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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 05/28/2026 has been entered.
Response to Amendment
In the response filed 05/28/2026, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(a) of claims 1-8 and 10-25 as failing to comply with the written description requirement is withdrawn by the Office.
Claims 1-24 were originally filed.
Claim 25 has been added.
Claim 9 is canceled.
Claims 1-2, 7-8, and 10 are instantly amended.
Claims 1-8 and 10-25 are pending in the application.
Response to Arguments
Applicant's arguments with respect to the rejections over Haruyama and King have been fully considered but they are not persuasive.
With respect to Applicant’s argument that applying the teachings of King to the teachings of Haruyama is improper because King teaches a particular relationship between a phosphorescent Ir(ppy)3 derivative and a fluorescent polymer host material, Examiner disagrees.
While King does use a fluorescent, polyfluorene-based polymer as the host material in the example devices, King teaches that a polyfluorene polymer has been used only on the basis that it is one of the most common classes of conjugated polymers suitable for use in light emitting devices (page 1043, Col. 2). King states in the conclusion that the results of the experiments are meant to apply to any system wherein energy transfer from the phosphorescent guest to the fluorescent host is energetically favorable (page 1049, Col. 1).
The most relevant teaching of King is that it was found that the introduction of bulky side groups onto the phosphorescent organometallic dopant reduced the rate of energy transfer by the Dexter mechanism by reducing the orbital overlap necessary for Dexter transfer to take place. King states that the substitutions form a shell, effectively preventing energy transfer from the 3MLCT state to the polymer material, and achieving three to six times improvement in device performance (Conclusion, page 1049). In this respect, Examiner agrees that King teaches promoting phosphorescent emission from the 3MLCT state of the organometallic complex. Where Examiner disagrees is Applicant’s assertion that King’s bulky organometallic compound is incompatible with Haruyama because King and Haruyama teach different light-emitting mechanisms.
Haruyama teaches an embodiment of the claimed invention which includes a light-emitting layer containing a first material with the function of converting triplet excitation energy into light emission (such as a phosphorescent organometallic compound), and a second material with the function of converting singlet excitation energy into light emission (a fluorescent light-emitting material), and the second material comprises a luminophore with five or more protecting groups (abstract). In Haruyama’s Example 5 of a Light-Emitting Layer (paragraphs 0324-0338), the light emitting layer contains compounds 131, 132, 133, and 134, wherein compound 133 is a phosphorescent material (paragraph 0331) and has the function of converting triplet excitation energy into light emission (paragraph 0324, lines 1-7), and also serves as a donor (paragraph 0331, lines 19-20).
Haruyama teaches that because the second, fluorescent material, 132, has bulky protecting groups, the structure inhibits transfer by the Dexter mechanism, leading to inhibition of deactivation of triplet excitation energy, and a fluorescent element with high emission efficiency. Also, as transfer by the Dexter mechanism is inhibited, energy transfer by the Forster mechanism is increased in rate, leading to shorter excitation lifetime of the energy acceptor, and improved reliability of the light emitting element (paragraph 0337).
Thus, the goals and mechanisms of Haruyama and King are not different. Rather, both Haruyama and King seek to suppress energy transfer through the Dexter mechanism, as doing so results in three to six times improvement in device performance, as taught by King, and an increased rate of energy transfer by the Forster mechanism, leading to shorter excitation lifetime of the energy acceptor, and improved reliability of the light emitting element, as taught by Haruyama.
For at least these reasons, the rejection of record is maintained.
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 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.
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.
Claims 1-8, 10-15, 17, and 19-25 are rejected under 35 U.S.C. 103 as being unpatentable over Haruyama et al. (WO 2019/171197 A1, using US 2021/0043840 A1 as an official translation and for references), and further in view of King et al. (King, S.M; Al-Attar, H.A.; Evans, R.J.; Congreve, A.; Beeby, A.; Monkman, A.P., 2006, The Use of Substituted Iridium Complexes in Doped Polymer Electrophosphorescent Devices: The Influence of Triplet Transfer and Other Factors on Enhancing Device Performance, Adv. Funct. Mater., 16, 1043-1050).
