WO2006077130A1 - Derives de triarylamine presentant des groupes lateraux de remplissage d'espace et utilisation de ceux-ci - Google Patents

Derives de triarylamine presentant des groupes lateraux de remplissage d'espace et utilisation de ceux-ci Download PDF

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WO2006077130A1
WO2006077130A1 PCT/EP2006/000477 EP2006000477W WO2006077130A1 WO 2006077130 A1 WO2006077130 A1 WO 2006077130A1 EP 2006000477 W EP2006000477 W EP 2006000477W WO 2006077130 A1 WO2006077130 A1 WO 2006077130A1
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phenyl
formula
biphenyl
bis
alkyl
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PCT/EP2006/000477
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Volker Lischewski
Mirko Tschunarjew
Gerhard Diener
Wolfgang Witt
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Sensient Imaging Technologies Gmbh
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Priority claimed from DE102005003634A external-priority patent/DE102005003634A1/de
Priority claimed from DE102005030314A external-priority patent/DE102005030314A1/de
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Publication of WO2006077130A1 publication Critical patent/WO2006077130A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • 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
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    • 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
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting 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
    • H10K85/30—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
    • H10K85/60—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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/791—Starburst compounds

Definitions

  • the invention relates to novel triarylamine derivatives which are provided with at least one special space-filling wing group of the general formula 2, and their use as hole transport material in electrophotographic and electroluminescent devices.
  • triarylamine derivatives including triarylamine di- and tetramers
  • the preferred luminescent material used is tris (-8-hydroxyquinolino) aluminum, the electroluminescence of which has been known since 1965.
  • This metal-chelate complex optionally doped with coumarin, luminesces green, it also being possible to use beryllium or gallium as metal.
  • phthalocyanines or biphenylyl-oxadiazole derivatives preferably N, N'-diphenyl-N, N'-bis (m-tolyl) benzidine (TPD) and N 1 N 'diphenyl-N, N'-di-naphth 1-yl-benzidine ( ⁇ -NPD) used.
  • N, N'-bis (-4'-N, N-diphenylaminobiphenylyl)) - N, N'-diphenylbenzidine (EP0650955A1) and N, N'-bis (-4 '(- N-phenyl) N-naphth-1-yl-amino-biphenylyl)) -N, N'-diphenyl-benzidine (JP2000260572) are used alone or in a bilayer association with TPD or ⁇ -NPD.
  • the life and the efficiency or its time course in the known electroluminescent devices currently do not meet the requirements of the practice and are in need of improvement.
  • unsatisfactory are the film-forming properties of the charge transport materials used and their morphological stability within a binder layer.
  • the inclination of a layer containing said charge transport materials over the service life of an electroluminescent Nescent device or arrangement within the layer to form crystallization centers depends largely on the glass transition temperature of the materials used. In general, the higher the glass transition temperature, the lower the recrystallization tendency at a given temperature, and the crystallization rate below the glass transition temperature is extremely low. High glass transition temperature compounds therefore allow a high allowable working temperature of the assemblies made therewith.
  • WO 03/064373 already discloses triarylamine derivatives which have triarylmethyl or triarylsilyl groups as the wing group and which show elevated glass transition temperatures.
  • these compounds contain an aliphatic C or Si atom surrounded by aromatics.
  • Such an aliphatic bond interrupts the conjugated system, which may be expected to negatively impact the redox potential of these compounds;
  • such aliphatic bonds are chemically relatively unstable and can be expected decomposition phenomena, which can reduce the life of these compounds under the conditions of a functioning OLED device.
  • the object of the invention is to provide novel compounds which are suitable as charge transport materials and high glass transition temperatures in the range of 100 0 C and show above, preferably in the range greater than 150 0 C, and thus are able to work the area produced with these compounds expand electroluminescent arrangements to temperature ranges from 100 ° C to about 200 ° C while at the same time to enable the lossless application by high vacuum evaporation.
  • the above-described disadvantages of compounds with aliphatic bonds should be eliminated and decomposition phenomena should be avoided.
