DETAILED ACTION
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 Amendment
In the response filed 04/28/2026, the claims were amended, and supplemental copies of the specification and abstract were submitted.
These amendments are hereby entered.
In light of Applicant’s amendments to the specification, the objection to the specification is withdrawn by the Office.
Claims 1-25 were originally filed.
No claims have been added, canceled, or withdrawn.
Claims 1, 16, and 19 are instantly amended.
Claims 1-25 are pending in the application.
Response to Arguments
Applicant's arguments filed 04/28/2026 have been fully considered but they are not persuasive.
At the outset, please be advised that any experimental or theoretical data that Applicant wishes to be considered must either be present in the original, as-filed specification, or submitted in the form of a declaration. For the purpose of continuing examination, the data submitted for CX-1 and CX-2 will be discussed, but should the data lead to any claims being found to be allowable, the application cannot go to patent until the data is resubmitted in a declaration.
Examiner thanks Applicant for submitting data on comparative compounds CX-1 and CX-2, however, this data is not sufficient to overcome the rejections of record for at least the following reasons.
First, it is noted that applicant has only provided data from one trial of each compound from a single device structure. There is not enough evidence to support Applicant’s assertion that that these same results would be observed over a statistical analysis of multiple trials and multiple device structures. Without a statement of standard deviation, it is unclear whether these data represent a statistically significant improvement over the comparison devices or whether these data fall within standard deviation.
Second, the data presented are not commensurate in scope with claims drawn to a compound only, such as claims 19-25, because the data are drawn to properties that result from the compound in a device. A person having ordinary skill in the art would recognize that common endeavors in the field of organic electroluminescent devices, such as improved luminance, external quantum efficiency, device lifetime, color purity, and driving voltage, can be influenced by a multitude of factors such as device layer order, layer thickness, as well as layer composition. There is not enough evidence to support Applicant’s assertion that the claimed improvements are the result of the claimed compound only, and would be observed in any device of any structure.
Third, the data presented are not commensurate in scope with the claimed invention because data have only been presented for a narrow scope of the broad genus encompassed by the independent claims. The independent claims currently encompass variables with a significant number of possible functional groups, such as any substituted or unsubstituted C6-C60 aryl group and any C2-C60 heteroaryl (see for example the definition of R10). Similarity, the claims encompass variables which could be reasonably expected to confer different chemical properties, for which no data have been presented (see for example, the definitions of X1 and X2 which can be an oxygen or sulfur atom). These variables surely represent thousands of diverse compounds while data for only a few similar compounds have been presented.
Fourth, the prior art of Min teaches that compounds comprising a triphenylene group at a position analogous to instant R10 provide a compound with a high extinction coefficient (paragraph 0028). It is examiner’s position that improved service life, decrease in roll-off, and increased device lifetime are expected beneficial results of incorporating a compound with high extinction coefficient and actually represent evidence of obviousness rather than evidence of nonobviousness (MPEP 716.02(c)(II)).
For at least these reasons, while compounds X1 through X7 and CX-1 and CX-2 appear to have long service life characteristics, as noted by applicant, it is unclear whether these data represent a statistically significant improvement, whether these same results would be realized in any device, whether the full breadth of the claimed compounds would demonstrate these same advantageous properties, and whether the observed improvements are actually anticipated by the prior art.
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.
Claims 1-15 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2020/0235303 A1, herein after referred to as Kim 2020) and further in view of Min et al. (WO 2022/078429 A1, using US 2023/0299242 A1 as an official translation and for references) and Kim et al. (US 2022/0093878 A1, herein after referred to as Kim 2022).
With respect to claim 1, Kim 2020 discloses a light emitting element comprising a first electrode (an anode), a second electrode (a cathode), and an organic layer (a functional layer) between the electrodes (paragraph 0219) comprising a first, second and third compound (paragraph 0218).
The first compound may be represented by compound 101, which is pictured below (paragraph 0199).
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This compound is analogous to the instant second compound and meets the requirements of instant Formula HT-1 when R14 is a substituted aryl group having 6 ring forming carbon atoms, and n5 is 0 so that R15 is not present.
Kim 2020 also teaches the second compound may be represented by compound 2-1 (paragraph 0200), which is pictured below.
