WO2006011879A1 - Procede de formation d'un compose amine aromatique - Google Patents

Procede de formation d'un compose amine aromatique Download PDF

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WO2006011879A1
WO2006011879A1 PCT/US2004/021137 US2004021137W WO2006011879A1 WO 2006011879 A1 WO2006011879 A1 WO 2006011879A1 US 2004021137 W US2004021137 W US 2004021137W WO 2006011879 A1 WO2006011879 A1 WO 2006011879A1
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process according
aromatic
amine
mixture
compound
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PCT/US2004/021137
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English (en)
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Lynda Woedy Mc Garry
Paul Patrick Spara
Ruizheng Wang
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Eastman Kodak Company
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Publication of WO2006011879A1 publication Critical patent/WO2006011879A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings

Definitions

  • This invention relates to the field of organic syntheses and to a process for forming a secondary or tertiary aromatic amine compound using a palladium/phosphine catalyst.
  • Aromatic amine compounds are very useful materials and consequently there is a continuing need for improved synthetic methods that allow their preparation in an economical manner and in high purity.
  • tertiary aromatic amine compounds have found use in electroluminescent (EL) devices such as organic light-emitting diodes (OLEDs).
  • EL electroluminescent
  • OLEDs organic light-emitting diodes
  • an organic EL device is comprised of an anode for hole injection, a cathode for electron injection, and an organic medium sandwiched between these electrodes to support charge recombination that yields emission of light. These devices are also commonly referred to as organic light- emitting diodes, or OLEDs. Representative of earlier organic EL devices are Gurnee et al. US 3,172,862, issued Mar. 9, 1965; Gurnee US 3,173,050, issued Mar.
  • organic EL devices include an organic EL element consisting of extremely thin layers (e.g., less than 1.0 ⁇ m) between the anode and the cathode.
  • organic EL element encompasses the layers between the anode and cathode. Reducing the thickness lowered the resistance of the organic layer and has enabled devices that operate at much lower voltage, hi a basic two-layer EL device structure, described first in US 4,356,429, one organic layer of the EL element adjacent to the anode is specifically chosen to transport holes, and therefore, it is referred to as the hole-transporting layer, and the other organic layer is specifically chosen to transport electrons, and is referred to as the electron-transporting layer. Recombination of the injected holes and electrons within the organic EL element results in efficient electroluminescence.
  • the hole-transporting layer of the organic EL device contains at least one hole-transporting compound such as an aromatic tertiary amine, where the latter is understood to be a compound containing at least one trivalent nitrogen atom that is bonded only to carbon atoms, at least one of which is a member of an aromatic ring, hi one form the aromatic tertiary amine can be an arylamine, such as a monoarylamine, diarylamine, triarylamine, or a polymeric arylamine. Exemplary monomelic triarylamines are illustrated by Klupfel et al. US 3,180,730.
  • Suitable triarylamines substituted with one or more vinyl radicals and/or comprising at least one active hydrogen containing group are disclosed by Brantley et al US 3,567,450 and US 3,658,520.
  • a more desirable class of aromatic tertiary amines include at least two aromatic tertiary amine moieties as described in US 4,720,432 and US 5,061,569.
  • US 5,061,569, US 6,074,734, and US 6,242,1 15 describe the use tertiary amines such as tetrarylbenzidine derivatives as hole-transporting materials. These materials can also be used in light-emitting layers as host materials or in combination with other host materials, for example, see WO 02/20693. It is desirable to use very pure materials in EL devices to ensure long operating lifetimes.
  • Suitable tertiary amine derivatives can be synthesized by various methods including the Ullmann condensation which involves the coupling of aryl halides with copper, for example see J. March, Advanced Organic Chemistry, 3 r Ed., John Wiley and Sons, NY, 1985, page 597.
  • S. Turner and coworkers in US 4,764,625 describe a process of preparing a tertiary amine by the condensation of an amine compound and an iodoaryl compound. The reaction is carried out in the presence of potassium hydroxide, and a copper catalyst at a temperature between 120 0 C to about 190 0 C, however these are harsh conditions and can cause substantial decomposition of sensitive compounds.
  • the invention process is summarized above.
  • the process is useful to provide aromatic secondary and tertiary amines.
  • the process is especially useful to provide tertiary aromatic amines and in particular polycyclic aromatic molecules that contain at least two tertiary aromatic amine groups.
  • the process is valuable for producing materials that can be used in electronic devices such as EL devices.
  • the process for forming a new aromatic amine comprises starting with an initial aromatic primary or secondary amine, examples include N- phenylamine, N, N-diphenylamine, N, N-di(2-naphthyl)amine, N-(2-naphthyl)-N- (l-naphthyl)amine.
  • Amines of this type can be often purchased from commercial sources, such as Aldrich Chemical Co., or made by literature procedures, hi one preferred embodiment the starting aromatic amine is a secondary amine represented by Formula (1).