  • the new triarylamine derivatives correspond to the general formula 1
  • n is an integer of 1-10;
  • R 1 , R 2 , R 3 and R 4 are the same or different, selected from
  • Ar 1 is the same or different and is H and phenyl or phenyl substituted by R 29 to R 33 ;
  • Ar 2 is identical or different and is H and phenyl or phenyl substituted by R 9 to R 13 ;
  • Ar 3 is the same or different and is phenyl or R 19 to R 23 -substituted phenyl, where R 5 to R 33 are identical or different and are mono- or polysubstituted by H, C 1 to Ce-alkyl, C 1 to C 6 - Alkoxy, dialkylamino (C 1 to C 6 ), diarylamino, halogen and / or phenyl, provided that at least one of R 1 to R 4 represents a biaryl-4'-yl moiety of general formula 2; R 1 to R 4 in the meaning phenyl, biphenylyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl and triarylmethy-aryl by one or
  • Ar is a structure of formula 3 or 4
  • R 34 to R 38 which are the same or different, are H or C- to C 15 alkyl, or R 38 and R 37 or R 36 and R 35 together form a 5- or 6-membered alicyclic or heterocyclic ring and thus together with the five-membered ring to which they are attached form a spiro-ring system, where O, N or S may be the heterocyclic elements; or Ar is a structure of formula 5, 6, 7 or 8 R39
  • R 39 to R 46 are identical or different and have the meaning H, phenyl, Ci to C 5 - alkyl or Ci to C 3 alkoxy, and the structures of the formulas 3, 4, 5, 6, 7 or 8 with each adjacent nitrogen atoms are connected in any free substitution position.
  • Preferred compounds are triaryl derivatives of general formula 1, in which at least one of the radicals R 1 , R 2 , R 3 and R 4 is a 2,3,4,5,6-pentaaryl-biaryl-4'yl grouping according to more general Formula 2 is in the form of Formula 2a or a 3,5-diaryl-biaryl-4'-yl grouping according to General Formula 2 in the form of Formula 2b;
  • R 5 to R 33 have the abovementioned meanings, or R has the meaning of R 5 to R 33 with the above meanings.
  • Preferred triarylamine derivatives are those of formula 1, wherein n is an integer from 1 to 4, in particular n is 1, 2 or 3, more preferably n is 1 or 3.
  • Particularly preferred compounds of the formula 1 are those in which at least one radical from R 1 to R 4 is a 2,3,4,5,6-pentaaryl-4'yl grouping of the formula 2a, where R 5 to R 33 are identical or are different and have one or more times the meaning H, alkyl, alkoxy, dialkylamino, diarylamino and halogen, and the radicals R 1 to R 4 in formula 1 are phenyl, biphenylyl, naphthyl, phenanthrenyl, antracenyl, fluorenyl or Triarylmethyl- aryl and may be substituted by one or more substituents C-rC 6 alkyl, preferably Ci-C 4 - alkyl, Ci-C 6 alkoxy, preferably Ci-C 2 alkoxy, or halogen.
  • Particularly preferred compounds of the formula 1 are furthermore those in which at least one radical from R 1 to R 4 is a 3,5-diaryl-biaryl-4'yl radical of the formula 2b where R 5 to R 33 are identical or different and have one or more times the meaning H, alkyl and / or phenyl, and the radicals R 1 to R 4 in formula 1 have the meaning phenyl, Bipheny- IyI, naphthyl, phenanthrenyl, antracenyl, fluorenyl, by one or more substituents Ci-C 6 alkyl, preferably Ci-C 4 alkyl, C 1 -C 6 -alkoxy, preferably C 1 -C 2 - alkoxy, or halogen may be substituted.
  • R 1 to R 4 a substituted or unsubstituted 3,5-diaryl-biaryl-4'-yl group of the formula 2b
  • Butyl, C 1 -C 6 -alkoxy, preferably methoxy, and substituted or unsubstituted - 3,5-diaryl-biaryl-4'-yl.Z in formula 4 is preferably selected from the following structures
  • R 34 to R 38 which may be identical or different, have the meaning H, C 1 -C 6 -alkyl or phenyl, in particular methyl or phenyl.
  • x is preferably zero or 1.
