DETAILED ACTION
Notice of Pre-AIA or AIA Status
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
2. Acknowledgment is made of applicant's claim for foreign priority based on an
application filed in Korea on November 11, 2022.
3. Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C.
119(a)-(d) prior to declaration of an interference, a certified English translation of the
foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and
41.202(e).
4. Failure to provide a certified translation may result in no benefit being accorded
for the non-English application.
Information Disclosure Statement
5. The references provided in the Information Disclosure Statement filed on July
31, 2023 have been considered. A signed copy of the corresponding 1449 form has
been included with this office action.
Claim Rejections - 35 USC § 103
6. 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.
7. 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.
8. 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.
9. 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.
10. Claims 13-16 and 21-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (KR 2021/0027179 A1 – English machine translation obtained from WIPO; hereinafter “Hatakeyama”) in view of Hashimoto et al. (US 2011/0127908 A1, hereinafter “Hashimoto”).
11. Regarding claims 13-16 and 21-22, Hatakeyama teaches fused polycyclic compounds represented by Formula (2) (Hatakeyama) (see structure below; end of pg. 2, beginning of pg. 3) wherein:
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R1 to R3, R4 to R7, R8 to R11, and R12 to R15 can be selected as hydrogen, deuterium, alkyl, and aryl (pg. 3); and
X1 can be selected as N–R wherein R can be a C6-C12 aryl group that is unsubstituted or substituted with C6-C12 aryl groups and C1-C6 alkyl groups (pg. 3); and
Z is represented by Formula Z1 (Hatakeyama):
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wherein “*” represents the point of attachment to ring d in Formula (2) (Hatakeyama) and Y can be an aryl group (pg. 3).
12. Hatakeyama teaches that introducing bulky substituents on the polycyclic compounds represented by Formula (2) (Hatakeyama), in the form of the ortho-substituent Z on the nitrogen atom of ring d, can suppress intermolecular interactions and minimize undesired fluorescence quenching (pg. 2: Solutions for Solving Problems).
13. Hatakeyama teaches that, as a consequence of the increased steric bulk, polycyclic compounds represented by Formula (2) (Hatakeyama) are useful dopant materials in organic light emitting elements, even when used in higher concentrations, resulting in advantages during the device manufacturing process (pg. 6: Effects of the Invention).
14. Hatakeyama specifically discloses the following compound D-66 (Hatakeyama) (see structure below, pg. 36)
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15. Compound D-66 (Hatakeyama) fails to read on all of the limitations of Formula 1 per claim 13 in that the tBu-substituted phenyl group (indicated with a circle) is not the terphenyl required by Formula 1.
16. However, 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 tBu-substituted phenyl group (indicated with a circle) in compound D-66 (Hatakeyama) with the terphenyl group on the other nitrogen atom of compound D-66 (Hatakeyama), based on the teaching of Hatakeyama. The motivation for doing so would have been to introduce an additional bulky substituent on the polycyclic compound to suppress intermolecular interactions and minimize undesired fluorescence quenching (pg. 2: Solutions for Solving Problems), as taught by Hatakeyama.
17. The modified structure of compound D-66 (Hatakeyama) resulting from this substitution is shown below.
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18. Modified D-66 (Hatakeyama) fails to read on all of the limitations of Formula 1 per claim 13 in that the tBu-groups (indicated with circles) are not the substituted or unsubstituted aryl amine groups, substituted or unsubstituted C6-C60 aryl groups, or substituted or unsubstituted C2-C60 heteroaryl groups as required by Formula 1.
19. Hashimoto teaches a fused polycyclic compound represented by Formula [1] (Hashimoto) that comprises at least one substituted or unsubstituted phenyl group represented by Formula [2] (Hashimoto) as a substituent along the planarized periphery of Formula [1] (Hashimoto) ([Abstract], see Formulae [1] and [2] below).
