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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 09/12/2025 has been entered.
Summary of Claims
Claim 1 is amended due to Applicant's amendment dated 09/12/2025. Claims 1-5 and 9-14 are pending.
Election/Restrictions
As discussed in the previous rejection, Applicant elected Species A for each compound of the three or more compound each composed of centrally sp3 carbon, wherein the first and second compounds are of subspecies (a) (Formula 2, 3, or 4) and the third compound is of subspecies (d) (Formula 8 or 9).
However, as discussed below, this elected species is not anticipated or obvious over the prior art. Accordingly, the search was expanded to find an examinable species based on MPEP § 803.02. It is noted that the prior art search has not been extended to cover all nonelected species.
The next examinable species is: Species A for each compound of the three or more compound each composed of centrally sp3 carbon, wherein the first and second compounds are of subspecies (b) (Formula 5 or 6) and the third compound is of subspecies (d) (Formula 8 or 9). The examinable species reads on claims 1-5 and 9-14.
Response to Amendment
The rejection of claims 1-5 and 9-14 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 09/12/2025. The rejection is withdrawn.
The rejection of claims 1-4 under 35 U.S.C. 103 as being unpatentable over Parham (US 2018/0226587 A1) in view of Heo (WO 2017/146466 A1) and Ren (US 2004/0209116 A1) is overcome due to the Applicant’s amendment dated 09/12/2025. The rejection is withdrawn.
The rejection of claims 5, 11, and 13 under 35 U.S.C. 103 as being unpatentable over Parham in view of Heo, Ren and Hatakeyama (US 2015/0236274 A1) is overcome due to the Applicant’s amendment dated 09/12/2025. The rejection is withdrawn.
The rejection of claim 10 under 35 U.S.C. 103 as being unpatentable Parham in view of Heo, Ren and Tanaka (US 2016/0268516 A1) is overcome due to the Applicant’s amendment dated 09/12/2025. The rejection is withdrawn.
The rejection of claims 9 and 11-12 under 35 U.S.C. 103 as being unpatentable Parham in view of Heo, Ren and Seok (English translation of KR 20130118811 A obtained from Google Patents) is overcome due to the Applicant’s amendment dated 09/12/2025. The rejection is withdrawn.
The rejection of claim 14 under 35 U.S.C. 103 as being unpatentable Parham in view of Heo, Ren and Conley (US 2005/0211958 A1) is overcome due to the Applicant’s amendment dated 09/12/2025. The rejection is withdrawn.
However, as outlined below, new grounds of rejection have been made.
Response to Arguments
Insofar as the arguments apply to the new grounds of rejection outlined below, the Applicant’s arguments on pages 11-22 of the reply dated 09/12/2025 with respect to the rejection of claims 1-5 and 9-14 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –Applicant argues that the cited prior art references fail to teach the claims as amended. In the amendment, Ar2 of Formula 2 must be a substituted or unsubstituted heteroaryl group; R1 and R2 of Formula 2 may not be selected from a substituted or unsubstituted heterocyclic group; and R25 to R28 of Formula 8 do not include a substituted or unsubstituted phosphine oxide group.
Examiner's response –While the previously cited references fail to read on the amended claims, the newly cited reference Stoessel (US 2016/0308129 A1) teaches a compound of Formula 5 and the newly cited reference Gölfert (US 2018/0190922 A1) teaches a compound of Formula 8 wherein R25 to R27 are each hydrogen, and R28 is a phenyl group substituted with a diphenylphosphine oxide group. Accordingly, the cited references meet the claims as amended.
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 1-2, 4, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Stoessel (US 2016/0308129 A1) in view of Gölfert (US 2018/0190922 A1) and Ren (US 2004/0209116 A1), as evidenced by Ossila (Ossila, F4TCNQ, 2025).
Regarding claims 1-2, 4, and 14, Stoessel teaches organic electroluminescent device comprising compounds of formula (1), wherein the compounds represented by formula (1) have high thermal stability (abstract; ¶ [0007]-[0008]). Examples of devices comprising compounds represented by formula (1) include the device of E1 which includes an anode, a cathode, and the layer structure below between the anode and cathode (¶ [0198]; Table 2 on page 117).
