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 .
Summary of Claims
Claims 1, 3-13, 15-19, and 22-23 are amended and claims 25-27 are new due to Applicant's amendment dated 09/09/2026. Claims 1-27 are pending.
Response to Amendment
The rejection of claims s 1-3, 5-8, 11-14, and 17-24 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 as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 09/09/2026. The rejection is withdrawn.
The rejection of claims 3-13, 15-16, 19, and 22-23 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 as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 09/09/2026. The rejection is withdrawn.
The rejection of claims 1-24 under 35 U.S.C. 103 as being unpatentable over Tsai (US 2021/0054010 A1) in view of Cai (US 2020/0091442 A1), Babudri (“Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom.” Chemical Communications, (2007), pgs. 1003-1022) and Zhao (Cn 111808142 A) is hereinafter revised to reflect the amended claim language due to the Applicant’s amendment dated 09/09/2026.
Response to Arguments
Applicant’s arguments on pages 93-101 of the reply dated 09/09/2026 with respect to the rejection of claims 1-24 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –On pages 93-96, Applicant argues metal complexes of the present invention in Examples 1 and 2 (comprising complexes 134 and 150, respectively) obtain unexpected results over Comparative Examples 1, 2, and 3 (comprising compounds GD1, GD2, and GD3, respectively). Particularly, Applicant argues the inventive examples obtain improved efficiency, FWHM, and a more saturated green emission spectrum.
134:
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150:
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GD1:
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GD2:
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GD3:
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Examiner's response –Overcoming a rejection based on unexpected results requires at least the combination of three different elements: (i) the results must fairly compare with the closest prior art in an affidavit or declaration under 37 CFR 1.132, (ii) the claims must be commensurate in scope, and (iii) the results must truly be unexpected. MPEP 716.02. Additionally, the burden rests with Applicant to establish the results are unexpected and significant. MPEP 716.02(b).
Comparison with closest prior art
Applicant has not made a comparison to the closest prior art. The device examples of the instant specification comprise different materials than the devices of Tsai.
As discussed below and in the previous rejection, Tsai teaches the complex LA1-1-9(LB28)2. As shown by the structure below, LA1-1-9(LB28)2 comprises a phenyl-pyridine ligand substituted with CD3 in the meta position of the pyridine ring with respect to the N-Ir bond and in the meta position of the phenyl ring with respect to the C-Ir bond. Additionally, LA1-1-9(LB28)2 comprises a CD3 substituent in the position corresponding to the claimed Y2.
LA1-1-9(LB28)2:
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In contrast, the metal complexes 134, 150, and GD1 to GD3 all comprise a phenyl-pyridine ring substituted with t-butyl in the meta-position of the pyridine ring with respect to the N-Ir bond, and none of the comparative compounds GD1 to GD3 comprise only a CD3 substituent in the position corresponding to the claimed Y2.Given these differences, a comparison to the closest prior art has not been made and Applicant has not provided an explanation regarding this difference. It is unclear if compounds comprising the same structure as LA1-1-9(LB28)2 that also contain a fluorine in the location of Ry and a cyano or fluorine in the location of Rx would obtain the same results discussed by Applicant.
Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, and if not explained should be noted and evaluated, and if significant, explanation should be required. MPEP 716.02(e).
Commensurate in Scope
The data shown in instant Tables 1-2 is not commensurate in scope with the claimed invention for at least the reasons that the data is shown for the use of a compound in the EML of a device, whereas claims 1-19 and 25-27 are directed to a compound. The improved properties of efficiency, FWHM, and a more saturated green emission spectrum are shown when the compound is used in an EML of an OLED (and with other particular compounds present in the same layer, such as host Compounds H1 and H2). None of these limitations are required by the claim. No evidence has been provided to show that the unexpected results would be present for the use of the compound in other layers (or with other compounds present in the same layer).
Additionally, as discussed above, Tsai’s LA1-1-9(LB28)2 contains a phenyl-pyridine ligand substituted with CD3 in the meta position of the pyridine ring with respect to the N-Ir bond and in the meta position of the phenyl ring with respect to the C-Ir bond. This is within the scope of the claims. As there are no results comprising the structures of the prior art, it is unclear if the same results discussed by Applicant would be present.
