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 .
Abstract
The abstract of the disclosure is objected to because it contains 177 words rather than 50 to 150 words. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
Claim Objections
Claims 20-29 and 31-38 are objected to because of the following informalities:
In claims 20-21, 28-29 and 31, it is recommended to replace “A1 and A2 together optional form a cycle with Z” with “A1 and A2 together optionally form a cycle with Z” for ease of reading.
In claims 20-21, 24-26, 31, and 33, it is recommended to replace “electron-withdrawing group” with “an electron-withdrawing group” for ease of reading.
In claims 20-21, given that electron-withdrawing groups include halogen, F, Cl, CN, perfluorinated alkyl, and perfluorinated aryl (see instant pg. 11), it is recommended to delete “halogen, F, Cl, CN, perfluorinated C1 to C8 alkyl, and perfluorinated C6 to C12 aryl” from the list of substituents to eliminate redundancy.
In claims 20-21, 31, and 33, it is recommended to replace “…or substituted or unsubstituted C2 to C24 heterocyclyl, ligand fragment Y, wherein” with “…substituted or unsubstituted C2 to C24 heterocyclyl, or a ligand fragment Y, wherein” or “…substituted or unsubstituted C2 to C24 heterocyclyl, or the at least one ligand fragment Y, wherein” for ease of reading.
In claims 20-21 and 28-29, it is recommended to replace “the coordinating linker X” with “the at least one coordinating linker X” for consistency and ease of reading.
In claims 22-27 and 34, it is recommended to replace “the ligand fragment Y” with “the at least one ligand fragment Y” for consistency and ease of reading.
In claim 22, given that a halogen group already includes F and Cl, it is recommended to delete “F” and “Cl” from the list of substituents to eliminate redundancy.
In claims 24-26, given that electron-withdrawing groups include F and perfluorinated alkyl (see instant pg. 11), it is recommended to delete “F” and “perfluorinated C1 to C24 alkyl” from the list of R’, R”, R”’ to eliminate redundancy.
In claims 28-29, and 32, it is recommended to replace “…substituted or unsubstituted C1 to C24 alkyl, ligand fragment Y,” with “…substituted or unsubstituted C1 to C24 alkyl, or a ligand fragment Y” or “…substituted or unsubstituted C1 to C24 alkyl, or the at least one ligand fragment Y” for ease of reading.
In claims 31 and 33, given that electron-withdrawing groups include halogen, F, Cl, CN, partially fluorinated or perfluorinated alkyl, partially fluorinated or perfluorinated aryl, or partially fluorinated or perfluorinated heteroaryl, it is recommended to delete “halogen, F, Cl, CN, partially fluorinated or perfluorinated C1 to C8 alkyl, partially fluorinated or perfluorinated C6 to C12 aryl, or partially fluorinated or perfluorinated C2 to C12 heteroaryl” from the list of substituents to eliminate redundancy.
In claim 29, it is recommended to replace “m and n are selected 1” with “m and n are selected as 1” for ease of reading.
In claims 35-38, it is recommended to replace “the semiconductor layer” with “the at least one semiconductor layer” for consistency and ease of reading.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 20-39 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Independent claim 20 and claim 21 require at least one metal compound comprising at least one ligand L, which comprises at least one ligand fragment Y, wherein the at least one ligand fragment Y has a directed dipole moment of less than -3.6 debye. Claims 20-21 do not further define the at least one ligand fragment Y by a specific structure or general formula. Thus, as the at least one ligand fragment Y is so broadly defined, the at least one ligand fragment Y may contain any number of chemical groups and substituents, and these may include any functional group, ring, or atom.
The instant description recites the ligand fragment Y may be represented by formula (IV), wherein examples of the ligand fragment Y include structures of D1 to D11 (see instant pgs. 21-26). The instant description further teaches examples of ligand fragments Y and their corresponding directed dipole moments in Table 1 (see formulas K1 to K31 in Table 1 on pgs. 31-35). The formulas K1 to K31 only have directed dipole moments in the range of -3.64 debye to -7.5 debye, which is much narrower than the claimed range of a directed dipole moment of less than -3.6 debye. Accordingly, the description only provides 31 examples of ligand fragments Y (formulas K1 to K31) which satisfy a directed dipole moment of less than -3.6 debye, and the description does not provide examples of ligand fragments Y which satisfy the full range of a directed dipole moment of less than -3.6 debye. For example, the instant description fails to provide examples of ligand fragments Y which have a directed dipole moment of less than -7.5 debye, which is within the scope of claim 20.
