EP0910930A1 - Systemes electroluminescents fonctionnant a l'aide de systemes de melanges - Google Patents

Systemes electroluminescents fonctionnant a l'aide de systemes de melanges

Info

Publication number
EP0910930A1
EP0910930A1 EP97933643A EP97933643A EP0910930A1 EP 0910930 A1 EP0910930 A1 EP 0910930A1 EP 97933643 A EP97933643 A EP 97933643A EP 97933643 A EP97933643 A EP 97933643A EP 0910930 A1 EP0910930 A1 EP 0910930A1
Authority
EP
European Patent Office
Prior art keywords
electroluminescent
hole
zone
transporting
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP97933643A
Other languages
German (de)
English (en)
Inventor
Rolf Wehrmann
Andreas Elschner
Martin Hueppauff
Christoph Jonda
David Terrell
Dirk Quintens
Hartwig Andries
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Robert Bosch GmbH
Bayer AG
Original Assignee
Robert Bosch GmbH
Bayer AG
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 Robert Bosch GmbH, Bayer AG filed Critical Robert Bosch GmbH
Publication of EP0910930A1 publication Critical patent/EP0910930A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
    • 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
    • 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

  • An electroluminescent (EL) arrangement is characterized in that it emits light under the application of an electrical voltage under current flow.
  • LEDs light emitting diodes
  • the emission of light is caused by the fact that positive charges ("holes”, holes) and negative charges (“electrons", electrons) recombine while emitting light
  • Polymers such as poly- (p-phenylene) and poly- (p-phenylenevinylne (PPV)) are also described as electroluminescent polymers G Leising et al, Adv Mater 4 (1992) No. 1, Fnend et al, J Che Soc, Chem Commun 32 (1992),
  • EP-A 0 294 061 presents an optical modulator based on polyacetylene
  • the organic EL arrangements usually contain one or more layers of organic charge transport compounds.
  • the basic structure in the order of the layers is as follows
  • Layers 3 to 7 represent the electroluminescent element
  • an EL arrangement consists of two electrodes, between which there is an organic layer that includes all functions - including that of the emission of light - such systems are described in 7 B in the application WO 90/13148 on the basis of poly (p-phenylene vinyl)
  • Multi-layer systems can be built up by vapor deposition processes, in which the layers are applied successively from the gas phase, or by casting processes. Casting processes are preferred due to the higher process speed chains. However, the batching process can already be applied
  • the object of the present invention is to provide electroluminescent arrangements with high luminance, the mixture to be applied being pourable It has been found that electroluminescent arrangements which contain the below-mentioned blend system meet these requirements.
  • zone is also to be equated with layer
  • the present invention relates to electroluminescent arrangements comprising a substrate, an anode, an electroluminescent element and a cathode, wherein at least one of the two electrodes is transparent in the visible spectral range and can contain the electroluminescent element in order
  • a hole-injecting zone, hole-transporting zone, electroluminescent zone, electron-transporting zone and / or an electron-injecting zone characterized in that the hole-injecting and / or hole-transporting zone is an optionally substituted T ⁇ s-l, 3,5- (aminophenyl) benzene compound A or a mixture thereof and the electroluminescent element is optionally a further functionalized compound from the group of the hole-transporting materials, a luminescent material B and optionally
  • the hole-injecting and hole-transporting zone can contain, in addition to component A, one or more further hole-transporting compounds, at least one zone being present, individual zones being omitted and the existing zone (s) being able to take on several tasks
  • a zone can perform several tasks, that is to say that a zone can contain, for example, hole-injecting, hole-transporting, electroluminescent, electron-injecting and / or electron-transporting substances
  • the electroluminescent element may further contain one or more transparent polymeric binders C.
  • the optionally substituted 1 ⁇ s- l, 3,5- (aminophenyl) benzene compound A represents an aromatic tertiary amino compound of the general formula (I)
  • R represents hydrogen, optionally substituted alkyl or halogen
  • R 1 and R 4 independently of one another represent optionally substituted C, -C 10 alkyl, alkoxycarbonyl-substituted C, -C 10 alkyl, or optionally substituted aryl, aralkyl or cycloalkyl
  • R 'and R 4 independently of one another preferably represent C ] -C 6 -alkyl, in particular methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, C ] -C 4 -alkoxcarbonyl -C ] -C f) alkyl, such as methoxy, ethoxy, Pi opoxy, butoxycarbonyl-C
  • R 1 and R 4 are particularly preferably independently of one another unsubstituted phenyl or naphthyl or in each case one to three times by methyl, ethyl, n- or isopropyl. Methoxy, ethoxy, n- and / or iso-propoxy substituted phenyl or naphthyl
