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 .
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.
Response to Amendment
The amendment of 30 April 2026 has been entered.
Disposition of claims:
Claims 1-2, 6, 10, and 13 have been amended.
Claims 3-5, 7-9, and 17 are cancelled.
Claims 1-2, 6, 10-16, and 18-20 are pending.
Response to Arguments
Applicant's arguments filed 30 April 2026 regarding the rejections of claims 1-12 and 14-20 under 35 U.S.C. 103 as being unpatentable over Ahn et al. (WO 2014/030921 A1) (hereafter “Ahn”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that the goals of Ahn differ from the goals of the current application and that stemming from this difference, the compounds of the current claims have properties that differentiate the claimed compound from those of Ahn. These properties include reduced electron cloud density due to the presence of fluorine substituents; increased distortion degree providing a structure that has high thermal stability and reduced electron transport rate due to the presence of both a dibenzofuran/dibenzothiophene group and an N-phenylcarbazole within a triaryl amine compound; the use of the compound as an electron blocking material; and improved organic light emitting device efficiency, service life, and driving voltage through the electron blocking properties. Applicant argues that Ahn’s goal was to improve thermal stability, reduce driving voltage by introducing dibenzothiophene to arylamine. This contrasts with the instant because the increased service life is increase through electron blocking.
In response to applicant's argument that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., the use of the claimed compounds as an electron blocking material) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
Insofar as electron blocking could be a property that may not be possessed by the compounds of Ahn, there is no quantified electron blocking property described in the instant specification. While there is data for example devices in which compounds of the current claims are utilized in an electron blocking layer, these data are improvements in device performance characteristics rather than a characterization of electron blocking property. Furthermore, from as evidence of improvements in device performance characteristics these results are not commensurate in scope with the current claims, because the results are obtained using a specific device architecture in which an electron blocking layer is used in conjunction with a hole injection layer and a hole transport layer and additionally, a specific light-emitting layer composition is used. None of these structural characteristics are claimed, and it is not clear that similar device improvements would be observed absent these structural characteristics.
Reduced electron cloud density is described in the specification, but this is described as a consequence of fluorine substitution, which is already present in the cited compound of Ahn.
Increased distortion degree providing a structure that has high thermal stability and reduced electron transport rate is also described, but this is described as a consequence of the presence of both a dibenzofuran/dibenzothiophene group and an N-phenylcarbazole within a triaryl amine compound. These features are already present in the cited compound of Ahn.
Applicant also describes improved organic light emitting device efficiency, service life, and driving voltage. Applicants proffered data does indeed show these improvements. However, it is unclear what differences between the compound C-57 of Ahn and the compounds of the experimental examples of the instant specification leads to these improvements. In other words, there are multiple differences between the compound C-57 and the tested compounds of the instant specification. Thus, it cannot be determined that the addition of a p-phenylene linker between the dibenzothiophene structure on the central amine N atom of the compound C-57 of Ahn (the sole modification to the compound) would result in the unexpectedly improved properties. Thus, it cannot be determined that the compounds as currently claimed are nonobvious over the teachings of Ahn.
Furthermore, the results are not commensurate in scope with the current claims, because the results are obtained using a specific device architecture in which an electron blocking layer is used in conjunction with a hole injection layer and a hole transport layer and additionally, a specific light-emitting layer composition is used. None of these structural characteristics are claimed, and it is not clear that similar device improvements would be observed absent these structural characteristics.
Applicant's arguments filed 30 April 2026 regarding the rejections of claims 1-12 and 14-20 under 35 U.S.C. 103 as being unpatentable over Ahn et al. (WO 2014/030921 A1) (hereafter “Ahn”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that the selection of a fluorine substituent placed on the carbazolyl moiety to modify the compound of Ahn would have been the result of excessive picking and choosing from a list of options that do not represent a finite number of identified, predictable solutions.
For the rejections of claims 1-12 and 14-20 under 35 U.S.C. 103 as being unpatentable over Ahn et al. (WO 2014/030921 A1) (hereafter “Ahn”) set forth in the last Office action the modification of the compound of Ahn through the addition of a fluorine substituent to the compound of Ahn was not a subject of the rejections. The fluorine substituent was already present. Thus, with respect to this set of rejections the argument is moot.