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20. Hashimoto teaches that introducing phenyl groups, defined by Formula [2] (Hashimoto) along the planarized periphery of Formula [1] (Hashimoto) are strongly affected by steric repulsion of substituents or hydrogen atoms on the both Formulae [1] and [2] (¶ [0033]). Consequently, Hashimoto teaches that the phenyl substituent defined by Formula [2] (Hashimoto) is oriented in such a manner that the plane including the
introduced substituent in Formula [2] (Hashimoto) is nearly perpendicular to the plane including the fused polycyclic ring skeleton represented by Formula [1] (Hashimoto) (¶ [0033]).
21. Hashimoto further teaches that this nearly perpendicular orientation of the planar structures of Formulae [1] and [2] inhibit the capacity of the overall structure to stack upon itself (¶ [0034]), which achieves:
lower crystallinity, improved stability in organic thin films, and suppression of degradation (¶ [0035]); and
suppression of concentration quenching, which improves emission efficiency and color purity (¶ [0036]); and
reduced sublimation temperature, which facilitates purification by sublimation and enables device fabrication via vacuum deposition (¶ [0037]).
22. 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 tBu groups (indicated with circles) in Modified D-66 (Hatakeyama) with the phenyl groups based on the teaching of Hashimoto. The motivation for doing so would have been to introduce a phenyl substituent that is nearly perpendicular to the plane of the fused polycyclic ring skeleton of Modified D-66 to:
lower crystallinity (¶ [0035]); and
suppress concentration quenching (¶ [0036]); and
reduce sublimation temperature (¶ [0037]),
as taught by Hashimoto.
23. The modified structure of Modified D-66 (Hatakeyama) resulting from these substitutions, motivated by Hashimoto, is shown below.
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24. Per claim 13, compound Modified D-66 (Hatakeyama, Hashimoto) reads on all of the limitations of Formula 1 wherein:
R1 is an unsubstituted C4 alkyl group; and
m1 to m2 are integers equal to one, m3 to m4 are integers equal to four, and m5 to m6 are integers equal to five; and
Rb1 to Rb2 are unsubstituted C4 alkyl groups, Rb3 to Rb6 are all hydrogen atoms; and
Ra3 and Ra6 are unsubstituted C6 aryl groups; and
Ra1, Ra2, Ra4, Ra5, Ra7, and Ra8 are all hydrogen atoms.
25. Per claim 14, compound Modified D-66 (Hatakeyama, Hashimoto) reads on all of the limitations of Formula 1-3 wherein:
R1, m1 to m6, and Rb1 to Rb6 are the same as previously defined; and
Ra31 and Ra61 are each independently unsubstituted C6 aryl groups.
26. Per claim 15, compound Modified D-66 (Hatakeyama, Hashimoto) reads on all of the limitations of Formula 1-3 wherein:
Ra31 and Ra61 are each independently unsubstituted phenyl groups.
27. Per claim 16, compound Modified D-66 (Hatakeyama, Hashimoto) reads on all of the limitations of Formula 1-3 wherein:
Ra31 and Ra61 are each independently represented by
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; and
R61 to R65 are all hydrogen atoms.
28. Per claim 21, compound Modified D-66 (Hatakeyama, Hashimoto) reads on the limitation wherein R1 is an unsubstituted t-butyl group.
29. Per claim 22, compound Modified D-66 (Hatakeyama, Hashimoto) reads on the limitation wherein R1 is
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.
30. Claim 23 is rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (KR 2021/0027179 A1 – English machine translation obtained from WIPO; hereinafter “Hatakeyama”) in view of Hashimoto et al. (US 2011/0127908 A1, hereinafter “Hashimoto”) as applied to claim 13 above, and in further view of Li et al. (US 2002/0076576 A1, hereinafter “Li”).
31. Regarding claim 23, compound Modified D-66 (Hatakeyama, Hashimoto) fails to read on the limitation wherein at least one of Ra1 to Ra8, as per Formula 1 of claim 13, comprises a deuterium atom or a substituent comprising a deuterium atom (see positions circled below).
