Source: http://www.google.com/patents/US6165383?dq=6,202,008
Timestamp: 2015-01-29 18:40:00
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Patent US6165383 - Anthracene derivatives having at least one reactive silyl group that is ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsPrecursor materials useful for making organic electroluminescent devices such as anthracene derivatives having the structure: ##STR1## R40 -R43 and R44 -R47 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy,...http://www.google.com/patents/US6165383?utm_source=gb-gplus-sharePatent US6165383 - Anthracene derivatives having at least one reactive silyl group that is effective to form siloxane bondsAdvanced Patent SearchPublication numberUS6165383 APublication typeGrantApplication numberUS 09/173,393Publication dateDec 26, 2000Filing dateOct 15, 1998Priority dateApr 10, 1998Fee statusLapsedPublication number09173393, 173393, US 6165383 A, US 6165383A, US-A-6165383, US6165383 A, US6165383AInventorsHomer Z. ChouOriginal AssigneeOrganic Display TechnologyExport CitationBiBTeX, EndNote, RefManPatent Citations (8), Non-Patent Citations (364), Referenced by (150), Classifications (40), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetAnthracene derivatives having at least one reactive silyl group that is effective to form siloxane bondsUS 6165383 AAbstract Precursor materials useful for making organic electroluminescent devices such as anthracene derivatives having the structure: ##STR1## R40 -R43 and R44 -R47 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkylthio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, sulfonyl, sulfonyloxy. R48 and R49 are selected independently from the group consisting of trialkoxysilyl, dialkoxysilyl, trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy.
What is claimed: 1. A compound having the formula: ##STR13## wherein R40 -R43 and R44 -R47 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkylthio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, sulfonyl, sulfonyloxy; and R48 and R49 are selected independently from the group consisting of trialkoxysilyl, dialkoxysilyl, trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy.
2. The compound of claim 1, wherein R48 and R49 are selected independently from the group consisting of trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy.
3. The compound of claim 2, wherein R48 and R49 are selected independently from the group consisting of trichlorosilyl or dichlorosilyl.
4. The compound of claim 3, wherein each of R48 and R49 is trichlorosilyl.
5. The compound of claim 4 having the stucture: ##STR14##
6. A compound having the structure: wherein R50 -R55 and R56 -R61 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkylthio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, sulfonyl, sulfonyloxy; and R62 and R63 are selected independently from the group consisting of trialkoxysilyl, dialkoxysilyl, trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy.
7. The compound of claim 6, wherein R62 and R63 are selected independently from the group consisting of trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy.
8. The compound of claim 7, wherein R62 and R63 are selected independently from the group consisting of trichlorosilyl and dichlorosilyl.
9. The compound of claim 8, wherein each of R62 and R63 is trichlorosilyl.
10. The compound of claim 9, having the formula: ##STR15##
1 CROSS REFERENCE TO RELATED U.S. PATENT APPLICATIONS This application claims priority from provisional U.S. patent application Ser. No. 60/081,277, entitled Organic Electroluminescent Device, by Homer Chou, filed Apr. 10, 1998. This application is also related to U.S. patent application Ser. No. 09/172,843, pending, filed on even date herewith.
The present invention relates to light-emitting materials and devices constructed using such materials. More specifically, the present invention relates to organic, electroluminescent materials and associated devices. The present invention has applications in the areas of materials science, organic chemistry, and electronics.
Makers of electronic devices that produce visual information, such as computers, are working intensely to develop display devices that provide brighter, sharper pictures at lower manufacturing cost and less weight. The drive to lighter, cheaper, better displays has lead to the development of flat-panel displays ("FPDs") that are commonly used in laptop computers and include a growing share of the desktop computer display market. FPDs are almost exclusively liquid crystal displays ("LCDs"). However, LCD technology has shortcomings, including weak brightness and large power requirements.
One alternative to LCDs are electroluminescent ("EL") displays. EL displays use the luminescense of a solid film that is produced when a voltage is applied to the solid film. Referring to FIG. 1, which illustrates the process generally, the electroluminescent material ("EML") is placed between a cathode and an anode. The application of an electric potential (typically 100 MV/m) injects holes into the highest occupied molecular orbital ("HOMO") or valence band ("VB") of the EML from the anode, and electrons are injected into the lowest unoccupied molecular orbital ("LUMO") of the EML or conduction band ("CB"). The recombination of the electrons and holes in the EML causes the emission of light from EML.
To facilitate the production of holes and electrons, a hole transport layer ("HTL") and/or electron transport layer ("ETL") are provided to increase the efficiency of hole (electron) injection and recombination. This has lead to the design of EL displays having the general structure shown in FIG. 2 at 200. There, an electrode 202 is coupled with an electron transport layer 204. ETL 204 is coupled with electroluminescent layer 206, which, in turn, is coupled with hole transport layer 208. HTL 208 is coupled with electrode 210. Electrodes 202 and 210 are connected by contacts 212 and 214 that are each coupled to a source 216.
Presently, EL displays are fabricated using either inorganic materials, such as manganese (Mn)-doped zinc sulfide (ZnS), or organic materials such as polyphenylene vinylene ("PPV") and its derivatives. However, no satisfactory EL material has been developed for widespread applications. Although inorganic EL displays can provide high performance and durability, they suffer from large power requirements and expensive, low-throughput fabrication processes. Thus, inorganic EL displays have been relegated largely to niche applications, such as military and medical applications. Organic EL displays, on the other hand, can be fabricated more cheaply and simply than inorganic EL displays, but suffer from relatively poor performance. Thus, a need remains to provide an EL display having a cost/performance profile that is suitable for the general marketplace. Such a device will require materials that are relatively inexpensive and simple to prepare compared to inorganic EL displays while providing comparable performance characteristics. The present invention meets these and other needs.
3 SUMMARY OF THE INVENTION The present invention provides precursor materials useful for forming organic electroluminescent materials that have desirable efficiency, weight, and durability properties, as well as devices made from such electroluminescent materials. The precursor materials provided by the present invention are relatively straightforward to make, thereby being economically attractive. Thus, the precusor materials of the invention will be appreciated by those of skill in the materials and electronics arts to address important needs in those fields.
In a first aspect, the present invention provides anthracene derivatives having the formula shown below: ##STR2## R43 and R44 -R47 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkylthio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, sulfonyl, sulfonyloxy. R45 and R49 are selected independently from the group consisting of trialkoxysilyl, dialkoxysilyl, trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy.
In more particular embodiments, R48 and R49 are selected independently from the group consisting of trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy. Still more particular embodiments are those for which R48 and R49 are tricholorsilyl or dichlorosilyl. Yet more particular embodiments are those for which R48 and R49 each is trichlorosilyl. A specific embodiment is that for which R48 and R49 each is trichlorosilyl and R40 -R43 and R44 -R47 each is hydrogen: ##STR3##
In a second aspect, the present invention provides useful pentacene derivatives having the following formula: ##STR4## R50 -R55 and R56 -R61 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkylthio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, sulfonyl, sulfonyloxy. R62 and R63 are selected independently from the group consisting of trialkoxysilyl, dialkoxysilyl, trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy.
In more particular embodiments, R62 and R63 are selected independently from the group consisting of trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy. Still more particular embodiments are those for which R62 and R63 are tricholorsilyl or dichlorosilyl. Yet more particular embodiments are those for which R62 and R63 each is trichlorosilyl. A specific embodiment is that for which R62 and R63 each is trichlorosilyl and R50 -R55 and R56 -R61 each is hydrogen: ##STR5##
4 BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a schematic of the electronic energy levels for an electroluminescent device comprising an anode, a hole transport layer ("HTL"), an electroluminescent layer ("EML"), and electron transport layer ("ETL"), and a cathode. Also shown are the conduction bands ("CB") and valence bands ("VB") of the materials. The filled circles represent LUMOs (lowest unoccupied molecular orbitals); the empty circles represent HOMOs (highest occupied molecular oribitals).
FIG. 2 is a schematic of an electroluminescent device according to the prior art that is consistent with the energy diagram illustrated in FIG. 1.
FIG. 3 is a schematic of an electroluminescent device according to one embodiment of the invention.
FIG. 4 is a schematic of an electroluminescent device according to a second embodiment of the invention.
FIG. 5A and FIG. 5B are schematics describing the formation of various siloxane networks in accordance with the present invention. FIG. 5A is a schematic illustration of a proposed chemical reaction mechanism by which the organo-siloxane polymers of the invention are formed. FIG. 5B illustrates a proposed chemical reaction mechanism for the formation of substrate-bound organo-siloxane polymers of the invention.
FIG. 6 is the proton nuclear magnetic resonance spectrum ("1 H NMR") of 9,10-bisallylanthracene taken at an applied field strength of 200 megahertz (MHz) using a hexadeuterobenzene (C6 D6) standard.
5 DESCRIPTION OF SOME EMBODIMENTS OF THE INVENTION The present invention provides organic electroluminescent materials having desirable efficiency, weight, and durability properties, as well as devices made from such materials. The materials provided by the present invention are relatively straightforward to make, thereby being economically attractive. These beneficial results are achieved in some embodiments in which a single electroluminescent conductive layer replaces the multiplicity of layers used by the prior art. Thus, the organic electroluminescent materials and devices of the invention will be appreciated by those of skill in the materials and electronics arts to address important needs in those fields.
The following terms will be understood as defined in this Section 5.1 unless noted otherwise.
5.1.1 Electroluminescent Material
A material that emits photons under the application of an electric potential.
5.1.2 Electroluminescent Article
A device including at least an anode, a cathode, and an electroluminescent material arranged between the anode and cathode.