  • Y in formula 3 is preferably ethene or ethyne.
  • radicals R 37 and R 38 together with the carbon atom to which they are attached form a 5- or 6-membered alicyclic or heterocyclic ring and thus form together with the five-membered ring to which they are attached are bonded, a spiro ring system, wherein O, N or S may be the heterocyclic elements.
  • R 37 and R 38 form a spiroalkane ring.
  • radicals R 39 to R 46 which may be identical or different, are hydrogen, methyl or phenyl.
  • the radicals R 5 to R 33 are preferably H, C 1 -, C 2 -, C 3 - or C 4 -alkyl, in particular methyl or tert.
  • Halogen is preferably fluorine or chlorine.
  • n is an integer from 1 to 4, preferably 1, 2 or 3;
  • R 1 , R 2 , R 3 and R 4 which are the same or different, are
  • R 34 to R 38 which are the same or different, are H or C 1 to C 6 alkyl, or R 38 and R 37 together form a 5- or 6-membered alicyclic or heterocyclic ring and thus form together with the five-membered ring to which they are attached, a spiro-ring system, wherein O 1 N or S may be the hetero-cyclic elements.
  • Particularly preferred triarylamine derivatives of the formula 1 are furthermore compounds, in. where n is an integer 1, 2, 3 or 4; R 1 , R 2 , R 3 and R 4 are the same or different selected from phenyl, biphenylyl, naphthyl, phenanthrenyl, substituted or unsubstituted 3, 5, -Diaryl-biaryl-4'-yl of the formula 2b, wherein R is the said Meaning, wherein at least one of the radicals R 1 to R 4 is a 3, 5-diaryl-biaryl-4'-yl group of the general formula 2b, and wherein R 1 to R 4 in the meaning phenyl, biphenylyl, naphthyl or Phenanthrenyl by one or more substituents C 1 to C 6 alkyl, preferably methyl or tert.
  • Butyl, or Ci to C 6 alkoxy, preferably methoxy, Ar may represent a structure of the formula 4, where n> 1, the structure Ar may be the same
  • R 34 to R 38 which are the same or different, are H or C 1 to C 6 alkyl, preferably methyl or phenyl, or R 38 and R 37 together form a 5- or 6-membered alicyclic or heterocyclic ring and thus together with the five-membered ring to which they are attached form a spiro-ring system, where O, N or S represent the heterocyclic elements.
  • triarylamine derivatives of the formula 1 are compounds in which n is an integer 1, 2, 3 or 4;
  • R 1 , R 2 , R 3 and R 4 are the same or different, selected from phenyl, biphenylyl, naphthyl, phenanthrenyl or substituted or unsubstituted 3, 5, -Diaryl-biaryl-4'-yl of the formula 2b, wherein R is the above Meaning, wherein at least one of the radicals R 1 to R 4 is a 3, 5-diaryl-biaryl-4'-yl group of the general formula 2b, and wherein R 1 to R 4 in the meaning phenyl, biphenylyl, naphthyl or Phenanthrenyl by one or more substituents Ci to C 6 -alkyl, preferably methyl or tert. Butyl, or C 1 to C 6 alkoxy, preferably methoxy, may be substituted.
  • the invention further relates to an organic electroluminescent device having at least one hole transport layer and a luminescent layer, wherein at least one hole transport layer contains a triarylamine derivative according to formula 1.
  • a further embodiment of the invention consists in that the organic electroluminescent device has a luminescent layer which contains a triarylamine derivative according to formula 1.
  • the invention also relates to the use of triarylamine derivatives according to formula 1 as hole transport substance or luminescent substance in an organic electroluminescent device and to the use of triarylamine derivatives according to formula 1 as hole transport substance in an electrophotographic arrangement.
  • An electrophotographic device is typically constructed as follows: Over an electrically conductive metal layer, which can either be applied to a flexible base or consist of an aluminum drum, there is a charge generation layer, which has the task of exposing positive charge carriers into the charge transport layer upon exposure to inject. The assembly is electrostatically charged to several hundred volts prior to imagewise exposure.
