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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 05/11/2026 has been entered.
Terminal Disclaimer
The terminal disclaimer filed on 12/22/2025 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of Application 17/771,743 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Response to Amendment
The amendment of 05/11/2026 has been entered.
Disposition of claims:
Claim 5 has been canceled.
Claim 11 has been added.
Claims 1-4 and 6-11are pending.
Claims 1 and 4 have been amended.
Response to Arguments
Applicant’s arguments see page 23-34 of the reply filed 05/11/2026 regarding The rejections of claims 1-4 and 6-10 under 35 U.S.C. 103 as being unpatentable over Mun et al. (US 2019/0296248 A1, hereafter Mun) in view of Hyun et al. (KR 2018/0063707 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent, hereafter Hyun) set forth in the Office Action of 02/12/2026 have been considered.
Applicant argues that by this amendment, a direct bond has been deleted from the definition of L1; accordingly the Ar1 group is now required to be connected to the core structure through an arylene or heteroarylene linker such that the rejections need to be withdrawn (page 23-25).
Respectfully, the Examiner does not agree.
It is acknowledged that L1 is now required to be an arylene or heteroarylene linker; however, the variable a of the (L1)a can be zero; thus, the structure represented by (L1)a of the Formula 1 of the amended claims can be a direct bond. The Compound of Lee as modified by Hyun (see section 51 of the last Office Action) still reads on all the limitation of Applicant’s Formula 1 of the amended claims.
For at least the reason above, the arguments are not found persuasive. The rejections are maintained.
Applicant argues that there is no motivation to combine Mun and Hyun because Mun discloses the use of the compound in combination with other compounds in EML whereas Hyun discloses use of the compound alone in EBL (page 25-27).
Respectfully, the Examiner does not agree.
Hyun does not require the compound of Hyun to be used EBL. Hyun discloses that the organic layer of the organic light emitting device of Hyun can include HIL, HTL, EBL, HBL, EML, ETL, and EIL, wherein at least one layer includes the compound of Hyun ([0058]-[0059]). Hyun teaches the advantages of the compound represented by the Formula 1 of Hyun, wherein the compound provides excellent luminous efficiency and quantum efficiency when it is used in an organic light emitting device ([0005]-[0006]). Thus, an ordinary skill in the art would have modified the compound of Moon in view of Hyun, because the advantages that Hyun teaches can be applied to the EML material of Mun (Compound 1-44 of Mun).
For at least the reason above, the arguments are not found persuasive. The rejections are maintained.
Applicant argues that the broad disclosure of Mun does not provide a specific motivation to select the particular substitution position of the claimed invention (page 26).
Respectfully, the Examiner does not agree.
Mun discloses an organic light emitting device comprising a light emitting layer containing a first host of Formula (1) and a second host of Formula (2) ([0020]).
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Compound 1-44 of Mun has similar structure as Applicant’s Chemical Formula 1. The only difference is that the substitution positions of the carbazolyl group and the bis(biphenyl)amine group. The Compound 1-44 of Mun has the carbazolyl group substituted to the position 1 and the bis(biphenyl)amine group substituted to the position 4 of the dibenzofuran group (see the annotated numbers in the figure above), while Applicant’s Chemical Formula 1 requires the carbazolyl group substituted to the position 3 and the bis(biphenyl)amine group substituted to the position 1.
However, Mun does teach that the substituent groups corresponding to the (Ar1-L1)(Ar2-L2)N- and (Ar3-L3)(Ar4-L4)N- can be substituted to any substitutable positions of the dibenzofuran group corresponding to the L5 of Formula (1) ([0067]).
Hyun discloses a compound (Formula I) used as the organic material layer of an organic light emitting device ([0011]). Hyun teaches that the compound of Hyun can be used to make any organic layer including the light emitting layer of the organic light emitting device ([0005]-[0011], [0058]-[0059]). Thus, Mun and Hyun are in the same art area.
