WO1998040899A1 - Dispositif electroluminescent sur la base d'un polymere a deux couches representant une electroluminescence d'interface - Google Patents

Dispositif electroluminescent sur la base d'un polymere a deux couches representant une electroluminescence d'interface Download PDF

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Publication number
WO1998040899A1
WO1998040899A1 PCT/US1998/004988 US9804988W WO9840899A1 WO 1998040899 A1 WO1998040899 A1 WO 1998040899A1 US 9804988 W US9804988 W US 9804988W WO 9840899 A1 WO9840899 A1 WO 9840899A1
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WO
WIPO (PCT)
Prior art keywords
polymeric layer
interface
layer
electroluminescent device
poly
Prior art date
Application number
PCT/US1998/004988
Other languages
English (en)
Other versions
WO1998040899A9 (fr
Inventor
Arthur J. Epstein
Darren D. Gebler
Yunzhang Wang
Original Assignee
The Ohio State University Research Foundation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Ohio State University Research Foundation filed Critical The Ohio State University Research Foundation
Priority to AU65548/98A priority Critical patent/AU6554898A/en
Priority to JP10539861A priority patent/JP2000513153A/ja
Priority to EP98911635A priority patent/EP1008164A1/fr
Priority to CA002307035A priority patent/CA2307035A1/fr
Publication of WO1998040899A1 publication Critical patent/WO1998040899A1/fr
Publication of WO1998040899A9 publication Critical patent/WO1998040899A9/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H05B33/14—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
    • 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