5.1.3 Conducting Material
A material that allows the passage of electrons under the application of an electric potential of less than about 10 volts/micrometer (V/μm).
5.1.4 Electroluminescently Conductively Coupled Directly
The phrase "electroluminescently conductively coupled directly" as used herein means an arrangement of an electrode and an electroluminescent material in which electrons move from the electrode to a electroluminescent material without traversing an unenhanced hole transport material or unenhanced electron transport material (as defined with respect to Sections 5.1.5-5.1.8 hereinbelow) that is arranged between the electroluminescent material and the electrode.
5.1.5 Hole Transport Layer ("HTL")
A "hole transport layer" ("HTL") is a material that stabilizes the formation of radical cations in an electroluminescent article containing a certain electroluminescent material relative to the same electroluminescent article lacking such a material. Examples of hole transport layers include, without limitation, substituted and unsubstituted phthalocyanic and porphyrinic compounds such as described in U.S. Pat. No. 5,409,783, which is incorporated herein by reference, such as silicon phthalocyanine dichloride and 5,10,14,20-tetraphenyl-21H,23H-porphine silicon (IV) dichloride. Other examples of HTLs include, without limitation, tertiary aromatic amines such as those described in U.S. Pat. Nos. 3,180,730; 3,567,450; and 3,658,520 (each of which incorporated herein by reference); as well as the above-incorporated U.S. Pat. No. 5,409,783.
5.1.6 Enhanced Hole Transport Layer
An "enhanced hole transport layer" is defined herein to mean a hole transport layer as defined in Section 5.1.5 that further includes at least one additional component that increases the performance of the electroluminescent article relative to an electroluminescent article lacking an enhanced hole transport layer as measured by performance characteristics including, but not limited to, threshold turn-on voltage, luminosity (brightness), article lifetime, emission wavelength(s).
5.1.7 Electron Transport Layer ("ETL")
An "electron transport layer" ("ETL") is a material that stabilizes the formation of radical anions in an electroluminescent article containing a certain electroluminescent material relative to the same electroluminescent article lacking such a material. Exemplary ETL materials include, without limitation, substituted oxazoles, isoxazoles, thiazoles, isothiazoles, oxadiazoles, and thiadiazoles, such as those described in U.S. Pat. No. 5,276,381, which is incorporated herein by reference.
5.1.8 Enhanced Electron Transport Layer
An "enhanced electron transport layer" is an electron transport layer as defined in Section 5.1.7 that further includes at least one additional component that increases the performance of the electroluminescent article relative to an electroluminescent article lacking an enhanced electron transport layer as measured by performance characteristics including, but not limited to, threshold turn-on voltage, luminosity (brightness), article lifetime, emission wavelength(s).
5.1.9 Alkyl
The term "alkyl" as used herein refers to a straight, branched, or cyclic hydrocarbon chain fragment or radical containing between about one and about twenty carbon atoms, more preferably between about one and about ten carbon atoms (e.g., methyl, ethyl, n-propyl, iso-propyl, cyclopropyl, n-butyl, iso-butyl, tert-butyl, cyclobutyl, adamantyl, noradamantyl and the like). Straight, branched, or cyclic hydrocarbon chains having eight or fewer carbon atoms will also be referred to herein as "lower alkyl". The hydrocarbon chains may further include one or more degrees of unsaturation, i.e., one or more double or triple bonds (e.g., vinyl, propargyl, allyl, 2-buten-1-yl, 2-cyclopenten-1-yl, 1,3-cyclohexadien-1-yl, 3-cyclohexen-1-yl and the like). Alkyl groups containing double bonds such as just described will also be referred to herein as "alkenes". Similarly, alkyl groups having triple bonds will also be referred to herein as "alkynes". However, as used in context with respect to cyclic alkyl groups, the combinations of double and/or triple bonds do not include those bonding arrangements that render the cyclic hydrocarbon chain aromatic.
In addition, the term "alkyl" as used herein further includes one or more substitutions at one or ore carbon atoms of the hydrocarbon fragment or radical. Such substitutions include, but are not limited to: aryl; heterocycle; halogen (to form, e.g., trifluoromethyl, --CF3); nitro (--NO2); cyano (--CN); hydroxyl (also referred to herein as "hydroxy"), alkoxyl (also referred herein as alkoxy) or aryloxyl (also referred to herein as "aryloxy", --OR); thio or mercapto, alkyl, or arylthio (--SR); amino, alkylamino, arylamino, dialkyl- or diarylamino, or arylalkylamino (--NRR ); aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl or arylalkylaminocarbonyl (--C(O)NRR'); carboxyl, or alkyl- or aryloxycarbonyl (--C(O)OR); carboxaldehyde, or aryl- or alkylcarbonyl (--C(O)R); iminyl, aryl- or alkyliminyl (--C(═NR)R'); sulfo (--SO2 OR); alkyl- or arylsulfonyl (--SO2 R); carbamido (--HNC(═O)NRR'); or thiocarbamido (--HNC(═S)NRR'); trihalosilyl (X3 Si--, where X is halogen as defined herein); trialkoxysilyl ((RO3 Si--)); where R and R' independently are hydrogen, aryl or alkyl as defined herein. Substituents including heterocyclic groups (i.e., heterocycle, heteroaryl, and heteroaralkyl) are defined by analogy to the above-described terms. For example, the term "heterocycleoxy" refers to the group -OR, where R is heterocycle as defined below.
5.1.10 Carbonyl
The term "carbonyl" as used herein refers to the functional group --C(O)--. However, it will be appreciated that this group may be replaced with well-known groups that have similar electronic and/or steric character, such as thiocarbonyl (--C(S)--); sulfinyl (--S(O)--); sulfonyl (--SO2 --); phosphonyl (--PO2 --), and methylene (--C(CH2)--). Other carbonyl equivalents will be familiar to those having skill in the medicinal and organic chemical arts.
5.1.11 Aryl
The term "aryl" as used herein refers to cyclic aromatic hydrocarbon chains having twenty or fewer carbon atoms, e.g., phenyl, naphthyl, biphenyl and anthracenyl. One or more carbon atoms of the aryl group may also be substituted with, e.g.,: alkyl; aryl; heterocycle; halogen; nitro; cyano; hydroxyl, alkoxyl or aryloxyl; thio or mercapto, alkyl-, or arylthio; amino, alkylamino, arylamino, dialkyl-, diaryl-, or arylalkylamino; aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl or arylalkylaminocarbonyl; carboxyl, or alkyl- or aryloxycarbonyl; carboxaldehyde, or aryl- or alkylcarbonyl; iminyl, or aryl- or alkyliminyl; sulfo; alkyl- or arylsulfonyl; hydroximinyl, or aryl- or alkoximinyl; carbamido; or thiocarbamido. In addition, two or more alkyl or heteroalkyl substituents of an aryl group may be combined to form fused aryl-alkyl or aryl-heteroalkyl ring systems (e.g., tetrahydronaphthyl). Substituents including heterocyclic groups (e.g., heterocycleoxy, heteroaryloxy, and heteroaralkylthio) are defined by analogy to the above-described terms.
5.1.12 Aralkyl
The term "aralkyl" as used herein refers to an aryl group that is joined to a parent structure by an alkyl group as described above, e.g., benzyl, α-methylbenzyl, phenethyl, and the like.
5.1.13 Heterocycle
The term "heterocycle" as used herein refers to a cyclic alkyl group or aryl group as defined above in which one or more carbon atoms have been replaced by a non-carbon atom, especially nitrogen, oxygen, or sulfur. Non-aromatic heterocycles will also be referred to herein as "cyclic heteroalkyl". Aromatic heterocycles are also referred to herein as "heteroaryl". For example, such groups include furyl, tetrahydrofuryl, pyrrolyl, pyrrolidinyl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, triazolyl, thiazolyl, isothiazolyl, pyrazolyl, pyrazolidinyl, oxadiazolyl, thiadiazolyl, imidazolyl, imidazolinyl, pyridyl, pyridazinyl, triazinyl, piperidinyl, morpholinyl, thiomorpholinyl, pyrazinyl, piperazinyl, pyrimidinyl, naphthyridinyl, benzofuranyl, benzothienyl, indolyl, indolinyl, indolizinyl, indazolyl, quinolizinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, pteridinyl, quinuclidinyl, carbazolyl, acridiniyl, phenazinyl, phenothiazinyl, phenoxazinyl, purinyl, benzimidazolyl, benzthiazolyl, and benzoxazolyl.
The above heterocyclic groups may further include one or more substituents at one or more carbon and/or non-carbon atoms of the heteroaryl group, e.g: alkyl; aryl; heterocycle; halogen; nitro; cyano; hydroxyl, alkoxyl or aryloxyl; thio or mercapto, alkyl- or arylthio; amino, alkyl-, aryl-, dialkyl- diaryl-, or arylalkylamino; aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl or arylalkylaminocarbonyl; carboxyl, or alkyl- or aryloxycarbonyl; carboxaldehyde, or aryl- or alkylcarbonyl; iminyl, or aryl- or alkyliminyl; sulfo; alkyl- or arylsulfonyl; hydroximinyl, or aryl- or alkoximinyl; carbamido; or thiocarbamido. In addition, two or more alkyl substituents may be combined to form fused heterocycle-alkyl or heterocycle-aryl ring systems. Substituents including heterocyclic groups (e.g., heterocycleoxy, heteroaryloxy, and heteroaralkylthio) are defined by analogy to the above-described terms.
5.1.14 Heterocyclealkyl
The term "heterocyclealkyl" refers to a heterocycle group that is joined to a parent structure by one or more alkyl groups as described above, e.g., 2-piperidylmethyl, and the like. The term "heteroaralkyl" as used herein refers to a heteroaryl group that is joined to a parent structure by one or more alkyl groups as described above, e.g., 2-thienylmethyl, and the like.