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The compound of Hyun which is represented by Formula I in the figure above, has a dibenzofuran core wherein the position 1 of the dibenzofuran is substituted by an amine group and the position 3 of the dibenzofuran can be substituted by a heteroaryl group ([0006]-[0009], [0017]-[0020]). Thus, an ordinary skill in the art would have known that the Compound 1-44 of Mun would be encompassed by the Formula I of Hyun if the bis(biphenyl)amine and carbazolyl groups are substituted to the positions 1 and 3, respectively.
Hyun teaches that the compound of Hyun provides the organic light emitting device comprising the compound with excellent luminescent efficiency and quantum efficiency ([0005]).
Thus, it would have been obvious to one of ordinary skill in the art to have modified the Compound 1-44 of Mun by substituting the substitution position of the carbazolyl group from position 1 to position 3 and the substitution position of the bis(biphenyl)amine group from position 4 to position 1 of the dibenzofuran group, as taught by Mun and Hyun.
Applicant argues that the Examiner’s reasoning is based on impermissible hindsight (page 27).
Respectfully, the Examiner does not agree.
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. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
For at least the reason above, the arguments are not found persuasive. The rejections are maintained.
Applicant argues that the compounds of the claimed invention exhibit unexpected and superior device performance compared to the compounds disclosed in Mun and Hyun (page 27-31).
Respectfully, the Examiner does not agree.
It is unclear if the results are unexpected. It cannot be determined that the results are unexpected for at least the following reasons.
First, Applicant shows new data including additional comparative examples 1-5; however, the data was not been properly entered using an affidavit or declaration under 37 CFR 1.132.
An affidavit or declaration under 37 CFR 1.132 must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness. In re Burckel, 592 F.2d 1175, 201 USPQ 67 (CCPA 1979). "A comparison of the claimed invention with the disclosure of each cited reference to determine the number of claim limitations in common with each reference, bearing in mind the relative importance of particular limitations, will usually yield the closest single prior art reference." In re Merchant, 575 F.2d 865, 868, 197 USPQ 785, 787 (CCPA 1978) (emphasis in original). Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, In re Finley, 174 F.2d 130, 81 USPQ 383 (CCPA 1949), and if not explained should be noted and evaluated, and if significant, explanation should be required. In re Armstrong, 280 F.2d 132, 126 USPQ 281 (CCPA 1960) (deviations from example were inconsequential). See MPEP 716.02(e).
Thus, the new data was not entered property such that the data cannot be considered.
The Examiner provides the following reasons on the assumption that the new data was properly entered.
Secondly, each of the additional comparative examples 1 to 3 in Table 2 is not the closest prior art because the closest prior art (i.e. the organic light emitting device of Moon) requires the light emitting layer to include a first host of Formula (1) of Moon and a second host of Formula (2) of Moon; on the other hand, each of the additional comparative examples 1 and 3 includes only one of Formulas (1) and (2) of Moon.
Third, in response to Applicant’s arguments that the additional comparative example 4 has lower driving voltage, higher efficiency, and longer lifetime as compared to the additional comparative example 5 (Table 3), the Examiner’s response is as follows. There are multiple differences between the additional comparative examples and 4 and 5. The comparative Compound N differs from the inventive Compound 214 in that the substitution positions of the carbazole and amine groups (difference no. 1), the structure of the linker group of (L1)a of Applicant’s Chemical Formula A (difference no. 2), and the structure of the terminal group Ar11 (or Ar12) of Applicant’s Chemical Formula A (difference no. 3). Because of the multiple differences, a direct comparison between the two devices cannot be made. That is to say, an extent that the effect of the modification at issue (i.e. the change of the substitution positions of the carbazole and amine groups) cannot be isolated. Accordingly, it is unclear to what degree the change of the substitution positions of the carbazole and the amine groups alone causes changes the properties of the organic light emitting devices including driving voltage, efficiency, and lifetime.
Additionally, the instant claims do not require the amine group of Applicant’s Chemical Formula A to be
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of the Applicant’s Compound 214. The results are not commensurate in scope with the claims.
With respect to the commensurate in scope with claimed invention, the Examiner points out MPEP 716.02(d), as recited below.
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range.
