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 .
Priority
Acknowledgment is made of applicant’s claim for foreign priority based on
applications filed in KR on November 29, 2022. It is noted, however, that the
foreign priority date is the effective filing date of the claimed invention if
a. The foreign application supports the claimed invention under 112(a), and
b. The applicant has perfected the right of priority by providing
i. A certified copy of the priority application, and
ii. A translation of the priority application (if not in English).
In the instant case, the applicant has submitted a certified copy of the priority application, but it is not in English, and the examiner cannot determine if it
supports the claimed invention. The effective filing date of the application is considered to be November 20, 2023, which is the actual filing date of instant application 18/514,459.
Specification
The abstract of the disclosure is objected to because the abstract is 38 paragraphs and 483 words when the abstract should be at most 1 paragraph and 150 words. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
The disclosure is objected to because of the following informalities: the figure for Preparation Example 2: Preparation of Target Compounds contains small and low resolution structures and text that is difficult to discern, reproduced below.
Appropriate correction is required.
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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 1-18 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 a heterocyclic compound of claim wherein Chemical Formula 1 contains the optional fused ring substituent wherein a is an integer of 0 or 1. It is unclear what the identity of R5 is because (1) the identity of R5 is linked to the identity of R6 and (2) R6 is an optional substituent on the optional fused ring substituent defined by a as an integer of 0 or 1. Therefore, the confusion arises wherein a is 0 and:
R5 must be represented by the Chemical Formula 2-1 or 2-2 OR
R5 is not represented by Chemical Formula 2-1 or 2-2 and instead R6 is represented by the above Chemical Formulas.
For the purposes of examination, the examiner will interpret claim 1 as both (A) and (B).
Claims 2-18 are also rejected as they depend from claim 1 and do not cure the deficiencies of the claim from which they depend.
Note that in claim 3, Chemical Formula 1-a-1 and 1-b-1 contains variables R1 to R6, L1, Ar1, Ar2, n1, m1 and m2 having the same definitions as in Chemical Formula 1. Chemical Formula 1-b-1 recites (1) that L1 is attached to a diaryl amino group and (2) that at least one of R5 and R6 is the amino group represented by Chemical Formula 2-1 or Chemical Formula 2-2 wherein m1 is an integer of 1 or 2 and m2 is an integer of 1 to 4. Therefore, Chemical Formula 1-b-1 is interpreted to necessitate at least two diarylamino groups attached to the core heterocyclic compound, shown below: one diarylamino group attached at L1 and a second at either R5 or R6.
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Claim 3 also recites Chemical Formula 1-a-1 wherein L1 is attached to a diarylamino group and R5; however, it is unclear whether R5 is a diarylamino group for the reasons stated above. Chemical Formula 1 in instant claim 1 defines at least one of R5 and R6 is represented by the Chemical Formula 2-1 or 2-2 and m1 and m2 are each independently one of integers of 1 to 4; however, R5 is not required to be either Chemical Formula 2-1 or 2-2 when a is 0. Therefore, the examiner will interpret Chemical Formula 1-a-1 with the interpretations established above wherein (A) R5 must be diarylamine group and (B) R5 is not diarylamine group.
Regarding claim 4, Chemical Formula 1-a-2 suffers from the same ambiguity.
Regarding claim 5, Chemical Formula 1-a-1-1, Chemical Formula 1-a-1-2, Chemical Formula 1-a-2-1, and Chemical Formula 1-a-2-2 suffer from the same ambiguity.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 9 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 9 claims specific exemplary compounds. Some of the compounds including at least 253, 273, 393, and 513 are not encompassed by Chemical Formula 1 of instant claim 1. For example, Compound 253 is not encompassed by Formula 1 of claim 1.
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In Compound 253, L1 is a substituted C6 arylene group (i.e. phenylene); n1 is 1; and Ar2 is a substituted C2 to C60 heteroaryl group (i.e. N-phenyl carbazole). Although the instant specification recites “substituted or unsubstituted means being substituted with one or more substituents selected from the group consisting of deuterium, halogen, …, or being substituted with a substituent in which two or more substituents selected from among the substituents exemplified above are linked or being unsubstituted” (page 7, last paragraph; and emphasis added), a single bond between L1 and Ar2 pointed by an arrow in the figure above appears to not be formed by any exemplified substituent groups in the specification. That is, no two substituents exemplified in the last paragraph of page 7 of the specification can be linked to form a single bond. Therefore, the substituted arylene at position L1 and the substituted heteroaryl group at position Ar2 cannot be linked by a single bond based on the limitation of claim 1 in light of the specification. Currently claim 9 is dependent from claim 1. Therefore, claim 9 fails to include all the limitations of the claims upon which they depend.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claims 1-3 and 8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Cao et al. (CN 110041159 A, hereinafter "Cao"). Note that a machine-generated English translation is relied upon and provided with this office action.
In the pertinent art of organic light-emitting devices, Cao discloses an organic light-emitting device and a novel fused heterocyclic chemical compound including the specific compound P252 (abstract; Description pg 23; claim 4).