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32. Hatakeyama does disclose the following compound D-24 (see below, pg. 32) wherein positions Ra1, Ra2, Ra4, Ra5, Ra7, and Ra8 (as per Formula 1 of claim 13) are all deuterium atoms, demonstrating that substituting hydrogen atoms for deuterium atoms at those positions is a known modification of Hatakeyama previously contemplated.
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33. Li teaches that carbon-deuterium bonds are stronger, more stable, and react more slowly than carbon-hydrogen bonds, which contributes to better thermal stability and longer organic light emitting device lifetimes (¶ [0009]).
34. Li fails to teach a specific site for deuterium incorporation, but does broadly teach the benefits of the carbon-deuterium bond compared to the carbon-hydrogen bond.
35. Therefore, given compound D-24 (Hatakeyama), Formula (2) (Hatakeyama), and the teachings of Li, 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 atoms in positions Ra1, Ra2, Ra4, Ra5, Ra7, and Ra8 (as per Formula 1 of claim 13) in compound Modified D-66 (Hatakeyama, Hashimoto), based on the teaching of Hatakeyama and Li. The motivation for doing so would have been to incorporate carbon-deuterium bonds that are stronger, more stable, and react more slowly than carbon-hydrogen bonds, which contributes to better thermal stability and longer organic light emitting device lifetimes (¶ [0009]), as taught by Li.
36. The modified structure of Modified D-66 (Hatakeyama, Hashimoto) resulting from these substitutions, motivated by Li, is shown below.
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37. Per claim 23, compound Modified D-66 (Hatakeyama, Hashimoto, Li) reads on the limitation wherein:
Ra1, Ra2, Ra4, Ra5, Ra7, and Ra8 are all deuterium atoms.
38. Claims 17-20 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (KR 2021/0027179 A1 – English machine translation obtained from WIPO; hereinafter “Hatakeyama”) in view of Hashimoto et al. (US 2011/0127908 A1, hereinafter “Hashimoto”) as applied to claim 13 above, and in further view of Geum et al. (US 2021/0277026 A1, hereinafter “Geum”).
39. Regarding claims 17-20 and 24, compound Modified D-66 (Hatakeyama, Hashimoto) fails to read on all of the limitations of Formula 1-A, specifically wherein Rb11 and Rb21 are not substituted or unsubstituted C1-C20 alkyl groups or substituted or unsubstituted C6-C20 aryl groups as required (positions for Rb11 and Rb21 are indicated with circles in the structure below).
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40. Hatakeyama does teach, however, that in Formula (2) (Hatakeyama):
R12 to R15 can be selected as hydrogen, deuterium, alkyl, and aryl (pg. 3); and
X1 can be selected as N–R wherein R can be a C6-C12 aryl group that is unsubstituted or substituted with C6-C12 aryl groups and C1-C6 alkyl groups (pg. 3).
41. Geum teaches polycyclic compounds represented by Formula 1 (Geum) (¶ [0042]-[0045]) wherein:
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n1 and n2 are each integers from zero to two (¶ [0045]); and
when Z1 to Z4 are each C–H then n1 + n2 = an integer from two to four (¶ [0045]); and
R1 to R9 can be substituted or unsubstituted alkyl groups and substituted or unsubstituted aryl groups (¶ [0043]).
42. Geum teaches that compounds represented by Formula 1 (Geum) have structural features, such as the ortho substituents on the phenyl groups bonded to the N atom of the polycycle (circled above), that confer increased steric encumbrance and thereby improve service lifetimes of organic light emitting elements by minimizing intermolecular interactions (¶ [0038]-[0039]).
43. Geum also teaches that compounds represented by Formula 1 (Geum) have improved thermal and chemical stability due to the increased steric encumbrance conferred by the bulky ortho substituents on the phenyl groups bonded to the nitrogen atom of the polycycle (circled above, ¶ [0038]-[0039]). Geum also discloses the compound shown below as an example of a dopant represented by Formula 1 (see below, [0188], pg 25) wherein the additional phenyl substituent is indicated with a circle.
