WO2005064702A1 - Diode electroluminescente organique/macro moleculaire - Google Patents

Diode electroluminescente organique/macro moleculaire Download PDF

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WO2005064702A1
WO2005064702A1 PCT/CN2004/001417 CN2004001417W WO2005064702A1 WO 2005064702 A1 WO2005064702 A1 WO 2005064702A1 CN 2004001417 W CN2004001417 W CN 2004001417W WO 2005064702 A1 WO2005064702 A1 WO 2005064702A1
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group
light emitting
light
layer
emitting diode
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PCT/CN2004/001417
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English (en)
Chinese (zh)
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Cao Yong
Hongbin Wu
Fei Huang
Deli Wang
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South China Uni. Of Tech.
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Publication of WO2005064702A1 publication Critical patent/WO2005064702A1/fr

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    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115—Polyfluorene; Derivatives thereof
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/82—Cathodes
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers

Definitions

  • the present invention relates to a photovoltaic device, and in particular, a light-emitting diode having a extinguished light using a conjugated polymer containing a strong polar component of a polar group or an ionic group as an electron injection layer.
  • Conjugated polymers are a class of polymers with large ⁇ bonds along the ⁇ ⁇ chain.
  • the main chain of a conjugated polymer is generally composed of C "C single and double bonds alternately connected, the polymerization unit is 01.
  • the electronic orbital of the carbon atom is sp 2 hybrid, and the three coplanar angles formed It is a 120 ° hybrid orbit.
  • the Peng orbital is bonded to the adjacent carbon atom orbital to form a planar polyacetylene frame.
  • the remaining unbonded P orbitals are perpendicular to this plane, and they overlap each other to form a common coordinator.
  • the yoke system is similar to the one-dimensional alkali metal system. According to the calculations of ⁇ and quantum theory, when the chain length of trans polyacetylene is larger than 8 carbon atoms, it has electronic conductivity, but this kind of long The yoke system is unstable, and the Peierls phase transition will cause the energy band to split.
  • the original P electrons form two subbands, namely the bond ⁇ orbital constitutes the valence band, the antibond ⁇ 3 ⁇ 43 ⁇ 4 channel constitutes the conduction band, and the bond and antibond.
  • the band gap formed by the energy gap between the orbitals.
  • Conductive polymers Due to the strong delocalization of electrons, stable excited and freely migrating carriers can be generated, which makes the conjugated polymer exhibit conductive properties.
  • Conductive polymers also have Phases of inorganic materials for the same or similar applications , Has the advantages of low density, easy processing, wide range of synthesis options, etc. Due to the conjugate nature of this kind of material structure, it can transfer charges and be excited by light, so that it can or may be used in many electronic or optoelectronic devices, For example, high-intensity light-emitting diodes (PLEDs), photodiodes, field-effect transistors (FETs), etc. Potential application prospects and a wide range of applications have prompted scientists to compete to study such conjugate materials with optoelectronic activity.
  • PLEDs high-intensity light-emitting diodes
  • FETs field-effect transistors
  • High ⁇ f with aromatic ring or heterocyclic structure is usually Who absorbs 300 "600 nanometers of photons and releases the corresponding energy when they form a key orbit from the anti-bond orbit.
  • photons of the corresponding wavelength in the visible region are emitted, which is the electroluminescence process of high- ⁇ T materials.
  • the light-emitting process of this type of electroluminescent device injects holes and electrons from the positive and negative electrodes into the light-emitting layer, and the hole-electron pair is electrically transferred in the polymer layer and captured each other to form an electrically neutral
  • the bound excited state is the exciton state, and the radiation of the exciton emits a corresponding photon.
  • the electroluminescence process of the high-emitting materials includes the formation of exciton and the decay of the exciton.
  • the former includes the injection of carriers, the transport of carriers, and the mutual trapping shape of the carriers.
  • the latter includes competition between radiation and emission processes.
  • S 0
  • the intersystem string ® from the triplet to the singlet state is almost impossible, so the spin is allowed to govern Luminescence (fluorescence) comes only from the singlet state.
  • the first condition is to have an efficient and balanced carrier injection and.
  • the simplest structure of the existing organic conjugated polymer light-emitting diode is a single-layer sandwich type, as shown in FIG. 1, which is composed of a cathode 1, a light-emitting layer 2, a hole injection layer 3, an anode 4, and a substrate 5 in order.