Similarly, as discussed below and in the previous rejection, Tsai’s compound is modified with fluorine in the location of Rx, which is within the scope of the claims. As there are no results comprising structures wherein Rx is fluorine (and only wherein Rx is cyano), the data is not commensurate in scope with the claims.
Unexpected Results
While there is improvement in efficiency between the instant devices and comparative devices, it is unclear whether these performances are truly unexpected.
As discussed further in the rejection below, Babudri teaches fluorinated compounds obtain enhanced photoluminescent efficiency (abstract; pg. 1003, Introduction, second paragraph; pg. 1008, second column, sections i-v), and Zhao teaches a fluorine substituent in the meta-position with respect to the N-Ir bond of a pyridine ring provides improved current efficiency. Accordingly, it is unclear whether the degree of improvement shown by the data in the instant specifcation is truly unexpected.
Applicant's argument –On pgs. 96-97, Applicant argues Tsai does not teach Y2 and/or Y3 should contain a fluorine substituent, nor does Tsai suggest introducing fluorine or cyano substitution at the X1-X8 positions.
Examiner's response –While Tsai alone does not teach a complex that reads on the claimed Formula 1 wherein Y2 and/or Y3 contain a fluorine substituent, or a fluorine or cyano substitution at the X1-X8 positions, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See MPEP 2145 IV.
As discussed below and in the previous rejection, a fluorine substituent in the location of Y2 and/or Y3 and one of X1-X8 is within the scope of Tsai’s Formula I (see definitions for RA and RD in ¶ [0044]-[0046] and [0054]). Accordingly, given the benefits discussed by Cai, Babudri, and Zhao, it would have been obvious to one of ordinary skill in the art to modify Tsai’s compound to arrive at the claimed invention.
Applicant's argument –On pg. 97, Applicant argues that one of ordinary skill in the art would not have been motivated to fluorinate Tsai’s structure based on the teachings of Cai. Applicant argues the effect of fluorine substitution disclosed by Cai depends of the specific ligand structure disclosed therein and cannot be transferred to the distinct ligand system of Tsai.
Examiner's response –Cai teaches a metal complex comprising a partial structure represented by Formula 1 containing a fluorine substitution may provide much longer device lifetime, better thermal stability, and higher luminous efficiency (¶ [0012]-[0013]). Tsai’s compound LA1-1-9(LB28)2 includes a partial structure that reads on Cai’s Formula 1 except wherein it does not contain a fluorine substitution (see Cai, ¶ [0014]-[0019]).
1:
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LA1-1-9(LB28)2:
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Accordingly, it would have been obvious to one of ordinary skill in the art to modify Tsai’s compound to contain a fluorine substitution such that it contains a partial structure represented by Cai’s Formula 1 and thus obtains the benefits taught by Cai. As the resulting compound contains a partial structure represented by Cai’s Formula 1, there is nothing to suggest the benefits discussed by Cai would not be obtains by the modified compound of Tsai in view of Cai.
Applicant's argument –On pgs. 97-99, Applicant argues Babudri does not suggest fluorine substitution at the specific positions of the ligand structure disclosed by Tsai. Applicant argues the ligand structures and substitution positions of Babudri are different from those of the present application, and the technical effects of Babudri are unrelated to the technical effects of the present application.
Examiner's response –Babudri is not used to teach a substitution position, but is rather used to generally teach the benefits of a fluorinated compound in an electroluminescent device. As Babudri teaches benefits of fluorination apply to organometallic iridium complexes of light-emitting devices, Tsai’s compound is an organometallic iridium complex of a light-emitting device, and compounds of the instant application may be an organometallic iridium complex of a light-emitting device (for example, see at least Formula 3 in claim 4), the benefits discussed by Babudri are related and relevant to the present application (see Babudri, pg. 1018, section 6).
Applicant's argument –On pg. 99, Applicant argues Zhao does not provide any teaching or suggestion that fluorine substitution provides superior technical effects.
Examiner's response –As discussed below and in the previous rejection, Zhao teaches compound J001 and J087, which are identical except for wherein J087 contains a fluorine substituent in the meta position with respect to the N-Ir bond of a pyridine group (see pgs. 2 and 7). As shown by the data in Table 2, the device comprising J087 contains improved driving voltage and current efficiency in comparison to the device comprising J001. Accordingly, Zhao’s data suggests a specific fluorine substitution of an organometallic iridium complex provides improved properties.
