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 .
Current Status
This action is responsive to the amended claims of 03/22/2023. Claims 1-23 are pending. Claims 2-20 are withdrawn. Claims 1 and 21-23 have been examined on the merits.
Note, Examiner Bell inherited this application from the prior Examiner.
Election/Restrictions
Applicant’s election without traverse of the compound Z(1-2), below, in the reply filed on 11/28/2025 is acknowledged.
Z(1-2),
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, is a species of claim 20 and reads on claims 1 and 16-23.
A search for the compound Z(1-2) did not return any prior art (see SEARCH 6 of the attached search notes). Thus, the search was expanded to the scope of Formula Z(1) as recited in claim 16. The search for Formula Z(1) utilized the structure:
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wherein R1 is the instant A and B which may be phenyl, biphenyl, or naphthyl attached via any of the F1, F2, or F3 nodes, and wherein R2 is the instant Ar1 and Ar2 which may be phenyl or naphthyl attached via any of the F1 or F3 nodes. This search did not retrieve any prior art for independent claim 16 (see SEARCH 6 of the attached search notes).
Thus, the search was further expanded to the Formula (1) of claim 1 wherein C is Z. This search retrieved prior art commonly owned by the Applicant (TOSOH), the expanded species is:
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wherein A is biphenyl, B is biphenyl, n is 1, L is phenyl, and C is Z wherein Ar1 is phenyl and Ar2 is biphenyl.
Since the search retrieved a commonly owned reference, the search was further extended to the following species:
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wherein A is phenyl, B is biphenyl, n is 0 meaning L is not present, and C is Z wherein Ar1 and Ar2 are both naphthyl.
The expanded species read on claims 1 and 21-23.
Claims 2-20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 11/28/2025.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
The effective filing date is 10/01/2021.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 06/22/2023 and 03/27/2025 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Claim Objections
Claims 1 and 21-23 are objected to because of the following informalities. Appropriate correction is required.
Claim 1 recites “[Chem. 1]” and “[Chem. 2]” before each set of chemical structures shown in the claim. While these are each understood as labels for the chemical structures, please strike both “[Chem. 1]” and “[Chem. 2]” since they are unnecessary and do not match the claim text; e.g., “[Chem. 1]” does not match “formula (1)” as recited in the claim text. Dependent claims 21-23 are similarly rejected since they do not rectify the underlying issue.
Claim 1 recites structures for X, Y, and Z; however, this recitation lacks proper punctuation. Please add a comma between the structures and the word “and” before the final structure, as such: “
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,
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, and
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”. Dependent claims 21-23 are similarly rejected since they do not rectify the underlying issue.
Note: withdrawn claims 2-20 have similar issues as recited for claim 1, above. Examiner asks that, to expedite prosecution, Applicant kindly address the following issues in the withdrawn claims:
1) Withdrawn claims 2, 10, 13, 16, and 20 each recite at least one instance of “[Chem. ##]” (i.e., [Chem. 3] – [Chem. 12]). As described for claim 1 above, please strike each instance.
2) Withdrawn claim 2 requires punctuation and the word “and” between the structures recited for A and B, as described for claim 1 above. Further, please add a semicolon “;” after the structure X(A-9) and after the structure X(B-15) to denote the transition to the next variable.
3) Withdrawn claim 10, please amend the final three lines as such:
“selected from formulas Y(2-1) to Y(2-5)[[.]]:
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,
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,
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,
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, and
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.”
Please add commas between structures, add “and” before the final structure, move the period to the end of the claim, and place a colon after “formulas Y(2-1) to Y(2-5)”.
4) Withdrawn claim 13, please amend similar to how claim 10 is amended above. Please replace the period after “formulas Y(B-1) to Y(B-28)” with a colon, please add commas between all structures, please add “and” before the structures Y(A-10) and Y(B-28), please add “; and” after structure Y(A-10), and please add a period to the end of the claim after structure Y(B-28).
5) Withdrawn claim 16 recites “substituent(s)” four times. Please strike the parentheses around the “s” so the claim reads “substituents”. The parentheses are unnecessary since the claim recites “one or more” before “substituent(s)”.
6) Withdrawn claim 20, please amend similar to how claim 10 is amended above. Please add commas between structures, add “or” before the final structure, move the period to the end of the claim, and place a colon at the end of line 2 after “or Z(1-16)”.
Claim Interpretation
The claims in this application are given their broadest reasonable interpretation (BRI) using the plain meaning of the claim language in light of the specification as it would be understood by one of ordinary skill in the art.