  • the thickness of the charge generation and transport layer is typically 15-25 ⁇ m - the injected positive charge carriers (electron "holes") migrate to the negatively charged charge transport layer and thus lead to the discharge of the surface into the In the subsequent steps of an electrophotographic cycle, the imagewise charged (or discharged) surface is toned, the toner optionally transferred to a material to be printed, fixed there, and finally removed excess toner and residual charge.
  • the injected positive charge carriers electron "holes”
  • An electroluminescent device consists in principle of one or more charge transport layers, which is arranged between two electrodes, at least one of which is transparent, and contains an organic compound.
  • an applied voltage from the metal electrode usually Ca, Mg or Al, often in combination with silver
  • electrons and holes from the counter electrode are injected into the organic layer, recombine there and form singlet excitons. These go into a short time in the ground state and emit light.
  • the electroluminescent layer can now be chosen to be very thin. Due to the interchangeability of the fluorescent Irrespective of its electron transport behavior, the emission wavelength can be adjusted in the entire visible spectral range.
  • the organic electroluminescent device consists of a layer assembly consisting of a cathode, an electroluminescent layer containing an organic compound, and an anode, wherein the organic compound in the hole transport layer is a triarylamine derivative of general formula 1.
  • a preferred construction consists of the following layers:
  • a preferred arrangement is characterized in that between the transparent anode and the glass substrate layer, a dielectric spacer layer and a dielectric mirror, consisting of layer pairs, each having a layer thickness of ⁇ / 4, are arranged.
  • the cathode which may consist of Al, Mg, In, Ag or alloys of these metals, has a thickness between 100 and 5000 A.
  • the transparent anode may be made of indium tin oxide (ITO) with a thickness of 1000 - 3000 A, an indium-antimony-tin-oxide coating or a semitransparent gold layer, which is located on a glass substrate.
  • ITO indium tin oxide
  • the electroluminescent layer tris (-8-hydroxyquinolino) -aluminum according to formula
  • luminescent substance contains as usual luminescent substance, optionally contains other fluorescent substances such.
  • fluorescent substances such as Substituted triphenylbutadienes and / or 1, 3,4-oxadiazole derivatives, distyrylaryl derivatives, quinacridones, salicylidene-Zn complexes, zinc chelate complexes, DCM-doped aluminum chelate complexes, squarine derivatives, 9,10-bissytrylanthracene derivatives or europium complexes.
  • it may also contain exclusively luminescent compounds according to the invention or mixtures thereof with known luminescent substances.
  • the object of the invention could surprisingly be achieved by the compounds of general formula 1, which have at least one space-filling wing group according to formula 2.
  • These wing groups in the form of substituted or unsubstituted polyphenylbenzene units used according to the invention differ from previously known compounds having wing groups with a trityl carbon in that they contain large and branched conjugated electron systems. Due to the different energy levels caused thereby, it was surprising that such compounds nevertheless exhibit good electron conductor properties and moreover have the advantage of high glass transition temperatures.
  • R 1 to R 4 identical or different, represent a radical selected from among phenyl, biphenyl, methylphenyl, naphthyl, triarylmethyl-aryl and / or a 2,3,4,5,6-pentaaryl-biaryl-4 ' yl moiety of general formula 2a; where one, two or all of the radicals R 1 to R 4 represent a 2,3,4,5,6-pentaaryl-biaryl-4'-yl grouping of the general formula 2a in which R is the same or different and a or repeatedly has the meaning H and / or CrC 6 alkyl, preferably H and / or methyl. Particularly preferred are the compounds of the formulas 6 to 20.
  • R 1 to R 4 are a radical selected from phenyl, biphenylyl, methylphenyl, naphthyl, phenanthrenyl and a 3,5-diaryl-biaryl-4'-yl moiety of the general formula 2b; where one or two of the radicals R 1 to R 4 is a 3,5-diaryl-biaryl-4'-yl grouping of the general formula 2b, in which R is the same or different and is mono- or polysubstituted H, C 1 C 6 -AikyI, and / or phenyl, preferably H and / or methyl.
