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 06/11/2026, the claims and specification were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the specification, the objection to the specification is withdrawn by the Office.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(b) of claims 12-14 as failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention, the rejection under 35 U.S.C. 102 of claims 1-4, 6-11, 14-16, 18, and 25 as being anticipated by Huang et al. (WO 2023/273997 A1), and the rejections under 35 U.S.C. 103 of claims 17, 19-20, and 26-28 as being unpatentable over Huang as applied above, claims 1-12 and 14-28 as being unpatentable over Lee et al. (US 2017/0244047 A1) in view of Huang et al. (WO 2023/273997 A1), and claim 13 as being unpatentable over Lee and Huang above and further in view of Ha et al. (US 2020/0365814 A1), are withdrawn by the Office.
Claims 1-28 were originally filed.
Claims 29 and 30 have been added.
Claims 2 and 13 are canceled.
Claims 1, 3-12, and 14-28 are instantly amended.
Claims 1, 3-12, and 14-30 are pending in the application.
Response to Arguments
Applicant's arguments have been fully considered but they are not persuasive.
Examiner would like to thank Dr. Sawato for the data presented in the declaration dated 06/11/2026, which has been considered in its entirety and will be discussed herein.
Examiner acknowledges that Compound X demonstrates increased external quantum efficiency compared to Compound 2-56. Examiner also notes that the only difference between the two compounds is the instantly claimed quaterphenyl group bonded to the amine core in place of the terphenyl group in the comparative compound. However, Huang teaches that this exact modification results in higher current efficiency (paragraph 0170 and Table 1), which is a property related to external quantum efficiency. Thus, the observed increase in external quantum efficiency is not unexpected, but rather, a person having ordinary skill in the art prior to the effective filing date of the claimed invention would expect this modification to produce an increase in current efficiency, and concurrently, an increase in external quantum efficiency. For this same reason, the data in the specification is also not found to be evidence of unexpected results.
Further, as outlined in the rejection below, the compounds claimed by Applicant are anticipated by Huang et al. (WO 2023/273998 A1). Unexpected results cannot be present when the prior art anticipates the claimed invention. The court has held that when a claim is anticipated, unexpected properties are immaterial (See MPEP 2131.02, II).
Applicant’s remaining arguments have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Claim Rejections - 35 USC § 112
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.
Claims 11, 12, and 14 are 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.
With respect to claims 11, 12 and 14, the claims are dependent from “the compound of claim 2”, however, claim 2 is canceled. MPEP 2260.01 teaches us that if a base claim has been canceled, a claim which depends thereon should be rejected as indefinite.
For the purpose of examination, the claim will be interpreted as dependent from claim 1, as canceled claim 2 was previously dependent on claim 1.
Claim Rejections - 35 USC § 102
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 (i.e., changing from AIA to pre-AIA ) 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.
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.
Claims 1, 3, 6-12, 14-16, 18-19, 25, and 29-30 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Huang et al. (WO 2023/273998 A1, using the provided translation for references).
With respect to claims 1, 3, 10, 14-15, and 29-30, Huang discloses compound P16 (paragraph 0088), which is pictured below.
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This compound meets the requirements of condition (v) of instant formula (1) when Ar1 and Ar2 are represented by formula (1-e), n1 and m1 are 0 and R1A to R5A and R1B to R5B are not present, N* bonds to *b1, n2 and m2 are 0 and R11A to R15A and R11B to R15B are not present, *b2 bonds to N*, n3 and m3 are 0 and R21A to R25A and R21B to R25B are not present, *b3 bonds to *N, and R31 to R47 are each a hydrogen atom (protium).
Both of formula (1-e) are the same and in each, *e is a single bond to R116, X is CR1R2, R1 and R2 are each a C1 alkyl (methyl) group, and R111 to R115 and R117 to R118 are hydrogen atoms.
With respect to claims 6 and 7, Huang teaches the compound of claim 1, as discussed above.
Huang also teaches compound P60 (paragraph 0090), which is pictured below.