In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980) (Claims were directed to a process for removing corrosion at "elevated temperatures" using a certain ion exchange resin (with the exception of claim 8 which recited a temperature in excess of 100C). Appellant demonstrated unexpected results via comparative tests with the prior art ion exchange resin at 110C and 130C. The court affirmed the rejection of claims 1-7 and 9-10 because the term "elevated temperatures" encompassed temperatures as low as 60C where the prior art ion exchange resin was known to perform well. The rejection of claim 8, directed to a temperature in excess of 100C, was reversed.). See also In re Peterson, 315 F.3d 1325, 1329-31, 65 USPQ2d 1379, 1382-85 (Fed. Cir. 2003) (data showing improved alloy strength with the addition of 2% rhenium did not evidence unexpected results for the entire claimed range of about 1-3% rhenium); In re Grasselli, 713 F.2d 731, 741, 218 USPQ 769, 777 (Fed. Cir. 1983) (Claims were directed to certain catalysts containing an alkali metal. Evidence presented to rebut an obviousness rejection compared catalysts containing sodium with the prior art. The court held this evidence insufficient to rebut the prima facie case because experiments limited to sodium were not commensurate in scope with the claims.).
Fourth, in response to applicant's argument as described above, the fact that applicant has recognized another advantage (i.e. low driving voltage, high efficiency, and longer lifetime) which would flow naturally from following the suggestion of the prior art (i.e. excellent luminescent efficiency and quantum efficiency taught by Hyun ([0005])) cannot be the basis for patentability when the differences would otherwise be obvious. See Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985).
For at least the reason above, the arguments are not found persuasive. The rejections are maintained.
Applicant argues that the rejection of claim 4 should be withdrawn (page 31-34).
The Examiner does not agree all the arguments that Applicant makes (page 31-34); however, the Compound of Lee as modified by Hyun (section 51 of the last Office Action) that the previous rejections relies on, does not read on the limitation of the amended claim 4 because the Chemical Formula 4 has been deleted. For that reason, the rejection has been withdrawn.
However, Mun in view of Hyun is applicable to make new grounds of rejection to claim 4.
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As outlined in the previous Office Action, Lee in view of Hyun teaches the Compound of Lee as modified by Hyun (see sections 40-57).
In the compound, the substituent of the position-3 of the benzene ring of the carbazole group at the position corresponding to Ar1 of Formula (1) of Mun is unsubstituted (see the arrow in the figure above); however, Mun does teach that the benzene ring corresponding to the Ar1 of Formula (1) of Mun can be a substituted by a C6 aryl group (item 7 in [0067]) and exemplifies an unsubstituted phenyl group (i.e. the part enclosed by a dashed circle in the figure below) as the substituent of the ring Ar1 of Formula (1) ([0096] including at least Compound 1-32).
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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 Compound of Mun as modified by Hyun by substituting the hydrogen atom substituted at the position-3 of the benzene ring at the position corresponding to Ar1 of Formula (1) of Mun with an unsubstituted phenyl group, as taught by Mun.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the exemplified substituent groups from hydrogen to an unsubstituted phenyl in the ring Ar1 of the Formula (1) of Mun would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Mun as modified by Hyun (2).
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A new ground of rejection is applied.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-3 and 7-10 are rejected under 35 U.S.C. 103 as being unpatentable over Mun et al. (US 2019/0296248 A1, hereafter Mun) in view of Hyun et al. (KR 2018/0063707 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent, hereafter Hyun).
Regarding claim 1-3, Mun discloses an organic light emitting device comprising a light emitting layer containing a first host of Formula (1) and a second host of Formula (2) ([0020]).
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Compound 1-44 of Mun has similar structure as Applicant’s Chemical Formula 1. The only difference is that the substitution positions of the carbazolyl group and the bis(biphenyl)amine group. The Compound 1-44 of Mun has the carbazolyl group substituted to the position 1 and the bis(biphenyl)amine group substituted to the position 4 of the dibenzofuran group (see the annotated numbers in the figure above), while Applicant’s Chemical Formula 1 requires the carbazolyl group substituted to the position 3 and the bis(biphenyl)amine group substituted to the position 1.
