EP1470100A1 - Derives de triarylamines et leur utilisation dans des dispositifs organiques electroluminescents et electrophotographiques - Google Patents

Derives de triarylamines et leur utilisation dans des dispositifs organiques electroluminescents et electrophotographiques

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EP1470100A1
EP1470100A1 EP02799037A EP02799037A EP1470100A1 EP 1470100 A1 EP1470100 A1 EP 1470100A1 EP 02799037 A EP02799037 A EP 02799037A EP 02799037 A EP02799037 A EP 02799037A EP 1470100 A1 EP1470100 A1 EP 1470100A1
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phenyl
formula
different
aryl
radicals
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Andreas M. Richter
Volker Lischewski
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Sensient Imaging Technologies GmbH
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Sensient Imaging Technologies GmbH
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Definitions

  • Triarylamine derivatives and use in organic electroluminescent and electrophotographic devices are Triarylamine derivatives and use in organic electroluminescent and electrophotographic devices
  • the invention relates to new triarylamine derivatives which are equipped with special space-filling wing groups and to their use as hole transport material in electrophotographic and electroluminescent devices.
  • Tris (-8-hydroxyquinolino) aluminum the electroluminescence of which has been known since 1965, is currently used as the preferred luminous material.
  • This metal-chelate complex optionally doped with coumarin, luminescent green, wherein beryllium or gallium can also be used as the metal.
  • preferred hole transport materials are N, N'-diphenyl-N, N'-bis (m-tolyl) benzidine (TPD) and N, N 'diphenyl-N, N'-di-naphth -1-yl-benzidine ( ⁇ -NPD) used.
  • the lifespan and the efficiency or its temporal course in the known electroluminescent devices do not currently meet the requirements of practice and are in need of improvement.
  • the film-forming properties of the charge transport materials used and their morphological stability within a binder layer are also unsatisfactory.
  • the inclination of a layer containing the charge transport materials mentioned in the course of the operating life of an electroluminescent device or arrangement within the crystalline layer Training centers depends to a large extent on the glass transition temperature of the materials used. In general, the higher the glass transition temperature, the lower the tendency to recrystallize at a given temperature, the rate of crystallization being extremely low below the glass transition temperature. Compounds with a high glass transition temperature can therefore be expected to have a high permissible working temperature of the arrangements produced with them.
  • a high glass transition temperature is greatly favored by the existence of space-filling, sterically demanding groups.
  • the object of the invention is to provide new compounds which are suitable as charge transport materials with glass transition temperatures in the range from 100.degree. C., preferably 150.degree. C. to 250.degree. C. and thus the working range of the electroluminescent arrangements produced with these compounds to temperature ranges from 100.degree expand to approx. 200 ° C.
  • the new triarylamine derivatives correspond to the general formula 1
  • n is an integer from 1-10; R 1 , R 2 , R 3 and R 4 , which are the same or different, are
  • aromatic or heteroaromatic units X 1 to X 4 which are the same or different, are phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl or quinolyl, and in which R 10 , R, R 12 and R 13 are the same or are different, have the meaning H, Ci to C ⁇ -alkyl, cycloalkyl, C 2 to C 4 -alkenyl, Ci to C -alkoxy, Ci to C -dialkylamino, diarylamino, halogen, hydroxy, phenyl, naphthyl or pyridyl , and wherein R 1 to R 4 are phenyl, biphenylyl, methylphenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl may be substituted by one or more substituents Ci to C 3 alkyl, Ci to C 2 alkoxy or hal
  • R 5 to R 9 which are the same or different, are H or Ci to C 15 alkyl, or R 5 and R e or R 7 and R 8 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 can be the heterocyclic elements; or Ar is a structure of formula 29, 30, 31 or 32
  • Preferred triarylamine derivatives ⁇ are those of the formula 1, in which n is an integer from 1 to 4, in particular n is 1 or 2.
  • Preferred radicals radicals R 1 to R 4 in formula 1 are phenyl, biphenylyl, methylphenyl, naphthyl, fluorenyl, triarylmethyl aryl or triarysilyl aryl.
  • Preferred radicals R 5 to R 9 which may be the same or different, have the meaning methyl or phenyl.
  • radicals R 5 and R ⁇ together with the carbon atom to which they are attached form a spiroalkane ring.
  • radicals R 20 to R 27 which may be the same or different, are hydrogen, methyl or phenyl.
