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 .
Specification
The disclosure is objected to because of the following informalities:
On page 12, the image quality of the Formulae 1-1 to 1-6 is poor such that the variables are illegible. It is suggested to update with high resolution images.
Appropriate correction is required.
Claim Objections
Claim 3 is objected to because of the following informalities:
In claim 3, the image quality of the Formulae 1-1 to 1-6 is poor such that the variables are illegible. It is suggested to update with high resolution images.
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 2, 7 and 12 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 claim 2, Applicant recites “two adjacent R1s are connected … to form a substituted or unsubstituted C3-C10 cycloalkyl”, “two adjacent R2s are connected … to form a substituted or unsubstituted C3-C10 cycloalkyl”, “two adjacent R3s are connected … to form a substituted or unsubstituted C3-C10 cycloalkyl”. In the Formula 1’, the two carbon atoms as the members of the benzene ring are connected by a double bond, because the carbon atoms have each an sp2 hybridization. It is unclear how the C3-C10 ring containing sp2 carbon atoms can be cycloalkyl.
For the purpose of prosecution, the Examiner interprets the limitation to mean R1s are connected … to form a substituted or unsubstituted C5-C6 cycloalkene ring.
Regarding claim 7, Applicant recites “R1s are connected … to form a substituted or unsubstituted C5-C6 cycloalkyl”. In the Formula 1’, the two carbon atoms as the members of the benzene ring are connected by a double bond, because the carbon atoms have each an sp2 hybridization. It is unclear how the C5-C6 ring containing sp2 carbon atoms can be cycloalkyl.
For the purpose of prosecution, the Examiner interprets the limitation to mean R1s are connected … to form a substituted or unsubstituted C5-C6 cycloalkene ring.
Regarding claim 12, Applicant recites “two R3s are connected … to form a substituted or unsubstituted C5-C6 cycloalkyl”. In the Formula 1’, the two carbon atoms as the members of the benzene ring are connected by a double bond, because the carbons atoms have each an sp2 hybridization. It is unclear how the C5-C6 ring containing sp2 carbon atoms can be cycloalkyl.
For the purpose of prosecution, the Examiner interprets the limitation to mean R3s are connected … to form a substituted or unsubstituted C5-C6 cycloalkene ring.
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 1-13 and 16-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (US 2023/0096132 A1, hereafter Hatakeyama) in view of Jayabharathi et al. (“Tailoring the molecular design of twisted dihydrobenzodioxin phenanthroimidazole derivatives for non-doped blue organic light emitting devices” RSC Adv. 2018, vol. 8, page 29031-29043, hereafter Jayabharathi).
Regarding claims 1-6, 9-10, 12-13, and 16-22, Hatakeyama discloses a polycyclic compound comprising a fused cycloalkane ring ([0017]-[0022]) and used for an organic light emitting device ([0001]). Hatakeyama exemplifies Compound 1-1309 ([0132]).
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The Compound 1-1309 of Hatakeyama has a tetramethyl cyclohexane fused phenyl group (i.e. the part enclosed by a dashed circle in the figure above), which is not a benzo hydro dioxin ring having structure of
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that Applicant’s Formula 1 requires.
However, Hatakeyama does teach at least one -CH2- in the cycloalkane can be substituted by -O- ([0126]), and exemplifies a dihydrobenzodioxin group,
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([0126]).
Jayabharathi discloses a compound comprising a dihydrobenzodioxin group and used as the blue emitter of an organic light emitting device (Abstract, Fig. 1).
Jayabharathi teaches that the bulky dihydrobenzodioxin group provides enhanced amorphous film, reduced packing between molecules, enhanced stability of blue emission, and improved quantum efficiency (page 29032, col. 1, line 6-13; and page 29033, col. 2).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound 1-1309 of Hatakeyama by substituting the tetramethyl cyclohexyl fused phenyl group with a dihydrobenzodioxin group, as taught by Hatakeyama and Jayabharathi.
The motivation of doing so would have been to provide enhanced amorphous film, reduced packing between molecules, enhanced stability of blue emission, and improved quantum efficiency, based on the teaching of Jayabharathi.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The dihydrobenzodioxin group is an exemplified fused cycloalkane that Hatakeyama discloses. The substitution of the tetramethyl cyclohexyl fused phenyl group with a dihydrobenzodioxin group in the compound of Hatakeyama would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Hatakeyama as modified by Jayabharathi, meeting all the limitations of claims 1-6, 9-10, 12-13, and 16-20.
