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 .
Examiner’s Note
A second Non-final rejection Office Action is provided here to update the previous Non-final rejection Office Action of 03/25/2026 which omitted 112(b) and 112(d) rejections to claims 24-25. The 103 rejections of the previous Office Action have been updated.
Election/Restrictions
Applicant's election without traverse of Species (B), a complex of General Formula (X) wherein two adjacent groups R2 represent Formula A (claim 14), in the reply filed on 4/7/2025 is acknowledged.
Claim 17 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group.
Response to Amendment
The amendment of 06/25/2026 has been entered.
Disposition of claims:
Claims 11-12, 14-21, 24-25, and 27-34 are pending.
Claim 17 is withdrawn.
Claim 30 has been amended.
The amendment of claim 30 have overcome the objection of claim 30 set forth in the last Office Action. The Objection has been withdrawn.
Response to Arguments
Applicant’s arguments see the page 8-11 of the reply filed 06/25/2026 regarding The rejections of claims 11-12, 14-16, 18-21, 24-25, 27, and 29-34 under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2013/0168656 A1) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to, hereafter Noboru), Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective” ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo), Blondel et al. (“Investigation of a sterically hindered Pt(II) complex to avoid aggregation-induced quenching: Applications in deep red electroluminescent and electrical switching devices” Syn. Metal 2017, vol. 227, page 106-116, hereafter Blondel), Forrest et al. (US 2005/0260444 A1, hereafter Forrest), and Li et al. (US 2015/016552 A1, hereafter Li) and the rejections of claims 28, 30-31 and 34 under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2013/0168656 A1) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to) set forth in the Office Action of 03/25/2026 have been considered.
Applicant compares the inventive Compound with the Compound of Tsai, Noboru, Blondel, Forrest, and Li (see figures on page 10) Applicant argues that the inventive compounds, especially the compound of instant claims 15 and 32, have steric effect such that a person having ordinary skill in the art would immediately realize that this profound steric effect would result in a significant deviation from the planarity that the compound of prior arts have. Applicant further argues that the positional isomerism of the compound of Tsai, Noboru, Luo, Blondel, Forrest, and Li would have no reasonable expectation of similar properties as the inventive compound (page 11).
Respectfully, the Examiner does not agree.
Applicant’s arguments are directed to the unexpected results of relatively less planar and less stable inventive compound as compared to relatively more planar and more stable comparative compound which is Compound of Li ‘555 as modified by Noboru. The arguments are not found persuasive for at least following reasons.
First, the arguments are not based on factual evidence.
The arguments of counsel cannot take the place of evidence in the record. In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965). Examples of attorney statements which are not evidence and which must be supported by an appropriate affidavit or declaration include statements regarding unexpected results, commercial success, solution of a long-felt need, inoperability of the prior art, invention before the date of the reference, and allegations that the author(s) of the prior art derived the disclosed subject matter from the inventor or at least one joint inventor. MPEP 716.01(C) II.
While Applicant’s arguments are based on the geometry and energy of the inventive and comparative compounds, Applicant fails to provide data such as the energy of the optimized molecular structures calculated by DFT calculations and verified by experiments. The structural formulae on page 10 are drawings, not optimized molecular structures. It is unclear how stable the comparative compound is in energy and how distorted the Inventive compound is in optimized structure, and the calculated numbers should be verified by comparing with experimental values.
Second, Applicant fails to prove that the advantages of the inventive compound are practically and statistically significant.
The evidence relied upon should establish "that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance." Ex parte Gelles, 22 USPQ2d 1318, 1319 (Bd. Pat. App. & Inter. 1992) (Mere conclusions in appellants’ brief that the claimed polymer had an unexpectedly increased impact strength "are not entitled to the weight of conclusions accompanying the evidence, either in the specification or in a declaration."); Ex parte C, 27 USPQ2d 1492 (Bd. Pat. App. & Inter. 1992) (Applicant alleged unexpected results with regard to the claimed soybean plant, however there was no basis for judging the practical significance of data with regard to maturity date, flowering date, flower color, or height of the plant.). See also In re Nolan, 553 F.2d 1261, 1267, 193 USPQ 641, 645 (CCPA 1977) and In re Eli Lilly, 902 F.2d 943, 14 USPQ2d 1741 (Fed. Cir. 1990) as discussed in MPEP § 716.02(c).
