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 .
Election/Restriction
Applicant’s election without traverse of claims 1, 3-4 and 6-14 in the reply filed on 01/16/2026 is acknowledged. Claim 5 is withdrawn from consideration.
Summary of Claims
Claims 1, 3-4, and 11-12 are amended and claim 2 is cancelled due to Applicant's amendment dated 05/12/2026. Claims 1 and 3-14 are pending and claim 5 is withdrawn.
Response to Amendment
The rejection of claim 2 as set forth in the previous Office Action is moot because claim 2 is cancelled due to the Applicant's amendment dated 05/12/2026.
The objection to claim 4 as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 05/12/2026.
The rejection of claims 3 and 11-12 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 overcome due to the Applicant’s amendment dated 05/12/2026. The rejection is withdrawn.
The rejection of claims 1-3 under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Matsuki (English translation of WO 2016009823 A obtained from Global Dossier) is overcome due to the Applicant’s amendment dated 05/12/2026. The rejection is withdrawn.
The rejection of claims 6-7 and 9-12 under 35 U.S.C. 103 as being unpatentable over Matsuki is overcome due to the Applicant’s amendment dated 05/12/2026. The rejection is withdrawn.
The rejection of claim 4 under 35 U.S.C. 103 as being unpatentable over Matsuki in view of Pflumm (US 2016/0190447 A1) and Fennimore (US 2017/0200893 A1) is not overcome due to the Applicant’s amendment dated 05/12/2026. The rejection is maintained.
The rejection of claims 6-8 and 11-12 under 35 U.S.C. 103 as being unpatentable over Matsuki in view of Kim (US 2017/0294587 A1) is overcome due to the Applicant’s amendment dated 05/12/2026. The rejection is withdrawn.
The rejection of claims 13-14 under 35 U.S.C. 103 as being unpatentable over Matsuki in view of Zhen (US 2010/0117946 A1) is overcome due to the Applicant’s amendment dated 05/12/2026. The rejection is withdrawn.
The rejection of claims 13-14 under 35 U.S.C. 103 as being unpatentable over Matsuki in view of Kim and Zhen is overcome due to the Applicant’s amendment dated 05/12/2026. The rejection is withdrawn.
Response to Arguments
Applicant’s arguments on pages 15-21 of the reply dated 05/12/2026 with respect to the rejection of claims 1, 3-4, and 6-14 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –On pages 15-16, Applicant argues that compound 119 of the cited reference Matsuki does not teach the claims as amended.
Examiner's response –As discussed in greater detail in the rejection below, the previously cited references Matsuki in view of Pflumm and Fennimore teach the claims as amended.
Applicant's argument –On pages 16-18, Applicant argues the modification of compound 119 with the teaching of Pflumm and Fennimore relies on impermissible hindsight. Applicant argues: the generic disclosure of Matsuki does not provide a reason to alter the specific structure of compound 119; Pflumm does not teach that one of the two deuterated biphenyl groups of Matsuki’s compound 119 should be selectively replaced with spirobifluorene, and spirobifluorene is not a routine substitute for biphenyl; and Fennimore’s general teaching of deuteration does not supply the missing motivation to create the claimed scaffold.
Examiner's response –In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. As discussed above and outlined below, the rejections take into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the Applicant's disclosure.
As discussed below, Matsuki teaches A1 may be a substituted or unsubstituted fluorenyl group (¶ [0014]). While Matsuki does not teach a specific exemplified compound having the structure of compound 119 wherein the fluorenyl group is unsubstituted, the invention of the prior art is not limited to or defined by only those embodiments disclosed in the examples. A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art, including nonpreferred embodiments. See MPEP 2123. Accordingly, A1 being an unsubstituted fluorenyl is within the scope of Matsuki’s general formula (1) and thus 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 substituted fluorenyl group with an unsubstituted fluorenyl group, because Matsuki teaches A1 may suitably be selected as unsubstituted fluorenyl. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful in the device of Matsuki and possess the benefits taught by Matsuki. See MPEP 2143.I.(B).
