PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

§102 §103

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 . Summary of Claims Claims 1–11 are withdrawn due to Applicant’s response to the Requirement for Restriction dated 07/29/2026. Claims 12–17 are pending. Priority Acknowledgment is made of Applicant's claim for foreign priority based on an application filed in Korea on 02/11/2022. Applicant claims priority based on an application filed in Korea on 01/11/2023, however a certified copy was not filed. Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)- (d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e). Failure to provide a certified translation may result in no benefit being accorded for the non-English application. Claim Rejections - 35 USC § 102 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. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. Claims 12–14 and 16–17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Wang et al. (CN 113214237 A, provided in Applicant’s IDS filed on 02/02/2023, hereinafter “Wang”). An English translation was provided in this Office Action. Regarding Claim 12, Wang discloses compounds such as Compound I-013 [pg. 3] which reads on Applicant’s Formula 1 (shown below), PNG media_image1.png 138 248 media_image1.png Greyscale PNG media_image2.png 261 260 media_image2.png Greyscale wherein: ring A represents 4 sequentially fused benzene rings, X1 is -O-, Y1 is -N=, Ra is a C6 aryl (phenyl), Rb is a 6-membered heteroaryl (triazine) substituted with two C6 aryl groups (phenyls), n is 1. As drawn, the oxygen atom has a single bond and a double bond while the nitrogen atom has two single bonds in Compound I-013. This would result in a positively charged oxygen atom and a negatively charged nitrogen atom wherein the overall molecule would be zwitterionic. It is the Examiner’s position that a person having ordinary skill in the art would at once envisage that this is a drawing error, and the compounds taught by Wang should instead have an oxygen atom with two single bonds and a nitrogen atom with a single bond and a double bond, resulting in an overall neutral compound. Note that many of the compounds taught by Wang have the correct bonding pattern, such as Compound I-001 [0025]. Additionally, the compounds taught by Wang are represented by Wang’s Formula 1 wherein X and Y may each be -N=, -O-, or -S- [0009] – [0012]. Notably, in that definition “-N-”, signifying a nitrogen with two single bonds, is not an option. In the alternative, Compound I-013 is represented by Wang’s Formula 1 (shown below), wherein X and Y may each be -N=, -O-, or -S- [0009] – [0012]. Wang further teaches the compounds of present invention can significantly improve the brightness, luminous efficiency, and life of an electroluminescent device, and reduce the driving voltage [pg. 7 of English translation]. PNG media_image3.png 325 215 media_image3.png Greyscale PNG media_image4.png 297 316 media_image4.png Greyscale Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to choose X to be -N= (i.e. a nitrogen with a single bond and double bond) and Y to be -O- (i.e. an oxygen with two single bonds), because it would have been choosing between -N=, -O-, or -S-, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the host in the light emitting layer of the organic light emitting device of Wang and possessing the benefits taught by Wang. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Wang’s Formula 1 having the benefits taught by Wang in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E). A corrected version of Compound I-013 is shown above next to Wang’s Formula 1. Regarding Claim 13, Compound I-013 reads on Applicant’s Formula 1’-1, Formula 1A, and Formula 1B (shown below), wherein R1 and R2 are represented by Formula 1A, while R3 and R4 are represented by Formula 1B. R5 to R12 and R14 are each hydrogen, R13 is a 6-membered heteroaryl (triazine) substituted with two C6 aryl groups (phenyls). X1 is -O-, Y1 is -N=, Ra is a C6 aryl (phenyl). PNG media_image5.png 176 161 media_image5.png Greyscale PNG media_image6.png 195 346 media_image6.png Greyscale PNG media_image4.png 297 316 media_image4.png Greyscale Regarding Claim 14, Compound I-013 reads on Applicant’s Formula 11’-1 (shown below). R5 to R12 and R14 are each hydrogen, R13 is a 6-membered heteroaryl (triazine) substituted