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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 05/27/2026 has been entered.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1, 3-5, 8, 10-11, 24-30 and 32-36 are rejected under 35 U.S.C. 103 as being unpatentable over Voges et al (US 2017/0331053) (Voges).
In reference to Claims 1, 3-5, 11 and 24, Voges teaches compounds of formula A as shown below for an organic light emitting diode (abstract, [0014]-[0029])
PNG
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82
390
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Greyscale
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182
340
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Greyscale
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218
428
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Greyscale
for example, wherein in the formula A, one group A1 is Ar1-41, and the other two groups A1 are Ar1-73 as shown above (Voges [0036]).
Voges discloses the compound of formula A that encompasses the presently claimed compound of formula (1), including wherein in the formula A, one group A1 is Ar1-41, and the other two groups A1 are Ar1-73 as shown above. Each of the disclosed substituents from the substituent groups of Voges are considered functionally equivalent and their selection would lead to obvious variants of the compound of formula A.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application, in the absence of unexpected results, to have selected these substituents among those disclosed for the compound of formula A to provide the compound described above, which is both disclosed by Voges and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
For Claim 1: Reads on a compound of formula (1) wherein L is a single bond to R24, R21 to R23 and R25 to R28 are each hydrogen, R31 to R34 are each hydrogen, R41 to R42 and R44 to R45 are each hydrogen, R43 is bonded to R56, R51 to R55 and R57 to R58 are each hydrogen, R61 bonds to Ar, R63 is phenyl, R62 to R66 are each hydrogen, Ar is represented by formula (4) wherein bonded at R78, and R71 to R78 are each hydrogen.
For Claim 3: Reads on formula 1-a.
For Claim 4: Reads on formula 1-a-1.
For Claim 5: Reads on formula 1-a-2.
For Claim 11: Reads on hydrogen.
For Claim 24: Reads on a material.
In reference to claim 8, the claim further limits the unsubstituted aryl group of various R groups, which is an optional embodiment of claim 1 (i.e. R is selected from a hydrogen atom…) and therefore not required. As such, claim 8 is rejected based on similar reasons to claim 1.
In reference to claim 10, the claim further limits the alkyl groups, which is an optional embodiment of claim 1 (i.e. R# are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group…) and therefore not required. As such, claim 10 is rejected based on similar reasons to claim 1.
In reference to claim 25 to 30 and 32, Voges teaches the compound as described above for claim 1. Voges further teaches that this compound is used in an organic light emitting device comprising an anode, a cathode, and an organic material layer between wherein the organic material layer includes a hole injection layer, a hole transport layer, a light emitting layer among others and wherein the compound is included in the hole transport layer (Voges [0083] to [0093]; [0079]) and wherein the emitting layer comprises a fluorescent material and exemplifies several fluorescent dopants (Voges [0110] to [0114]).
While Voges does not exemplify a device with this specific material in the hole transport layer as claimed, it would have been immediately obvious to the ordinarily skilled artisan to have used the material of Voges in the application of Voges with the anticipation of providing a device having similar functionality to that of the devices exemplified therein.
In reference to claim 33, Voges teaches the compound as described above for claim 1. This compound is merely a positional isomer of the instantly claimed compounds and Vogues in no way requires this positional isomer.
Furthermore, it is noted that compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). In light of the case law cited above, it therefore would have been obvious to one of ordinary skill in the art that the compound disclosed in the present claims is but an obvious variant of the compound presently claimed, and thereby one of ordinary skill in the art would have arrived at the claimed invention.
In reference to claim 34, Voges teaches the compound as described above for claim 1. Voges further teaches that the group A1 can alternatively be substituted instead of a substituted phenyl biphenyl group such as that claimed wherein substituents can include dibenzothiophene groups (Voges [0021] [0025] [[049]).
Voges discloses the compound of formula 1 that encompasses the presently claimed compounds, including wherein A1 can alternatively be substituted a biphenyl group such as those claimed wherein substituents can include dibenzothiophene groups. Each of the disclosed substituents from the substituent groups of Voges are considered functionally equivalent and their selection would lead to obvious variants of the compound of formula 1.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application, in the absence of unexpected results, to have selected these biphenylene instead of phenylene to provide the claimed compound, which is both disclosed by Voges and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
In reference to claim 35, the claim further limits the unsubstituted aryl group of various R groups, which is an optional embodiment of claim 34 (i.e. R is selected from a hydrogen atom…) and therefore not required. As such, claim 8 is rejected based on similar reasons to claim 1.