  • at least one of the radicals R1 to R4 preferably represents a triarylsilyl-aryl or substituted triarylmethyl-aryl unit according to formula 4.
  • At least one of the radicals R1 to R4 preferably represents a triarylsilyl-aryl unit according to formula 4, or a triarylmethyl aryl unit according to formula 4, with the proviso that that in this case at least one of the radicals R 10 to R 13 is not equal to H, or a triarylmethyl aryl unit according to formula 4, with the proviso that in this case at least one of the radicals X 1 to X 4 is a heteroaromatic ,
  • the radicals R 10 to R 13 are preferably H, phenyl, Ci to C 3 alkyl, Ci to C3 alkoxy or halogen.
  • Methyl or phenyl are particularly preferred.
  • Halogen is preferably F or CI.
  • a preferred embodiment of the invention relates to triarylamine derivatives of the general formula
  • R 1 , R 2 , R 3 and R 4 which are the same or different, are phenyl, biphenyl, methylphenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, triphenylmethyl or triphenylsilyl, at least one of the radicals R 1 to R 4 being triphenylmethyl or triphenylsilyl of formula 4
  • R 10 , R 11 and R 12 which are the same or different, are H, d to C 6 alkyl, cycloalkyl, C 2 to C 4 alkenyl, Ci to C 4 alkoxy or halogen, and wherein R 1 to R 4 may be substituted by one or more substituents;
  • Ar is
  • R 10 to R 12 have the meaning given above.
  • the above-mentioned preferred meanings of Ar and R 1 to R 27 also apply to this embodiment.
  • the invention further relates to an organic electroluminescent device with at least one hole transport layer and one luminescent layer, at least one hole transport layer containing a triarylamine derivative according to formula 1.
  • a further embodiment of the invention consists in the organic electroluminescent device having 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 a hole transport substance or luminescent substance in an organic electroluminescent device and to the use of triarylamine derivatives according to formula 1 as a 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 can consist of an aluminum drum, there is a charge generation layer which has the task of injecting positive charge carriers into the charge transport layer when exposed to light , 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 in the areas hit by light
  • the imagewise charged (or discharged) surface is toned, the toner is optionally transferred to a material to be printed, fixed there, and finally excess toner and residual charge are removed.
  • an electroluminescent device consists 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. With an applied voltage, electrons are injected from the metal electrode (usually Ca, Mg or Al, often in conjunction with silver) due to the low work function and holes are injected into the organic layer from the counter electrode, where they recombine and form singlet excitons. After a short time they go into the basic state and emit light.
  • the metal electrode usually Ca, Mg or Al, often in conjunction with silver
  • the electroluminescent layer can now be chosen to be very thin. Due to the interchangeability of the fluorescent material regardless of its electron transport behavior, the emission wavelength can be set in a targeted manner in the entire visible spectral range.
  • the organic electroluminescent device consists of a layer structure consisting of a cathode, an electroluminescent layer which contains an organic compound and an anode, the organic compound in the hole transport layer being a triarylamine derivative of the general formula 1.
  • a preferred structure consists of the following layers: substrate - transparent anode - hole transport layer - electroluminescent layer - electron transport layer - cathode.
  • the cathode which can consist of Al, Mg, In, Ag or alloys of these metals, has a thickness between 100 and 5000 ⁇ .
  • the transparent anode can consist of indium tin oxide (ITO) with a thickness of 1000-3000 ⁇ , an indium antimine tin oxide coating or a semitransparent gold layer, which is located on a glass substrate.
  • ITO indium tin oxide
  • luminescent substance contains as usual luminescent substance, optionally contains further fluorescent substances such as.
  • it can also contain exclusively luminescent compounds according to the invention or mixtures thereof with known luminescent substances.
  • Typical examples of triarylamine derivatives according to general formula 1 are: Typical examples of triarylamine derivatives according to general formula 1 are:
  • Tables 1 and 2 below show preferred embodiments for the structural units Ar and the radicals R x (R 1 to R 4 ) according to formula 1.
  • the new compounds are synthesized by methods known per se, e.g. B. after the Ullmann synthesis or by noble metal catalytic reactions, starting from suitable primary and secondary amines and (corresponding to formulas 2 and 3) dihalobiphenyls, dihalodibenzofurans, dihalodibenzothiophenes, dihalocarbazoles and dihalo- dibenzosilols, or starting from suitable tertiary halobiphenyl-4-yl-amines and (corresponding to formulas 2 and 3) hetero-analogous benzide derivatives.