Hatakeyama in view of Jayabharathi does not disclose a specific organic light emitting device comprising the Compound of Hatakeyama as modified by Jayabharathi; however, Hatakeyama does teach that the compound of Hatakeyama can be used as the light emitting layer material of an organic light emitting device (items [26]-[28] of [0056]).
Hatakeyama teaches the structure of the organic light emitting device comprising a first electrode, a light emitting layer, and a second electrode ([0676])-[0677]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Hatakeyama as modified by Jayabharathi by incorporating it into the light emitting layer of an organic light emitting device, as taught by Hatakeyama.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Substitution of compounds of Hatakeyama in the device of Hatakeyama would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Hatakeyama as modified by Jayabharathi comprising a first electrode, a light emitting layer (Compound of Hatakeyama as modified by Jayabharathi), and a second electrode, meeting all the limitations of claims 21-22.
Regarding claims 7-8 and 11, the Compound of Hatakeyama as modified by Jayabharathi reads on all the features of claims 1-2 as outlined above.
The t-butyl groups as the substituents of the rings B and C and the phenyl ring at position X1 of Formula 1 of Hatakeyama are not cycloalkenyl ring; however, Hatakeyama does teach that the cycloalkane ring can be fused to any of the rings A, ring B, and aryl ring in the compound of Formula 1 of Hatakeyama can be fused with cycloalkane ([0022], see examples in [0132]).
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Hatakeyama teaches exemplary compounds (see examples including at least Compounds 1-1301, 1-1302, and 1-1311 in [0132]), wherein the substituents of the rings B and C and the substituent of the phenyl ring as the substituent of the X1 of Formula 1 of Hatakeyama are joined to form each a tetramethyl cyclohexene ring (see the moieties enclosed by dashed boxes in the figure above). Hatakeyama further teaches that when there are multiple fused cycloalkane rings in a compound, each of the fused cycloalkane rings can be different (see examples including at least compounds 1-233 and 1-409).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Hatakeyama as modified by Jayabharathi by substituting each of the t-butyl groups with tetramethyl cyclohexene ring, as taught by Hatakeyama.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Substitution of the substituents of the rings B and C and the phenyl ring substituted to the nitrogen at X1 of Formula 1 of Hatakeyama with each a tetramethyl cyclohexene ring would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Hatakeyama as modified by Jayabharathi (2).
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Claims 1-13, 16, 18-19, and 21-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (US 2023/0096132 A1) in view of Jayabharathi et al. (“Tailoring the molecular design of twisted dihydrobenzodioxin phenanthroimidazole derivatives for non-doped blue organic light emitting devices” RSC Adv. 2018, vol. 8, page 29031-29043) and Sun et al. (“A Novel Spiro[acridine-9,9’-fluorene] Derivatives Containing Phenanthroimidazole Moiety for Deep-Blue OLED Application”, Chem. Asian J. 2017, vol. 12, page 3069-3076, hereafter Sun).
Regarding claims 1-13, 16, 18-19, and 21-22, Hatakeyama discloses a polycyclic compound comprising a fused cycloalkane ring ([0017]-[0022]) and used for an organic light emitting device ([0001]). Hatakeyama exemplifies Compound 1-1313 ([0132]).
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The Compound 1-1313 of Hatakeyama has t-butyl phenyl groups at the positions corresponding to R of the NR at X1 and X2 of Formula 1 of Hatakeyama (i.e. the part enclosed by dashed boxes in the figure above), each of which is not a benzo hydro dioxin ring having structure of
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that Applicant’s Formula 1 requires.
However, Hatakeyama does teach that the aryl groups of the compound can be each substituted by a fused cycloalkane group ([0022]). Hatakeyama teaches cyclohexane as the fused cycloalkane ([0123]). Hatakeyama teaches at least one -CH2- in the cycloalkane can be substituted by -O- ([0126]), and exemplifies a dihydrobenzodioxin group,
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([0126]).
Jayabharathi discloses a compound comprising a dihydrobenzodioxin group and used as the blue emitter of an organic light emitting device (Abstract, Fig. 1).
Jayabharathi teaches that the bulky dihydrobenzodioxin group provides enhanced amorphous film, reduced packing between molecules, enhanced stability of blue emission, and improved quantum efficiency (page 29032, col. 1, line 6-13; and page 29033, col. 2).
Jayabharathi teaches the dihydrobenzodioxin group has a dihedral angle of 89° from the phenanthrimidazole core plane (page 29033, col. 2, line 4), which provides suppressed formation of aggregation, amorphous film, suppressed intermolecular interaction, increased glass transition temperature (page 29033, col. 2).