With respect to claim 1, Haruyama discloses a light-emitting device comprising a first electrode (an anode), a second electrode (a cathode), and a light emitting layer between the electrodes (paragraph 0248) comprising a phosphorescent iridium compound (paragraph 0318) that transfers energy from a triplet state to a light-emitting material that emits fluorescence (paragraph 0268).
Haruyama gives an example of the fluorescent material in Compound (102), which is pictured below.
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This compound meets the requirements of the instant claim because it comprises an anthracene core which has an amine skeleton and has at least five or more second substituents which are branched C4 alkyl groups (t-butyl).
However, while Haruyama teaches that the phosphorescent material preferably comprises a phosphorescent, iridium based ortho-metalated ligand (paragraph 0425, lines 4-7) which has the function of converting triplet excitation energy into light emission (paragraph 0324, lines 1-7), and also serves as a donor (paragraph 0331, lines 19-20), Haruyama does not teach the iridium compound has at least one first substituent which is a branched alkyl group.
In analogous art, King teaches phosphorescent, phenylpyridine based iridium complexes with bulky substituents which are used to transfer energy to a fluorescent material in the light emitting layer of an organic light emitting device (abstract).
King teaches that introduction of bulky side groups onto the phosphorescent organometallic dopant reduces the rate of energy transfer by the Dexter mechanism by reducing the orbital overlap necessary for Dexter transfer to take place. King states that the substitutions form a shell, effectively preventing energy transfer from the 3MLCT state to the fluorescent material and achieving three to six times improvement in device performance when two t-butyl groups are substituted onto the ligand of the iridium complex (Conclusion, page 1049). An example of such a compound is given in Compound 2 (Figure 3), which is pictured below.
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Examiner notes that King teaches that phosphorescence of the compound takes place at room temperature (Figure 6).
This compound meets the requirements of the instant organometallic complex when the first and second rings are six-membered, the transition metal is iridium, and the compound comprises a first substituent which is a C4 branched alkyl which is substituted on both of the first and second rings.
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 doubly-substituted compound (2) of King as the ortho-metalated iridium phosphorescent triplet energy source in the device of Haruyama in order to achieve a compound which reduces the orbital overlap necessary for Dexter transfer to take place, preventing energy transfer from the 3MLCT state to the fluorescent material, resulting in a three to six times improvement in device performance, as taught by King.
Examiner is interpreting the combination of these compounds to meet the requirements of the instant claim through their use as preferred embodiments of the claimed invention, as given on pages 25 (compound 109) and 35 (compound 2tBu-mmtBuDPhA2Anth) 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 compounds of Haruyama and King read on the claims.
Haruyama and King are silent to the longest-wavelength edge at a first wavelength in nm of the compound of Haruyama being longer than the shortest-wavelength edge at a second wavelength in nm of the compound King. 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 the light-emitting material of Haruyama and the organometallic of King are used as a composition of the emissive 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 Haruyama and King, 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 Haruyama and King was first provided. See MPEP 2112.01 (II).
With respect to claim 2, Haruyama and King teach the device of claim 1, and the carbon atom bonded to the iridium core is bonded to the iridium atom through a covalent bond, and the nitrogen atom bonded to the iridium core is bonded to the iridium atom through a coordinate bond.
With respect to claim 3, Haruyama and King teach the device of claim 1, and the ligand is a phenylpyridine derivative and one first substituent is bonded to a carbon atom of the phenylpyridine skeleton, as pictured above.
With respect to claim 4, Haruyama and King teach the device of claim 1, and the organometallic does not comprise any n-alkyl group.
With respect to claim 5, Haruyama and King teach the device of claim 1, as discussed above.
Examiner is interpreting the combination of compounds pictured and discussed above in claim 1 to meet the requirements of instant formula (1) through their use as preferred embodiments of the claimed invention, as given on pages 25 (compound 109) and 35 (compound 2tBu-mmtBuDPhA2Anth) 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 compounds of Haruyama and King read on the claims.
Haruyama and King are silent to the relationship between the first wavelength and the second wavelength meeting the requirements of instant formula (1). 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 the light-emitting material of Haruyama and the organometallic of King are used as a composition of the emissive 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 Haruyama and King, 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 Haruyama and King was first provided. See MPEP 2112.01 (II).
