WO2000016593A1 - Structure for high efficiency electroluminescent device - Google Patents

Structure for high efficiency electroluminescent device Download PDF

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Publication number
WO2000016593A1
WO2000016593A1 PCT/US1999/021028 US9921028W WO0016593A1 WO 2000016593 A1 WO2000016593 A1 WO 2000016593A1 US 9921028 W US9921028 W US 9921028W WO 0016593 A1 WO0016593 A1 WO 0016593A1
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WO
WIPO (PCT)
Prior art keywords
layer
transporting layer
emission
anode
emission layer
Prior art date
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Ceased
Application number
PCT/US1999/021028
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English (en)
French (fr)
Inventor
Marc A. Baldo
Diarmuid F. O'brien
Stephen R. Forrest
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Princeton University
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Princeton University
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Publication date
Application filed by Princeton University filed Critical Princeton University
Priority to JP2000571006A priority Critical patent/JP2002525808A/ja
Priority to AU59216/99A priority patent/AU5921699A/en
Priority to EP99946910A priority patent/EP1116417A4/en
Publication of WO2000016593A1 publication Critical patent/WO2000016593A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • 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
    • H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to stacked electroluminescent devices, and more particularly to stacked electroluminescent devices that make use of exciton blocking layers for enhanced efficiency.
  • OLEDs Organic light emitting devices
  • DH double heterostructure
  • SH single heterostructure
  • EL emission layer
  • the EL 13 provides the recombination site for electrons injected from a 100-500A thick electron transporting layer 14 (ETL) with holes from the HTL 12.
  • ETL electron transporting layer 14
  • Examples of prior art ETL, EL and HTL materials are disclosed in U.S. Patent No. 5,294,870, the disclosure of which is incorporated herein by reference.
  • the device shown in Fig. 1A is completed by the deposition of rtal contacts 15, 16 and a top electrode 17. Contacts 15 and 16 are typically fabricated from indium or Ti/Pt/Au.
  • the electrode 17 is often a dual layer structure consisting of an alloy such as Mg/Ag 17' directly contacting the organic ETL 14, and an opaque, high work function metal layer 17' ' such as gold (Au) or silver (Ag) on the Mg/Ag.
  • an alloy such as Mg/Ag 17' directly contacting the organic ETL 14, and an opaque, high work function metal layer 17' ' such as gold (Au) or silver (Ag) on the Mg/Ag.
  • the SH OLED makes use of multifunctional layer 13' to serve as both EL and ETL.
  • multifunctional layer 13 ' must have good electron transport capability. Otherwise, separate EL and ETL layers should be included as shown for the device of Fig. 1A.
  • a single layer polymer OLED is shown in Fig. 1C.
  • this device includes a glass substrate 1 coated by an anode layer 3.
  • a thin organic layer 5 of spin-coated polymer, for example, is formed over the anode layer 3, and provides all of the functions of the HTL, ETL, and EL layers of the previously described devices.
  • a metal electrode layer 6 is formed over organic layer 5.
  • the metal is typically Mg or other conventionally-used low work function metal.
  • Light emission from OLEDs is typically via fluorescence or phosphorescence.
  • Successful utilization of phosphorescence holds enormous promise for organic electroluminescent devices.
  • an advantage of phosphorescence is that all excitons (formed by the recombination of holes and electrons in an EL) , which are triplet-based in phosphorescent devices, may participate in energy transfer and luminescence in certain electroluminescent materials.
  • only a small percentage of excitons in fluorescent devices, which are singlet-based result in fluorescent luminescence.
  • phosphorescent devices have several potential drawbacks that must be overcome to produce useful electroluminescence. For example, energy transfer is relatively slow, as long range dipole-dipole coupling
  • the present invention includes light emitting devices that include a pixel comprising a substantially transparent anode; a hole transporting layer over the anode; an emission layer over the hole transporting layer; a blocking layer over the emission layer; an electron transporting layer over the blocking layer; and a cathode in electrical contact with the electron transporting layer.
  • the blocking layer used in the devices of the present invention substantially blocks the diffusion of excitons, thus substantially keeping the excitons within the emission layer to enhance device efficiency.
  • An advantage of the present invention is that it provides enhanced electroluminescent organic light emitting devices.
  • Another advantage of the present invention is that it provides feasible and efficient phosphorescent electroluminescent devices.
  • Alq 3 refers to aluminum tris (8- hydroxyquinoline) .
  • Anode refers to a positively charged receiver of electrons that flow from a negatively charged cathode.
  • Bin gap refers to the energy level difference between the lowest unoccupied molecular orbital of a material and its highest occupied molecular orbital.
  • BCP refers to bathocuproine .
  • Blocking layer refers to a layer comprising a material that substantially blocks the diffusion of excitons .
  • Cathode refers to a negatively charged device that emits electrons, which flow to a positively charged anode .
  • CBP carbazole biphenyl
  • EL refers to "emission layer, " which is a layer in which holes and electrons recombine to produce excitons, which emit light.