5.2 Electroluminescent Devices
In another aspect, the present invention provides electroluminescent devices. In one embodiment, shown in FIG. 3, an organic electroluminescent device comprises first and second electrodes 302, 304 and a single conductive electroluminescent layer 306 that is electroluminescently conductively coupled directly with the first and second electrodes. In a more particular embodiment, electroluminescent layer 306 is comprised of an organic electroluminescent material that includes silicon-oxygen bonds and is described in greater detail in Section 5.3 below. In a more particular embodiment, the first electrode is a cathode and the second electrode is an anode. Electric contacts 308 and 310 can be attached to the electrodes. Finally, the entire device 15 can be driven by an electrical source 312. Another embodiment, shown FIG. 4, comprises first electrode 402, second electrode, 404, a conductive light-emitting layer 406 that is electroluminescently conductively coupled directly with the first and second electrodes. Electric contacts 408 and 410, and an electrical source 412. In this embodiment, a substrate 414 is coupled with electrode 402.
The electrode can be made from any materials known in the electronics and solid state device arts for making electrodes. Such materials can be selected from electrically conductive metals (such as gold (Au), silver (Ag), copper (Cu), aluminum (Al), indium (In), magnesium (Mg), sodium (Na), potassium (K), and the like), or alloys of these electrically conductive metals (such as Mg--Ag, and Mg--In). Useful electrode materials also include conducting oxides (e.g., zinc oxide, stannic oxide, indium oxide, ITO (indium tin oxide), or conducting composite materials (e.g., silver-containing borosilcate glass, silver-containing epoxy resins, silicon rubber, and silver). Still other materials will be familiar to those of skill in the electronics and solid-state device arts. If the first electrode is also to be used as a light-emitting surface, an electrode material such as ITO or gold can be used to increase the transmittance of light emitted from the luminescent layer. Deposition thicknesses of between about 10 nanometers (nm) and about 1000 nm may be used. More specific thicknesses include those between about 50 nm and about 500 nm. Still more specific thicknesses are those between about 100 nm and about 400 nm. Even more specific thicknesses include those between about 200 nm and about 300 nm.
The first electrode may act as the anode or the cathode. In one embodiment, if the first electrode is used as the anode, then the second (opposite) electrode is fabricated from an electrically conductive material having work function larger than the work function of the first electrode. Conversely, if the first electrode is used as the cathode, then the second (opposite) electrode is made from an electrically conductive material having a work function smaller than the work function first electrode. In more specific embodiments, the anode has a work function of at least about 4 electron volts ("eV"); and the cathode material has a work function of less than about 4 eV.
The first electrode can be formed using any of the techniques known in the art of fabricating solid-state electronic devices. Examples of such methods include, but are not limited to, the following. Physical vapor deposition, including resistance heating, electron beam heating, high frequency induction heating, reactive vapor deposition, molecular beam epitaxy, hot wall vapor deposition, ion plating, or ionized cluster beam methods. Sputtering methods, including diode sputtering, diode magnetron sputtering, triode and tetrode plasma sputtering, reactive sputtering, ionized beam sputtering, and combinations of such methods. Casting methods, in which a precursor molecule is dissolved in an appropriate solvent (e.g., chloroform, tetrahydrofuran, benzene, toluene, xylene, or mesitylene) and then cast onto a surface to create a film. The film can be further hardened by placing the device in an oven (under vacuum or a controlled atmosphere) for 10 minutes-24 hours at 30� C.-100� C. Spin casting, in which a suitable amount of a solution as described for casting is dropped onto a surface. The surface is rotated at about 100 revolutions-per-minute ("rpm") about 20,000 rpm for a period of between about 5 seconds ("s") and about 200 s. The resulting film is then dried as described. These steps can be repeated using different solutions to form a laminate structure. The amounts of materials, solutions, methods for deposition will depend on various factors well-known among those of skill in the solid-state electronic device arts.
The second electrode can be formed using the methods and materials just described with respect to the first electrode. In one embodiment, the second electrode is formed directly on the electroluminescent layer. In one embodiment, the second electrode is effective to prevent substantially any crystallization of the electroluminescent layer such that the layer retains a substantially amorphous structure that reduces any natural quenching of the layer's luminescence during operation of the device.
In some embodiments, a substrate is included. In one embodiment, the substrate comprises a substantially transparent or substantially semi-transparent to allow light created by the organic light emitting material to be emitted from the device. Examples of suitable materials include glass, plastic, quartz, ceramic, and silicon. The choice of materials and methods of fabrication will be familiar among those of skill in the solid-state device and electronics arts.
5.3 Organic Electroluminescent Materials
The electroluminescent material, such as illustrated at 304 in FIG. 3 and 404 in FIG. 4, comprises, in one embodiment, an organo-siloxane polymer having the basic structure shown below (Compound 1) in which the organic constituents of the organo-siloxane polymer are included in the main chain of the polymer. ##STR6## In Compound 1, R and R' can be identical or different as described hereinbelow. In one embodiment, R and R' independently are anthracene and pentacene. The anthracene or pentacene component of the organo-siloxane polymer each can be substituted optionally with a substituent selected independently from the group consisting of: hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkythio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, sulfonyl, sulfonyloxy, alkyl bonded to the adjacent silicon atom of the organo-siloxane polymer, aryl bonded to the adjacent silicon atom of the organo-siloxane polymer, or the adjacent silicon atom of said organo-siloxane polymer. One or both of the adjacent silicon atoms of the organo-siloxane polymer must be attached directly to the anthracene or pentacene component of the organo-siloxane polymer, or to one or both of the substituents, depending on the chemical compatibility of the substituent(s) and the silicon atom, such that the anthracene or pentacene is coupled with the main chain of the organo-siloxane polymer. Such compatibility will be recognized by those of skill in the synthetic organic chemical arts.
In one embodiment of Compound 1, the main-chain siloxane polymer includes the anthracene derivative shown as Compound 2 below. ##STR7## R1 -R10 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkylthio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, 15 sulfonyl, sulfonyloxy, alkyl bonded to the adjacent silicon atom of the organo-siloxane polymer, aryl bonded to the adjacent silicon atom of the organo-siloxane polymer, or the adjacent silicon atom of said organo-siloxane polymer. The adjacent silicon atoms of the organo-siloxane polymer must be attached directly to the anthracene ring structure and/or one or both of the substituents R1 -R10, depending on the chemical compatibility of the substituent and the silicon atom, in any combination sufficient to couple Compound 2 to the main chain of the organo-siloxane polymer. Such compatibility will be recognized by those of skill in the synthetic organic chemical arts.
In one particular embodiment, two substituents are coupled with the adjacent silicon atoms of the main chain. In a more particular embodiment, these two substituents are located symmetrically on the anthracene molecule (e.g., R1 and R4, R2 and R7, or R5 and R10). In a more particular embodiment, at least one of the substituents is an alkylene group. In a still more particular embodiment, the alkylene group has the general formula --CH2 (CH2)m CH2 --, where m is an integer between 1 and 4. Still more particularly, m is 1, i.e., the substituent is trimethylene: --CH2 CH2 CH2 --.
In yet another particular embodiment, the silicon-coupled substituents are identical. More particular embodiments are those for which the two substituents are R5 and R10, where R5 ═R10 and R1 -R4 and R6 -R9 are chosen from the group listed above with respect to Compound 2. Still more particular embodiments are those embodiments just recited for which R5 and R10 are the same alkylene moiety. Yet more particular embodiments are those for which the alkylene moiety is of the general formula --CH2 (CH2)m CH2 --, and, more particularly, where m is an integer between 1 and 4. One particular embodiment having useful electroluminescent properties is that embodiment for which R5 and R10 each are --CH2 CH2 CH2 --, and R1 -R4 and R6 -R9 each are hydrogen. This compound has the structure shown below (Compound 3). ##STR8##
In another embodiment of Compound 1, the main-chain siloxane polymer includes the pentacene derivative shown as Compound 4 below. ##STR9## R21 -R34 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkylthio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, sulfonyl, sulfonyloxy, alkyl bonded to the adjacent silicon atom of the organo-siloxane polymer, aryl bonded to the adjacent silicon atom of the organo-siloxane polymer, or the adjacent silicon atom of said organo-siloxane polymer. The adjacent silicon atoms of the organo-siloxane polymer must be attached directly to the anthracene ring structure and/or one or both of the substituents R21 -R34, depending on the chemical compatibility of the substituent and the silicon atom, in any combination sufficient to couple Compound 4 to the main chain of the organo-siloxane polymer. Such compatibility will be recognized by those of skill in the synthetic organic chemical arts.
In one particular embodiment, two substituents are coupled with the adjacent silicon atoms of the main chain. In a more particular embodiment, these two substituents are located symmetrically on the pentacene molecule (e.g., R22 and R29 or R26 and R33). In a more particular embodiment, at least one of the substituents is an alkylene group. In a still more particular embodiment, the alkylene group has the general formula --CH2 (CH2)m CH2 --, where m is an integer between 1 and 4. Still more particularly, m is 1, i.e., the substituent is trimethylene: --CH2 CH2 CH2 --.
