UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`Duk San Neolux Co., Ltd.,
`Petitioner
`
`v.
`
`Idemitsu Kosan Co., Ltd.,
`Patent Owner
`
`Case IPR: Unassigned
`
`DECLARATION OF BENJAMIN J. SCHWARTZ
`
`Mail Stop PATENT BOARD
`Patent Trial and Appeal Board
`US Patent and Trademark Office
`P.O. Box 1450
`Alexandria, VA 22313-1450
`
`1
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000001
`
`
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`Duk San Neolux Co., Ltd.,
`Petitioner
`
`v.
`
`Idemitsu Kosan Co., Ltd.,
`Patent Owner
`
`Case IPR: Unassigned
`
`DECLARATION OF BENJAMIN J. SCHWARTZ
`
`Mail Stop PATENT BOARD
`Patent Trial and Appeal Board
`US Patent and Trademark Office
`P.O. Box 1450
`Alexandria, VA 22313-1450
`
`1
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000001
`
`
`
`1.
`
`I, Benjamin J. Schwartz, make this declaration in connection with the
`
`petition for inter partes review submitted by Petitioner for U.S. Patent No.
`
`9,056,870 (“the ‘870 patent”). All statements herein made of my own knowledge
`
`are true, and all statements herein made based on information and belief are
`
`believed to be true. I am over age 21 and otherwise competent to make this
`
`declaration. Although I am being compensated for my time in preparing this
`
`declaration, the positions articulated herein are my own, and I have no stake in the
`
`outcome of this proceeding or any related litigation or administrative proceedings.
`
`I.
`
`BACKGROUND AND QUALIFICATIONS
`
`2.
`
`Exhibit DSN-1004 is my curriculum vitae. As shown in my
`
`curriculum vitae, I have devoted my career to the field of chemistry, including
`
`research pertaining to quantum theory, light emission in organic LEDs, and
`
`fundamental studies of electron transfer. I earned my Bachelor of Science degree
`
`in both Physics and Chemistry from the University of Michigan in May 1986.
`
`Thereafter, I earned my Ph.D. in Physical Chemistry from the University of
`
`California, Berkeley in December 1992. I am currently a Professor in the
`
`Department of Chemistry and Biochemistry at UCLA. My current research
`
`includes (1) femtosecond laser studies of the dynamics of charge-transfer reactions
`
`and solvated electrons, (2) classical and quantum non-adiabatic computer
`
`simulations of charge transfer, solvation dynamics and the nature of linear
`
`2
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000002
`
`
`
`response, including the development of multi-electron quantum simulation
`
`algorithms, and (3) studies of the spectroscopy, device physics and efficiency of
`
`organic solar cells, including photovoltaic devices based on conjugated polymers
`
`and fullerenes.
`
`3.
`
`In connection with my work, I have extensive experience in the
`
`research, theory, and application of light-emitting materials, including organic
`
`electroluminescent devices. I spent nearly a decade, first as a postdoctoral student
`
`and later as an independent researcher at UCLA, studying organic electronic
`
`materials and their properties when used in light-emitting diodes, and as a result I
`
`am also a named inventor on several issued and pending U.S. patents that pertain
`
`to light-emitting organic materials and organic electroluminescent devices. As I
`
`felt that the outstanding scientific questions in the field of organic LEDs had been
`
`solved by the late 2000’s, at that time I began focusing my research activities on
`
`organic photovoltaics (OPVs), which remain a subject of my current research
`
`interests.
`
`4.
`
`I have been retained in this matter by Vorys, Sater, Seymour and
`
`Pease LLP (“Vorys”) to provide various observations regarding the ‘870 patent. I
`
`am being compensated at the rate of $400 per hour for my work. My fee is not
`
`contingent on the outcome of this matter or on any of the positions I have taken, as
`
`discussed below.
`
`3
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000003
`
`
`
`5.
`
`I have been advised that Vorys represents the Petitioner in this matter.
`
`I have no direct financial interest in the Petitioner.
`
`6.
`
`I have been advised that Idemitsu Kosan Co., Ltd. (hereinafter
`
`referred to as “Idemitsu”) owns the ‘870 patent. I have no financial interest in
`
`Idemitsu or the ‘870 patent. I have not ever had any contact with Idemitsu or the
`
`inventors of the ‘870 patent, Tomoki Kato, Masaki Numata, Kazuki Nishimura,
`
`Toshihiro Iwakuma, and Chishio Hosokawa.
`
`II. MATERIALS CONSIDERED
`
`7.
`
`a.
`
`b.
