DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 07/25/2023 and 07/25/2023 were filed after the mailing date of the instant application on 06/02/2023. The submissions are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Response to Amendment
In the preliminary amendment, the claims and specification were amended.
These amendments are hereby entered.
Claims 1-20 were originally filed.
Claims 21-39 have been added.
Claims 1-19 are canceled.
Claims 20-39 are pending in the instant application.
Claim Objections
Claims 20, 23, and 36 are objected to because of the following informalities:
Claim 20 is objected to under 37 CFR 1.75(c) as being in improper form because it does not refer to a preceding claim. See MPEP 608.01(n).
Claim 20 is objected to under 37 CFR 1.121(c)(2) for failing to identify all changes using proper claim status identifiers and mark-up indications because claim 20 is originally filed but has been indicated as (New).
With respect to claim 23, the claim refers to the combination of R1 and R2. The word “is” should be “are”.
With respect to claim 36, the claim contains the limitation that the organic layer further comprises a co-host compound. While calling a compound a co-host is easily understood by the ordinary skilled artisan and does not introduce uncertainty, it implies another co-host is also present, but no other co-host is mentioned. It is unclear if this is intentional or accidental.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 20, 28, and 31 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
With respect to claim 20, the claim is incomplete because it refers to a canceled claim (claim 1).
In continuing examination, claim 20 is being interpreted as a claim that is dependent from and drawn to the compound of claim 21.
With respect to claim 28, the syntax of the claim is unclear. The claim contains the limitation, “--each of which is optionally substituted with a group RCZ selected from the polycyclic group selected from the group consisting of Formula A, Formula B, or Formula C—".
It is unclear which group the substituents of RCZ are chosen from.
In continuing examination, this is being interpreted as “--each of which is optionally substituted with a group RCZ selected from [[the polycyclic group selected from]] the group consisting of Formula A, Formula B, or Formula C—".
With respect to claim 31, the claim contains the limitation that “the organic linker is carbazole”. This is confusing for at least two reasons. The first reason is that an organic linker is not required by parent claim 21, and so it is unclear if an organic linker is actually required by the claim. The second reason is that more than one variable in parent claim 21 contain “organic linker” in their respective Markush group (RN and RC through RH all include this option). Thus, it is unclear whether applicant is requiring that all, some, or none of these groups actually comprise an organic linker.
In continuing examination, this limitation is being interpreted as “when present, the organic linker is a carbazole”.
Claim Rejections - 35 USC § 103
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 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 20-21, 24-26, 29-32, and 34-39 are rejected under 35 U.S.C. 103 as being unpatentable over Oshiyama et al. (JP 2013/093431 A, using the provided translation for references).
With respect to claims 21, 25, and 29-30, Oshiyama discloses compound 70 (paragraph 0061), which is pictured below.
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This compound is derived from Oshiyama general formula (1) (paragraph 0032), which is pictured below.
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In general formula (1), Oshiyama also teaches that X2 is NR0 (paragraph 0032), and R0 is a C6 aryl (phenyl) group (see for example compound 139, 140, or 141 in paragraph 0068).
Such a modification produces a compound that meets the requirements of instant Formula I when X1-X8 are CH, R1 is represented by Formula C, and R2 is a hydrogen atom. In Formula C, RN is a aryl (phenyl) group, all X characters are carbon atoms, Y is an oxygen atom, the RH of X30 represents a bond to R1, and the RG of X27 represents the combination of heteroaryl and aryl groups.
Oshiyama includes each element claimed, with the only difference between the claimed invention and Oshiyama being a lack of the aforementioned combination including a nitrogen atom 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 the finite list 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 compound with excellent charge transport capability and charge tolerance (paragraph 0036), which results in high luminous efficiency, high durability, low operating voltage, and minimal voltage rise when used in an organic light emitting device (paragraph 0034), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 24, Oshiyama teaches the compound of claim 21, as discussed above.
Oshiyama also teaches that each of A1 through A8 are C-Ra, each of X1 and X2 may be NR0, and when Ra or R0 are a substituent, they may have synonymous definitions (paragraph 0038).
In this respect, Oshiyama teaches that the ortho-biphenyl group could be located on the nitrogen atom of X2 and forms a compound wherein RN is a direct bond to R1.