It is Applicant’s burden to show the superior and unexpected results of the inventive compound to argue non-obviousness of the closest prior art, Compound of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li.
Third, the displayed inventive compound is not commensurate in scope with the claims.
With respect to the commensurate in scope with claimed invention, the Examiner points out MPEP 716.02(d), as recited below.
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range.
In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980) (Claims were directed to a process for removing corrosion at "elevated temperatures" using a certain ion exchange resin (with the exception of claim 8 which recited a temperature in excess of 100C). Appellant demonstrated unexpected results via comparative tests with the prior art ion exchange resin at 110C and 130C. The court affirmed the rejection of claims 1-7 and 9-10 because the term "elevated temperatures" encompassed temperatures as low as 60C where the prior art ion exchange resin was known to perform well. The rejection of claim 8, directed to a temperature in excess of 100C, was reversed.). See also In re Peterson, 315 F.3d 1325, 1329-31, 65 USPQ2d 1379, 1382-85 (Fed. Cir. 2003) (data showing improved alloy strength with the addition of 2% rhenium did not evidence unexpected results for the entire claimed range of about 1-3% rhenium); In re Grasselli, 713 F.2d 731, 741, 218 USPQ 769, 777 (Fed. Cir. 1983) (Claims were directed to certain catalysts containing an alkali metal. Evidence presented to rebut an obviousness rejection compared catalysts containing sodium with the prior art. The court held this evidence insufficient to rebut the prima facie case because experiments limited to sodium were not commensurate in scope with the claims.).
Not all the claims are directed to the Inventive Compound on page 10. For example, the instant claim 11 allows the X2 and Y4b of Formula A to be bonded to Y2d and Y2e in Formula X. Additionally, at least claims 24, 25, and 28 are not directed to the Inventive Compound on page 10.
While Applicant fails to show non-obviousness, there are reasons why an ordinary skill in the art would achieve the benzofurocarbazole moiety of the inventive compound from the carbazole moiety of the compound of Tsai.
Tsai discloses Compound 14 ([0061]).
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The Compound 14 of Tsai does not have a benzo-five-membered ring fused to the carbazole; however, Tsai does teach that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]).
Tsai, Noboru, Luo, and Li teaches the Complex of Tsai as modified by Noboru, Luo, and Li based on similar reasoning provided in the previous Office Action (See section 52 to 78. Note that teachings of Blondel and Forrest are similar to those of Luo and Li such that the references are excluded in this Office Action to simplify the rejection).
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The complex does not read on all the limitation of the General Formula X of the claim 11. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure above) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group. However, Tsai does teach that R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]), indicating there is no restriction on the fusion position of the benzofuran ring.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-1) below).
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The benzofuro carbazole moieties of the Complex of Tsai as modified by Noboru, Luo, and Li corresponds to the Formula (Q-4). However, the benzofuro moiety can be attached to the carbazole moiety similarly as in the Formula (Q-1) because both Formulas (Q-4) and (Q-1) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
Finally, both Complex of Tsai as modified by Noboru, Luo, and Li and the claimed compound are position isomers to each other because the only difference between two compounds is the fusion position of the benzofuran ring.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Tsai as modified by Noboru, Luo, and Li by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group similarly as Formula (Q-1) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the hydrogen and aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-4) and (Q-1) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-1) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified 6-5-6-5-6 structures in the disclosure of Noboru (Formulae (Q-1) to (Q-5) in [0076]). The selection of Formula (Q-1) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
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The modification provides Compound of Tsai as modified by Noboru, Luo, and Li (2) which has identical structure as Applicant’s General Formula X.