  • R ⁇ is preferably hydrogen, C j -C ⁇ alkyl, such as methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, or chlorine
  • T ⁇ s-nitrophenyl compound can be converted into the T ⁇ s-aminophenyl compound, for example by generally known catalytic hydrogenation, for example in the presence of Ranev nickel (Houben-Weyl 4 / IC, 14 -102, Ullmann (4) ü, 135- 148)
  • Ranev nickel Houben-Weyl 4 / IC, 14 -102, Ullmann (4) ü, 135- 1478
  • the amino compound is reacted in a generally known manner with substituted halogenobenzenes
  • hole conductors for example in the form of a mixture with component A, can optionally be used to build up the electroluminescent element.
  • it can be one or more compounds of the formula (I), which also comprises mixtures of isomeres on the other hand also with mixtures of hole-transporting compounds
  • the compounds can be used in any ratio between 0 and 100% by weight (based on mixture A)). In a preferred embodiment, 1 to 99% by weight and 99 to 1% by weight , particularly preferably 5 to 95% by weight and 95 to 5% by weight used. In a further preferred embodiment, 30 to 70% by weight or 70 to 30% by weight are used
  • Anthracene compounds for example 2,6,9, 10-tetraisopropoxyanthracene, oxadiazole compounds, for example 2,5-B ⁇ s (4-dimethylamino-nophenyl) -1, 3,4-oxadiazole, t ⁇ phenylamine compounds, for example BN, N '-D ⁇ phenyl-N, N'-d ⁇ (3-methylphenyl) - l, l' -b ⁇ phenyl-4,4'-d ⁇ - amine, aromatic tertiary amines, for example N-phenylcarbazole, N-isopropyl-carbazo!
  • T ⁇ phenylamine compounds and / or aromatic tertiary amines are preferred, the compounds mentioned by way of example being particularly preferred Materials which have hole-conducting properties and can be used as mixing partners for component A are, for example
  • the binder C) stands for polymers and / or copolymers such as polycarbonates, polyester carbonates, copolymers of styrene such as SAN or styrene acrylates, polysulfones, polymers based on monomers containing vinyl groups such as poly (meth) acrylates, polyvinylpyrrolidone, polyvinylcarbazole, vinyl acetate and vinyl alcohol polymers and copolymers, polyolefms, cychsche Olelfincopolvmere, phenoxy resins, etc. Mixtures of different polymers can also be used.
  • the polymeric binders C) have molecular weights of 10,000 to 2,000,000 g / mol, are soluble and film-forming and are in the visible spectral range transparent They are described, for example, in Encyclopedia of Polymer Science and Engineering, 2 n Ed at A Wiley-Intersciencepublication They are usually used in an amount of up to 95, preferably up to 80, by weight, based on the total weight of A) and B), used
  • Component B) represents a compound of the general formula (II)
  • n is a number from 1 to 3 and is / independently in both forms stands for atoms that complete a nucleus that consists of at least 2 condensed rings
  • the metal can be a mono-, di- or trivalent metal, for example lithium, sodium, potassium, magnesium, calcium, boron or aluminum
  • Z completes a heterocytic part of the molecule which consists of at least two condensed rings, one of which is an azole or azine ring, it being possible for further additional ahphatic or aromatic rings to be attached to the two rings which are close together
  • Suitable examples of component B) are the oxine complexes (8-hydroxyquinoline complexes) of Al ⁇ 1 , Mg 2 ', In "", Ga ⁇ Zn 2 ⁇ Be 2 1 , Li', Ca 2 'Na * or Alum ⁇ n ⁇ umt ⁇ s (5-methyloxin) R and Gall ⁇ umt ⁇ s (5-chIoro-ch ⁇ nol ⁇ n) Complexes with rare earth metals can also be used
  • One or more compounds of component B) can be used
  • the compounds or the oxine complexes according to component B are general are known and can be produced by known processes (see, for example, US Pat. No. 4,769,292)
  • the electroluminescent arrangements according to the invention are characterized in that they have a light-emitting layer which contains a mixture of components A) and B) in optionally a transparent binder C).
  • the weight ratio of A) and B) to one another is variably adjustable.
  • the proportion by weight of the sum of the proportions by weight of A) and B) in the polymeric binder is in the range from 0.2 to 98% by weight, preferably from 2 to 95% by weight, particularly preferably from 10 to 90% by weight, very particularly preferably 10 to
  • the weight ratio AB of components A and B is between 0.05 and 20, preferably 0.2 and 10 and particularly preferably between 0.3 and 8, in particular 0.3 to 7.
  • Components A) and B) can either consist of one component or a mixture of components of any composition
  • components A), B) and optionally C) are dissolved in a suitable solvent and applied to a suitable base by pouring, knife coating or spin coating.
  • a suitable solvent for example, glass or a plastic material which is transparent
  • the electrode is provided as a plastic material, for example a film made of polycarbonate
  • Polyesters such as polyethylene terephthalate or polyethylene naphthalate, polysulfone or polyimide can be used
  • Metalloxides e.g. indium tin oxide (ITO), tin oxide (NESA), zinc oxide, doped tin oxide, doped zinc oxide, etc,
