DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
This office action is in response to applicant’s Restriction/Election filed on 05/15/2026.
Currently claims 1-28 are pending in the application.
Election/Restrictions
Applicant's election without traverse of Group I, claims 1-23, in the reply filed on 05/15/2026 is acknowledged.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 10/17/2023 and 06/16/2025 were filed before the mailing date of the office action. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements were considered by the examiner.
Claim Rejections - 35 USC § 112 (b)
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.
Claims 12, 14, 16 and 21 are rejected under 35 U.S.C. 112 (b), as being indefinite for failing to particularly pointing out and distinctly claim the subject matter which the inventor or a joint inventor, regard as their invention.
Regarding claims 12, 14 and 16, each claim recites “the metal atom” (claim 12, line 2; claim 14, line 2; claim 16, line 2). There is insufficient antecedent basis for this limitation in the claims. Claim 12 depends from claim 11, claim 14 depends from claim 13, and claim 16 depends from claim 15, and each of claims 11, 13 and 15 depends from claim 1; none of claims 1, 11, 13 or 15 previously recites a “metal atom.” The “metal atom” is first introduced only in claim 9, from which claims 12, 14 and 16 do not depend. It is therefore unclear whether “the metal atom” is recalling the metal atom of claim 9 or introducing a new element, rendering the claims indefinite. Clarification and/or correction are/is required. For the purpose of examination, the claim will be interpreted according to the specification, and the examiner shall consider “the metal atom” to be “a metal atom of a cathode layer bonded to the ring-opening reaction product,” consistent with claim 9 and paragraphs [0011]–[0014] and [0091]–[0097].
Regarding claim 21, the instant claim recites “the surface layer is a monolayer or a bilayer” (claim 21, line 2). There is insufficient antecedent basis for “the surface layer” in the claim. Claim 21 depends from claim 1, which does not recite a “surface layer”; an “ETL surface layer” is first introduced in claims 8 and 10, from which claim 21 does not depend. It is unclear whether the “surface layer” is being recalled from claim 8/10 or a new “surface layer” is being introduced, rendering the claim indefinite. Clarification and/or correction are/is required. For the purpose of examination, the claim will be interpreted according to the specification, which describes a single surface layer of the ring-opening reaction product.
Allowable Subject Matter
Claims 1-11, 13, 15, 17-20, 22 and 23 are allowed. Claims 12, 14, 16 and 21 are rejected under 35 U.S.C. 112(b) as set forth above; these claims would be allowable if amended to overcome the antecedent-basis issues, as they otherwise define allowable subject matter.
The following is the examiner’s statement of reasons for allowance:
The closest prior art, CN 103642445 A (Zhang) discloses a surface-modified layer of an organic light-emitting diode ([0022] – [0028]); the composition comprises nano-silica particles having polar epoxy groups modified on the surface, and a modified layer comprising a reaction product [0064]–[0066]). Zhang modifies the surface with epoxy-functionalized silica particles, and therefore fails to teach or suggest, alone or in combination, a surface-modified electron transport layer of an OLED comprising a ring-opening reaction product between a nitrogen-containing heterocycle of the ETL and a three-membered ring, as required by claim 1.
Furthermore, US 2007/0231560 A1 (Zhang2) discloses, a surface-modified layer ([0076]) whose surface may be subjected to modifying surface treatments to facilitate adhesion to an adjacent surface, and a resin layer that may include a curable/cross-linkable oxirane (epoxy) resin, including epoxy resins produced by reaction of a hydroxyl-, carboxyl-, or amine-containing compound with epichlorohydrin ([0049]–[0052]). Zhang2 is directed to a thermal-management resin structure and, like CN 103642445 A, fails to teach or suggest a ring-opening reaction product between the nitrogen-containing heterocycle of an OLED ETL and an oxiranyl, aziridinyl, or thiiranyl ring.
