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 .
Election/Restrictions
The applicant's election with traverse of Group I, claims 25-38 and 40-48 and species (i) in the reply filed on 11/10/2025 is acknowledged.
After reconsideration of the requirement of election of species set forth in the Office action dated 09/10/2025 and in an effort to further prosecution, the requirement of election of species ONLY is hereby withdrawn. However, the requirement for restriction is maintained.
The traversal is on the ground(s) that compounds having the special technical feature are not disclosed or suggested in the cited reference and the applicant argues that the proposed modification is not suggested or obvious for the reasons argued below.
(1) The applicant argues that the preferred substituent ranges for linker L1 are dependent on the core structure.
Examiner's response – This is not found persuasive because the invention of the prior art is not limited to or defined by only those embodiments disclosed in the examples, both phenylene and naphthylene at position L1 fall within the scope of the general formula, and the prior art reference does not appear to criticize, discredit, or otherwise discourage the substitution. Therefore, it would have been obvious to one having ordinary skill to make the substitution.
(2) The applicant argues that L1 is defined broadly and no examples that meet the claimed formulae are present.
Examiner's response – Not only does the reference teach specifically that examples of arylene include naphthyl (and the definition of L1 includes arylene), but also there are specific compounds that show the position corresponding to L1 and a naphthylene. Therefore, it would have been obvious to one having ordinary skill to make the substitution.
(3) The applicant argues that the data in the specification demonstrate that the claimed compound achieves unexpected results relative to the prior art compound.
Examiner's response – This is not found persuasive for at least the reason that it is not drawing comparison to the closest prior art and is not commensurate in scope. The examples pointed to the specification have a 1,4-substituted naphthylene group and the HetAr group as a triazine, while the cited prior art also have a 2,6-substitued naphthylene group and the HetAr group is a quinoxaline group or a quinazoline group. Thus, it remains unclear what differences in results would be present when the naphthylene group is substituted at other positions and the HetAr group is other than triazine.
The requirement is still deemed proper and is therefore made FINAL.
Claim 39 is withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. The applicant timely traversed the restriction (election) requirement in the reply filed on 11/10/2025.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on each of 03/04/2022, 02/08/2024, and 12/11/2024 has been considered by the examiner.
Specification
Applicant is reminded of the proper language and format for an abstract of the disclosure. A patent abstract is a concise statement of the technical disclosure of the patent and should include that which is new in the art to which the invention pertains. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details.
The abstract of the disclosure is objected to because it does not appear to describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details. It is the Examiner's position that at least a chemical structure formula (1) should be shown in the abstract. Correction is required. See MPEP § 608.01(b).
Claim Objections
Claims 25, 26, 28, 30-31, 33-35, 38, 40-42, 45, and 48 are objected to because of the following informalities:
in claim 25 it is suggested that Arʽ in the definitions of R, R2, and R3 be changed to Ar' in each instance for ease of reading and consistency;
in claim 26 it is suggested that "[t]he compound according to Claim 25, selected from the compounds of formulae (1a)… (1m)," be changed to "[t]he compound according to Claim 25, wherein the compound is selected from wherein formula (1) is represented by one of
in claim 28 it is suggested that "[t]he compound according to Claim 25, selected from the compounds of formulae (3), (4), and (5)" be changed to "[t]he compound according to Claim 25, wherein the compound is selected from wherein formula (1) is represented by one of
in claim 30 it is suggested that "[t]he compound according to Claim 25, selected from the compounds of formulae (3a-1),…(5a-2)" be changed to "[t]he compound according to Claim 25, wherein the compound is selected from wherein formula (1) is represented by one of
in claim 31 it is suggested that "[t]he compound according to Claim 25, selected from the compounds of formulae (3b), (4b), and (5b)" be changed to "[t]he compound according to Claim 25, wherein the compound is selected from wherein formula (1) is represented by one of
in claim 33, it is suggested that "wherein R3 has the definitions in Claim 25" in the definition of X2 be changed to "wherein R3 has the definition[[s]] in Claim 25" for ease of reading;
in claim 33, it is suggested that ", where R4 has the definition given in Claim 25" be added to the definition of A, for ease of reading;
in claim 34, it is suggested that ", and R4 has the definitions given in Claim 25" be changed to ", and R3 and R4 have the definitions given in Claim 25" for ease of reading;
in claim 35 it is suggested that "R4 has the definitions in Claim 25" be changed to "R4 has the definition[[s]] in Claim 25" for ease of reading; and
in claim 38, it is suggested that "where R4 has the definitions given above" be changed to "where R4 has the definition[[s]] in Claim 25" for ease of reading and consistency;
in claim 40, it is suggested that the period on line 3 be replaced with a colon or comma; and
in claims 40 and 48, it is suggested that Arʽʽ in the definition of R6 be replaced with Ar'' for ease of reading and consistency;
in claims 41-42, it is suggested "The" be added to the beginning of the claim for ease of reading; and
in claim 45, it is suggested "utilixzing" be replaced with "utilizing".
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 25-38 and 40-48 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.