In yet another particular embodiment, the silicon-coupled substituents are identical. More particular embodiments are those for which the two substituents are R26 and R33, where R26 ═R33 and R34 -R25 and R27 -R32 are chosen from the group listed above with respect to Compound 4. Still more particular embodiments are those embodiments just recited for which R26 and R33 are the same alkylene moiety. Yet more particular embodiments are those for which the alkylene moiety is of the general formula --CH2 (CH2)m CH2 --, and, more particularly, where m is an integer between 1 and 4. One particular embodiment having useful electroluminescent properties is that embodiment for which R26 and R33 each are --CH2 CH2 CH2 --, and R34 -R25 and R27 -R32 each are hydrogen. This compound has the structure shown below (Compound 5). ##STR10##
The above-described compounds can be made using methods known among those of skill in the art of organic chemistry and materials science arts. In general, the substituents for both Compound 2 and Compound 4 will be chosen to provide desired electronic and mechanical properties. The choice of substituent or combination of substitutents will depend at least in part upon the emission color, electrical, and optical properties required of the intended device. Such choices can be made by considering various well-known chemical properties including, but not limited to, steric factors, electron-withdrawing effects, electron-donating effects, and resonance effects. Often such properties can be estimated, e.g., using chemical modeling software or published parameters. Many such properties can be determined empirically using standard methods and materials. For example, the organo-siloxane polymer described above (Compound 1) can be formed from anthracene or pentacene optionally substituted as just described and including at least one reactive silyl group that is effective to form siloxane bonds. Examples of such reactive silyl groups include trialkoxysilyl, dialkoxysilyl, trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy. In more particular embodiments, the present invention provides the following precursors (Compound 6 and Compound 7). ##STR11## R40 -R43 and R44 -R47, and R50 -R55 and R56 -R61 are selected independently from the group consisting of hydrogen, alkyl, aryl, heteroalkyl, heteroaralkyl, nitro, cyano, hydroxy, alkoxy, aryloxy, thio, alkythio, arylthio, amino, halogen, dialkylamino, diarylamino, diaralkylamino, arylamino, alkylamino, arylalkylamino, carbonyloxy, carbonylalkoxy, carbonylalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxylcarbonyloxy, sulfonyl, sulfonyloxy. R48, R49, R42, and R63 are selected independently from the group consisting of trialkoxysilyl, dialkoxysilyl, trichlorosilyl, dichlorosilyl, heptachlorotrisiloxy, and pentachlorodisiloxy. In one embodiment, R40 -R47 and R50 -R61 are as just described, and R48, R49, R62, and R63 each are trichlorosilyl. In a more specific embodiment, R40 -R47 and R50 -R61 are each hydrogen and R48, R49, R62, and R63 each are trichlorosiyl.
For example, the synthesis of Compound 3 from 9,10-bis(3-trichlorosilylpropyl)anthracene (Compound 6 where R40 -R47 and R50 -R61 are each hydrogen, and R48, and R49 each are trichlorosiyl section 6.1. The general synthetic route is outlined in FIG. 1 below. ##STR12## In step A, commercially-available anthraquinone 1 (Aldrich Chemical Co., Madison Wis.) is reacted with allyl magnesium bromide (CH2 CHCH2 MgBr, also available commercially from Aldrich) in dry ether to form addition product 2. Product 2 is dehydrated using phenylhydrazine and acetic acid (B). The resulting bis-allylanthracene 3 is reacted with trichlorosilane (HSiCl3) and H2 PtCl6.H2 O in dry benzene (C) to give the desired final hydrosilation product 4. The pentacene analog can be made using the same synthetic pathway. In general, product 4--the anti-Markovnikov product--is the dominant species. However, it will be appreciated by those of skill in the organic chemistry arts that other alkenes will likely give both Markovnikov as well as anti-Markovnikov hydrosilation products. Nevertheless, both the Markovnikov and anti-Markovnikov addition products can be incorporated into the organo-siloxane polymers of the invention, either in combination or individually after isolation using known methods and materials.
In still other embodiments, the main-chain silicon atoms or the organo-siloxane polymer having the general structure shown above as Compound I will be cross-linked with the silicon atoms of other such organo-siloxane polymer chains to form two- and three-dimensional organo-siloxane networks. In more particular embodiments, the cross-links are made by oxygens atom to provide siloxane cross-links. Other cross-links can be formed using atoms or molecules that impart desired mechanical and electronic properties to the matrix, such as, for example, methylene (--CH2 --) or oxymethyleneoxy (--O--CH2 --O--). Still other cross-linking agents will be familiar to those of skill in the organic chemical and materials science arts.
The electroluminescent material can further be doped with a hole transport material, an electron transport material, an organic or inorganic dye, or a combination of such materials/dyes to alter the color and enhance the light emitting quality of the luminescent organic-inorganic hybrid material. Examples of dopants include porphyrins or aromatic tertiary amines, both of which are known as hole transport agents. Examples of dopants that fimction as electron transport agents include oxadiazole derivatives such as described in U.S. Pat. No. 5,276,381, which is incorporated reference above, or thiadiazole derivatives, such as disclosed in U.S. Pat. No. 5,336,546, also incorporated by reference above. Examples of suitable dyes include perylene, coumarin, and rhodamine or a rhodamine salt such as rhodamine perchlorate. Again, the choice of materials and their preparation can be accomplished using techniques well known in the organic chemical and materials science arts.
The electroluminescent layer can be formed by standard methods including, but not limited to, physical vapor deposition methods, sputtering, spin-coating, or solution casting. The layer may be formed directly on the first electrode (see Sections 6.3.1 and 6.3.2). In addition, the layer can be doped with a hole transport material, an electron transport material, an organic dye, and/or a combination of the above to enhance it's performance (see Section 6.3.3).
Generally, following deposition, the material is reacted in a humid atmosphere or open air to cure the electroluminescent layer under conditions allowing thermodynamic control of product formation. In one embodiment, the material is exposed to about 100% humidity for about 5 minutes to about 10 minutes and is heated at about 110� C. for about 15 minutes. In another embodiment, the material is exposed to ambient atmospheric moisture prior to heating at 110� C. for about 15 minutes. Still other combinations of reaction conditions will be apparent to those of skill in the organic chemical and materials science arts.
Without wishing to be bound to any particular theory of action, it is believed the chemical reaction of the above-mentioned reactive silyl groups of the organic component of the organo-siloxane polymer (e.g., the above-described trichlorosilyl or trialkoxysilyl groups) with moisture creates an interlocking organic-inorganic hybrid polymeric material comprising silicon-oxygen bonds (e.g., --Si--O--Si--). Generally, water displaces the chloride or alkoxide group to form a hydroxysilane. The hydroxysilane moiety reacts again to displace another chlorine-silicon or alkoxy-silicon bond to form the siloxane network. This reaction sequence is illustrated in FIG. 5A, in which a bis(trichlorosilyl) organic component 502 reacts with water in a first step to form an hydroxysilyl derivative 504. The intermediate reacts with additional trichlorosilyl starting material in a second step to form an organo-siloxane polymer intermediate 506. Thus, those of skill in the organic chemistry arts that the Si--Cl bonds of the starting material 502 do not undergo condensation. Further reaction and cross-linking provides organo-siloxane polymer network 508. Alternatively, as illustrated in FIG. 5B, starting material 502 can be reacted with a hydroxylated surface 510 to form, upon reaction with additional starting material, a substrate-bound organo-siloxane polymer network 512.
6 EXAMPLES The following Examples are provided to illustrate certain aspects of the present invention and to aid those of skill in the art in the art in practicing the invention. These Examples are in no way to be considered to limit the scope of the invention in any manner.
6.1 Synthesis of Light-Emitting Layer Precursors
6.1.1 9,1 0-Diallylanthracene
A solution of allylmagnesium bromide was prepared by adding dropwise with vigorous stirring 40 ml of allyl bromide (Aldrich) dissolved in 100 ml of diethyl ether to a mixture of 50 g of magnesium turnings in 300 ml of anhydrous ether. The mixture was stirred for 2 hours following the addition, and the ethereal solution was then transferred to a reaction flask. This flask and transferred solution was cooled to 0� C., and 20 g of anthraquinone (Aldrich) was added in 500 mg portions. The anthraquinone/allyl magnesium bromide solution was stirred for 14 h and then warmed slowly to room temperature. The temperature of the reaction mixture was reduced to 0� C., and then ice was added to the mixture until a yellow ether solution was formed. This solution was separated from the rest of the reaction mixture and reduced in vacuo until a white precipitate formed. The precipitate was washed with petroleum ether and dried in vacuo. The solid was mixed with 6 ml of phenylhydrazine and 26 ml of glacial acetic acid and then was heated at 40� C. for 2 hours, refluxed for 30 minutes, and then cooled to room temperature over a period of 12 hours. A yellow powder precipitated from the reaction mixture. The powder was recrystallized from acetic acid and ethanol. Characterization: Elemental Analysis (Theory (Found)): C:93.02 (92.75), H: 6.98 (7.10).
6.1.2 9,10-Bis(trichlorosilylpropyl)anthracene
1 g of 9,1 0-Diallylanthracene (prepared as described in Section 6.1.1 above) was dissolved in 20 ml of dry toluene. A single crystal of hydrogen hexachloroplatinum was added to the solution, followed by 1 ml of trichlorosilane. The mixture was stirred at 40� C. for 9 hours after which time the volatile components were removed in vacuo. The remaining solid was sublimed, yielding a yellow solid having the following mass spectrographic characteristic: MS (M+): 578. 1 H NMR (200 MHz, C6 D6): 8.12 (dd, 4H, J=10.4 Hz); 7.34 (dd, 4H, J=10.1 Hz); 3.34 (t, 4H, J≈8.14 Hz); 1.85 (tt, 4H, J=8.14 Hz); 1.09 (t, 4H, 8.3 Hz).
