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 .
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Response to Amendment
The amendment of 21 November 2025 has been entered.
Disposition of claims:
Claims 1 and 16-17 have been amended.
Claims 3-5 and 10 are cancelled.
Claim 13 is withdrawn from consideration.
Claims 1-2, 6-9, and 11-17 are pending.
The amendment to claim 1 has overcome the rejections of claims 1-2, 6, and 8 under 35 U.S.C. 102(a)(2) as being anticipated by Sugawara et al. (WO 2020/059520 A1—US 2021/0340160 A1) (hereafter “Sugawara”) set forth in the last Office action. The rejections have been withdrawn. However, as outlined below, new grounds of rejection have been made.
The amendment to claim 1 has overcome the rejections of claims 1-2, 6, and 8 under 35 U.S.C. 102(a)(2) as being anticipated by Oda et al. (WO 2020/189236 A1—machine translation relied upon) (hereafter “Oda”) set forth in the last Office action. The rejections have been withdrawn. However, as outlined below, new grounds of rejection have been made.
The amendment to claim 1 has overcome the rejections of claims 1, 6, and 8-9 under 35 U.S.C. 102(a)(2) as being anticipated by Tatsumi et al. (WO 2020/189283 A1—machine translation relied upon) (hereafter “Tatsumi”) set forth in the last Office action. The rejections have been withdrawn. However, as outlined below, new grounds of rejection have been made.
The amendment to claim 1 has overcome the rejections of claims 1-2, 6, 8, and 11 under 35 U.S.C. 102(a)(1) and 35 U.S.C. 102(a)(2) as being anticipated by Cheng et al. (WO 2019/191665 A1) (hereafter “Cheng”) set forth in the last Office action; the rejection of claim 14 under 35 U.S.C. 103 as being unpatentable over Cheng et al. (WO 2019/191665 A1) (hereafter “Cheng”) set forth in the last Office action; the rejections of claims 12 and 15 under 35 U.S.C. 103 as being unpatentable over Cheng et al. (WO 2019/191665 A1) (hereafter “Cheng”), and further in view of Seo et al. (US 2002/0121860 A1) (hereafter “Seo”) set forth in the last Office action. The rejections have been withdrawn. However, as outlined below, new grounds of rejection have been made.
The amendment to claim 1 has overcome the rejections of claims 1, 6-8, 14, and 16-17 are rejected under 35 U.S.C. 103 as being unpatentable over Oshiyama et al. (WO 2015/022835 A1—machine translation relied upon) (hereafter “Oshiyama”) set forth in the last Office action. The rejections have been withdrawn. However, as outlined below, new grounds of rejection have been made.
Response to Arguments
Applicant’s arguments with respect to the rejections of claims 1-2, 6, and 8 under 35 U.S.C. 102(a)(2) as being anticipated by Sugawara et al. (WO 2020/059520 A1—US 2021/0340160 A1) (hereafter “Sugawara”) set forth in the last Office action have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant’s arguments with respect to the rejections of claims 1-2, 6, and 8 under 35 U.S.C. 102(a)(2) as being anticipated by Oda et al. (WO 2020/189236 A1—machine translation relied upon) (hereafter “Oda”) set forth in the last Office action have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant’s arguments with respect to the rejections of claims 1, 6, and 8-9 under 35 U.S.C. 102(a)(2) as being anticipated by Tatsumi et al. (WO 2020/189283 A1—machine translation relied upon) (hereafter “Tatsumi”) set forth in the last Office action have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant’s arguments with respect to the rejections of claims 1-2, 6, 8, and 11 under 35 U.S.C. 102(a)(1) and 35 U.S.C. 102(a)(2) as being anticipated by Cheng et al. (WO 2019/191665 A1) (hereafter “Cheng”) set forth in the last Office action; the rejection of claim 14 under 35 U.S.C. 103 as being unpatentable over Cheng et al. (WO 2019/191665 A1) (hereafter “Cheng”) set forth in the last Office action; the rejections of claims 12 and 15 under 35 U.S.C. 103 as being unpatentable over Cheng et al. (WO 2019/191665 A1) (hereafter “Cheng”), and further in view of Seo et al. (US 2002/0121860 A1) (hereafter “Seo”) set forth in the last Office action have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant’s arguments with respect to the rejections of claims 1, 6-8, 14, and 16-17 are rejected under 35 U.S.C. 103 as being unpatentable over Oshiyama et al. (WO 2015/022835 A1—machine translation relied upon) (hereafter “Oshiyama”) set forth in the last Office action have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
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.
Claim(s) 1-2, 6-9, 11, 14, and 16-17 are rejected under 35 U.S.C. 103 as being unpatentable over Seo et al. (US 2020/0207760 A1) (hereafter “Seo”).
Regarding claims 1-2, 6-8, 11, and 14: Seo discloses the compound shown below {p. 7}.
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Seo does not disclose a compound similar to the compound shown above except for having four or five chirality generation sites.
However, Seo teaches that the compound shown above has the structure of Formula 2 of Seo, having the structure shown below {paragraph [0045]}.