Applicant's argument –On pgs. 99-101, Applicant argues arriving at a compound of the present invention would require a series of multiple, highly specific selections and sequential structural modifications that are not taught or suggested by the prior art. Applicant argues the proposed combination can only be achieved with the benefit of impermissible hindsight reconstruction.
Examiner's response –As discussed below and in the previous rejection, Cai, Babudri, and Zhao provide specific benefits for modifying the compound of Tsai to arrive at the claimed invention. While multiple modifications must be made to arrive at the claimed invention, it would have been obvious to one of ordinary skill in the art to do so to obtain the benefits discussed by Cai, Babudri, and Zhao.
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. As discussed above and outlined below, the rejections take into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the Applicant's disclosure.
Applicant's argument –On pgs. 101, Applicant argues the prior art fail to teach the newly added claims 25-26.
Examiner's response –As discussed in greater detail in the new grounds of rejection below, the prior art teaches the newly added claims 25-26.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-24 and 26-27 are rejected under 35 U.S.C. 103 as being unpatentable over
Tsai et al. (US 2021/0054010 A1; hereinafter “Tsai”) in view of Cai et al. (US 2020/0091442 A1; hereinafter “Cai”), Babudri et al. (“Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom.” Chemical Communications, (2007), pgs. 1003-1022; hereinafter “Babudri”), and Zhao et al. (CN 111808142 A; hereinafter “Zhao”).
Regarding claims 1-14 and 16-19, Tsai teaches organometallic complexes comprising a ligand of Formula I (Tsai, see below, [Abstract]) wherein:
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ring A can be selected as pyridine (Z1 is a carbon atom and Z2 is a nitrogen atom, ¶ [0056]); and
RA, RB, RC, and RD can be selected as fluorine, alkyl groups, or aryl groups (¶ [0044]-[0046], [0054]); and
Y can be selected as an oxygen atom or a sulfur atom (¶ [0055]); and
X1-X8 can be selected as carbon atoms (¶ [0059]); and
Ring D can be selected as a substituted or unsubstituted 6-membered aromatic ring (¶ [0063]).
Tsai teaches organic electroluminescent devices, comprising organometallic complexes with ligand of Formula 1 as dopants in the light emitting layer, that exhibit narrower FWHM and higher efficiencies (¶ [0168]-[0171]; see also Tables 1-2).
Tsai specifically discloses the following iridium complex LA1-1-9(LB28)2; ¶ [0093], see structure below) which reads on the limitations of Formulae 1 and 2 of claim 1 of
the instant application, but fails to include the following wherein:
Y2 and/or Y3 are selected from CRy and Ry is fluorine; and
at least one of X1-X8 is selected from CRx and Rx is cyano or fluorine.
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Cai teaches organometallic complexes of Formula 2 (Cai) (shown below, ¶ [0103]) wherein:
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R1, R3, R4, Ra, and Rb, can each independently be hydrogen, a halogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl (¶ [0105]); and
metal complexes, such as those of Formula 2 (Cai), bearing a fluorine atom (at the position circled) on the dibenzo-moiety of the pyridyl-dibenzo ligand provide longer device lifetimes, better thermal stability, and higher luminous efficiency (¶ [0011]).
Cai discloses the following compound represented by Formula 2 (Cai):
Compound Ir(La94)(Lb1)2 (¶ [0134]-[0144], see structure below) and discloses an organic electroluminescent device comprising Compound Ir(La94)(Lb1)2 as a dopant in the light emitting layer (see Example 1 in Tables 1 and 2).
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Additionally, Cai teaches that devices comprising other iridium complexes as dopants in the light emitting layer (¶ [0192]; see Compounds D, E, F, G) wherein the fluorine substituent is transposed to different positions on the pyridyl-dibenzofuranyl ligand exhibit diminished lifetimes relative to the device comprising Compound Ir(La94)(Lb1)2 (see Comparative Examples 4-7 in Tables 1 and 2; ¶ [0198]).
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 hydrogen atom on the dibenzofuranyl moiety of compound LA1-1-9(LB28)2 of Tsai with a fluorine atom at position X7 (per Formula 1 of claim 1 of the instant application), based on the teaching of Cai. The motivation for doing so would have been to improve device lifetime, as taught by Cai.