For at least the reason, the arguments are not found persuasive.
Applicant’s arguments see the page 12-14 of the reply filed 06/25/2026 regarding the rejections of claims 11-12, 14-16, 18-21, 24-25, 27, and 29-34 under 35 U.S.C. 103 as being unpatentable over Li et al. (US 2017/0040555 A1, hereafter Li ‘555) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to) set forth in the Office Action of 03/25/2026 have been considered.
Applicant argues that at the position corresponding to instant Y1b, a carbon atom which is substituted with a substituent selected from the group consisting of hydrogen, deuterium, trideuteriummethyl, pentadeuteriumphenyl, halogen, hydroxy, nitro, nitrile, thiol; or substituted or unsubstituted, amino, alkoxy, aryl, or C1-C4 alkyl, and Li ‘555 in view of Noboru does not teach or suggest each and every element of the present claim.
Respectfully, the Examiner does not agree.
Updated rejections refer to the Complex of Li ‘555 as modified by Noboru (2) (see 103 rejection section below).
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The Complex of Li ‘555 as modified by Noboru reads on all the limitations of Formula X of the instant claims. In the independent claims 11 and 31, Y1b can be C; R1 can be hydrogen or t-butyl group; and n can be 3. The claims allow Y1b to be “C” as long as the valency is permitted. None of the claims require the carbon at position Y1b to be substituted by R1. The variable n is 3; and the R1 groups exist at positions Y1c, Y1d, and Y1e, not positions Y1a, Y1b, and Y1f. The valency are still permitted. Please, compare the carbon atoms at the positions Y1f with Y1b. The carbon at Y1f has the same valency as the carbon at Y1b in the Complex of Li ‘555 as modified by Noboru, wherein both Y1f and Y1b do not have any substituent R1 but reads on all the limitations of Formula X. The valence electrons of the carbon atoms at the positions Y1b having no substituent are connected to each other to form a direct bond such that the valency is permitted. The compound reads on all the limitations of Applicant’s General Formula X.
For at least this reason, the arguments are not found persuasive.
Claim Rejections - 35 USC § 112
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 24-25 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 24, claim 24 recites “The complex of claim 11, wherein the complex is represented by General Formula V”. However, the General Formula V is not encompassed by General Formula X of claim 11, because claim 11 recites “provided that Y2c and Y2d do not together form a group of Formula A” and in the General Formula V, Y2c and Y2d together forms a group of Formula A. Currently claim 24 is dependent from claim 11. It is unclear whether Applicant claims General Formula V in claim 24, rendering this claim indefinite.
For the purpose of prosecution, the Examiner interprets the limitation to mean that Applicant claims General Formula V in claim 24 although the formula is not encompassed by General Formula X of claim 11 (i.e. similarly as handling claim 24 as an independent claim).
Regarding claim 25, claim 25 recites “The complex of claim 11, wherein the complex is represented by General Formula VI”. However, the General Formula VI is not encompassed by General Formula X of claim 11, because claim 11 recites “provided that Y2c and Y2d do not together form a group of Formula A” and in the General Formula VI, Y2c and Y2d together forms a group of Formula A. Currently claim 25 is dependent from claim 11. It is unclear whether Applicant claims General Formula VI in claim 25, rendering this claim indefinite.
For the purpose of prosecution, the Examiner interprets the limitation to mean that Applicant claims General Formula VI in claim 25 although the formula is not encompassed by General Formula X of claim 11 (i.e. similarly as handling claim 25 as an independent claim).
Claims 24-25 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.
Regarding claim 24, claim 24 recites “The complex of claim 11, wherein the complex is represented by General Formula V”. However, the General Formula V is not encompassed by General Formula X of claim 11, because claim 11 recites “provided that Y2c and Y2d do not together form a group of Formula A” and in the General Formula V, Y2c and Y2d together forms a group of Formula A. Currently claim 24 is dependent from claim 11. Therefore, claim 24 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.
