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 .
Summary of Claims
Claims 1, 4-6, and 15 are amended and claims 16-20 are new due to Applicant's amendment dated 05/06/2026. Claims 1-20 are pending.
Response to Amendment
The objection to claims 1, 4-6, and 15 as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 05/06/2026.
The rejection of claims 5-8 and 12 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 as set forth in the previous Office Action is not overcome due to the Applicant’s amendment dated 05/06/2026. The rejection is maintained.
The rejection of claims 1-10 and 12-15 under 35 U.S.C. 103 as being unpatentable over Thomas (WO 2015/198073) in view of Hummert (US 2017/0373251 A1) is not overcome due to the Applicant’s amendment dated 05/06/2026. The rejection is herein revised to reflect the amended claim language.
The rejection of claim 11 under 35 U.S.C. 103 as being unpatentable over Thomas in view of Hummert and Meng (US 2018/0069188 A1) is not overcome due to the Applicant’s amendment dated 05/06/2026. The rejection is maintained.
Response to Arguments
Applicant’s arguments on pages 8-13 of the reply dated 05/06/2026 with respect to the rejection of claims 1-15 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –On pages 8-10, with respect to the rejection under 35 U.S.C. 112(b) as set forth in the previous office action, Applicant argues the claims are clear when interpreted in view of ¶ [0015] of the instant specification, which recites “it should be noted that throughout the application and the claims any An, Bn, Rn, etc. always refer to the same moieties, unless otherwise noted”. Applicant asserts this clearly explains that A1 in formula (I) is identical to A1 in formula (II).
Examiner's response –Paragraph [0015] of the instant specification fails to clearly define A1 to A6 in formula (I) are identical to A1 to A6 in formula (II), respectively. In particular, it is unclear what “same moieties” encompasses and which formulas this applies to. For example, it is unclear in paragraph [0015] whether “same moieties” is referring to the same moieties in the same formula or across multiple formulas.
However, even if the phrase “any An, Bn, Rn, etc. always refer to the same moieties” was clear, paragraph [0015] also recites An, Bn, Rn, etc. always refer to the same moieties “unless otherwise noted”. Claim 1 recites A1, A3, and A5 are independently selected from CN, etc. and A2, A4, and A6 are independently selected from substituted or unsubstituted C6 to C18 aryl, etc. Given the variables are selected “independently”, this allows for each A1 (and each A2 to A6) to be selected from the groups listed in claim 1 independent of one another. For example, one A1 may be selected as CN and another A1 may be selected as a fully fluorinated C1 to C6 alkyl.
For these reasons, paragraph [0015] does not clearly define A1 to A6 in formula (I) are identical to A1 to A6 in formula (II), respectively. Accordingly, the rejection is maintained.
Applicant's argument –On page 10, Applicant argues the phrase “substantially covalent matrix compound” is well-defined in paragraphs [0072]-[0078].
Examiner's response –Paragraphs [0072]-[0079] recite a substantially covalent matrix compound may be selected from at least one organic compound; may consist substantially from covalently bound C, H, O, N, S; wherein examples thereof include organometallic compounds comprising covalent bonds carbon-metal; wherein in one embodiment, the compound lacks metal atoms and majority of its skeletal atoms may be selected from C, O, S, and N; in one embodiment, the compound may have a molecular weight of ≥400 and ≤2000 g/mol; and wherein the compound may comprise at least one arylamine compound, diarylamine compound, triarylamine compound, a compound of formula (V) or a compound of formula (VI). That is, while the instant specification recites examples and embodiments of what the substantially covalent matrix compound may be, there is no specific definition for such a compound and thus, because “substantially” is a relative term not defined by the specification, it is unclear to the degree of which the matrix compound must be covalent. For example, it is unclear what would make a compound substantially covalent vs. not substantially covalent. For this reason, the term “substantially” in claim 12 is unclear and the rejection is maintained.
Applicant's argument –On pages 10-12, Applicant argues the cited references fail to teach a composition that includes at least two isomers of a radialene compound, which is required by the independent claims. Applicant argues in a compound of formula (I) is different from a compound of formula (II) only by the orientation of any one or more of formula (IIIa), formula (IIIb), or formula (IIIc).
Examiner's response –No where in the claims is there a specific limitation that requires the compound of formula (I) and the compound of formula (II) to be isomers. As discussed above, the claims do not limit the A1 to A6 in formula (I) to be identical to the A1 to A6 in formula (II), respectively. For this reason, Applicant’s arguments are not persuasive and the rejection is maintained.
Applicant's argument –On pages 12-13, Applicant argues none of the cited references teach or suggest the advantages described in the instant specification by using a mixture of isomers.
