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 22192927.6, filed on 08/30/2022.
The certified copy has been filed in parent Application No. EP 22177215.5, filed on 06/03/2022.
The certified copy has been filed in parent Application No. EP 22177214.8, 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 16, 22, 27, 29, and 32 objected to because of the following informalities:
In Claims 16 and 22 it is suggested to insert “the” before the second iteration of “at least one charge generation layer.”
In Claim 27 it is suggested to insert “wherein” before “the compound of formula (II).”
In Claim 29 it is suggested to insert “in” in the following location: “wherein in the compound of formula (IIa), Ring A is selected from.”
Claims 16, 22, and 32 recites both “halogen” and “Cl, F”, which is redundant.
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 16–21, 23–28, 30–31, and 34 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 16 and 21 recite “the compound of formula (II) is a 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 with any necessary rearrangement of double bonds and resulting in at least a partial lift of aromaticity in the annelated aromatic system or non-annelated aromatic system.”
There is no provided formula (II) in the claims or the instant specification. The instant specification has provided no guidance to what the necessary rearrangement of double bonds entails. Therefore, it is unclear how a compound would meet the limitation of the necessary rearrangement of double bonds. Additionally, 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. The only mention of these limitations in the instant specification is on page 8, which essentially recites the claimed limitation with no further guidance.
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 17–20, 23–28, and 34 are rejected as being dependent on indefinite claim 16.
Claims 30 and 31 lack antecedent basis since both recite “the at least one aryl substituent” and “the at least one heteroaryl substituent.” However, claim 22 does not actually recite an aryl or heteroaryl substituent.
For the purposes of examination, claims 30 and 31 will be interpreted as “whereby in formula (IIa) at least one of R1 to R8 is selected from.”
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 16–34 are rejected under 35 U.S.C. 103 as being unpatentable over Senkovskyy et al. (US 2018/0337339 A1, hereinafter “Senkovskyy”) in view of Cui et al. (US 2020/0062778 A1, provided in Applicant’s IDS filed on 07/25/2023, hereinafter “Cui”), supporting information provided by CAS Registry Number: 2412173-78-3 and CAS Registry Number 1224447-88-4.
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] and Fig. 3). Senkovskyy teaches the p-type CGL may comprise 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], wherein 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) reads on Applicant’s formula (I) as described below.
While Senkovskyy teaches 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 and 8 wt.-% of 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) [0340], Senkovskyy fails to teach a hole injection layer that comprises a compound of Applicant’s Formula (II). However, Senkovskyy does teach the HIL may be selected from a hole-transporting matrix compound doped with a p-dopant, wherein examples of the p-dopant include 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) [0110]
Cui teaches compounds which offer greatly improved voltage and lifetime when used in the hole injection layer of an OLED ([0013] and [0036]). Cui teaches the hole injection layer comprises a compound of Formula 1’ [0037], exemplified by Compound 70 (shown below) [0258]. Cui further teaches the hole injection layer is formed from a hole transport material and a dopant [0134]. Additionally, Cui discloses Device Example 6.3 wherein the hole injection layer comprises Compound 70 as a p-type dopant and Compound HT1 as a hole transporting material ([0284] – [0286] and Table 5).
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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 70, as taught by Cui, 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 Cui teaches the compounds of Formula 1’ 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, Cui teaches the compounds provide greatly improved voltage and lifetime when used in a hole injection layer of an OLED and therefore one of ordinary skill in the art would be motivated to form the p-type dopant out of a compound of Formula 1’, as taught by Cui, in the device of Senkovskyy, as it would yield an OLED with improved voltage and lifetime.
Per Claims 16, 21–22, and 34, 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 p-type CGL 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 2,2′,2″-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) (hereinafter “p-dopant 1”). The structure of p-dopant 1 is provided in CAS Registry Number: 1224447-88-4 (provided in this Office Action). p-dopant 1 reads on Applicant’s Formula (I) (shown below),
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wherein:
A1 is represented by Formula (Ia) wherein:
Ar1 is a C6 aryl substituted with four F atoms and one CN group,
R’ is CN,
A2 is represented by Formula (Ib) wherein:
Ar2 is a C6 aryl substituted with four F atoms and one CN group,
R’ is CN,
A3 is represented by Formula (Ic) wherein:
Ar3 is a C6 aryl substituted with four F atoms and one CN group,
R’ is CN.