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44. 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 atoms indicated with circles in compound Modified D-66 (Hatakeyama, Hashimoto), based on the teachings of Hatakeyama and Geum, and exemplified with the compound of Geum shown above. The motivation for doing so would have been to increase the steric bulk of the polycyclic compound by introducing an additional bulky phenyl substituent at the ortho position with respect to the nitrogen atoms to improve thermal and chemical stability (¶ [0038]-[0039]), as taught by Geum.
45. The modified structure of Modified D-66 (Hatakeyama, Hashimoto) resulting from these substitutions, motivated by Geum, is shown below.
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46. Per claim 17, compound Modified D-66 (Hatakeyama, Hashimoto, Geum) reads on all of the limitations of Formula 1-A wherein:
Rb11 and Rb21 are unsubstituted C6 aryl groups; and
Rb12 and Rb22 are unsubstituted C4 alkyl groups; and
Ra1 to Ra8, R1, m3 to m6, and Rb3 to Rb6 are the same as previously defined.
47. Per claim 18, compound Modified D-66 (Hatakeyama, Hashimoto, Geum) reads on all of the limitations of Formula 1-A wherein:
Rb11 and Rb21 are each unsubstituted phenyl groups; and
Rb12 and Rb22 are each unsubstituted t-butyl groups.
48. Per claim 19, compound Modified D-66 (Hatakeyama, Hashimoto, Geum) reads on all of the limitations of Formula 1-A1 wherein:
Ra1 to Ra8, R1, m5, m6, Rb5, Rb6, Rb11, Rb21, Rb12, Rb22 are the same as previously defined
49. Per claim 20, compound Modified D-66 (Hatakeyama, Hashimoto, Geum) reads on all of the limitations of Formula 1-A12 wherein:
Ra1 to Ra8, R1, m5, m6, Rb5, Rb6, Rb11, Rb21, Rb12, Rb22 are the same as previously defined
50. Per claim 24, compound Modified D-66 (Hatakeyama, Hashimoto, Geum) reads on the limitation wherein it is identical to compound 64.
51. Claims 1-4 and 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (KR 2021/0027179 A1 – English machine translation obtained from WIPO; hereinafter “Hatakeyama”) in view of Hashimoto et al. (US 2011/0127908 A1, hereinafter “Hashimoto”) and Kim et al. (US 2020/0235303 A1, hereinafter “Kim”).
52. Regarding claims 1-4 and 9-10, Hatakeyama teaches fused polycyclic compounds represented by Formula (2) (Hatakeyama) (see structure below; end of pg. 2, beginning of pg. 3) wherein:
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R1 to R3, R4 to R7, R8 to R11, and R12 to R15 can be selected as hydrogen, deuterium, alkyl, and aryl (pg. 3); and
X1 can be selected as N–R wherein R can be a C6-C12 aryl group that is unsubstituted or substituted with C6-C12 aryl groups and C1-C6 alkyl groups (pg. 3); and
Z is represented by Formula Z1 (Hatakeyama):
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wherein “*” represents the point of attachment to ring d in Formula (2) (Hatakeyama) and Y can be an aryl group (pg. 3).
53. Hatakeyama teaches that introducing bulky substituents on the polycyclic compounds represented by Formula (2) (Hatakeyama), in the form of the ortho-substituent Z on the nitrogen atom of ring d, can suppress intermolecular interactions and minimize undesired fluorescence quenching (pg. 2: Solutions for Solving Problems).
54. Hatakeyama teaches that, as a consequence of the increased steric bulk, polycyclic compounds represented by Formula (2) (Hatakeyama) are useful dopant materials in organic light emitting elements, even when used in higher concentrations, resulting in advantages during the device manufacturing process (pg. 6: Effects of the Invention).
55. Hatakeyama specifically discloses the following compound D-66 (Hatakeyama) (see structure below, pg. 36).
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56. Hatakeyama also teaches light emitting element (see Table 1, pg. 148-149) comprising:
a first electrode (ITO, anode, pg. 151); and
a second electrode (Al, cathode, pg. 151); and
an emission layer between the first and second electrode wherein the emission layer comprises a compound represented by Formula (2) (Hatakeyama) as a dopant material (pg. 151).