  • ETL refers to "electron transporting layer, " which is a layer used to supply electrons to an emission layer in a stacked OLED device.
  • HTL refers to "hole transporting layer, " which is a layer used to supply holes to an emission layer in a stacked OLED device.
  • NPD refers to N, N' -diphenyl-N, N ' -bis-alpha- napthylbenzidine .
  • Pigl refers to the smallest addressable unit on a display screen.
  • PtOEP refers to 2 , 3 , 7 , 8 , 12 , 13 , 17, 18-octaethyl- 21H, 23H-porphine platinum (II) .
  • Fig. 1A is a cross sectional view of a typical organic double heterostructure light emitting device (OLED) according to the prior art .
  • Fig. IB is a cross sectional view of a typical organic single heterostructure light emitting device (J.ED) according to the prior ar .
  • Fig. 1C is a cross sectional view of a known single layer polymer LED structure according to the prior art.
  • Fig. 2 is a cross sectional view of an embodiment of the present invention.
  • Fig. 3 is a cross sectional view of an exemplary embodiment of the present invention.
  • Fig. 4(a) is an emission spectra for a stacked light emitting device not including a blocking layer.
  • Fig. 4(b) is an emission spectra for a stacked light emitting device including a blocking layer, in accordance with an embodiment of the present invention.
  • Fig. 5 compares the efficiency of a stacked light emitting device including a blocking layer according to an embodiment of the present invention to a stacked light emitting device not including a blocking layer.
  • the present invention includes light emitting devices comprising a substantially transparent anode; a hole transporting layer over the anode; an emission layer over the hole transporting layer; a blocking layer over the emission layer; an electron transporting layer over the blocking layer; and a cathode in electrical contact with the electron transporting layer.
  • the blocking layer used in the devices of the present invention substantially blocks the diffusion of excitons, thus substantially keeping the excitons within the emission layer to enhance device efficiency.
  • the devices of the present invention are most advantageously used with emissive materials that undergo phosphorescent electroluminescence. In such devices, holes from a hole transporting layer recombine in an emission layer with electrons from an electron transporting layer to form triplet -based excitons.
  • the present invention makes use of a blocking layer that allows for the diffusion of electrons but substantially prevent the diffusion of excitons therethrough.
  • the blocking layer may also substantially prevent the diffusion of holes therethrough.
  • Excitons produced in an emission layer are thus confined to the emission layer, thus substantially enhancing device performance and efficiency.
  • the blocking layer of the present invention is characterized by a band gap between its lowest unoccupied molecular orbital and its highest occupied molecular orbital.
  • this band gap substantially prevents the diffusion of excitons through the blocking layer, yet has only a minimal effect on the turn-on voltage of a completed electroluminescent device.
  • the band gap is thus preferably greater than the energy level of excitons produced in an emission layer, such that such excitons are not able to exist in the blocking layer.
  • the device 100 includes a substantially transparent substrate 110, a substantially transparent anode 111, a hole transporting layer 112, an emission layer 113, a blocking layer 114, an electron transporting layer 115, and a cathode 117.
  • the emission layer 113 optionally also functions as an electron transporting layer.
  • a low work function (preferably, ⁇ 4 eV) metal layer 116 is optionally formed over the electron transporting layer 115.
  • the metal layer 116 serves both as a contact material and as a reflective material for reflection of impinging light beams . Light emission from the emission layer 113 occurs when a voltage is applied between the cathode 117 and ;he anode 111.
  • the blocking layer 114 substantially prevents the diffusion of excitons from the emission layer 113 into the electron transporting layer 115.
  • the excitons are also substantially prevented from diffusing into the hole transporting layer 111 due to an energy barrier at the interface between the emission layer 113 and the hole transporting layer 111.
  • the excitons are thus substantially confined within the emission layer 113.
  • the materials used in the device 100 include any suitable materials which fulfill the purpose (s) of the respective layer (s) .
  • the following materials are provided for illustrative purposes only.
  • the substrate 110 is generally fabricated from a transparent material, such as glass, quartz, sapphire or plastic.
  • the substrate 110 is, for example, rigid, flexible, and/or shaped to a desired configuration.
  • the anode 111 comprises any substantially transparent, conductive material such as indium tin oxide. Suitable candidates for the metal layer 116 include Mg, Mg/Ag, and Li/Al.
  • the cathode 117 is made of ITO, Al, Ag or Au, for example.
  • the blocking layer 114 is made from any suitable material having a sufficient band gap to substantially prevent the diffusion of excitons therethrough.
  • suitable candidates for the blocking layer 114 include NPD, CBP, BCP and Alq 3 .
  • the choice of blocking layer material will depend on the choice of material used in the emission layer, as the blocking layer material need only have a larger band gap than the energy level of the excitons formed in the emission layer, which depends upon the material used in the emission layer.
  • the blocking layer 114 is made from BCP when the emission layer 513 comprises CBP.