`
`In preparing this declaration, I have reviewed the following1:
`
`The ‘870 patent (Exhibit DSN-1001);
`
`Excerpts from the prosecution file history of the ‘870 patent (Exhibit
`
`DSN-1002);
`
`c.
`
`A verified translation, filed April 13, 2009, of the specification,
`
`claims, and abstract for U.S. Patent Application No. 12/253,586,
`
`which was originally filed October 17, 2008 (“the ‘586 application”)
`
`(Exhibit DSN-1007);
`
`1 In this declaration, all citations to a given reference should be read as citing to the
`
`English translation of that reference, even if it is listed in the accompanying
`
`petition with a “US” suffix.
`
`4
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000004
`
`
`
`d.
`
`International Patent Application Publication No. WO 2010/107244 A2
`
`(“Kim 2010”) (Exhibit DSN-1008);
`
`e.
`
`An English Translation of KR 10-2011-0058246 A (“Park”) (Exhibit
`
`DSN-1010);
`
`f.
`
`An English Translation of KR 10-2011-0066766 A (“Kim 2011”)
`
`(Exhibit DSN-1012);
`
`g.
`
`An English Translation of PCT/EP2006/007386 (“Heil US,” as an
`
`English translation of Heil) (Exhibit DSN-1015);
`
`h.
`
`Kawaguchi et al., “Synthesis, Structures, and Properties of
`
`Asymmetrical Heteroacenes Containing Both Pyrrole and Furan
`
`Rings,” Organic Letters 2008 Vol. 10, No. 6, pp 1199-1202
`
`(Published online Feb. 16, 2008) (“Kawaguchi”) (Exhibit DSN-1016);
`
`i.
`
`An English copy of PCT/EP2006/003670 filed with Exhibit DSN-
`
`1018 (“Vestweber US”) (DSN-1019);
`
`US 2006/0051612 A1 (“Ikeda”) (DSN-1020);
`
`Moorthy et al., Steric Inhibition of π-Stacking: 1,3,6,8-
`
`j.
`
`k.
`
`Tetraarylpyrenes as Efficient Blue Emitters in Organic Light Emitting
`
`Diodes (OLEDs), Organic Letters 2007, 9:25 (p. 5215) (“Moorthy”)
`
`(DSN-1021);
`
`5
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000005
`
`
`
`l.
`
`Anthony, Functionalized Acenes and Heteroacenes for Organic
`
`Electronics, Chem. Rev. 2006, 108, p. 5028 (“Anthony”) (DSN-1022);
`
`m.
`
`n.
`
`o.
`
`US 2005/0127823 (“Iwakuma”) (DSN-1023);
`
`English translation of PCT/JP2006/317810 (“Toray US”) (DSN-1025);
`
`International Search Report of PCT/JP2009/059980, a Patent Owner’s
`
`International Application claiming priority to the ‘586 application
`
`(DSN-1007) and to the JP prior application (DSN-1005) of the ‘870
`
`patent; and
`
`p.
`
`US 5,942,340 (“Hu”) (DSN-1027).
`
`III. THE PERSON OF ORDINARY SKILL IN THE ART IN THE
`RELEVANT TIMEFRAME
`
`8.
`
`I have been informed that “a person of ordinary skill in the art”
`
`(“POSITA”) is a hypothetical person to whom an expert in the relevant field could
`
`assign a routine task with reasonable confidence that the task would be
`
`successfully carried out. I have been informed that the level of skill in the art is
`
`evidenced by the prior art references. The prior art discussed herein demonstrates
`
`that a POSITA, at the time the ‘870 patent was filed, was aware of various aspects
`
`of organic electroluminescent materials and the use of such materials in
`
`conjunction with, at least, anodes, cathodes, host materials, doping materials, hole-
`
`transporting materials, and electron-transporting materials. Such a person would
`
`6
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000006
`
`
`
`have a bachelor’s degree in chemistry, physics, materials science or a related
`
`discipline and about two to three years of relevant experience, which could be
`
`obtained either through graduate studies or work experience. Such a person would
`
`have had an understanding of the electronic structure of organic materials and how
`
`the electronic structure of such materials impacts their spectroscopic properties and
`
`their performance in organic electroluminescent devices.
`
`9.
`
`Based on my experience, I have a good understanding of the
`
`capabilities of a POSITA. I have interviewed, trained, supervised, directed and
`
`advised many such persons over the course of my career. My statements and
`
`opinions herein are made from the vantage point of a POSITA at the time of the
`
`‘586 application to which the ‘870 patent claims priority.
`
`IV. RELEVANT LEGAL STANDARDS
`
`10.