However, Mun does teach that the substituent groups corresponding to the (Ar1-L1)(Ar2-L2)N- and (Ar3-L3)(Ar4-L4)N- can be substituted to any substitutable positions of the dibenzofuran group corresponding to the L5 of Formula (1) ([0067]).
Hyun discloses a compound (Formula I) used as the organic material layer of an organic light emitting device ([0011]). Hyun teaches that the compound of Hyun can be used to make any organic layer including the light emitting layer of the organic light emitting device ([0005]-[0011], [0058]-[0059]).
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The compound of Hyun which is represented by Formula I of Hyun, has a dibenzofuran core (i.e. X is O), wherein the position 1 of the dibenzofuran is substituted by an amine group and the position 3 of the dibenzofuran can be substituted by a heteroaryl group ([0006]-[0009], [0017]-[0020]). Thus, an ordinary skill in the art would know that the Compound 1-44 of Mun would be encompassed by the Formula I of Hyun, if the bis(biphenyl)amine and carbazolyl groups are substituted to the positions 1 and 3, respectively.
Hyun teaches that the compound of Hyun provides the organic light emitting device comprising the compound with excellent luminescent efficiency and quantum efficiency ([0005]).
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 Compound 1-44 of Mun by substituting the substitution position of the carbazolyl group from position 1 to position 3 and the substitution position of the bis(biphenyl)amine group from position 4 to position 1 of the dibenzofuran group, as taught by Mun and Hyun.
The motivation of doing so would have been to provide the organic light emitting device comprising the compound with excellent luminescent efficiency and quantum efficiency based on the teaching of Hyun.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Mun teaches that the substituent groups corresponding to the (Ar1-L1)(Ar2-L2)N- and (Ar3-L3)(Ar4-L4)N- can be substituted to any substitutable positions of the dibenzofuran group corresponding to the L5 of Formula 1 ([0067]). Each substitution of the substitution positions of the carbazolyl group and the bis(biphenyl)amine group would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Mun as modified by Hyun which has identical structure as Applicant’s Chemical Formula 1, wherein L1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and a is 0.
Regarding claims 7-10, the Compound of Mun as modified by Hyun reads on all the features of claim 1 as outlined above.
Mun in view of Hyun does not disclose a specific organic light emitting device comprising the Compound of Mun as modified by Hyun, however, Mun does teach that the compound of Mun represented by Formula (1) of Mun can be used as the host of the light emitting layer of an organic light emitting device ([0020]).
Mun teaches the structure of an organic light emitting device comprising a first electrode, a hole injection layer, a light emitting layer (a compound of Formula (1) of Mun as a first host, a compound of Formula (2) of Mun as a second host, and a light emitting dopant), an electron injection layer, and a second electrode ([0364]-[0367]).
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 Compound of Mun as modified by Hyun by incorporating it as the host compound of an organic light emitting device, as taught by Mun.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the host compounds of Mun in an organic light emitting device of Mun would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Mun as modified by Hyun comprising a first electrode, a hole injection layer, a light emitting layer (Compound of Mun as modified by Hyun as a first host, a compound of Formula (2) of Mun as a second host, and a light emitting dopant), an electron injection layer, and a second electrode.
Claims 4 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Mun et al. (US 2019/0296248 A1) in view of Hyun et al. (KR 2018/0063707 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent) as applied to claims 1-3 and 7-10 above, further in view of Kitamura et al. (US 2012/0298977 A1, hereafter Kitamura).
Regarding claim 4, the Compound of Mun as modified by Hyun reads on all the features of claim 1 as outlined above.
In the compound, the substituent of the position-3 of the benzene ring of the carbazole group at the position corresponding to Ar1 of Formula (1) of Mun is unsubstituted (see the arrow in the figure above); however, Mun does teach that the benzene ring corresponding to the Ar1 of Formula (1) of Mun can be a substituted by a C6 aryl group (item 7 in [0067]) and exemplifies an unsubstituted phenyl group (i.e. the part enclosed by a dashed circle in the figure below) as the substituent of the ring Ar1 of Formula (1) ([0096] including at least Compound 1-32).
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Kitamura discloses a carbazole compound used for an organic light emitting device ([0001], [0023]).