  • a cathode 1 barium / aluminum metal is used for the cathode
  • a conjugated polymer film is used for the light-emitting layer
  • a PEDOT film is used for the hole injection layer
  • an indium tin oxide conductive layer is used for the anode
  • a glass is used for the substrate.
  • the anode one uses indium tin oxide (IT0), which is transparent to visible light and has a high work function, as the electrode material, and the spin-coated high polymer ⁇ 3 ⁇ 4 material PEDOT layer is used as the electrode layer.
  • I0 indium tin oxide
  • PEDOT spin-coated high polymer ⁇ 3 ⁇ 4 material
  • the cathode one Use low work function alkali metals (eg, potassium, lithium, cesium) or alkaline earth metals (eg, calcium, barium, etc.).
  • the barrier height of electron injection (equal to the difference between the LIM0 level of the conjugated polymer material and the Fermi level of aluminum) is much higher than the potential height of the hole injection (equal to the conjugated polymer material) Difference between the HC 0 energy level and the Fermi level of indium tin oxide), and its teleportation hole mobility is much lower, in this case, the application of stable metals in the production of high-performance electroluminescent devices is greatly limited .
  • lithium fluoride, etc. or surfactants have excellent effects in combination with aluminum, but they are much less effective for other metals with higher work functions.
  • the electrode stabilizes the metal element to realize the electron injection of the light emitting diode.
  • the purpose of the present invention is to provide a m / polymer light-emitting diode, and use a conjugated polymer containing a polar group or an ionic group of a strongly polar component as its electron injection layer.
  • the yoke polymer has excellent electron injection characteristics, and the obtained L / high light emitting diode has high quantum efficiency.
  • the object of the present invention is also to provide a high-molecular light-emitting diode, using a conjugated polymer containing a strong polar component containing a polar group or an ionic group as its electron injection layer.
  • High work function metal which has the same or more quantum efficiency as the low work function pull-in electrode, has long-term stability and has a light emitting diode, which is suitable for high flat display.
  • the a / high light emitting diode of the present invention is composed of a cathode, a light emitting diode, an anode, and a substrate, and is characterized in that a hole injection layer (3) is provided between the light emitting layer (2) and the anode (4).
  • An electron injection layer (6) is provided between the cathode (1) and the light emitting layer (2), and the electron injection layer uses a polar unit conjugated polymer containing a polar group or an ionic group.
  • the light-emitting layer (2) and the electron injection layer (6) can also be combined into one layer, and this layer is a hair emission at the same time;) fc and the electron injection layer adopt polar units containing polar groups or ionic groups Conjugated polymers.
  • the organic / polymer light emitting diode of the present invention has m / high light emission, which is formed by stacking a cathode 1, a light emitting layer 2, a hole injection layer 3, an anode 4, and a substrate 5 in this order.
  • an electron 3 ⁇ 4 layer 6 is provided between the cathode and the light-emitting layer.
  • the 3 ⁇ 4 electron injection layer uses a conjugated polymer of a polar unit containing a polar group or an ionic group.
  • a conjugated polymer containing a polar unit of a polar group or an ionic group has the following structure:
  • A is a polar component containing a polar group or an ionic group, and has a combination of one or more of the following structures:
  • the components of the ionic group have one or more of the following structures ⁇
  • G is a heterocyclic ring that may contain sulfur, nitrogen, and selenium, such as benzothiadiazole, benzoseladiazole;
  • a conjugated polymer containing polar units containing polar groups or ionic groups can be obtained by coupling reactions of ⁇ ⁇ to Mil Suzuki.
  • the cathode metal may be a low work function metal or a high work function metal.
  • ⁇ m / high light-emitting diodes In order to overcome the low work function metal's easy reaction with water and oxygen, which causes rapid aging and failure of the device, and the processing difficulties caused by iWd, and to overcome the low electron injection efficiency of high work function metal, ⁇ m / high light-emitting diodes During the process, a solution of the above polar group or ionic group polymer is rotated, and a thin layer is coated on the light-emitting layer to form an electron injection layer, and then a high-efficiency metal is plated thereon. Get good environmental stability! Efficient! Balanced electrons are injected into the light emitting diode.