`
`I have been asked to provide my opinions regarding the disclosure of
`
`the ‘870 patent and its earlier ‘586 application, as well as my opinions as to
`
`whether the claims of the ‘870 patent are anticipated or rendered obvious by the
`
`prior art.
`
`11.
`
`It is my understanding that in order for prior art to anticipate a claim
`
`the reference must disclose each and every element of that claim in the manner as
`
`claimed.
`
`7
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000007
`
`
`
`12.
`
`It is my understanding that a claimed invention is unpatentable if the
`
`differences between the invention and the prior art are such that the subject matter
`
`as a whole would have been obvious at the time of the invention to a POSITA. I
`
`also understand that the obviousness analysis takes into account inquiries including
`
`the level of ordinary skill in the art, the scope and content of the prior art, the
`
`differences between the prior art and the claimed subject matter, and any secondary
`
`considerations that may suggest the claimed invention was not obvious.
`
`13.
`
`I have been informed that the Supreme Court has recognized several
`
`rationales for combining references or modifying a reference to show obviousness
`
`of claimed invention. I understand that some of these rationales include:
`
`a.
`
`combining prior art elements according to a known method to yield
`
`predictable results;
`
`b.
`
`simple substitution of one known element for another to obtain
`
`predictable results;
`
`c.
`
`use of a known technique to improve a similar device (method, or
`
`product) in the same way;
`
`d.
`
`applying a known technique to a known device (method, or product)
`
`ready for improvement to yield predictable results;
`
`e.
`
`choosing from a finite number of identified, predictable solutions,
`
`with a reasonable expectation of success; and showing that the
`
`8
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000008
`
`
`
`claimed product was not one of innovation but of ordinary skill and
`
`commonsense, such that the claimed invention was obvious to try; and
`
`f.
`
`some teaching, suggestion, or motivation in the prior art that would
`
`have led a POSITA to modify the prior art reference or to combine
`
`prior art reference teachings to arrive at the claimed invention.
`
`V.
`
`BACKGROUND OF THE ART
`
`14. Organic materials for use in electroluminescent devices, such as
`
`organic electroluminescent displays (“OELDs”) or organic light emitting diodes
`
`(“OLEDs”) have been researched and known since at least the 1980s. In the time
`
`since their discovery as commercially viable options for electroluminescent
`
`devices, much research has been done to achieve thin film layer materials that
`
`allow for the mass production of OLED products in high volumes with great
`
`luminous efficiency and great functional longevity across the necessary colors.
`
`15.
`
`The mechanism of operation of OLEDs is well understood. An
`
`OLED consists of one or more organic layers sandwiched between an anode and a
`
`cathode. The organic layers may consist of one or more emitting layers and
`
`additional layers, such as electron transporting and/or hole transporting layers. The
`
`cathode injects electrons into the organic layers, while the anode injects holes into
`
`the organic layers. When the device is operated, the electrons and holes migrate
`
`towards one another due to the presence of the applied electric field and recombine
`
`9
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000009
`
`
`
`in the emitting layer, leading either to the direct emission of light, or more
`
`commonly to an electronic excited state that can undergo energy transfer to another
`
`compound that ultimately functions as the light emitter.
`
`16.
`
`One of the earliest organic compounds studied for use in organic
`
`electronic devices, including OLEDs, was poly(vinylcarbazole), which consists of
`
`a π-conjugated heteroacene group with N as the central heteroatom pendant off a
`
`simple carbon polymer chain. Since the electronically active part of this material
`
`are the pendant carbazole groups and not the polymer, subsequent studies looked at
`
`non-polymerized molecular carbazole derivatives, including indolocarbazoles and
`
`carbazoles linked to other aryl and heteroaryl groups, particularly at the N position,
`
`all for the purpose of improving carrier transport and/or electroluminescent
`
`performance. Subsequently, a number of related compounds have become known
`
`to be suitable as materials for use in OELDs that can be combined to yield high
`
`luminous efficiency, minimal pixel defect, and a long operating lifetime.
`
`17.
`
`For example, the use of a molecule with a π-conjugated heteroacene
`
`skeleton such as indolocarbazole but with the hetero nitrogen atom(s) substituted
`
`for oxygen or sulfur, either symmetrically (i.e., cross-linked with two identical
`
`heteroatoms, like N/N or O/O in either a cis or trans configuration) or
`
`asymmetrically (cross-linked with two different heteroatoms, such as N/S or N/O),
`
`and with the heteroatoms arranged in either a cis or trans configuration, as a
`
`10
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000010
`
`
`
`transport or luminescent material for an OLED device is a concept that was known
`
`before the filing of the ‘870 patent, and was discussed in numerous prior art
`
`references, including, e.g., Kim 2010 (DSN-1008), Park (DSN-1010), Kim 2011
`
`(DSN-1012), Kawaguchi (DSN-1016), Vestweber (DSN-1019), Heil (DSN-1015),
`
`Ikeda (DSN-1020), and Toray (DSN-1025).