As such, the specification provides exceptionally broad guidance on what ligand fragments Y might be useable but provides no further description of which ligand fragments Y may satisfy having a directed dipole moment of less than -3.6 debye. The limited examples described in the written description do not provide a representative number of species sufficient to show that Applicant was in possession of the claimed genus (see MPEP 2163-II-A-1-ii).
Claims 21-39 are further rejected for being dependent upon claim 20.
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 20-39 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claims 20-21 recite the broad recitation “the metal compound comprises a metal M and at least one ligand L or the metal compound has the formula (I)”, and the claim also recites “the metal compound comprises a metal M, and at least one ligand L” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claims 25-26 recite the broad recitation “R’, R”, and R”’ are independently selected from H, D, electron-withdrawing group, F, perfluorinated C1 to C24 alkyl”, and the claim also recites “preferably CF3, CN, SCN, OCF3, -NO2, or -SF5” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claims 20-21 recite A1 and A2 are selected from groups that may be substituted or unsubstituted wherein
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.
Claims 20-21 later recite the at least one ligand fragment Y is selected from groups that may be substituted or unsubstituted. It is unclear if the definition of “the substituents” above apply only to the groups listed for A1 and A2, or if the definition of “the substituents” also apply to the at least one ligand fragment Y. For purposes of examination, the definition of “the substituents” will be interpreted as applying only to the groups listed for A1 and A2.
Claims 31 and 33 recite Ra and Rb are selected from groups that may be substituted or unsubstituted wherein
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Claims 31 and 33 later recite the at least one ligand fragment Y is selected from groups that may be substituted or unsubstituted. It is unclear if the definition of “the substituents” above apply only to the groups listed for Ra and Rb, or if the definition of “the substituents” also apply to the at least one ligand fragment Y. For purposes of examination, the definition of “the substituents” will be interpreted as applying only to the groups listed for Ra and Rb.
Claim 32 recites the limitation "Ra and Rb" in line 1. There is insufficient antecedent basis for this limitation in the claim.
Claims 21-39 are further rejected for being dependent upon indefinite claim 20.
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 20-26 and 28-39 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang (English translation of CN 111018921 A obtained from Google Patents) in view of Bhandari (US 2015/0188089 A1), supporting evidence provided by Table 3.3. Work Functions of Some Common Metals; and Zinc Stannate Powder - Nanorh; December 7, 2020. Accessed September 28, 2026.
Regarding claims 20-26 and 28-39, Zhang teaches an electroluminescent device having improved light emitting performance and service life by including a metal complex comprising a ligand L represented by Formula 1 (abstract; bottom of pg. 95-pg. 96). Zhang teaches examples of such devices including that of Example 2 which includes a substrate, an anode of ITO, a hole injection layer, a first hole transport layer (semiconductor layer) comprising compound HT doped with Fe(La77)3 (90:10), a second hole transport layer, an emissive layer, an electron transport layer, and a cathode (bottom of pg. 114; Table 1 on pg. 116; structure on pg. 112).
Formula 1:
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Fe(La77)3:
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Zhang fails to teach the dipole moment of a ligand fragment of Fe(La77)3. However, Zhang does teach in Formula 1 that Ra1 and Ra3 may be aryl groups having 6 carbon atoms substituted with fluorine and CN (bottom of pg. 96; beginning of pg. 99; bottom of pg. 102). Additionally, Zhang teaches the thermodynamics, electrochemical properties, and HOMO/LUMP energy levels of the metal complex can be adjusted by changing the substituent groups (beginning of pg. 98). Zhang further teaches alternative examples of the ligand L represented by Formula 1 including the ligand La757 (see pg. 93).
La757:
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Therefore, given the general formula and teachings of Zhang, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the ligand
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with the ligand La757, because Zhang teaches the ligand represented by Formula 1 may suitably be selected as La757. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful in the hole transport layer of the device of Zhang and possess the benefits taught by Zhang above. See MPEP 2143.I.(B).
In particular, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select the ligand La757, because it would have been choosing from a list of exemplified ligands represented by Formula 1 and taught by Zhang, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the in the hole transport layer of the device of Zhang and possessing the benefits taught by Zhang above. One of ordinary skill in the art would have been motivated to produce additional compounds comprising ligands represented by Formula 1 having the benefits taught by Zhang in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified compound shown below is herein after referred to as Fe(La757)3.