Therefore, the prior art of record CN 103642445 A (Zhang) and US 2007/0231560 A1 (Zhang2), alone or in combination, and in combination with the other claimed features, fails to disclose, the limitation of independent claim 1: “the ETL comprising a ring-opening reaction product between a nitrogen-containing heterocycle of the ETL and one or more of an optionally substituted three-membered ring selected from the group consisting of an oxiranyl ring, an aziridinyl ring, and a thiiranyl ring”. Neither reference of record teaches or suggests this surface-localized, metal-anchoring ring-opening chemistry, and there is no proper rationale — absent impermissible hindsight reconstruction based on applicant’s own disclosure — to arrive at the claimed subject matter by combining the references of record. This determination is consistent with the Written Opinion of the International Searching Authority in parent PCT/US2021/039035, which found the corresponding subject matter novel and inventive over the same closest art.
Specifically, the aforementioned ‘the ETL comprising a ring-opening reaction product between a nitrogen-containing heterocycle of the ETL and one or more of an optionally substituted three-membered ring selected from the group consisting of an oxiranyl ring, an aziridinyl ring, and a thiiranyl ring,’ is material to the inventive concept of the application at hand to provide a thin, surface-localized chemistry that helps the cathode bond at the surface while limiting metal penetration into the ETL.
Dependent claims 2–11, 13, 15, 17–20, 22 and 23 are allowable at least by virtue of their dependence from allowable claim 1.
Examiner’s search note. The examiner considered the international search of record (ISA/US, PCT/US2021/039035) and further conducted a text search of the U.S. and foreign patent literature and of non-patent (scholarly) literature directed to OLED electron-transport-layer surface modification, ring-opening reactions of imidazole/phenanthroline heterocycles with oxiranyl/aziridinyl/thiiranyl rings, betaine-type surface functionalities, and cathode-interface metal-penetration barriers. No reference was located that teaches or suggests the surface ring-opening chemistry of claim 1 as applied to the nitrogen-containing heterocycle of an OLED ETL. US 2015/0060831 A1 (Ciszek) is noted as additional background: it teaches surface modification of an organic semiconductor by an addition reaction rather than a ring-opening of a nitrogen heterocycle, and likewise does not teach the claimed subject matter.
Examiner’s Note (Additional Prior Arts)
The examiner included a few prior arts which were not used in the rejection but are relevant to the disclosure.
US 2015/0060831 A1 (Ciszek) - Surface-modified organic semiconductors are disclosed. The surface-modified thin films comprising a first layer comprising a polyaromatic organic semiconductor and a surface layer in direct contact with the first layer, the surface layer comprising an addition reaction product of the polyaromatic organic semiconductor with, for example, a dienophile, wherein the first layer is substantially free of the addition reaction product of the organic semiconductor with the dienophile. Also provided are surface-modified single crystals comprising a core comprising a polyaromatic organic semiconductor and a coating in direct contact with the core, the coating comprising, for example, an addition reaction product of the polyaromatic organic semiconductor with a dienophile, wherein the core is substantially free of the addition reaction product of the organic semiconductor with the dienophile.
US 2023/0217675 A1 (Takenaka) - A light-emitting element is disclosed including an anode electrode, cathode electrode, an EML, and an HTL. The HTL includes a hole transport material, and a first polymer containing a polysiloxane bond in the main chain and having a functional group including a π-conjugated electron pair in a side chain of the first polymer.
US 2020/0161592 A1 (Shin) - An organic light-emission device is disclosed including a first electrode, a second electrode, and the light-emission layer interposed therebetween, wherein the light-emission layer contains a mesogenic polymer-based light-emission material and a chiral dopant, wherein the light-emission layer has one face facing the first electrode and an opposite face facing the second electrode, wherein molecules of the mesogenic polymer-based light-emission material in the one face are orientated in a first predetermined direction, while molecules of the mesogenic polymer-based light-emission material in the opposite face are orientated in a second predetermined direction different from the first predetermined direction, wherein an angle of the second predetermined direction relative to the first predetermined direction is defined as a twisted angle, and wherein molecules of the mesogenic polymer-based light-emission material are vertically arranged in a spirally twisted manner within the twisted angle between the one and opposite faces of the light-emission layer to form a twisted structure.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to S M SOHEL IMTIAZ whose telephone number is (408) 918-7566. The examiner can normally be reached on 8AM-5PM, M-F, PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Christine S. Kim can be reached at 571-272-8458. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/S M SOHEL IMTIAZ/Primary Patent Examiner
Art Unit 2812
07/29/2026
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