Additionally, 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 hydrogen atom on the dibenzofuranyl moiety of compound LA1-1-9(LB28)2 of Tsai with a fluorine atom at position X7 (per Formula 1 of claim 1 of the instant application), because it would have been choosing among the preferable substituents for RC of Tsai, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the dopant in the light emitting layer of the organic electroluminescent device of Tsai and possessing the benefits taught by Tsai. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 1 of Tsai having the benefits taught by Tsai 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 compound of Tsai, as modified by Cai, is shown below, wherein the fluorine substitution is indicated with a circle.
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Tsai, as modified by Cai, fails to teach Y2 and/or Y3 (per Formula 1 of the instant application) as CRy wherein Ry is a fluorine atom as required by claim 1. Babudri teaches electroluminescent devices comprising fluorinated compounds that obtain higher lifetimes, and that specifically replacing C-H bonds with C-F bonds may enhance photoluminescent efficiency in an electroluminescent organometallic compound (abstract; pg. 1003, Introduction, second paragraph; pg. 1008, second column, sections i-v).
Tsai, as modified by Cai and Babudri, fails to teach a specific site of modification regarding the replacement of a C-H bond with a C-F bond. Zhao teaches substantially identical compounds (see Chemical Formula 1, pg. 1) to Tsai for use in OLEDs, as shown by J001 (pg. 2) and J087 (pg. 7; see structures below).
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The compounds J001 and J087 are identical except for wherein J087 contains a fluorine substituent in the meta-position with respect to the Ir-N bond of the pyridyl moiety. As shown by the data in Table 2 (pgs. 15-16), the device comprising J087 obtains improved driving voltage and current efficiency in comparison to the device comprising J001.
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 a fluorine atom in the meta-position of the pyridyl moiety with respect to the Ir-N bond of LA1-1-9(LB28)2 (Tsai: Cai Modification), as shown by compound J087 of Zhao, based on the teachings of Babudri and Zhao. The motivation for doing so would have been to obtain a device with improved lifetime and enhanced photoluminescence efficiency, as taught by Babudri, and improved driving voltage and current efficiency, as taught by Zhao.
Additionally, 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 hydrogen atom on the pyridyl moiety of compound LA1-1-9(LB28)2 (Tsai: Cai Modification) with a fluorine atom at position Y3 (per Formula 1 of claim 1 of the instant application), because it would have been choosing among the preferable substituents for RA of Tsai, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the dopant in the light emitting layer of the organic electroluminescent device of Tsai and possessing the benefits taught by Tsai. One of ordinary skill in the art would have been motivated to produce additional compounds represented by Formula 1 of Tsai having the benefits taught by Tsai 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 compound of Tsai, as modified by Cai, Babudri, and Zhao, is shown below, wherein the fluorine substitution of Baubdri and Zhao is indicated with a circle.
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Per claim 1, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on all the limitations of Formulae 1 and 2 wherein:
M is iridium (Ir); and
Z is an oxygen atom; and
Y1-Y4 are CRy wherein Y2 is substituted with a trideutero-methyl group and Y3 is substituted with a fluorine atom; and
X1-X8 are CRx; and
X1 is a carbon atom joined to the pyridyl moiety; and
X2 is a carbon atom forming a metal carbon bond; and
X7 is a carbon atom with a fluorine substituent; and
X8 is a carbon atom with a substituent Ar represented by Formula 2; and
The substituent Ar is a biphenyl group wherein Ar2 is an aromatic ring with 6 ring atoms, Ar1 is an aromatic ring with 6 ring atoms, and the total number of ring atoms in Ar1 and Ar2 is greater than 8; and
a of Formula 2 is an integer equal to 1; and
Y1, Y4, X3-X6, Ra1, and Ra2 are carbon atoms with hydrogen atoms as substituents.
Per claim 2, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications ) reads on all the limitations of Formula 1a as described previously.
Per claim 3, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications ) reads on all the limitations wherein:
the metal complex has the general of M(La)m(Lb)n(Lc)q; and
ligand La is as previously defined and m is an integer equal to 1; and
ligand Lb is represented by
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, wherein Ra and Rb are hydrogen atoms and substituted alkyl groups, and n is an integer equal to 2; and
ligand Lc is not required to be present (q is equal to zero).
Per claim 4, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications ) reads on all the limitations of Formula 3 of the instant application wherein:
ligand La is as previously defined and m is an integer equal to 1; and
R1, R3-R6, and R8 are all hydrogen atoms; and
R2 and R7 are trideutero-methyl groups.