Examiner's response --It is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by Applicant. See MPEP 2144 IV.
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 5-8 and 12 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.
Claims 5 and 7 recite “at least one from A2, A4, and A6 is selected from” specific groups. Similarly, claim 8 recites “at least one from A2, A4, and A6 is fully substituted”. Given that A2, A4, and A6 appear in both formula (I) and formula (II), it is unclear whether “at least one from A2, A4, and A6” means 1) at least one from A2, A4, and A6 in formula (I) and at least one from A2, A4, and A6 in formula (II); or 2) at least one from A2, A4, and A6 in either formula (I) or formula (II). For purposes of examination, the limitation will be interpreted as at least one from A2, A4, and A6 in either formula (I) or formula (II).
Claim 6 recites “at least one from A1, A3, and A5 is selected from” specific groups. Similarly, claim 9 recites “at least one from A1, A3, and A5 is CN”. Given that A1, A3, and A5 appear in both formula (I) and formula (II), it is unclear whether “at least one from A1, A3, and A5” means 1) at least one from A1, A3, and A5 in formula (I) and at least one from A1, A3, and A5 in formula (II); or 2) at least one from A1, A3, and A5 in either formula (I) or formula (II). For purposes of examination, the limitation will be interpreted as at least one from A1, A3, and A5 in either formula (I) or formula (II).
The term “substantially” in claim 12 is a relative term which renders the claim indefinite. The term “substantially” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Accordingly, it is unclear what a substantially covalent matrix compound is. For purposes of examination, the limitation will be met if the at least one organic semiconductor layer comprises a covalent matrix compound.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-10 and 12-20 are rejected under 35 U.S.C. 103 as being unpatentable over Thomas (WO 2015/198073) in view of Hummert (US 2017/0373251 A1), as evidenced by Li (US 2020/0111960 A1) and LibreTexts (“22.3: Polymers.” Chemistry LibreTexts, 16 July 2022).
Regarding claims 1, 3-10, 12-13, and 15-20, Thomas teaches an improved OLED comprising an anode, a hole injection layer, a light-emitting layer, and a cathode, wherein the hole injection layer is an organic semiconductor doped with a first p-dopant and a second p-dopant that is different from the first p-dopant (bottom of page 2 and second half of page 4). Thomas teaches a specific example in Device Example B wherein the hole injection layer is formed by Formulation B, wherein Formulation B is a semiconducting polymer 1 doped with first dopant B and second dopant B (beginning of page 25 and bottom of page 27). First dopant B is C60F36 and second dopant B is NDP-9 (Table 3 on page 24).
As evidenced by Li, NDP-9 has the structure below (see page 3 of Li), and thus reads on the claimed formula (I) wherein: A1, A3, and A5 are each CN and A2, A4, and A6 are each a C6 aryl substituted with halogen and CN (claims 4-9).
NDP-9:
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The first dopant B (C60F36) fails to read on the claimed formula (II). However, Thomas does not limit the structure of the first dopant. Rather. Thomas recites exemplary p-dopants for the first dopant generically include organic and inorganic p-dopants (bottom of page 5).
Hummert teaches a [3]-radialene p-dopant represented by formula (I) for use in a semiconducting layer of an OLED (¶ [0007] and [0016]). Hummert teaches the [3]-radialene p-dopant is thermally robust, retains good performance, enables adjusting the doping strength and volatility, enables their manufacturing with more robust quality and higher yield, and provides additional degrees of freedom for designers of electronic devices (¶ [0029] and [0037]-[0039]). Hummert teaches examples of the [3] radialene p-dopant including compound A1 (page 5).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the first dopant B (C60F36) in Thomas’ Device Example B with a [3]-radialene p-dopant represented by Hummert’s formula (I), based on the teaching of Hummert. The motivation for doing so would have been to provide a p-dopant that is thermally robust, retains good performance, enables adjusting the doping strength and volatility, enables their manufacturing with more robust quality and higher yield, and provides additional degrees of freedom for designers of electronic devices, as taught by Hummert.
Specifically, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select compound A1, because it would have been choosing from a list of suitable [3] radialene p-dopants taught by Hummert, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the p-dopant in the hole injection layer of the device of Thomas and possessing the benefits taught by Hummert. One of ordinary skill in the art would have been motivated to produce additional devices comprising [3] radialene p-dopants taught by Hummert and having the benefits taught by Hummert in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
As shown by the structure below, compound A1 reads on the claimed formula (II) wherein: B1 is formula (IIIa); B2 is formula (IIIb); B3 is formula (IIIc); A1, A3, and A5 are each CN and A2, A4, and A6 are each a C6 aryl substituted with halogen and fully fluorinated C1 alkyl.