  • the emission layer 113 comprises any suitable blue light- emissive organic compound such as, for example, trivalent metal quinolate complexes, Schiff base divalent metal complexes, metal acetylacetonate complexes, metal bidentate ligand complexes, bisphosphonates , metal maleontriledithiolate complexes, molecular charge transfer complexes, aromatic and heterocyclic polymers and rare earth mixed chelates.
  • the metal bidentate complexes which may be used for the layer 113 have the formula MDL 2 wherein M is selected from trivalent metals of Groups 3-13 of the Periodic Table and Lanthanides .
  • the preferred metal ions are Al +3 , Ga +3 , In +3 and Sc +3 .
  • D is a bidentate ligand such as 2-picolylketones, 2-quinaldylkentones and 2- (o- phenoxy) pyridine ketones .
  • the preferred groups for L 4 include acetylacetonate, compounds of the formula OR 3 R wherein R 3 is selected from Si and C, and R is selected from hydrogen, substituted and unsubstituted alkyl, aryl and heterocyclic groups; 3,5-di(t-bu) phenol; 2,6-di(t-bu) phenol; 2,6-di(t-bu) cresol; and H 2 Bpz 2 .
  • the wavelength resulting from measurement of photoluminescence in the solid state of aluminum (picolymethylketone) bis [2 , 6-di (t-bu) phenoxide] is 420nm.
  • the cresol derivative of this compound also measured 420nm.
  • Aluminum (picolylmethyl-ketone) bis (OsiPh 3 ) and scandium (4-methoxy-picolyl-methylketone) bis (acetylacetonate) each measured 433nm, while aluminum [2- (O-phenoxy) pyridine] bis [2 , 6-di (t-bu) phenoxide] measured 450nm.
  • green OLED materials include tin (iv) metal complexes, such as those having the formula SnL 1 2 L 2 2 where L 1 is selected from salicylaldehydes, salicyclic acid or quinolates (e.g. 8-hydroxyquinoline) .
  • L 2 can be substituted and unsubstituted alkyl, aryl and heterocyclic groups.
  • L 1 is a quinolate and L 2 is a phenyl
  • the tin (iv) metal complex will have an emission wavelength of 504nm.
  • red OLED materials include divalent metal maleonitriledithiolate (“mnt”) complexes, such as those described by C.E. Johnson et al . in "Luminescent Iridium(I), Rhodium(I), and Platinum (II) Dithiolate Complexes," 105 Journal of the American Chemical Society 1795 (1983) .
  • mnt divalent metal maleonitriledithiolate
  • the mnt [Pt (Pph 3 ) j has a characteristic wavelength emission of 652nm. Additional OLED materials are known in the art
  • Phosphorescent and fluorescent dyes which may be used in the emission layer of the devices of the present invention are also known in the art.
  • Phosphor dyes are, for example, vacuum deposited in a solid polymer matrix or dissolved in matrix polymer such as polymethylmethacrylate .
  • green fluorescent dyes are polymethine dyes including cyanines, merocyanines, complex cyanines and merocyanines, oxonols, hemioxonols, styryls, merostyryls and streptocyanines .
  • red fluorescent dyes are 4-dicyano-methylene-4H-pyrans and 4- dicyanomethylene-4H-thiopyrans .
  • the emission layer undergoes phosphorescent electroluminescence and comprises a phosphor in an organic host.
  • the emission layer comprises CBP doped with PtOEP.
  • the deposition techniques for any of the above- listed layers and materials are well-known in the art.
  • the preferred method of depositing the OLED layers i.e., HTL, EL and ETL layers
  • the preferred method of depositing the OLED layers is by thermal evaporation (or spin coating if a polymer LED is used)
  • the preferred method of depositing metal layers is by thermal or electron-beam evaporation
  • the preferred method of depositing indium tin oxide is by electron-beam evaporation or sputtering.
  • the present invention is used to provide efficient, high brightness, monochromatic or multicolor, flat panel displays of any size.
  • the images created on such displays could be text or illustrations in full-color, in any resolution depending on the size of the individual LED ' s .
  • Display devices of the present invention are therefore appropriate for an extremely wide variety of applications including billboards and signs, computer monitors, and telecommunications devices such as telephones, televisions, large area wall screens, theater screens and stadium screens.
  • the structures described herein are included, for example, in a plurality of pixels in a light emitting device or as part of a single-pixel device. Moreover, the structures described herein may be used as part of a laser device.
  • the present invention is further described with reference to the following non-limiting example:
  • a phosphorescent electroluminescent device 500 as shown in Fig. 3 was formed using conventional deposition techniques.
  • the device 500 included the following layers deposited onto a glass substrate 510: an anode 511 comprising indium tin oxide, a HTL 512 of approximately 450A thickness comprising NPD, an EL 513 of approximately 400A thickness comprising CBP doped with about 8% PtOEP, a blocking layer 514 of approximately 80A thickness comprising BCP, an ETL 515 of approximately 250A thickness comprising Alq 3 , a contact layer 516 of approximately lHOOA thickness comprising magnesium-silver alloy, and a cathode
  • the blocking layer 514 was included in the device 500 to prevent exciton diffusion from the EL 513 into the ETL 515.
  • the exciton blocking function of the layer 514 is demonstrated by a comparison of the spectra in Figs. 4(a) and 4 (b) .
  • the present invention provides high efficiency electroluminescent devices, particularly for phosphorescent emission.
  • Those with skill in the art may recognize various modifications to the embodiments of the invention described and illustrated herein. Such modifications are meant to be covered by the spirit and scope of the appended claims .

