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 .
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 11/25/2025 has been entered.
Claims 1-20 are pending as amended on 11/25/2025. Claims 9, 10, 18 and 19 stand withdrawn from consideration.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claim Objections
Claims 12 and 20 are objected to because of the following informalities: The resolution of the chemical structures is too low. The resolution must be improved to provide sharper images in subsequent claim submission. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 12 and 20 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claims 1 and 13 have been amended to recite several provisos which must be satisfied. Claims 12 and 20 fail to further limit claims 1 and 13, respectively, because they recite compounds which fail to satisfy at least one proviso recited in the independent claim:
compounds 9, 12, 20: if L1 is formula 2, L4 is H and Ar1 is phenyl, then Ar2 is not permitted to be naphthyl;
compound 108: if L4 is formula 2, L1 is H and Ar1 is phenyl, then Ar2 is not permitted to be phenyl.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 103
Claim(s) 1-4, 6, 13 and 14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Cui et al (CN 110950763A; original and previously included machine translation cited herein).
As to claims 13 and 14, Cui discloses a spirobenzanthrone derivative according to formula II, which is suitable for organic electroluminescent devices (see translation [0002] and original document [0020]):
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As shown in the generic formula II, the “m” and “n” substituents have a variable attachment position to a benzene ring within the spirobenzanthrone structure (four possible attachment positions).
As an example compound, Cui discloses:
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Compound 190 has a structure according to generic formula II wherein n is zero and m is 1.
The compound 190 exemplified by Cui has a structure according to instant formula 1 recited in claim 13 except that the arylamine group according to instant formula 2 within Cui’s compound is attached at a position on a benzene ring adjacent to instant position L2 (position corresponding to instant L2 is shown with arrow below):
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Given that the “m” substituent in Cui’s formula II is shown as having a variable attachment position (i.e., four possible attachment positions), the person having ordinary skill in the art would have been motivated to prepare a compound according to Cui’s formula II wherein “n” is zero and “m" is 1, and wherein Ar1 and Ar2 are each N-phenyl carbazolyl, having any of the four possible attachment positions of the “m” substituent in order to provide a compound exhibiting high luminous efficiency, long life, and low driving voltage [0009]. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a position isomer of Cui’s compound 190 which has the “m” substituent attached to any of the three other carbons of the benzene ring, including a position isomer wherein the “m” substituent is attached at the adjacent ring position (corresponding to instant position L2). The suggested compound has a structure according to formula 1 recited in claim 13 and formula 3-2 recited in claim 14, wherein instant Ar1 is phenyl and instant Ar2 is N-phenyl carbazolyl.
As to claims 1-4 and 6, Cui suggests a compound according to claims 13 and 14, as set forth above. Cui further discloses a device (see [0066-75]) comprising an anode [0067], a cathode [0075] (corresponding to the presently recited electrodes) and an organic layer between the electrodes [0068-74]. Cui discloses a hole transport region (comprising a hole injection layer on the first electrode, a hole transport layer on the hole injection layer, and an electron blocking layer on the hole transport layer) on the first electrode [0068-70], an emission layer on the hole transport region [0071], and an electron transport region on the emission layer [0072-74]. See also [0148] and [0149]. Cui teaches that at least one organic layer comprises the spirobenzanthrone derivative, and that the layer can be a hole injection layer, hole transport layer or electron blocking layer [0051-52, 0054].
Claim(s) 1-8, 12-17 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al (US 2014/0117329) in view of Jung et al (CN 106699573A; included machine translation cited herein).
This is a rejection of compound 54 (and devices comprising instant compound 54), which is recited in claims 12 and 20. Compound 54 is encompassed by the chemical formulas in the generic claims.
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As to claims 13-17 and 20, Lee discloses an amine-based compound according to the following formula [0022]:
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In the formula above, the subscripts “a” and “b” may be zero [0034] (see also narrower formulas 1A(1) and 1B(1) in [0042], which have structures according to formula 1 wherein “a” and “b” are zero). Lee names several examples of suitable R1 and R2 groups in [0036], and several examples of suitable L3 groups in [0030].
Lee exemplifies various compounds according to the generic disclosed Formula 1 in [0045], including compounds 8 and 32 (copied below), wherein the group corresponding to R1 is naphthyl and the group corresponding to -(L3)c-R2 is phenyl:
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Lee teaches that in formula 1, Ar1 and Ar2 may be a phenyl group, a naphthyl group or an anthryl group [0025], they may differ from each other [0027], and they may be optionally linked to each other via a single bond [0023]. As shown above (see compounds 8 and 32), Lee exemplifies compounds wherein Ar1 and Ar2 unlinked phenyl groups (compound 8), and compounds wherein Ar1 and Ar2 are phenyl groups linked via single bond (compound 32).
Lee teaches that the compound may be used in at least one of a hole injection layer or a hole transport layer [0049], and further teaches that since the Ar1 and Ar2 substituents are aryl groups, the amine-based compound may have improved thermal stability [0046]. However, Lee fails to exemplify a compound wherein Ar1 is phenyl and Ar2 is naphthyl, and wherein the phenyl and naphthyl groups are linked via single bond to form a spiro structure as shown below:
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Jung teaches that a substance used for organic electroluminescent device preferably has excellent thermal stability, and that use of substances having a low Tg results in crystallization and a reduction of light emission efficiency (p 33, first paragraph). Jung further teaches that it is necessary to smoothly transfer holes or electrons injected into the device to the light emitting layer and to prevent the injected holes from escaping outside the light emitting layer, and therefore, a substance should have an appropriate band gap and HOMO or LUMO (p 33, second paragraph).