  • the high work function metals are gold, aluminum, copper, silver, indium, nickel, lead, tin, carbon, graphite, or alloys thereof.
  • the light-emitting layer can be a light-emitting layer commonly used in the prior art, or a copolymer of 3 ⁇ 4-inch benzene, polyfluorene, poly SPIR0 "p-benzene, ladderfPP, and phenylene acetylene substituted with a light-emitting group.
  • the copolymers synthesized by the present invention can achieve excellent electron injection to red, green and blue light emitting materials regardless of any band gap width.
  • the electrons are not affected by the work function of the yin face, even if it is a ⁇ stable metal with a work function up to 5.2eV
  • a light-emitting device with high quantum efficiency and long-term stability can be obtained similarly to the low-work-function injection electrode, which is suitable for high-flat displays.
  • This kind of materials with polar groups can be dissolved in water or methanol. Since the light emitting materials are generally insoluble, no mixing phenomenon will occur between the electron injection layer and the light emitting layer when constructing a multilayer device.
  • High work function metals have excellent air 3 ⁇ 4 ⁇ vapor stability.
  • the composite electrode composed of the polymer and the high work function metal of the present invention has stable processing performance in the atmosphere, and the stability of the device itself is greatly improved. Huge potential area in organic and high-quality display technology
  • Figure 1 is a schematic diagram of the structure of an existing organic conjugated polymer light emitting diode
  • FIG. 2 is an energy band diagram of a device using aluminum as a cathode
  • FIG. 3 is a schematic structural diagram of a light emitting diode with an iy height of the present invention
  • Figure 4 compares the presence or absence of a P1 layer when poly [2-methoxy (5- (2, monoethyl) -B3 ⁇ 4 «-l, 4-phenylacetylene)] (MEH-PPV) material is used as a cathode Curve of luminous brightness and external quantum efficiency of the device;
  • Fig. 5 is a graph comparing the luminous brightness and the external quantum efficiency curve of a device emitting green light benzene S3 ⁇ 4-generation poly-p-phenylacetylene (P-PPV) and a device with or without a PI layer when gold is used as a cathode;
  • P-PPV green light benzene S3 ⁇ 4-generation poly-p-phenylacetylene
  • FIG. 6 is a graph comparing the luminous brightness and the luminous external quantum efficiency of a device with or without a PI layer when using gold as a cathode for a blue-emitting Poly Wat Pro;
  • Fig. 7 is a graph showing the luminous brightness and the external light emitting quantum efficiency of the device with or without the P1 layer when the red-emitting ffl-PPV uses aluminum as a cathode in Fig. 7;
  • 2,7-Dibromofluorene was prepared according to the method disclosed in the 1997 world patent WO 99 05184 and disclosed in "Chem. Mater” 11 (1997) 11083.
  • Example 2 Preparation of 2,7-dibromo "9, 9 ⁇ di-substituted hydride replacement sheet (Article 26 of the detailed rules) Take the preparation of 2,7-dibromo ", ⁇ dizhenzahuhu as an example. According to the method disclosed in the 1997 world patent TO 99 05184 and the" Chem Mater "11 (1997) 11083, the process 2 , 7-dibromo ⁇ 9, 9 ⁇ di-n-octyl hydrazone.
  • the 2,7-dibromo-9,9 "di-substituted substituents include, but are not limited to, n-hexyl, n-octyl, 2-ethyl beta, decyl, and the like.
  • Example 3 Preparation of 3, 6 "" dibromocarbazole
  • Dibromo-N-substituted yttriazoles include: n-hexyl, n-octyl, 2-ethylhexyl, etc., but is not limited thereto.
  • Example 5 Preparation of 9, 9 ⁇ disubstituted-2,7-diborate hydrazone
  • the substituents in 9, 9 ⁇ disubstituted -2, 7-diborate hydrazone include: n-hexyl, n-hexyl, 2-ethylhexyl, decyl, but not limited thereto.
  • Substitution-3, Substitution in carbazole 3 ⁇ 4 ⁇ include: but not limited to n-hexyl, n-octyl, 2-ethylhexyl and the like.
  • Example 7 Preparation of dibromo group at side 9 with amine-containing functional group side chain
  • Substituents in 2,7-dibromo ⁇ , 9 "di-B3 ⁇ 4" substitutions include: ⁇ , ⁇ dimethylaminopropyl, ⁇ , ⁇ -dimethylaminoethyl, ⁇ , "dimethylaminohexyl, N ⁇ ethylaminoethyl and the like are not limited thereto.