Claim 1 recites “A and B each independently represent an aryl group having 6 to 20 atoms”. Under the BRI, “aryl group” is understood to include any geometric arrangement (e.g., monocyclic ring, bicyclic fused ring system, bicyclic non-fused ring system such as biphenyl, etc.) of aromatic rings so long as the total number of carbons falls within 6-20. Further, since the instant specification does not define the term “aryl group”, aryl is understood as exclusively carbon containing (i.e., no heteroatoms are included). Note: If Applicant did not intend this meaning, Applicant may consider further defining aryl group in the claim.
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 and 21-23 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.
Claim 1 recites the moieties X, Y, and Z as:
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. It is unclear whether the annotated line is intended to represent the point of attachment of X/Y/Z to the core structure of Formula (1) or if the annotated line is a methyl group. Thus, the metes and bounds of the claim are undefined rendering the claim indefinite. Dependent claims 21-23 are similarly rejected since they do not rectify the underlying issue.
Note: based on the full disclosure, and for purposes of examination, the annotated line is understood as the bond to the core structure. If this understanding is correct, please use the standard practice of denoting points of attachment with a wavy line, i.e.,
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.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1 and 21-23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by MORINAKA (JP 2020132556, pub. 08/31/2020). A translation of MORINAKA was provided in the IDS of 06/22/2023. This translation is cited below.
Regarding claim 1, MORINAKA teaches a compound of Formula 1:
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(Pg. 12 compound 46, reproduced here for clarity) wherein A is biphenyl, B is biphenyl, n is 1, L is phenyl, and C is Z wherein Ar1 is phenyl and Ar2 is biphenyl. Under the BRI discussed in ¶16, above, biphenyl falls within the instant A and B definitions. Further, the phenyl Ar1 and biphenyl Ar2 are understood as “an aromatic hydrocarbon group[s]”. Thus, MORINAKA teaches a compound of instant claim 1.
Regarding claims 21-23, MORINAKA teaches the cyclic azine compounds of the invention, represented by Formula 1, are material for an organic electroluminescent element and an electron transport material for an organic electroluminescent element (Pg. 21 ¶5-6).
In the instant claims, the preambles recite intended uses of the instant compounds exemplified by the use of the word “for”. Instant claims 21-23 only require the light emitting diode to comprise the instant compound, no other structural limitations are given. Thus, since MORINAKA teaches the above compound and said compound is taught for use in an electron transport material for an organic electroluminescent element (i.e., organic light emitting diode), the structural and intended use limitations of the instant claims 21-23 are taught by MORINAKA.
Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216.
Claims 1 and 21-23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by MORINAKA (JP 2020132556, pub. 08/31/2020). A translation of MORINAKA was provided in the IDS of 06/22/2023. This translation is cited below.
Note: the rejection over the following species is made in an effort to promote compact prosecution of the case since these species were found incidental to the search for the expanded species. This does not indicate that the full scope of the claims has been searched.
Regarding claim 1, MORINAKA teaches at least 5 further species of instant claim 1: compound 52 (Pg. 12), compound 55 (Pg. 13), compound 13 (Pg. 15), compound 14 (Pg. 15), and compound 15 (Pg. 15). Compounds 52 and 55 have the same groups as compound 46, above, but differ in the attachment point on the Ar2 biphenyl. Compounds 13-15 recite wherein A and B are phenyl and biphenyl (the assignment is interchangeable), n is 1, L is phenyl, and C is Z wherein Ar1 and Ar2 are both biphenyls. Compounds 13-15 only differ in the attachment points on the Ar1 and Ar2 moieties.
Regarding claims 21-23, MORINAKA teaches the cyclic azine compounds of the invention, represented by Formula 1, are material for an organic electroluminescent element and an electron transport material for an organic electroluminescent element (Pg. 21 ¶5-6).
Thus, since MORINAKA teaches the above compounds and said compounds are taught for use in an electron transport material for an organic electroluminescent element (i.e., organic light emitting diode), the structural and intended use limitations of the instant claims 21-23 are taught by MORINAKA.
Claims 1 and 21-23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by HAN (JP 2019-512499, pub. 05/16/2019). A translation of HAN was provided in the IDS of 06/22/2023. This translation is cited below.
Regarding claim 1, HAN teaches a compound of Formula 1:
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(Pg. 8 row 3 column 1, claim 8) wherein A is phenyl, B is biphenyl, n is 0 meaning L is not present, and C is Z wherein Ar1 and Ar2 are both naphthyl. Under the BRI discussed in ¶16, above, phenyl and biphenyl fall within the instant A and B definitions. Further, the naphthyl Ar1 and Ar2 are understood as “an aromatic hydrocarbon group”. Thus, HAN teaches a compound of instant claim 1. Note, the assignment of A and B may also be switched and still read on the instant claim.