Oshiyama includes each element claimed, with the only difference between the claimed invention and Oshiyama being a lack of the aforementioned nitrogen substituent 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 the finite list 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 compound with excellent charge transport capability and charge tolerance (paragraph 0036), which results in high luminous efficiency, high durability, low operating voltage, and minimal voltage rise when used in an organic light emitting device (paragraph 0034), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 26, Oshiyama teaches the compound of claim 21, and the compound of claim 21 also meets the requirements of the instant claim when X27 is CRG, and RG is connected to R1 through two C5 arylene groups with a nitrogen atom (pyridine) and one C12 arylene with a carbon and oxygen atom, as discussed above.
With respect to claim 31, Oshiyama teaches the compound of claim 21, and an organic linker is not present.
With respect to claim 32, Oshiyama teaches the compound of claim 21, as discussed above.
Oshiyama gives several examples of compounds wherein the moiety of Formula 1 is bonded to a pyridine group and a benzene group (see for example compounds 8, 47, and 48).
It would have been within the technical grasp of a person of ordinary skill in the art, to envisage obvious variants of the compound of Oshiyama, and incorporate a nitrogen atom into one of X1 through X4, and arrive at the compound of the instant claim, with a reasonable expectation of achieving a compound with excellent charge transport capability and charge tolerance (paragraph 0036), which results in high luminous efficiency, high durability, low operating voltage, and minimal voltage rise when used in an organic light emitting device (paragraph 0034), as taught by Oshiyama.
With respect to claim 34, Oshiyama discloses an organic El element comprising an anode and a cathode and an organic layer and the organic layer comprises a compound of general formula (1) (paragraph 0080), such as compound 70 (page 19 of the original document), which is pictured below.
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This compound is derived from Oshiyama general formula (1) (paragraph 0032), which is pictured below.
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In general formula (1), Oshiyama also teaches that X2 is NR0 (paragraph 0032), and R0 is a C6 aryl (phenyl) group (see for example compound 139, 140, or 141 in paragraph 0068).
Such a modification produces a compound that meets the requirements of instant Formula I when X1-X8 are CH, R1 is represented by Formula C, and R2 is a hydrogen atom. In Formula C, RN is a aryl (phenyl) group, all X characters are carbon atoms, Y is an oxygen atom, the RH of X30 represents a bond to R1, and the RG of X27 represents the combination of heteroaryl and aryl groups.
Oshiyama includes each element claimed, with the only difference between the claimed invention and Oshiyama being a lack of the aforementioned combination including a nitrogen atom 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 the finite list 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 compound with excellent charge transport capability and charge tolerance (paragraph 0036), which results in high luminous efficiency, high durability, low operating voltage, and minimal voltage rise when used in an organic light emitting device (paragraph 0034), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound of Oshiyama in an organic electroluminescent device, as taught by Oshiyama.
With respect to claim 35, Oshiyama teaches the OLED of claim 34, and Oshiyama also teaches that the organic layer also comprises a well-known phosphorescent dopant (paragraph 0097), such as Ir(ppy)3 (paragraph 0098), which is pictured below.
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This dopant meets the requirements of the second ligand on the second row of the instant claim when all Y characters are carbon atoms, and Ra and Rb represent no substitution.
With respect to claim 36, Oshiyama teaches the OLED of claim 34, and Oshiyama also teaches that host compounds such as OC-1 (paragraph 0075), which comprises a carbazole moiety, may be used in the device.
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With respect to claim 37, Oshiyama discloses a display device comprising an organic electroluminescent device (paragraph 0028), and the organic electroluminescent device comprises anode and a cathode and an organic layer and the organic layer comprises a compound of general formula (1) (paragraph 0080), such as compound 70 (page 19 of the original document), which is pictured below.
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This compound is derived from Oshiyama general formula (1) (paragraph 0032), which is pictured below.
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In general formula (1), Oshiyama also teaches that X2 is NR0 (paragraph 0032), and R0 is a C6 aryl (phenyl) group (see for example compound 139, 140, or 141 in paragraph 0068).
Such a modification produces a compound that meets the requirements of instant Formula I when X1-X8 are CH, R1 is represented by Formula C, and R2 is a hydrogen atom. In Formula C, RN is a aryl (phenyl) group, all X characters are carbon atoms, Y is an oxygen atom, the RH of X30 represents a bond to R1, and the RG of X27 represents the combination of heteroaryl and aryl groups.
Oshiyama includes each element claimed, with the only difference between the claimed invention and Oshiyama being a lack of the aforementioned combination including a nitrogen atom 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 the finite list 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 compound with excellent charge transport capability and charge tolerance (paragraph 0036), which results in high luminous efficiency, high durability, low operating voltage, and minimal voltage rise when used in an organic light emitting device (paragraph 0034), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound in an organic electroluminescent device, such as a display device, as taught by Oshiyama.