6.2 Preparation of the Device Substrate
A sheet of indium-tin oxide-coated glass (7"�7", Donnally) was cut into 1"�1" squares. Each of the squares was sonicated for 10 minutes in successive baths of acetone, methanol, and reverse osmosis de-ionized water. The squares were then dried at 110� C. for 12 hours prior to use.
6.3 Device Construction
6.3.1 Devices of Structure 1
A surface layer of 9,1 0-bis(trichlorosilylpropyl)anthracene having a thickness of about 100 nm was deposited onto a clean ITO substrate (see Section 6.2) by resistive heating at a rate of about 0.2 nm/sec at a pressure of about 10-6 Torr. The anthracene layer was then exposed to ambient atmosphere for about 15 minutes and then heated to 110� C. for about 30 minutes. A 300 nm layer of magnesium metal (Cerac) was deposited over the bis(trichlorosilylpropyl)anthracene layer by resistive heating at a rate of about 0.5 nm/sec at a pressure of about 10-6 Torr. A pale violet emission having an approximate intensity of 100 cd/M2 emanated from the device upon application of 12 V of direct current (DC).
6.3.2 Devices of Structure 2
An anhydrous solution of 9,10-bis(trichlorosilylpropyl)anthracene in xylene (1% by weight) was spun-cast onto a clean ITO substrate (prepared as described in Section 6.2) at 2,000 revolutions-per-minute ("rpm") for 60 seconds ("s"). The coated substrate was placed in a humidity chamber have an ambient humidity of 100% and a temperature of 25� C. for 15 minutes ("min"). The device was then heated to 110� C. for about 0.5 hours ("hrs.") A layer of magnesium metal (Cerac) was deposited by resistive heating over the bis(trichlorosilylpropyl)anthracene layer to a thickness of about 300 nm at a rate of about 0.5 nm/s and a pressure of about 10-6 Torr. A pale violet emission aving an intensity of about 100 cd/m2 was observed upon the application of a 12 V DC current to he device.
6.3.3 Devices of Structure 3
An anhydrous solution of 9,10-bis(trichlorosilylpropyl)anthracene in xylene (1% by weight) and traphenylporphyrin (0.1% by weight) was spun-cast onto a clean ITO substrate (prepared as scribed in Section 6.2) at 4,000 rpm for 30 s. The coated substrate was place in a humidity chamber have an ambient humidity of 100% and a temperature of 25� C. for 15 min. The device was then heated to 110� C. for about 0.5 hrs. A layer of magnesium metal (Cerac) was deposited by resistive heating over the bis(trichlorosilylpropyl)anthracene/tetraphenylporphyrin layer to a thickness of about 300 nm at a rate of about 0.5 nm/s and a pressure of about 10-6 Torr. A pale violet emission having an intensity of about 100 cd/M2 was observed upon the application of a 8 V DC current to the device.
6.3.4 Devices of Structure 4
An anhydrous solution of 9,10-bis(trichlorosilylpropyl)anthracene in xylene (1% by weight) and coumarin 6 (1% by weight) was spun-cast onto a clean ITO substrate (prepared as described in Section 6.2) at 4,000 rpm for 30 s. The coated substrate was place in a humidity chamber have an ambient humidity of 100% and a temperature of 25� C. for 5 min. The device was then heated to 110� C. for about 1 hour. A layer of magnesium metal (Cerac) was deposited by resistive heating over the bis(trichlorosilylpropyl)anthracene/coumarin 6 layer to a thickness of about 150 nm at a rate of about 2 nm/s and a pressure of about 10-6 Torr. A green emission having an intensity of about 100 cd/m2 was observed upon the application of a 5 V DC current to the device.
6.3.5 Devices of Structure 5
An anhydrous solution of 9,10-bis(trichlorosilylpropyl)anthracene in tetrahydrofuran (1% by weight) and rhodamine perchlorate (1% by weight) was spun-cast onto a clean ITO substrate (prepared as described in Section 6.2) at 4,000 rpm for 30 s. The coated substrate was place in a humidity chamber have an ambient humidity of 100% and a temperature of 25� C. for 5 min. The device was then heated to 110� C. for about 1 hour. A layer of magnesium metal (Cerac) was deposited by resistive heating over the bis(trichlorosilylpropyl)anthracene/rhodamine layer to a thickness of about 150 nm at a rate of about 2 nm/s and a pressure of about 10-6 Torr. A red emission having an intensity of about 30 cd/m2 was observed upon the application of a 5 V DC current to the device.
6.3.6 Devices of Structure 6
An anhydrous solution of 9,10-bis(trichlorosilylpropyl)anthracene in xylene (1% by weight) and perylene (1% by weight) was spun-cast onto a clean ITO substrate (prepared as described in Section 6.2) at 4,000 rpm for 30 s. The coated substrate was place in a humidity chamber have an ambient humidity of 100% and a temperature of 25� C. for 5 min. The device was then heated to 110� C. for about 1 hour. A layer of magnesium metal (Cerac) was deposited by resistive heating over the bis(trichlorosilylpropyl)anthracene/perylene layer to a thickness of about 150 nm at a rate of about 2 nm/s and a pressure of about 10-6 Torr. A green emission having an intensity of about 30 cd/m2 was observed upon the application of a 5 V DC current to the device.
Thus, the present invention will be seen to provide a light-weight, durable, efficient electroluminescent device. Such devices can be used in a wide variety of applications in consumer and military electronics, such as computers and visual display terminals.
Although certain embodiments and examples have been used to describe the present invention, it will be apparent to those having skill in the art that various changes can be made to those embodiment and/or examples without departing from the scope or spirit of the present invention. For example, other substituents having similar electronic and steric properties can be used in addition to those exemplified herein without departing from the scope of the invention. A wide variety of processing techniques can be used to provide the cross-linked siloxane network provided by the present invention.
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(No month).145Fluorine Tin Oxide as an Alternative to Indium Tin Oxide in Polymer LEDs, Annica Anderson, Nicklas Johannson, Per Broms, Nu Yu, Donald Lupo, and William R. Salaneck, 1998, pp. 859-863, Adv. Mater. 10(11). (No month).146Glass Substrates for Flat Panel Displays, D.M. Moffatt, MRS Bulletin/Mar. 1996, vol. 21, No. 3, pp. 31-34.147Green Electroluminescent Emission from Substituted Polyacetylenes, Runguang Sun, Toshio Masuda, and Takayoshi Kobayashi, Jpn. J. Appl. Phys. vol. 35, pp. 1434-1437, Nov. 1, 1996.148 *Growth of dark spots by interdiffusion across organic layers in organic electroluminescent devices, Masamichi Fujihara, Lee Mi Do, Amane Koike and Eun Mi Han, Department of Biomolecular Engineering, Tokyo Institute of Technology, Appl. Phys. Lett. 68(12), Mar. 25, 1996, pp. 1787 1789.149Growth of dark spots by interdiffusion across organic layers in organic electroluminescent devices, Masamichi Fujihara, Lee-Mi Do, Amane Koike and Eun-Mi Han, Department of Biomolecular Engineering, Tokyo Institute of Technology, Appl. Phys. Lett. 68(12), Mar. 25, 1996, pp. 1787-1789.150 *Height of the energy barrier existing between cathodes and hydroxyquinoline aluminum complex of organic electroluminescence devices, Michio Matsumura, Tomonori Akai, Masayuki Saito, and Takashi Kimura, Research Center for Photoenergetics of Organic Materials, Osaka University, J. Appl. Phys. 79(1), Jan. 1, 1996, pp. 264 268.151Height of the energy barrier existing between cathodes and hydroxyquinoline-aluminum complex of organic electroluminescence devices, Michio Matsumura, Tomonori Akai, Masayuki Saito, and Takashi Kimura, Research Center for Photoenergetics of Organic Materials, Osaka University, J. Appl. Phys. 79(1), Jan. 1, 1996, pp. 264-268.152 *High Electron Affinity Polymers for LEDs, Moratti, Cervini, Holmes, Baigent, Friend, Greenbaum, Gr u ner and Hamer, University of Cambridge, Synthetic Metals 71, 1995, pp. 2117 2120. (No month).153High Electron Affinity Polymers for LEDs, Moratti, Cervini, Holmes, Baigent, Friend, Greenbaum, Gruner and Hamer, University of Cambridge, Synthetic Metals 71, 1995, pp. 2117-2120. (No month).154High Peak Brightness Polymer Light-Emitting Diodes, Adv. Mater. 1998, vol. 10, No. 1, pp. 64-68. (No month).155High Peak Brightness Polymer Light-Emitting Diodes, Nir Tessler, Nick T. Harrison, and Richard H. Friend, 1998, pp. 64-68, Adv. Mater. 