  • Ullmann synthesis is understood to mean a condensation reaction in which aryl halides, preferably aryl iodides, react at temperatures of 100-300 ° C. with the catalytic use of Cu or Cu bronze with suitable substrates to give C or N arylation products, with functionally substituted ones as well
  • aryl halides preferably aryl iodides
  • At least one layer contains triarylamine derivatives according to formula 1, preferably one or more compounds 6-24.
  • this contains known electron transport materials, such as. B. bis ⁇ aminopheny -I.S ⁇ -oxadiazole, triazole or dithiolene derivatives.
  • hole transport materials according to formulas 6 - 24 leads to a high dark conductivity of the layers and thus to a low drive voltage of less than 6 volts, which reduces the thermal load on the device Consequence.
  • the hole transport materials used according to the invention have a high glass transition temperature of more than 150 ° C. to 250 ° C. and thus a very low tendency to recrystallize in the layer. Because of this and because of the chemical structure of these relatively large molecules, layers made of these substances with and without a binder content are very stable, which enables the use of the widespread technique of "spin coating".
  • Evaporated layers are free of structural defects and have a high transparency in the visible spectral range.
  • the properties mentioned enable the production of new organic electroluminescent devices with a high luminous efficacy (> 10,000 cd / m 2 ) and at the same time significantly improved long-term stability (> 10,000 hours).
  • the working range of these devices is in the temperature range 100 to 200 ° C, preferably 120-200 ° C, in particular 120 to 150 ° C.
  • Example 1 Preparation of N, N'-bis (4 '- (N-phhenylmethyl) phenyl) -N-naphth-1-yl -amino) -biphenylyl) - N, N'-bisphenyl-2, 7-amino-9-phenylcarbazole (formula 23)
  • a glass apparatus consisting of a 500 ml three-necked flask equipped with a reflux condenser, magnetic stirrer, thermometer and gas inlet tube, is heated for 2 hours at 120 ° C. in order to remove the water bound to the glass walls.
  • the apparatus is charged with 160 ml of o-xylene which has been dried over Na and flushed with N 2 under nitrogen. 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, the catalyst complex forming.
  • the contents of the flask are heated to 120 ° C in an oil bath. NaBr excretion begins after approx. 30 min. The mixture is allowed to react at 120 ° C. for 3 hours. The flask contents are then diluted to twice its volume with toluene and then poured into ten times the amount of methanol while stirring. The raw product precipitates and can be filtered off. For cleaning, the raw product from dodecane is reprecipitated and then recrystallized from DMF. Finally, the product is sublimed in a maximum vacuum ( ⁇ 10 "5 torr).
  • N, N'-di- (triphenylsilylphenyl) -N, N'-diphenyl-benzidine (Formula 7)
  • 14.2 g of N.N'-diphenyl - Benzidine and 34.9 g of 4-bromophenyl triphenyl silane using 12.9 g of sodium tert-butoxide as a dehydrating base, 12.6 mg of palladium acetate and 10.4 ml of a 1% solution of tri-tert .-Butylphosphine implemented as a catalyst according to the procedure given there.
  • the purification is carried out by recrystallization from xylene with the addition of 5% silica gel and in the second stage by recrystallization from DMF. 16.5 g of pure N, N'-di- (triphenylsilylphenyl) -N, N'-diphthynylbenzidine are obtained, the glass transition temperature of which is 164 ° C., measured by means of DSC.
  • the cleaning is carried out analogously to Example 1, with a solvent mixture of dodecane / xylene 4: 1 being used in the first stage and a DMF / n-butanol mixture 1: 1 being used in the second stage.
  • 20 g of N ⁇ -methylphenyl-N- ⁇ riphenylmethyl-phenylJ-N'-phenyl-N'-napth-l-yl-p.p'-benzidine are obtained.
  • the glass transition temperature of this compound is 151 ° C.
  • Example 5 Preparation of N, N'-bis - (- 7- (N- (4-triphenylmethylphenyl) -N-phenylamino) -dibenzothiophene-2-yl) -N, N'-diphenyl-benzidine (formula 21)
  • N, N'-bis - (- 7-bromo-dibenzothiophene-2-yl) -N, N'-diphenyl-benzidine with 34.6 g of N-tritylphenyl-N -phenyl-amine implemented.
  • the compounds specified in Example 1 are used in the amounts specified therein. After a reaction time of 7 hours, the product is precipitated with methanol.
  • Electroluminescent arrangement A coating is applied in an ultra-high vacuum (10 "8 hPa) to a glass substrate coated with an indium tin oxide electrode (ITO). It consists of a 55 nm thick hole transport layer consisting of the well-known starburst compound 25 .
  • ITO indium tin oxide electrode
  • Example 6 The same layer arrangement as in Example 6 is produced, but in the emission layer the N, N'-diphenyl-N I N'-bis (4-triphenyl-methyl-phenyl) -amino-9-methyl-carbazole according to Example 2 used.