with two C6 aryl groups (phenyls). X1 is -O-, Y1 is -N=, Ra is a C6 aryl (phenyl). PNG media_image7.png 260 166 media_image7.png Greyscale PNG media_image4.png 297 316 media_image4.png Greyscale Regarding Claim 16, Compound I-013 is identical to Applicant’s Compound H2-261 (shown below). PNG media_image8.png 193 215 media_image8.png Greyscale PNG media_image4.png 297 316 media_image4.png Greyscale Regarding Claim 17, Wang discloses the organic light emitting device of Example 1 including an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode [pg. 12–13 of English translation], wherein the light emitting layer comprises Compound I-001 [0049]. Compound I-001 is identical to Compound I-013 aside from the nitrogen and the oxygen being substituted for each other. Compound I-001 reads on Applicant’s Formula 1 (shown below), PNG media_image1.png 138 248 media_image1.png Greyscale PNG media_image9.png 246 263 media_image9.png Greyscale wherein: ring A represents 4 sequentially fused benzene rings, X1 is -N=, Y1 is -O-, Ra is a C6 aryl (phenyl), Rb is a 6-membered heteroaryl (triazine) substituted with two C6 aryl groups (phenyls), n is 1. Claims 12–14 is rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Cassiers et al. (US 3,279,918, hereinafter “Cassiers”). Regarding Claim 12, Cassiers discloses Compound 7 [Table 1] which reads on Applicant’s Formula 1 (shown below), PNG media_image1.png 138 248 media_image1.png Greyscale PNG media_image10.png 409 254 media_image10.png Greyscale wherein: ring A represents 4 sequentially fused benzene rings, X1 is -O-, Y1 is -N=, Ra is -L’1-NR’1R’2, L’1 is a C6 arylene (phenylene), R’1 and R’2 are each a C1 alkyl (methyl), Rb is hydrogen, n is 10. Regarding Claim 13, Compound 7 reads on Applicant’s Formula 1’-1, Formula 1A, and Formula 1B (shown below), wherein R1 and R2 are represented by Formula 1A, while R3 and R4 are represented by Formula 1B. R5 to R14 are each hydrogen. X1, Y1, and Ra are the same as defined above in claim 12. PNG media_image5.png 176 161 media_image5.png Greyscale PNG media_image6.png 195 346 media_image6.png Greyscale PNG media_image10.png 409 254 media_image10.png Greyscale Regarding Claim 14, Compound 7 reads on Applicant’s Formula 11’-1 (shown below). R5 to R14 are each hydrogen. X1, Y1, and Ra are the same as defined above in claim 12. PNG media_image7.png 260 166 media_image7.png Greyscale PNG media_image10.png 409 254 media_image10.png Greyscale Claim 12 is rejected under 35 U.S.C. 102(a)(2) as being anticipated by Kang et al. (US 2022/0123223 A1, hereinafter “Kang”). Regarding Claim 12, Kang discloses Compound H1-107 [pg. 140] which reads on Applicant’s Formula 1 (shown below), PNG media_image1.png 138 248 media_image1.png Greyscale PNG media_image11.png 338 272 media_image11.png Greyscale wherein: ring A represents 4 sequentially fused benzene rings, X1 is -N=, Y1 is -O-, Ra is a C6 aryl (phenyl), Rb is -L’1-NR’1R’2, L’1 is a single bond, R’1 is a 13-membered heteroaryl (dibenzofuran), R’2 is C6 aryl (phenyl) substituted with a C6 aryl (phenyl), n is 1. Claim 12–15 and 17 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Jeong et al. (WO 2023/182775 A1, hereinafter “Jeong”). An English translation of Jeong was provided in this Office Action. Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216. Regarding Claims 12 and 17, Jeong discloses the organic light emitting device of Example 4 [Table 1] including an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode [561]. The light emitting layer comprises Compound 190 [452] which reads on Applicant’s Formula 1 (shown below), PNG media_image1.png 138 248 media_image1.png Greyscale PNG media_image12.png 261 196 media_image12.png Greyscale wherein: ring A represents 4 sequentially fused benzene rings, X1 is -O-, Y1 is -N=, Ra is a C6 aryl (phenyl), Rb is -L’1-NR’1R’2, L’1 is a single bond, R’1 is a 13-membered heteroaryl (dibenzofuran), R’2 is C6 aryl (phenyl) substituted with a C6 aryl (phenyl), n is 1. Regarding Claim 13, Compound 190 reads on Applicant’s Formula 1’-1, Formula 1A, and Formula 1B (shown below), wherein R1 and R2 are represented by Formula 1B, while R3 and R4 are represented by Formula 1A. R5 to R12 and R14 are each hydrogen, R13 is -L’1-NR’1R’2, L’1 is a single bond, R’1 is a 13-membered heteroaryl (dibenzofuran), R’2 is C6 aryl (phenyl) substituted with a