WO2000003565A1 - Matieres moleculaires amorphes pour dispositifs opto-electroniques et procede de production de celles-ci - Google Patents
Matieres moleculaires amorphes pour dispositifs opto-electroniques et procede de production de celles-ci Download PDFInfo
- Publication number
- WO2000003565A1 WO2000003565A1 PCT/US1999/015437 US9915437W WO0003565A1 WO 2000003565 A1 WO2000003565 A1 WO 2000003565A1 US 9915437 W US9915437 W US 9915437W WO 0003565 A1 WO0003565 A1 WO 0003565A1
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- WIPO (PCT)
- Prior art keywords
- organic
- light emitting
- emitting device
- organic light
- electrode
- Prior art date
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- 239000000463 material Substances 0.000 title description 39
- 238000000034 method Methods 0.000 title description 7
- 230000008569 process Effects 0.000 title description 4
- 230000005693 optoelectronics Effects 0.000 title description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 38
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 38
- 239000012044 organic layer Substances 0.000 claims abstract description 37
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims description 36
- 230000005525 hole transport Effects 0.000 claims description 21
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 20
- 239000010410 layer Substances 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 17
- -1 anthracyl Chemical group 0.000 claims description 16
- YDUVZTACEKAXTE-UHFFFAOYSA-N 1,3,5,7-tetraphenyladamantane Chemical compound C1C(C2)(C=3C=CC=CC=3)CC(C3)(C=4C=CC=CC=4)CC1(C=1C=CC=CC=1)CC23C1=CC=CC=C1 YDUVZTACEKAXTE-UHFFFAOYSA-N 0.000 claims description 13
- PEQHIRFAKIASBK-UHFFFAOYSA-N tetraphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PEQHIRFAKIASBK-UHFFFAOYSA-N 0.000 claims description 13
- JLAVCPKULITDHO-UHFFFAOYSA-N tetraphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JLAVCPKULITDHO-UHFFFAOYSA-N 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 3
- 239000010408 film Substances 0.000 description 22
- 238000013461 design Methods 0.000 description 18
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 230000008901 benefit Effects 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 3
- ILEXMONMGUVLRM-UHFFFAOYSA-N tetraphenylgermane Chemical compound C1=CC=CC=C1[Ge](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ILEXMONMGUVLRM-UHFFFAOYSA-N 0.000 description 3
- WBJSMHDYLOJVKC-UHFFFAOYSA-N tetraphenyllead Chemical compound C1=CC=CC=C1[Pb](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WBJSMHDYLOJVKC-UHFFFAOYSA-N 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- 101100207325 Arabidopsis thaliana TPPE gene Proteins 0.000 description 2
- 101000679365 Homo sapiens Putative tyrosine-protein phosphatase TPTE Proteins 0.000 description 2
- 102100022578 Putative tyrosine-protein phosphatase TPTE Human genes 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 229910000078 germane Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000000877 morphologic effect Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 2
- UFRJXUZOEXNCKE-UHFFFAOYSA-N 1,3,5,7-tetraphenyladamantane tetraphenylsilane tritylbenzene Chemical compound C1(=CC=CC=C1)C12CC3(CC(CC(C1)(C3)C3=CC=CC=C3)(C2)C2=CC=CC=C2)C2=CC=CC=C2.C2(=CC=CC=C2)[Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.C2(=CC=CC=C2)C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 UFRJXUZOEXNCKE-UHFFFAOYSA-N 0.000 description 1
- SSXRRKVCVZJNDB-UHFFFAOYSA-N 1-ethenyl-2-(2-phenylethenyl)benzene Chemical class C=CC1=CC=CC=C1C=CC1=CC=CC=C1 SSXRRKVCVZJNDB-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical group CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 241001598984 Bromius obscurus Species 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- XRCKXJLUPOKIPF-UHFFFAOYSA-N plumbane Chemical compound [PbH4] XRCKXJLUPOKIPF-UHFFFAOYSA-N 0.000 description 1
- 229910000081 plumbane Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 230000007847 structural defect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 description 1
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/114—Poly-phenylenevinylene; Derivatives thereof
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- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- the present invention relates generally to compounds for use in organic light emitting devices (OLEDs). More particularly, the present invention relates to novel highly symmetrical tetrahedral shaped aromatic and/or aromatic amine containing molecules, and their syntheses, for application in high temperature OLED displays.