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  • Indole Compounds (AREA)

Abstract

L'invention concerne de nouveaux dérivés de triarylamines, de formule (1), composés de groupes latéraux compacts spéciaux, ainsi que l'utilisation de ces dérivés comme matériau de transport de trous dans des dispositifs électrophotographiques et électroluminescents. Dans la formule (1), n = 1-10, R1 à R4 représentent un groupe phényle, biphénylyle, méthylphényle, naphtyle, phénanthrényle, anthracényle, fluorényle, triarylméthyl-aryle ou triarylsilyl-aryle, éventuellement substitué, Ar est un pont biphénylène ou un pont fluorénylène substitué, ou Ar est un pont biphénylène, triphénylène ou tétraphénylène substitué lorsque n = 1.
EP02799037A 2002-01-28 2002-12-19 Derives de triarylamines et leur utilisation dans des dispositifs organiques electroluminescents et electrophotographiques Withdrawn EP1470100A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10203328 2002-01-28
DE10203328A DE10203328A1 (de) 2002-01-28 2002-01-28 Neue Triarylamin-Derivate mit raumfüllenden Flügelgruppen und ihre Einsatz in elektro-fotografischen und organischen elektrolumineszenten Vorrichtungen
PCT/DE2002/004758 WO2003064373A1 (fr) 2002-01-28 2002-12-19 Derives de triarylamines et leur utilisation dans des dispositifs organiques electroluminescents et electrophotographiques

Publications (1)

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EP1470100A1 true EP1470100A1 (fr) 2004-10-27

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EP02799037A Withdrawn EP1470100A1 (fr) 2002-01-28 2002-12-19 Derives de triarylamines et leur utilisation dans des dispositifs organiques electroluminescents et electrophotographiques

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US (1) US20050067951A1 (fr)
EP (1) EP1470100A1 (fr)
JP (1) JP2005516059A (fr)
KR (1) KR100938524B1 (fr)
CN (1) CN1602293A (fr)
DE (1) DE10203328A1 (fr)
TW (1) TWI325440B (fr)
WO (1) WO2003064373A1 (fr)

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KR100938524B1 (ko) 2010-01-25
KR20040086249A (ko) 2004-10-08
DE10203328A1 (de) 2003-08-07
WO2003064373A1 (fr) 2003-08-07
JP2005516059A (ja) 2005-06-02
US20050067951A1 (en) 2005-03-31
TW200302263A (en) 2003-08-01
CN1602293A (zh) 2005-03-30

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