Kitamura teaches that introduction of a substituent to the 3-position of carbazole provides easiness of synthesis and improved chemical stability ([0093]).
Kitamura exemplifies a carbazole compound wherein the 3-position is substituted by an unsubstituted phenyl group (see Compound A-10 in [0122]).
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 Compound of Mun as modified by Hyun by substituting the hydrogen atom substituted at the position-3 of the benzene ring at the position corresponding to Ar1 of Formula (1) of Mun with an unsubstituted phenyl group, as taught by Mun and Kitamura.
The motivation of doing so would have been to provide easiness of synthesis and improved chemical stability, based on the teaching of Kitamura.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the exemplified substituents from hydrogen to an unsubstituted phenyl at position-3 of the carbazole of the ring Ar1 of the Formula (1) of Mun would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Mun as modified by Hyun and Kitamura.
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Regarding claim 11, the Compound of Mun as modified by Hyun and Kitamura reads on all the features of claim 4 as outlined above.
The Compound of Mun as modified by Hyun and Kitamura has similar structure as Applicant’s Compound 212. The only difference is that the phenyl group at the position corresponding to Ar3 of Formula (1) of Mun is substituted to the meta position of the linker L3 (see the annotation in the figure above), whine Applicant’s Compound 212 requires the phenyl group to be substituted to the para position of the linker L3. However, Mun does teach that the Ar3 can be substituted any of ortho, meta, and para position of the linker L3 (see Formula (A-1) in [0071]) and exemplifies specific embodiments, wherein the ring Ar3 is substituted to the para position of the linker L3 ([0096], see at least Compound 1-3).
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 Compound of Mun as modified by Hyun and Kitamura by substituting the substitution position of the phenyl group at the position corresponding to Ar3 of Formula (1) of Mun from meta position of the linker L3 to the para position of the linker L3, as taught by Mun.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the substitution position of the ring Ar3 in the linker L3 of the Formula (1) of Mun would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of substitution position in the linker L3. The selection of para linking would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
Additionally, a compound having a terminal phenyl group is substituted to the para position of the linker phenylene group is a position isomer of the Compound of Mun as modified by Hyun and Kitamura.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Therefore, at the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to modify Compound of Mun as modified by Hyun and Kitamura such that the terminal phenyl group at Ar3 is substituted to the para position of the linker phenylene group at L3. A compound in which the terminal phenyl group at Ar3 is substituted to the para position of the linker phenylene group at L3 would represent a position isomer of the Compound of Mun as modified by Hyun and Kitamura. One of ordinary skill in the art would expect that the position isomers having each respective structure would act in similar manner.
The modification provides Compound of Mun as modified by Hyun and Kitamura (2) which has identical structure as Applicant’s Compound 212.
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Claims 1-3 and 7-10 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US 2019/0189927 A1, hereafter Lee) in view of Hyun et al. (KR 2018/0063707 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent).
Regarding claim 1-3, Lee discloses an organic light emitting device comprising a light emitting layer containing a first host of Formula (1) and a second host of Formula (2) ([0027]).
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Compound 1-44 of Lee has similar structure as Applicant’s Chemical Formula 1. The only difference is that the substitution positions of the carbazolyl group and the bis(biphenyl)amine group. The Compound 1-44 of Lee has the carbazolyl group substituted to the position 1 and the bis(biphenyl)amine group substituted to the position 4 of the dibenzofuran group (see the annotated numbers in the figure above), while Applicant’s Chemical Formula 1 requires the carbazolyl group substituted to the position 3 and the bis(biphenyl)amine group substituted to the position 1.
However, Lee does teach that the substituent groups corresponding to the (Ar1-L1)(Ar2-L2)N- and (Ar3-L3)(Ar4-L4)N- can be substituted to any substitutable positions of the dibenzofuran group corresponding to the L5 of Formula (1) ([0063], [0068]).
Hyun discloses a compound (Formula I) used as the organic material layer of an organic light emitting device ([0011]). Hyun teaches that the compound of Hyun can be used to make any organic layer including the light emitting layer of the organic light emitting device ([0005]-[0011], [0058]-[0059]).