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Where R15 to R18 can be substituted or unsubstituted heteroaryl groups {paragraph [0046]}, which is demonstrated in the compound shown above by the substituted carbazolyl groups and unsubstituted carbazolyl groups. Thus, the substituted carbazolyl groups and unsubstituted carbazolyl groups shown in the compound above are known alternatives.
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 Seo shown above by substituting carbazolyl substituted carbazolyl groups in place of the unsubstituted carbazolyl groups, based on the teaching of Seo. 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 selection of carbazolyl substituted carbazolyl groups would have been a choice from a finite number of identified, predictable solutions (the exemplified groups substituents of Seo), with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of substituent and substituent positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Seo does not disclose a specific device or a specific functional layer comprising the compound shown above.
However, Seo teaches that the compound shown above can be used as the host material of a light-emitting layer of an organic light emitting device {paragraphs [0043], [0049], [0070], [0090], and [0106]}. The host can be present at a concentration of greater than 50% {paragraphs [0111] and [0124]}.
Seo teaches that the light emitting device comprises a first electrode that is an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a second electrode that is a cathode {paragraphs [0074]-[0084]}.
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 Seo shown above, such that it was used as the host material of the light-emitting layer of the organic light emitting device of Seo described above at a concentration of greater than 50% within the light emitting layer, based on the teaching of Seo. The modification would have been a combination of prior art elements according to known methods to yield predictable results. See MPEP 2143(I)(A). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of materials to be used to make an organic light-emitting device in order to produce optimal organic light-emitting devices.
The molecular weight of the above compound is 1409 g/mol, and the compound has 4 chirality generating sites (the four N atoms linked to the central heterocyclic ring).
One substituent that can be equated with the instant R2 is also consistent with the definition of the instant R1. The other two positions associated with the instant R2 are each hydrogen or N, which is permitted by the current claim 1.
Seo teaches the claimed invention above but fails to teach that for the aromatic compound, a film density value calculated by molecular dynamic calculations of NPT ensemble at 300 K is defined as an initial film density of the functional film comprising only the aromatic compound, and for the aromatic compound, when a film density value calculated by molecular dynamics calculation at 370 K is defined as a film density value after storage of the functional film at the temperature, the difference between the initial film density and the film density value after storage is 1% or less with respect to the initial film density. It is reasonable to presume that a film density value calculated by molecular dynamic calculations of NPT ensemble at 300 K is defined as an initial film density of the functional film comprising only the aromatic compound, and for the aromatic compound, when a film density value calculated by molecular dynamics calculation at 370 K is defined as a film density value after storage of the functional film at the temperature, the difference between the initial film density and the film density value after storage is 1% or less with respect to the initial film density is inherent to Seo. Support for said presumption is found in the use of like materials and like processes which would result in the claimed property.
The compound of Seo shown above has significant structural similarities with the instant compounds Exemplified compound 8 and Exemplified compound 21. The compounds are similar in that Exemplified compound 8 comprises a central pyridine ring and Exemplified compound 21 comprises carbazolyl substituted carbazole groups surrounding a central ring. The differences lie in the combination of central ring and surrounding substituent as well as the presence of the acridinyl group. However, the acridinyl ring in encompassed by the general description of a condensed aromatic ring containing not less than 14 pi electrons. Paragraph [0097] of the instant specification describe both benzene and pyridine as options for the central ring of the compounds of the instant general formula (2). Paragraph [0088] of the instant specification describe that the aromatic heterocyclic group containing not less than 14 pi-electrons can be substituted or unsubstituted and does not limit the possible substituents. Additionally, the compound meets the limitations of the current claim 1 and the description in the specification in paragraphs [0074] to [0077] of the instant specification. Given the structural similarities to example compounds as well as meeting the conditions described in the current claim 1 and paragraphs [0074] to [0077] of the instant specification, the compound of Seo shown above would have the required properties of the current claim 1.
The burden is upon the Applicant to prove otherwise. In re Fitzgerald 205 USPQ 594. In addition, the presently claimed properties would obviously have been present once the Seo product is provided. Note In re Best, 195 USPQ at 433, footnote 4 (CCPA 1977).
Seo teaches the claimed invention above but fails to teach that for the functional film comprising the aromatic compound of Seo shown above the initial film density value is in the range of 1.00 to 1.20 g/cm3. It is reasonable to presume that for the functional film comprising the aromatic compound of Seo shown above the initial film density value being in the range of 1.00 to 1.20 g/cm3 is inherent to Seo. Support for said presumption is found in the use of like materials and like processes which would result in the claimed property.