  • Example 8 Preparation of dibromo group at the 9-position with a sulfonic acid group-containing functional side chain
  • the substituents in 2,7-dibromo ⁇ 9, 9 ⁇ disulfonium include: sulfopropyl, potassium sulfopropyl, sulfobutyl, potassium sulfonate and the like, but are not limited thereto.
  • the pendant substituents of the dibromocarbazole containing a sulfonic acid functional group side chain include: sulfopropyl, potassium sulfopropyl, sodium sulfonate butyl, potassium sulfonate, but are not limited thereto.
  • Example 11 Preparation of p-dibromobenzene with a side chain containing an amine-containing functional group
  • Substitute page (rule 26) Take the preparation of 2,5-bis (3- [N, ⁇ diethylamino] -1-oxopropyl-1,4-dibromobenzene as an example. Press "Macromolecules" 30 (1997 ) The method disclosed in 7686 is used to prepare 2, 5-bis (3- [N, diethyl 3 ⁇ 43 ⁇ 4] -1-oxopropane S ⁇ l, 4-dibromobenzene.
  • the side chain with amine group in p-dibromobenzene with side chain containing amine functional group includes N, dimethylaminopropyl, ⁇ , ⁇ -dimethylaminoethyl, ⁇ , N-dimethylaminohexyl, N, ⁇ diethylaminoethyl, and the like, but are not limited thereto.
  • Example 12 Preparation of 4, 7-dibromo-2,1,3-benzoselenediazole according to the method and method disclosed in J. Chem. Soc. (1963) 4767. 7-dibromo-2,1,3-benzoselenediazole. Weigh 2,1,3-benzoselenediazole (1.83 g, 0.01 mole) and silver sulfate (3.12 g, 0.01 mole), dissolve in 20 ml of concentrated sulfuric acid, stir, and add bromine (3.2 g, 0.02 mole) dropwise.
  • ITO conductive glass square resistance ⁇ 20 ⁇ / port, pre-cut into 15 mm X 15 mm square pieces.
  • IT0 nets were bombarded with plasma in an oxygen plasma etcher for 10 minutes.
  • PVK, PED0T: PSSPVK were purchased from Aldrich, and the solution was prepared with tetrachloroethane.
  • PED0T PSS water dispersion (about 1%) was purchased from Bayer's buffer layer and spin-coated with a homogenizer (KW-4A). The thickness was determined by the solution concentration and speed.
  • a surface profiler Tritek Alpha-Tencor500 was used. ) Measured monitoring. After film formation, the solvent residue and hard film were driven out in a constant temperature vacuum oven.
  • the fluorescent conjugated polymer was weighed in a clean bottle, it was transferred to a nitrogen-resistant film-forming glove box (VAC company), dissolved in toluene, and filtered through a 0.45 micron filter membrane.
  • the optimal thickness of the polymer light-emitting layer is 70 to 90 nm.
  • the film thickness was measured with a TENCORALFA-STEP-500 surface profiler.
  • P1 was dissolved in methanol (a small amount of acetic acid was added) to prepare a 0.04% 0. two concentration solution. Profit
  • a 90-nm-thick poly [2-methoxy (5- (2, monoethyl) -hexadecane-1,4-phenyleneacetylene]] (MEtt-PPV) conjugated polymer film was used as the light-emitting layer.
  • A1 Function of A1 (44 electron volts), Au (5.3 electron volts), alternating at different concentrations (2, 5-bis (3- [N, F "diethylamino] 1-oxypropyl 3 ⁇ 4 ⁇ 1, 4 —Benzene—co- ⁇
  • a thin layer of P1 is spin-coated under a methanol solution of 9 "di-copolymer (P1) in a light-emitting layer; ⁇ as an electron injection layer, vacuum-evaporated over the electron injection layer P1 covered with aluminum
  • a double-layered structure of gold or gold is used as a cathode to produce a polymer light emitting diode emitting orange-red light.
  • a low work function Ba (2.7 electron volts) / A1 and a high work function are used.
  • the conventional light-emitting device prepared by directly vapor-depositing Al (4.2 electron volts) and Au (5.3 electron volts) on 3 ⁇ 4 MEHPPV was used as a reference device, and the measurement results are shown in Table 1.