Applicant's arguments filed 30 April 2026 regarding the rejections of claims 1-13 and 17 under 35 U.S.C. 103 as being unpatentable over Ahn et al. (WO 2014/030921 A1) (hereafter “Ahn”) in view of Kamatani et al. (US 2003/0189216 A1) (hereafter “Kamatani”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that the goals of Ahn differ from the goals of the current application and that stemming from this difference, the compounds of the current claims have properties that differentiate the claimed compound from those of Ahn. These properties include reduced electron cloud density due to the presence of fluorine substituents; increased distortion degree providing a structure that has high thermal stability and reduced electron transport rate due to the presence of both a dibenzofuran/dibenzothiophene group and an N-phenylcarbazole within a triaryl amine compound; the use of the compound as an electron blocking material; and improved organic light emitting device efficiency, service life, and driving voltage through the electron blocking properties. Applicant argues that Ahn’s goal was to improve thermal stability, reduce driving voltage by introducing dibenzothiophene to arylamine. This contrasts with the instant because the increased service life is increase through electron blocking.
In response to applicant's argument that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., the use of the claimed compounds as an electron blocking material) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
Insofar as electron blocking could be a property that may not be possessed by the compounds of Ahn, this property is not by itself characterized in a comparison to the closest prior art. While there is data for example devices in which compounds of the current claims are utilized in an electron blocking layer, these data are improvements in device performance characteristics rather than a characterization of electron blocking property. Furthermore, from as evidence of improvements in device performance characteristics these results are not commensurate in scope with the current claims, because the results are obtained using a specific device architecture in which an electron blocking layer is used in conjunction with a hole injection layer and a hole transport layer and additionally, a specific light-emitting layer composition is used. None of these structural characteristics are claimed, and it is not clear that similar device improvements would be observed absent these structural characteristics.
Reduced electron cloud density is described in the specification, but similar to the concept of electron blocking as a property described above, this property is not by itself characterized in a comparison to the closest prior art. While there is data for example devices in which compounds of the current claims are utilized in an electron blocking layer, these data are improvements in device performance characteristics rather than a characterization of electron blocking property. Furthermore, from as evidence of improvements in device performance characteristics these results are not commensurate in scope with the current claims, because the results are obtained using a specific device architecture in which an electron blocking layer is used in conjunction with a hole injection layer and a hole transport layer and additionally, a specific light-emitting layer composition is used. None of these structural characteristics are claimed, and it is not clear that similar device improvements would be observed absent these structural characteristics.
Increased distortion degree providing a structure that has high thermal stability and reduced electron transport rate is also described, but this is described as a consequence of the presence of both a dibenzofuran/dibenzothiophene group and an N-phenylcarbazole within a triaryl amine compound. These features are already present in the cited compound of Ahn.
Applicant also describes improved organic light emitting device efficiency, service life, and driving voltage. Applicants proffered data does indeed show these improvements. However, it is unclear what differences between the compound C-59 of Ahn and the compounds of the experimental examples of the instant specification leads to these improvements. In other words, there are multiple differences between the compound C-59 and the tested compounds of the instant specification. While the Comparagive Compound B is also tested—the difference between Comparative Compound B and the current claims being the lack of a fluorine on the carbazolyl group—again, there are too many differences between Comparative Compound B and the tested compounds (Compounds 11 and 15 being most similar) for the observed improvements to be clearly attributable to the presence of a fluorine substituent. Thus, it cannot be determined that the addition of a fluorine to the carbazolyl group would result in unexpectedly improved properties with respect to the cited prior art. Thus, it cannot be determined that the compounds as currently claimed are nonobvious over the teachings of Ahn and Kamatani.
Furthermore, the results are not commensurate in scope with the current claims, because the results are obtained using a specific device architecture in which an electron blocking layer is used in conjunction with a hole injection layer and a hole transport layer and additionally, a specific light-emitting layer composition is used. None of these structural characteristics are claimed, and it is not clear that similar device improvements would be observed absent these structural characteristics.
Applicant's arguments filed 30 April 2026 regarding the rejections of claims 1-13 and 17 under 35 U.S.C. 103 as being unpatentable over Ahn et al. (WO 2014/030921 A1) (hereafter “Ahn”) in view of Kamatani et al. (US 2003/0189216 A1) (hereafter “Kamatani”) set forth in the last Office action have been fully considered but they are not persuasive.