Regarding claim 25, claim 25 recites “The complex of claim 11, wherein the complex is represented by General Formula VI”. However, the General Formula VI is not encompassed by General Formula X of claim 11, because claim 11 recites “provided that Y2c and Y2d do not together form a group of Formula A” and in the General Formula VI, Y2c and Y2d together forms a group of Formula A. Currently claim 25 is dependent from claim 11. Therefore, claim 25 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 § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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 11-12, 14-16, 18-21, 24-25, 27, and 29-34 are rejected under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2013/0168656 A1) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to, hereafter Noboru), Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective” ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo), and Li et al. (US 2015/016552 A1, hereafter Li).
Regarding claim 24, Tsai discloses a complex represented by Formulas I ([0049]) and more detailed structure represented by Formula III ([0056]). Tsai exemplifies Compound 14 ([0061]).
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The Compound 14 of Tsai does not have a benzo-five-membered ring fused to the carbazole; however, Tsai does teach that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]).
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Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]; and see the part enclosed by a dashed circle in the figure above).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
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 14 of Tsai by substituting each of the carbazole moieties of the compound with benzofurocarbazole as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Tsai teaches the substituents at the positions R2 and R3 of Formulas I and III of Tsai can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). The substitution of hydrogen with a fused benzofuran ring in the compound of Tsai 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 Complex of Tsai as modified by Noboru.
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The Compound of Tsai as modified by Noboru does not have t-butyl group at the positions corresponding to the R1 and R4 of Formula III of Tsai is required to be each a t-butyl group; however, Tsai does teach that R1 and R4 can be alkyl ([0049]).
Luo discloses a Pt complex used for an organic light emitting device (page 69, col. 1, first paragraph).
Luo teaches that a t-butyl group is extensively used as substituent unit in transition metal complexes and the steric property of the t-butyl group provides suppressed intermolecular interactions and improved efficiency and color purity (page 69, col. 2, line 8-13).
Li teaches that addition of tert-butyl group provides improved thermal stability ([0128]). The tert-butyl group is substituted to the position 4 of the pyridine ring of the pyridinyl carbazole ligand (see t-butyl group in the compounds PtON6-tBu and PtON7-dtb in Fig. 30C and 30D).
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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 Tsai as modified by Noboru by substituting the isopropyl group at the positions corresponding to R1 and R4 of Formula III of Tsai with each t-butyl group, as taught by Tsai, Luo, and Li.
The motivation of doing so would have been to provide provides suppressed intermolecular interactions and improved efficiency and color purity based on the teaching of Luo and provide improved thermal stability based on the teaching of Li.
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 substitution of isopropyl with t-butyl at the position corresponding to R1 of Formula I of Zeng would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
Additionally, a compound having an isopropyl group is a homolog – a compound differing regularly by the successive addition of the same chemical groups, in the present instance, a CH3 group, of a compound in which the compound having the same skeletal structure except the isopropyl is substituted by a t-butyl group.
With respect to homologs, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See MPEP 2144.09 I and 2144.09 II.
Therefore, at the time the invention was effectively filed, it would have been obvious to one with ordinary skill in the art to have modified Compound of Tsai as modified by Noboru such that the isopropyl groups are substituted by each a t-butyl group. A compound comprising t-butyl groups would be a homolog of the Compound of Tsai as modified by Noboru.
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The modification provides Compound of Tsai as modified by Noboru, Luo, and Li, which has identical structure as Applicant’s General Formula X.
Regarding claims 11-12, 14-15, 18-20, 29-30, and 31-34, the Complex of Tsai as modified by Noboru, Luo, and Li reads on all the features of claim 24 as outlined above.
The complex does not read on all the limitation of the General Formula X of the claim 11. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure above) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group. However, Tsai does teach that R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]), indicating there is no restriction on the fusion position of the benzofuran ring.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-1) below).
