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 .
Response to Amendment
In the response filed August 3, 2026, the claims were amended.
These amendments are hereby entered.
Claims 1-17 were originally filed.
Claims 18-22 have been added.
Claims 3, 5, 15, 16, and 20 are instantly amended.
Claims 1-22 are pending in the application.
Response to Arguments
Applicant's arguments have been fully considered but they are not persuasive.
With respect to Applicant’s argument that Kim and Kido place their metal-doped layer or electron-injection layer adjacent to the cathode and not between two emission layers, Examiner disagrees.
The paragraph of Kim cited by applicant, [0133], merely states one application of the compound of Formula I. An electron injection layer is neither a more-preferred nor a required device layer for the compound of Formula I. This is evidenced by the fact that every experimental example of Kim places the compound of Formula I in an electron transport layer. Clearly the compound is not required to be directly in physical contact with a cathode.
Likewise, while Kido teaches an interfacial layer comprising a metal dopant, Kido only teaches a single layer between the cathode and the emission layer which acts as an electron transport and injection layer. Kido states that the purpose of the compound is to decrease the energy barrier between the cathode and luminescent layer (abstract). Clearly an electron injection layer is not a required device layer and it would be beneficial to dope any device layer through which electrons travel.
As Hatwar teaches a tandem electroluminescent device comprising an electron transport layer between two light emitting layers, and as electrons must travel through the electron transport layer of the device of Hatwar, an electron transport layer comprising a compound of instant formula (I) and a metal dopant which is present between two emission layers would have been an obvious combination to the ordinary skilled artisan prior to the effective filing date of the claimed invention.
With respect to Applicant’s argument that Hatwar teaches away from a metal-dopant in the electron transport layer, Examiner disagrees.
The layer comprising a “pure-organic” n-dopant is the electron injection layer (paragraph 0095). Hatwar actually suggests the use of an n-dopant in the electron transport layer in order to lower the energy barrier of the layer (resistivity, paragraph 0094).
With respect to Applicant’s argument that arriving at the claimed compound from Kim’s compound 38 requires independently selecting multiple substituents from Kim’s separate genera without any teaching, suggestion, or motivation, Examiner disagrees.
It is Examiner’s position that Kim not only teaches the selections pointed out by Examiner but that they are preferred selections to make. Paragraph [0045] of Kim gives just two preferred selections for variable L. Similarly, paragraph [0046] sets forth just nine preferred definitions for variable R1. Clearly a pyridinyl group which is further substituted by one or more pyridinyl groups is within the scope of the prior art and a preferred combination of selections.
MPEP section 2141 teaches that a prima facie case of obviousness is present when a finite number of identified predictable solutions are present. Therefore, a substituted pyridinyl group may be chosen from two possible definitions and two additional pyridinyl substitutions may be chosen from nine possible definitions, the extremely narrow scope of these definitions leads to a prima facie case of obviousness when the moiety of Kim comprising (L)n-R1 is a terpyridyl group.
For at least these reasons, the rejection of record is respectfully maintained.
Although some claims have been amended for scope, Applicant’s amendments do not overcome the prior art because the prior art still reads on the claimed invention.
A reinterpretation of the prior art is given below to explain how the prior art still reads on the amended claims.
Claim Rejections - 35 USC § 102
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.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 22 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yabe et al. (JP 2005/243266 A, using the provided translation for references).
With respect to claim 22, Yabe discloses the compound below (paragraph 0041).
PNG
media_image1.png
290
316
media_image1.png
Greyscale
This compound meets the requirements of instant formula (I) when Ar1 and Ar2 are both a C6 aryl (phenyl), L is a single bond, Ar3 is a substituted pyrazinylene, Ar4 is a substituted C5 heteroaryl (pyridine), and n is 1, wherein the substituents are all a C6 aryl.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-15 and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2015/0034915 A1), and Kido et al. (U.S. Pat. No. 6,013,384), and further in view of Hatwar et al. (US 2010/0288362 A1).
With respect to claim 1, Kim discloses an organic electronic device (an organic light-emitting device, paragraph 0077 and Figure 1) comprising an anode, a cathode, and at least one organic semiconductor layer (electron transport layer) (paragraph 0006 and Figure 1) and the electron transport layer comprises a compound of Formula (I) (paragraph 0012) such as compound 38 (paragraph 0069), which is pictured below.
PNG
media_image2.png
202
270
media_image2.png
Greyscale
Compound 38 is derived from Formula 1 of Kim (paragraph 0027), which is pictured below.
PNG
media_image3.png
210
292
media_image3.png
Greyscale
PNG
media_image4.png
128
318
media_image4.png
Greyscale
Kim also teaches that p is 2 (paragraph 0044), and Z1 is heteroaryl (paragraph 0044), such as pyridinyl (paragraph 0065, line 9).
This modification produces a compound that meets the requirements of instant formula (1) when at least one of Ar1 and Ar2 comprises a C5 heteroaryl, L is a single bond, Ar3 is a dibenzoacridine, and n is 0 so that Ar4 is not present.