Applicant argues that the selection of a fluorine substituent placed on the carbazolyl moiety to modify the compound of Ahn would have been the result of excessive picking and choosing from a list of options that do not represent a finite number of identified, predictable solutions. Applicant further asserts that the teachings of Kamatani are not relevant.
Applicant is correct that construction of a compound from the general formula of Ahn alone would involve too many choices from too large of a number of options for the construction to be a choice from a finite number of identified, predictable solutions. However, the rejections are based upon a particular exemplified compound of Ahn. Thus, the characterization of the rejection being the result of a selection from countless options is incorrect. The rejection is simply the choice of substituting a fluorine substituent onto an already disclosed compound of Ahn. While the selection of fluorine could be characterized as being solely from the lists provided in paragraphs [19] and [34] in other circumstances, the current rejection is made both in light of the other exemplified compounds of Ahn as well as the teachings of Kamatani. Exemplified compound C-57 of Ahn shows that fluorine substitution onto the carbazolyl moiety was envisioned by Ahn. Additionally, with respect to the other modification of the rejection. Biphenyl as the Ar1 of Ahn—which can be equated with the instant (—L—Ar) —is described in compounds C-16, C-25, C-27, C-36, C-54, C-69, C-72, C-74, C-81, and C-85 of Ahn. Furthermore, the teachings of Kamatani show why one of ordinary skill in the art would be motivated to select fluorine as a substituent.
Applicant asserts that Kamatani is directed to a different problem and that the compound structures of Kamatani are too diverse to motive substitution onto the carbazolyl moiety of the compound of Ahn. However, the position of the fluorine substituent is based upon the teaching of compound C-57 of Ahn, as described above. Kamatani is relied upon for the general teaching of Kamatani that fluorine substituents allow for easier sublimation and for improved stability. Applicant has not disputed the correctness of this general teaching of Kamatani. Thus, based on this general teaching of Kamatani and the structure of exemplified compound C-57 of Ahn as evidence of a fluorine substituent on the carbazolyl moiety of the compound of Ahn being envisioned by Ahn, the modification is still considered obvious, and Applicant’s arguments are not found to be persuasive.
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.
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.
Claim(s) 1-2, 6, 10-12, 14-16, and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Ahn et al. (WO 2014/030921 A1) (hereafter “Ahn”).
Regarding claims 1-2, 6, 10-12: Ahn discloses the compound shown below {(paragraph [0035]: The compounds of the disclosure of Ahn are exemplified by the compounds in paragraphs [0036]-[0039]), (paragraph [0039]: Compound C-57)}.
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The compound shown above does not read on the current claims, because the structures that can be equated with both of the instant L1 and L2 are single bonds, and the claims require at least one of the instant L1 and L2 to be other than a single bond.
However, Ahn teaches that the compounds of Ahn have the structure of formula 1 of Ahn, shown below {paragraphs [0013]-[0014]}.
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Where L3 of Ahn can optionally be substituted or unsubstituted arylene {paragraph [0017]}.
This is exemplified by compounds C-59 to C-69, C-71 to C-74, C-77 to C-81, C-83 to C-85, C-87 to C-96, C-98 to C-100, C-102, and C-105 of Ahn where L3 of Ahn is paraphenylene {paragraphs [0038] to [0039]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the compound C-57 of Ahn by substituting a p-phenylene group in place of a single bond that is L3 of Ahn, based on the teaching of Ahn. The substitution would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of p-phenylene would have been a choice from a finite number of identified, predictable solutions (the exemplified groups L3 of Ahn), with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of chemical moieties and chemical moiety positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Regarding claims 14-16 and 19-20: Ahn teaches all of the features of claim 1, as outlined above.
Ahn does not teach a specific device comprising the compound of Ahn described above.
However, Ahn teaches that the compounds of the disclosure of Ahn are useful as materials of a hole transport layer of an organic light emitting device {paragraphs [0044]-[0047], and [0113]}.
Furthermore, Ahn teaches an organic electroluminescence device having a structure of an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode {paragraph [0163]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have further modified the compound of Ahn such that it was used as the material of the hole transport layer of the device of Ahn described above, based on the teaching of Ahn. The modification would have been a combination of prior art elements according to known methods to yield predictable results. See MPEP 2143(I)(A). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of materials to be used to make an organic light-emitting device in order to produce optimal organic light-emitting devices.
An organic electroluminescence device is an electronic device.
Regarding claim 20: Ahn teaches all of the features with respect to claim 15, as outlined above.