57. While Hatakeyama does not specifically teach compound D-66 (Hatakeyama) in an organic light emitting element, Hatakeyama does generally teach uses of compounds represented by Formula (2) (Hatakeyama) in organic light emitting elements of claim 1. At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to use compound D-66 (Hatakeyama) as the dopant material in a device having the structure taught by Hatakeyama above, because this would have been a combination of prior art elements according to known methods to yield predictable results and one of ordinary skill in the art would reasonably expect the modified organic light emitting elements to possess the benefits taught by Hatakeyama [suppressed intermolecular interactions and minimized undesired fluorescence quenching (pg. 2: Solutions for Solving Problems), and advantageous device manufacturing processes with higher dopant concentrations, (pg. 6: Effects of the Invention)]. See MPEP 2143(I)(A).
58. Compound D-66 (Hatakeyama) fails to read on all of the limitations of Formula 1 per claim 1 in that the tBu-substituted phenyl group (indicated with a circle) is not the terphenyl required by Formula 1.
59. However, 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 tBu-substituted phenyl group (indicated with a circle) in compound D-66 (Hatakeyama) with the terphenyl group on the other nitrogen atom of compound D-66 (Hatakeyama), based on the teaching of Hatakeyama. The motivation for doing so would have been to introduce an additional bulky substituent on the polycyclic compound to suppress intermolecular interactions and minimize undesired fluorescence quenching (pg. 2: Solutions for Solving Problems), as taught by Hatakeyama.
60. The modified structure of compound D-66 (Hatakeyama) resulting from this substitution is shown below.
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61. Modified D-66 (Hatakeyama) fails to read on all of the limitations of Formula 1 per claim 1 in that the tBu-groups (indicated with circles) are not the substituted or unsubstituted aryl amine groups, substituted or unsubstituted C6-C60 aryl groups, or substituted or unsubstituted C2-C60 heteroaryl groups as required by Formula 1.
62. Hashimoto teaches a fused polycyclic compound represented by Formula [1] (Hashimoto) that comprises at least one substituted or unsubstituted phenyl group represented by Formula [2] (Hashimoto) as a substituent along the planarized periphery of Formula [1] (Hashimoto) ([Abstract], see Formulae [1] and [2] below).
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63. Hashimoto teaches that introducing phenyl groups, defined by Formula [2] (Hashimoto) along the planarized periphery of Formula [1] (Hashimoto) are strongly affected by steric repulsion of substituents or hydrogen atoms on the both Formulae [1] and [2] (¶ [0033]). Consequently, Hashimoto teaches that the phenyl substituent defined by Formula [2] (Hashimoto) is oriented in such a manner that the plane including the
introduced substituent in Formula [2] (Hashimoto) is nearly perpendicular to the plane including the fused polycyclic ring skeleton represented by Formula [1] (Hashimoto) (¶ [0033]).
64. Hashimoto further teaches that this nearly perpendicular orientation of the planar structures of Formulae [1] and [2] inhibit the capacity of the overall structure to stack upon itself (¶ [0034]), which achieves:
lower crystallinity, improved stability in organic thin films, and suppression of degradation (¶ [0035]); and
suppression of concentration quenching, which improves emission efficiency and color purity (¶ [0036]); and
reduced sublimation temperature, which facilitates purification by sublimation and enables device fabrication via vacuum deposition (¶ [0037]).
65. 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 tBu groups (indicated with circles) in Modified D-66 (Hatakeyama) with the phenyl groups based on the teaching of Hashimoto. The motivation for doing so would have been to introduce a phenyl substituent that is nearly perpendicular to the plane of the fused polycyclic ring skeleton of Modified D-66 to:
lower crystallinity (¶ [0035]); and
suppress concentration quenching (¶ [0036]); and
reduce sublimation temperature (¶ [0037]),
as taught by Hashimoto.
