CTNF 18/182,626 CTNF 93490 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Priority 02-26 AIA Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. Information Disclosure Statement The information disclosure statement (IDS) submitted on 06/11/2024 has been considered by the examiner. Specification 07-29 AIA The disclosure is objected to because of the following informalities: the chemical structure formulae on the top of page 37 and on pages 45-48 are of poor resolution . Appropriate correction is required. Claim Rejections - 35 USC § 112 07-30-02 AIA The following is a quotation of 35 U.S.C. 112(b): (b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention. The following is a quotation of 35 U.S.C. 112 (pre-AIA), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. 07-34-01 Claim 6 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention . Regarding claim 6 , the claim recites "[t]he condensed cyclic compound of claim 1 represented by Formula 4: PNG media_image1.png 414 811 media_image1.png Greyscale However, claim 1 , from which claim 6 directly depends, recites [a] condensed cyclic compound represented by Formula 1: PNG media_image2.png 454 804 media_image2.png Greyscale The claim is indefinite because, from the above, it is unclear how Ar 21 , which occupied the same location as Ar 11 , can be defined as in (b) a substituted or unsubstituted group derived from a heteroaromatic ring, when the definition of Ar 11 does not comprise a heteroaromatic ring. For purposes of examination, the claim will be interpreted such that Ar 21 in Formula 4 must be (a) such that it is consistent with the definition of Ar 11 in Formula 1. Regarding claim 6 , the claim recites the definition of variables R 21 , R 22 , R 23 , R 24 , and R 25 in parenthesis. The claim is indefinite because it is unclear if the definitions provided as a parenthetical are optional or not. For purposes of examination, the claim will be interpreted such that the definition of R 21 , R 22 , R 23 , R 24 , and R 25 in the parenthesis is required. Regarding claim 6 , the claim recites the following proviso: PNG media_image3.png 308 829 media_image3.png Greyscale In the element (i)(b), it is unclear how "at least one hydrogen atom" is bound to two * in Formula 5 differs from "a ring-forming atom" is bound to two *in Formula 5 because the hydrogen is bound to a ring-forming atom. For purposes of examination, the claim will be interpreted such that two * in Formula 5 are bound to a ring-forming atom of Ar 21 , Ar 22 , Ar 23 , Ar 24 , or Ar 25 . Claim Rejections - 35 USC § 102 07-07-aia AIA 07-07 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 – 07-08-aia AIA (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. 07-15 AIA Claim s 1 and 14-20 are rejected under 35 U.S.C. 102( a)(1 ) as being anticipated by Zhang et al. CN-111606906-A (hereinafter "Zhang-CN", see English language machine translation referred to herein as "Zhang-MT") . It is noted that Zhang et al. CN-111606906-A is cited on the IDS of 06/11/2024. Regarding claim 1 and 14-20 , Zhang discloses an organic electroluminescent device comprising at least one organic layer sandwiched between a first electrode and a second electrode, wherein the at least one organic layer comprises a polycyclic nitrogen-containing compound (Zhang-MT, page 12 of 22, lines 22-25), wherein polycyclic nitrogen-containing compound is in a light emitting layer as a material with high light emitting efficiency with a host, or as a host with a further host compound and a doping material (Zhang-MT, page 2 of 22, lines 26-33; Zhang-MT, page 14 of 22, lines 18-38; and Zhang-MT, page 19 of 22, lines 14-17). Zhang exemplifies compounds of the polycyclic nitrogen-containing compound including 1-37 PNG media_image4.png 157 120 media_image4.png Greyscale (page 8), which is a condensed cyclic compound represented by Formula 1 wherein: Ar 11 and Ar 12 are each an unsubstituted group derived from an aromatic ring having 6 ring-forming atoms (a benzene group) and Ar 13 is a substituted group derived from an aromatic ring having 6 ring-forming atoms (a benzene group); X 11 is -CR X12 R X13 -; and R X11 is not required to be present, R X12 and R x13 are each a substituted aryl group and they are bound to each to form a ring, and R X14 and R X15 are not required to be present. Therefore, Zhang meets claims 1 and 14-20 . Claim Rejections - 35 USC § 103 07-20-aia AIA 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. 