Regarding claims 21-23, HAN teaches “described herein are compounds and organic light emitting devices comprising the same” (Pg. 22 ¶4). HAN teaches an organic light emitting device including an electrode, an electrode disposed opposite the first electrode, and a layer of 1 or more organic material layers disposed between the electrodes wherein at least one of the organic layers includes a compound of Formula 1 (Pg. 23 ¶6). HAN further teaches the compound described is used as electron transport material (Pg. 23-24 ¶7).
In the instant claims, the preambles recite intended uses of the instant compounds exemplified by the use of the word “for”. Instant claims 21-23 only require the light emitting diode to comprise the instant compound, no other structural limitations are given. Thus, since HAN teaches the above compound and said compound is taught for use in an electron transport material for a light emitting device (i.e., organic light emitting diode), the structural and intended use limitations of the instant claims 21-23 are taught by HAN.
Claims 1 and 21-23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by HAN (JP 2019-512499, pub. 05/16/2019). A translation of HAN was provided in the IDS of 06/22/2023. This translation is cited below.
Note: the rejection over the following species is made in an effort to promote compact prosecution of the case since these species were found incidental to the search for the expanded species. This does not indicate that the full scope of the claims has been searched.
Regarding claim 1, HAN teaches many further species of Formula 1 which read on the instant claim 1 wherein n is 0, A and B are an aryl group of 6-20 carbons, and C is Z wherein Ar1 and Ar2 are both aromatic hydrocarbon groups: see Pg. 8 rows 3-4 columns 1-4, Pg. 9 rows 3-4 columns 1 & 4-5, Pg. 10 rows 3-4 columns 1-4, Pg. 11 rows 3-4 columns 1 & 4-5, Pg. 12 rows 3-4 columns 1-4, Pg. 13 rows 3-4 columns 1 & 4-5, Pg. 18 row 5 columns 1-4, Pg. 18 row 6 columns 1 & 4, and Pg. 20 row 4 column 1.
HAN also teaches many species wherein n is 0, A and B are an aryl group of 6-20 carbons, and C is X wherein Ar1 and Ar2 are both aromatic hydrocarbon groups: see Pg. 8 rows 5-6 columns 1-4, Pg. 9 rows 5-6 columns 1 & 4-5, Pg. 10 rows 5-6 columns 1-4, Pg. 11 rows 5-6 columns 1 & 4-5, Pg. 12 rows 5-6 columns 1-4, Pg. 13 rows 5-6 columns 1 & 4-5, Pg. 18 row 6 column 5, and Pg. 20 row 4 column 2.
For both sets of species wherein C is Z and wherein C is X: the A and B aryl groups and the Ar1 and Ar2 aromatic hydrocarbon groups are independently phenyl, biphenyl, naphthyl, phenanthracene, fluorene, and dihydropyrene (i.e., aromatic cyclic groups of 6-20 carbons).
Regarding claims 21-23, HAN teaches “described herein are compounds and organic light emitting devices comprising the same” (Pg. 22 ¶4). HAN teaches an organic light emitting device including an electrode, an electrode disposed opposite the first electrode, and a layer of 1 or more organic material layers disposed between the electrodes wherein at least one of the organic layers includes a compound of Formula 1 (Pg. 23 ¶6). HAN further teaches the compounds described are used as electron transport material (Pg. 23-24 ¶7).
Thus, since HAN teaches the above compounds and said compounds are taught for use in an electron transport material for a light emitting device (i.e., organic light emitting diode), the structural and intended use limitations of the instant claims 21-23 are taught by HAN.
Conclusion
Claim 1 and 21-23 are rejected.
Note: a search for the Formula Z(1) of independent claim 16 did not retrieve any prior art. The closest art is MORINAKA, applied to claim 1 above. The species of MORINAKA differ from instant claim 16 in that Ar2 cannot be biphenyl (only phenyl or naphthyl). MORINAKA does not teach any compounds wherein the corresponding Ar2 is phenyl or naphthyl and does not suggest adjusting the bonding from non-fused ring systems to fused ring systems (such as naphthyl). Further MORINAKA differs from the prior art HAN, above, in that the phenyl L is present in MORINAKA but is not in HAN. Thus, there is no teaching-suggestion-motivation to make the necessary change (e.g., subtracting an entire phenyl from Ar2) to arrive at the compound of Formula Z(1).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SARA ELIZABETH BELL whose telephone number is (703)756-5372. The examiner can normally be reached Monday-Friday 9:00-5:30.
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/S.E.B./Examiner, Art Unit 1625
/JOHN S KENYON/Primary Patent Examiner, Art Unit 1625