Regarding claims 25, 40, and 48, the use of the phrase "especially…" in the definition of R5 and R8 renders each of the claims indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention.
For purposes of examination, the claims will be interpreted such that the limitations following the phrase "especially" are optional.
Claims 26-48 are rejection for being dependent on indefinite claim 25.
Claims 41-44 are rejection for being dependent on indefinite claim 40.
Regarding claim 27, the claim recites formula (1); however, claim 26 from which claim 27 depends requires the compound of formula (1) be selected from a compound of one of formulae (1a) to (1m). The claim is indefinite because it is unclear how or when formula (1) would be selected to be further limited.
For purposes of examination, the claim will be interpreted such that formula (1) is not included in the list in claim 27.
Regarding claim 32, the claim recites "HetAr may be substituted in each case by one or more R3 radicals." The claim is indefinite because it is unclear what is mean by "in each case" when it appears that only one HetAr is present. Does the limitation mean that there can be more than one HetAr?
For purposes of examination, the claim will be interpreted such that the limitation reads "HetAr may be substituted by one or more R3 radicals."
Claim Rejections - 35 USC § 102
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 25-27, 32-33, 37-38 and 40-48 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Zheng et al. WO-2021190380-A1, (hereinafter "Zheng-WO" and see English language machine translation referred to herein as "Zheng-MT").
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. See MPEP §§ 215 and 216.
Regarding claims 25-27, 32-33, 37-38 and 40-48, Zheng discloses an organic compound that includes the structures of a Chemical Formula 1 and Chemical Formula 2 (Zheng-MT, page 2 of 14, lines 11-12) and an organic electroluminescent device comprising an anode, an organic electroluminescent layer, and a cathode (Zheng-MT, page14 of 32 to page 15 of 32, line 2) wherein the organic electroluminescent layer comprises a host material and a guest material, and the compound is used as the host material (Zheng-MT, page 14 of 31, lines 20-21). Zheng discloses the compound used in a mixed host material (Zheng-MT, page 5 of 32, lines 30-31 and Zheng-MT, page 26 of 32, lines 5-9) and discloses examples of forming the device comprising the mixed host system wherein the other compound in the mixed host material to be
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(Zheng-MT, page 22 of 32, lines 1-25 and Zheng-WO, Tables 12-13), which is a further matrix material compound of the claimed formula (6)
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(Zheng-MT, page 26 of 32, lines 5-9 and Zheng-WO, Tables 16-17), which is a further matrix material compound of the claimed formula (7), at 50% by weight in the emission layer (Tables 12 and 16), while the dopant is at 5%, leaving the host compound with the remaining 45% by weight. Zheng discloses examples of the compound including compound 66
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(page 16) and compound 117
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(page 18), which are each a compound of the claimed formula (1). It is noted that the organic electroluminescent device is an electronic device.
For example, Zheng's compound 66 is a compound of the claimed formula (1) (1d) wherein
X is in each case CR;
two adjacent Y are a group of the formula (2) and the other two are CR;
X1 is in each case CR;
HetAr is an electron-deficient heteroaryl group have 6 aromatic ring atoms (a pyrazine group);
R is in each case H;
R1 is in each case an unsubstituted straight-chain, branched, or cyclic alkyl group and two R1 radicals form an aliphatic ring system;
R2 is not required to be present;
R3 is not required to be present;
Ar' is not required to be present;
R4 is not required to be present;
R2 is not required to be present; and
o is 0.
Therefore, device comprising Zheng's compound in the mixed host system meets claims 25-27, 32-33, 37-38 and 40-48.
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 28-31, 34-36 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Zheng et al. WO-2021190380-A1, (hereinafter "Zheng-WO" and see English language machine translation referred to herein as "Zheng-MT") as applied to claim 25 above.
Regarding claims 28-31, Zheng discloses the device comprising the compound as described above with respect to claim 25.
Zheng does specifically exemplify a compound of one of the claimed formulae (3), (4), or (5), a compound of one of the claimed formulae (3a-1) (3a-2), (4a-1), (4a-2), (5a-1), or (5a-2), and a compound of one of the claimed formulae (3b), (4b), or (5b). However, the compounds 66 and 177, shown above, are each a positional isomer of the claimed compound of one of these formulae wherein the naphthalene group is substituted at the 1- and 4-positions
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as opposed to the 1- and 5-positions, wherein the positional isomers are both encompassed by the general formula of Zheng. Zheng teaches that compound of the general formula can improve the efficiency of an organic electroluminescence device and prolong the service life thereof (Zheng-MT, page 1 of 32, lines 6-7; page 5 of 32, lines 29-33).
Given the general formula and teachings of Zheng, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of either of compound 66 or 117 wherein the naphthalene group is substituted at the 1- and 4-positions. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by the general formula of Zheng in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as a host in the emitting layer of the device of Zheng and possess the properties of improved efficiency and prolonged lifetime taught by Zheng. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP § 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP § 2144.09 II.
The modified compounds of Zheng meet the claimed formulae (5), (5a-1), (5a-2), (5b).
Regarding claims 34-36, Zheng discloses the device comprising the compound as described above with respect to claim 25.