66. The modified structure of Modified D-66 (Hatakeyama) resulting from these substitutions, motivated by Hashimoto, is shown below.
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67. The light emitting element of Hatakeyama, comprising the dopant Modified D-66 (Hatakeyama, Hashimoto) in the emission layer reads on all of the limitations of Formula 1 per claim 1, but fails to include at least one compound represented by Formula HT-1, Formula ET-1, and/or Formula M-b.
68. Hatakeyama does teach that the light emitting elements may include an emission layer comprising a host material and a dopant material of any combination (pg. 47).
69. Kim teaches a light emitting element comprising a first electrode, a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode wherein the interlayer comprises an emission layer (¶ [0395]-[0397], see also Table 1: Example 9).
70. The emission layer comprises a first host, a second host, and a dopant
(¶ [0395]-[0397], see also Table 1: Example 9), wherein the first host and the
second host are present at a ratio of 1:1 (¶ [0395]-[0397], see also Table 1: Example 9).
71. The dopant is a condensed polycyclic compound having a similar structure to the
compounds of Hatakeyama (¶ [0201] and [0395]-[0397]; Table 1: Example 9). The dopant of Hatakeyama has the structure that is encompassed by the structural formula of the light emitting dopant of Kim (¶ [0066]).
72. The first host comprises a hole-transporting host having the structure shown
below (¶ [0199] and [0395]-[0397] and Table 1: Example 9).
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73. The second host comprises an electron-transporting host having the structure
shown below (¶ [0200] and [0395]-[0397] and Table 1: Example 9)).
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74. Kim teaches that light emitting elements using the combination of the compounds
above taught by Kim possess high efficiency and long lifespan (¶ [0403]).
75. At the time the invention was effectively filed, it would have been obvious to one
of ordinary skill in the art to have modified the device taught by Hatakeyama by using the compounds of Kim described above as host materials, based on the teaching of Kim. The modification would have been a combination of prior art elements according to
known methods to yield predictable results. See MPEP 2143(I)(A). Furthermore, one of
ordinary skill in the art would have been motivated to select suitable and optimum
combinations of host materials to be used to make a light emitting elements in order to
produce optimal light emitting elements, which in this case means using the
combination of materials taught by Kim in order to provide devices with high efficiency
and long lifespan, as taught by Kim.
76. Per claim 1, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto) reads on all of the limitations of Formula 1 wherein:
R1 is an unsubstituted C4 alkyl group; and
m1 to m2 are integers equal to one, m3 to m4 are integers equal to four, and m5 to m6 are integers equal to five; and
Rb1 to Rb2 are unsubstituted C4 alkyl groups, Rb3 to Rb6 are all hydrogen atoms; and
Ra3 and Ra6 are unsubstituted C6 aryl groups; and
Ra1, Ra2, Ra4, Ra5, Ra7, and Ra8 are all hydrogen atoms.
77. Additionally, the modified light emitting element of Hatakeyama comprising the hole- and electron-transporting host materials of Kim reads on all of the limitations of Formula HT-1 and Formula ET-1 wherein:
in Formula HT-1, L1 is a direct linkage; and
X91 is CR103; and
R91 is a substituted C24 aryl group; and
R92 to R98 and R103 are all hydrogen atoms; and
in Formula ET-1, Y1 to Y3 are nitrogen atoms; and
L1 is an unsubstituted C6 arylene and n11 is an integer equal to one; and
L2 and L3 are direct linkages, and n12 and n13 are integers equal to one; and
Ar1 is a C18 aryl group, and Ar2 and Ar3 are C6 aryl groups.
78. Per claim 2, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto) as a dopant material and the hole- and electron-transporting host materials of Kim reads on all of the limitations of Formula 1-3 wherein:
R1, m1 to m6, and Rb1 to Rb6 are the same as previously defined; and
Ra31 and Ra61 are each independently unsubstituted C6 aryl groups.