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The combination of layers HIL2 and EBL reads on the claimed first organic material layer, and the layer ETL reads on the second organic material layer.
Stoessel is silent as to the band gap energy of F4TCNQ. However, Ossila teaches F4TCNQ has a HOMO of 8.3 eV and LUMO of 5.2 eV and thus has a band gap energy of 3.1 eV (see page 1).
HTM1 is reproduced below in comparison to the claimed Formula 5 (page 115).
HTM1:
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5:
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HTM1 reads on the claimed Formula 5 wherein:
R11 to R15 are each hydrogen and R16 is a substituted amine group; and
m11 to m15 are each 4 and m16 is 1.
Stoessel appears silent with respect to the band gap energy of HTM1.
The instant specification recites that the instant compound EB5 has a band gap energy of 3.41 eV (see Table 1 on instant page 427). Since Stoessel teaches HTM1, the same structure as the instant EB5 disclosed by the Applicant (see structure on instant page 420), HTM1 having a band gap energy of 3.41 eV is considered to be inherent (and would be expected to fall within the range in the claim), absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP 2112.
Stoessel’s ETL is formed of ETM and LiQ, and ETM fails to read on the claimed Formula 8 or Formula 9 (see structure on page 114 of Stoessel).
Gölfert teaches a device having improved electrical properties and including an improved transporting and/or electron injecting layer by comprising a silver cathode and an electron transporting layer which comprises a mixed layer of (i) at least one substantially covalent electron transport matrix compound comprising at least one polar group selected from phosphine oxide or diazole group, and (ii) in substantially elemental form, an electropositive element selected from specific metals (¶ [0001] and [0022]-[0024]). Examples of the electron transport matrix compound include E15 (¶ [0064]; structure on page 10).
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 Stoessel’s cathode with a silver cathode and to substitute Stoessel’s ETL with the electron transporting layer of Gölfert, based on the teaching of Gölfert. The motivation for doing so would have been to provide a device with improved electrical properties and provide an improved electron transporting layer, as taught by Gölfert.
Additionally, 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 E15 as the electron transport matrix, because it would have been choosing from a list of suitable electron transport matrices taught by Gölfert, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in the electron transport layer of the device of Stoessel in view of Gölfert and possessing the benefits taught by Gölfert. One of ordinary skill in the art would have been motivated to produce additional devices comprising the electron transport materials of Gölfert having the benefits taught by Gölfert in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
E15 is reproduced below in comparison to the claimed Formula 8.
E15:
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8:
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E15 reads on the claimed Formula 8 wherein:
R25 and R26 are each hydrogen;
R27 is hydrogen and R28 is a phenyl group substituted with a diphenylphosphine oxide group; and
m25 to m27 are each 4 and m28 is 1.
Gölfert is silent as to the band gap energy of E15. However, Zhao teaches spiro[fluorene-9,9’-xanthene] based compounds containing one or two diphenylphosphine oxide groups, wherein these compounds have energy gaps of 4.10 eV to 4.95 eV (see structure in Scheme 2 and energy gap value in Figure 2 on pg. 5334). As E15 is similarly a spiro[fluorene-9,9’-xanthene] based compound containing one diphenylphosphine oxide group, it is reasonable to presume that E15 has a band gap energy of 3 eV or more. The burden is upon the Applicant to prove otherwise. See MPEP 2112.
While the electron transporting layer of Gölfert additionally contains an electropositive element, this electropositive element is not required to have a band gap within the claimed range because it is not an organic material.
Stoessel is silent as to the band gap energy of the host compound H1 in the EML.
Ren teaches wide gap host materials for use in fluorescent or phosphorescent emissive layers of organic light emitting devices, wherein the energy gap is preferably at least 3.2 eV (abstract; ¶ [0059] and [0081]). By selecting a wide gap host material, the host material does not quench the dopant emission by endothermic or exothermic energy transfer which allows for improved quantum efficiencies (¶ [0008] and [0080]).