In reference to claim 36, the claim further limits the alkyl groups, which is an optional embodiment of claim 34 (i.e. R# are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group…) and therefore not required. As such, claim 10 is rejected based on similar reasons to claim 1.
Claim 23 are rejected under 35 U.S.C. 103 as being unpatentable over Voges et al (US 2017/0331053) (Voges) in view of Hwang et al (US 2009/0295274) (Hwang).
In reference to claim 23, Voges teaches the compound as described above for claim 1.
Voges does not expressly teach that the hole transport compounds should comprise deuterium atoms as claimed.
With respect to the difference, Hwang teaches, in analogous art, that partial or full deuteration of protons of semiconducting organic compounds, high voltage stability of the devices can be increased, turn on voltage can be decreased and therefor a usage lifetime can be prolonged efficiently (Hwang [0025]).
In light of the motivation of using partial deuteration as described above, it would therefore have been obvious to one of ordinary skill in the art before the effective filing date of the instant application to use the partial deuteration as described by Hwang in order to increase stability, decreased turn on voltage and prolong device lifetime and thereby arrive at the claimed invention.
Response to Arguments
Applicant's arguments filed 05/27/2026 have been fully considered but they are not persuasive.
In reference to the outstanding rejections under 35 USC 103 over Voges, Applicant initially argues that the prior art fails to exemplify compounds that have two naphthyl substituents that do not “have significantly different structures from the claims”. This argument is not convincing. An example is not required for a rejection under 35 USC 103. Voges teaches the specific preferred groups Ar-73 and Ar-44 as pointed to above herein in a short and finite list of options. The selection among a few preferred options results in an obvious selection to arrive at the instantly claimed materials.
Applicant further argues that the compounds of the instant claims give rise to unexpected results in comparison with the prior art of record as evidenced by data from the instant specification and additional results presented in the form of a declaration under 37 CFR 1.132. This argument has been fully considered and not found convincing for at least the following reasons.
For a finding of unexpected results, the results presented need to be of both statistical and practical significance and be commensurate in scope with the subject matter claimed (See MPEP 716.02).
First, while the inventive examples allegedly show improvements in device lifetime, the specification has provided no information that would allow the analysis of the statistical significance of the results. That is, while Applicant has attested that each condition was conducted three times ‘without significant variance” there is no information on the size of variance to evaluate if the data is significant or not. A mere attestation that Applicant thinks it is significant is insufficient.
Second, it is not immediately obvious that the improvements in device lifetime are unexpected. Voges teaches several example devices comprising materials described therein and demonstrates that depending on the material selected within a given device configuration, large lifetime differences are expected from one material to another. It is not clear that Applicant has really found something unexpected because different materials in a single device configuration give rise to different lifetime values (see Voges examples tables 1 and 3).
Third, the showing of the results of a few examples is not commensurate in scope with the very large number of compounds encompassed by the instant claims. For example, each of the R groups can be selected from alkyl groups having 1 to 18 carbon atoms. There are, once bonding is accounted for, over 30 positions that can each be hydrogen or one of these alkyl groups. Given the structural variation from 1 to 10 carbon atoms, each position can be selected from well over 1000 structures This results in the alkyl group substation options alone accounting for greater than 10100 different chemical compounds without accounting for the many possible positional isomer combinations for bonding between phenyl, naphthyl, dibenzofuranyl groups that are present in the instant claim 1. Applicant has demonstrated only 3 compounds, none of which have an alkyl group present at any of those positions. Data for 3 compounds is not considered commensurate in scope with the >> 10100 compounds that are instantly claimed. These examples are not intended to be interpreted as the only points in which the data is not commensurate in scope with the claims but merely to illustrate how the breadth of the claimed compounds is much larger than that set forth in the examples, these variables resulting in claiming thousands of more compounds and even more devices. As Applicant is attesting that the claimed compounds have properties that would not be expected based on the genus as a whole, for example compounds taught by Voges, support for the unexpected results must be provided that covers the scope of what is claimed.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Sean M DeGuire whose telephone number is (571)270-1027. The examiner can normally be reached Monday to Friday, 7:00 AM - 5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer A. 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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/Sean M DeGuire/Primary Examiner, Art Unit 1786
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