With respect to claim 38, Oshiyama teaches the consumer product of claim 37, and Oshiyama also teaches that the display device is preferably constructed on a substrate that can convey flexibility to the OLED device.
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 create a flexible display device, as taught by Oshiyama.
With respect to claim 39, Oshiyama teaches the compound of claim 21, and Oshiyama also teaches that the compound may form a thin film by spin-coating the compound from a solution comprising other compounds (paragraph 0170).
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 create a formulation comprising the compound in order to spin it into a thin film, as taught by Oshiyama.
With respect to claim 20, Oshiyama teaches the compound of claim 21, as discussed above.
Examiner points to example compounds such as compound 11 (paragraph 0055), which comprises a hydroxyl group, compound 45 (paragraph 0058), which comprises a ether group, and Compound 75 (paragraph 0062), which comprises a halogen atom. A person having ordinary skill in the art would recognize these functional groups lend themselves to polymerization.
In this respect, Oshiyama teaches use of compounds of general formula (1) as a monomer and use of a compound of general formula (1) as a monomer would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention.
Claim 22 is rejected under 35 U.S.C. 103 as being unpatentable over Oshiyama et al. (JP 2013/093431 A, using the provided translation for references) as applied above, and further in view of Li et al. (US 2002/0076576 A1).
With respect to claim 22, Oshiyama teaches the compound of claim 21, as discussed above.
However, Oshiyama does not teach that RA and RB are deuterium atoms.
In analogous art, Li teaches compounds for use in an organic light emitting device (abstract)
Li teaches organic semiconductors consisting of a chromophore in which one or more hydrogen atoms is replaced with a deuterium atom. Li teaches that a deuterated organic semiconductor has improved performance, for instance, higher fluorescence yield and more stability than its non-deuterated analogue (paragraph 0023).
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 one or more deuterium atoms into the compound of Oshiyama in order to improve the compounds performance, and obtain higher fluorescence yield and more stability than its non-deuterated analogue, as taught by Li.
Claims 23, 28, and 33 are rejected under 35 U.S.C. 103 as being unpatentable over Oshiyama et al. (JP 2013/093431 A, using the provided translation for references) as applied above, and further in view of Song et al. (KR 2014/0145452 A, using the provided translation for references).
With respect to claim 23, Oshiyama teaches the compound of claim 21, as discussed above.
Oshiyama also teaches the compound may have the structure of compound 68 (paragraph 0061), which is pictured below.
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This compound is also derived from Oshiyama general formula (1), wherein Oshiyama also teaches that X2 is NR0 (paragraph 0032) and R0 is a C6 aryl (phenyl) group (see for example compound 139, 140, or 141 in paragraph 0068), as discussed above.
However, Oshiyama does not teach nor fairly suggest an ortho-biphenylene bonding pattern.
In analogous art, Song teaches a host compound with high triplet energy which facilitates energy transfer in the emissive layer, thereby improving luminous efficiency of blue light (Effects of the invention, page 3).
Song teaches the compound has a structure of Chemical Formula 1, wherein A and B are symmetrically substituted at the ortho positions of the biphenyl structure and each of A and B represent a heterocyclic moiety (Solution to the Challenge, page 2).
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Song teaches that by using an ortho-bonding pattern in the compound, the triplet energy is greatly increased (Table 1 on page 8), and that a device comprising the ortho-bonded host compound demonstrates improved luminous efficiency and luminance (Table 2 and page 9).
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 symmetric ortho-bonded biphenylene moiety in the compound of Oshiyama in order to obtain a host compound with increased triplet energy level, which can efficiently transfer energy from host to dopant, resulting in improved luminous efficiency and luminance, as taught by Song.
Such a modification produces a compound that meets the requirements of the instant claim when R1 and R2 are represented by Formula C.
With respect to claim 28, Oshiyama teaches the compound of claim 1, as discussed above.
Oshiyama also teaches compound 82 (paragraph 0062), which is pictured below.
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However, Oshiyama does not teach nor fairly suggest that the compound comprises a moiety Formula I wherein one of R1 or R2 is a carbazole or aza-analog thereof.
In analogous art, Song teaches a host compound with high triplet energy which facilitates energy transfer in the emissive layer, thereby improving luminous efficiency of blue light (Effects of the invention, page 3).
Song teaches the compound has a structure of Chemical Formula 1, wherein A and B are symmetrically substituted at the ortho positions of the biphenyl structure and each of A and B represent a heterocyclic moiety (Solution to the Challenge, page 2).