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This compound is analogous to the instant third compound and meets the requirements of instant Formula ET-1 when b1 is 1 and L1 is a substituted arylene having 6 ring-forming carbon atoms, b2 is 0 and L2 is not present and b3 is 0 and L3 is not present, Ar1 is a aryl group with 14 ring-forming carbon atoms and Ar2 and Ar3 are an aryl having 6 ring forming carbon atoms and Y1 through Y3 are nitrogen atoms.
Kim 2020 also teaches that the third compound is a boron-containing compound such as compound 3-15 (page 36), which is pictured below.
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This compound is analogous to the instant first compound.
This compound is derived from Kim 2020 formula 3 (page 4), which is pictured below.
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Kim also teaches that X31 is boron, X32 and X33 are N(R34) (paragraph 0106, and that R34 may be triphenylene (paragraph 0192, lines 2-3).
Such a modification produces a compound that meets the requirements of instant Formula 1 when X1 and X2 are each N(R10), R3 and R8 are an unsubstituted heteroaryl group of 12 ring-forming carbon atoms (9-carbazolyl), both of R10 are represented by Formula 2, and all other R groups are hydrogen atoms. In Formula 2, n2-n4 are 0 and R11-R13 are not present.
Kim 2020 includes each element claimed, with the only difference between the claimed invention and Kim 2020 being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a composition which, when used in an organic light emitting device, results in improved efficiency and lifespan (paragraph 0217), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Kim 2020 does not teach nor fairly suggest selection of a triphenylene group at a position analogous to instant R10.
In analogous art, Min teaches a boron-containing polycyclic compound for use in an organic light emitting device (paragraph 0024 and chemical formula (1))
Min teaches that in a preferred embodiment of the invention, a position analogous to instant R10 is substituted by a triphenylene group (paragraph 0049 and page 6).
Min teaches that the compounds of the invention possess a narrow emission peak, thereby providing high color purity (paragraphs 0024 and 0003)
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to preferentially select a triphenylene substituent for the compound of Kim 2020 in order to obtain a compound with a narrow emission peak, thereby providing high color purity, as taught by Min.
However, neither Kim 2020 nor Min teach a fourth compound represented by Formula M-b.
In analogous art, Kim 2022 teaches an organic light emitting device with an emission layer comprising a host, an emitter, and a sensitizer.
Kim 2022 teaches that when a sensitizer is used in the emission layer, triplet excitons formed at a host are transferred to a sensitizer through Dexter energy transfer, and energy of singlet excitons formed at the host are transferred to singlet and triplet of the sensitizer, wherein the singlet undergoes intersystem crossing into a triplet, and then the triplet energy of the sensitizer is transferred to an emitter through Förster energy transfer. Accordingly, all the singlet excitons and the triplet excitons generated in the emission layer are transferred to an emitter, and an organic light emitting device having improved efficiency and improved lifespan characteristics is obtained (paragraph 0036).
Kim 2022 gives an example of a suitable sensitizer in the compounds below (page 462).
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This compound is analogous to the instant fourth compound and meets the requirements of instant Formula M-b when Q1, Q3 and Q4 are carbon atoms and Q2 is a nitrogen atom, C1 is a substituted heteroaryl group having 5 ring-forming carbon atoms, C2 and C3 are a hydrocarbon ring group having 6 ring-forming carbon atoms, C4 is a heteroaryl group having 5 ring-forming carbon atoms, e1 is 1 and L21 is a direct linkage, e2 is 1 and L22 is an oxygen atom, e3 is 1 and L23 is N(R37), e4 is 0 and L24 is not present, d1 is 3 and two R31 are joined to form a fused ring and one R31 is a aryl group having 6 ring-forming carbon atoms, d2 is 0 and R32 is not present, d3 is 0 and R33 is not present, R37 is an aryl group having 6-ring forming carbon atoms that is fused with ring C3 to form a carbazole moiety, d4 I 1 and R34 is a alkyl group having 4 carbon atoms.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the sensitizer of Kim 2022 in the emission layer of Kim 2020 in order to obtain an organic light emitting device having improved efficiency and improved lifespan characteristics, as taught by Kim 2022.