The compound of Seo shown above has significant structural similarities with the instant compounds Exemplified compound 8 and Exemplified compound 21. The compounds are similar in that Exemplified compound 8 comprises a central pyridine ring and Exemplified compound 21 comprises carbazolyl substituted carbazole groups surrounding a central ring. The differences lie in the combination of central ring and surrounding substituent as well as the presence of the acridinyl group. However, the acridinyl ring in encompassed by the general description of a condensed aromatic ring containing not less than 14 pi electrons. Paragraph [0097] of the instant specification describe both benzene and pyridine as options for the central ring of the compounds of the instant general formula (2). Paragraph [0088] of the instant specification describe that the aromatic heterocyclic group containing not less than 14 pi-electrons can be substituted or unsubstituted and does not limit the possible substituents. Additionally, the compound meets the limitations of the current claim 1 and the description in the specification in paragraphs [0074] to [0077] of the instant specification. Table IV of the instant specification shows that a film comprising the instant Example Compound 8 has an initial film density in the range of 1.00 to 1.20 g/cm3. Given the structural similarities to example compounds as well as meeting the conditions described in the current claim 1 and paragraphs [0074] to [0077] of the instant specification, the compound of Seo shown above would have an initial film density value being in the range of 1.00 to 1.20 g/cm3.
The burden is upon the Applicant to prove otherwise. In re Fitzgerald 205 USPQ 594. In addition, the presently claimed properties would obviously have been present once the Seo product is provided. Note In re Best, 195 USPQ at 433, footnote 4 (CCPA 1977).
Regarding claim 7: Seo teaches all of the features with respect to claim 1, as outlined above.
The carbazolyl substituted carbazole groups are condensed aromatic heterocyclic groups containing not less than 14 pi electrons and comprise 2 nitrogen atoms (one in each carbazolyl group).
Regarding claims 9 and 16-17: Seo teaches all of the features with respect to claim 1, as outlined above.
Seo does not teach a specific compound having the features of the current claim 1 that also has two substituents that can be equated with the instant R2 that represent the instant R1.
However, Seo teaches that the compound shown above has the structure of Formula 2 of Seo, having the structure shown below {paragraph [0045]}.
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Where R15 to R18 can be substituted or unsubstituted heteroaryl groups {paragraph [0046]}, which is demonstrated in the compound shown above by the carbazolyl substituted carbazolyl groups.
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 Seo shown above by substituting a carbazolyl substituted carbazolyl group in place of the hydrogen on the central pyridine, based on the teaching of Seo. 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 selection of carbazolyl substituted carbazolyl would have been a choice from a finite number of identified, predictable solutions (the exemplified groups substituents of Seo), with a reasonable expectation of success. See MPEP 2143(I)(E). Furthermore, one of ordinary skill in the art would have been motivated to select suitable and optimum combinations of substituent and substituent positions to be used to make compounds for use in an organic light-emitting device in order to produce optimal organic light emitting devices.
Claim(s) 12 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Seo et al. (US 2020/0207760 A1) (hereafter “Seo”) as applied to claims 1 and 14 above, and further in view of Seo et al. (US 2002/0121860 A1) (hereafter “Seo ‘860”).
Regarding claims 12 and 15: Seo teaches all of the features with respect to claims 1 and 14, as outlined above.
Seo does not teach that at least two adjacent layer among the plurality of layers are each the functional film or that the functional film is a charge transport layer.
However, as outlined above, the device of Seo comprises a hole transport layer between the first electrode than is an anode and the light emitting layer as well as an electron transport layer between the light emitting layer and the second electrode that is a cathode.
Seo ‘860 teaches an organic light-emitting device having the structure of a light-emitting layer comprising a host and a dopant, an electron transport layer between the light-emitting layer and the cathode, a mixed layer between the light-emitting layer and the electron transport layer comprising a mixture of the host material and the electron transport materials, a hole transport layer between the light-emitting layer and the anode, and a mixed layer between the light-emitting layer and the hole transport layer comprising a mixture of the host material and the hole transport material {Fig. 22 as described in paragraph [0069]}.
Seo ‘860 teaches that introducing mixed layers between the light-emitting layer and the hole-transport layer as well as between the light-emitting layer and the electron-transport layer lowers energy barriers between organic layers, lowering driving voltage and increase device lifetime {paragraph [0028] and paragraphs [0049]-[0051], [0054] describing Figs. 1A to 1D}.
At the time of the invention, it would have been obvious to one of ordinary skill in the art to have further modified the organic electroluminescence device taught by Seo by including a mixed layer comprising the host material of the light emitting layer (the compound of Seo shown above) and the electron transport material between the light-emitting layer and the electron transporting layer as well as a mixed layer comprising the host material of the light emitting layer (the compound of Seo shown above) and the hole transport layer, based on the teachings of Seo. The motivation for doing so would have been to lower energy barriers between sub-layers of each organic layer, lowering driving voltage, and increasing device lifetime, as taught by Seo ‘860.
The mixed layer between the light-emitting layer and the hole transport layer as well as the mixed layer between the light-emitting layer and the electron transport layer can each be equated with a functional film of the current claim 1 comprising the claimed aromatic compound. Thus, the resultant device would comprise three adjacent layer that can each be equated with the claimed functional film. Additionally, each mixed layer can be equated with a charge transport layer, because they would necessarily transport charges to the light-emitting layer.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DYLAN CLAY KERSHNER whose telephone number is (303)297-4257. The examiner can normally be reached M-F, 9am-5pm (Mountain).
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/DYLAN C KERSHNER/ Primary Examiner, Art Unit 1786