  • the comparative poly [2— Methoxy (5- (2, monoethyl) -hexyloxy-1,4-phenylethyl block)] (MEH-PPV) material, with or without P1 layer when using aluminum as cathode The device's luminous effect shines outside quantum efficiency.
  • MEHPPV Pl (0.0%) aluminum 7.0 24.7 2247 229
  • Table 2 is based on the 3 ⁇ 43 ⁇ 43 ⁇ 43 ⁇ 4 performance of the device using PI as the electronic layer for the material P "PPV, and the device structure is ITO ⁇ EDOT / ADS129 / Al (Au) m electron 3 ⁇ 4 ⁇ cathode mt. External quantum efficiency fiber (Amp. Square meter) eo )
  • Example 2 to replace the polymer light-emitting layer with; 3 ⁇ 4 light Pho material PFO, spin-coated a 40nm PW layer on the layer, to improve the injection of holes, the others remain unchanged.
  • the experimental results are summarized in Table 3.
  • the light-emitting poly PF0 uses the gold as the cathode and the light emission of the device with or without the P1 layer 3 ⁇ 4 3 ⁇ 4 3 ⁇ 4 Quantum efficiency.
  • Table 3 shows the electrical properties of the device using PP1 as the electron 3 ⁇ 4 ⁇ layer.
  • the device structure is ITO PEDOT P ADS ⁇ g / Pl / Al (Au)
  • Example 2 was repeated.
  • the electron injection layer was replaced with a polymer (P2) having a sulfo 3 ⁇ 4 group functional group in the side chain, and the others were unchanged.
  • P2 polymer having a sulfo 3 ⁇ 4 group functional group in the side chain
  • Table 4 The experimental results are summarized in Table 4.
  • Figure 7 when the red-emitting MEH-PPV uses aluminum as the cathode, the light emission brightness and external light emission quantum efficiency of the device with or without the P1 layer are compared.
  • Example 2 was repeated.
  • the electron injection layer was replaced with a three-component copolymer containing a narrow band gap (narrow band gap monomer benzothiadi (P3) as the electron injection layer.
  • the other cakes were unchanged.
  • the experimental results are summarized in Table 5.
  • Table 5 Based on the red light material poly [2-methoxy (5- (2, monoethyl) -hexyloxy-1, 4-phenylphenylacetylene)] (Mffi-PPV), with a narrow band gap monomer benzothia
  • the ternary copolymer of a diazole e.g., the electroluminescence properties of a device as an electric layer
  • the device structure is ITO / PEDOT / MEHPPV / P3 / A1 m electrons, cathode voltage, current, and efficiency.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

La présente invention concerne une diode électroluminescente organique/macro moléculaire composée d'une cathode (1), d'une couche luminescente (2), d'une couche d'injection par trous (3), d'une anode (4) et d'un substrat (5) par la lamilation séquentielle. Une couche d'injection d'électrons (6) est prévue entre la cathode (1) et la couche luminescente (2), cette couche d'injection d'électrons adopte le polymère conjugué qui contient une unité de polarité de groupe de polarité ou de groupes de ionicité, cette cathode adopte un métal à fonction de fonctionnement élevée dont la fonction de fonctionnement est supérieure ou égal à 3.6eV. Cette invention permet d'obtenir une diode électroluminescente organique/macro moléculaire qui possède la même efficacité quantique ou une efficacité encore supérieure de fonctionnalité de fonctionnement réduit d'une électrode d'injection, sa stabilité de longue durée est améliorée, cette diode électroluminescente organique/macromoléculaire convient pour un dispositif afficheurs panneau plat de haute résolution en couleur.
PCT/CN2004/001417 2003-12-25 2004-12-06 Diode electroluminescente organique/macro moleculaire WO2005064702A1 (fr)

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CNB2003101175185A CN100490206C (zh) 2003-12-25 2003-12-25 有机／高分子发光二极管
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WO2013167224A1 (fr) 2012-05-10 2013-11-14 Merck Patent Gmbh Formulation comprenant des composés organiques ioniques pour utilisation dans des couches de transport d'électrons
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US9601696B2 (en) 2011-03-28 2017-03-21 Sumitomo Chemical Company, Limited Electroluminescent composition and electric device with high brightness
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