- OLED organic light emitting devices
- Amorphous molecular films are easily fabricated using the thermal deposition method. Variables such as deposition rate and temperature of substrate can be tuned to control film morphology. As a rule, higher deposition rates and cooler substrate temperatures each favor the preparation of amorphous molecular films. Once formed however, most molecular films tend to crystallize at room temperature because the amorphous morphology is generally a non- equilibrium phase, higher in energy than the ordered crystalline (polycrystalline) phase. The rate of film crystallization depends on the ambient temperature and its relation to the glass transition temperature (T g ) of the material. A second important factor controlling film crystallization is maximum crystallization velocity (MCV), which is also characteristic of a particular material.
- MCV maximum crystallization velocity
- Stable amorphous films will have a high T g and a low MCV. If the T g value of an amorphous material is greater than its thermal environment, that material will tend to remain amorphous. Similarly, if the MCV is very low. even at high temperatures some materials will remain amorphous indefinitely. It is possible to relate these thermodynamic and kinetic factors to understand how molecular design can be optimized to yield thermally stable amorphous molecular films. From this analysis. Naito has concluded that thermally stable organic dye glasses can be formed form large, symmetric, globular, rigid, and dense molecules, ((a) Naito, K.; Miura, A. J Phys. Chem. 1993 97, 6240-6248.
- T g of NPB is 95 °C compared to 175 °C for the electron transport material, Alq 3 .
- An informative report by Tokito, et al. highlights the limiting thermal stability of the hole-conducting layer, ((a)
- the experiment was carried out by driving each device at a constant current of 11 mA/cm 2 and gradually increasing the ambient temperature from room temperature upwards. For each device, a dramatic drop in electroluminescence output was observed just above the T g of each hole conducting layer. Shown below are the five hole conducting compounds with their T g values and the temperature at which electroluminescence output rapidly degraded.
- tertiary aromatic amines have been found to function very well as hole conducting materials due to a low ionization potential and good hole mobility.
- the most simple aromatic amines such as triphenylamine, do not form stable amorphous films.
- Assembling larger molecules such as in the case of the benzidine compounds (e.g. NPB) can be used to improve the film forming properties.
- the synthetic strategy that has been followed to further increase glass transition temperatures of these materials links aromatic arnines together to form either "starburst" structures (shown below). (See for example: (a) Shirota, Y.; Kobata,
- TPPE TPPE
- the open linear structure allows adjacent molecules to interact over a large portion of their molecular surface and would be expected to have the greatest difficulty in thermal sublimation.
- Thermal sublimation requires that the weak intermolecular forces holding the molecules in the solid state must be broken to force the molecules in the gas phase.
- perfectly symmetrical spherical structures should only interact with adjacent molecules at their periphery. In principle, much larger molecular weight materials should be accessible without drastically compromising the compound's volatility.
- the known "starburst" structures have not utilized central cores that enforce truly spherical geometry.
- the 1,3,5-substituted benzene ring is trigonal planar and triphenyoamine is trigonal pyramidal.
- T g glass transition temperature
- the organic compounds contain tetrahedral shaped core structures allowing the organic light emitting device to operate at
- the present invention comprises an organic light emitting device comprising a first electrode, a second electrode, and an organic stack interposed between the first electrode and the second electrode, wherein the organic stack further comprises at least one organic layer, wherein the organic layer further comprises organic compounds such that the organic light emitting device continues to function in temperatures in excess of 145° C.
- the organic layer may be comprised of organic compounds with tetrahedral shaped core structures, tetrahedral shaped core structures containing aromatic side groups, tetrahedral shaped core structures containing aromatic amine side groups, symmetrical tetrahedral shaped core structures, symmetrical tetrahedral shaped core structures containing aromatic side groups, and/or symmetrical tetrahedral shaped core structures containing aromatic amine side groups.
- the aromatic side groups may be, but are not limited to, phenyl, naphthyl, anthracyl, carbazole, and any and all substituted analogs thereof.