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 modify the host compound H1 (for example, by introducing additional substituent groups) such that it obtains an energy gap of at least 3.2 eV, and thus is considered a wide gap host material, based on the teaching of Ren. The motivation for doing so would have been to prevent the quenching of the dopant emission by endothermic or exothermic energy transfer and thereby provide improved quantum efficiency, as taught by Ren.
The modified host compound H1 is an anthracene-based compound (see structure on page 114 of Stoessel) (claim 14).
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Stoessel (US 2016/0308129 A1) in view of Gölfert (US 2018/0190922 A1) and Ren (US 2004/0209116 A1) as applied to claim 1 above, and further in view of Cha (US 2019/0389810 A1).
Regarding claim 3, Stoessel in view of Gölfert and Ren teach the organic electroluminescent device comprising the layers HIL2 and EBL (which each include the compound HTM1) and the layer ETM comprising E15, as described above with respect to claim 1.
E15 fails to include a nitrogen-containing ring, as required by claim 3.
Cha teaches an organic light emitting device having improved efficiency, driving voltage, and lifetime characteristics by including therein a cyclic compound represented by Chemical Formula 1 (abstract). Cha teaches examples of such devices including the device of Example 2-1 wherein the electron transport layer includes Compound 1 (see Table 2 on page 88).
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 provide Compound 1 in the ETL of the device of Stoessel in view of Gölfert and Ren, as shown in Cha’s Example 2-1, based on the teaching of Cha. The motivation for doing so would have been to provide a device with improved efficiency, driving voltage, and lifetime characteristics, as taught by Cha.
Compound 1 is reproduced below in comparison to the claimed Formula 6 (see structure on pg. 65 of Cha).
1:
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6:
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Compound 1 reads on the claimed Formula 6 wherein:
R103 and R104 are each an unsubstituted alkyl group;
R17 to R19 are each hydrogen and R20 is a substituted aryl group; and
m17 to m19 are each 4 and m20 is 1.
Cha appears silent with respect to the band gap energy of Compound 1
The instant specification recites that instant compounds HB2, HB3, ET4, and ET5 each have band gap energy values of 3 eV or more (see structures on instant pages 420-421 and values in Table 1 on instant page 427). Since Cha teaches Compound 1, a compound substantially similar to instant compounds HB2, HB3, ET4, and ET5, Compound 1 having a band gap energy of 3 eV or more is considered to be inherent (and would be expected to fall within the range in the claim), absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP 2112.
Per claim 3, the claimed first organic material layer comprises two compounds composed of centrally sp3 carbon that each on the claimed Chemical Formula 5 comprising a substituted amine group (HTM1), and the claimed second organic material layer comprises one compound composed of centrally sp3 carbon that reads on the claimed Chemical Formula 6 comprising a substituted nitrogen-containing aromatic polycyclic ring (Compound 1).
Claims 5, 11, and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Stoessel (US 2016/0308129 A1) in view of Gölfert (US 2018/0190922 A1) and Ren (US 2004/0209116 A1) as applied to claim 1 above, and further in view of Hatakeyama (US 2015/0236274 A1)
Regarding claims 5, 11, and 13, Stoessel in view of Gölfert and Ren teach the organic electroluminescent device comprising SEB as a dopant in the EML, as described above with respect to claim 1.
SEB fails to be a boron-based compound (see structure on page 114 of Stoessel). However, Stoessel teaches the device may be a fluorescent OLED (¶ [0006]).
Hatakeyama teaches a novel polycyclic aromatic compound for use as a fluorescent material that provides an excellent organic EL element, wherein the polycyclic aromatic compound is represented by general formula (1) (¶ [0013], [0033], and [0046]). Hatakeyama teaches a specific example of a device in Example 1 wherein Compound (1-176) is used as a dopant material (¶ [0550] and pg. 4).
general formula (1):
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formula (1-176):
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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 substitute the dopant SEB with a compound of Hatakeyama’s general formula (1), and particularly formula (1-176) as shown in Hatakeyama’s Example 1, to obtain an excellent organic EL element, as taught by Hatakeyama.