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The benzofuro carbazole moieties of the Complex of Tsai as modified by Noboru, Luo, and Li corresponds to the Formula (Q-4). However, the benzofuro moiety can be attached to the carbazole moiety similarly as in the Formula (Q-1) because both Formulas (Q-4) and (Q-1) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
Finally, both Complex of Tsai as modified by Noboru, Luo, and Li and the claimed compound are position isomers to each other because the only difference between two compounds is the fusion position of the benzofuran ring.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
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 Complex of Tsai as modified by Noboru, Luo, and Li by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group similarly as Formula (Q-1) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the hydrogen and aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-4) and (Q-1) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-1) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified 6-5-6-5-6 structures in the disclosure of Noboru (Formulae (Q-1) to (Q-5) in [0076]). The selection of Formula (Q-1) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
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The modification provides Compound of Tsai as modified by Noboru, Luo, and Li (2), which has identical structure as Applicant’s General Formula X, meeting all the limitations of claims 11-12, 14-15, 18-20, and 31-34.
Tsai in view of Noboru, Luo, and Li does not disclose a specific an organic light emitting device comprising the Complex of Tsai as modified by Noboru, Luo, and Li (2); however, Tsai does teach that the compound of Tsai can be incorporated in an organic light emitting device ([0027] and examples in [0071]-[0072]).
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 Complex of Tsai as modified by Noboru, Luo, and Li (2) by incorporating it into an organic light emitting device, as taught by Tsai.
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 substitution of compounds of Tsai in an OLED device of Tsai 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 Tsai as modified by Noboru, Luo, and Li comprising the Complex of Tsai as modified by Noboru, Luo, and Li (2), meeting all the limitations of claims 29-30.
Regarding claim 21, the Complex of Tsai as modified by Noboru, Luo, and Li (2) reads on all the features of claim 11 as outlined above.
The complex does not read on all the limitations of claim 21. The only deficiency of the Complex of Tsai as modified by Noboru, Luo, and Li is that the atom at the position corresponding to X2 is required to be S; however, Tsai does teach that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen, aryl, or sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]).
Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
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 Complex of Tsai as modified by Noboru, Luo, and Li by substituting the oxygen atom at the position corresponding to X2 of the General Formula X with sulfur as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Tsai teaches the substituents at the positions R2 and R3 of Formulas I and III of Tsai can be sulfanyl (i.e. -SH) and aryl (i.e. phenyl); and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). The substitution of hydrogen with a fused benzofuro ring in the compound of Tsai would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Noboru exemplifies a benzofurocarbazole group which is represented by the Formula (Q-4) of Noboru. Noboru teaches X1 and X2 of Formula (Q-4) can be O or S; thus, substitution of O with S in the Formula (Q-4) of Noboru 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 Complex of Tsai as modified by Noboru, Luo, and Li (2).
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Regarding claims 16 and 27, the Complex of Tsai as modified by Noboru, Luo, and Li (2) reads on all the features of claim 11 as outlined above.
The Complex of Tsai as modified by Noboru, Luo, and Li (2) does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 4 and 3 of the benzene ring of the carbazole group. However, Tsai does teach that R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]), indicating there is no restriction on the attachment position of the benzofuran ring.
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Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-1) and (Q-5) below).
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The benzofuro carbazole moieties of the Complex of Tsai as modified by Noboru, Luo, and Li corresponds to the Formula (Q-1). However, the benzofuro moiety can be attached to the carbazole moiety similarly as in the Formula (Q-5) because both Formulas (Q-1) and (Q-5) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
Finally, both Complex of Tsai as modified by Noboru, Luo, and Li (2) and the claimed compound are position isomers to each other because the only difference between two compounds is the fusion position of the benzofuran ring.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
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 Complex of Tsai as modified by Noboru, Luo, and Li (2) by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 4 and 3 of the benzene ring of the carbazole group similarly as Formula (Q-5) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the hydrogen and aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-1) and (Q-5) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-1) to (Q-5) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified 6-5-6-5-6 structures in the disclosure of Noboru (Formulae (Q-1) to (Q-5) in [0076]). The selection of Formula (Q-5) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides the Position isomer of complex of Tsai as modified by Noboru, Luo, and Li (4) (see the structure in the figure above).
