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 .
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 02/17/2025 and 07/28/2025 were filed after the mailing date of the instant application on 11/09/2020. The submissions are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Response to Amendment
In the response filed 07/16/2025, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(b) of claim 8 as failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention is withdrawn by the Office.
Claims 1, 3-4, 8, 13-16, and 18 have been amended.
Claims 9 and 10 have been canceled.
Claims 1-8 and 11-20 are pending in the application.
Response to Arguments
Applicant's arguments with respect to the rejections over Choi et al. (WO 2015/009102 A1) in view of Fukuda et al. (JP 2004/311413 A1) have been fully considered but they are not persuasive. Applicant’s amendments do not overcome the prior art because the prior art still reads on the claimed invention.
A reinterpretation of the prior art is given below to explain how the prior art still reads on the claimed invention.
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 and 17 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.
With respect to claim 16, it contain the limitation that R11, R13, R14, R21, R23, and R24 in Formula 1-1 are each independently selected from a Markush group that comprises one option of an electron-donating group comprising an amine, which is a scope that has been eliminated from parent claim 8.
In continuing examination, this will be interpreted as a Markush group comprising a C1-C60 heteroaryl group, as set forth in parent claim 8.
With respect to claim 17, it contain the limitation that R11, R13, R14, R21, R23, and R24 in Formula 1-1 are each independently selected from a Markush group that comprises one option of an electron-donating group comprising an amine, which is a scope that has been eliminated from parent claim 8.
In continuing examination, this limitation will be interpreted as “The heterocyclic compound of claim 16, wherein the C1-C60 heteroaryl group is selected from groups represented by Formulae 6-2 and 6-3--”
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.
Claims 16 and 17 are 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.
With respect to claims 16 and 17, they contain the limitation that R11, R13, R14, R21, R23, and R24 in Formula 1-1 are each independently selected from a Markush group comprising one option of an electron-donating group comprising an amine, which is a scope that has been eliminated from parent claim 8.
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 § 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 1-8 and 11-20 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al. (WO 2015/009102 A1, using the attached translation for references) in view of Fukuda et al. (JP 2004/311413 A, using the previously provided translation for references).
With respect to claim 1, Choi discloses an organic light-emitting device comprising a first electrode (an anode), a second electrode (a cathode), an organic layer between the electrodes (paragraph 63) comprising an emitting layer (paragraph 64). The first electrode is ITO (paragraph 71), the second electrode is aluminum (paragraph 72), and the organic layer (hole transport layer) comprises a compound of chemical formula 1 (paragraph 64), such as compound 48, which is pictured below (paragraph 52).
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This compound is derived from Choi chemical formula (3), which is pictured below.
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Choi also teaches R3 and R4 are hydrogen atoms and that R2 can be a substituted C6 aryl group (paragraph 40) and examples of substituents include an alkyl and aryl group (paragraph 42, lines 8-10).
However, such a compound differs from the instant claims that require that R12 and R22 are selected from hydrogen and deuterium.
Given the general formula and teachings Choi, 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 3-positional isomer of compound 48 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as hole transport materials in the organic layer of the electroluminescent device of Choi and possess the properties taught by Choi. 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.
Such a modification produces a compound which meets the requirements of instant Formula 1 when R23 is a C12 heteroaryl (9-carbazole), R13 is a C6 aryl (phenyl) group (Formula 5-1 when Z31 is a hydrogen atom and e5 is 5), L1 is a C6 carbocyclic (phenylene) group, n1 is 1 and B1 is represented by Formula 2.
In Formula 2, R101 and R102 are a C1 alkyl (methyl) group, and Ar1 is an unsubstituted C6 carbocyclic (phenyl) group. All remaining R groups are hydrogen atoms.
However, Choi does not fairly teach nor suggest such a substituent on the phenyl group at instant L1.
Fukuda teaches an analogous hole-transporting carbazole compound for use in the organic layer of an organic electroluminescent device.
Fukuda teaches that a position analogous to instant B1 (which is analogous to the substituent on R2 of Choi) should comprise a substituted alkyl group (paragraph 0022) (see also compounds 1-1 to 1-20 on pages 19-23 of the untranslated document).
Fukuda teaches that compounds having this specific structure are effective at solving the problem of “burn-in” (see the description of “burn-in” in paragraph 0016), and compounds of this structure simplify the manufacturing process by eliminating the need to do an aging treatment on the fabricated element at the initial stage of use (paragraph 0017-0019).
Fukuda exemplifies a phenyl-substituted isopropyl alkyl group as a preferred structure capable of avoiding “burn-in” in compounds such as 1-1, 1-2, 1-3, 1-8, 1-9, 1-14, 1-16, and 1-18.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to choose a phenyl-substituted isopropyl group as a substituent on the substituted phenyl at R2 in the carbazole compound of Choi in order to simplify the manufacturing process by eliminating the need to do an aging treatment on the fabricated element at the initial stage of use, as taught by Fukuda.
With respect to claim 2, Choi and Fukuda teach the organic light-emitting device of claim 1, and Choi teaches the first electrode is an anode, the second electrode is a cathode, as discussed above, and the organic layer further comprises a hole transport layer between the first electrode and the emission layer, as discussed above, and an electron transport layer between the emission layer and the second electrode (paragraph 64).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the claimed device structure, as taught by Choi.
With respect to claim 3, Choi and Fukuda teach the organic light-emitting device of claim 1, and Choi also teaches the compound may be in the emitting layer of the device (paragraph 64, lines 3-4).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound of Choi in the emission layer, as taught by Choi.