`
`18.
`
`Further, it was well known in the field that compounds with large
`
`aromatic or heteraromatic skeletons that might be used as the emissive layer in
`
`OLEDs tend to have strong π-stacking interactions in the solid-state. These
`
`interactions can promote charge transport between adjacent molecules but they
`
`also can lead to excimer or aggregate formation and thus potentially a loss of
`
`luminescence efficiency.
`
`It was also well known, however, that adding a bulky
`
`substituent to a compound having an aromatic or heteroaromatic skeleton that is
`
`prone to excessive π-stacking can provide steric hindrance that would be expected
`
`to break up aggregation in the solid state between adjacent molecules and thus
`
`mitigate strong π-stacking interactions as far as luminescence is concerned. Thus,
`
`a POSITA at the time would have been well aware of the need to create molecules
`
`with substituents of appropriate bulk for controlling the amount of π-stacking and
`
`thus tuning the trade-off between carrier mobility and luminescence efficiency as a
`
`means to optimize OLED materials; this concept has been discussed and illustrated
`
`11
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000011
`
`
`
`in the prior art, including, e.g., Moorthy (DSN-1021), Anthony (DSN-1022),
`
`Iwakuma (DSN-1023) and Toray.
`
`19.
`
`Prior to the filing date of the ‘586 application, heteroacenes
`
`containing the N/O combination were studied and found to exhibit strong π-
`
`stacking interactions, providing the potential for high carrier mobility and thus
`
`possible application in organic field-effect transistors (OFET materials) and other
`
`organic electronic devices. As known from the above prior art, compounds that
`
`work in OFETs often have quenched luminescence due to their strong π-stacking
`
`interactions. These compounds can be rendered suitable for use in the emissive
`
`layer of OLEDs, however, because their solid-state luminescence can be restored
`
`by synthetic modification with the addition of one or more bulky side groups.
`
`Moreover, since most organic OFET compounds with this type of backbone are p-
`
`type and exhibit high hole mobility, a common strategy to convert OFET
`
`compounds into compounds suitable for the emissive layer in OLEDs is to make
`
`the bulky side group electron deficient, thus serving the dual purpose of increasing
`
`luminescence by reducing strong π-stacking interactions and also improving
`
`electron transport. In combination, this strategy allows one to screen materials for
`
`good carrier mobility in OFETs and then modify them for use as emissive OLED
`
`materials.
`
`12
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000012
`
`
`
`20.
`
`Finally, another important criterion for OLED operation is balanced
`
`transport of the electrons and holes. Since electrons and holes may not be injected
`
`into a material with equal ease, most OLED devices use electron and hole
`
`transporting layers that are designed to have energy levels that match the work
`
`functions of the electrodes for balanced injection. It is important, however, that
`
`carrier balance also be achieved in the emissive layer for maximum luminescence
`
`efficiency. This means that the HOMO and LUMO levels of the molecule in the
`
`emissive layer may need to be fine-tuned to help improve balance. It was well
`
`known by the time of the ‘586 application that this type of fine tuning could be
`
`accomplished by changing heteroatoms on a heteroacene skeleton and/or by
`
`changing the electron withdrawing nature of any substituents pendant to the
`
`heteroacene skeleton.
`
`VI. U.S. PATENT NO. 9,056,870
`
`21.
`
`The ‘870 patent was filed as US Patent Application No. 13/173,486
`
`on June 30, 2011, as a continuation application of US Patent Application No.
`
`12/253,586 (“the ‘586 application”), which was filed on October 17, 2008.
`
`22.
`
`I have read the ‘586 application in view of the claimed material of
`
`Formula (1) or (2) and other claims in the ‘870 patent, and have found:
`
`i.
`
`No subgenuses or species of the genus of Formula (1) or (2) having “a
`
`substituted or unsubstituted naphthalene” as Ar2 are described in the
`
`13
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000013
`
`
`
`‘586 application. There also is no description regarding what
`
`structures Formula (1) or (2) can be when Ar2 is a substituted or
`
`unsubstituted naphthalene.
`
`ii.