Zheng does specifically exemplify a compound wherein the position corresponding to the claimed HetAr is a group meeting the claimed formula HetAr-9. For example, the cited compounds 66 and 117 shows a group meeting the claimed formula HetAr-2 at the position corresponding to the claimed HetAr.
However, Zheng teaches variable R4 in Zheng's general formula may be a substituted or unsubstituted alkyl, aryl, heterocyclic group, or cycloalkyl (Zheng-MT, page 2 of 32, lines 26-28) and teaches exemplary compounds wherein the position of R4 is
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, see for example compound 6 (page 14). Zheng teaches that compound of the general formula can improve the efficiency of an organic electroluminescence device and prolong the service life thereof (Zheng-MT, page 1 of 32, lines 6-7; page 5 of 32, lines 29-33).
Therefore, given the general formula and teachings of Zheng, 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 R4 group in either of compounds 66 or 117 with
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, because Zheng teaches the variable may suitably be selected as such. The substitution would have been one known 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 a host in the emitting layer of the device of Zheng and possess the properties of improved efficiency and prolonged lifetime taught by Zheng. See MPEP § 2143.I.(B).
The modified compounds of Zheng meet the claimed formula wherein the HetAr group is a group of claimed formula HetAr-9 and HetAr-1-d wherein Ar are each an aromatic ring system having 6 aromatic ring atoms.
Claims 25-33, 35, 37-38 and 40-48 are rejected under 35 U.S.C. 103 as being unpatentable over Kang et al. WO-2015099486-A1 (hereinafter "Kang").
It is noted that Kang et al. WO-2015099486-A1 is cited on the IDS of 03/04/2022.
Regarding claims 25-33, 35, 37-38, and 40-48, Kang teaches a compound represented by a formula 1 (¶ [12] to ¶ [13]) having high luminescent efficiency and excellent lifespan properties (¶ [29]) and an organic electroluminescent device comprising the compound (¶ [31]) having long driving lifetime, good current efficiency and power efficiency (¶ [29]). Kang teaches wherein the organic electroluminescent device comprises a light emitting layer between an anode and a cathode (¶ [69]-[71]), wherein the compound is a first host in the light emitting layer with a second host and a dopant (¶ [72]). Kang teaches second host compounds in paragraphs ¶ [95]-[111] that are compounds of the claimed formulae (6), (7), (8), (9), and/or (10). Kang teaches that the first host material and the second host material may be in the range of 1:99 to 99:1 in a weight ratio (¶ [73]), which overlaps with the claimed ranges. A prima facie case of obviousness exists where the claimed ranges overlap or lie inside ranges disclosed by the prior art. See MPEP § 2144.05.
Kang teaches exemplary compounds of the formula 1 including compounds H-14 and H-15
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(page 8) and compounds H-64 and H-65
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(page 9).
Kang does not exemplify a compound of the claimed formula (1). For example, the compounds H-14, H-15, H-64, and H-65 differs from the claimed compound of formula (1) wherein the position corresponding to X in Kang's formula is a nitrogen substituted with a phenyl group instead of a carbon substituted with two claimed groups R1. However, Kang teaches that the position corresponding to X in Kang's formula may be NR6 or CR7R8, among others (¶ [16]), and teaches exemplary compounds wherein X is CR7R8 wherein R7 and R8 are each methyl in several compounds including for example compound H-6 and H-7
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(page 8).
Therefore, given the general formula and teachings of Kang, 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 NR6 group at the position corresponding to X in Kang's general formula in the compounds shown above with CR7R8 wherein R7 and R8 are each methyl, because Kang teaches the variable may suitably be selected as such and teaches exemplary compounds wherein this position is CR7R8 wherein R7 and R8 are each methyl. The substitution would have been one known 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 in the device of Kang and possess the properties of high luminescent efficiency and excellent lifespan and result in a device with long driving lifetime, good current efficiency and power efficiency, as described above taught by Kang. See MPEP § 2143.I.(B).
The modified compounds of Kang are compounds of the claimed formula (1), (1c), (1h), (5), (5a-1), (5a-2), (5b) wherein:
X is in each case CR;
two adjacent Y are a group of the formula (2) and the other two are CR;
X1 is in each case CR;
HetAr is an electron-deficient heteroaryl group have 6 aromatic ring atoms (a quinoxaline group or a quinazoline group);
R is in each case H;
R1 is in each case an unsubstituted straight-chain alkyl group (a methyl group);
R2 is not required to be present;
R3 is not required to be present;
Ar' is not required to be present;
R4 is not required to be present;
R2 is not required to be present; and
o is 0.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure: Jun et al. US-20170217992-A1 (WO-2016021989-A1 equivalent), cited on the IDS of 12/11/2024, teach a compound of a formula 1 (¶ [0010]) and disclose examples including compound A-22
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(page 7).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Elizabeth M. Dahlburg whose telephone number is (571)272-6424. The examiner can normally be reached Monday through Thursday, 9 a.m. to 4 p.m. ET, and alternate Fridays.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer 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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/ELIZABETH M. DAHLBURG/Primary Examiner, Art Unit 1786