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The compound of Hyun which is represented by Formula I of Hyun, has a dibenzofuran core (i.e. X is O), wherein the position 1 of the dibenzofuran is substituted by an amine group and the position 3 of the dibenzofuran can be substituted by a heteroaryl group ([0006]-[0009], [0017]-[0020]). Thus, an ordinary skill in the art would know that the Compound 1-44 of Lee would be encompassed by the Formula I of Hyun, if the bis(biphenyl)amine and carbazolyl groups are substituted to the positions 1 and 3, respectively.
Hyun teaches that the compound of Hyun provides the organic light emitting device comprising the compound with excellent luminescent efficiency and quantum efficiency ([0005]).
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 Compound 1-44 of Lee by substituting the substitution position of the carbazolyl group from position 1 to position 3 and the substitution position of the bis(biphenyl)amine group from position 4 to position 1 of the dibenzofuran group, as taught by Lee and Hyun.
The motivation of doing so would have been to provide the organic light emitting device comprising the compound with excellent luminescent efficiency and quantum efficiency based on the teaching of Hyun.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Lee teaches that the substituent groups corresponding to the (Ar1-L1)(Ar2-L2)N- and (Ar3-L3)(Ar4-L4)N- can be substituted to any substitutable positions of the dibenzofuran group corresponding to the L5 of Formula 1 ([0063], [0068]). Each substitution of the substitution positions of the carbazolyl group and the bis(biphenyl)amine group would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Lee as modified by Hyun which has identical structure as Applicant’s Chemical Formula 1, wherein L1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and a is 0.
Regarding claims 7-10, the Compound of Lee as modified by Hyun reads on all the features of claim 1 as outlined above.
Lee in view of Hyun does not disclose a specific organic light emitting device comprising the Compound of Lee as modified by Hyun, however, Lee does teach that the compound of Lee represented by Formula (1) of Lee can be used as the host of the light emitting layer of an organic light emitting device ([0027]).
Lee teaches the structure of an organic light emitting device comprising a first electrode, a hole injection layer, a light emitting layer (a compound of Formula (1) of Lee as a first host, a compound of Formula (2) of Lee as a second host, and a light emitting dopant), an electron injection layer, and a second electrode ([0340]).
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 Compound of Lee as modified by Hyun by incorporating it as the host compound of an organic light emitting device, as taught by Lee.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the host compounds of Lee in an organic light emitting device of Lee would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Lee as modified by Hyun comprising a first electrode, a hole injection layer, a light emitting layer (Compound of Lee as modified by Hyun as a first host, a compound of Formula (2) of Lee as a second host, and a light emitting dopant), an electron injection layer, and a second electrode.
Claims 4 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US 2019/0189927 A1) in view of Hyun et al. (KR 2018/0063707 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent) as applied to claims 1-3 and 7-10 above, further in view of Kitamura et al. (US 2012/0298977 A1).
Regarding claim 4, the Compound of Lee as modified by Hyun reads on all the features of claim 1 as outlined above.
In the compound, the substituent of the position-3 of the benzene ring of the carbazole group at the position corresponding to Ar1 of Formula (1) of Lee is unsubstituted (see the arrow in the figure above); however, Lee does teach that the benzene ring corresponding to the Ar1 of Formula (1) of Lee can be a substituted by a C6 aryl group ([0073]) and exemplifies an unsubstituted phenyl group (i.e. the part enclosed by a dashed circle in the figure below) as the substituent of the ring Ar1 of Formula (1) ([0125] including at least Compound 1-32).
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Kitamura discloses a carbazole compound used for an organic light emitting device ([0001], [0023]).
Kitamura teaches that introduction of a substituent to the 3-position of carbazole provides easiness of synthesis and improved chemical stability ([0093]).
Kitamura exemplifies a carbazole compound wherein the 3-position is substituted by an unsubstituted phenyl group (see Compound A-10 in [0122]).
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 Compound of Lee as modified by Hyun by substituting the hydrogen atom substituted at the position-3 of the benzene ring at the position corresponding to Ar1 of Formula (1) of Lee with an unsubstituted phenyl group, as taught by Lee and Kitamura.