C6 aryl (phenyl), X1 is -O-, Y1 is -N=, Ra is a C6 aryl (phenyl). PNG media_image5.png 176 161 media_image5.png Greyscale PNG media_image6.png 195 346 media_image6.png Greyscale PNG media_image12.png 261 196 media_image12.png Greyscale Regarding Claim 14, Compound 190 reads on Applicant’s Formula 11’-2 (shown below). R5 to R12 and R14 are each hydrogen, R13 is -L’1-NR’1R’2, L’1 is a single bond, R’1 is a 13-membered heteroaryl (dibenzofuran), R’2 is C6 aryl (phenyl) substituted with a C6 aryl (phenyl). X1 is -O-, Y1 is -N=, Ra is a C6 aryl (phenyl). PNG media_image13.png 242 181 media_image13.png Greyscale PNG media_image12.png 261 196 media_image12.png Greyscale Regarding Claim 15, R13 in Compound 190 is represented by Applicant’s Formula Rb-1 (shown below), wherein L’1 is a single bond, R’1 is a 13-membered heteroaryl (dibenzofuran), R’2 is C6 aryl (phenyl) substituted with a C6 aryl (phenyl). PNG media_image14.png 167 161 media_image14.png Greyscale PNG media_image12.png 261 196 media_image12.png Greyscale 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. 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 16 is rejected under 35 U.S.C. 103 as being unpatentable over Jeong et al. (WO 2023/182775 A) as applied to claims 12–15 and 17 above. Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216. Compound 190 does not read on Applicant’s Compound C-62 since the nitrogen and the oxygen substituted for one another and the dibenzofuran is bonded in the 2-position instead of the 1-position. PNG media_image15.png 337 175 media_image15.png Greyscale PNG media_image12.png 261 196 media_image12.png Greyscale Compound 190 is represented by Jeong’s Chemical Formula B (shown below) wherein X1 is O [18] – [20]. Jeong also teaches Chemical Formula A (shown below), wherein the only difference between Chemical Formula A and Chemical Formula B is that the nitrogen and X1 are substituted for one another. Jeong teaches the compounds of present disclosure may be used as the host in the light emitting layer of an organic light emitting device to provide low voltage, high efficiency, and a long lifetime [11] – [12]. PNG media_image16.png 181 308 media_image16.png Greyscale PNG media_image17.png 181 287 media_image17.png Greyscale PNG media_image12.png 261 196 media_image12.png Greyscale Therefore, given the general formula and teachings of Jeong, 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 nitrogen and oxygen for one another, because Jeong teaches the variable may suitably be selected as nitrogen or oxygen. The substitution would have been one preferred 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 as a host in the light emitting layer of the organic light emitting device of Jeong and possess the low voltage, high efficiency, and long life benefits taught by Jeong. See MPEP 2143.I.(B). Additionally, the dibenzofuran is bonded in the 2-position instead of the 1-position in Compound 190. Jeong teaches Compound 18 wherein the dibenzofuran is bonded in the 2-position and Compound 21 wherein the dibenzofuran is bonded in the 1-position [156] – [159] (shown below). PNG media_image18.png 218 171 media_image18.png Greyscale PNG media_image19.png 215 193 media_image19.png Greyscale PNG media_image12.png 261 196 media_image12.png Greyscale Therefore, given the general formula and teachings of Jeong, 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 the bonding of the dibenzofuran from the 2-position to the 1-position, because Jeong teaches the variable may suitably be selected as the 2-position or the 1-position, as shown in Compound 18 and Compound 21. The substitution would have been one preferred 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 as a host in the light emitting layer of the organic light emitting device of Jeong and possess the low voltage, high efficiency, and long life benefits taught by Jeong. See MPEP 2143.I.