Regarding claim 25, the Complex of Tsai as modified by Noboru, Luo, and Li (2) reads on all the features of claim 11 as outlined above.
The Complex of Tsai as modified by Noboru, Luo, and Li (2) does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 2 and 3 of the benzene ring of the carbazole group. However, Tsai does teach that R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]), indicating there is no restriction on the attachment position of the benzofuran ring.
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Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-1) and (Q-2) below).
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The benzofuro carbazole moieties of the Complex of Tsai as modified by Noboru, Luo, and Li (2) corresponds to the Formula (Q-1). However, the benzofuro moiety can be attached to the carbazole moiety similarly as in the Formula (Q-2) because both Formulas (Q-1) and (Q-2) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
Finally, both Complex of Tsai as modified by Noboru, Luo, and Li (2) and the claimed compound are position isomers to each other because the only difference between two compounds is the fusion position of the benzofuran ring.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
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 Complex of Tsai as modified by Noboru, Luo, and Li (2) by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 2 and 3 of the benzene ring of the carbazole group similarly as Formula (Q-2) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the hydrogen and aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-1) and (Q-2) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-1) to (Q-2) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified 6-5-6-5-6 structures in the disclosure of Noboru (Formulae (Q-1) to (Q-5) in [0076]). The selection of Formula (Q-2) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides the Position isomer of complex of Tsai as modified by Noboru, Luo, and Li (5) (see the structure in the figure above).
Claims 28, 30-31 and 34 are rejected under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2013/0168656 A1) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to).
Regarding claims 28, 30-31 and 34, Tsai discloses a complex represented by Formulas I ([0049]) and more detailed structure represented by Formula III ([0056]). Tsai exemplifies Compound 1 ([0061]).
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Tsai exemplifies an organic light-emitting device comprising Compound 1 of Tsai (Device Ex. 1 in [0071]- [0072] and Table 2) wherein the device comprises an anode (ITO), an organic light emitting layer comprising Compound 1 of Tsai, and a cathode (Al).
The Compound 1 of Tsai does not have a benzo-five-membered ring fused to the carbazole; however, Tsai does teach that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]).
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Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]; and see the part enclosed by a dashed circle in the figure above).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
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 of Tsai by substituting each of the carbazole moieties of the compound with benzofurocarbazole as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Tsai teaches the substituents at the positions R2 and R3 of Formulas I and III of Tsai can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). The substitution of hydrogen with a fused benzofuran ring in the compound of Tsai 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 Complex of Tsai as modified by Noboru as shown below.
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The Complex of Tsai as modified by Noboru has similar structure as the second compound of claim 28. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure above) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group. However, Tsai does teach that R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]), indicating there is no restriction on the fusion position of the benzofuran ring.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-1) below).
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The benzofuro carbazole moieties of the Complex of Tsai as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety can be attached to the carbazole moiety similarly as in the Formula (Q-1) because both Formulas (Q-4) and (Q-1) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
Finally, both Complex of Tsai as modified by Noboru and the claimed compound are position isomers to each other because the only difference between two compounds is the fusion position of the benzofuran ring.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
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 Complex of Tsai as modified by Noboru by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group similarly as Formula (Q-1) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the hydrogen and aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-4) and (Q-1) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-1) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified 6-5-6-5-6 structures in the disclosure of Noboru (Formulae (Q-1) to (Q-5) in [0076]). The selection of Formula (Q-1) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides Compound of Tsai as modified by Noboru (2) (see figure above), which has identical structure as the second compound of claim 28, meeting all the limitations of claims 28, 31, and 34.