Fe(La757)3:
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Fe(La757)3 is a metal compound that comprises a metal Fe (claim 30) and at least one ligand L. The ligand L comprises at least one coordinating linker X and at least one ligand fragment Y wherein:
The coordinating linker X is represented by formula (IIa)
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(claims 28-29) and formula (IIb)
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(claim 31) wherein
m and n are each 1;
Z is CR1;
A1 is C=O and A2 is C-O, and A1 and A2 form a cycle with Z;
R1 is a ligand fragment Y that is a C6 aryl substituted with F and CN (claim 34);
Ra and Rb contain a ligand fragment Y and are each a C6 aryl substituted with F and CN (claim 32);
The at least one ligand fragment Y is a substituted C6 aryl and reads on the formula (IV)
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(claims 24-26) wherein:
q is 0;
Ar1 is not required to be present;
U1 is CR’, U2 is CR”, and U3 is CR’”; and
R’ and R’” are each F and R” is CN, and F and CN are each an electron-withdrawing group (see middle of instant pg. 11).
As the substituents of the at least one fragment Y is a C6 aryl substituted with F and CN, the limitations of claim 22 are met. Additionally, the at least one ligand L is represented by formula (III) (claim 33).
Zhang appears silent with respect to the property of the directed dipole moment of the ligand fragment Y
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.
The instant specification recites that the ligand fragment K9 has a directed dipole moment of -5.58 debye (see instant pg. 32). Since Zhang teaches the ligand fragment Y above, the same structure as the ligand fragment K9 disclosed by the Applicant, the ligand fragment Y having a directed dipole moment of -5.58 debye is considered to be inherent (and would be expected to fall within the range in the claim), absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP 2112. Accordingly, the limitations of claim 23 are met.
As discussed above, Zhang teaches an anode of ITO and thus fails to teach an anode having a first and second sub-layer.
Bhandari teaches an organic light emitting diode having increased light extraction by including at least one of a first and second electrode that is a light extracting electrode having a metallic layer (abstract). Bhandari teaches an example of such an anode having the structure of zinc stannate (Zn2SnO4)/Ag/Ti/zinc stannate (see Example 3 in ¶ [0197]).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute Zhang’s anode of ITO with the anode as shown in Example 3 of Bhandari, based on the teaching of Bhandari. The motivation for doing so would have been to provide an organic light emitting diode with increased light extraction, as taught by Bhandari.
The resulting anode has the structure of zinc stannate/Ag/Ti/zinc stannate. The layer of Ag reads on the claimed first anode sub-layer as it has a work function of 4.6 eV1. The second layer of zinc stannate reads on the claimed second anode sub-layer as zinc stannate is a transparent conductive oxide2.
Per claim 36, the first hole transport layer is in direct electrical contact with the anode.
Per claim 38, the compound HT of the first hole transport layer is a non-polymeric compound (see structure on pg. 117 of Zhang).
Claim 27 is rejected under 35 U.S.C. 103 as being unpatentable over Zhang (English translation of CN 111018921 A obtained from Google Patents) in view of Bhandari (US 2015/0188089 A1) as applied to claim 20 above, and further in view of Schmid (US 2017/0317288 A1).
Regarding claim 27, Zhang in view of Bhandari teach the device including the compound Fe(La757)3 in the first hole transport layer, as described above with respect to claim 20.
Fe(La757)3:
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Fe(La757)3 fails to include a ligand fragment Y that reads on one of the groups D1 to D11. However, Zhang does teach in Formula 1 that Ra1 to Ra3 may be aryl groups having 6 carbon atoms substituted with CF3 and CN (bottom of pg. 96; bottom of pg. 102). Additionally, Zhang teaches the thermodynamics, electrochemical properties, and HOMO/LUMP energy levels of the metal complex can be adjusted by changing the substituent groups (beginning of pg. 98).
Schmid teaches a metal complex for use as a dopant in a hole-transport layer (¶ [0016] and [0090]). Schmid teaches high thermal stability and good conductivity may be obtained when a -CF3 group is used as a substituent in the metal complex (¶ [0058]-[0059]). Additionally, by using multiple -CF3 groups as substituents, further improvement in thermal stability may be achieved (¶ [0062]).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the -F groups of Fe(La757)3 with -CF3 groups, based on the teaching of Schmid. The motivation for doing so would have been to provide high thermal stability and good conductivity, as taught by Schmid.
The resulting modified compound includes ligand fragments Y that read on the group D1.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRAELYN R WATSON whose telephone number is (571)272-1822. The examiner can normally be reached M-F 7:30am-5pm.
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.
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/BRAELYN R WATSON/Primary Examiner, Art Unit 1786
1 Table 3.3. Work Functions of Some Common Metals. Retrieved from https://app.knovel.com/hotlink/itble/rcid:kpSRIE0001/id:kt012QOR11/sensors-ranging-imaging/table-3-3-work-functions.
2 Zinc Stannate Powder – Nanorh; December 7, 2020. Accessed September 28, 2026. https://www.nanorh.com/product/zinc-stannate-powder/. See middle of pg. 2