Instant Chemical Formula 1 & 2-1
P252 of Cao
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The compound P252 is a compound of instant Chemical Formula 1 in instant claim 1 wherein:
A is 0;
R1 to R4 are H;
R5 is represented by Chemical Formula 2-1;
m1 is 1;
L1 is a substituted C3 heteroarylene group “triazine”;
n1 is 1;
Ar1 and Ar2 are C12 aryl “biphenyl”;
Represented by Chemical Formula 1-a in claim 2;
Represented by Chemical Formula 1-a-1 in claim 3 wherein;
R5 is H; m1 is 2; R6 is Chemical Formula 2-1; m2 is 1; and a is 0;
Therefore, Compound P252 of Cao anticipates instant claims 1-3.
Regarding claim 8, the Compound P252 does not include deuterium as a substituent.
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.
Claims 4-7 and 9-13 are rejected under 35 U.S.C. 103 as being unpatentable over Cao et al. (CN 110041159 A, hereinafter "Cao") as applied to claims 1-3 as described above.
Cao teaches the compound P252 which is a compound of instant Chemical Formula 1 that reads on instant claims 1-3 as described above. Cao teaches that the compound P252 is a compound of Cao’s Formula VII, which is also a compound of Cao’s Formula 1 wherein A4 and A1 is nitrogen, forming a fused pyrazine ring (Description pg 3-4).
Formula 1 of Cao
Formula VII of Cao
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Cao teaches the specific compound P104 which is a compound of the Formula 1 of Cao wherein A1 is nitrogen, R5 is a substituted carbazole with another carbazole (Description pg 15, col II, row VI). Cao teaches the specific compound P170 which is a compound of the Formula 1 of Cao wherein A4 is nitrogen, R5 is a substituted carbazole with another carbazole. Cao does not particularly limit the Formula 1 to being nitrogen at A1 or nitrogen at A4 positions: Cao teaches that both A1 and A4 positions can be nitrogen as seen from the Formula VII and the compound P252 as described above.
P104 of Cao
P170 of Cao
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Cao teaches that the organic electroluminescent element prepared by utilizing the chemical compound of chemical Formula 1 can reduce starting voltage, improve luminous efficiency, and improve luminance (Abstract).
Cao teaches the above; however, Cao fails to teach a specific compound of Formula 1 with the substitution pattern of compounds P104 and P170 wherein both A1 and A4 are nitrogen. 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 further include Ar4 as nitrogen in the compound P104 of based on the teachings of Cao. The motivation for doing so would have been to obtain a device with reduced starting voltage, improved luminous efficiency, and improved luminance, as taught by Cao (abstract).
The Modified Compound P104 of Cao is shown below and reads on chemical formula 1-a-2 of claim 4 wherein:
R1 to R4 are H;
n1 is 0;
R7 is C12 heteroaryl group “carbazole” and r is 1;
R5 is H and m1 is 2;
R6 is Chemical Formula 2-1, m2 is 1, and a is 0.
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Regarding claim 7, the Modified Compound P104 is a compound of Chemical Formula 2-2-a wherein b1 and b2 are 0; R7a is C12 heteroaryl group “carbazole” and r1 is 1.
Regarding claim 5, Cao teaches the Modified Compound P104 that reads on claim 4 as described above; however, Cao is silent on the Modified Compound P104 where the carbazole displays a connectivity to the core heterocycle of instant Chemical Formula 1-a-2-2.
Cao teaches that the R5 is carbazole and that R5 is not necessarily limited to a singular position, but rather defined as any position in the terminal ring of the core heterocycle as seen in Formula 1 and Formula VII described above.
Therefore, given the general formula and teachings of Cao, 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 R5 of substituted carbazole at a different position of the terminal ring, because Cao teaches the variable may preferably be selected as substituted carbazole. 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 compound in the organic layer of the light-emitting device of Cao and possess the benefits of reduced starting voltage, improved luminous efficiency, and improved luminance, as taught by Cao (abstract). See MPEP 2143.I.(B).
The resulting Modified Compound 2 P104 of Cao is shown below and reads on the Chemical Formula 1-a-2-2 of instant claim 5.
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Regarding claims 6 and 9, Cao teaches the Modified Compound 2 P104 of Cao that is a compound of Claim 1 where position corresponding to instant R1 and R2 are H; however, Cao is silent on a compound wherein R1 and R2 are each independently a substituted or unsubstituted C6 to C60 aryl group. Cao does not necessarily limit the identity of the positions corresponding to R1 and R2 as only H as seen in the Modified Compound 2 P104 described above. Cao defines R1 in the Formula 1 and Formula VII of Cao as selected from C6 to C60 aryl groups (Description pg 8). Cao teaches the specific compound P98 that contains a fused pyrazine wherein the positions not participating in ring fusion are preferably substituted with substituted C6 aryl groups “phenylene” (Description pg 15).
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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 further include the substitution of the pyrazine with C6 aryl groups “phenylene” in the Modified Compound of 2 P104 of Cao in the light-emitting device of Cao, based on the teachings of Cao. The motivation for doing so would have been to obtain a device with reduced starting voltage, improved luminous efficiency, and improved luminance, as taught by Cao (abstract).