With respect to claim 2, Kim 2020, Min and Kim 2022 teach the light emitting element of claim 1, and Kim 2020 teaches that the organic layer comprises an emission layer, a hole transport layer between the first electrode and the emission layer and an electron transport layer between the second electrode and the emission layer (paragraph 0219) and the emission layer comprises the composition (paragraph 0218). Similarly, Kim 2022 teaches the sensitizer is for use in the emission layer (abstract).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the composition of Kim 2020, Min, and Kim 2022 in the emission layer of a device with the claimed structure, as taught by Kim 2020 and Kim 2022.
With respect to claim 3, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1, and the first compound is represented by Formula 1-2, as pictured and discussed above.
With respect to claim 4, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 3, and the compound of Formula 1-1 is represented by Formula 1-1a, as pictured and discussed above.
With respect to claim 5, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 3, as discussed above.
However, neither Kim 2020 nor Min teach the first compound is represented by instant Formula 1-2a to 1-2e.
Kim 2022 teaches an emitter which is a boron compound which is analogous to the boron compound of Kim 2020 and Min in Formula 1-1 (paragraph 0196), which is pictured below.
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Kim teaches that the emitter compound may also be represented by Formula 1-2 (paragraph 196), which is pictured below.
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Kim 2022 teaches that the emitter compounds of the invention demonstrate an increased horizontal orientation ratio which results in an improvement in lifespan and efficiency of an organic light-emitting device (paragraph 0357-0358).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate the boron emitter of Kim 2022 into the device of Kim 2020 and Min in order to obtain a compound with improved horizontal orientation ratio and a device with improved lifespan and efficiency, as taught by Kim 2022. It would similarly have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to modify the compound of Kim 2022 in the same manner taught by Min in order to obtain a compound with a narrow emission peak, thereby providing high color purity, as taught by Min.
Such a compound meets the requirements of instant Formula 1-2a.
With respect to claim 6, Kim 2020, Min and Kim 2022 teach the light emitting element of claim 1, and the first compound represented by Formula 1 is represented by Formula 1-3, as pictured and discussed above.
With respect to claim 7, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1, and the group represented by Formula 2 is represented by Formula 2-1, as pictured above.
With respect to claim 8, Kim 2020, Min, and Kim 2022 teaches the light emitting element of claim 1, and R1 is a hydrogen atom, as discussed above.
With respect to claim 9, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1, and R2, R5, R6, and R9 are each hydrogen atoms, as discussed above.
With respect to claim 10, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1, and R4 and R7 are each hydrogen atoms, and R3 and R8 are an unsubstituted heteroaryl group of 12 ring-forming carbon atoms (9-carbazolyl) as discussed above.
With respect to claim 11, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1, and each R10 is a triphenylenyl group, as discussed above.
With respect to claim 12, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1, and R11, R12, and R13 are not present, as discussed above.
With respect to claim 13, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1, and Kim 2020 teaches that the emission layer comprises the composition (paragraph 0218).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the first, second, and third compounds in the emission layer, as taught by Kim 2020.
With respect to claim 14, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1 and Kim 2020 teaches that the emission layer comprises the composition (paragraph 0218). Similarly, Kim 2022 teaches the sensitizer is for use in the emission layer (abstract).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the composition in the emission layer as taught by Kim 2020 and Kim 2022.
With respect to claim 15, Kim 2020, Min, and Kim 2022 teach the light emitting element of claim 1, and the first compound is identical to instant compound 4, as discussed above.
Claims 16-18 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2022/0093878 A1) and further in view of Min et al. (WO 2022/078429 A1, using US 2023/0299242 A1 as an official translation and for references).
With respect to claim 16, Kim discloses a light emitting element comprising a first electrode (an anode) a second electrode (a cathode), and an emission layer between the electrodes (paragraph 0004) comprising a emitter of Formula 1 (paragraph 0170), which may be represented by Formula 1-1 (paragraph 0205), which is pictured below.
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In this formula, X12 is NR15 (paragraph 0198), X13 is NR16 (paragraph 0199), b13 is 0 and R13 is not present, b11 and b12 are each 1 (paragraph 0203), and R11 and R12 are each a C12 heteroaryl group (paragraph 0202) such as carbazolyl (paragraph 0329), and R15 and R16 are each a C18 aryl group (paragraph 0202).