- the tetrahedral or symmetrical tetrahedral shaped core structure may be a tetraphenyl compound, including, but not limited to, tetraphenylmethane, tetraphenylsilane, tetraphenyladamantane, tetraphenylgermane, tetraphenylplumbane. and/or tetramethylstannane.
- the tetraphenyl compound may be functionalized at the ⁇ ro-position.
- the tetrahedral shaped core structures may satisfy one or more of the formula (C 6 H 5 ) 4 R, where R may be, but is not limited to, C, Si, adamantane (C 10 H t2 ), Ge, Pb, or Sn.
- R may be, but is not limited to, C, Si, adamantane (C 10 H t2 ), Ge, Pb, or Sn.
- the organic compounds with tetrahedral shaped core structures may satisfy one or more of the formula (C 6 H 5 ) 4 R, where R may be, but is not limited to, C, Si, adamantane (C 10 H t2 ), Ge, Pb, or Sn.
- the organic compounds with tetrahedral shaped core structures may satisfy one or more of the formula (C 6 H 5 ) 4 R, where R may be, but is not limited to, C, Si, adamantane (C 10 H t2 ), Ge, Pb, or
- R (C 6 H 5 ) 4 R, where R, may be, but is not limited to, aromatic groups and/or aromatic amine groups, and where R may be, but is not limited to, C, Si, adamantane (C 10 H 12 ), Ge, Pb, or Sn.
- the tetrahedral shaped core structures may be, but are not limited to:
- the organic layer may contain, but is not limited to, organic compounds selected from the group consisting of:
- R may be, but is not limited to, the group consisting of:
- the organic compounds with a tetraphenyl core may be, but are not limited to, the group consisting of:
- the tetraphenyl core may be, but is not limeted to. tetraphenylmethane. tetraphenylsilane, tetraphenyladamantane, tetraphenylgermane, tetraphenylplumbane, and/or tetramethylstannane.
- the present invention comprises an organic light emitting device having a first electrode, a second electrode, and an organic stack interposed between the first electrode and the second electrode, where the organic stack may further comprise at least one hole transport layer.
- the hole transport layer may further comprise organic compounds with tetrahedral shaped core
- the organic compounds of the at least one hole transport layer may be comprised of tetrahedral shaped core structures, tetrahedral shaped core structures containing aromatic side groups, tetrahedral shaped core structures containing aromatic amine side groups, symmetrical tetrahedral shaped core structures, symmetrical tetrahedral shaped core structures containing aromatic side groups, and/or symmetrical tetrahedral shaped core structures containing aromatic amine side groups.
- the aromatic side groups may be, but are not limited to, phenyl, naphthyl, anthracyl, carbazole. and any and all substituted analogs thereof.
- the tetrahedral or symmetrical tetrahedral shaped core structure may be a tetraphenyl compound, including, but not limited to, tetraphenylmethane, tetraphenylsilane, tetraphenyladamantane, tetraphenylgermane, tetraphenylplumbane, and/or tetramethylstannane.
- the tetraphenyl compound may be functionalized at the ⁇ ra-position.
- the organic layer of the present invention may further comprise organic compounds containing tetrahedral shaped core structures including, but not limited to, silicon based tetrahedral core structures, carbon based tetrahedral core structures, adamantane based tetrahedral core structures, germane based tetrahedral core structures, plumbane based tetrahedral core structures, and stannane based tetrahedral core structures.
- the tetrahedral shaped core structures may contain aromatic side groups and/or aromatic amine side groups oriented away from one another at angles between 100° and 120°.
- the present invention describes novel highly symmetrical tetrahedral shaped aromatic amine containing molecules and their syntheses for application as hole conduction materials in high temperature OLED displays.
- Applicant has identified tetraphenylmethane, tetraphenylsilane and tetraphenyladamantane as very attractive candidates to serve as rigid tetrahedral core structures.