In the device of Ahn described above, the hole injection layer can be equated with a first hole transport layer that is closer to the anode. This is because the hole injection layer must necessarily transport holes. The layer labeled by Ahn as the hole transport layer can be equated with a second hole transport layer that is further from the anode than the first hole transport layer.
Regarding claim 18: Ahn teaches all of the features with respect to claim 10, as outlined above.
The modified compound C-57 of Ahn does not comprise a biphenylene linking group between the carbazolyl group and the amine N atom.
However, Ahn teaches that the compounds of Ahn have the structure of formula 1 of Ahn, shown below {paragraphs [0013]-[0014]}.
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Where L1 and L2 of Ahn can optionally be substituted or unsubstituted arylene {paragraphs [0016]-[0017]}.
This is exemplified by compounds C-22, C-26, and C-81 of Ahn where L1 of Ahn is an m-phenylene group and L2 of Ahn is a p-phenylene group {paragraphs [0037] to [0039]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have further modified the compound C-57 of Ahn by substituting an m-phenylene group in place of the p-phenylene group as L1 of Ahn and a p-phenylene group in place of a single bond as L2 of Ahn, based on the teaching of Ahn. The substitutions would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of m-phenylene and p-phenylene would have been choices from a finite number of identified, predictable solutions (the exemplified groups L1 and L2 of Ahn), with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of chemical moieties and chemical moiety positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Claim(s) 1-2, 6, and 10-13 are rejected under 35 U.S.C. 103 as being unpatentable over Ahn et al. (WO 2014/030921 A1) (hereafter “Ahn”) in view of Kamatani et al. (US 2003/0189216 A1) (hereafter “Kamatani”).
Regarding claims 1-2, 6, and 10-13: Ahn discloses the compound shown below {(paragraph [0035]: The compounds of the disclosure of Ahn are exemplified by the compounds in paragraphs [0036]-[0039]), (paragraph [0039]: Compound C-59)}.
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The compound shown above does not read on the current claim 11, because the carbazolyl group lacks a fluorine substituent and a structure that can be equated with the instant -L-Ar that is consistent with a compound of the current claim 11.
However, Ahn teaches that the compounds of Ahn have the structure of formula 1 of Ahn, shown below {paragraphs [0013]-[0014]}.
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Where Ar1 of Ahn can optionally be substituted or unsubstituted aryl {paragraph [0018]}.
This is exemplified by compounds C-16, C-25, C-27, C-36, C-54, C-69, C-72, C-74, C-81, and C-85 of Ahn where Ar1 of Ahn is biphenyl with a p-phenylene group {paragraphs [0036] to [0039]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the compound C-59 of Ahn by substituting a biphenyl group comprising p-phenylene group in place of the phenyl group on the amine N atom, based on the teaching of Ahn. The substitution would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). The selection of a biphenyl group comprising a p-phenylene would have been a choice from a finite number of identified, predictable solutions (the exemplified groups L3 of Ahn), with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of chemical moieties and chemical moiety positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
The modified compound C-59 of Ahn does not have the structure of the current claims, because it lacks a fluorine substituent on the carbazolyl group.
However, Ahn teaches that the compounds of Ahn have the structure of formula 1 of Ahn, shown below {paragraphs [0013]-[0014]}.
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Where R1 or R2 of Ahn can be fluorine {paragraph [0019]}.
This is exemplified by compound C-57 of Ahn {paragraph [0038]}.
Furthermore, Kamatani teaches that fluorine substituents allow for easier sublimation and for improved stability {paragraphs [0044]-[0046]}.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have further modified the compound C-59 of Ahn by substituting a fluorine group at a position equivalent to that in the instant Compound 30, based on the teaching of Ahn and Kamatani. The motivation for doing so would have been to provide a compound having the properties of easier sublimation and improved stability, as taught by Kamatani. The selection of the position for the fluorine substitution would have been a choice from a finite number of identified, predictable solutions (the exemplified possible positions for substitution on the compound of Ahn), with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of chemical moieties and chemical moiety positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Conclusion
THIS ACTION IS MADE FINAL. 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 DYLAN CLAY KERSHNER whose telephone number is (303)297-4257. The examiner can normally be reached M-F, 9am-5pm (Mountain).
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/DYLAN C KERSHNER/Primary Examiner, Art Unit 1786
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