07-23-aia AIA 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. 07-20-02-aia AIA 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. 07-21-aia AIA Claim s 1-4 and 7-20 are rejected under 35 U.S.C. 103 as being unpatentable over Parham et al. US-20090295275-A1 (hereinafter "Parham") . Regarding claims 1-4, 7-9, and 14-20 , Parham teaches an organic electroluminescent devices comprising an anode, cathode, and at least one layer which comprises at least one organic compound of a formula (1) (¶ [0052]) PNG media_image5.png 262 259 media_image5.png Greyscale (¶ [0016]). Parham teaches the organic compound in the emitting layer employed as a mixture with one or more host materials as an emitting compound or as a host material (¶ [0054]-[0058]). Parham teaches the compound obtains high efficiency (¶ [0065]), increased stability and lifetime (¶ [0066]), improved sublimation (¶ [0067]), smaller Stokes shift (¶ [0068]), and high charge-carrier mobility (¶ [0069]). Parham teaches examples of the compound of formula (1) including Structure (3) PNG media_image6.png 325 356 media_image6.png Greyscale , Structure (5) PNG media_image7.png 238 256 media_image7.png Greyscale (page 5), and Structure (9) PNG media_image8.png 257 259 media_image8.png Greyscale , and Structure (11) PNG media_image9.png 240 256 media_image9.png Greyscale (page 6). Parham does not exemplify a compound of the claimed Formula 1. For example, the Structure (5) differs from the claimed compound in that one position corresponding to Y in the general formula of Parham is -C=O- instead of -O-, -S-, -NR-, -CRR-, -SiRR- and each of the Structure (3), Structure (9), and Structure (11) differ from the claimed compound in that two positions corresponding to Y in the general formula of Parham are -CRR- or -O- instead of -C=O-. However, Parham teaches that Y is independently selected from -O-, -S-, -NR-, -CRR-, -SiRR-, and -C=O-, among others (¶ [0018]) and exemplifies compound wherein Y is -O-, -S-, -NR-, -CRR-, -SiRR-, and -C=O- in paragraph [0040]. Therefore, given the general formula and teachings of Parham, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute one Y in Structure (5) for one of -O-, -S-, -NR-, -CRR-, -SiRR- as in one of the exemplified compounds and/or two Y in the Structure (9) and Structure (11) with -C=O-, because Parham teaches the variable may suitably be selected as such and exemplifies compound wherein Y is such. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful in the emitting layer of the device of Parham and possess the beneficial properties of high efficiency, increased stability and lifetime , improved sublimation, smaller Stokes shift, and high charge-carrier mobility, as taught by Parham. See MPEP § 2143.I.(B). The modified Structure (3) meets claimed Formula 1. The modified Structure (5) meets claimed Formula 1. The modified Structure (9) meets claimed Formula 1, Formula 6, and Formula 7. The modified Structure (11) meets claimed Formula 1 and Formula 2, and Formula 3. Therefore, the modified compounds of Parham meet claims 1-4, 7-9, and 14-20 . Regarding claims 10-13 , Parham the modified compounds as described above with respect to claim 1 . Parham does not exemplify a compound as recited in claim 10 . However, Parham teaches that the variable R in the formula (1) may be a branched alkyl group or an aromatic group, among others (¶ [0019]-[0020]), and teaches exemplary compounds wherein R is a branched alkyl group t-butyl group (see Structures (37) to (38) on page 12). Therefore, given the general formula and teachings of Parham, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute each of the phenyl substituents at the positions R in the modified Structure (9) with a t-butyl group, because Parham teaches the variable may suitably be selected as such and exemplifies compound wherein R is such. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful in the emitting layer of the device of Parham and possess the beneficial properties of high efficiency, increased stability and lifetime , improved sublimation, smaller Stokes shift, and high charge-carrier mobility, as taught by Parham. See MPEP § 2143.I.(B). The further modified Structure (9) has the structure PNG media_image10.png 261 199 media_image10.png Greyscale . Parham appears silent with respect to the properties of: (i) wherein an energy level of a highest occupied molecular orbital (HOMO) of the condensed cyclic compound is about -5.80 eV or more and about -4.40 eV or less, and an energy level of a lowest unoccupied molecular orbital (LUMO) of the condensed cyclic compound is about -2.40 eV or more and about -0.80 eV or less; (ii) wherein a peak of a fluorescence wavelength of the condensed cyclic compound is about 360 nanometers (nm) or more and about 515 nm or less, and a half-width of a peak in a fluorescence emission spectrum of the condensed cyclic compound is 30 nm or less; and (iii) wherein a rearrangement energy of the condensed cyclic compound is about 0 eV or more and 0.110 eV or less. The instant specification page 76 recites: PNG media_image11.png 265 568 media_image11.png Greyscale . Since Parham teaches the modified compound that corresponds to the claimed compound 2-11, the same structure as disclosed by the applicant, the properties of (i) to (iii) are considered to be inherent and would be expected to fall within the range in the claim, absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP § 2112 . Allowable Subject Matter 12-151-08 AIA 07-43 12-51-08 Claim 5 is 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. 13-03-01 AIA The following is a statement of reasons for the indication of allowable subject matter: The closest prior art, exemplified by Parham et al. US-20090295275-A1, teaches an organic electroluminescent devices comprising an anode, cathode, and at least one layer which comprises a bridged triarylamine derivative of a formula (1) (¶ [0052]) PNG media_image5.png 262 259 media_image5.png Greyscale (¶ [0016) and teaches examples of the compound including Structure (11) PNG media_image9.png 240 256 media_image9.png Greyscale (page 6). However, Parham does not teach a compound of any one of Formulae 1-1 to 1-18 wherein at least one of the aryl groups of the bridged triarylamine, Ar 11 , Ar 12 , and Ar 13 , is a carbazole, a dibenzofuran, or a dibenzothiophene instead of a benzene ring, as in the compounds of Formulae 1-1 to 1-18. Further, the prior art does not provide a reason to modify the compound of Parham such that at least one of the aryl groups of the bridged triarylamine, Ar 11 , Ar 12 , and Ar 13 , is a carbazole, a dibenzofuran, or a dibenzothiophene instead of a benzene ring to arrive at a compound of any one of Formulae 1-1 to 1-18 with a reasonable expectation of success . Conclusion 07-96 AIA The prior art made of record and not relied upon is considered pertinent to applicant's disclosure : CN-110437229-A, cited on the IDS of 06/11/2024, discloses compound on page 7, Org. Lett. 2021, 23, 958−962, cited on the IDS of 06/11/2024, discloses compound in Figure 1, and CN-114671872-A discloses compounds on page 19 such as Z-366 . Contact Information Any inquiry concerning this communication or earlier communications from the examiner should be directed to Elizabeth M. Dahlburg whose telephone number is 571-272-6424. The examiner can normally be reached Monday through Thursday, 9 a.m. to 4 p.m. ET, and alternate Fridays. 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, Jennifer Boyd can be reached at 571-272-7783. 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. /ELIZABETH M. DAHLBURG/Primary Examiner, Art Unit 1786 Application/Control Number: 18/182,626 Page 2 Art Unit: 1786 Application/Control Number: 18/182,626 Page 3 Art Unit: 1786 Application/Control Number: 18/182,626 Page 4 Art Unit: 1786 Application/Control Number: 18/182,626 Page 6 Art Unit: 1786 Application/Control Number: 18/182,626 Page 7 Art Unit: 1786 Application/Control Number: 18/182,626 Page 8 Art Unit: 1786
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