C. 103 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of US 20190315684 A1 (hereby referred to as Anryu).
Applicant has amended independent claim 1 to further specify the bonding positions of Rb11, Rb12, and Rb13. Specifically, these groups are bonded to their respective phenyl rings in the meta and/or para bonding positions. The definition of Rb21, Rb22, and Rb23 has been expanded to include groups other than a hydrogen atom as well. Applicant argues that the previously cited prior art (Ikeda and Nagamine) fails to disclose or suggest the invention of claim 1, as amended. Particularly, Applicant argues that the acid generator disclosed by Ikeda includes halogen atoms in the ortho bonding position on the phenyl ring. Upon review of Ikeda’s disclosure, the Examiner finds the Applicant’s arguments persuasive, as Ikeda requires that at least one of the fluorine atoms be bonded to a carbon atom adjacent to a carbon atom that is bonded to a sulfur atom (Ikeda, paragraph 0400). In other words, Ikeda requires a fluorine atom in the ortho position. Therefore, Applicant’s arguments are found to be persuasive and the previous rejection is withdrawn. However, a new rejection is presented in view of US 20190315684 A1 (hereby referred to as Anryu), as explained below.
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) 1-6 are rejected under 35 U.S.C. 103 as being unpatentable over US 20190315684 A1 (hereby referred to as Anryu) in view of US 2017/0285469 A1 (hereby referred to as Nagamine).
Regarding Claims 1-4, Anryu discloses a salt, acid generator, resist composition, and a method for producing a resist pattern. The resist composition comprises a salt and a resin having an acid-labile group (Anryu, paragraph 0224). The resin having an acid-labile group is a resin whose solubility in a developer changes by the action of an acid. The composition preferably includes a quencher and a solvent (Anryu, paragraph 0225). The salt is represented by formula (I), which is reproduced below (Anryu, paragraph 0024).
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In formula (I), R1 to R5 represents a halogen atom, such as fluorine (Anryu, paragraph 0006 and 0026). R6 to R8 represents a halogen atom, a hydroxy group, a fluoroalkyl group, or an alkyl group (Anryu, paragraph 0007). The value of m5 is 1 to 5, the value of m6 is 0 to 3, the value of m7 is 0 to 3, and the value of m8 is 0 to 4, with the stipulation that 1≤m5+m8≤5 (Anryu, paragraph 0008-0011). Lastly, AI- represents an organic anion (Anryu, paragraph 0012). The salt functions as an acid generator (Anryu, paragraph 0171). Anryu provides inventive examples in Table 2 (refer to pages 99-100 of Anryu). Notably, Composition 6 comprises 10 parts of resin A1, 1.5 parts of salt I-43, and 0.35 parts of quencher C1 (refer to page 100 of Anryu). Resin A1 is a copolymer whose structure is reproduced below (Anryu, paragraph 0688 and 0692).
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As can be seen above, resin A1 is comparable to the resins used in the instant application’s examples (refer to paragraph 0322 and 0324 of the instant application’s specification). Furthermore, salt I-43 is a sulfonium salt whose structure is reproduced below (Anryu, paragraph 0661-0662 and 0700).
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Salt I-43 is structurally equivalent to acid generator (B0-3) used in the instant application’s inventive examples (refer to page 145 of the instant application’s specification). The cation of the salt comprises fluorine atoms only in meta and/or para positions on the phenyl rings. Thus, salt I-43 is an acid generator according to instant claims 1-3. The structure of quencher C1 is provided on page 100 of Anryu. Quencher C1 is a salt having a carboxylic acid, but Anryu does not provide a pKa value of the salt.
