CTNF 18/032,358 CTNF 95254 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. Specification 07-29 AIA The disclosure is objected to because of the following informalities: The resolution of images for some of structural formulas are poor such that some of variables in the structural formulas are illegible (see structures on line 30 of page 71, lines 20-30 of page 72, all structural formulas on page 73-74, and line 10 of page 75) . Appropriate correction is required. Claim Rejections - 35 USC § 103 07-06 AIA 15-10-15 In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status. 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 16-22 and 24-30 are rejected under 35 U.S.C. 103 as being unpatentable over Hara et al. (US 2021/0151689 A1, hereafter Hara) as evidenced by Kim et al. (US 2022/0102645 A1, hereafter Kim) . Regarding claims 16, 18-22, 24-26, and 28-29 , Hara discloses a compound (Formula G0) having electron transport property and used for an organic electroluminescent device ([0012], [0015]-[0016]). PNG media_image1.png 372 689 media_image1.png Greyscale Hara exemplifies Compound 109 ([0093]). The Compound 109 of Hara has similar structure as Applicant’s Formula (1). The only difference is that the phenylene group at the position corresponding to (Ar) n of Formula G0 of Hara is required to be a direct bond; however, Hara does teach the structure corresponding to the (Ar) n of the Formula G0 of Hara can be a single bond because Hara does teach n can be 0 ([0016]). Hara exemplifies compounds wherein the structure corresponding to (Ar) n of Formula G0 of Hara is 0 (see embodiments including at least compounds 102 and 117 in [0093]). At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound 109 of Hara by substituting the phenylene group at the position corresponding to (Ar) n of Formula G0 of Hara with a single bond, as taught by Hara. The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of phenylene with a single bond at the position corresponding to (Ar) n of Formula G0 of Hara would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified structures at the position corresponding to (Ar) n of Formula G0 of Hara in the disclosure (i.e. single bond, phenylene, or biphenylene). The selection of single bond would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E). PNG media_image2.png 296 540 media_image2.png Greyscale The modification provides Modified compound of Hara which has identical structure as Applicant’s Formula (1). Hara does not disclose a specific organic electroluminescent device comprising the Modified compound of Hara; however, Hara does teach the compound of Hara can be used as the host material of the cohost system of an organic electroluminescent device ([0115]-[0116], [0118]). Hara teaches that a hole transporting host material including PCCP can be used as the other part of the cohost system in the device of Hara ([0148], [0154]). PCCP has identical structure as Applicant’s Formula (2). PNG media_image3.png 206 509 media_image3.png Greyscale Hara teaches the structure of an organic electroluminescent device comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer (Compound of Hara as a host, PCCP as a host, and Ir(ppy)2(mdppy) as a phosphorescent emitter), an electron injection layer, and a cathode, wherein the light emitting layer is formed by a co-evaporation method (Light emitting element 1 in Table 1 and [0340]-[0346]). At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Modified compound of Hara by incorporating it into an organic electroluminescent device as the electron transport host material, as taught by Hara. The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the compound of Hara represented by Formula G0 in the organic electroluminescent device of Hara would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The modification provides Modified organic electroluminescent device of Hara comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer (Modified compound of Hara as a host, PCCP as a host, and Ir(ppy)2(mdppy) as a phosphorescent emitter), an electron injection layer, and a cathode, wherein the light emitting layer is formed by a gas phase deposition (i.e. co-evaporation); the organic electroluminescent device is OLED; and the light emitting layer material including two hosts and the phosphorescent emitter are a mixture, meeting all the limitations of claims 16, 18-22, 24, and 28-29 . Kim evidences that the co-evaporation is a mixed deposition method in which each materials are put into respective individual crucible source and a current is applied to each cells simultaneously to evaporate the materials and to perform mixed deposition ([0119]). Thus, in the co-evaporation process of the Modified organic electroluminescent device of Hara, two hosts and the phosphorescent dopant are simultaneously evaporated from separate crucibles to form a mixture of gases which are deposited to the target, meeting all the limitations of claims 25-26 . Regarding claim 17 , the Modified organic electroluminescent device of Hara reads on all the features of claims 16 and 28 as outlined above. The device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer (Modified compound of Hara as a host, PCCP as a host, and Ir(ppy)2(mdppy) as a phosphorescent emitter), an electron injection layer, and a cathode. The Modified compound of Hara has similar structure as Applicant’s Formula (1a). The only difference is that in the Modified compound of Hara, the benzofuropyrimidine group is bonded to the position 1 of the dibenzothiophene (see the annotated numbers in the figure above) while the Applicant’s Formula (1a) requires the benzofuropyrimidine is bonded to the position 4 of the dibenzothiophene ring. However, Hara does not restrict the bonding position of the benzofuropyrimidine group in the ring A 1 of Formula G0 ([0057]), indicating that the benzofuropyrimidine group can be bonded to the ring A 1 at any substitutable position of the ring A 1 . At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Modified compound of Hara by substituting the bonding position of the benzofuropyrimidine group from the position 1 of the dibenzothiophene of the ring A 1 from the position 4, as taught by Hara. The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the bonding position of the benzofuropyrimidine group in the ring A 1 of the Formula G0 would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of substitution positions in the ring A 1 . The selection of position 4 would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, the compounds of the Modified compound of Hara is a position isomer with similar compound in which the benzofuropyrimidine is bonded to the position 4 of the dibenzothiophene ring. With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II. Therefore, at