The motivation of doing so would have been to provide easiness of synthesis and improved chemical stability, based on the teaching of Kitamura.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the exemplified substituents from hydrogen to an unsubstituted phenyl at position-3 of the carbazole of the ring Ar1 of the Formula (1) of Lee would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Compound of Lee as modified by Hyun and Kitamura.
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Regarding claim 11, the Compound of Lee as modified by Hyun and Kitamura reads on all the features of claim 4 as outlined above.
The Compound of Lee as modified by Hyun and Kitamura has similar structure as Applicant’s Compound 212. The only difference is that the phenyl group at the position corresponding to Ar3 of Formula (1) of Lee is substituted to the meta position of the linker L3 (see the annotation in the figure above), whine Applicant’s Compound 212 requires the phenyl group to be substituted to the para position of the linker L3. However, Lee does teach that the Ar3 can be substituted any of ortho, meta, and para position of the linker L3 (see Formula (A-1) in [0071]) and exemplifies specific embodiments, wherein the ring Ar3 is substituted to the para position of the linker L3 ([0096], see at least Compound 1-3).
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 Compound of Lee as modified by Hyun and Kitamura by substituting the substitution position of the phenyl group at the position corresponding to Ar3 of Formula (1) of Lee from meta position of the linker L3 to the para position of the linker L3, as taught by Lee.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the substitution position of the ring Ar3 in the linker L3 of the Formula (1) of Lee would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). There are finite number of substitution position in the linker L3. The selection of para linking would have been one from a finite number of identified, predictable solutions, with a reasonable expectation of success. See MPEP 2143(I)(E).
Additionally, a compound having a terminal phenyl group is substituted to the para position of the linker phenylene group is a position isomer of the Compound of Lee as modified by Hyun and Kitamura.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Therefore, at the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to modify Compound of Lee as modified by Hyun and Kitamura such that the terminal phenyl group at Ar3 is substituted to the para position of the linker phenylene group at L3. A compound in which the terminal phenyl group at Ar3 is substituted to the para position of the linker phenylene group at L3 would represent a position isomer of the Compound of Lee as modified by Hyun and Kitamura. One of ordinary skill in the art would expect that the position isomers having each respective structure would act in similar manner.
The modification provides Compound of Lee as modified by Hyun and Kitamura (2) which has identical structure as Applicant’s Compound 212.
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Claims 1-3, 6-7, and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Chang et al. (KR 2017/0127353 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent, hereafter Chang) in view of Hyun et al. (KR 2018/0063707 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent).
Regarding claims 1-3, 6-7, and 10, Chang discloses a compound used as the hole transporting layer material, wherein the hole transport layer has a direct contact with the light emitting layer of an organic light emitting device ([0007]-[0008], Formula 1 in [00011]) and exemplifies Compound 7 ([0040]).
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Compound 7 of Chang has similar structure as Applicant’s Chemical Formula 1. The only difference is that the substitution positions of the carbazolyl group and the bis(biphenyl)amine group. The Compound 7 of Chang has the carbazolyl group substituted to the position 1 and the bis(biphenyl)amine group substituted to the position 3 of the dibenzofuran group (see the annotated numbers in the figure above), while Applicant’s Chemical Formula 1 requires the carbazolyl group substituted to the position 3 and the bis(biphenyl)amine group substituted to the position 1.
However, Chang does teach that the amine group can substituted to the position 1 of the dibenzofuran group, and the carbazolyl group can be substituted to the position 3 of the dibenzofuran group (see Formula 3 in [0026]-[0027] as shown below).
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Hyun discloses a compound (Formula I) used as the organic material layer of an organic light emitting device ([0011]). Hyun teaches that the compound of Hyun can be used to make any organic layer including the hole transport layer and electron blocking layer of the organic light emitting device ([0005]-[0011], [0058]-[0059], [0346]). Both Chang and Hyun are in the same art which is the electron blocking layer material of an organic light emitting device.