However, Anryu does not teach that the quencher has a carboxylic acid with a pKa of 0.3 to 2.5 as a generated acid. Nagamine teaches a resist composition and a method for forming a resist pattern. The resist composition comprises a base material component (A), whose solubility in the developing solution changes under the action of an acid, and an acid diffusion control agent component (D) (Nagamine, paragraph 0060). The Examiner notes that a quencher and an acid diffusion control agent are defined to be same thing (refer to paragraph 0347 of Nagamine). The component (A) is preferably a resin soluble in the developing solution (Nagamine, paragraph 0077). The acid diffusion control agent component (D) includes the compound (D1), of which a conjugate acid has an acid dissociation constant (pKa) of less than 3 (Nagamine, paragraph 0348). It’s further preferable that the pKa of the conjugate acid is 0.4 or more and less than 3 (Nagamine, paragraph 0352). The preferred structure of the compound (D1), which has the formula (d1), is reproduced below (Nagamine, paragraph 0356).
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The structure of compound (d1) is the same as the base component (d0) described by the instant application (see paragraph 0269-0270 of the instant application’s specification). Nagamine provides several inventive examples of the resist composition (Nagamine, paragraph 0640, refer to Table 1 on pages 66-67). For instance, Example 2 (see Table 1 on page 66 of Nagamine) comprises 100 parts component (A1)-1, 4.13 parts component (D1)-2, 10 parts component (B)-1, 1.5 parts component (E)-1, 3.0 parts component (F)-1, 100 parts component (S)-1, and 4000 parts of component (S)-2. Component (A1)-1 is a polymer represented by chemical formula (A1-1) (Nagamine, paragraph 0642; see also the structure on page 65 of Nagamine). Component (D1)-2 is an acid diffusion control agent represented by formula (d1-12) whose conjugate acid has a pKa of 1.53 (Nagamine, paragraph 0647; see also the structure on page 67 of Nagamine, which is reproduced below). Component (B)-1 is an acid generator represented by formula (B)-1 (Nagamine, paragraph 0651; see also the structure on page 68 of Nagamine). Component (E)-1 is salicylic acid (Nagamine, paragraph 0652). Component (F)-1 is a fluorinated polymer (Nagamine, paragraph 0653; see also the structure on page 68 of Nagamine). Component (S)-1 is γ-butyrolactone and component (S)-2 is a mixed solvent of PGMEA/PGME/cyclohexanone (Nagamine, paragraph 0654-0655).
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The structure of formula (d1-12) is an embodiment of formula (d0-8), as recited by the instant application’s specification (see paragraph 0283 of the instant application’s specification). The instant application utilizes the same acid diffusion control agent in the inventive examples (see component D0-8, paragraph 0330 of the instant application’s specification). The instant application reports a pKa for this salt is 1.53 (see page 147 of the instant application’s specification). The Examiner notes that the acid diffusion control agent represented by formula (d1-12) of Nagamine satisfies the requirements of instant claims 1 and 4.
Anryu and Nagamine are analogous art because both references pertain to resist compositions comprising a resin, a photoacid generator, and an acid diffusion control agent. It would have been obvious to one having ordinary skill in the art before the filing date of the instant application to replace the quencher C1 disclosed by the inventive examples of Anryu with an acid diffusion control agent having a conjugate acid having a pKa between 0.4 and 3, as taught by Nagamine, in the resist composition disclosed by Anryu because the acid diffusion control agent having a conjugate acid having a pKa below 3 and above 0.4 provides exposure stability, reduces roughness, and improves other lithographic properties of the resist composition (Nagamine, paragraph 0353). When the resist composition of Anryu is modified to include the acid diffusion control agent taught by Nagamine, the resulting resist composition satisfies the invention according to instant claims 1-4.
Regarding Claims 5-6, Anryu discloses a method for producing a resist pattern comprising the steps of applying the resist composition on a substrate, drying the composition to form a composition layer, exposing the composition layer, heating the exposed composition layer, and developing the heated composition layer (Anryu, paragraph 0621). Exposure may be performed using an extreme ultraviolet (EUV) source or an electron beam (Anryu, paragraph 0624).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. US 20190227432 A1 (hereby referred to as Shiratani) teaches a radiation-sensitive composition comprising an anion that is a conjugated base of an acid, wherein the acid has a pKa no greater than 3 (Shiratani, paragraph 0010). Page 9 of Shiratani depicts several anionic species that match those of the base component (D) described by the instant application.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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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/JAYSON D COSGROVE/Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734
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