Definitions

  • electroluminescent devices which are commonly referred to as electroluminescent devices.
  • the configurations of these devices may consist of a
  • emission wavelength or multilayers that may allow the device to operated under an
  • PVK Poly(N-vinylcarbazole)
  • PVK is a well
  • Another object of the present invention is to provide polymeric light-emitting-
  • light-emitting devices that may optionally be used to produce laser light.
  • the present invention includes an electroluminescent device
  • polymeric layer are in electrical contact so as to form an interface, the interface being
  • An exciplex is a transient donor-acceptor complex between the excited state of
  • the first polymeric layer has a greater hole transport capability than the
  • This layer may comprise any appropriate polymer, copolymer or oligomer, or derivative thereof.
  • polymeric hole transport/electron blocking layer may be any polymeric hole transport/electron blocking layer.
  • carbazole-coating polymer such as poly(vinyl carbazole) (PVK).
  • Figure 2 shows the chemical structure of the repeating units of polymers that
  • PVK poly(vinyl carbazole)
  • the polymeric layer acting as the electron transporting emissive layer may be any polymeric layer acting as the electron transporting emissive layer.
  • This layer may
  • Figure 7(a), 7(b) and 7(c) show other examples of copolymers and their
  • copolymer PPyVP(COOC 12 FI 25 ) 2 V render the copolymer more resistive to oxidation
  • copolymers are soluble in common organic solvents such as ⁇
  • TFIF tetrahydrofuran
  • xylene tetrahydrofuran
  • chloroform tetrahydrofuran
  • injecting electrode 1 may be of any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material. Electrodes may be any appropriate material.
  • semiconductors and conducting polymers including, but not limited to, a wide variety
  • ITO indium-tin-oxide
  • metals such as gold
  • polymers such as highly-conducting doped polyaniline, highly-conducting doped
  • polypyrrole polyaniline salt (such as PAN-CSA) or other doped pyridyl nitrogen-
  • polymer such as polypyridylvinylene.
  • Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be of any appropriate material. Electrodes may be any appropriate material.
  • semiconductors and conducting polymers including, but not limited to, a wide variety
  • conducting materials such as (1) metals such as aluminum, calcium, silver, copper,
  • conducting fibers such as carbon fibers
  • polymers such as highly-conducting doped polyaniline, highly-conducting doped
  • polypyrrole polyaniline salt (such as PAN-CSA) or other doped pyridyl nitrogen-
  • polymer such as polypyridylvinylene.
  • At least one of the electrodes may be fashioned from a transparent material such as ITO
  • the electrode material be transparent or
  • light emission from the edge of the device may be utilized in, for
  • edge-lighted displays or in coupling applications such as in coupling the
  • the device on a substrate which also serves to protect and often to insulate (both
  • the substrate layer may be any material that is physically and electrically) the device during use.
  • the substrate layer may be any material that is physically and electrically) the device during use.
  • the substrate layer may be any material that is physically and electrically) the device during use.
  • the substrate layer may be any material that is physically and electrically) the device during use.
  • the substrate layer may be any material that is physically and electrically) the device during use.
  • the substrate layer may be any material
  • the substrate layer is
  • substrate layer 2 shown in Figure 1 as substrate layer 2.
  • the devices of the present invention may be operated by any appropriate
  • the first electrode and the second electrode are electrically connected to-a
  • the first electrode can be connected to a positive
  • the electrodes 1 and 2 are connected to a voltage source 8 by means of
  • the electrical connector or contact can be the electrodes 1 and 3 themselves. That is,
  • the potential difference from voltage source 8 may be applied directly to the
  • electrodes in which case electrodes 1 and 3 may become the electrical contact or
  • the devices of the present invention may feature a relatively low turn-on and
  • a turn-on and operating voltage of less than about 12, and
  • Devices of the present invention may be operated with AC current in
  • ITO electrodes which may tend to quench luminescence.
  • Another advantage is that the charge is confined at the polymer/polymer —
  • the electron blocking layer i.e., such as
  • the devices of the present invention also feature a sequestered
  • the devices of the present invention may also be used to produce electrically
  • Optically pumped lasing may be attained
  • pumped lasing may be attained by supplying enough current density to create a
  • Figure 1 is a general schematic of a light-emitting device of the present
  • Figure 2 shows the chemical structure of the repeating units of polymers that
  • PVK poly(vinyl carbazole)
  • Figure 3 is a graph showing the photoluminesence spectra of
  • Figure 4 is a graph showing the photoluminesence spectra of a bilayer of PVK
  • FIG. 5 shows graphs of the absorption and photoluminesence excitation
  • FIG. 6 shows graphs of the electroluminesence and photoluminesence
  • Figure 7 shows the chemical structures (a) - (e) of the repeating units of
  • structure (a) shows three alternative derivatives according to variations in
  • R OC, 6 H 33 , C 12 H 25 or COOC 12 H 25 , designated structures "ax,”
  • structure (e) is designated wPDTP.
  • Figures 8a through 8e are graphs showing the photoluminesence and PLE
  • Figure 9 is a graph showing the photoluminesence spectra of several
  • Figures 10 and 1 1 show the PL spectra of single layers of PVK and each of the
  • Figure 10 shows (a) the film PL
  • PVK/PPyVPV structure ay (dashed lines); and (b) the film PL spectra of PPy VPV
  • Figure 11 shows the PL for single layer films (solid lines), bilayer
  • Figure 12 shows the EL of two bilayer devices (see caption) along with the
  • a conjugated polymer light-emitting device consists of an emitting material
  • Indium-tin-oxide was used as the positive transparent electrode (anode) and aluminum
  • the ITO-coated glass was most often used as the negative electrode (cathode).
  • the ITO-coated glass was most often used as the negative electrode (cathode).
  • the ITO substrates were cleaned.
  • the emitting polymer was then spin-coated onto the clean etched ITO
  • PPy was cast from formic acid solution and the copolymers of PPy V and
  • PPV tetrahydrofuran
  • Solution concentrations of the copolymer were typically s-10 mg/ml.
  • micron pore filter and stored in a hood until used.
  • the class 100 cleanroom the
  • the substrate was then immediately spun at speeds ranging from
  • Figure 3 is a graph showing the photoluminesence spectra of
  • the PL emission spectrum contains contributions from both single layers (3.05 eV and 2.05 eV), as well as from-
  • Figure 4 is a graph showing the photoluminesence spectra of a bilayer of PVK
  • the 3D plot shows three prominent features: a peak due to the
  • FIG. 5 shows graphs of the absorption and photoluminesence excitation
  • the PLEs were recorded at 2.05, 3.05,
  • the copolymer absorption is 5 times less than shown.
  • the PLE of PVK follows the abso ⁇ tion showing nearly identical features.
  • the absorption of the bilayer is the sum of the single PVK layer abso ⁇ tion and the
  • PVK peaks at 3.6 and 3.75 eV.
  • the PLE of the bilayer is also the sum of the PVK
  • copolymer peak although the copolymer peak is shifted to slightly higher energy.
  • Figure 6 shows graphs of current-voltage( — ) and brightness-voltage (G)
  • Bilayer devices were fabricated using ITO as the anode and aluminum as the
  • bilayer device demonstrates that the exciplex is responsible for the EL emission.
  • Figure 6 shows the current density-voltage and brightness-voltage characteristics for a
  • the turn-on voltage of the bilayer devices depends on the
  • thickness of the polymer layers and in this case is ⁇ 18 volts, with the brightness
  • the threshold voltage was lowered to below 5 volts while maintaining the
  • the electrons are injected from the Al electrode into the conduction band of
  • the copolymer but are confined when they reach the electron blocking PVK. Also,
  • the holes are injected into the valence band of the PVK and are confined at the
  • the buried interface implies that most of the radiative recombination will
  • Figures 8a through 8e are graphs showing the electroluminesence
  • the PVK was used as the hole-transporting layer. Blends of these polymers/copolymers with PVK show PL emission due to-
  • PPP polyparaphyenylene
  • PVP polyparaphenylene vinylenes
  • PT polythiophenes
  • hole-transporters such as PPPs, PPVs, polymethyl
  • Figure 9 is a graph showing the photoluminesence spectra of several
  • Figures 10 and 1 1 show the PL spectra of single layers of PVK and each of the
  • Figure 10 shows (a) the film PL
  • PVK/PPyVPV structure ay (dashed lines); and (b) the film PL spectra of PPy VPV
  • Figure 11 shows the PL for single layer films (solid lines), bilayer
  • Figure 12 shows the EL of two bilayer devices (see caption) along with the
  • the exciplex is also the primary species of