Jung teaches a spiro organic compound which can suitably be used as an electron blocking substance or a hole transporting substance for providing a low-power high-efficiency OLED (p 33, “disclosure of invention”). The compound is designed using a spiro(benzo[de]anthracene-7,9’-fluorene core (p 36, top), and can be used in a hole transport layer or an electron blocking layer (p 36, middle). Jung discloses several examples of compounds wherein the spiro core is attached to an arylamine substituent having various structures (see compounds starting on p 37), including arylamine substituents containing a carbazole group (see, e.g., compounds 30-32 on p 38). Jung teaches that compared with other spiro structures, the compound can greatly improve glass transition temperature due to the large molecular weight of the spiro nucleus. Jung further teaches that by changing the amine substituents on the disubstituted amine group, the energy level of the HOMO can be changed in various ways (p 70, middle).
Considering Jung’s disclosure, the person having ordinary skill in the art would have been motivated to select phenyl and naphthyl as Lee’s Ar1 and Ar2 groups, and, to have linked the phenyl and naphthyl groups via single bond to form a spiro(benzo[de]anthracene-7,9’-fluorene moiety, in order to provide a compound as taught by Lee which has a high glass transition temperature, and suitability for use as an electron blocking substance or a hole transporting substance for providing a low-power high-efficiency OLED. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a compound according to Lee’s general formula 1 wherein a and b are zero, R1 is naphthyl, and -(L3)c-R2 is phenyl, such as shown in Lee’s example compounds 8 and 32, and wherein Ar1 and Ar2 are linked phenyl and naphthyl groups such that, together with the fluorene to which they are attached, the groups form a spiro(benzo[de]anthracene-7,9’-fluorene moiety as taught by Jung, thereby arriving at a compound having a structure according to instant compound 54.
As to claims 1-3, 5-8 and 12, modified Lee suggests a compound according to claims 13-17 and 20, as set forth above. As to the device structure recited in claims 2 and 4, Lee discloses an OLED device comprising first and second electrodes [0059], [0097], and an organic layer between the electrodes [0060], wherein the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, an emission layer, and an electron transport layer [0053, 0061]. Lee teaches that the compound may be used in a hole injection layer or hole transport layer [0049].
As to claim 4, modified Lee suggests a device according to claims 2 and 3, as set forth above. As discussed above, Lee teaches an OLED device comprising hole injection, hole transport and electron blocking layers, and teaches the use of the disclosed compound in hole injection and hole transport layers. Lee fails to specifically teach that the compound could be used in an electron blocking layer, as recited in claim 4. However, Jung discloses an OLED device structure similar to the structure taught by Lee, wherein an organic material layer comprises a hole injection layer, hole transport layer, electron blocking layer, light emitting layer, and electron transport layer (p 69). Jung discloses that the aromatic amine compound can be used in an electron blocking layer and/or hole transport layer (p 69). In light of Jung’s disclosure, one having ordinary skill in the art would have recognized that an aromatic amine compound suitable for use in the hole transport layer of an OLED would also be suited for use in additional layers of the OLED, including an electron blocking layer. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed an OLED device having a hole injection, hole transport and electron blocking layers, as suggested by modified Lee, by including the aromatic amine compound in any one or more of the layers in the hole transport region, including in the electron blocking layer as recited in claim 4, in order to satisfy conditions required for each organic material layer.
Claim(s) 11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al (US 2014/0117329) in view of Jung et al (CN 106699573A; included machine translation cited herein), and further in view of Zhang et al (Blue and white organic electroluminescent devices based on 9,10-bis(2′-naphthyl)anthracene, Chemical Physics Letters 369 (2003) 478–482).
The rejection of claims 1 and 2 over Lee in view Jung is incorporated here by reference. Modified Lee suggests a device according to claim 2, as set forth above. Lee teaches that the emission layer may include a host and a dopant [0079], and may be a blue emission layer [0080]. However, Lee fails to teach that the emission layer comprises a compound according to formula E-1 recited in claim 11.
Zhang discloses BNA
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as an emitting host in OLEDs (p 479, lower left). Zhang teaches that BNA forms stable and smooth films with bright blue emission and was shown to be a good host emitting material for OLED applications (p 482). BNA has a structure corresponding to the elected species of instant formula E-1 (i.e., instant compound E-2). Considering Zhang’s disclosure, it would have been obvious to the person having ordinary skill in the art to have used BNA as a host material in the emission layer of the OLED of modified Lee in order to provide a stable smooth film with bright blue emission.
Response to Arguments
Applicant's arguments filed 11/25/25 have been fully considered.
The examiner agrees with Applicant’s arguments that, in view of the amendments to the claims, the previously set forth rejections have been overcome. However, in view of the new rejections above, the claims are not in condition for allowance.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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/RACHEL KAHN/Primary Examiner, Art Unit 1766
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