  • R 2 and R 4 are each a 3,5-diaryl-biaryl-4'-yl moiety of general formula 2b wherein R is the same or different and is H, C 1 -C 6 alkyl or phenyl, preferably H and / or methyl. Preferably, R 2 and R 4 are also identical.
  • Preferred typical examples of triarylamine derivatives according to the general formula 1 having at least one wing group of the general formula 2b are the compounds of the formulas 22 to 27.
  • At least one layer contains triarylamine derivatives according to formula 1, preferably compounds 6-20 or 22-27.
  • an additional electron transport layer contains these known electron transport materials such as Bis (-aminophenyl) -1, 3,4-oxadiazoles, triazoles or dithionene derivatives.
  • the hole transport materials used according to the invention have a high glass transition temperature of more than 150 ° C. and thus also at higher working temperatures have a very low tendency to recrystallise in the layer. Because of this, as well as due to the chemical structure of these relatively large molecules, layers made from these materials with and without binder content are very stable, allowing for the use of the common technique of "spin coating".
  • Deposited layers are free from structural defects and have a high transparency in the visible spectral range.
  • the properties mentioned make it possible to produce new organic electroluminescent devices with high luminous efficacy (> 10,000 cd / m.sup.2) with simultaneously significantly improved long-term stability (> 10,000 hours).
  • a glass apparatus consisting of a 500 ml three-necked flask, magnetic stirrer, thermometer and gas inlet tube is provided with a reflux condenser, is 2 hours. Annealed at 120 0 C, remove the bound to the glass walls of water.
  • the apparatus is purged with nitrogen and charged with 160 ml of Na-dried and N 2 -purged o-xylene while further passing nitrogen through it. With stirring, 6.3 mg of palladium acetate and 5.2 ml of a 1% solution of tri-tert-butylphosphine in dry o-xylene are added to form the catalyst complex. To the resulting clear yellow solution are added 12.9 g of sodium tert-butoxide, 13.1 g of 4,4'-dibromo-biphenyl and 59.0 g of N- (2, 3,4,5, 6-pentaphenyl) biphenyl-4'-yl) -N-biphenyl-4-yl given amine. The entire apparatus is evacuated three times and flooded with nitrogen (securiert).
  • the contents of the flask are heated to 12O 0 C in an oil bath. After about 30 minutes, the excretion of NaBr begins. The batch is allowed to react for 3 hours at 12O 0 C.
  • the contents of the flask are diluted with toluene to twice its volume and then poured with stirring into ten times the amount of methanol.
  • the crude product precipitates and can be filtered off.
  • the formed NaBr is soluble in methanol.
  • the crude product is reprecipitated from xylene with the addition of 10% silica gel and then recrystallized again from N-methylpyrrolidone. Finally, the product is sublimed in maximum vacuum ( ⁇ 10-5 torr). About 30 g of pure N, N'-bis (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) -N, N'-biphenyl-4-yl-benzidine are obtained.
  • the flask ion content is diluted to twice its volume with hot toluene and then poured with stirring into ten times the amount of methanol.
  • the crude product precipitates and can be filtered off.
  • the crude product of xylene / dodecane is reprecipitated with addition of 10% silica gel and then recrystallized from DMF again. Finally, the product is sublimed in maximum vacuum ( ⁇ 10-5 torr). About 35 g of pure N, N'-bis (N-phenyl-N- (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) -aminostilbene are obtained.
  • the synthesized compounds 6 to 20 have the following glass transition temperatures. This was determined by differential scanning calorimetry:
  • a coating is applied in ultra-high vacuum (10-8 hPa). It consists of a 55 nm thick hole injection layer, consisting of the known starburst compound 21,
  • the layers are deposited at growth rates of about 0.1 nm / s. Subsequently, a 90 nm thick aluminum cathode is applied.
  • the electroluminescent device is prepared in the same layer arrangement as in Example 5, but will be in the hole transport layer, the 2,7-bis (N-phenyl-N- (2,3,4,5,6-pentaphenyl-biphenyl-4 I - yl) -amino) -9, 9-dimethyl-fluorene used according to Example 3. The following results were achieved:
  • a glass apparatus consisting of a 500 ml three-necked flask equipped with reflux condenser, magnetic stirrer, thermometer and gas inlet tube, is baked for 2 hours at 120 ° C. to remove the water bound to the glass walls.