- Tetraphenylmethane Tetraphenylsilane Tetraphenyladamantane
- the tetrahedral core structures shown above are easily obtained in large quantities using developed synthetic methodology, ((a) Wilson, L.M.; Griffin, A.C. J. Mater. Chem. 1993, 3, 991-994. (b) Su, D.; Menger, F.M. Tetrahedron Lett. 1997, 38, 1485-1487. (c) Liu, F.-Q.;
- the rigid tetrahedral framework orients the appended groups away from one another at an angle of between 100° and 120°, or approximately 109.5°, and reduces the possibility of forming intramolecular ⁇ -stacked compounds. If rigid dye molecules are coupled in the tetrahedral array, the proposed molecular design should discourage undesirable intramolecular aggregate or exciplex formation. Also because the organic dye molecules radiate from a central tetrahedral core, they are hindered from forming intermolecular ⁇ -aggregates in solid state films, thereby preventing luminescence
- Applicant has also pursued the synthesis of tetrahedral amine-containing materials that are linked to the core via phenyl- henyl or phenyl-vinyl connections to further explore the effect of structural diversity on solid state morphology and thermal stability.
- the present invention allows a novel entry of a large number of different aromatic amines for use in OLEDs.
- the variety of aromatic groups such as phenyl and substituted analogs thereof, naphthyl, anthracyl, carbazolyl, etc. provides access to range of possible structures.
- the approach of the present invention can be used to quickly screen many potential and novel hole transport materials, that will be selected for application based on hole transport properties and T g .
- the novel materials should maintain the desirable hole transport properties common to aromatic amines, but will significantly extend the required high temperature morphological stability.
- T g values anticipated for the proposed and novel aromatic amine containing materials may be roughly estimated from related tetrahedral stilbenoid compounds prepared by Oldham, et al. (Oldham, W.J., Jr.; Lachicotte, R.J.; Bazan, G.C. J. Am. Chem. Soc. 1998, 120, (in press).
- high T g blue luminescent materials were prepared by coupling vinylstilbene derivatives to a tetraphenylmethane core using the palladium catalyzed Heck reaction (eq. 2).
- the tetrahedral core strategy provides materials with high T g and very low crystallization velocities. Materials of this class can be fabricated as amorphous thin-films that are completely stable against crystallization, even when heated above their glass transition temperature.
- a significant advantage of the tetrahedral core molecular design over polymeric OLED materials is that it combines the traditional advantages of small molecules (e.g. high chemical purity and volatility) with those of polymers (e.g., high T g , low MCV, thermal stability).
- the hole transport materials proposed in this work are new compounds.
- An object of the present invention is to successfully prepare and purify the compounds for electronic applications. Although the proposed synthetic methods are developed and have been used successfully in related systems, the compounds of the present invention have not previously been synthesized.
- Another object of the present invention is to design and synthesize novel high molecular weight materials (expected to have the highest thermal stability), while retaining the volatility necessary to allow films to be fabricated by thermal sublimation. Applicant believes that the new materials containing four amine groups should possess the necessary volatility.
- the chemical stability of radical cations (also called holes) incorporating the core structures is unknown. Triphenylmethyl cation or triphenylmethyl radical are relatively stable species and the danger of disproportionation reactions upon injection of holes is a primary consideration. To mitigate against this possibility
- the ionization potential of the new materials could be altered relative to NPB. If the ionization potential is reduced too much, then undesirable exciplex formation can occur at the interface of the hole transport layer and Alq 3 .
- Another object of the present invention is to control the ionization potential to ameliorate this risk by judicious choice of aromatic groups bonded to nitrogen.
- tetrahedral shaped core molecules may include carbon, silicon, adamantane. germane, plumlane. or stannane structures or elements.
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Abstract
La présente invention concerne un dispositif électroluminescent organique comportant une première électrode, une deuxième électrode, et un empilage organique placé entre la première électrode et la deuxième électrode. L'empilage organique comporte au moins une couche organique. La couche organique comporte des composés organiques permettant au dispositif électroluminescent organique de continuer à fonctionner à des températures dépassant 145 °C. La couche organique peut être constituée de composés organiques possédant des structures à noyau tétraédrique, des structures à noyau tétraédrique contenant des groupes latéraux aromatiques, des structures à noyau tétraédrique contenant des groupes latéraux amines aromatiques, des structures à noyau tétraédrique symétriques, des structures à noyau tétraédrique symétriques contenant des groupes latéraux aromatiques, et/ou des structures à noyau tétraédrique symétriques contenant des groupes latéraux amines aromatiques.
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