10(1). (No month).156 *Highly efficient and bright organic electroluminescent devices with an aluminum cathode, G. E. Jabbour, Y. Kawabe, S. E. Shaheen, J. F. Wang, M. M. Morrell, B. Kippelen and N. Peyghambarian, Optical Sciences Center, University of Arizona, Appl. Phys. Lett. 71(13), Sep. 29, 1997, pp. 1762 1764.157Highly efficient and bright organic electroluminescent devices with an aluminum cathode, G. E. Jabbour, Y. Kawabe, S. E. Shaheen, J. F. Wang, M. M. Morrell, B. Kippelen and N. Peyghambarian, Optical Sciences Center, University of Arizona, Appl. Phys. Lett. 71(13), Sep. 29, 1997, pp. 1762-1764.158 *Highly efficient blue electroluminescence from a distyrylarylene emitting layer with a new dopant. Chishio Hosokawa, Hisahiro Higashi, Hiroaki Nakamura, and Tadashi Kusumoto, Central Research Laboratories, Idemitsu Kosan Co., Ltd., pp. 3853 3855, Dec. 25, 1995, App. Phys. Lett. 67(26).159Highly efficient blue electroluminescence from a distyrylarylene emitting layer with a new dopant. Chishio Hosokawa, Hisahiro Higashi, Hiroaki Nakamura, and Tadashi Kusumoto, Central Research Laboratories, Idemitsu Kosan Co., Ltd., pp. 3853-3855, Dec. 25, 1995, App. Phys. Lett. 67(26).160Highly efficient electroluminescense of new wide band gap ladder-type poly(para-phenylenes), Tasch, Niko, Leising, Scherf, Appl. Phys. Lett. 68(8), Feb. 19, 1996, pp. 1090-1092.161Highly Efficient Light-Emitting Diodes with Microcavities, E.F. Schubert, N.E.J. Hunt, M. Micovic, R.J. Malik, D.L. Sivco, A.Y. Cho, G.J. Zydzik, Science, vol. 265, Aug. 12, 1994, pp. 943-945.162Highly Oriented Thin Films of a Substituted Oligo (para-phenylenevinylene) on Friction-Transferred PTFE Substrates, Richard E. Gill, Georges Hadziioannou, Phillipe Lang, Francis Garnier, and Jean Claude Wittmann, 1997, pp. 331-334, Adv. Mater. 9(4). (No month).163Hole-Transporting Compounds for Multi-Layer Polymer Light-Emitting Diodes, Kraft, Burn, Holmes, Synthetic Metals. 55-57 (1993) pp. 4163-4167. 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(No month).171Indium contamination from the indium-tin-oxide electrode in polymer light-emitting diodes, Schlatmann, Floet, Hilberer, Garten, Smulders, Klapwijk and Hadziioannou, Appl. Phys. Lett. 69(12), Sep. 16, 1996, pp. 1764-1766.172Injection, Transport and Recombination of Charge Carriers in Organic Light-emitting Diodes, Heinz Bassler, �1998 John Wiley & Sons, Ltd., pp. 402-418, Polymers for Advanced Technologies 9. (No month).173Ink-jet printing of doped polymers for organic light emitting devices, T.R. Hebner, C.C. Wu, D. March, M.H. Lu, and J.C. Sturm, pp. 519-521, Appl. Phys. Lett. 72(5), Feb. 2, 1998.174Insoluble Poly[2-(2'-ethylhexyloxy)-5-methoxy-1,4-phenylenevinylene] from Use in Multilayer Light-Emitting Diodes, Burn, Grice, Tajbakhsh, Bradley and Thomas, Adv. Mater. 1997, vol. 9, No. 15, pp. 1171-1174. (No month).175Integrated three-color organic light-emitting devices, C.C. Wu, J.C. Sturm and R.A. Register, M.E. Thompson, pp. 3117-3119, Appl. Phys. Lett. 69(21), Nov. 18, 1996.176Interchain Excitations in Conjugated Polymers, Yan, Rothberg, Kwock and Miller, Physical Review Letters, vol. 75, No. 10, Sep. 4, 1995, pp. 1992-1995.177 *Interference phenomenon determines the color in an organic light emitting diode, Thomas Granlund and Leif a. A. Pettersson, Department of Physics and Measurement Technology, Laboratory of Applied Physics, Link o ping University, Mats R. Anderson, Department or Organic Chemistry and Polymer Technology, Chalmers University of Technology, Olle Ingan a s, Department of Physics and Measurement Technology, Laboratory of Applied Physics, Link o ping University, J. Appl. Phys. 81(12), Jun. 15, 1997, pp. 8097 8103.178Interference phenomenon determines the color in an organic light emitting diode, Thomas Granlund and Leif a. A. Pettersson, Department of Physics and Measurement Technology, Laboratory of Applied Physics, Linkoping University, Mats R. 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Phys. 73(10), May 15, 1993, pp. 5177-5180.188Light-emitting diodes using n-type conducting polymer: Poly(p-pyridyl vinylene), Mitsuyoshi Onoda, Himeii Institute of Technology, J. Appl. Phys. 78(2), Jul. 15, 1995, pp. 1327-1333.189Light-Emitting Diodes, M. George Craford and Frank M. Steranka, �1994 VCH Publishers, Inc., pp. 485-515, Encyclopedia of Applied Physics, vol. 8. (No month).190List of Non-PPV Polymers, 2 pages, Source and date not given.191 *Lithium aluminum contacts for organic light emitting devices, E. I. Haskal, A. Curioni, P. F. Seidler and W. Andreoni, IBM Research Division, Zurich Research Laboratory, Appl. Phys. Lett. 71(9), Sep. 1, 1997, pp. 1151 1153.192Lithium-aluminum contacts for organic light-emitting devices, E. I. Haskal, A. Curioni, P. F. Seidler and W. Andreoni, IBM Research Division, Zurich Research Laboratory, Appl. Phys. Lett. 71(9), Sep. 1, 1997, pp. 1151-1153.193 *Low Molecular Weight and Polymeric Triphenylenes as Hole Transport Materials in Organic Two Layer LEDs, Andreas Bacher, Ingo Bleyl, Christian H. Erdelen, Dietrich Haarer, Wolfgang Paulus and Hans Werner Schmidt, Adv. Mater. 1997, 9, No. 13, pp. 1031 1035. (No month).194Low Molecular Weight and Polymeric Triphenylenes as Hole Transport Materials in Organic Two-Layer LEDs, Andreas Bacher, Ingo Bleyl, Christian H. Erdelen, Dietrich Haarer, Wolfgang Paulus and Hans-Werner Schmidt, Adv. Mater. 1997, 9, No. 13, pp. 1031-1035. (No month).195 *Low pressure organic vapor phase deposition of small molecular weight organic light emitting device structures, M. A. Baldo, V. G. Kozlov, P. E. Burrows and S. R. Forrest, Department of Electrical Engineering, Center for Photonics and Optoelectronic Materials, V. S. Ban, PD LD Incorporated, B. Koene and M. E. Thompson, Department of Chemistry, University of Southern California, Appl. 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(No month).208Metal oxides as a hole-injecting layer for an organic electroluminescent device, Shizuo Tokito, Koji Noda and Yasunori Taga, Toyota Central Research and Development Laboratories, Inc., pp. 2750-2753, �1996, Source not given. (No month).209Microcavity Effect in a Single-Layer Polymer Ligh-Emitting Diode, Wittmann, Gruner, Friend, Spencer, Moratti, Holmes, Adv. Mater. 1995, vol. 7, No. 6, pp. 541-544.210Microfabrication of an electroluminescent polymer light emitting diode pixel array, Noach, Faraggi, Cohen, Avny, Neumann, Davidov, Lewis, Appl. Phys. Lett. 69(24), Dec. 9, 1996, pp. 3650-3652.211Microlithographic Process for Patterning Conjugated Emissive Polymers, Michelle L. Renak, Guillermo C. Bazan, and Daniel Roitman, 1997, pp. 392-395, Adv. Mater. 9(5). (No month).212MicroPatent� Patent Search: Patent List for "cambridge display technology"--Abstracts of 37 patents, Sep. 1998.213MicroPatent� Patent Search: Patent List for "organic electroluminescence"--Abstracts of 80 patents, Sep. 1998.214MicroPatent� Patent Search: Patent List for "organic light emitting" not "organic electroluminescent"--Abstracts of 60 patents, Sep. 1990.215MicroPatent� Patent Search: Patent List for "organic luminescent"--Abstracts of 238 patents, Sep. 1998.216 *Micropatterning Method for the Cathode of the Organic Electroluminescent Device, Kenichi Nagayama, Takashi, Yahagi, Hitoshi Nakada, Teruo Tohma, Teruichi Watanabe, Kenji Yoshida and Satoshi Miyaguchi, Tohoku Pioneer Electronic Corporation, Corporate R & D. Laboratories, Pioneer Electronic Corporation, Jpn. J. Appl. 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Lett. 66(20).220 *Multilayer White Light Emitting Organic Electroluminescenct Device, Junji Kido, Masato Kimura, Katsutoshi Nagai, Science , Vo. 267, Mar. 3, 1995, pp. 1332 1334.221Multilayer White Light-Emitting Organic Electroluminescenct Device, Junji Kido, Masato Kimura, Katsutoshi Nagai, Science, Vo. 267, Mar. 3, 1995, pp. 1332-1334.222 *Multilayered organic electroluminescent device using a novel starburst molecule, 4.4 , 4 tris (3 methylphenylamino) triphenylamine, as a hole transport material, Yasuhiko Sirota, Yoshiyuki Kuwabara, and Hiroshi Inada, Department of Applied Chemistry, Faculty of Engineering, Osaka University, Takeo Wakimoto, Hitoshi Nakada, Yoshinobu Yonemoto, Shin Kawami, and Kunio Imai, Corporate R&D Laboratory, Pioneer Electronic Corporation, pp. 807 809, Aug. 15, 1994, Appl. Phys. Lett. 65(7).223Multilayered organic electroluminescent device using a novel starburst molecule, 4.4', 4"-tris (3-methylphenylamino) triphenylamine, as a hole transport material, Yasuhiko Sirota, Yoshiyuki Kuwabara, and Hiroshi Inada, Department of Applied Chemistry, Faculty of Engineering, Osaka University, Takeo Wakimoto, Hitoshi Nakada, Yoshinobu Yonemoto, Shin Kawami, and Kunio Imai, Corporate R&D Laboratory, Pioneer Electronic Corporation, pp. 807-809, Aug. 15, 1994, Appl. Phys. Lett. 65(7).224New LEDs Based on Soluble Poly(2,6-Naphthylenevinylene), 1996, pp. 663-666, Adv. Mater. 