  • the apparatus is purged with nitrogen or argon and - with further passing of inert gas - with 160 ml of Na-dried and purged with inert gas o-xylene charged.
  • With stirring 6.3 mg of palladium acetate and 5.2 ml of a 1% solution of tri-tert-butylphosphine in dry o-xylene are added to form the catalyst complex.
  • the contents of the flask are diluted with toluene to twice its volume and then poured with stirring into ten times the amount of methanol.
  • the crude product precipitates and can be filtered off.
  • the formed NaBr is soluble in methanol.
  • the crude product is reprecipitated from xylene with the addition of 10% silica gel and then recrystallized again from N-methylpyrrolidone. Finally, the product is sublimed in maximum vacuum ( ⁇ 10-5 torr).
  • Example 7 In the same apparatus as in Example 7 and in an analogous procedure, starting from 160 ml of Na dried over Na and purged with N2 o-xylene, 6.3 mg palladium acetate and 5.2 ml of a 1% solution of tri-tert. butylphosphine in dry o-xylene, 12.9 g of sodium tert-butoxide, 20.41 g of N, N'-di-p-tolylbenzidine and 44.24 g of 1- (4-bromophenyl) -3,5- diphenyl-benzene in the course of 4 hours at 120 0 C, the crude product prepared.
  • the flask ion content is diluted to twice its volume with hot toluene and then poured with stirring into ten times the amount of methanol.
  • the crude product precipitates and can be filtered off.
  • the crude product is reprecipitated from xylene with the addition of 10% silica gel and then recrystallized once again from DMF / NMP mixture 1: 1. Finally, the product is sublimed in maximum vacuum ( ⁇ 10-5 torr).
  • a coating is applied in ultra-high vacuum (10-8 hPa). It consists of a 55 nm thick hole injection layer, consisting of the known starburst compound 21,
  • the layers are deposited at growth rates of about 0.1 nm / s Thick aluminum cathode applied.
  • a voltage is applied between the ITO electrode and the aluminum electrode.
  • the power of the emitted light was measured with a large area Si photodiode mounted directly below the glass slide.

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  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne de nouveaux dérivés de triarylamine comprenant au moins un groupe ramifié spécifique, qui sont utilisés comme matériau de transport de trou dans des dispositifs électrophotographiques et électroluminescents. Selon cette invention, le dispositif organique électroluminescent est constitué d'une structure en couches formée d'une cathode, d'une couche électroluminescente contenant un composé organique et d'une anode. Ledit composé organique dans la couche de transport de trou est un nouveau dérivé de triarylamine de formule générale (1).
PCT/EP2006/000477 2005-01-21 2006-01-17 Derives de triarylamine presentant des groupes lateraux de remplissage d'espace et utilisation de ceux-ci WO2006077130A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102005003634.1 2005-01-21
DE102005003634A DE102005003634A1 (de) 2005-01-21 2005-01-21 Triarylamin-Derivate II mit raumfüllenden Seitengruppen und Verwendung in elektrolumineszenten und elektrofotografischen Vorrichtung
DE102005030314A DE102005030314A1 (de) 2005-06-23 2005-06-23 Triarylamin-Derivate mit Triphenylbenzol-Einheiten als raumfüllender Seitengruppe und deren Verwendung
DE102005030314.5 2005-06-23

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WO2006077130A1 true WO2006077130A1 (fr) 2006-07-27

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WO2007080704A1 (fr) * 2006-01-13 2007-07-19 Idemitsu Kosan Co., Ltd. Derives amine aromatiques et dispositifs electroluminescents organiques les utilisant