While Pflumm does not specifically teach that one of the two deuterated biphenyl groups of Matsuki’s compound 119 should be selectively replaced with spirobifluorene, Matsuki’s compound 119 reads on Pflumm’s formula (1) except wherein it does not contain a spirofluorene group. Thus, 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 one of the biphenyl groups of Matsuki’s compound 119 with spirobifluorene, as shown in Pflumm’s compound 4, to arrive at a compound of Pflumm’s formula (1) based on the teaching of Pflumm. The motivation for doing so would have been to provide a device with improved lifetime, efficiency, and operating voltage, as taught by Pflumm.
Additionally, as discussed below, Fennimore teaches 10-100% deuterated materials can be less susceptible to degradation by holes, electrons, or excitons, have greater processing tolerance, and can potentially improve device lifetime compared to their non-deuterated analogs (¶ [0097]-[0098]). This is sufficient motivation for one of ordinary skill in the art to deuterate the compound of Matsuki to arrive at a compound of the claimed invention.
As discussed in the rejection below, the modified compound 119 of Matsuki in view of Pflumm and Fennimore reads on Matsuki’s general formula (1) wherein: L1 and L2 are each a single bond; A1 and A2 are each a substituted fluorenyl group, wherein substituents of A2 combine to form a ring; R1, R2, R4, and R5 are each deuterium and R3 is a substituted phenyl group (see Matsuki, ¶ [0010]). Accordingly, the modifications of Pflumm and Fennimore are within the scope of Matsuki’s general formula (1) and thus one of ordinary skill in the art would expect the resulting compound to behave as intended by Matsuki and obtain the benefits of Matsuki.
Applicant's argument –On pages 18-21, Applicant argues the claimed compound P-8 obtains unexpectedly improved lifespan over the prior art. Applicant points to Table 2 of the instant specification for support. In Table 2, Example 8 is compared to Comparative examples 1 and 2, wherein Example 8 comprises P-8 and Comparative examples 1 and 2 comprise Comparative compounds 1 and 2, respectively. Applicant points out that Comparative compound 1 is identical to Pflumm’s compound 4. Applicant appears to attribute at least some of this improvement to the percent deuteration of compound P-8, as Comparative compound 1 is 0% deuterated and Comparative compound is only 45.7% deuterated.
Comp. compound 1:
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225
224
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Comp. compound 2:
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246
210
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Examiner's response –Overcoming a rejection based on unexpected results requires at least the combination of three different elements: (i) the results must fairly compare with the closest prior art in an affidavit or declaration under 37 CFR 1.132, (ii) the claims must be commensurate in scope, and (iii) the results must truly be unexpected. MPEP 716.02. Additionally, the burden rests with Applicant to establish the results are unexpected and significant. MPEP 716.02(b).
While Applicant points to Table 2 to show that compound P-8 obtains unexpectedly improved lifespan in comparison to Pflumm’s compound 4 (i.e., Comparative compound 1), Applicant attributes at least some of this improvement to the percent deuteration of compound P-8. While Pflumm’s compound 4 is not deuterated, Matsuki’s compound 119 is 66% deuterated. That is, Matsuki’s compound 119 already anticipates a compound that is deuterated with the claimed range of 59-73%. Accordingly, at least with respect to the percent deuteration, a comparison between compound P-8 and Comparative compound 1 does not show unexpected results over the prior art Matsuki.
Comparison with closest prior art
Applicant has not made a comparison to the closest prior art. The compounds of the instant specification comprise a different structure than the compounds of Matsuki.
For example, Matsuki’s compound 119 is shown below in comparison to the claimed compound P-8.
119:
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286
306
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P-8:
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584
482
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Compound is 66% deuterated and contains a deuterated C6 aryl group in the location of the claimed R3 and only hydrogen in the location of the claimed R4. A compound containing 66% deuteration, a deuterated C6 aryl group in the location of R3, and hydrogen in the location of R4 is within the scope of Formula 3. In contrast, compound P-8 is 73% deuterated and contains only deuterium in the location of R3 and a combination of hydrogen and deuterium in the location of R4. As no explanation is provided for the differences between these compounds, it is unclear if a comparison between compounds comprising the same structure as compound 119 (66% deuteration, a deuterated C6 aryl group in the location of R3, and hydrogen in the location of R4) that also comprises a spirobifluorene group would obtain the same results discussed by Applicant. Accordingly, a comparison of the closest prior art has not been made.
Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, and if not explained should be noted and evaluated, and if significant, explanation should be required. MPEP 716.02(e).
Commensurate in Scope
As discussed above, Matsuki’s compound is 66% deuterated and contains a deuterated C6 aryl group in the location of R3 and hydrogen in the location of R4. This is within the scope of the claimed Formula 3.
As claim 1 is directed to the broad structures of Formulas 3 and 4 but the device discussed (Example 8) only recites one specific compound, the claims are not commensurate in scope. For example, as discussed above, the prior art teaches different materials than the instant specification including a compound containing a deuterated C6 aryl group in the location of R3 and hydrogen in the location of R4. As there are no results comprising the materials of the prior art, it is unclear if the same results discussed by Applicant would be present.
Additionally, the data shown in Table 2 is not commensurate in scope with the claimed invention for at least the reasons that the data is shown for the use of a compound in an emitting auxiliary layer, whereas claim 1 is directed to a compound (see instant pgs. 29-30). The improved properties relating to lifespan are shown when the compound is used in an emitting auxiliary layer of an OLED with specific materials used for adjacent layers (see instant pgs. 29-30). None of these limitations are required by the claim. No evidence has been provided to show that the unexpected results would be present for the use of the compound in other layers.
Unexpected Results
While there is improvement in lifespan between the instant devices and comparative devices, it is unclear whether these performances are truly unexpected.
As discussed further in the rejection below, the previously cited reference Fennimore teaches deuterated materials can improve device lifetime compared to their non-deuterated analogs (¶ [0098]). Accordingly, it is unclear whether the degree of improvement shown by the data in the Declaration is truly unexpected.
Claim Objections
Claims 3-4 and 6 are objected to because of the following informalities:
In claims 3-4 and 6, it is recommended to replace “Formula 1” with “Formula 3 or 4”.
Appropriate correction is required.
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, 3-4, 6-7, and 9-12 are rejected under 35 U.S.C. 103 as being unpatentable over Matsuki (English translation of WO 2016009823 A obtained from Global Dossier) in view of Pflumm (US 2016/0190447 A1) and Fennimore (US 2017/0200893 A1).
Regarding claims 1 and 3-4, Matsuki teaches a light emitting element having improved luminous efficiency and life durability by including a monoamine derivative represented by general formula (1) wherein examples thereof include compound 119 (¶ [0006]-[0008] and [0078]; structure on pg. 18).
general formula (1):
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119
159
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119:
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286
306
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Compound 119 fails to include an unsubstituted fluorene group. However, in general formula (1), Matsuki teaches A1 may be a substituted or unsubstituted fluorenyl group (¶ [0014]).
Therefore, given the general formula and teachings of Matsuki, 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 substituted fluorenyl group with an unsubstituted fluorenyl group, because Matsuki teaches A1 may suitably be selected as unsubstituted fluorenyl. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful in the device of Matsuki and possess the benefits taught by Matsuki. See MPEP 2143.I.(B).
The modified compound 119 fails to include a spirobifluorene group. However, in general formula (1), Matsuki teaches A2 may be a substituted or unsubstituted fluorenyl group (¶ [0014]).
Pflumm teaches compounds represented by formula (1) for use in organic electroluminescent devices, wherein the compounds provide devices with improved lifetime, efficiency, and operating voltage (¶ [0005]-[0006]). Examples of compounds represented by formula (1) include compound 4 (pg. 15).
formula (1):
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132
242
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4:
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238
212
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Therefore, in compound 119, 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 one of the biphenyl groups with spirobifluorene, as shown in Pflumm’s compound 4, to arrive at a compound of Pflumm’s formula (1) based on the teaching of Pflumm. The motivation for doing so would have been to provide a device with improved lifetime, efficiency, and operating voltage, as taught by Pflumm.