8(8). (No month).225New Organic Electron-Transporting Materials for LEDs Strukelj and Miller, Source and date not given pp. 457-458.226 *Novel Blue Electroluminescent Polymers with Well Defined Conjugation Length, Taehyoung Zyung, Do Hoon Hwang, In Nam Kang, Hong Ku Shim, Wol Yon Hwang and Jang Joo Kim, Electronics and Telecommunications Research Institute, Chem. Mater. 1995, 7, pp. 1499 1503. (No month).227Novel Blue Electroluminescent Polymers with Well-Defined Conjugation Length, Taehyoung Zyung, Do-Hoon Hwang, In-Nam Kang, Hong-Ku Shim, Wol-Yon Hwang and Jang-Joo Kim, Electronics and Telecommunications Research Institute, Chem. Mater. 1995, 7, pp. 1499-1503. (No month).228 *Novel hole transporting materials based on triphenylamine for organic electroluminescent devices, Hiromitsu Tanaka, Shizuo Tokito, Yasunori Taga and Akane Okada, Toyota Central R & D Labs, Inc., Chem. Commun. , 1996, pp. 2175 2176 (No month).229Novel hole-transporting materials based on triphenylamine for organic electroluminescent devices, Hiromitsu Tanaka, Shizuo Tokito, Yasunori Taga and Akane Okada, Toyota Central R & D Labs, Inc., Chem. Commun., 1996, pp. 2175-2176 (No month).230Novel PPV Derivatives Emitting Light over a Broad Wavelength Range, Prof. J. I. Jin, S.J. Chung, K.K. Kim, 1997, pp. 551-554, Adv. Mater. 9(7). (No month).231 *Observation of Crystallization of Vapor deposited TPD Films by AFM and FFM, Eun mi Han, Lee mi Do, Yasuro Niidome and Masamichi Fujihira, Department of Biomolecular Engineering, Tokyo Institute of Technology, Chemistry Letters, 1994 The Chemical Society of Japan, pp. 969 970. (No month).232Observation of Crystallization of Vapor-deposited TPD Films by AFM and FFM, Eun-mi Han, Lee-mi Do, Yasuro Niidome and Masamichi Fujihira, Department of Biomolecular Engineering, Tokyo Institute of Technology, Chemistry Letters, �1994 The Chemical Society of Japan, pp. 969-970. (No month).233 *Observation of degradation processes of Al electrodes in organic electroluminescence devices by electroluminescence microscopy, atomic force microscopy, scanning electron microscopy, and Auger electron spectroscopy , L. M. Do, e. M. Han, Y. Niidome and M. Fujihira, Department of Biomolecular Engineering, Tokyo Institute of Technology, T. Kanno, S. Yoshida, A. Maeda and A. J. Ikushima, Materials Research Laboratory, HOYA Corporation, J. Appl. Phys. 6(9), Nov. 1, 1994, pp. 5118 5121.234Observation of degradation processes of Al electrodes in organic electroluminescence devices by electroluminescence microscopy, atomic force microscopy, scanning electron microscopy, and Auger electron spectroscopy , L. M. Do, e. M. Han, Y. Niidome and M. Fujihira, Department of Biomolecular Engineering, Tokyo Institute of Technology, T. Kanno, S. Yoshida, A. Maeda and A. J. Ikushima, Materials Research Laboratory, HOYA Corporation, J. Appl. Phys. 6(9), Nov. 1, 1994, pp. 5118-5121.235On the Conjugation Length in Poly(para-phenylene)-Type Polymers, Grimme, Kreyenschmidt, Uckert, Mullen and Scherf, Adv. Mater. 1995, 7, No. 3, pp. 292-294. (No month).236Operating stability of light-emitting polymer diodes based on poly(p-phenylene vinylene), J.C. Carter, I. Grizze, S.K. Heeks, D.J. Lacey, S.G. Latham, P.G. May, O. Ruiz de los Panos, K. Pichler, C.R. Towns, and H.F. Wittmann, pp. 34-36, Appl. Phys. Lett. 71(1), Jul. 7, 1997.237 *Optically pumped blue organic semiconductor lasers, V. G. Kozlov, G. Parthasarathy, P. E. Burrows and S. R. Forrest, Department of Electrical Engineering and the Princeton Material Institute, Center for Photonocs and Optoelectronic Materials, Princeton University, Y. You and M. E. Thompson, Department of Chemistry, University of Southern California, Appl. Phys. Lett. 72(2), Jan. 12, 1998, pp. 144 146.238Optically pumped blue organic semiconductor lasers, V. G. Kozlov, G. Parthasarathy, P. E. Burrows and S. R. Forrest, Department of Electrical Engineering and the Princeton Material Institute, Center for Photonocs and Optoelectronic Materials, Princeton University, Y. You and M. E. Thompson, Department of Chemistry, University of Southern California, Appl. Phys. Lett. 72(2), Jan. 12, 1998, pp. 144-146.239 *Organic electroluminescence cells based on this films deposited by ultraviolet laser ablation, N. Matsumoto, H. Shima, T. Fujii and F. Kannan, Appl. Phys. Lett. 71(17), Oct. 27, 1997, pp. 2469 2471.240Organic electroluminescence cells based on this films deposited by ultraviolet laser ablation, N. Matsumoto, H. Shima, T. Fujii and F. Kannan, Appl. Phys. Lett. 71(17), Oct. 27, 1997, pp. 2469-2471.241 *Organic electroluminescent device having a hole conductor as an emitting layer, Chihaya Adachi, Tetsuo Tsutsui and Shogo Saito, Department of Materials Science and Technology, Graduate School of Engineering Sciences, Kyusha Univeristy, Appl. Phys. Lett. 55(15), Oct. 9, 1989, pp. 1489 1491.242Organic electroluminescent device having a hole conductor as an emitting layer, Chihaya Adachi, Tetsuo Tsutsui and Shogo Saito, Department of Materials Science and Technology, Graduate School of Engineering Sciences, Kyusha Univeristy, Appl. Phys. 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(No month).260 *Organic solid state lasers with imprinted gratings on plastic substrates, M. Berggren, A. Dodabalapur, R. E. Slusher, A. Timko and O. Nalamasu, Bell Laboratories, Lucent Technologies, Appl. Phys. Lett. 72(4), Jan. 26, 1998, pp. 410 411.261Organic solid-state lasers with imprinted gratings on plastic substrates, M. Berggren, A. Dodabalapur, R. E. Slusher, A. Timko and O. Nalamasu, Bell Laboratories, Lucent Technologies, Appl. Phys. Lett. 72(4), Jan. 26, 1998, pp. 410-411.262Organic-inorganic heterojunction light emitting diodes based on poly(p-phenylene vinylene)/cadmium sulfide thin films, N. Deepak Kumar, Mukesh P. Joshi, Christopher S. Friend, Paras N. Prasad, Ryszard Burzynski, pp. 1388-1390, Appl. Phys. Lett. 71(10), Sep. 8, 1997.263Patterned Emission in Organic Electroluminescent Device Using Photodecomposition of Polysilane Film by UV Light, M. Hiramoto et al., Jpn. J. Appl. Phys. vol. 35, pp. 4809-4812, Sep. 1996.264Photoconductivity and charge transporting properties of metal-containing poly(p-phenylenevinylene)s, Wai Kin Chan, Xiong Gong, and Wai Yue Ng, pp. 2919-2291, Appl. Phys. Lett. 71(20), Nov. 17, 1997.265Photodegradation of poly(p-phenylenevinylene) by laser light at the peak wavelength of electroluminescence, Zyung and Kim, Electronics and Telecommunications Research Institute, Appl. Phys. Lett. 67(23), Dec. 4, 1995, pp. 3420-3422.266 *Photolithographic patterning of vacuum deposited organic light emitting devices, P. F. Tian, P. E. Burrows and S. R. Forrest, Department of Electrical Engineering, Center for Photonics and Optoelectronic Materials, Appl. Phys. Lett. 71(22), Dec. 1, 1997, pp. 3197 3199.267Photolithographic patterning of vacuum-deposited organic light emitting devices, P. F. Tian, P. E. Burrows and S. R. Forrest, Department of Electrical Engineering, Center for Photonics and Optoelectronic Materials, Appl. Phys. 