  • the metal oxide and semi-transparent metal film electrodes are made by Techniques such as vapor deposition, sputtering, plating, etc., applied in a thin layer.
  • the conductive polymer films are applied from the solution using techniques such as spin coating casting, knife coating, etc.
  • the thickness of the transparent electrode is 3 nm to approximately several ⁇ m, preferably 10 nm to 500 nm
  • the electroluminescent layer is applied directly to the transparent electrode or to a charge-transporting layer which may be present as a thin film.
  • the thickness of the film is 10 to 500 nm, preferably 20 to 400 nm, particularly preferably 50 to 250 nm
  • Another charge-transporting layer can be applied to the electroluminescent layer
  • EP-A 532 798 A compilation of suitable charge-transporting intermediate layers, which can be hole- and / or electron-conducting materials, which may be present as a blend in polymeric or low molecular weight form, is listed in EP-A 532 798. Specially substituted polythiophenes are particularly suitable Which have hole-transposing properties are described, for example, in EP-A 686 662
  • the content of low-molecular hole conductor in a polymeric binder can be varied in the range from 2 to 97% by weight, the content is preferably 5 to 95% by weight, particularly preferably 10 to 90% by weight, in particular 10 to 85
  • the hole-injecting or hole-conducting zones can be deposited using various methods
  • Film-guiding hole conductors can also be used in pure form (100% ⁇ g). If appropriate, the hole-injecting or hole-conducting zone can also contain portions of an electroluminescent substance
  • Blends that consist exclusively of low molecular weight compounds can be evaporated, soluble and film-forming blends, which in addition to low molecular weight compounds can also contain a bond C) (not necessarily), can be deposited from a solution, for example by means of spin-coating casting, knife coating It is also possible to apply emitting and / or electron-conducting substances in a separate layer to the hole-conducting layer with component A. An emitting substance can also be added to the layer containing compound A ("dopant") and an electron-conducting substance can also be applied Electroluminescent substance can also be added to the electron-injecting or electron-conducting layer
  • the content of low-molecular electron conductors in the polymeric binder can be varied in the range from 2 to 95% by weight, the content is preferably 5 to 90% by weight, particularly preferably 10 to 85% by weight.
  • Film-forming electron conductors can also be used in pure form (100% ) are used
  • the counterelectrode consists of a conductive substance that can be transparent.
  • metals eg Al, Au, Ag, Mg, In, etc or alloys and oxides thereof are suitable, which can be applied by techniques such as sputtering, platinum plating
  • the arrangement according to the invention is by two electrical leads (z
  • the arrangements When a direct voltage is applied in the range from 0.1 to 100 volts, the arrangements emit light of the wavelength from 200 to 2000 nm. They show photoluminescence in the range from 200 to 2000 nm
  • Electroluminescent arrangement based on a blend system
  • a 1% solution consists of 1 part by weight A, 1 part by weight B and 4 Weight points C in dichloroethane is distributed with a commercial spin coater at a speed of 400 / min on a ITO coated glass plate (Baltracon 255 from Balzers)
  • the layer thickness is 100 nm
  • the arrangement After contacting and application of an electric field, the arrangement shows visually recognizable electroluminescence in the green spectral range from approximately 7 V.
  • the brightness is 355 cd / m 2 at a current of 19 mA / cm 2 and a voltage of 16 V
  • Electroluminescent arrangement based on a blend system, consisting of
  • Example I Layer production and contacting are carried out as in Example I.
  • the brightness is at an applied voltage of 16 V and a current of
  • Example 4 Layer production and contacting are carried out as in Example 1.
  • the brightness is 20 V with an applied voltage and a current of 18 7 mA / cm 2 3 10 cd / m 2
  • Example 4
  • Electroluminescent arrangement based on a blend system, consisting of
  • Example 1 Layer production and contacting are carried out as in Example 1.
  • the brightness is 1 5 V with an applied voltage and a current of
  • the layer thickness is approx. 60 nm
  • a MgAg alloy in a ratio of 10 1 is applied as the counter electrode by thermal code position.
  • the system emits green light.
  • the diode emits green light
  • a 1.5% solution of A) in chloroform is distributed with a commercially available spin coater at a speed of 1000 rpm onto an ITO-coated glass plate (Baltracon 255 from Balzers).
  • the layer is 120 nm
  • Al is applied as the counter electrode by thermal evaporation
  • electroluminescence After contacting and application of an electrical voltage, electroluminescence can be detected from 8 V with a Si photodiode. At a voltage of 20 V a current of 25 mA / cm 2 flows and the luminance is 2 cd / m 2. The color of the electroluminescence is blue