The modified compound 119 fails to read on a claimed compound as it does not comprise six deuterium atoms on the fluorenyl group, seven deuterium atoms on the biphenyl group, and twelve deuterium atoms on the spirobifluorene group. However, as shown in general formula (1), Matsuki teaches substituents of the compound may be hydrogen or deuterium (¶ [0035] and [0041]-[0042]).
Fennimore teaches deuterated materials can be less susceptible to degradation by holes, electrons, or excitons, have greater processing tolerance, and can potentially improve device lifetime compared to their non-deuterated analogs (¶ [0098]). Fennimore teaches deuterated materials may be 10-100% deuterated (¶ [0097]).
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 deuterium atoms on the modified compound 119 such that it is 10-100% deuterated, based on the teaching of Fennimore. The motivation for doing so would have been to provide a compound that is less susceptible to degradation by holes, electrons, or excitons, has greater processing tolerance, and can improve device lifetime, as taught by Fennimore.
Particularly, 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 six deuterium atoms on the fluorenyl group, seven deuterium atoms on the biphenyl group, and twelve deuterium atoms on the spirobifluorene group to arrive at the structure of the claimed compound P-8, because it would have been choosing from a list of suitable positions in which to substitute deuterium, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in the device of Matsuki in view of Pflumm and Fennimore and possessing the benefits taught by Matsuki, Pflumm, and Fennimore. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Matsuki’s general formula (1) having the benefits taught by Matsuki, Pflumm, and Fennimore in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified compound 119 reads on Matsuki’s general formula (1) wherein: L1 and L2 are each a single bond; A1 and A2 are each a substituted fluorenyl group, wherein substituents of A2 combine to form a ring; R1, R2, R4, and R5 are each deuterium and R3 is a substituted phenyl group (see Matsuki, ¶ [0010]). Accordingly, the modified compound 119 is expected to obtain the benefits of Matsuki.
The modified compound 119 reads on formula (1) of Pflumm wherein: Ar is not required to be present; Ar1 is an aromatic ring system having 12 C atoms and Ar2 is an aromatic ring system having 13 C atoms; R is D; n is 3 or 4, m is 2, and p is 0 (see Pflumm, ¶ [0006]-[0015]). Accordingly, the modified compound 119 is expected to obtain the benefits of Pflumm.
The modified compound 119 reads on the claimed compound P-8 (claim 4) and is reproduced below in comparison to the claimed Formula 3.
3:
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183
425
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modified 119:
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337
277
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The modified compound 119 is 73% deuterated and reads on the claimed Formulas 3 and 6 (claims 1 and 3) wherein:
R1 and R1 are each a C1 alkyl group;
R3 is deuterium and R4, R6, and R7 are each a combination of deuterium and hydrogen;
L1 to L3 are each a single bond;
a and e are each 4 and b and d are each 3;
Ar2 is a C12 aryl group; and
Y1 is CR’R”, wherein R and R” are bonded to each other to form a fluorenyl group.
Regarding claims 6-7 and 9-12, Matsuki in view of Pflumm and Fennimore teach the modified compound 119 as described above with respect to claim 1.
Matsuki fails to teach an example of a device specifically including the modified compound 119. However, Matsuki does teach a light emitting element having the configuration of anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/charge generating layer/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode, wherein the monoamine derivative represented by general formula (1) is preferably used in the hole transport layer (¶ [0081]).
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 compound 119 in a hole transport layer of the device described above in ¶ [0081] of Matsuki, because this would have been combining the prior art elements of Matsuki according to known methods to yield predictable results of a device with having improved luminous efficiency and life durability, as taught by Matsuki. See MPEP 2143.I.(A).
Per claim 10, the hole injection layer improves the luminous efficiency of the device, and thus may be considered a light efficiency enhancing layer (see Matsuki, ¶ [0089]).
Per claim 11, each stack includes hole transport layer/light-emitting layer/electron transport layer.
Claims 6-8 and 11-12 are rejected under 35 U.S.C. 103 as being unpatentable over Matsuki (English translation of WO 2016009823 A obtained from Global Dossier) in view of Pflumm (US 2016/0190447 A1) and Fennimore (US 2017/0200893 A1) as applied to claim 6 above, and further in view of Kim (US 2017/0294587 A1).