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/US1999/021028 1998-09-14 1999-09-14 Structure for high efficiency electroluminescent device Ceased WO2000016593A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2000571006A JP2002525808A (ja) 1998-09-14 1999-09-14 高効率の電界発光デバイスのための構造
AU59216/99A AU5921699A (en) 1998-09-14 1999-09-14 Structure for high efficiency electroluminescent device
EP99946910A EP1116417A4 (en) 1998-09-14 1999-09-14 STRUCTURE FOR HIGHLY EFFICIENT ELECTROLUMINESCENT DEVICE

Applications Claiming Priority (2)

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US09/153,144 1998-09-14
US09/153,144 US6097147A (en) 1998-09-14 1998-09-14 Structure for high efficiency electroluminescent device

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US (1) US6097147A (enExample)
EP (1) EP1116417A4 (enExample)
JP (5) JP2002525808A (enExample)
KR (1) KR100698964B1 (enExample)
AU (1) AU5921699A (enExample)
WO (1) WO2000016593A1 (enExample)

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JP2013239724A (ja) 2013-11-28
EP1116417A4 (en) 2008-12-10
KR20010079818A (ko) 2001-08-22
EP1116417A1 (en) 2001-07-18
JP2012009877A (ja) 2012-01-12
JP2015005777A (ja) 2015-01-08
JP2002525808A (ja) 2002-08-13
US6097147A (en) 2000-08-01
AU5921699A (en) 2000-04-03
JP2017028309A (ja) 2017-02-02
KR100698964B1 (ko) 2007-03-23

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