(B). The modified version of Compound 190, as described above (hereinafter “Modified 190”), is identical to Applicant’s Compound C-62 (shown below). PNG media_image15.png 337 175 media_image15.png Greyscale PNG media_image20.png 455 232 media_image20.png Greyscale Claims 12–15 and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Wendeborn et al. (US 2018/0258053 A1, hereinafter “Wendeborn”) in view of Ma et al. (US 2011/0266526 A1, hereinafter “Ma”). Regarding Claim 12–15 and 17, Wendeborn teaches Compound 1 (shown below). However, Compound 1 fails to read on Applicant’s Formula 1 since it does not comprise 4 benzene rings which are sequentially fused (i.e. fused adjacent to one another). Compound 1 is represented by Wendeborn’s Formula (XIIb) [0081]. Wendeborn teaches that R15 and R16 may be fused together to form Group 1 (shown below) [0085]. Ma teaches aromatic fused rings increase the conjugation of a compound, leading to more extended π-electron delocalization and stabilization of charge in the oxidized or reduced state of the molecule resulting in good performance and stability when used in an organic light emitting device [0058]. PNG media_image21.png 253 319 media_image21.png Greyscale PNG media_image22.png 301 343 media_image22.png Greyscale PNG media_image23.png 237 129 media_image23.png Greyscale Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to fuse together R15 and R16 to form Group 1 in Compound 1, based on the teaching of Wendeborn in view of Ma. The motivation for doing so would have been to stabilize the charge in the oxidized or reduced state of the molecule resulting in good performance and stability when the compound is used in an organic light emitting device, as taught by Ma. Per Claim 12, the modified version of Compound 1, as described above (hereinafter “Modified 1”), reads on Applicant’s Formula 1 (shown below), PNG media_image1.png 138 248 media_image1.png Greyscale PNG media_image24.png 314 397 media_image24.png Greyscale wherein: ring A represents 4 sequentially fused benzene rings, X1 is -O-, Y1 is -N=, Ra is a C10 aryl (naphthyl), Rb is -L’1-NR’1R’2, L’1 is a single bond, R’1 is a C10 aryl (naphthyl), R’2 is a C6 aryl (phenyl), n is 2. Regarding Claim 13, Modified 1 reads on Applicant’s Formula 1’-1, Formula 1A, and Formula 1 B (shown below), wherein R1 and R2 are represented by Formula 1A, while R3 and R4 are represented by Formula 1B. R5, R7, R8, R9, and R11 to R14 are each hydrogen, R6 and R10 are each -L’1-NR’1R’2, L’1 is a single bond, R’1 is a C10 aryl (naphthyl), R’2 is a C6 aryl (phenyl), X1 is -O-, Y1 is -N=, Ra is a C6 aryl (phenyl). PNG media_image5.png 176 161 media_image5.png Greyscale PNG media_image6.png 195 346 media_image6.png Greyscale PNG media_image24.png 314 397 media_image24.png Greyscale Regarding Claim 14, Modified 1 reads on Applicant’s Formula 11’-2 (shown below). R5, R7, R8, R9, and R11 to R14 are each hydrogen, R6 and R10 are each -L’1-NR’1R’2, L’1 is a single bond, R’1 is a C10 aryl (naphthyl), R’2 is a C6 aryl (phenyl), X1 is -O-, Y1 is -N=, Ra is a C6 aryl (phenyl). PNG media_image25.png 241 190 media_image25.png Greyscale PNG media_image24.png 314 397 media_image24.png Greyscale Regarding Claim 15, R6 and R10 in Modified 1 are represented by Applicant’s Formula Rb-1 (shown below), wherein L’1 is a single bond, R’1 is a C10 aryl (naphthyl), R’2 is a C6 aryl (phenyl). PNG media_image14.png 167 161 media_image14.png Greyscale PNG media_image24.png 314 397 media_image24.png Greyscale Regarding Claim 17, Wendeborn fails to disclose an organic light emitting device comprising Modified 1. Wendeborn teaches an organic light emitting device comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and a cathode [0248]. The light emitting layer comprises a compound of present disclosure as a host ([abstract] and [0248]). Wendeborn further teaches a device comprising a compound of present disclosure as a host results in an improved efficiency, stability, and manufacturability [abstract]. Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to use Modified 1 as a host in an organic light emitting device, because this would have been combining the prior art elements of Wendeborn according to known methods to yield predictable results of an organic light emitting device with an improved efficiency, stability, and manufacturability, as taught by Wendeborn. See MPEP 2143.I.(A). Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to JAMES RICHARD FORTWENGLER whose telephone number is (571)272-5433. The examiner can normally be reached Monday - Friday, 8 am - 5 pm. 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, Marla McConnell can be reached at (571) 270-7692. 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. /J.R.F./Examiner, Art Unit 1789 /MARLA D MCCONNELL/Supervisory Patent Examiner, Art Unit 1789