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 .
Claims 1-20 are pending as amended on 6/26/2026. Claims 9, 10, 18 and 19 stand withdrawn from consideration.
The previous action contained a rejection (over Cui) of compounds encompassed by the generic claims, as well as a rejection (over Lee in view of Jung) of a compound recited in claims 12 and 20 (compound 54). The previously examined compounds had structures according to instant formula I wherein L2 or L3 is a group represented by instant formula 2. The claims have been amended to no longer encompass the rejected compounds. Examination has therefore been extended to remaining recited species wherein L2 or L3 is a group represented by instant formula 2, in accordance with procedures in MPEP 803.02(III)(A).
The new grounds of rejection below were necessitated by Applicant’s amendment introducing additional provisos which further limit the independent claims in a manner not previously presented. Therefore, this action is properly made final.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn.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
Claim 1 is objected to because:
at the end of page 3, there is a proviso which states that if L3 is formula 2, Ar2 can be an unsubstituted phenyl group. In view of the newly added proviso which states that when L3 is Formula 2, Ar2 is not a phenyl group (see page 4, second added proviso), “unsubstituted phenyl group” should be deleted from the proviso in the last two lines on page 3;
on page 4, after the new provisos, there is a proviso for a case where L4 is a hydrogen atom, L1 or L2 is chemical formula 2, and Ar1 is a phenyl group. In this proviso, “or L2” should be deleted: in view of the first newly added proviso, Ar1 is not permitted to be a phenyl group when L2 is Formula 2;
in the last two lines, there is a proviso which limits Ar2 by excluding phenyl group when L3 is Formula 2. In view of the second newly added proviso, this is redundant.
Claim 13 is objected to for the same reasons set forth above for claim 1.
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
Claims 12 and 20 are 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.
Independent 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 40, 49, 57-59, 63-67 and 83-85. These compounds fail to satisfy provisos recited in the independent claims, which require that if L2 or L3 is formula 2, Ar2 must not be phenyl.
they recite compounds 50, 52, 55, 60-62, 68-70, 74-76, 80-82, 86, 87. These compounds fail to satisfy the provisos requiring that if L2 is formula 2, Ar1 is not permitted to be naphthyl or 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) 1-7 and 13-16 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).
As to claims 13-16, Lee discloses an amine-based compound according to Formula I taught in [0022]:
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which, more narrowly, can be a compound according to Formula 1A or 1B [0039], such as 1A(1) (wherein Ar1 and Ar2 in formula I are each phenyl groups) and 1B(1) (wherein Ar1 and Ar2 in formula I are each phenyl groups, are linked to each other via a single bond) disclosed in [0042]:
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In Lee’s Formulas above, R1 is considered to correspond to instant Ar1, while (L3)c-R2 is considered to correspond to instant Ar2. Lee teaches that R1 can be, e.g., anthryl, pyridinyl, pyrimidinyl, triazinyl and thiophenyl [0036], which are aryl or heteroaryl groups encompassed by the definition of Ar1 recited in instant claim 13, and, are groups which are not excluded by any presently recited proviso which applies when instant L2 or L3 is represented by instant Formula 2. Lee teaches that “c” can be 0 [0034], and that R2 can be, e.g., anthryl, pyridinyl, pyrimidinyl, triazinyl and thiophenyl [0036], which are aryl or heteroaryl groups encompassed by the definition of Ar2 recited in instant claim 13, and, are groups which are not excluded by any presently recited proviso which applies when instant L2 or L3 is represented by instant Formula 2.
Lee teaches that in the generic formula 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, Lee discloses formulas wherein Ar1 and Ar2 unlinked phenyl groups (Formula 1A(1)), and compounds wherein Ar1 and Ar2 are phenyl groups linked via single bond (Formula 1B(1)).
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 disclose 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, b and c are zero, R1 and R2 are independently selected from anthryl (which has 14 carbon atoms), pyridinyl, pyrimidinyl, triazinyl and thiophenyl [0036], and wherein Lee’s 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 Formula 1 wherein instant L2 or L3 is a group represented by instant Formula 2, as recited in instant claims 13, and further according to Formula 3-2 or 3-3 recited in claim 14, according to claim 15 (e.g., when anthryl or thiophenyl are selected to be Lee’s R1 and R2 groups), and, according to claim 16 (when anthryl is selected to be Lee’s R1 and R2 groups).
As to claims 1-3 and 5-7, modified Lee suggests a compound according to claims 13-16, as set forth above. As to the device structure recited in claims 2 and 3, 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 6/26/26 have been fully considered.
The claim objection has not been overcome, as the resolution of the chemical structures in claims 12 and 20 remains too low.
The examiner agrees with Applicant’s arguments that, in view of the amendments to the claims, the previously set forth rejections under 35 USC 103 have been overcome. However, in view of the new rejections above, the claims are not in condition for allowance.
Regarding claims 8 and 17:
Modified Lee suggests a compound according to instant formula I wherein instant L2 or L3 is a group represented by formula 2, as set forth above. Lee teaches several suitable groups for R1 and R2 in [0036], including phenyl and naphthyl. However, in view of the provisos recited in the independent claims, when L2 or L3 is represented by formula 2, instant Ar1 and Ar2 are not permitted to be phenyl or naphthyl. Therefore, modified Lee does not suggest a compound according to instant claims 8 and 17.
The examiner is unaware of prior art which discloses or suggests compounds that: (1) satisfy the provisos recited in the independent claims, (2) have structures wherein L2 or L3 is represented by formula 2, and (3) have Ar1 and Ar2 groups represented by formulas 4-1 to formula 4-5 as recited in claims 8 to 17. Claims 8 and 17 are not presently in condition for allowance, because they are not in independent form, and, because they encompass species wherein L1 and L4 are represented by formula 2; these species are withdrawn from consideration. As set forth above, examination has presently been limited to species encompassed by the grouping wherein L2 or L3 is represented by formula 2. Claims 8 and 17 would be allowable if rewritten in independent form including all limitations of the base claim, and, limited to require L2 or L3 to be represented by formula 2.
Regarding claims 12 and 20:
In view of the provisos recited in independent claims 1 and 13, the compounds recited in claims 12 and 20 which fall within the scope of the independent claims (i.e., satisfy all the recited provisos), and, which have structures wherein L2 or L3 is represented by formula 2 are free of prior art. Claims 12 and 20 are not presently in condition for allowance in view of the rejection under 35 USC 112(d), and, because they encompass species wherein L1 and L4 are represented by formula 2; such species are withdrawn from consideration. As set forth above, examination has presently been limited to the grouping wherein L2 or L3 is represented by formula 2. Claims 12 and 20 would be allowable if amended to overcome the rejection under 35 USC 112(d) and amended to delete species wherein L1 and L4 are represented by formula 2.
Conclusion
Applicant's amendment necessitated the 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 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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