`
`Formulas (1) and (2) define Ar1, Ar2 and Ar3 as the core of the
`
`heteroacene skeleton, each of which is connected through bridging
`
`units X1 (NR1) and X2 (O or S); however, the formula does not define
`
`how they are connected to adjacent groups. Many tens of different
`
`core types of the formulas, where Ar2 is a substituted or unsubstituted
`
`naphthalene, may be encompassed by Formula (1) or Formula (2)
`
`depending on the bonding position of X1 (NR1) to Ar1 and Ar2, and X2
`
`(O or S) to Ar2 and Ar3.
`
`iii.
`
`I understand that a similar issue was raised in the International Search
`
`Report (DSN-1026) in International Patent Application No.
`
`PCT/JP2009/059989 filed by the same inventors of the ‘870 patent
`
`and claiming priority to the ‘586 application (DSN-1007) and to the
`
`JP prior application (DSN-1005) of the ‘870 patent, but where Ar1 to
`
`Ar3 are defined as a 6-memberted aromatic ring: “(a) Although Ar2,
`
`X2 and X3 are mentioned as the structures contained in the repeating
`
`unit, it is unclear as to how each of these groups is bound to an
`
`adjacent group Ar1, Ar2, or the like. (b) In claim 1, it is defined that
`
`14
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000014
`
`
`
`each of the groups Ar1 to Ar3 has a 6-membered aromatic ring.
`
`However, only compounds each having a benzene ring are disclosed
`
`in the description, and any compound having a structure other than a
`
`benzene ring (e.g., a pyridine ring) is not produced. Therefore, on this
`
`point, the inventions of the present application are not supported by
`
`the description.”
`
`iv.
`
`All the various subgenus Formulas (5), (7) to (9), (13), (15) and (17)
`
`of genus Formula (1), and all the various subgenus Formulas (6), (10)
`
`to (12), (14), (16) and (18) of genus Formula (2), as well as all 8 of
`
`the example heteroacene skeletons disclosed in the ‘586 application
`
`have only benzene as Ar2.
`
`v.
`
`None of the 476 species described as examples of the formulas in the
`
`‘586 application have naphthalene as Ar2. Only eight of the 476
`
`species have asymmetric core structures where the heteroacene
`
`backbone is crosslinked with NR1 and O (or S), but again none of
`
`these have a heteroaryl group as R1 as patented.
`
`vi.
`
`None of the 26 compounds prepared as a host material for an OLED
`
`in the ‘586 application are crosslinked with NR1/O (or S).
`
`vii. After reading the disclosure in the ‘586 applicataion, it is my opinion
`
`that at the time the ‘586 application was filed, Kato et al. did not have
`
`15
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000015
`
`
`
`possession of the full scope of the materials/compounds claimed in the
`
`‘870 patent, especially of a subgenus compound where Ar2 is
`
`naphthalene, substituted or unsubstituted, and R1 is a heteroaryl as
`
`claimed. Kato et al. never disclosed, described, synthesized, tested or
`
`employed in an OLED any compound of Formula (1) where Ar2 is
`
`naphthalene or any compound of Formula (1) where Ar2 is
`
`naphthalene and R1 is a heteroaryl on core skeleton crosslinked with
`
`NR1 and O (or S) as claimed.
`
`23.
`
`The ‘870 patent describes that it relates to the new concept of using a
`
`compound having a π-conjugated heteroacene skeleton cross-linked with a C, N, O
`
`or S atom as a material for an OLED showing a high luminous efficiency, free of
`
`any pixel defect, and having a long lifetime. DSN-1001 at 3:15-32; 6:47-53;
`
`201:40-205:20. The alleged new concept, however, was known in the art prior to
`
`the ‘870 patent in many references, including, e.g., Kim 2010 (DSN-1008), Park
`
`(DSN-1010), and Kim 2011 (DSN-1012), or prior to the ‘586 application by
`
`combinations of references including, e.g., Heil (DSN-1015), Kawaguchi (DSN-
`
`1016), Vestweber (DSN-1019), Ikeda (DSN-1020), Iwakuma (DSN-1023),
`
`Moorthy (DSN-1021), Anthony (DSN-1022), and Toray (DSN-1025), all of which
`
`I discuss in detail below.
`
`16
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000016
`
`
`
`24.
`
`I understand that the closest prior art considered during prosecution of
`
`the ‘870 patent is Heil et al. (WO 2007/022845 Al), which discloses compounds of
`
`the following form:
`
`Formula (2a)
`
`([0029]) where X = C(R1)2, N(R1), O, or S ([0018]); R1 = aryl or heteroaryl
`
`group ([0019]) such as benzene or pyridine ([0024]). A particular embodiment is
`
`disclosed:
`
`(page 11).