Hatakeyama teaches a device comprising formula (1-176) as a dopant has a maximum wavelength emission of 437 nm (¶ [0553]) (claim 5).
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Stoessel (US 2016/0308129 A1) in view of Gölfert (US 2018/0190922 A1) and Ren (US 2004/0209116 A1) as applied to claim 1 above, and further in view of Tanaka (US 2016/0268516 A1).
Regarding claim 10, Stoessel in view of Gölfert and Ren teach the organic electroluminescent device comprising the modified H1 as a host in the EML, as described above with respect to claim 1.
Stoessel fails to teach the EML comprises two host compounds.
Tanaka teaches hosts may be used singly or used in combination of two or more compounds (¶ [0190]). By using plural host compounds, it is possible to adjust transfer of charge and thereby obtain high efficiency in the organic EL device (¶ [0190]).
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 provide an additional host compound in the EML, as taught by Tanaka, wherein the additional host compound has an energy gap of at least 3.2 eV, as taught by Ren. The motivation for doing so would have been to adjust transfer of charge and thereby obtain high efficiency in the organic light emitting device, as taught by Tanaka, and to prevent the quenching of the dopant emission by endothermic or exothermic energy transfer and thereby provide improved quantum efficiency, as taught by Ren.
Claims 9 and 11-12 are rejected under 35 U.S.C. 103 as being unpatentable over Stoessel (US 2016/0308129 A1) in view of Gölfert (US 2018/0190922 A1) and Ren (US 2004/0209116 A1) as applied to claim 1 above, and further in view of Seok (English translation of KR 20130118811 A obtained from Google Patents).
Regarding claims 9 and 11-12, Stoessel in view of Gölfert and Ren teach the organic electroluminescent device comprising SEB as a dopant in the EML, as described above with respect to claim 1.
SEB fails to comprise two or more substituted or unsubstituted amine groups.
Seok teaches a novel compound represented by formula (1) that greatly improves the lifespan, efficiency, electrochemical stability, and thermal stability of an organic light emitting device, wherein the compound represented by formula (1) may be used as a light emitting material (¶ [0008], [0019], and [0025]). Seok teaches compounds 1 to 12 are examples of compounds represented by formula (1) (¶ [0056] and pgs. 8-9). As seen on pgs. 8-9, compounds 1 to 12 are all compounds composed of centrally sp3 carbon comprising two substituted amine groups.
formula (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 substitute the dopant SEB in the EML with a compound of Seok’s formula (1), and particularly one of compounds 1 to 12, to greatly improve the lifespan, efficiency, electrochemical stability, and thermal stability of the device, as taught by Seok.
As seen on pgs. 8-9, compounds 1 to 12 are fluorescent dopants each composed of centrally sp3 carbon comprising two substituted amine groups.
Allowable Subject Matter
In the reply filed 05/20/2024, Applicant elected Species A for each compound of the three or more compounds each composed of centrally sp3 carbon, wherein the first and second compounds are of subspecies (a) (Formula 2, 3, or 4) and the third compound is of subspecies (d) (Formula 8 or 9). The elected species reads on claims 1-5 and 9-14.
With regard to the instant claim 1 only, a search of the prior art did not show the elected species. As none of the claims were specifically drawn to the elected species in combination with the limitations of claim 1 in independent form, none of these claims have been indicated as allowable. However, claim 1 written in independent form which requires all the limitations of claim 1 as well as being limited to the elected species along with any dependent claims which require all the limitations of claim 1 as well as being limited to the elected species would be allowable.
Claims 2-5 and 9-14 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims as well as being limited to the elected species. This objection to the claims is only with respect to the elected species.
It is noted that the potential allowability of claims 1-5 and 9-14 has not be determined with respect to species beyond the elected species, i.e. potential examinable species that could found once the search is expanded beyond the elected species.