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This compound meets the requirements of condition (v) of parent formula (1) and of instant claim 6 when Ar1 and Ar2 are represented by formula (1-e), n1 is 0 and m1 is 1, R1A to R5A are hydrogen atoms and R1B to R5B are not present, N* bonds to *a1 and *b1 bonds to Ar1, n2 and m2 are 0 and R11A to R15A and R11B to R15B are not present, *b2 bonds to N*, n3 and m3 are 0 and R21A to R25A and R21B to R25B are not present, *b3 bonds to *N, and R31 to R47 are each a hydrogen atom.
Both of formula (1-e) are the same and in each, *e is a single bond to R116, X is CR1R2, R1 and R2 are each a C1 alkyl (methyl) group, and R111 to R115 and R117 to R118 are hydrogen atoms.
This compound also meets the requirements of instant claim 7 when n1 is 0 and m1 is 0, R1A to R5A and R1B to R5B are not present, n2 is 0 and m2 is 1, R11A to R15A are hydrogen atoms and R11B to R15B are not present.
With respect to claims 8 and 9, Huang teaches the compound of claim 1, as discussed above.
Huang also teaches compounds P35 and P39 (paragraph 0089), which are pictured below. Compound 35 meets the requirements of instant claim 8 and compound 39 meets the requirements of instant claim 9.
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With respect to claim 11, Huang teaches the compound of claim 1, and formula (1-a) is absent.
With respect to claim 12, Huang teaches the compound of claim 1, and formula (1-b) is absent.
With respect to claim 16, Huang teaches compound P16 of claim 1, as discussed above.
Huang also teaches Example 2 in Table 2 (paragraph 0215), which comprises compound P16, which is pictured and was discussed above, as a material in an organic electroluminescent device (paragraphs 0206-0207 and 0213).
With respect to claims 18 and 19, Huang teaches the compound of claim 1, as discussed above.
Huang also teaches Example 2 in Table 2 (paragraph 0215), which comprises compound P16, which is pictured and discussed above, as a material in an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the electrodes comprising a light emitting layer and the organic layer between the anode and light emitting layer (hole transporting zone) comprises the compound (paragraphs 0206-0207 and 0213).
With respect to claim 25, Huang teaches the device of claim 18 and the light emitting layer is a single layer (paragraphs 0206-0207 and 0213).
Claim Rejections - 35 USC § 103
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 (i.e., changing from AIA to pre-AIA ) 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.
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 17, 20, and 26-28 are rejected under 35 U.S.C. 103 as being unpatentable over Huang et al. (WO 2023/273998 A1, using the provided translation for references) as applied above.
With respect to claim 17, Huang teaches the material of claim 16, and Huang also teaches that the compound is suitable for use as a hole transporting material (paragraph 0128).
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 as a hole transporting material in a hole transporting layer, as taught by Huang.
With respect to claims 20 and 21, Huang teaches the device of claim 19, and Huang also teaches that the device may comprise a multilayer structure comprising at least one hole transport layer and the hole transport region may comprise the compound (paragraphs 0133-0134).
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 include at least one hole transport layer and include the compound in the at least one hole transport layer, as taught by Huang.
With respect to claim 22, Huang teaches the device of claim 20, and Huang also teaches that the hole transporting region may comprise a hole injection layer, a hole transport layer, and an electron barrier layer (a second hole transport layer), wherein the electron barrier layer is located between the hole transport layer and light-emitting layer (paragraph 0138), and preferably the electron barrier layer, which is directly adjacent to the light-emitting layer, comprises the compound (paragraph 0131).
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 include the compound in a hole transport layer directly adjacent to the light-emitting layer, as taught by Huang.
With respect to claim 23, Huang teaches the device of claim 20, and Huang also teaches that when the hole transport layer is 60 nm, and the electron barrier layer (second hole transporting layer) is 35 nm, the resulting electroluminescent device exhibits superior luminous efficiency and lower driving voltage.
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 a first and second hole transport layer with a combined thickness of 95 nm in order to obtain an electroluminescent device exhibits superior luminous efficiency and lower driving voltage, as taught by Huang.
With respect to claim 24, Huang teaches the device of claim 20, and Huang also teaches the preparation of an organic electroluminescent device wherein compound HT-4 is used in a layer analogous to the instantly claimed first hole transporting layer (paragraph 0206). Compound HT-4 is pictured below to facilitate discussion.