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(No month).271Photophysics of Poly(p-pyridine): Blue Electroluminescent Devices from a Soluble Conjugated Polymer, Jessen, Gebler, Wang and Blatchford, The Ohio State University, Lin and Gustafson, The Ohio State University, Want, Swager and MacDiarmid, University of Pennsylvania, Eptein, The Ohio State University, pp. 573-574, Source and date not given.272Photoprocessed and micropatterned conjugated polymer LEDs, D.G. Lidzey, M.A. Pate, M.S. Weaver, T.A. Fisher, D.D.C. Bradley, pp. 141-148, Synthetic Metals 82, 1996. (No month).273Planar light-emitting devices fabricated with luminescent eletrochemical polyblends, G. Yu, Q. Pei, and A.J. Heeger, pp. 934-936, Appl. Phys. Lett. 70(8), Feb. 24, 1997.274Plastic lasers shine brightly, Donal Bradley, Nature vol. 382, Aug. 22, 1996, 1 page.275 *Polarized electroluminescence from rubbing aligned poly(2,5 dinonyloxy 1,4 phenylenevinylene) films, Hamaguchi and Yoshino, Osaka University, Appl. Phys. Lett. 67(23), Dec. 4, 1995, pp. 3381 3383.276Polarized electroluminescence from rubbing-aligned poly(2,5-dinonyloxy-1,4-phenylenevinylene) films, Hamaguchi and Yoshino, Osaka University, Appl. Phys. Lett. 67(23), Dec. 4, 1995, pp. 3381-3383.277Poly (p-phenylenevinylene) by chemical vapor deposition: synthesis, structural evaluation, glass transition, electroluminescence, and photoluminescence, Schafer, Greiner, Pommerehne, Guss, Vestweber, Tak, Bassler, Schmidt, Lusem Schartel, Stumflen, Wendorff, Spiegel, Moller and Spiess, Synthetic Metals, vol. 82 (1996), pp. 1-9. (No month).278Poly(methylphenylsilane) film as a hole transport layer in electroluminescent devices, Junji Kido and Katsutoshi Nagai, Yoshiyuki Okamoto, Terje Skotheim, pp. 2760-2762, Appl. Phys. Lett. 59(21), Nov. 18, 1991.279Poly(p-phenylene vinylene) in Light-Emitting Diodes: Nature of the Lowest Singlet and Triplet Excited States and Effects of Derivatization, Cornil, Beljonne and Bredas, Universite de Mons-Hainaut, pp. 459-460, Source and date not given.280Poly(p-phenylene vinylene)/tris (8-hydroxy) quinoline aluminum heterostructure light emitting diode. Wu, Chun, Burrows, Sturm, Thompson, Forrest and Register, Princeton University, Appl. Phys. Lett. 66 (6), Feb. 6, 1995, pp. 653-655.281Poly(p-phenylenevinylene) light-emitting diodes: Enhanced electroluminescent efficiency through charge carrier confinement, Brown, Bradley, Burroughes, Friend, Greenham, Burn, Holmes and Kraft, Appl. Phys, Lett. 61(23), Dec. 7, 1992, pp. 2793-2795.282Polyaniline as a transparent electrode for polymer light-emitting diodes: Lower operating voltage and higher efficiency, Yang and Heeger, Appl. Phys. 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(No month).287Polymer Light-Emitting Diodes with Single-and Double Layer Structures Using Poly (2,3-diphenylquinoxaline-5,8-diyl), Takakazu Yamamto, Tetsuji Inoue and Takaki Kanbara, 4 pages, Source, date and page nubmers not given.288Polymeric light-emitting diodes from molecularly thin poly(3-hexylthiophene) Langmuir-Blodgett films, A.J. Pal. T. Ostergard, J. Paloheimo, and H. Stubb, pp. 1137-1139, Appl. Phys. Lett. 69(8), Aug. 19, 1996.289Polymer-light-emitting electrochemical cells with frozen p-i-n junction, Jun Gao, Gang Yu, and Alan J. Heeger, pp. 1293-1295, Appl. Phys. Lett. 71(10), Sep. 8, 1997.290Polyquinoxaline as an excellent electron injecting material for electroluminescent device, Fukuda, Kanbara, Yamamoto, Ishikawa, Takezoe, Fukuda, Appl. Phys. Lett. 68(17), Apr. 22, 1996, pp. 2346-2348.291Polysilane-Based Polymer Diodes Emitting Ultraviolet Light, Kenzo Ebihara, Shin-ya Koshihara, Takashi Miyazawa, and Mitsuo Kira, Jpn. J. Appl. Phys. vol. 35, pp. 1278-1280, Oct. 1996.292 *PPV Info/Packet and references, Source and date not given, 8 pages.293Precursor Route Chemistry and Electronic Properties of Poly(p-phenylene-vinylene), Poly[(2,5-dimethyl-p-phenylene)vinylene] and Poly[(2,5-dimethoxy-p-phenylene)vinylene], Burn, Bradley, Friend, Halliday, Holmes, Jackson and Kraft, J. Chem. Soc. Perkin Trans. 1992, pp. 3225-3231. (No month).294Preparation and optical properties of hybrid sol-gel systems containing doubly anchored oligoarylenevinylenes, Corriu, Hesemann and Lanneua, Chem. Commun. 1996, pp. 1845-1846. (No month).295Pulsed electroluminescence from organic bilayer light emitting diodes, Y.H. Tak, J. Pommerehne, H. Vestweber, R. Sander, and H. Basler, H.H. Horhold, pp. 1291-1293, Appl. Phys. Lett. 69(9), Aug. 26, 1996.296Quantum Efficiencies of Electroluminescent Poly(Para-Phenylenes), Stampfl, Tasch, Leising and Schert, Synthetic Metals, 71 (1995), pp. 2125-2128. (No month).297 *Recombination Radiation in Anthracene Crystals, W. Helfrich and W. G. Schneider, Division of Pure Chemistry, National Research Coucil, Ottawa, Canada, vol. 14, No. 7, Feb. 15, 1965, Physical Review Letters , pp. 229 231.298Recombination Radiation in Anthracene Crystals, W. Helfrich and W. G. Schneider, Division of Pure Chemistry, National Research Coucil, Ottawa, Canada, vol. 14, No. 7, Feb. 15, 1965, Physical Review Letters, pp. 229-231.299 *Red Orange Electroluminescence with New Soluble and Air Stable Poly(naphthalene vinylene)s, Tasch, Graupner, Leising, Pu, Wagner, Grubbs, Adv. Mater. 7, No. 11, pp. 903 906, 1995. (No month).300Red-Orange Electroluminescence with New Soluble and Air-Stable Poly(naphthalene-vinylene)s, Tasch, Graupner, Leising, Pu, Wagner, Grubbs, Adv. Mater. 7, No. 11, pp. 903-906, 1995. (No month).301 *Reliability and degradation of organic light emitting devices, P. E. Burrows, V. Bulovic, S. R. Forrest, L. S. Sapochak, D. M. McCarty and M. E. Thompson, Advanced Technology Center for Photonic and Optoelectronic Materials, Princeton University, Appl. Phys. Lett. 65(23), Dec. 5, 1994, pp. 2922 2924.302Reliability and degradation of organic light emitting devices, P. E. Burrows, V. Bulovic, S. R. Forrest, L. S. Sapochak, D. M. McCarty and M. E. Thompson, Advanced Technology Center for Photonic and Optoelectronic Materials, Princeton University, Appl. Phys. Lett. 65(23), Dec. 5, 1994, pp. 2922-2924.303Room Temperature Ultraviolet Electroluminescence from Evaporated Poly(dimethylsilane) Film, Reiji Hattori, Takeshi Sugano, Junji Shirafuji, and Tsuyoshi Fujiki, Jpn. J. Appl. Phys. vol. 35, pp. 1509-1511, Nov. 1996.304Saptially Indirect Excitons as Primary Photoexcitations in Conjugated Polymers, Yan, Rothberg, Papadimitrakopoulos, Galvin and Miller, Physical Review Letters, vol. 72, No. 17, Feb. 14, 1994, pp. 1104-1107.305Single-layer white light-emitting organic electroluminescent devices based on dye-dispersed poly (N-vinylcarbazole), J. Kido, H. Shionoya, and K. Nagai, �1994 American Institute of Physics, 3 pages, Source, date and page numbers not given.306Singlet Oxygen as a Reactive Intermediate in the Photodegradation of an Electroluminescenct Polymer, Scurlock, Wang, Ogilby, Sheats and Clough, J. Am. Chem. Soc. 1995, vol. 117, No. 41, pp. 10194-10202. (No month).307Sol-Gel Synthesis of Hybrid Organic-Inorganic Materials. Hexylene-and Phenylene-Bridged Polysiloxanes, Douglas A. Loy, Gregory M. Jamison, Brigitta M. Baugher, Sharon A. Myers, Roger A. Assink, and Kenneth J. Shea, pp. 656-663, Chem. Mater. 8(3), 1996. (No month).308Solid-State Droplet Laser Made from an Organic Blend with a Conjugated Polymer Emitter, Berggren, Dodabalapur, Bao and Slusher, Adv. Mater. 1997, vol. 9, No. 12, pp. 968-971. (No month).309Soluble polypyrrole as the transparant anode in polymer light-emitting diodes, J. Gao, A.J. Hedger, J.Y. Lee, C.Y. Kim, pp. 221-223, Synthetic Metals 82, 1996. (No month).310Soluble Segmented Stepladder Poly(p-Phenylenes) for Blue-Light-Emitting Diodes, Grem, Paar, Stampfl, Leising Institut fur Festkorphysik, Huber and Scherf, Max-Planck-Institut fur Polymerforschung, Chem. Mater., 7, 1995, pp. 2-4. (No month).311Space-charge limited conduction with traps in poly(phenylene vinylene) light emitting diodes, A.J. Campbell et al., J. Appl. Phys. 82(12), Dec. 15, 1997, pp. 6326-6342.312 *Stable Poly(Para Phenylene)s and their Application in Organic Light Emitting Devices, Grem, Martin, Meghdadi, Paar, Stampfl, Sturm, Tasch and Leising, Synthetic Metals 71 (1995) pp. 2193 2194. 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C07F7/0861, H01L51/0034, C07F7/12, H01L2251/308, H01L51/5012European ClassificationC07F7/08D4H6D, C07F7/18C4C, C09K11/06, H01L51/00M6D6, H01L51/00M16, C07F7/18C4B, C07F7/12, H01L51/00M6D, C08G77/50, H01L51/00M2Legal EventsDateCodeEventDescriptionFeb 22, 2005FPExpired due to failure to pay maintenance feeEffective date: 20041226Dec 27, 2004LAPSLapse for failure to pay maintenance feesJul 14, 2004REMIMaintenance fee reminder mailedOct 15, 1998ASAssignmentOwner name: ORGANIC DISPLAY TECHNOLOGY, ILLINOISFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CHOU, HOMER Z.;REEL/FRAME:009526/0291Effective date: 19981015RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services