EP2075309A3 (fr) * 2007-12-31 2009-09-23 Gracel Display Inc. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
JP2013508380A (ja) * 2009-10-19 2013-03-07 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電子用途用のトリアリールアミン化合物
US8461282B2 (en) 2007-05-22 2013-06-11 National Taiwan University (Pentaphenyl)phenyl group containing compound, polymeric derivative thereof and method for forming the same
WO2013118847A1 (fr) * 2012-02-10 2013-08-15 出光興産株式会社 Dérivé d'amine aromatique, élément électroluminescent organique et dispositif électronique
JP2014205654A (ja) * 2013-04-16 2014-10-30 東ソー株式会社 ２，５−ジアミノカルバゾール化合物及びその用途
CN106699733A (zh) * 2016-12-23 2017-05-24 长春海谱润斯科技有限公司 一种芳香族胺类衍生物及其制备方法和应用
JPWO2016199743A1 (ja) * 2015-06-11 2018-04-12 保土谷化学工業株式会社 アリールアミン化合物および有機エレクトロルミネッセンス素子
US9960360B2 (en) 2006-06-22 2018-05-01 Idemitsu Kosan Co., Ltd. Organic electroluminescent device using aryl amine derivative containing heterocycle

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WO2003064373A1 (fr) * 2002-01-28 2003-08-07 Sensient Imaging Technologies Gmbh Derives de triarylamines et leur utilisation dans des dispositifs organiques electroluminescents et electrophotographiques
US20040054232A1 (en) * 2000-09-05 2004-03-18 Idemitsu Kosan Co., Ltd. Novel arylamine compound and organic electroluminescence device

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US20040054232A1 (en) * 2000-09-05 2004-03-18 Idemitsu Kosan Co., Ltd. Novel arylamine compound and organic electroluminescence device
WO2003064373A1 (fr) * 2002-01-28 2003-08-07 Sensient Imaging Technologies Gmbh Derives de triarylamines et leur utilisation dans des dispositifs organiques electroluminescents et electrophotographiques

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007080704A1 (fr) * 2006-01-13 2007-07-19 Idemitsu Kosan Co., Ltd. Derives amine aromatiques et dispositifs electroluminescents organiques les utilisant
US9960360B2 (en) 2006-06-22 2018-05-01 Idemitsu Kosan Co., Ltd. Organic electroluminescent device using aryl amine derivative containing heterocycle
US11678571B2 (en) 2006-06-22 2023-06-13 Idemitsu Kosan Co., Ltd. Organic electroluminescent device using aryl amine derivative containing heterocycle
US11152574B2 (en) 2006-06-22 2021-10-19 Idemitsu Kosan Co., Ltd. Organic electroluminescent device using aryl amine derivative containing heterocycle
US11094888B2 (en) 2006-06-22 2021-08-17 Idemitsu Kosan Co., Ltd. Organic electroluminescent device using aryl amine derivative containing heterocycle
US10283717B2 (en) 2006-06-22 2019-05-07 Idemitsu Kosan Co., Ltd. Organic electroluminescent device using aryl amine derivative containing heterocycle
US8461282B2 (en) 2007-05-22 2013-06-11 National Taiwan University (Pentaphenyl)phenyl group containing compound, polymeric derivative thereof and method for forming the same
EP2075309A3 (fr) * 2007-12-31 2009-09-23 Gracel Display Inc. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
JP2009215281A (ja) * 2007-12-31 2009-09-24 Gracel Display Inc 新規な有機エレクトロルミネセント化合物及びこれを使用する有機エレクトロルミネセント素子
JP2013508380A (ja) * 2009-10-19 2013-03-07 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電子用途用のトリアリールアミン化合物
WO2013118847A1 (fr) * 2012-02-10 2013-08-15 出光興産株式会社 Dérivé d'amine aromatique, élément électroluminescent organique et dispositif électronique
JP2014205654A (ja) * 2013-04-16 2014-10-30 東ソー株式会社 ２，５−ジアミノカルバゾール化合物及びその用途
EP3309141A4 (fr) * 2015-06-11 2019-01-16 Hodogaya Chemical Co., Ltd. Composé arylamine et élément électroluminescent organique
JPWO2016199743A1 (ja) * 2015-06-11 2018-04-12 保土谷化学工業株式会社 アリールアミン化合物および有機エレクトロルミネッセンス素子
CN106699733A (zh) * 2016-12-23 2017-05-24 长春海谱润斯科技有限公司 一种芳香族胺类衍生物及其制备方法和应用

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