Regarding claims 6-8 and 11-12, Matsuki in view of Pflumm and Fennimore teach the modified compound 119 as described above with respect to claim 1.
modified 119:
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337
277
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Matsuki fails to teach a device including an emitting auxiliary layer wherein the emitting auxiliary layer comprises the modified compound 119. However, Matsuki teaches the monoamine derivate represented by general formula (1) has improved luminous efficiency and durability (¶ [0025]).
Kim teaches an organic light-emitting device including a first electrode 110, a hole transport layer 151-2, a HT-emission auxiliary layer 153-1, an emission layer 153-1-EM, an ET-emission auxiliary layer 153-1-ET (electron transport layer), a first charge generation layer 155-1, an HT-emission auxiliary layer 153-2-HT (hole transport layer), an emission layer 153-2-EM, an ET-emission auxiliary layer 153-2-ET, an electron transport layer 159-1, and a second electrode 190, wherein the HT-emission auxiliary layers include at least one second compound represented by Formula 2 (abstract; ¶ [0191]-[0200]; Fig. 3). Such a device obtains low driving voltage, high luminescent efficiency, and long lifespan (¶ [0183]).
Formula 2:
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75
270
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The modified compound 119 reads on Kim’s Formula 2 wherein: a11 to a13 are each 0; L11 to L13 are each not required to be present; R11 is a substituted C13 aryl group, R12 is a substituted C12 aryl group, and R13 is a substituted C25 arylene group; and b11 to b13 are each 1 (see Kim, ¶ [0007]).
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 compound 119 in the HT-emission auxiliary layers of Kim’s device, based on the teaching of Matsuki and Kim. The motivation for doing so would have been to use a compound with improved luminous efficiency and durability, as taught by Matsuki, and to provide a device with low driving voltage, high luminescent efficiency, and long lifespan, as taught by Kim.
Claims 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Matsuki (English translation of WO 2016009823 A obtained from Global Dossier) in view of Pflumm (US 2016/0190447 A1) and Fennimore (US 2017/0200893 A1) as applied to claim 6 above, and further in view of Zhen (US 2010/0117946 A1).
Regarding claims 13-14, Matsuki in view of Pflumm and Fennimore teach the device including the modified compound 119 as described above with respect to claim 6.
Matsuki fails to teach an electronic device comprising the device and a control unit.
Zhen teaches a brightness adjustable electrical apparatus comprising a lighting module and a control unit, wherein the control unit controls the brightness of the apparatus (abstract). The lighting module may be an organic light emitting diode (¶ [0006] and [0018]).
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 Matsuki’s device including the modified compound 119 as the light module in the brightness adjustable electrical apparatus of Zhen, because this would have been combining the prior art elements of Matsuki and Zhen according to known methods to yield predictable results of a brightness adjustable electrical apparatus with improved luminous efficiency and life durability, as taught by Matsuki. See MPEP 2143.I.(A).
Claims 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Matsuki (English translation of WO 2016009823 A obtained from Global Dossier) in view of Pflumm (US 2016/0190447 A1), Fennimore (US 2017/0200893 A1), and Kim (US 2017/0294587 A1) as applied to claim 6 above, and further in view of Zhen (US 2010/0117946 A1).
Regarding claims 13-14, Matsuki in view of Pflumm, Fennimore, and Kim teach the device including the modified compound 119 as described above with respect to claim 6.
Matsuki fails to teach an electronic device comprising the device and a control unit.
Zhen teaches a brightness adjustable electrical apparatus comprising a lighting module and a control unit, wherein the control unit controls the brightness of the apparatus (abstract). The lighting module may be an organic light emitting diode (¶ [0006] and [0018]).
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 device of Matsuki in view of Kim including the modified compound 119 as the light module in the brightness adjustable electrical apparatus of Zhen, because this would have been combining the prior art elements of Matsuki, Kim, and Zhen according to known methods to yield predictable results of a brightness adjustable electrical apparatus with improved luminous efficiency and life durability, as taught by Matsuki. See MPEP 2143.I.(A).
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached at 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/BRAELYN R WATSON/Examiner, Art Unit 1786