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 .
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. EP 22192918.5, filed on 08/30/2022.
The certified copy has been filed in parent Application No. EP 22177214.8, filed on 06/03/2022.
The certified copy has been filed in parent Application No. EP 22177215.5, filed on 06/03/2022.
Specification
The disclosure is objected to because of the following informalities: The instant specification filed on 07/25/2023 is missing paragraph numbers. It is therefore difficult to cite the instant specification. Appropriate correction is required.
Claim Objections
Claims 1, 3, and 10–11 objected to because of the following informalities:
Claims 1, 3, and 11 recite both “halogen” and “Cl, F” which is redundant.
In Claims 1 and 3 it is suggested to insert “the” before the second iteration of “at least one charge generation layer.”
In Claim 10 it is suggested to insert “in” as following: “wherein in the compound of formula (IIa), Ring A is selected from.”
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1–15 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 1 and 3 recites the limitation "the organic semiconductor layer is closer to the anode layer than the p-type charge generation layer". This is the first mention of an organic semiconductor layer, therefore there is insufficient antecedent basis for this limitation in the claim.
Claim 2 recites “the compound of formula (II) the necessary rearrangement of double bonds results in at least a partial lift of aromaticity in the annelated aromatic system or non-annelated aromatic system.”
The claims and the instant specification do not provide a Formula (II). The instant specification has provided no guidance about what a partial lift of aromaticity is. Therefore, it is unclear how a compound would have a partial lift of aromaticity.
For the purposes of examination, a compound of Formula (II) will be interpreted as a quinoid compound which contains a moiety which is (formally) derived from a compound comprising an annelated aromatic system or non-annelated aromatic system whereby an even number of carbon atoms of said annelated aromatic system or non-annelated aromatic system are double bonded to an atom or a group outside said annelated aromatic system or non-annelated aromatic system.
Claims 2, 4–9, 11–15 are rejected as being dependent on indefinite claim 1.
Claim 10 is rejected as being dependent on indefinite claim 3.
Claims 1–15 are rejected under 35 U.S.C. 103 as being unpatentable over Senkovskyy et al. (US 2018/0337339 A1, hereinafter “Senkovskyy”) in view of Hummert et al. (US 2017/0373251 A1, provided in Applicant’s IDS filed on 07/25/2023, hereinafter “Hummert”) and Zeika et al. (US 2017/0012203 A1, hereinafter “Zeika”), supporting information provided by CAS Registry Number: 1096703-53-5.
Regarding Claims 1–15, Senkovskyy teaches a tandem OLED including an anode, a first hole injection layer (HIL), a first hole transport layer, a first electron blocking layer, a first emission layer, a first hole blocking layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer (p-type CGL), a second hole transport layer, a second electron blocking layer, a second emission layer, a second hole blocking layer, a second electron transport layer, a second electron injection layer, and a cathode ([0259], [0337] – [0342], and Fig. 3).
Regarding the first hole injection layer, Senkovskyy teaches a hole injection layer comprises 92 wt.-% of Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine and 8 wt.-% of 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) [0340]. In this case, 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) is acting as a p-dopant [0110]. Senkovskyy further teaches the hole injection layer may be formed of any compound that is commonly used to form an HIL [0109]. The HIL may be selected from a hole-transporting matrix compound doped with a p-dopant [0110].
However, 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl) acetonitrile) appears to not have a LUMO energy level ≤ -5.20 eV.
Hummert teaches compounds of formula (I) which may be used in a layer adjacent to the anode in an OLED [0016] – [0019]. Specifically, Hummert teaches Compound A6 (shown below) [0041]. Hummert further teaches the compounds of Hummert’s formula (I) may be used instead of state-of-art p-dopants since they have a larger redox potential and therefore may be used in lower concentration. This allows for additional degrees of freedom for designers of electronic devices since the optical absorption of the doped layers will be smaller in comparison with state-of-art p-dopants [0039].
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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 have modified the tandem OLED taught by Senkovskyy by substituting Compound A6, as taught by Hummert, for 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) as the p-type dopant in the hole injection layer. One would have been motivated to do so because Senkovskyy teaches the hole injection layer may comprise a p-type dopant of any conventional material and Hummert teaches the compounds of formula (I) for use as a dopant in the hole injection layer of an OLED. The selection of a known material, which is based upon its suitability for the intended use, is within the ambit of one of ordinary skill in the pertinent art. See MPEP § 2144.07.
Additionally, Hummert teaches the compounds of formula (I) may be used instead of state-of-art p-dopants since they have a larger redox potential and therefore may be used in lower concentration and therefore one of ordinary skill in the art would be motivated to form the p-type dopant out of a compound of formula (I), as taught by Hummert, in the device of Senkovskyy, as it would yield an OLED with a lower optical absorption of the doped layers in comparison with state-of-art p-dopants.
It would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select Compound A6 as the p-dopant, because it would have been choosing between compounds A1–A8 and B1–B10, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the p-dopant in the hole injection layer of the OLED of Senkovskyy and possessing the benefits taught by Hummert. One of ordinary skill in the art would have been motivated to produce additional devices comprising Compound A6 having the benefits taught by Hummert in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Regarding the p-type charge generation layer, Senkovskyy teaches the p-type charge generation layer comprises 92 wt.-% of Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine and 8 wt.-% of 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) [0342].
While 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl) acetonitrile) does not read on Applicant’s formula (II), Senkovskyy teaches the p-type dopant and host used for organic material doped with the p-type dopant can employ conventional materials, wherein examples of the p-type dopant can be selected from a derivative of tetracyanoquinodimethane [0188].