`
`My understanding is the Patent Office decided that Heil et al. do not provide
`
`sufficient motivation to produce the compounds according to formulae (1) or (2) as
`
`defined in the claims of the ‘870 patent, particularly in regards to X1-X2. DSN-
`
`1002 at 13-14. However, as discussed in detail below in Section VII, it is my
`
`opinion that each of Claims 1, 3, 4 and 14-26 of the ‘870 patent is either
`
`anticipated or rendered obvious by prior art, including Heil et al.
`
`25. Claims 1, 3, 4 and 14-26 of the ‘870 patent are the challenged claims.
`
`In this regard, it is my understanding that:
`
`17
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000017
`
`
`
`Claim 1 is directed to a material for an organic EL device represented by
`
`Formula (1) or (2):
`
`where o and p are defined as 0, thereby excluding X3 and X4 and producing a “cis”
`
`form of the heteroacene skeleton; X1 is defined as NR1 and X2 as O or S, thereby
`
`representing “asymmetrical” heteroacene backbones (materials where X1 or X2 is
`
`CR2CR3, i.e., non-hetroacene backbones, are excluded); Ar1 and Ar3 are each a
`
`substituted or unsubstituted benzene, and Ar2 is a substituted or unsubstituted
`
`benzene or a substituted or unsubstituted naphthalene group; each of Ar1 to Ar3
`
`may be optionally substituted with a single or multiple Y(s), and Ar1 and Ar3 are
`
`optionally substituted with A1-L1 and A2-L2, respectively; when Ar1 to Ar3 are
`
`substituted with a group of Y, A1-L1, or A2-L2, which is a heteroaryl having a ring
`
`formed of 3 to 24 atoms, the substituent is connected to Ar1 to Ar3 through C-C
`
`bonds; and when L1 or L2 is a C1-20 alkyl or alkylene, A1 or A2 is not hydrogen.
`
`Claims 3 and 4 are each dependent from Claim 1, where X2 is O.
`
`Claim 14 is dependent from Claim 1, where X2 is S.
`
`Claim 15 is dependent from Claim 2, where L1 and L2 each are a single bond
`
`and A1 and A2 each are hydrogen (H) atoms.
`
`18
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000018
`
`
`
`Claim 16 is dependent from Claim 15, wherein Ar2 is an unsubstituted
`
`benzene group or an unsubstituted naphthalene group.
`
`Claim 17 is directed to an organic EL device comprising one or more
`
`organic thin film layers including a light-emitting layer between a cathode and an
`
`anode, wherein at least one layer of the organic thin film layers contains the
`
`material for an organic electroluminescence device of Claim 14.
`
`Claim 18 is dependent from Claim 17, wherein the light-emitting layer
`
`contains the material for an organic EL device as a host material.
`
`Claim 19 is dependent from Claim 18, wherein the light-emitting layer
`
`further contains a phosphorescent material.
`
`Claim 20 is dependent from Claim 17, wherein R1 is a substituted or
`
`unsubstituted heteroaryl group having a ring formed of 3 to 24 atoms.
`
`Claim 21 is dependent from Claim 1, wherein Ar2 is an unsubstituted
`
`naphthalene group.
`
`Claims 22 and 23 each are dependent from Claim 1, wherein R1 is selected
`
`from the group consisting of pyridine, pyridazine, pyrimidine, pyrazine, carbazole,
`
`dibenzofuran, dibenzothiophene, phenoxazine and dihydroacridine (Claim 22),
`
`particularly pyridine, pyridazine, pyrimidine and pyrazine (Claim 23).
`
`Claim 24 is dependent from Claim 1, wherein the material has formula (1)
`
`and L1 and L2 are single bonds.
`
`19
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000019
`
`
`
`Claims 25 and 26 are dependent from Claim 1, wherein R1 is a substituted or
`
`unsubstituted heteroaryl group having a ring formed of 8 to 24 atoms and having a
`
`fused ring structure comprising at least one of a pyrimidine group, a pyridine
`
`group, a pyrazine group and a pyridazine group (Claim 25), particularly a
`
`pyrimidine group (Claim 26).
`
`VII. CONTENTS OF PRIOR ART NOT CITED BY THE PATENT
`OFFICE
`
`A. Kim 2010
`
`26.