With respect to claim 6, Haruyama and King teach the device of claim 1, as discussed above.
Examiner is interpreting the combination of compounds pictured and discussed above in claim 1 to meet the requirements of instant formula (2) through their use as preferred embodiments of the claimed invention, as given on pages 25 (compound 109) and 35 (compound 2tBu-mmtBuDPhA2Anth) 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 compounds of Haruyama and King read on the claims.
Haruyama and King are silent to the fluorescence spectrum of the light-emitting material comprising a shortest wavelength edge at a third wavelength in nm satisfying instant formula (2). 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 the light-emitting material of Haruyama and the organometallic of King are used as a composition of the emissive 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 Haruyama and King, 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 Haruyama and King was first provided. See MPEP 2112.01 (II).
With respect to claim 7, Haruyama discloses a light-emitting device comprising a first electrode (an anode), a second electrode (a cathode), and a light emitting layer between the electrodes (paragraph 0248) comprising a phosphorescent iridium compound (paragraph 0318) that transfers energy from a triplet state to a light-emitting material that emits fluorescence (paragraph 0268).
Haruyama gives an example of the fluorescent material in Compound (102), which is pictured below.
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This compound meets the requirements of the instant claim because it comprises an anthracene core which has an amine skeleton and has at least five or more second substituents which are branched C4 alkyl groups (t-butyl).
However, while Haruyama teaches that the phosphorescent material preferably comprises a phosphorescent, iridium based ortho-metalated ligand (paragraph 0425, lines 4-7) which has the function of converting triplet excitation energy into light emission (paragraph 0324, lines 1-7), and also serves as a donor (paragraph 0331, lines 19-20), Haruyama does not teach the iridium compound has at least one first substituent which is a branched alkyl group.
In analogous art, King teaches phosphorescent, phenylpyridine based iridium complexes with bulky substituents which are used to transfer energy to a fluorescent material in the light emitting layer of an organic light emitting device (abstract).
King teaches that introduction of bulky side groups onto the phosphorescent organometallic dopant reduces the rate of energy transfer by the Dexter mechanism by reducing the orbital overlap necessary for Dexter transfer to take place. King states that the substitutions form a shell, effectively preventing energy transfer from the 3MLCT state to the fluorescent material and achieving three to six times improvement in device performance when two t-butyl groups are substituted onto the ligand of the iridium complex (Conclusion, page 1049). An example of such a compound is given in Compound 2 (Figure 3), which is pictured below.
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Examiner notes that King teaches that phosphorescence of the compound takes place at room temperature (Figure 6).
This compound meets the requirements of the instant organometallic complex when the first and second rings are six-membered, the transition metal is iridium, and the compound comprises a first substituent which is a C4 branched alkyl which is substituted on both of the first and second rings.
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 doubly-substituted compound (2) of King as the ortho-metalated iridium phosphorescent triplet energy source in the device of Haruyama in order to achieve a compound which reduces the orbital overlap necessary for Dexter transfer to take place, preventing energy transfer from the 3MLCT state to the fluorescent material, resulting in a three to six times improvement in device performance, as taught by King.
Examiner is interpreting the combination of these compounds to meet the requirements of the instant claim through their use as preferred embodiments of the claimed invention, as given on pages 25 (compound 109) and 35 (compound 2tBu-mmtBuDPhA2Anth) 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 compounds of Haruyama and King read on the claims.
Haruyama and King are silent to the longest-wavelength edge at a first wavelength in nm of the compound of Haruyama being longer than the shortest-wavelength edge at a second wavelength in nm of the compound King. 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 the light-emitting material of Haruyama and the organometallic of King are used as a composition of the emissive 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 Haruyama and King, 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 Haruyama and King was first provided. See MPEP 2112.01 (II).
With respect to claim 8, Haruyama and King teach the device of claim 7, and the carbon atom bonded to the iridium core is bonded to the iridium atom through a covalent bond, and the nitrogen atom bonded to the iridium core is bonded to the iridium atom through a coordinate bond.
With respect to claim 10, Haruyama and King teach the device of claim 7, and at least three second substituents of the five or more second substituents are not directly bonded to the condensed aromatic ring, as pictured above.