The modification also provides Organic light emitting device of Tsai as modified by Noboru comprising an anode (ITO), an organic light emitting layer comprising the complex of Tsai as modified by Noboru (2), and a cathode (Al), meeting all the limitations of claim 30.
Claims 11-12, 14-16, 18-21, 24-25, 27, and 29-34 are rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (US 2017/0040555 A1, hereafter Li ‘555) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to).
Regarding claim 24, Li ‘555 discloses a complex represented by Formulas I ([0008]) used for an organic light emitting device ([0002]) and exemplifies a compound PtNONc-dtb ([0132]).
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Li ‘555 does not disclose a specific organic light emitting device comprising the PtNONc-dtb of Li ‘555; however, Li does teach that the compound can be used in the light emitting layer or an organic light emitting device ([0125]).
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 PtNONc-dtb by incorporating it into the light emitting layer of an organic light emitting device, as taught by Li ‘555.
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 of light emitting dopant materials in an organic light emitting device 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 comprising the compound PtNONc-dtb of Li ‘555.
The compound PtNONc-dtb of Li ‘555 has similar structure as Applicants Formula X of the instant claims. The only difference is the carbazole moieties of the compound does not have a benzo-five-membered ring fused to the carbazole.
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Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]; and see the part enclosed by a dashed circle in the figure above).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
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 PtNONc-dtb of Li ‘555 by substituting each of the carbazole moieties of the compound with benzofurocarbazole as taught by Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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).
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The modification provides Complex of Li ‘555 as modified by Noboru, which has identical structure as Applicant’s General Formula X.
It is noted that in the Complex of Li ‘555 as modified by Noboru, the variable n of each of the (R1)n groups is 3, wherein R1 are each hydrogen or a t-butyl group. The atom at the positions corresponding to Y1b are each carbon. Note that the claims allow Y1b to be “C”. None of the claims require the carbon at Y1b to be substituted by R1, because n can be selected to 3 and valency is permitted. Compare the carbon at the position corresponding to Y1f which has equivalent to the carbon at Y1b in the Complex of Li ‘555 as modified by Noboru. In the complex, the valence electrons of the carbon atoms at the positions Y1b having no substituent are connected to each other to form a direct bond; thus, the compound reads on all the limitations of Applicant’s Formula X.
Regarding claims 11-12, 14-15, 18-20, and 29-34, Complex of Li ‘555 as modified by Noboru reads on all the features of claim 24 as outlined above.
The Complex of Li ‘555 as modified by Noboru does not read on all the limitation of the General Formula X of claim 11. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure above) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group.
However, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-1) below).
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The benzofuro carbazole moieties of the Complex of Li ‘555 as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety can be attached to the carbazole moiety similarly as in the Formula (Q-1) because both Formulas (Q-4) and (Q-1) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
Furthermore, both Complex of Li ‘555 as modified by Noboru and the claimed compound are position isomers to each other.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
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 Complex of Li ‘555 as modified by Noboru by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group similarly as Formula (Q-1) of Noboru, as taught by Li ‘555 and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Both Formulas (Q-4) and (Q-1) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-1) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified 6-5-6-5-6 structures in the disclosure of Noboru (Formulae (Q-1) to (Q-5) in [0076]). The selection of Formula (Q-1) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides Complex of Li ‘555 as modified by Noboru (2), which has identical structure as Applicant’s General Formula X, meeting all the limitations of claims 11-12, 14-15, 18-20, and 31-34.
It is noted that in the Complex of Li ‘555 as modified by Noboru, the variable n of each of the (R1)n groups is 3, wherein R1 are each hydrogen or a t-butyl group. The atom at the positions corresponding to Y1b are each carbon. Note that the claims allow Y1b to be “C”. None of the claims require the carbon at Y1b to be substituted by R1, because n can be selected to 3 and valency is permitted. Compare the carbon at the position corresponding to Y1f which has equivalent to the carbon at Y1b in the Complex of Li ‘555 as modified by Noboru. In the complex, the valence electrons of the carbon atoms at the positions Y1b having no substituent are connected to each other to form a direct bond; thus, the compound reads on all the limitations of Applicant’s Formula X.