With respect to claim 4, Choi and Fukuda teach the organic light-emitting device of claim 3, and Choi also teaches that the carbazole compound may be a host for phosphorescent materials (paragraph 65).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the carbazole compound as a host material and in combination with a phosphorescent dopant material in the emitting layer of the device as taught by Choi.
With respect to claims 5 and 6, Choi and Fukuda teach the organic light-emitting device of claim 4, and Choi teaches the phosphorescent dopant may be the dopant FIrpic (paragraph 176), which is pictured below to facilitate discussion.
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This compound meets the requirements of instant Formula 401 when M is iridium, xc1 is 2 and xc2 is 1, L401 is represented by Formula 402. In Formula 402, A401 is a C6 carbocyclic (benzene) group, A402 is a C5 heterocyclic (pyridine) group, X401, X403, and X404 are a carbon atom, and X402 is a nitrogen atom, X405 is a single bond, X406 is a single bond, xc11 is 0 and xc12 is 2 and R402 is a fluorine atom. L402 is an organic ligand.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use FIrpic as a phosphorescent dopant in the emission layer of Choi in view of Fukuda, as taught by Choi.
With respect to claim 7, Choi and Fukuda teach the device of claim 3, and Choi also teaches that the device emits blue light (paragraph 172).
With respect to claim 8, Choi teaches compound 48, which is pictured below (paragraph 52).
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This compound is derived from Choi chemical formula (3), which is pictured below.
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Choi also teaches R3 and R4 are hydrogen atoms and that R2 can be a substituted C6 aryl group (paragraph 40) and examples of substituents include an alkyl and aryl group (paragraph 42, lines 8-10).
However, such a compound differs from the instant claims that require that R12 and R22 are selected from hydrogen and deuterium.
Given the general formula and teachings Choi, 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 3-positional isomer of compound 48 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as hole transport materials in the organic layer of the electroluminescent device of Choi and possess the properties taught by Choi. 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.
Such a modification produces a compound which meets the requirements of instant Formula 1 when R23 is a C12 heteroaryl (9-carbazole), R13 is a C6 aryl (phenyl) group (Formula 5-1 when Z31 is a hydrogen atom and e5 is 5), L1 is a C6 carbocyclic (phenylene) group, n1 is 1 and B1 is represented by Formula 2.
In Formula 2, R101 and R102 are a C1 alkyl (methyl) group, and Ar1 is an unsubstituted C6 carbocyclic (phenyl) group. All remaining R groups are hydrogen atoms.
However, Choi does not fairly teach nor suggest such a substituent on the phenyl group at instant L1.
Fukuda teaches an analogous hole-transporting carbazole compound for use in the organic layer of an organic electroluminescent device.
Fukuda teaches that a position analogous to instant B1 (which is analogous to the substituent on R2 of Choi) should comprise a substituted alkyl group (paragraph 0022) (see also compounds 1-1 to 1-20 on pages 19-23 of the untranslated document).
Fukuda teaches that compounds having this specific structure are effective at solving the problem of “burn-in” (see the description of “burn-in” in paragraph 0016), and compounds of this structure simplify the manufacturing process by eliminating the need to do an aging treatment on the fabricated element at the initial stage of use (paragraph 0017-0019).
Fukuda exemplifies a phenyl-substituted isopropyl alkyl group as a preferred structure capable of avoiding “burn-in” in compounds such as 1-1, 1-2, 1-3, 1-8, 1-9, 1-14, 1-16, and 1-18.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to choose a phenyl-substituted isopropyl group as a substituent on the substituted phenyl at R2 in the carbazole compound of Choi in order to simplify the manufacturing process by eliminating the need to do an aging treatment on the fabricated element at the initial stage of use, as taught by Fukuda.
With respect to claim 11, Choi and Fukuda teach the heterocyclic compound of claim 8, and L1 is a benzene group, as discussed above.
With respect to claim 12, Choi and Fukuda teach the heterocyclic compound of claim 8 and Ar1 in Formula 2 is a phenyl group, as discussed above.
With respect to claim 13, Choi and Fukuda teach the heterocyclic compound of claim 8, and B1 in Formula 1 is represented by Formula 2-1, as pictured above.
With respect to claim 14, Choi and Fukuda teach the heterocyclic compound of claim 8, and *-(L1)-(B1)n1 is represented by Formula A-2, as pictured above.
With respect to claim 15, Choi and Fukuda teach the heterocyclic compound of claim 8, and *-(L1)-(B1)n1 is represented by Formula A-12, as pictured above.
With respect to claim 16, Choi and Fukuda teach the heterocyclic compound of claim 8, and R23 is a C12 heteroaryl (9-carbazole), R13 is a phenyl group (Formula 5-1 when Z31 is a hydrogen atom and e5 is 5), and the remaining R groups are each hydrogen atoms, as discussed above.
With respect to claim 17, Choi and Fukuda teach the heterocyclic compound of claim 16, and the heteroaryl group is represented by Formula 6-3 when Q1 and Q2 are each a C6 aryl (phenyl) group, as pictured above.
With respect to claim 18, Choi and Fukuda teach the heterocyclic compound of claim 8, and R23 is represented by formula 7-1 and R13 is represented by formula 7-9, as pictured and discussed above.
With respect to claim 19, Choi and Fukuda teach the heterocyclic compound of claim 8, and R101 and R102 in Formula 2, are each a methyl group, as discussed above.
With respect to claim 20, Choi and Fukuda teach the heterocyclic compound of claim 8, and the compound is instant compound 14.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Sasaki et al. (US 2005/0084711 A1) – teaches relevant compounds
Oohisa et al. (US 2013/0341612 A1) – teaches relevant compounds
Bin et al. (KR 2012/0057198 A) – teaches relevant compounds
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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/R.S./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
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