`
`Kim 2010 (DSN-1008) describes an OLED material and an OLED
`
`using the material. In Tables 1 to 3, Kim 2010 describes OLED materials prepared
`
`with a heteroacene skeleton (compounds TA, TB and TC) and various substituents
`
`(Ar1, Ar2) on the bridging unit N. Among them, two compounds have asymmetric
`
`heteroacene skeletons with N/O (TC3) and N/S (TC9) in a cis orientation. These
`
`compounds have a phenyl-substituted pyrimidine substituent (H4) on the bridging
`
`unit N of the backbone.
`
`Compound TC3-H4, DSN-1008 at 28
`
`Compound TC9-H4 , DSN-1008 at 30
`
`27. Kim 2010 further describes the use of these compounds (as well as an
`
`20
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000020
`
`
`
`entire series of compounds described in Tables 2 and 3) as host materials in OLED
`
`(DSN-1008 at Claim 6). Kim 2010 also demonstrates OLED operation with high
`
`brightness and efficiency when the compounds are combined with a
`
`phosphorescent light-emitter (DSN-1008 at Claim 10).
`
`28. Kim 2010 specifically describes compounds TC1 or TC7 (shown
`
`below), which meet the general class of compounds in the ‘870 patent with R1
`
`(which is Ar1 in the structure of TC1 or TC7) being pyridine (H2), pyrazine (H8),
`
`isoquinoline (H14) or quinazoline (H19) and the asymmetric cis heteroacene
`
`backbone is connected by NR1/O or NR1/S. From this disclosure, it is obvious that
`
`a POSITA would have been readily able to arrive at the subject matter of claims
`
`22, 23, 25 and 26 of the ‘870 patent.
`
`29. Kim 2010 also provides specific examples and methods to prepare
`
`compounds with Formulas (1) to (5). In particular, compound H19 (quinazoline)
`
`was actually used as substituent Ar1 in compound TA1 having the heteroacene
`
`backbone with heteroatoms N/N, which is a class of compounds specifically
`
`described in the ’870 patent. Accordingly, a POSITA would have been obviously
`
`led to follow the same synthetic route and prepare compounds TC7 or TC1
`
`substituted with H2 (pyridine) or H19 (quinazoline), as depicted below.
`
`21
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000021
`
`
`
`TC7-H2
`
`TC7-H19
`
`Accordingly, Kim 2010 renders obvious the subject matter of claims 22, 23,
`
`25 and 26 of the ’870 patent.
`
`B. Park
`
`30.
`
`Park (DSN-1010) discloses materials used in bright, stable OLEDs
`
`that are based on a heteroacene skeleton. In particular, Park describes two specific
`
`molecules (labeled 2-6 and 2-12 as examples of Formula 8; DSN-1010, Claim 8)
`
`that fall into the general formula specified by the ‘870 patent. These two
`
`molecules have an unsubstituted benzene at the positions corresponding to Ar1, Ar2
`
`and Ar3, with NR1 as X1, S as X2, and a pyridine group or a quinolone group as R1,
`
`with single bonds for L1 and L2, and hydrogen atoms as A1 and A2.
`
`22
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000022
`
`
`
`31.
`
`Park describes Compounds 2-6 to 2-15 as specific examples of
`
`materials for organic EL devices, all having a pyridine, pyrimidine, or pyridine-
`
`containing fused heteroaryl group as substituents on the N atom (R1). See below.
`
`Park also suggests that the N-atom substituent can be a heteroaryl group containing
`
`up to 60 C atoms as well as one or more atoms other than C. Thus, Park renders
`
`obvious the use of a pyrimidine-containing fused heteroaryl, including extended N-
`
`based fused heteroaryls such as the quinoline substituent in Compound 2-12, as a
`
`substituent for materials used in organic EL devices, as recited in claim 26. As a
`
`result, Park anticipates claims 1, 14-20 and 22-25 and renders obvious claim 26 of
`
`the ‘870 patent.
`
`C. Kim 2011
`
`32.
`
`Kim 2011 (DSN-1012) discloses a compound that falls within the
`
`23
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000023
`
`
`
`general formula specified by the ‘870 patent that is useful in bright, stable OLEDs.
`
`In particular, Kim 2011 describes molecules for this purpose with general formula
`
`(2), below. One specific example given by Kim 2011 is compound 129 (DSN-
`
`1012 at claim 7), which fits the general formula of the ‘870 patent with
`
`unsubstituted benzene as Ar1 and Ar3, unsubstituted naphthalene as Ar2, NR1 as X1,
`
`S as X2 (in the claimed cis configuration), diphenyl-substituted pyrimidine as R1,
`
`single bonds as L1 and L2, and hydrogen atoms as A1 and A2.
`
`Formula (2)
`
`Compound 129
`
`33.