Sun discloses a phenanthrimidazole compound substituted by a t-butyl phenyl group at the position corresponding to the dihydrobenzodioxin group of the phenanthrimidazole compound of Jayabharathi (Scheme 1). Sun teaches the dihedral angle of the t-butyl phenyl group is 81° from the phenanthrimidazole core plane (Fig. S5). Thus, an ordinary skill in the art would understand dihydrobenzodioxin group provide higher dihedral angle, which would provide more orthogonal and bulkier structure.
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound 1-1313 of Hatakeyama by substituting each of the t-butyl phenyl groups with a dihydrobenzodioxin group, as taught by Hatakeyama, Jayabharathi, and Sun.
The motivation of doing so would have been to provide enhanced amorphous film, reduced packing between molecules, enhanced stability of blue emission, and improved quantum efficiency, based on the teaching of Jayabharathi and Sun.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The dihydrobenzodioxin group is an exemplified fused cycloalkane that Hatakeyama discloses. The substitution of the substituents of the phenyl groups at the positions R of the X1 and X2 of the Formula 1 of Hatakeyama with a dihydrobenzodioxin group would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Hatakeyama as modified by Jayabharathi and Sun, meeting all the limitations of claims 1-13, 16, and 18-19.
It is noted that in claims 7-8, the dihydrobenzodioxin on the right side of the molecule is
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such that the tetramethyl cyclohexene ring reads on the limitations of R1. In claim 11, the dihydrobenzodioxin on the left side of the molecule is
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such that the tetramethyl cyclohexene ring reads on the limitations of R2.
Hatakeyama in view of Jayabharathi and Sun does not disclose a specific organic light emitting device comprising the Compound of Hatakeyama as modified by Jayabharathi and Sun; however, Hatakeyama does teach that the compound of Hatakeyama can be used as the light emitting layer material of an organic light emitting device (items [26]-[28] of [0056]).
Hatakeyama teaches the structure of the organic light emitting device comprising a first electrode, a light emitting layer, and a second electrode ([0676])-[0677]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Hatakeyama as modified by Jayabharathi and Sun by incorporating it into the light emitting layer of an organic light emitting device, as taught by Hatakeyama.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Substitution of compounds of Hatakeyama in the device of Hatakeyama would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Hatakeyama as modified by Jayabharathi comprising a first electrode, a light emitting layer (Compound of Hatakeyama as modified by Jayabharathi and Sun), and a second electrode, meeting all the limitations of claims 21-22.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP §§ 706.02(l)(1) - 706.02(l)(3) for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1, 4, and 21-22 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 15, and 17 of copending Application18/271,329 (reference application, hereafter Application ‘329). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims are directed at the same aspects of the same invention. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Regarding claims 1, 4, and 21-22, Application ‘329 discloses a compound of Chemical Formula 1 and exemplifies a compound (the first compound of claim 15, hereafter Compound A).
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The Compound A of Application ‘329 has identical structure as Applicant’s Chemical Formula 1, meeting all the limitations of claims 1 and 4.
Application ‘329 does not disclose a specific organic light emitting device comprising the Compound A of Application ‘329; however, Application ‘329 does teach an organic light emitting device comprising a first electrode, a light emitting layer comprising the compound of Application ‘329, and a second electrode (claim 17).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound A of Application ‘329 by incorporating it into the light emitting layer of an organic light emitting device, as taught by Application ‘329.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified organic light emitting device of Application ‘329 comprising a first electrode, a light emitting layer (Compound A), and a second electrode, meeting all the limitations of claims 21-22.
Claims 1, 4, and 21-22 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 9, and 11 of copending Application18/565,302 (reference application, hereafter Application ‘302). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims are directed at the same aspects of the same invention. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Regarding claims 1, 4, and 21-22, Application ‘302 discloses a compound of Chemical Formula 1 and exemplifies a compound (the third compound of claim 9, hereafter Compound B).
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The Compound B of Application ‘302 has identical structure as Applicant’s Chemical Formula 1, meeting all the limitations of claims 1 and 4.
Application ‘302 does not disclose a specific organic light emitting device comprising the Compound B of Application ‘302; however, Application ‘302 does teach an organic light emitting device comprising a first electrode, a light emitting layer comprising the compound of Application ‘302, and a second electrode (claim 11).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound B of Application ‘302 by incorporating it into the light emitting layer of an organic light emitting device, as taught by Application ‘302.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified organic light emitting device of Application ‘302 comprising a first electrode, a light emitting layer (Compound B), and a second electrode, meeting all the limitations of claims 21-22.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SEOKMIN JEON whose telephone number is (571)272-4599. The examiner can normally be reached Monday - Friday 8:30am to 5:00pm EST.
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786
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