The following is a statement of reasons for the indication of allowable subject matter:
With respect to claim 1 and the elected Species A for each compound of the three or more compound each composed of centrally sp3 carbon, wherein the first and second compounds are of subspecies (a) (Formula 2, 3, or 4) and the third compound is of subspecies (d) (Formula 8 or 9), the prior art does not teach or suggest an organic light emitting device comprising a light emitting layer; a first organic material layer comprising one or more compounds each composed of centrally sp3 carbon; a second organic material layer one or more compounds each composed of centrally sp3 carbon; wherein among organic materials included in the light emitting layer, the first organic material layer, and the second organic material layer, the band gap energy of each of the organic materials except for a dopant compound is 3 eV or more; wherein the first organic material layer and the second organic material layer comprise a total of three or more compounds each composed of centrally sp3 carbon; and wherein in the three or more compounds composed of centrally sp3 carbon, the first and second compounds are of subspecies (a) (Formula 2, 3, or 4) and the third compound is of subspecies (d) (Formula 8 or 9), in combination with the remainder of claim 1.
Parham (US 2018/0226587 A1), cited in the previous rejection dated 06/12/2025, is considered the closest prior art of record. Parham teaches fluorene derivatives represented by formula (I) and/or (II) which provide electronic devices with improved lifetime (abstract; ¶ [0148] and [0165]). Parham teaches examples of such devices including I11 comprising an anode, a hole transport layer (ETL), an interlayer (IL), an electron blocking layer (EBL) comprising SpMA1, and emission layer (EML) comprising host IC1 and dopant TEG1, a hole blocking layer (HBL) comprising IC1, an electron transport layer (ETL) comprising ST2 and 44e, and a cathode (¶ [0207] and [0212]; and Table 1 on pg. 136). The EBL reads on the claimed first organic material layer, and the combination of layers HBL and ETL read on the second organic material layer.
As discussed above, the EBL comprises SpMA1 and the ETL comprises ST2 and 44e (see Parham, pg. 137).
SpMA1:
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44e:
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SpMA1 fails to read on the claimed Formula 2 as it does not comprise a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms in the location of the claimed Ar2. Additionally, 44e fails to read on the claimed Formula 2 because the claimed R1 cannot be a substituted or unsubstituted heterocyclic group.
Accordingly, Parham fails to teach three or more compounds each composed of centrally sp3 carbon, wherein the first and second compounds are of subspecies (a) (Formula 2, 3, or 4). Additionally, Parham fails to teach a third compound composed of centrally sp3 carbon that is of subspecies (d) (Formula 8 or 9).
Gölfert (US 2018/0190922 A1), cited in the rejection above, is considered relevant to the claimed invention. Gölfert teaches a device having improved electrical properties and including an improved transporting and/or electron injecting layer by comprising a silver cathode and an electron transporting layer which comprises a mixed layer of (i) at least one substantially covalent electron transport matrix compound comprising at least one polar group selected from phosphine oxide or diazole group, and (ii) in substantially elemental form, an electropositive element selected from specific metals (¶ [0001] and [0022]-[0024]). Examples of the electron transport matrix compound include E15 (¶ [0064]; structure on page 10).
E15:
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However, Gölfert fails to teach three or more compounds each composed of centrally sp3 carbon, wherein the first and second compounds are of subspecies (a) (Formula 2, 3, or 4). Accordingly, Gölfert fails to remedy the deficiencies of Parham.
Thus there is no prior art, either alone or in combination, which teaches or renders obvious an organic light emitting device comprising a light emitting layer; a first organic material layer comprising one or more compounds each composed of centrally sp3 carbon; a second organic material layer one or more compounds each composed of centrally sp3 carbon; wherein among organic materials included in the light emitting layer, the first organic material layer, and the second organic material layer, the band gap energy of each of the organic materials except for a dopant compound is 3 eV or more; wherein the first organic material layer and the second organic material layer comprise a total of three or more compounds each composed of centrally sp3 carbon; and wherein in the three or more compounds composed of centrally sp3 carbon, wherein the first and second compounds are of subspecies (a) (Formula 2, 3, or 4) and the third compound is of subspecies (d) (Formula 8 or 9), in combination with the remainder of claim 1.
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