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Compound HT-4 meets the requirements of instant formula (22) when LA2, LB2, LC2, and LD2 are all a 6-membered arylene (phenylene), k is 2, LE2 is also a 6-membered arylene (phenylene), and A2, B2, C2, and D2 are all a 6-membered aryl (phenyl) group.
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 a compound of formula (22) in the first hole transport layer, as demonstrated by Huang.
With respect to claims 26 and 27, Huang teaches the device of claim 18, and Huang also teaches that the light emitting layer may comprise a fluorescent dopant, such as BFD-8 (paragraph 0149), which is pictured below. It is examiner’s position that BFD is an obvious abbreviation for “blue fluorescent dopant”.
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Examiner is interpreting this compound to meet the requirements of the instant claims through its very close structural similarity to the blue fluorescent dopant BD-1, as given on page 310 of the instant specification. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. When compounds are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II.
Huang is silent to the emissive wavelength of the blue dopant. However, this is considered to be a property of the composition. Support for this presumption comes from the use of like materials and like processes when BFD-8 is used as a blue dopant in the emissive layer of an electroluminescent device, which would result in the claimed property described in the instant claims. Therefore, the claims are considered to be obvious over Huang, and the burden shifts to applicant to show that there is an unobvious difference between the claimed emissive wavelength range of 500 nm and less and the wavelength of the compound in the prior art, BFD-8. See MPEP 2112 (V). In addition, the presently claimed properties are considered to be present once the work of Huang was first provided. See MPEP 2112.01 (II).
With respect to claim 28, Huang teaches the device of claim 18, and Huang also teaches that organic electroluminescent devices can be used in electronic devices such as lighting elements and organic thin-film transistors (paragraph 0129).
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 claimed organic electroluminescent device in an electronic device, as taught by Huang.
Allowable Subject Matter
Claims 4 and 5 are 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.
The following is a statement of reasons for the indication of allowable subject matter:
With respect to claims 4 and 5, both claims require a compound of claim 1, wherein one of Ar1 and Ar2 has the formula of (1-a) or (1-b).
A search of the prior art did not identify the claimed invention.
The closest identified prior art is Huang et al. (WO 2023/273998 A1, using the provided translation for references).
With respect to dependent claims 4 and 5, Huang discloses a monoamine compound with better flatness making it easier to form amorphous films, reduce crystallinity, and make the spatial structure of the compound more dense. This is accomplished using a specific quaterphenyl substituent on the amine core. The compounds taught by Huang require at least one tricyclic substituent analogous to instant formula (1-e), which is bonded directly to the amine core.
Instant independent claim 1 requires that when one of Ar1 and Ar2 is a moiety of formula (1-a) then the other of Ar1 and Ar2 is a moiety of formulae (1-a), (1-b), or (1-e). As Huang requires at least one tricyclic substituent analogous to instant formula (1-e) is bonded directly to the amine core, Huang cannot teach a compound wherein one of Ar1 and Ar2 is a moiety of formula (1-a) then the other of Ar1 and Ar2 is a moiety of formulae (1-a) or (1-b). Furthermore, instant independent claim 1 requires that when one of Ar1 and Ar2 is a moiety of formula (1-a) and the other one of Ar1 and Ar2 is a moiety of (1-e), then formula (1-e) does not directly bond to the central nitrogen atom. As Huang requires at least one tricyclic substituent analogous to instant formula (1-e) is bonded directly to the amine core, Huang cannot teach a compound wherein one of Ar1 and Ar2 is a moiety of formula (1-a), and the other of Ar1 and Ar2 is a moiety of formulae (1-e) which does not directly bond to the central nitrogen atom.
Instant independent claim 1 also requires that when one of Ar1 and Ar2 is a moiety of formula (1-b) then the other of Ar1 and Ar2 is a moiety of formulae (1-a). As Huang requires a compound comprising at least one moiety of formula (1-e), Huang cannot teach a compound wherein one of Ar1 and Ar2 is a moiety of formula (1-b) and the other of Ar1 and Ar2 is a moiety of formula (1-a).
Additionally, there existed no teaching nor motivation to make such a modification in the broader prior art as of the effective filing date of the claimed invention.
Conclusion
Applicant's amendment necessitated any 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 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/Primary Examiner, Art Unit 1786
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