`
`As mentioned previously, claims 17-20 of the ’870 patent relate to
`
`“an organic EL device comprising one or more organic thin film layers including a
`
`light emitting layer between a cathode and an anode, wherein the light emitting
`
`layer contains the material for an organic EL device of Claim 14” (i.e., the material
`
`of Claim 1 where X2 is S), where “R1 is a substituted or unsubstituted heteroaryl
`
`group having a ring formed of 3-24 atoms” as a host material together with “a
`
`phosphorescent material.” See supra ¶ 25.
`
`34. Kim 2011 describes the fabrication of organic EL devices based on
`
`compounds 4, 56, 94 and 107 (which all fall in the class of formula (2), above) as
`
`24
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000024
`
`
`
`the host material and a phosphorescent compound as the light emitter, and argues
`
`that these materials should be preferred because they provide high brightness and
`
`stability for the organic EL device. Kim 2011 also claims that all compounds of
`
`formulas (1) to (6) should be similarly advantageous for organic EL devices.
`
`35.
`
`It is obvious that a POSITA would have thought to try compound 129,
`
`which has a diphenyl-substituted heteroaryl group of 6 atoms (pyrimidine) for R1,
`
`to fabricate an improved organic EL device. Since this compound falls directly in
`
`the class specified by claims 17-20 of the ’870 patent, this renders those claims
`
`obvious.
`
`36. Although compound 129 in Kim 2011 contains diphenyl-substituted
`
`pyrimidine for R1, and compound 139 in Kim 2011 contains quinoline-substituted
`
`benzene for R1, it would be clear to a POSITA that other structurally similar
`
`nitrogen-containing heterocycles used at this position would also give similar
`
`performance, and that the use of other nitrogen heterocycles (e.g., pyridine, triazine,
`
`pyridine- or pyrimidine-containing fused heteroaryl groups) would change the
`
`electron-withdrawing nature of this group, allowing one to subtly tune the energy
`
`levels of the compound and thus the charge balance and performance of EL
`
`devices based on these compounds. This is, for example, why Park shows both
`
`pyridine (compound 2-6) and quinoline (compound 2-12) substituents in this
`
`location, why Ikeda shows pyridine at this position, why Kim 2010 demonstrates
`
`25
`
`DUK SAN NEOLUX
`EXHIBIT 1003
`PAGE 000025
`
`
`
`substitution of many different N heterocycles at this molecular position (groups
`
`H2, H8, H14 and H19), and why Iwakuma offers a series of N-based heterocycles
`
`serving this same role. Given that substituting different N heterocycles on
`
`substituents is common in the field of organic molecules for electronic
`
`applications, Kim 2011 renders claims 22, 23, 25 and 26 obvious.
`
`D. Kawaguchi
`
`37. Kawaguchi (DSN-1016) describes a series of readily-synthesized
`
`asymmetrical heteroacene skeleton-based compounds disclosed in the specification
`
`of the ‘870 patent that could be useful in organic electronic devices. In particular,
`
`Kawaguchi notes that this class of compounds tends to form antiparallel co-facial
`
`π-stacking arrangements in the solid state, which is beneficial for charge transport
`
`through films comprised of these mole
Accessing this document will incur an additional charge of $.
After purchase, you can access this document again without charge.
Accept $ Charge
Still Working On It
This document is taking longer than usual to download. This can happen if we need to contact the court directly to obtain the document and their servers are running slowly.
Give it another minute or two to complete, and then try the refresh button.
A few More Minutes ... Still Working
It can take up to 5 minutes for us to download a document if the court servers are running slowly.
Thank you for your continued patience.
This document could not be displayed.
We could not find this document within its docket. Please go back to the docket page and check the link. If that does not work, go back to the docket and refresh it to pull the newest information.
Your account does not support viewing this document.
You need a Paid Account to view this document. Click here to change your account type.
Your account does not support viewing this document.
Set your membership
status to view this document.
With a Docket Alarm membership, you'll
get a whole lot more, including:
- Up-to-date information for this case.
- Email alerts whenever there is an update.
- Full text search for other cases.
- Get email alerts whenever a new case matches your search.
One Moment Please
The filing “” is large (MB) and is being downloaded.
Please refresh this page in a few minutes to see if the filing has been downloaded. The filing will also be emailed to you when the download completes.
Your document is on its way!
If you do not receive the document in five minutes, contact support at support@docketalarm.com.
Sealed Document
We are unable to display this document, it may be under a court ordered seal.
If you have proper credentials to access the file, you may proceed directly to the court's system using your government issued username and password.
Access Government Site