Per claim 5, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein Z is selected as an oxygen atom.
Per claim 6, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein a of Formula 2 is an integer equal to 1.
Per claim 7, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
Y1-Y4 are CRy; and
Y2 is substituted with a trideutero-methyl group; and
Y3 is substituted with a fluorine atom; and
Y1 and Y4 are substituted with hydrogen atoms.
Per claim 8, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
Y1-Y4 are CRy; and
Y2 is substituted with a trideutero-methyl group; and
Y3 is substituted with a fluorine atom; and
Y1 and Y4 are substituted with hydrogen atoms.
Per claim 9, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
X7 is a carbon atom with a fluorine substituent; and
X8 is a carbon atom with a substituent Ar represented by Formula 2; and
The substituent Ar is a biphenyl group wherein Ar2 is phenyl, Ar1 is phenyl, and the total number of ring atoms in Ar1 and Ar2 is greater than 8; and
a of Formula 2 is an integer equal to 1.
Per claim 10, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
X7 is a carbon atom with a fluorine substituent; and
X8 is a carbon atom with a substituent Ar represented by Formula 2; and
The substituent Ar is a biphenyl group wherein Ar2 is phenyl, Ar1 is phenyl, and the total number of ring atoms in Ar1 and Ar2 is greater than 8; and
a of Formula 2 is an integer equal to 1.
Per claim 11, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein Ra1 and Ra2 are all hydrogen atoms
Per claim 12, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
Ar2 is an aromatic ring with 6 ring atoms; and
Ar1 is an aromatic ring with 6 ring atoms; and
the total number of ring atoms in Ar1 and Ar2 is greater than 8 and less than 30.
Per claim 13, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
Ar2 is a benzene ring; and
Ar1 is a benzene ring.
Per claim 14, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein Ar is selected as
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.
Per claim 16, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein:
R2 and R7 are substituted alkyl groups having 1 carbon atom (trideutero-methyl groups).
Per claim 17, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein ligand La is selected as La726 (see structure below).
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Per claim 18, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein ligand Lb is selected as Lb30 (see structure below).
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Per claim 19, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) reads on the limitation wherein the metal complex has the structure IrLa(Lb)2 and La is represented by La726 and Lb is represented by Lb30.
Regarding claims 20-24, Tsai teaches organic electroluminescent devices comprising:
an anode (ITO, ¶ [0168]); and
a cathode (Al, ¶ [0168]); and
an organic layer disposed between the anode and cathode wherein at least one layer of the organic layer comprises a metal complex (¶ [0168]); and
the organic layer comprising the metal complex is a light-emitting layer (¶ [0168]; and see Table 1); and
the light emitting layer further comprises two host compounds compounds H1 and H2, wherein compound H2 comprises triazine (see ¶ [0168], Table 1, and structures on pg. 119); and
the weight of the metal complex is 12% of the total weight of the light emitting layer (see ¶ [0168] and Table 2, Inventive Example); and
a compound combination comprising a metal complex (wherein the light emitting layer is interpreted as the compound combination).
Tsai teaches an anode, a cathode, and an organic layer and the compound is in the organic layer as discussed above. Tsai does not disclose a device comprising LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) as the metal complex dopant in the light emitting layer. It would have been obvious to one of ordinary skill in the pertinent art prior to the effective filing date of the claimed invention to use the compound LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) in the light emitting organic layer with the device structure of Tsai.
One of ordinary skill in the art would have been motivated to produce additional devices comprising compound LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) as the metal complex dopant in the light emitting layer having the benefits taught by Tsai in order to pursue the known options within his or her technical grasp with a reasonable expectation of success, absent any indication of unexpected results. See MPEP 2143.I.(E).
Regarding claim 15, LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) fails to read on the limitation wherein the total number of carbon atoms in all of R1 to R4 and/or R5 to R8 is at least 4.
Tsai does teach, however, that the ancillary ligand LB can be selected as the following substituted phenyl-pyridine ligand LB142 (¶ [0079] and see structure below).
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Therefore, given the teachings of Tsai, 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 phenyl-pyridine ancillary ligand on the compound LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications) with ancillary ligand LB142, because Tsai teaches that the ancillary ligand may be preferably selected as LB142. This substitution is depicted below with LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications 2).