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a material that has excellent electric characteristics, a high charge transporting capability, a high light-emitting capability, a high glass transition temperature, and a crystallization-preventing capability, and that is suitable for use as an electron transporting material for a full color, such as red, green, blue, or white, or fluorescent and phosphorescent devices, and an organic light-emitting device that has high efficiency, low driving voltage, high brightness, long lifespan, due to the inclusion of the material (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Kim does not teach nor fairly suggest that the electron transport layer further comprises a metal dopant.
Kido teaches an analogous EL device wherein an organic layer adjacent to the cathode, such as an electron transport layer, is doped with a metal dopant capable of acting as a donor dopant, which lowers the driving voltage of the device (abstract).
Kido teaches examples of the donor dopant include alkali metals (Col. 2, lines 55-57), such as lithium (Col. 4, line 15).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate an alkali metal dopant, such as lithium, into the layer adjacent to the cathode (an electron transporting layer) in the device of Kim in order to lower the driving voltage of the device, as taught by Kido.
However, neither Kim nor Kido teach nor fairly suggest that the electron transport layer is found between a first emission layer and a second emission layer, wherein the layer between the first and second emission layers also includes an n-type charge generation layer.
In analogous art, Hatwar teaches a tandem organic electronic device comprising at least two organic phototransducing units (emission layers) which are separated by an intermediate connecting region (a charge generation layer, paragraph 0002).
Hatwar teaches the structure of a tandem OLED comprising a green, red, and blue light emitting region in Figure 3, which is pictured below, and which has been annotated using the definitions in paragraph [0100] to facilitate discussion.
PNG
media_image5.png
686
772
media_image5.png
Greyscale
This meets the requirements of the instant claim as it comprises a first and second emission layer as part of a stack, each stack comprising a hole transport layer, an emitting layer, and an electron transport layer, and the stacks are further separated by a charge generation layer (intermediate connecting region, 340, Figure 3).
Hatwar teaches that embodiments of the invention can provide organic EL devices that have good luminance efficiency, good operational stability, and reduced drive voltages (paragraph 0131).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the electron transport layer composition taught by Kim and Kido as one or more electron transport layers in the tandem device of Hatwar in order to provide an EL device that has good luminance efficiency, good operational stability, and reduced drive voltage, as taught by Hatwar.
With respect to claim 2, Kim, Kido, and Hatwar teach the device of claim 1, as discussed above.
Compound 38 is derived from Formula 1 of Kim (paragraph 0027), which is pictured below.
PNG
media_image3.png
210
292
media_image3.png
Greyscale
Kim also teaches that n is 1 (paragraph 0031), and L is an unsubstituted C6 arylene (paragraph 0030).
This modification produces a compound that meets the requirements of the instant claim when L is an unsubstituted phenylene.
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a material that has excellent electric characteristics, a high charge transporting capability, a high light-emitting capability, a high glass transition temperature, and a crystallization-preventing capability, and that is suitable for use as an electron transporting material for a full color, such as red, green, blue, or white, or fluorescent and phosphorescent devices, and an organic light-emitting device that has high efficiency, low driving voltage, high brightness, long lifespan, due to the inclusion of the material (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 3, Kim, Kido, and Hatwar teach the device of claim 1, and n is 0 so Ar4 is not present, as discussed above.
With respect to claim 4, Kim, Kido, and Hatwar teach the device of claim 1, and Ar1 and Ar2 are pyridyl, as discussed above.
With respect to claim 5, Kim, Kido, and Hatwar teach the device of claim 1, and L is a single bond, as discussed above.
With respect to claim 6, Kim, Kido, and Hatwar teach the device of claim 1, and Ar3 is dibenzoacridine, as discussed above.
With respect to claim 7, Kim, Kido, and Hatwar teach the device of claim 1, and Ar4 is not present, as discussed above.
With respect to claim 8, Kim, Kido, and Hatwar teach the device of claim 1 and the metal dopant is lithium, as discussed above.
With respect to claim 9, Kim, Kido, and Hatwar teach the device of claim 1, as discussed above.
Compound 38 is derived from Formula 1 of Kim (paragraph 0027), which is pictured below.
PNG
media_image3.png
210
292
media_image3.png
Greyscale
Kim also teaches that n is 1 (paragraph 0031), and L is an unsubstituted C6 arylene (paragraph 0030).
This modification produces a compound that meets the requirements of the instant claim when L is an unsubstituted phenylene, such as instant B1, B2, or B3.
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a material that has excellent electric characteristics, a high charge transporting capability, a high light-emitting capability, a high glass transition temperature, and a crystallization-preventing capability, and that is suitable for use as an electron transporting material for a full color, such as red, green, blue, or white, or fluorescent and phosphorescent devices, and an organic light-emitting device that has high efficiency, low driving voltage, high brightness, long lifespan, due to the inclusion of the material (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claims 10, 18, and 19, Kim, Kido, and Hatwar teach the device of claim 1, as discussed above.