Such a modification produces a compound that meets the requirements of instant Formula 1 when X1 and X2 are each N(R10), R3 and R8 are an unsubstituted heteroaryl group of 12 ring-forming carbon atoms (9-carbazolyl), both of R10 are represented by Formula 2, and all other R groups are hydrogen atoms. In Formula 2, n2-n4 are 0 and R11-R13 are not present.
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a composition which, when used in an organic light emitting device, results in improved efficiency and lifespan (paragraph 0217), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Kim does not teach nor fairly suggest selection of a triphenylene group at a position analogous to instant R10.
In analogous art, Min teaches a boron-containing polycyclic compound for use in an organic light emitting device (paragraph 0024 and chemical formula (1))
Min teaches that in a preferred embodiment of the invention, a position analogous to instant R10 is substituted by a triphenylene group (paragraph 0049 and page 6).
Min teaches that the compounds of the invention possess a narrow emission peak, thereby providing high color purity (paragraphs 0024 and 0003)
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to preferentially select a triphenylene substituent for the compound of Kim 2020 in order to obtain a compound with a narrow emission peak, thereby providing high color purity, as taught by Min.
With respect to claim 17, Kim and Min teach the light emitting element of claim 16, and the polycyclic compound is represented by Formula 1-1, as pictured and discussed above.
With respect to claim 18, Kim and Min teach the light emitting element of claim 16, and the group represented by Formula 2 is represented by Formula 2-1, as pictured above.
Claims 19-25 are rejected under 35 U.S.C. 103 as being unpatentable over Fleetham et al. (US 2022/0149294 A1).
With respect to claim 19, Fleetham discloses the compound below (page 11).
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This compound is derived from the Fleetham formula below (paragraph 0079).
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Fleetham also teaches that RA and RB are heteroaryl (paragraph 0086) such as carbazole (paragraph 0043, line 20).
Such a modification produces a compound that meets the requirements of instant Formula 1 when X1 and X2 are each N(R10), R3 and R8 are an unsubstituted heteroaryl group of 12 ring-forming carbon atoms (9-carbazolyl), both of R10 are represented by Formula 2, and all other R groups are hydrogen atoms. In Formula 2, n2-n4 are 0 and R11-R13 are not present.
Fleetham includes each element claimed, with the only difference between the claimed invention and Fleetham being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound capable of functioning as a thermally activated delayed fluorescent (TADF) emitter in an OLED at room temperature (paragraph 0006) commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound of Fleetham in an light emitting element with the claimed structure in order to obtain a device with longer device lifetime (paragraph 0178), as taught by Fleetham.
With respect to claim 20, Fleetham teaches the compound of claim 19, and the polycyclic compound is represented by Formula 1-1, as pictured and discussed above.
With respect to claim 21, Fleetham teaches the compound of claim 20 and the compound is represented by Formula 1-1a, as pictured and discussed above.
With respect to claim 22, Fleetham teaches the compound of claim 20, as discussed above.
Fleetham also teaches that the compound may be represented by the formula below (paragraph 0079).
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In this formula, Y1 through Y4 may all be NR (paragraphs 0079 and 0084).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention use either embodiment of the boron emitter of Fleetham in a device of the instant claims in order to obtain a compound capable of functioning as a thermally activated delayed fluorescent (TADF) emitter in an OLED at room temperature (paragraph 0006) and a device with longer device lifetime (paragraph 0178), as taught by Fleetham.
Such a compound meets the requirements of instant Formula 1-2a.
With respect to claim 23, Fleetham teaches the compound of claim 19, and the polycyclic compound is represented by Formula 1-3, as pictured and discussed above.
With respect to claim 24, Fleetham teaches the compound of claim 19, and the group represented by Formula2 is represented by Formula 2-1, as pictured above.
With respect to claim 25, Fleetham teaches the compound of claim 19, and the compound is identical to instant Compound 4, as discussed above.
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 RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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.
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/RACHEL SIMBANA/Examiner, Art Unit 1786
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