The resulting Modified Compound 3 P104 is shown below and reads on claim 6 and is the same as compound 396 in claim 9.
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Regarding claim 10, Cao teaches the Device P01 which is a light emitting device that contains a compound of Cao’s Formula 1 P01 with compound B as the light base material and light doping materials in the light emitting layer (Description pg 31-32). The Device P01 has the following structure: ITO electrode/hole injection layer/hole transport layer/light emitting layer with P01 and Compound B/electron transport layer/LiF/Al electrode (Description pg 32-33). Cao teaches the above; however, Cao does not teach a specific device containing the compound P252, described above, as the compound of Cao’s Formula 1 in the light-emitting layer.
Cao teaches an anode, multiple organic layers, and a cathode and the compound P01 is in the organic layer as discussed above. It would have been obvious to use the compound P252 in the light-emitting layer with the device structure of anode, multiple organic layers, and cathode as Cao demonstrates this device structure was known prior to the effective filing date of the claimed invention.
The resulting Modified Device P01 with the compound P252 reads on claims 10-11.
Regarding claim 12, the heterocyclic compound P252 used in the light emitting layer, in the Modified Device P01, reads on the light emitting layer including a host material wherein the host material includes the heterocyclic compound of instant claim 12.
Regarding claim 13, the Modified Device P01 comprises a light emitting layer, hole injection layer, hole transport layer, and electron transport layer.
Claims 14-18 are rejected under 35 U.S.C. 103 as being unpatentable over Cao et al. (CN 110041159 A, hereinafter "Cao") applied to claims 1-13 as described above in view of Xing et al. (CN 111303134 A, hereinafter “Xing”). Note that a machine-generated English translation is relied upon and provided with this office action.
Cao teaches the compounds P252, Modified Compound 3 P104 of Cao, and the Modified Device P01 of Cao that reads on claims 1-13 as described above. However, Cao fails to teach an organic material layer further including a heterocyclic compound of instant Chemical Formula A in instant claim 14.
In the relevant art of organic light-emitting devices, Xing teaches a novel organic light-emitting material used in the organic layer, including the light-emitting layer, that follows the General Formula 1 and the specific compound A17 which features a triazine core attached to a modified dibenzofuran (Abstract, Description pg 4-6).
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General Formula 1
A17
The compound A17 of Xing is a compound of instant Chemical Formula A of instant claim 14 wherein:
X1 to X3 are N;
R11 is unsubstituted C6 aryl “phenylene”;
R12 is unsubstituted C10 aryl “naphthyl”;
R13 is Chemical Formula B-1;
X11 is O;
C is 1;
R16 to R18 are H;
a1 is 3, a2 is 2, and a3 is 4;
represented by Chemical Formula A-1 of claim 15.
Xing teaches the compound of General Formula 1 of Xing is used in the light-emitting layer as the main material in conjunction with a dye material (Description pg 19) such as in Example 1 (Table 1) and the resulting device displays reduced driving voltage, improved current efficiency, and extended device lifespan (Description pg 20).
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 further include the compound A17 of Xing, to replace Compound B in the light-emitting layer in the Modified Device P01 of Cao, based on the teachings of Xing. The motivation for doing so would have been to obtain a device with reduced driving voltage, improved current efficiency, and extended device lifespan, as taught by Xing (Description pg 20).
The resulting Modified Device 2 P01 of Cao and Xing has the following structure ITO electrode/hole injection layer/hole transport layer/light emitting layer with Compound P252 of Cao and Compound A17 of Xing/electron transport layer/LiF/Al electrode. The Modified Device 2 P01 of Cao and Xing reads on instant claims 14-15 and 17.
Regarding claim 18, Cao teaches that the light emitting layer contains two compounds A and B wherein compound A can be 5% and compound B can be 5%. Therefore, Compound A can span the range of 5% to 95%. Therefore, the Modified Device 2 P01 contains compound P252 that can span the range of 5% to 95%, which reads on the weight ratio of 1:10 to 10:1 in instant claim 18.
Regarding claim 16, the Modified Device 2 P01 contains the compound A17 of Xing; however, it is silent to the containing a compound selected from the group in instant claim 16. Compound A17 of Xing teaches a compound of General Formula 1 wherein Ar2 is a fluorenyl group; however, Xing does not necessarily limit A2 to only fluorenyl. Xing teaches compound A19 wherein the dibenzofuran core is substituted by a napthyl group in place of fluorene (Description pg 6).
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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 fluorenyl group with a napthyl group in the Compound A17 of Xing in the Modified Device 2 P01 of Cao and Xing, based on the teachings of Xing. The motivation for doing so would have been to obtain a device with reduced driving voltage, improved current efficiency, and extended device lifespan, as taught by Xing (Description pg 20).
The resulting Modified Device 3 P01 of Cao and Xing containing the Modified Compound A17 of Xing is shown below and reads on instant compound 1-10 of instant claim 16.
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Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LUCAS Q NGUYEN whose telephone number is (571)272-1199. The examiner can normally be reached Monday - Thursday 7:30 am - 5:00 pm Fridays 7:45 am to 12:00 pm.
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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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/L.Q.N./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
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