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This substitution would have been one preferred element for another and one of
ordinary skill in the pertinent art would reasonably expect the predictable result that the
modified LA1-1-9(LB28)2 (Tsai: Cai, Babudri, and Zhao Modifications 2) would be useful as a metal complex dopant material in the light-emitting layer of an organic electroluminescent device of Tsai and possess the benefits taught by Tsai (narrower FWHM and higher efficiencies (¶ [0168]-[0171]). See MPEP 2143.I.(B).
Regarding claim 26, Tsai in view of Cai, Babudri, and Zhao teach LA1-1-9(LB28)2, as described above with respect to claim 1.
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LA1-1-9(LB28)2 fails to read on the claimed Formula 1 wherein Y2 is selected from CYy and Ry is F. However, Tsai teaches in Formula I that RA may be a substituent selected from combinations of deuterium, alkyl, and fluorine, and these substituents are not required to be in specific positions on ring A (¶ [0043]-[0046] and [0054]).
Therefore, given the general formula and teachings of Tsai, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of LA1-1-9(LB28)2 wherein the fluorine substituent is provided in the para-position of the pyridine ring with respect to the Ir-N bond, and the CD3 is provided in the meta-position of the pyridine ring with respect to the Ir-N bond. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Tsai’s Formula I in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful in the device of Tsai and possess the properties taught by Tsai. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. Compounds which are positional isomers or homologs are of sufficiently close structural similarity that there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II.
The resulting modified compound reads on the claimed Formula 1 wherein Y2 is selected from CYy and Ry is F.
Regarding claim 27, Tsai in view of Cai, Babudri, and Zhao teach LA1-1-9(LB28)2, as described above with respect to claim 1.
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LA1-1-9(LB28)2 fails to read on one of the claimed Metal Complexes 1 to 396. However, Tsai teaches the ancillary ligand LB may alternatively be selected as LB1 (¶ [0079]).
LB1:
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Therefore, given the general formula and teachings of Tsai, 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 LB28 with LB1, because Tsai teaches the ligand LB may suitably be selected as LB1. 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 as in the device of Tsai and possess the benefits taught by Tsai. See MPEP 2143.I.(B).
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 LB1, because it would have been choosing from a list of suitable ligands exemplified by Tsai as suitable for LB1, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in the device of Tsai and possessing the benefits taught by Tsai. One of ordinary skill in the art would have been motivated to produce additional compounds comprising a ligand of Formula I having the benefits taught by Tsai 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 resulting modified compound reads on claimed metal complex 31.
Claim 25 is rejected under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2021/0054010 A1; hereinafter “Tsai”) in view of Cai et al. (US 2020/0091442 A1; hereinafter “Cai”), Babudri et al. (“Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom.” Chemical Communications, (2007), pgs. 1003-1022; hereinafter “Babudri”), and Zhao et al. (CN 111808142 A; hereinafter “Zhao”) as applied to claim 1 above, and further in view of Bae (US 2016/0233440 A1).
Regarding claim 25, Tsai in view of Cai, Babudri, and Zhao teach LA1-1-9(LB28)2, as described above with respect to claim 1.
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LA1-1-9(LB28)2 fails to read on the claimed Formula 1 wherein at least one of X1 to X8 is CRx and Rx is cyano. However, Tsai teaches RC of Formula I may be a substituent including nitrile (¶ [0006] and [0043]).
Bae teaches cyano group substitutions on organometallic ligands, wherein by supplying a cyano group substitution to the ligand, the organometallic compound may have a deep HOMO energy level creating high triplet energy level due to an increased band gap resulting in a deep emission color (abstract; ¶ [0185]).
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 a cyano group on LA1-1-9(LB28)2, based on the teaching of Bae. The motivation for doing so would have been to provide a compound with deep HOMO energy level, high triplet energy level, and a deep emission color, as taught by Bae.
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 provide the cyano group in one of the locations corresponding to the claimed Rx, because it would have been choosing a specific location on LA1-1-9(LB28)2 for the position of the cyano group, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in the device of Tsai and possessing the benefits taught by Tsai and Bae. One of ordinary skill in the art would have been motivated to produce additional compounds comprising a ligand LA of Formula I having the benefits taught by Tsai 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 resulting modified compound reads on the claimed Formula 1 wherein at least one of X1 to X8 is CRx and Rx is cyano.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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.
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/BRAELYN R WATSON/Primary Examiner, Art Unit 1786