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Song teaches that by using an ortho-bonding pattern in the compound, the triplet energy is greatly increased (Table 1 on page 8), and that a device comprising the ortho-bonded host compound demonstrates improved luminous efficiency and luminance (Table 2 and page 9).
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 symmetric ortho-bonded biphenylene moiety between heterocyclic moieties in the compound of Oshiyama in order to obtain a host compound with increased triplet energy level, which can efficiently transfer energy from host to dopant, resulting in improved luminous efficiency and luminance, as taught by Song.
Such a modification produces a compound that meets the requirements of the instant claim wherein one of R1 or R2 is an unsubstituted carbazole.
With respect to claim 33, Oshiyama teaches the compound of claim 21, as discussed above.
Oshiyama also teaches compound 134 (paragraph 0068), which is pictured below.
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This compound is also derived from Oshiyama general formula (1) (paragraph 0032), as pictured and discussed above.
Oshiyama also teaches that each of A1 through A8 are C-Ra, and when X2 is NR0, and R0 is a substituent, it may have the same definitions as Ra (paragraph 0038) including combinations thereof (paragraph 0041).
In this respect, Oshiyama teaches that R0 is the combination of a biphenyl group and a 9-carbazolyl.
Such a modification produces the first compound on row four of page 7 of the instant claims.
Oshiyama includes each element claimed, with the only difference between the claimed invention and Oshiyama 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 the finite list 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 compound with excellent charge transport capability and charge tolerance (paragraph 0036), which results in high luminous efficiency, high durability, low operating voltage, and minimal voltage rise when used in an organic light emitting device (paragraph 0034), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
However, Oshiyama does not teach nor fairly suggest that the biphenylene linking group has a ortho bonding pattern.
In analogous art, Song teaches a host compound with high triplet energy which facilitates energy transfer in the emissive layer, thereby improving luminous efficiency of blue light (Effects of the invention, page 3).
Song teaches the compound has a structure of Chemical Formula 1, wherein A and B are symmetrically substituted at the ortho positions of the biphenyl structure and each of A and B represent a heterocyclic moiety (Solution to the Challenge, page 2).
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Song teaches that by using an ortho-bonding pattern in the compound, the triplet energy is greatly increased (Table 1 on page 8), and that a device comprising the ortho-bonded host compound demonstrates improved luminous efficiency and luminance (Table 2 and page 9).
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 symmetric ortho-bonded biphenylene moiety in the compound of Oshiyama in order to obtain a host compound with increased triplet energy level, which can efficiently transfer energy from host to dopant, resulting in improved luminous efficiency and luminance, as taught by Song.
Claim 27 is rejected under 35 U.S.C. 103 as being unpatentable over Oshiyama et al. (JP 2013/093431 A, using the provided translation for references) as applied above, and further in view of Tamao et al. (JP 2003/040867 A, using the provided translation for references).
With respect to claim 27, Oshiyama teaches the compound of claim 21, as pictured and discussed above.
Oshiyama also teaches that the compound may have the structure of compound 68 (paragraph 0061), which is pictured below.
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This compound is also derived from Oshiyama general formula (1), wherein Oshiyama also teaches that each of A1 through A8 are C-Ra, X2 may be NR0, and when Ra or R0 are a substituent, they are selected from the same group of definitions (paragraph 0038).
This forms a compound wherein the biphenylene linking group is connected between nitrogen atoms at X2.
However, Oshiyama does not teach nor fairly suggest a linking group of instant Formula I wherein two RA and/or two RB are joined to form one or more condensed rings.
In analogous art, Tamao teaches compounds useful as an organic EL fluorescent material which comprise an optically active 1,1’-binaphthylene-2,2’-diyl group (paragraph 0001).
Tamao teaches that the naphthalene group is easily reduced, and therefore, it is expected that when electrons are excited by light, the carbazole moieties at the 2,2’ positions become positively charged, and the naphthalene linking group becomes negatively charged, forming an intramolecular charge-separated complex which results in strong emission in the fluorescence spectrum (paragraph 0022).
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 a 1,1’-binaphthylene-2,2’-diyl linking group in the compound of Oshiyama in order to obtain a compound with an intramolecular charge-separated complex which results in strong emission in the fluorescence spectrum, as taught by Tamao.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Jung et al. (US 2017/0369439 A1) – claims relevant compounds.
Wolleb et al. (US 2015/0243907 A1) – teaches relevant compounds.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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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.
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/RACHEL SIMBANA/Primary Examiner, Art Unit 1786
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