The hole injection layer of Device 1 comprises 92 wt.-% of Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine as a second hole transport matrix compound and 8 wt.-% of Compound 70 ([0257] and Table 3). Compound 70 reads on Applicant’s Formula (II) since it contains a moiety comprising an annelated aromatic system whereby two carbon atoms of the annelated aromatic system are double bonded to a group outside the annelated system.
Compound 70 also reads on Applicant’s Formula (IIa) (shown below),
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wherein:
X1 and X2 are each represented by CR1aR2a wherein R1a and R2a are each CN,
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 a C6 aryl (phenyl) substituted with two perfluorinated C1 alkyl groups (trifluoromethyl).
Per Claims 17–19, Compound 70 contains two C6 aryl groups (phenyl).
Per Claim 23, Device 1 comprises an n-type charge generation layer.
Per Claim 24, each R’ in p-Dopant 1 is represented by CN.
Per Claim 25, Senkovskyy appears silent with respect to the LUMO energy level of p-Dopant 1.
The instant specification recites that Compound A2 has a LUMO energy level of -5.19 eV [Table 2]. Since Senkovskyy teaches p-Dopant 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 26, Ar1, Ar2, and Ar3 are each represented by
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in p-Dopant 1.
Per Claim 27, Compound 70 has a molecular weight of 710.39 g/mol as evidenced by CAS Registry Number: 2412173-78-3 (provided in this Office Action).
Per Claim 28, Cui appears silent with respect to the LUMO energy level of Compound 70.
The instant specification recites that Compound QE-3 has a LUMO energy level of -5.35 eV [Table 1]. Since Cui teaches Compound 70, 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 29, Ring A is represented by
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in Compound 70.
Per Claim 30, R1 and R2 are each an aryl substituent in Compound 70 and are represented by (XXXx)
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wherein B1 and B3 are CL1 and CL3, and L1 and L3 are each CF3. B2, B4, B5 are CL2, CL4, CL5, and L2, L4, L5 are each H.
Per Claim 31, R1 and R2 are each an aryl substituent in Compound 70 and are represented by
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.
Regarding Claims 20, 32, and 33, Compound 70 does not comprise a heteroaryl substituent.
Compound 70 is represented by Cui’s Formula 1 (shown below) [0028]. X and Y are each represented by Group A1 in Compound 70 [0113]. However, Cui also teaches X and Y may be represented by Group A3 (shown below) [0113]. Cui further teaches the compounds of Formula 1 may be used in the hole injection layer and offer greatly improved voltage and lifetime in an OLED ([0013] and [0036])
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Therefore, given the general formula and teachings of Cui, 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 Group A1 with Group A3, because Cui teaches the variable may suitably be selected as A1–A7 for X and Y. The substitution would have been one preferred 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 as the p-dopant in the hole injection layer of the organic light emitting device of Senkovskyy and possess the benefits taught by Cui. See MPEP 2143.I.(B).
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 Group A3, because it would have been choosing between the exemplified groups A1–A7 for X and Y in Cui’s Formula 1, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the p-type dopant in the hole injection layer of the organic light emitting device of Senkovskyy and possessing the benefits taught by Cui. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Cui’s Formula 1 having the benefits taught by Cui in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Per Claim 20, the modified version of Compound 70 (hereinafter “Modified Compound 70”) reads on Applicant’s limitation since it comprises a C5 heteroaryl group substituted with fluorine atoms.
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Per Claim 32, X1 is represented by (XXa)
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in Modified Compound 70 wherein Z3 is N, while Z1, Z2, Z4, and Z5 are each represented by CY1, CY2, CY4, and CY5 wherein Y1, Y2, Y4, and Y5 are each F.
Per Claim 33, X1 and X2 are each represented by (X143)
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.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Zeika et al. (US 2017/0012203 A1) teaches compounds which appear to read on Applicant’s Formula (IIa).
Lederer et al. (US 2020/0032093 A1) teaches compounds which appear to 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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