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

Abstract

L'invention concerne des systèmes électroluminescents comprenant un substrat, une anode, un élément électroluminescent et une cathode, au moins une des deux électrodes étant transparente dans le domaine spectral visible et l'élément électroluminescent pouvant contenir à la suite: une zone à injection de trous, de transport de trous, électroluminescente, une zone de transport d'électrons et une zone d'injection d'électrons. Ces systèmes électroluminescents se caractérisent en ce que la zone d'injection de trous et de transport de trous contient un composé tris-1,3,5-(aminophényle)benzène A éventuellement substitué ou un mélange dudit composé. L'élément électroluminescent contient éventuellement un autre composé fonctionnalisé du groupe des matériaux de transport de trous, un matériau luminescent B et éventuellement des matériaux de transport d'électrons. Outre le constituant A, la zone d'injection et de transport de trous peut contenir un ou plusieurs autres composés de transport de trous. Au moins une zone est présente, des zones individuelles peuvent être supprimées et la(les) zone(s) présente(s) peuvent assumer plusieurs tâches.
EP97933643A 1996-07-05 1997-07-01 Systemes electroluminescents fonctionnant a l'aide de systemes de melanges Withdrawn EP0910930A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19627070A DE19627070A1 (de) 1996-07-05 1996-07-05 Elektrolumineszierende Anordnungen unter Verwendung von Blendsystemen
DE19627070 1996-07-05
PCT/EP1997/003439 WO1998002018A1 (fr) 1996-07-05 1997-07-01 Systemes electroluminescents fonctionnant a l'aide de systemes de melanges

Publications (1)

Publication Number Publication Date
EP0910930A1 true EP0910930A1 (fr) 1999-04-28

Family

ID=7798998

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97933643A Withdrawn EP0910930A1 (fr) 1996-07-05 1997-07-01 Systemes electroluminescents fonctionnant a l'aide de systemes de melanges

Country Status (7)

Country Link
US (1) US6541128B2 (fr)
EP (1) EP0910930A1 (fr)
JP (1) JP2000514591A (fr)
KR (1) KR20000022457A (fr)
AU (1) AU3692497A (fr)
DE (1) DE19627070A1 (fr)
WO (1) WO1998002018A1 (fr)

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US20020136921A1 (en) 2002-09-26
KR20000022457A (ko) 2000-04-25
WO1998002018A1 (fr) 1998-01-15
AU3692497A (en) 1998-02-02
DE19627070A1 (de) 1998-01-08
US6541128B2 (en) 2003-04-01
JP2000514591A (ja) 2000-10-31

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