A1:
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Additionally, compound A1 reads on the claimed formula (IIa) (claim 3).
Per claim 12, as discussed above, the hole injection layer includes a semiconductor polymer. Polymers are formed from covalent bonds, as evidenced by the first paragraph of LibreTexts, and thus are considered a covalent matrix compound.
Per claims 16-20, each halogen in formula (I) and (II) is F.
Regarding claim 2, Thomas in view of Hummert teach the modified Device Example B including a hole injection layer comprising p-dopants NDP-9 and compound A1, as described above with respect to claim 1.
Thomas in view of Hummert fail to teach the modified Device Example B comprises an additional p-dopant. However, Thomas does teach an embodiment in which the organic semiconductor (the hole injection layer) may be doped with three or more different dopants, wherein examples of such dopants include p-dopants which may be organic or inorganic (page 5).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to further include an additional p-dopant in the hole injection layer to arrive at an organic semiconductor doped with three dopants, because this would have been combining the prior art elements of Thomas according to known methods to yield predictable results of an OLED, as taught by Thomas. See MPEP 2143.I.(A).
While Thomas in view of Hummert fail to specifically teach the structure of the third p-dopant, as discussed above, Hummert teaches a [3]-radialene p-dopant represented by formula (I) is thermally robust, retains good performance, enables adjusting the doping strength and volatility, enables their manufacturing with more robust quality and higher yield, and provides additional degrees of freedom for designers of electronic devices (¶ [0029] and [0037]-[0039]). Hummert teaches examples of the [3] radialene p-dopant including compound A2 (page 5).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select a [3]-radialene p-dopant represented by Hummert’s formula (I) as the third p-dopant, based on the teaching of Hummert. The motivation for doing so would have been to provide a p-dopant that is thermally robust, retains good performance, enables adjusting the doping strength and volatility, enables their manufacturing with more robust quality and higher yield, and provides additional degrees of freedom for designers of electronic devices, as taught by Hummert.
Specifically, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select compound A2, because it would have been choosing from a list of suitable [3] radialene p-dopants taught by Hummert, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the third p-dopant in the hole injection layer of the device of Thomas in view of Hummert and possessing the benefits taught by Hummert. One of ordinary skill in the art would have been motivated to produce additional devices comprising [3] radialene p-dopants taught by Hummert and having the benefits taught by Hummert in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
As shown by the structure below, compound A2 reads on the claimed formula (II) wherein: B1 is formula (IIIa); B2 is formula (IIIb); B3 is formula (IIIc); A1, A3, and A5 are each CN and A2, A4, and A6 are each a C6 aryl substituted with F and fully fluorinated C1 alkyl.
A2:
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Regarding claim 14, While Thomas fails to specifically teach the modified Device Example B is a display, Thomas does teach the OLED may be used in an active matrix display or a passive matrix display (bottom of page 21).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to use the modified Device Example B in an active matrix display or a passive matrix display, because this would have been combining the prior art elements of Thomas according to known methods to yield predictable results, as taught by Thomas. See MPEP 2143.I.(A).
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Thomas (WO 2015/198073) in view of Hummert (US 2017/0373251 A1) as applied to claim 1 above, and further in view of Meng (US 2018/0069188 A1).
Regarding claim 11, Thomas in view of Hummert teach the modified Device Example B including a hole injection layer comprising p-dopants NDP-9 and compound A1, and a light-emitting layer, as described above with respect to claim 1.
Thomas in view of Hummert fail to specifically teach the device comprises two light-emitting layer and an additional layer therebetween.
Meng teaches an organic light-emitting device having higher luminous efficiency by including a first electrode 110, a first light-emitting layer 120, a first low work function layer 131, a second low work function layer 132, a conductive etching-resistant layer 133, a first hole-injection layer 134, a second light-emitting layer 140, and a second electrode 150, as shown in Fig. 1 (¶ [0004] and [0027]-[0028]).
Fig. 1:
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Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to further include in the modified Device Example B a first light-emitting layer, a first low work function layer, a second low work function layer, and a conductive etching-resistant layer between the anode and the hole injection layer of modified Device Example B, to arrive at a device having the structure of Meng, based on the teaching of Meng. The motivation for doing so would have been to provide a device with higher luminous efficiency, as taught by Meng.
The resulting modified Device Example B includes two light-emitting layers with a hole injection layer therebetween, wherein the hole injection layer includes the p-dopants NDP-9 and compound A1.
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRAELYN R WATSON whose telephone number is (571)272-1822. The examiner can normally be reached M-F 7:30am-5pm.
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/BRAELYN R WATSON/Examiner, Art Unit 1786
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