Examiner is interpreting lithium to meet the requirements of the instant claim through its use as a preferred embodiment of the claimed metal dopant, as given on page 45 of the instant specification. Products of identical chemical composition cannot have mutually exclusive properties, and it has been held that when the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present (See MPEP 2112.01(II)), and the alkali metal dopant of Kido reads on the claims.
Kido is silent to the electronegativity of the metal dopant according to the Pauling scale. However, this is considered to be a property of the composition. Support for this presumption comes from the use of like materials and like processes when lithium is used as a dopant in the electron transport layer of an electroluminescent device, which would result in the claimed property described in the instant claims. Therefore, the claims are considered to be obvious over Kim, Kido, and Hatwar, and the burden shifts to applicant to show that there is an unobvious difference between the claimed composition and the composition in the prior art. See MPEP 2112 (V). In addition, the presently claimed properties are considered to be present once the work of Kido was first provided. See MPEP 2112.01 (II).
With respect to claim 11, Kim, Kido, and Hatwar teach the device of claim 1 and Ar3 is a dibenzoacridine, as discussed above, which is instant E1.
With respect to claim 12, Kim, Kido, and Hatwar teach the device of claim 1, and Ar4 is not present, as discussed above.
With respect to claim 13, Kim, Kido, and Hatwar teach the device of claim 1, as discussed above.
Compound 38 is derived from Formula 1 of Kim (paragraph 0027), which is pictured below.
PNG
media_image3.png
210
292
media_image3.png
Greyscale
Kim also teaches that n is 1 (paragraph 0031), and L is an unsubstituted C6 arylene (paragraph 0030).
This modification produces a compound that meets the requirements of the instant claim when L is an unsubstituted phenylene, such as instant G1 or G2.
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a material that has excellent electric characteristics, a high charge transporting capability, a high light-emitting capability, a high glass transition temperature, and a crystallization-preventing capability, and that is suitable for use as an electron transporting material for a full color, such as red, green, blue, or white, or fluorescent and phosphorescent devices, and an organic light-emitting device that has high efficiency, low driving voltage, high brightness, long lifespan, due to the inclusion of the material (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 14, Kim, Kido, and Hatwar teach the device of claim 1, and the organic electronic device further comprises at least one emission layer (paragraph 0071) and the electron transport layer is between the emission layer and the cathode (paragraph 0006).
With respect to claims 15 and 20, Kim, Kido, and Hatwar teach the device of claim 1, and the electronic device is an organic light emitting device, as discussed above.
Claims 16, 17, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2015/0034915 A1).
With respect to claim 16, Kim discloses compound 38 (paragraph 0069), which is pictured below.
PNG
media_image2.png
202
270
media_image2.png
Greyscale
Compound 38 is derived from Formula 1 of Kim (paragraph 0027), which is pictured below, when R1 is represented by formula 3b (paragraph 0046), which is also pictured below.
PNG
media_image3.png
210
292
media_image3.png
Greyscale
PNG
media_image4.png
128
318
media_image4.png
Greyscale
Kim also teaches that p is 2 (paragraph 0044), and Z1 is heteroaryl (paragraph 0044), such as pyridinyl (paragraph 0065, line 9).
This modification produces a compound that meets the requirements of instant formula (1) wherein Ar1 and Ar2 are a pyridyl group, L is a single bond, Ar3 is a dibenzoacridine, and n is 0 so that Ar4 is not present.
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a material that has excellent electric characteristics, a high charge transporting capability, a high light-emitting capability, a high glass transition temperature, and a crystallization-preventing capability, and that is suitable for use as an electron transporting material for a full color, such as red, green, blue, or white, or fluorescent and phosphorescent devices, and an organic light-emitting device that has high efficiency, low driving voltage, high brightness, long lifespan, due to the inclusion of the material (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 17, Kim teaches the compound of claim 16, as discussed above.
Compound 38 is derived from Formula 1 of Kim (paragraph 0027), which is pictured below.
PNG
media_image3.png
210
292
media_image3.png
Greyscale
Kim also teaches that n is 1 (paragraph 0031), and L is an unsubstituted C6 arylene (paragraph 0030).
This modification produces a compound that meets the requirements of instant claim 17 when L is an unsubstituted phenylene.
Kim includes each element claimed, with the only difference between the claimed invention and Kim being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a material that has excellent electric characteristics, a high charge transporting capability, a high light-emitting capability, a high glass transition temperature, and a crystallization-preventing capability, and that is suitable for use as an electron transporting material for a full color, such as red, green, blue, or white, or fluorescent and phosphorescent devices, and an organic light-emitting device that has high efficiency, low driving voltage, high brightness, long lifespan, due to the inclusion of the material (paragraph 0010), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 21, Kim teaches the compound of claim 16 and Ar4 is not present, as discussed above.
Conclusion
Applicant's amendment necessitated any 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 RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached at 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/RACHEL SIMBANA/Primary Examiner, Art Unit 1786