With respect to claim 11, Haruyama and King teach the device of claim 7, and the light-emitting material comprises a diarylamino group and the anthracene skeleton is bonded to the nitrogen atom of the diarylamino and at least five or more of the second substituents are bonded to the aryl group or the diarylamino, as pictured above.
With respect to claim 12, Haruyama and King teach the device of claim 7, and the branched alkyl group is a tertiary alkyl group (t-butyl).
With respect to claim 13, Haruyama and King teach the device of claim 7, and the branched alkyl group comprise 4 carbon atoms in total (t-butyl).
With respect to claims 14-15, Haruyama and King teach the device of claim 7, as discussed above, and each of the second substituents is a t-butyl group.
However, for the sake of discussion, Haruyama teaches a cycloalkyl group through compounds such as compounds (204) and (205) (page 27), and a trialkyl silyl group through compounds (206) and (207) (page 27).
With respect to claim 17, Haruyama and King teach the device of claim 1, and the branched alkyl of the first substituent is a tertiary alky group (t-butyl), as pictured above.
With respect to claim 19, Haruyama and King teach the device of claim 1, and Haruyama teaches that the light-emitting layer may further comprise a host material (paragraph 0015).
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 host material in the light-emitting layer of Haruyama and King as taught by Haruyama.
With respect to claim 20, Haruyama and King teach the device of claim 1, and the organometallic complex of King meets the requirements of instant General Formula (G0) when n is 3, L is not present, and R104 and R108 are a C4 alkyl (t-butyl) substituent, and all other R groups are hydrogen atoms, as pictured above.
With respect to claim 21, Haruyama and King teach the light-emitting device of claim 1, and Haruyama teaches the device may be an apparatus (paragraph 0530) and comprise a substrate such as glass, plastic, or the like (paragraph 0470).
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 form the apparatus on a substrate, as taught by Haruyama.
With respect to claim 22, Haruyama and King teach the device of claim 1, and Haruyama teaches the device may be a display device (paragraph 0557), and may comprise a substrate such as glass, plastic, or the like (paragraph 0470).
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 device of Haruyama and King in a display device comprising a substrate, as taught by Haruyama.
With respect to claim 23, Haruyama and King teach the apparatus of claim 21, and Haruyama also teaches a portable information terminal (an apparatus) which comprises a housing (paragraph 0560).
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 give the apparatus a housing, as taught by Haruyama.
With respect to claim 24, Haruyama and King teach the display device of claim 22, and Haruyama also teaches an electronic device comprising a least one of a sensor, an operation button, a speaker, and a microphone (paragraph 0570).
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 give the electronic device at least a power button (an operation button), as taught by Haruyama.
With respect to claim 25, Haruyama and King teach the device of claim 7, and the organometallic complex of King is represented by instant General Formula (G0) when n is 3 and L is not present, and R104 and R108 are a C4 alkyl (t-butyl) substituent, and all other R groups are hydrogen atoms, as pictured above.
Claims 16 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Haruyama et al. (WO 2019/171197 A1, using US 2021/0043840 A1 as an official translation and for references), and further in view of King et al. (King, S.M; Al-Attar, H.A.; Evans, R.J.; Congreve, A.; Beeby, A.; Monkman, A.P., 2006, The Use of Substituted Iridium Complexes in Doped Polymer Electrophosphorescent Devices: The Influence of Triplet Transfer and Other Factors on Enhancing Device Performance, Adv. Funct. Mater., 16, 1043-1050) as applied above, and further in view of Li et al. (US 2002/0076576 A1).
With respect to claims 16 and 18, Haruyama and King teach the light-emitting device of claim 1 and claim 7, as discussed above.
However, neither Haruyama nor King teach the presence of a deuterium atom.
Li teaches organic semiconductors consisting of a chromophore in which one or more hydrogen atoms is replaced with a deuterium atom. Li teaches that deuterated organic semiconductors have improved performance, for instance, high 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 a deuterium atom into the compound of Haruyama or King in order to improve the compounds performance, and obtain higher fluorescence and more stability than its non-deuterated analogue, as taught by Li.
Conclusion
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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