Zeika teaches quinoid compounds which may be used as a p-dopant in semiconductive matrix materials (abstract and [0024]). Specifically, Zeika teaches Compound 1 (shown below) [0045]. Zeika further teaches the quinoid compounds may be used to produce a p-doped organic semi-conductor material which may be used in the electronic conduction paths of a plurality of electronic structural elements. The electrical conductivity, light-emitting properties or the like can be advantageously changed by using the described compounds [0028].
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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 have modified the tandem OLED taught by Senkovskyy by substituting Compound 1, as taught by Zeika, for 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) as the p-type dopant in the p-type charge generation layer. One would have been motivated to do so because Senkovskyy teaches the p-type charge generation layer may comprise a p-type dopant of any conventional material and Zeika teaches the quinoid compounds for use as a dopant in the p-doped organic semiconductor layer of an OLED. The selection of a known material, which is based upon its suitability for the intended use, is within the ambit of one of ordinary skill in the pertinent art. See MPEP § 2144.07.
Additionally, Zeika teaches the compounds provide advantageous electrical conductivity and light-emitting properties when used in a p-doped organic semiconductor layer of an OLED and therefore one of ordinary skill in the art would be motivated to form the p-type dopant out of the quinoid compounds, as taught by Zeika, in the device of Senkovskyy, as it would yield an OLED with advantageous electrical conductivity and light-emitting properties.
Per Claims 1–3, the resulting OLED (hereinafter “Device 1”) includes an anode, a first hole injection layer (HIL), a first hole transport layer, a first electron blocking layer, a first emission layer, a first hole blocking layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer (p-type CGL), a second hole transport layer, a second electron blocking layer, a second emission layer, a second hole blocking layer, a second electron transport layer, a second electron injection layer, and a cathode, wherein the hole injection layer comprises 92 wt.-% of Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine (hole transport matrix compound) and 8 wt.-% of Compound A6 which reads on Applicant’s Formula (I) (shown below),
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wherein:
A1 is represented by Formula (Ia) wherein:
Ar1 is a C5 heteroaryl substituted with three F atoms and one perfluorinated C1 alkyl (trifluoromethyl).
R’ is CN,
A2 is represented by Formula (Ib) wherein:
Ar2 is a C5 heteroaryl substituted with three F atoms and one perfluorinated C1 alkyl (trifluoromethyl).
R’ is CN,
A3 is represented by Formula (Ic) wherein:
Ar3 is a C5 heteroaryl substituted with three F atoms and one perfluorinated C1 alkyl (trifluoromethyl).
R’ is CN.
Hummert appears silent with respect to the property of LUMO energy level of Compound A6.
The instant specification recites that Compound A1 has a LUMO energy level of -5.29 eV [Table 2]. Since Hummert teaches Compound A6, the same structure as disclosed by the Applicant, the property of LUMO energy level 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.
The p-type charge generation layer of Device 1 comprises Compound 1 which reads on Applicant’s Formula (II) since it is a quinoid compound containing a moiety comprising a non-annelated aromatic system whereby two carbon atoms of the non-annelated aromatic system are double bonded to a group outside the non-annelated system.
Compound 1 also reads on Applicant’s Formula (IIa) (shown below),
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wherein:
X1 and X2 are each represented by CR1aR2a wherein R1a is CN and R2a is a C6 aryl group, substituted with four F atoms and one CN group,
n is 0 and thus X3 is not required to be present,
Ring A is represented by
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wherein R1 and R2 are each represented by F while R3 and R4 are represented by CN.
Per Claim 4, Device 1 comprises an n-type charge generation layer.
Per Claim 5, R’ is represented by CN in Compound A6.
Per Claim 6, Ar1, Ar2, and Ar3 are each represented by
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in Compound A6.
Per Claim 7, Compound 1 has a molecular weight of 586.3 g/mol as evidenced by CAS Registry Number: 1096703-53-5 (provided in this Office Action).
Per Claim 8, Zeika appears silent with respect to the property of the LUMO energy level of Compound 1.
The instant specification recites that Compound Q6 has a LUMO energy level of -5.21 eV [Table 1]. Since Zeika teaches Compound 1, the same structure as disclosed by the Applicant, the property of LUMO energy level 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 9, Compound 1 contains two C6 aryl groups each substituted with four F atoms and one CN group.
Per Claims 10 and 12–14, Ring A is represented by
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in Compound 1.
Per Claim 11, Compound 1 reads on Applicant’s Formula (IIc) (shown below),
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wherein:
X1 and X2 are each represented by CR1aR2a wherein R1a is CN and R2a is a C6 aryl group, substituted with four F atoms and one CN group,
n is 0 thus X3 is not required to be present,
Ring A is represented by
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wherein R1 and R2 are each represented by F while R3 and R4 are represented by CN.
Per Claim 15, Senkovskyy teaches one aspect of present invention is directed to a device comprising at least one organic electroluminescent device (OLED) such as a display or a lighting panel [0087].
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Cui et al. (US 2020/0062778 A1, provided in Applicant’s IDS filed on 07/25/2023) discloses compounds which read on Applicant’s Formula (IIa).
Lederer et al. (US 2020/0032093 A1) discloses compounds which read on Applicant’s Formula (IIa).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JAMES RICHARD FORTWENGLER whose telephone number is (571)272-5433. The examiner can normally be reached Monday - Friday, 8 am - 5 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Marla McConnell can be reached at (571) 270-7692. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/J.R.F./Examiner, Art Unit 1789
/BRAELYN R WATSON/Primary Examiner, Art Unit 1786
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