79. Per claim 3, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto) as a dopant material and the hole- and electron-transporting host materials of Kim reads on all of the limitations of Formula 1-3 wherein:
Ra31 and Ra61 are each independently unsubstituted phenyl groups.
80. Per claim 4, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto) as a dopant material and the hole- and electron-transporting host materials of Kim reads on all of the limitations of Formula 1-3 wherein:
Ra31 and Ra61 are each independently represented by
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; and
R61 to R65 are all hydrogen atoms.
81. Per claim 9, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto) as a dopant material and the hole- and electron-transporting host materials of Kim reads on the limitation wherein R1 is an unsubstituted t-butyl group.
82. Per claim 10, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto) as a dopant material and the hole- and electron-transporting host materials of Kim reads on the limitation wherein R1 is
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.
83. Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (KR 2021/0027179 A1 – English machine translation obtained from WIPO; hereinafter “Hatakeyama”) in view of Hashimoto et al. (US 2011/0127908 A1, hereinafter “Hashimoto”) and Kim et al. (US 2020/0235303 A1, hereinafter “Kim”) as applied to claim 1 above, and in further view of Li et al. (US 2002/0076576 A1, hereinafter “Li”).
84. Regarding claim 11, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto) as a dopant material and the hole- and electron-transporting host materials of Kim fails to read on the limitation wherein at least one of Ra1 to Ra8, as per Formula 1 of claim 1, comprises a deuterium atom or a substituent comprising a deuterium atom (see positions circled below).
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85. Hatakeyama does disclose the following compound D-24 (see below, pg. 32) wherein positions Ra1, Ra2, Ra4, Ra5, Ra7, and Ra8 (as per Formula 1 of claim 13) are all deuterium atoms, demonstrating that substituting hydrogen atoms for deuterium atoms at those positions is a known modification of Hatakeyama previously contemplated.
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86. Li teaches that carbon-deuterium bonds are stronger, more stable, and react more slowly than carbon-hydrogen bonds, which contributes to better thermal stability and longer organic light emitting device lifetimes (¶ [0009]).
87. Li fails to teach a specific site for deuterium incorporation, but does broadly teach the benefits of the carbon-deuterium bond compared to the carbon-hydrogen bond.
88. Therefore, given compound D-24 (Hatakeyama), Formula (2) (Hatakeyama), and the teachings of Li, 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 atoms in positions Ra1, Ra2, Ra4, Ra5, Ra7, and Ra8 (as per Formula 1 of claim 13) in compound Modified D-66 (Hatakeyama, Hashimoto), based on the teaching of Hatakeyama and Li. The motivation for doing so would have been to incorporate carbon-deuterium bonds that are stronger, more stable, and react more slowly than carbon-hydrogen bonds, which contributes to better thermal stability and longer organic light emitting device lifetimes (¶ [0009]), as taught by Li.
89. The modified structure of Modified D-66 (Hatakeyama, Hashimoto) resulting from these substitutions, motivated by Li, is shown below.
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90. Per claim 23, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto, Li) as a dopant material and the hole- and electron-transporting host materials of Kim reads on the limitation wherein:
Ra1, Ra2, Ra4, Ra5, Ra7, and Ra8 are all deuterium atoms.
91. Claims 5-8 and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (KR 2021/0027179 A1 – English machine translation obtained from WIPO; hereinafter “Hatakeyama”) in view of Hashimoto et al. (US 2011/0127908 A1, hereinafter “Hashimoto”) and Kim et al. (US 2020/0235303 A1, hereinafter “Kim”) as applied to claim 1 above, and in further view of Geum et al. (US 2021/0277026 A1, hereinafter “Geum”).
92. Regarding claims 5-8 and 12, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto) as a dopant material and the hole- and electron-transporting host materials of Kim fails to read on all of the limitations of Formula 1-A, specifically wherein Rb11 and Rb21 are not substituted or unsubstituted C1-C20 alkyl groups or substituted or unsubstituted C6-C20 aryl groups as required (positions for Rb11 and Rb21 are indicated with circles in the structure below).