the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to modify Modified compound of Hara shown above such that the benzofuropyrimidine is bonded to the position 4 of the dibenzothiophene ring. A compound in which the benzofuropyrimidine is bonded to the position 4 of the dibenzothiophene ring would represent a position isomer of the Compound of Hara. One of ordinary skill in the art would expect that the position isomers having each respective structure would act in similar manner. The modification provides Modified compound of Hara (2). PNG media_image4.png 334 675 media_image4.png Greyscale Regarding claims 27 and 30 , the Modified organic electroluminescent device of Hara reads on all the features of claims 16 and 28 as outlined above. The device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer (Modified compound of Hara as a host, PCCP as a host, and Ir(ppy)2(mdppy) as a phosphorescent emitter), an electron injection layer, and a cathode, wherein the light emitting layer is formed by a gas phase deposition (i.e. co-evaporation); the organic electroluminescent device is OLED; and the light emitting layer material including two hosts are a mixture. The device is not formed by a solution process; however, Hara does teach that the light emitting layer can be formed by a solution process including an inkjet or spin coating process ([0171], [0242]). Because the light emitting layer materials including the hosts and the dopants are each solid, a solvent is required to dissolve the solid materials in a solvent and form a solution for the inkjet or spin coating process. It is also known in the art that the inkjet or spin coating process is cost effective as compared to the vacuum evaporation method since the evaporation method requires relatively more expensive vacuum instruments. At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Modified organic electroluminescent device of Hara by substituting the process to form the light emitting layer from the evaporation process with a solution process (i.e. inkjet or spin coating method), wherein the host and dopant materials are dissolved in a solvent to make a solution for the inkjet or spin coating method, as taught by Hara. The motivation of doing so would have been to prepare the device with more cost effective solution process, based on the teaching of Hara. Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the evaporation process to the solution process would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The modification provides the Modified electroluminescent device of Hara (2) comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer (Modified compound of Hara as a host, PCCP as a host, and Ir(ppy)2(mdppy) as a phosphorescent emitter), an electron injection layer, and a cathode, wherein the light emitting layer is formed by a solution process of inkjet or spin coating method; the inkjet or spin coating method is applied from a solution which is a mixture of a solvent, the Modified compound of Hara, PCCP, and Ir(ppy)2(mdppy); and the solution is equated with a formulation . 07-21-aia AIA Claim 23 is rejected under 35 U.S.C. 103 as being unpatentable over Hara et al. (US 2021/0151689 A1) as applied to claims 16-22 and 24-30 above, further in view of Park et al. (US 2021/0399222 A1, hereafter Park) . Regarding claim 23 , the Modified organic electroluminescent device of Hara reads on all the features of claims 16 and 28 as outlined above. The device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer (Modified compound of Hara as a host, PCCP as a host, and Ir(ppy)2(mdppy) as a phosphorescent emitter), an electron injection layer, and a cathode. The hole transport layer material of the device is not a monoamine compound having no carbazole group; however, Hara does teach that the hole injection layer and the hole transport layer can be formed by an aromatic amine compounds ([0172] and [0178]). Park discloses a first compound of Formula 1 used for a hole injection layer and a second compound of Formula 2 used for a hole transport layer (Abstract, [0010]-[0011], [0016]). Park exemplified use of the Compound 1-2 of Park in a hole injection layer, and the Compound 1-1 of Park in a hole transport layer (Example 1-1 in Table 2). PNG media_image5.png 309 575 media_image5.png Greyscale Both compounds of Park are each a monoamine compound containing no carbazole group. Park teaches that the an organic electroluminescent device wherein the hole injection layer and the hole transport layers are formed according to the teaching of Park provides a low deriving voltage, high efficiency, and a long lifespan ([0088]). At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Modified organic electroluminescent device of Hara by substituting the hole injection and transport layers with the hole injection layer containing the Compound 1-1 of Park and the hole transport layer containing the Compound 1-2 of Park. The motivation of doing so would have been to provide a low deriving voltage, high efficiency, and a long lifespan, based on the teaching of Park. Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the hole injection and transport layer materials with aromatic amine compounds would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The modification provides the Organic electroluminescent device of Hara as modified by Park comprises an anode, a hole injection layer (Compound 1-2 of Park), a hole transport layer (Compound 1-1 of Park), a light emitting layer (Modified compound of Hara as a host, PCCP as a host, and Ir(ppy)2(mdppy) as a phosphorescent emitter), an electron injection layer, and a cathode, wherein the hole injection and transport layers are an organic layer. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to SEOKMIN JEON whose telephone number is (571)272-4599. The examiner can normally be reached Monday - Friday 8:30am to 5:00pm EST. 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. 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If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /SEOKMIN JEON/Primary Examiner, Art Unit 1786 Application/Control Number: 18/032,358 Page 2 Art Unit: 1786 Application/Control Number: 18/032,358 Page 4 Art Unit: 1786 Application/Control Number: 18/032,358 Page 5 Art Unit: 1786 Application/Control Number: 18/032,358 Page 6 Art Unit: 1786 Application/Control Number: 18/032,358 Page 7 Art Unit: 1786 Application/Control Number: 18/032,358 Page 8 Art Unit: 1786 Application/Control Number: 18/032,358 Page 9 Art Unit: 1786 Application/Control Number: 18/032,358 Page 10 Art Unit: 1786 Application/Control Number: 18/032,358 Page 11 Art Unit: 1786 Application/Control Number: 18/032,358 Page 12 Art Unit: 1786
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