The modification also provides Organic light emitting device of Li ‘555 as modified by Noboru comprising the Complex of Li ‘555 as modified by Noboru, meeting all the limitations of claims 29-30.
Regarding claim 21, the Complex of Li ‘555 as modified by Noboru (2) reads on all the features of claim 11 as outlined above.
The complex does not read on all the limitations of claim 21. The only deficiency of the Complex of Li ‘555 as modified by Noboru is that the atom at the position corresponding to X2 is required to be S; however, Noboru teaches the oxygen atom at the position corresponding to X2 can be sulfur.
Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
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 Complex of Li ‘555 as modified by Noboru (2) by substituting the oxygen atom at the position corresponding to X2 of the General Formula X with sulfur as taught by Li ‘555 and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Noboru exemplifies a benzofurocarbazole group which is represented by the Formula (Q-4) of Noboru. Noboru teaches X1 and X2 of Formula (Q-4) can be O or S; thus, substitution of O with S in the Formula (Q-4) of Noboru 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 Complex of Li ‘555 as modified by Noboru (3).
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Regarding claims 16 and 27, the Complex of Li ‘555 as modified by Noboru (2) reads on all the features of claim 11 as outlined above.
The Complex of Li ‘555 as modified by Noboru (2) does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 4 and 3 of the benzene ring of the carbazole group.
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However, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-1) and (Q-5) below).
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The benzofuro carbazole moieties of the Complex of Li ‘555 as modified by Noboru (2) corresponds to the Formula (Q-1). However, the benzofuro moiety can be attached to the carbazole moiety similarly as in the Formula (Q-5) because both Formulas (Q-1) and (Q-5) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
Furtehrmore, both Complex of Li ‘555 as modified by Noboru (2) and the claimed compound are position isomers to each other.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
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 Complex of Li ‘555 as modified by Noboru (2) by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 4 and 3 of the benzene ring of the carbazole group similarly as Formula (Q-5) of Noboru, as taught by Li ‘555 and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Both Formulas (Q-1) and (Q-5) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-1) to (Q-5) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified 6-5-6-5-6 structures in the disclosure of Noboru (Formulae (Q-1) to (Q-5) in [0076]). The selection of Formula (Q-5) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides the Position isomer of complex of Li ‘555 as modified by Noboru (4) (see the structure in the figure above).
Regarding claim 25, the Complex of Li ‘555 as modified by Noboru (2) reads on all the features of claim 11 as outlined above.
The Complex of Li ‘555 as modified by Noboru does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 2 and 3 of the benzene ring of the carbazole group.
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However, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-1) and (Q-2) below).
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The benzofuro carbazole moieties of the Complex of Li ‘555 as modified by Noboru corresponds to the Formula (Q-1). However, the benzofuro moiety can be attached to the carbazole moiety similarly as in the Formula (Q-2) because both Formulas (Q-1) and (Q-2) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
Furthermore, both Complex of Li ‘555 as modified by Noboru (2) and the claimed compound are position isomers to each other.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
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 Complex of Li ‘555 as modified by Noboru (2) by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 2 and 3 of the benzene ring of the carbazole group similarly as Formula (Q-2) of Noboru, as taught by Li ‘555 and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
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). Both Formulas (Q-1) and (Q-2) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-1) to (Q-2) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of exemplified 6-5-6-5-6 structures in the disclosure of Noboru (Formulae (Q-1) to (Q-5) in [0076]). The selection of Formula (Q-2) would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
The modification provides the Complex of Li ‘555 as modified by Noboru (5) (see the structure in the figure above).
Conclusion
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786
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