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93. Hatakeyama does teach, however, that in Formula (2) (Hatakeyama):
R12 to R15 can be selected as hydrogen, deuterium, alkyl, and aryl (pg. 3); and
X1 can be selected as N–R wherein R can be a C6-C12 aryl group that is unsubstituted or substituted with C6-C12 aryl groups and C1-C6 alkyl groups (pg. 3).
94. Geum teaches polycyclic compounds represented by Formula 1 (Geum) (¶ [0042]-[0045]) wherein:
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n1 and n2 are each integers from zero to two (¶ [0045]); and
when Z1 to Z4 are each C–H then n1 + n2 = an integer from two to four (¶ [0045]); and
R1 to R9 can be substituted or unsubstituted alkyl groups and substituted or unsubstituted aryl groups (¶ [0043]).
95. Geum teaches that compounds represented by Formula 1 (Geum) have structural features, such as the ortho substituents on the phenyl groups bonded to the N atom of the polycycle (circled above), that confer increased steric encumbrance and thereby improve service lifetimes of organic light emitting elements by minimizing intermolecular interactions (¶ [0038]-[0039]).
96. Geum also teaches that compounds represented by Formula 1 (Geum) have improved thermal and chemical stability due to the increased steric encumbrance conferred by the bulky ortho substituents on the phenyl groups bonded to the nitrogen atom of the polycycle (circled above, ¶ [0038]-[0039]). Geum also discloses the compound shown below as an example of a dopant represented by Formula 1 (see below, [0188], pg 25) wherein the additional phenyl substituent is indicated with a circle.
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97. 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 atoms indicated with circles in compound Modified D-66 (Hatakeyama, Hashimoto), based on the teachings of Hatakeyama and Geum, and exemplified with the compound of Geum shown above. The motivation for doing so would have been to increase the steric bulk of the polycyclic compound by introducing an additional bulky phenyl substituent at the ortho position with respect to the nitrogen atoms to improve thermal and chemical stability (¶ [0038]-[0039]), as taught by Geum.
98. The modified structure of Modified D-66 (Hatakeyama, Hashimoto) resulting from these substitutions, motivated by Geum, is shown below.
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99. Per claim 5, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto, Geum) as a dopant material and the hole- and electron-transporting host materials of Kim reads on all of the limitations of Formula 1-A wherein:
Rb11 and Rb21 are unsubstituted C6 aryl groups; and
Rb12 and Rb22 are unsubstituted C4 alkyl groups; and
Ra1 to Ra8, R1, m3 to m6, and Rb3 to Rb6 are the same as previously defined.
100. Per claim 6, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto, Geum) as a dopant material and the hole- and electron-transporting host materials of Kim reads on all of the limitations of Formula 1-A wherein:
Rb11 and Rb21 are each unsubstituted phenyl groups; and
Rb12 and Rb22 are each unsubstituted t-butyl groups.
101. Per claim 19, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto, Geum) as a dopant material and the hole- and electron-transporting host materials of Kim reads on all of the limitations of Formula 1-A1 wherein:
Ra1 to Ra8, R1, m5, m6, Rb5, Rb6, Rb11, Rb21, Rb12, Rb22 are the same as previously defined
102. Per claim 20, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto, Geum) as a dopant material and the hole- and electron-transporting host materials of Kim reads on all of the limitations of Formula 1-A12 wherein:
Ra1 to Ra8, R1, m5, m6, Rb5, Rb6, Rb11, Rb21, Rb12, Rb22 are the same as previously defined
103. Per claim 24, the modified light emitting element of Hatakeyama comprising compound Modified D-66 (Hatakeyama, Hashimoto, Geum) as a dopant material and the hole- and electron-transporting host materials of Kim reads on the limitation wherein it is identical to compound 64.
Conclusion
104. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Brandon J. Cooper whose telephone number is (571)272-0005. The examiner can normally be reached Monday - Friday 7:30 AM - 5:00 PM.
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/B.J.C./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
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