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The compound of Hyun which is represented by Formula I of Hyun, has a dibenzofuran core (i.e. X is O), wherein the position 1 of the dibenzofuran is substituted by an amine group and the position 3 of the dibenzofuran can be substituted by a heteroaryl group ([0006]-[0009], [0017]-[0020]). Thus, an ordinary skill in the art would know that the Compound 7 of Chang would be encompassed by the Formula I of Hyun, if the bis(biphenyl)amine and carbazolyl groups are substituted to the positions 1 and 3, respectively.
Hyun teaches that the compound of Hyun provides the organic light emitting device comprising the compound with excellent luminescent efficiency and quantum efficiency ([0005]).
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 Compound 7 of Chang by substituting the substitution position of the carbazolyl group from position 1 to position 3 and the substitution position of the bis(biphenyl)amine group from position 3 to position 1 of the dibenzofuran group, as taught by Lee and Hyun.
The motivation of doing so would have been to provide the organic light emitting device comprising the compound with excellent luminescent efficiency and quantum efficiency based on the teaching of Hyun.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Chang teaches that the amine group can substituted to the position 1 of the dibenzofuran group, and the carbazolyl group can be substituted to the position 3 of the dibenzofuran group (see Formula 3 in [0026]-[0027]). Each substitution of the substitution positions of the carbazolyl group and the bis(biphenyl)amine group would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
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The modification provides Compound of Chang as modified by Hyun, which has identical structure as Applicant’s Compound 216, meeting all the limitations of claims 1-3 and 6.
Chang in view of Hyun does not disclose a specific organic light emitting device comprising the Compound of Chang as modified by Hyun, however, Chang does teach that the compound of Chang can be used as the hole transport layer material which has a direct contact with the light emitting layer of an organic light emitting device ([0007]-[0008]).
Chang teaches the structure of an organic light emitting device comprising a first electrode, a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and a second electrode ([0431]-[0432]).
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 Compound of Chang as modified by Hyun by incorporating it as the hole transport layer material of an organic light emitting device, as taught by Chang.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the hole transport layer materials of an organic light emitting device of Chang would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Chang as modified by Hyun comprising a first electrode, a hole injection layer, a hole transport layer (Compound of Chang as modified by Hyun), a light emitting layer, an electron injection layer, and a second electrode, meeting all the limitations of claims 7 and 10.
Claims 8-9 are rejected under 35 U.S.C. 103 as being unpatentable over Chang et al. (KR 2017/0127353 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent) in view of Hyun et al. (KR 2018/0063707 A, the original document is referred to for figures and tables, the English translation is referred to for the remainder body of the patent) as applied to claims 1-3, 6-7, and 10 above, further in view of Lee et al. (US 2019/0189927 A1).
Regarding claims 8-9, the Compound of Chang as modified by Hyun reads on all the features of claim 1 as outlined above.
Chang in view of Hyun does not teach a specific organic light emitting device comprising the Compound of Chang as modified by Hyun as the host material of the light emitting layer.
Lee discloses an organic light emitting device comprising a light emitting layer containing a first host of Formula (1) and a second host of Formula (2) ([0027]).
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The Compound of Chang as modified by Hyun is encompassed by the Formula (1) of Lee.
Lee teaches that the organic light emitting device of Mun provides controlling charge balance, low driving voltage, improved efficiency and life span ([0025], [0029]).
Lee teaches the structure of an organic light emitting device comprising a first electrode, a hole injection layer, a light emitting layer (a compound of Formula (1) of Mun as a first host, a compound of Formula (2) of Mun as a second host, and (piq)2Ir(acac) as a dopant), an electron injection layer, and a second electrode (Example 1 in [0340]).
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 Compound of Chang as modified by Hyun by incorporating it as the first host compound of an organic light emitting device, as taught by Lee.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of the first host compounds of Lee in an organic light emitting device of Lee would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Chang as modified by Hyun and Lee comprising a first electrode, a hole injection layer, a light emitting layer (Compound of Chang as modified by Hyun as a first host, a compound of Formula (2) of Lee as a second host, and (piq)2Ir(acac) as a dopant), an electron injection layer, and a second electrode.
Conclusion
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786
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