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent comprenant une première couche polymère (1) comme une couche de transport de trous/blocage d'électrons et une deuxième couche polymère (2) comme une couche émissive de transport d'électrons, la première couche et la deuxième couche étant en contact électrique afin de former une interface capable de produire une émission de type exciplexe sur un courant passant dans l'interface. La première couche est dotée d'une possibilité de transport de trous supérieure à celle de la deuxième couche, et la deuxième couche est dotée d'une possibilité de transport d'électrons supérieure à celle de la première couche.
PCT/US1998/004988 1997-03-12 1998-03-12 Dispositif electroluminescent sur la base d'un polymere a deux couches representant une electroluminescence d'interface WO1998040899A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU65548/98A AU6554898A (en) 1997-03-12 1998-03-12 Bilayer polymer electroluminescent device featuring interface electroluminescence
JP10539861A JP2000513153A (ja) 1997-03-12 1998-03-12 界面エレクトロルミネッセンスを特徴とする二層重合体エレクトロルミネッセントデバイス
EP98911635A EP1008164A1 (fr) 1997-03-12 1998-03-12 Dispositif electroluminescent sur la base d'un polymere a deux couches representant une electroluminescence d'interface
CA002307035A CA2307035A1 (fr) 1997-03-12 1998-03-12 Dispositif electroluminescent sur la base d'un polymere a deux couches representant une electroluminescence d'interface

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3623297P 1997-03-12 1997-03-12
US60/036,232 1997-03-12

Publications (2)

Publication Number Publication Date
WO1998040899A1 true WO1998040899A1 (fr) 1998-09-17
WO1998040899A9 WO1998040899A9 (fr) 1999-03-11

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PCT/US1998/004988 WO1998040899A1 (fr) 1997-03-12 1998-03-12 Dispositif electroluminescent sur la base d'un polymere a deux couches representant une electroluminescence d'interface

Country Status (5)

Country Link
EP (1) EP1008164A1 (fr)
JP (1) JP2000513153A (fr)
AU (1) AU6554898A (fr)
CA (1) CA2307035A1 (fr)
WO (1) WO1998040899A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000133453A (ja) * 1998-10-22 2000-05-12 Idemitsu Kosan Co Ltd 有機エレクトロルミネッセンス素子およびその製造方法
CN100466332C (zh) * 2006-01-18 2009-03-04 中国科学院化学研究所 一种发光颜色可调控的有机发光二极管的制备方法
CN100479228C (zh) * 2006-08-08 2009-04-15 中国科学院化学研究所 基于电子受体材料的蓝光有机发光二极管的制备方法
JP2010232696A (ja) * 2010-07-16 2010-10-14 Sumitomo Chemical Co Ltd 有機エレクトロルミネッセンス素子およびその製造方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5554450A (en) * 1995-03-08 1996-09-10 Eastman Kodak Company Organic electroluminescent devices with high thermal stability
US5601903A (en) * 1993-08-27 1997-02-11 Sanyo Electric Co., Ltd. Organic electroluminescent elements
US5604398A (en) * 1994-09-16 1997-02-18 Electronics And Telecommunications Research Institute Electroluminescence light-emitting device with multi-layer light-emitting structure

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5601903A (en) * 1993-08-27 1997-02-11 Sanyo Electric Co., Ltd. Organic electroluminescent elements
US5604398A (en) * 1994-09-16 1997-02-18 Electronics And Telecommunications Research Institute Electroluminescence light-emitting device with multi-layer light-emitting structure
US5554450A (en) * 1995-03-08 1996-09-10 Eastman Kodak Company Organic electroluminescent devices with high thermal stability

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000133453A (ja) * 1998-10-22 2000-05-12 Idemitsu Kosan Co Ltd 有機エレクトロルミネッセンス素子およびその製造方法
CN100466332C (zh) * 2006-01-18 2009-03-04 中国科学院化学研究所 一种发光颜色可调控的有机发光二极管的制备方法
CN100479228C (zh) * 2006-08-08 2009-04-15 中国科学院化学研究所 基于电子受体材料的蓝光有机发光二极管的制备方法
JP2010232696A (ja) * 2010-07-16 2010-10-14 Sumitomo Chemical Co Ltd 有機エレクトロルミネッセンス素子およびその製造方法

Also Published As

Publication number Publication date
JP2000513153A (ja) 2000-10-03
AU6554898A (en) 1998-09-29
CA2307035A1 (fr) 1998-09-17
EP1008164A1 (fr) 2000-06-14

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