  • Ar 1 and Ar 2 represent independently selected aromatic groups.
  • Ar 1 and Ar 2 represent independently selected aryl groups, for example, phenyl groups, naphthyl groups or pyridyl groups.
  • the starting primary or secondary amine compound is mixed with an aromatic halide compound.
  • the aromatic halide compound is an arylhalide wherein the halide is an iodo, bromo, or chloro substituent.
  • Illustrative examples include a bromophenyl group, a iodophenyl group, a 1-bromonaphthyl group, a 2-iodonaphthyl group, and a 4-chloro-l,l- biphenyl group.
  • the arylhalide is an iodo or bromo compound.
  • the starting amine is a primary amine then using approximately 1 equivalent of the halide compound can form a secondary amine.
  • the halide compound be in the range of about 0.9 to 1.1 mole equivalents to that of the amount of the primary amine.
  • the starting amine is a primary amine then using approximately 2 equivalents or more of the halide compound can form a tertiary amine.
  • the halide compound may be present at 1.8, 2.0, 2.2, 3, or even greater mole equivalents relative to the amine compound. If the starting amine is a secondary amine then using approximately
  • 1 equivalent or more of the halide compound can form a tertiary amine.
  • the arylhalide be present in the range of about equal or greater than that of the amount of the secondary amine.
  • the arylhalide may be 1.5, 2.0, 2.2, 3, or even greater mole equivalents relative to the amine compound.
  • the amount of the halide compound can be adjusted accordingly.
  • a halide compound that includes two iodo, bromo, or chloro groups may be reacted with approximately two equivalents of a secondary amine to form a compound that has two tertiary amine substituents.
  • the halide compound has at least two halogen substituents.
  • the halide compound may be represented by Formula (2).
  • Xj and X 2 independently represent an iodo, bromo, or chloro substituent. In one suitable embodiment, Xj and X 2 independently represent an iodo or a bromo substituent.
  • Ar represents a divalent aromatic group, for example, a group such as a phenylene group, a biphenylene group, and a naphthylene group.
  • the reaction mixture also includes a palladium complex as a catalyst.
  • the palladium catalyst may be derived from a convenient palladium source, for example, palladium halides, including PdCl 2 , PdBr 2 , palladium carboxylates, including Pd(OAc) 2 , Pd(CF 3 CO 2 ) 2 and palladium (II) acetylacetonoate, palladium (II) bis(benzonitrile)dichloride, and tris(dibenzylideneacetone)dipalladium (0).
  • palladium halides including PdCl 2 , PdBr 2
  • palladium carboxylates including Pd(OAc) 2 , Pd(CF 3 CO 2 ) 2 and palladium (II) acetylacetonoate
  • palladium (II) bis(benzonitrile)dichloride palladium (II) bis(benzonitrile)dichloride, and
  • the quantity of palladium used in the process is typically in the range 0.0001 to 10 mole %, more commonly 0.005 to 5 mole %, and often 0.01 to 3 mole %, relative to the quantity of amine compound.
  • a phosphine compound is also present in the process.
  • Suitable phosphines can be obtained from commercial sources such as Aldrich Chemical Company or synthesized by methods know in the literature. Phosphines are believed to act as ligands to the palladium thereby forming a more effective catalyst for the coupling reaction, hi one embodiment, suitable phosphines are substituted by three groups.
  • the groups may be aromatic groups or nonaromatic groups or combinations thereof.
  • the groups include aryl groups such as phenyl groups.
  • Desirably the groups may include alkyl groups such as /-butyl groups or cycloalkyl groups.
  • phosphines examples include triphenylphosphine, tricyclohexylphosphine and tri-t-butylphosphine.
  • Suitable phosphine compounds may comprise more than one phosphine group.
  • the phosphine compound may comprise a salt, for example tri(t-butyl)phosphonium fluoroborate.
  • the quantity of phosphine ligand used in the process may be such that the molar ratio of palladium to phosphorus is from 6 to 0.1, more typically form 5.0 to 0.5 and commonly from 5.0 to 3.0.
  • the reaction is carried out in a solvent.
  • a suitable solvent is one that dissolves the reactants, at least partially, and does not interfere with the reaction.
  • aromatic solvents such as toluene and xylene are useful.
  • reaction mixture is stirred during the reaction process in order to ensure good mixing of the reactants.
  • the mixture formed by combining an aromatic primary or secondary amine with an aromatic halide compound in the presence of a palladium complex and a phosphine compound catalyst is then heated to a first temperature of at least 60°C. In one embodiment the mixture is heated to at least 60°C but to less than 85°C.
  • the base material may be an organic base, such as Na(t-BuO) or K(t-BuO).
  • the base material may be selected from alkali metal and alkaline earth metal phosphates such as Na 3 PO 4 and K 3 PO 4 , and CsCO 3 .
  • the base is Na(t-BuO).
  • the base material may be dissolved in a solvent prior to addition such as an aromatic hydrocarbon, such as toluene, or other solvent such as tetrahydrofuran.
  • the base material is added over a period of at least 5 minutes, commonly over a period of at least 15 minutes, and typically over a period of at least 25 minutes depending on the scale of the reaction.
  • the quantity of base used in the process may be such that the ratio of equivalents of base to the amine derivative is from 3 to 0.1 , more typically from 1.5 to 0.5 and commonly from 1.3 to 0.7.
  • the temperature of the mixture is maintained at or above the first temperature for a period of time to form a substantial amount an amine product.
  • the reaction is maintained at a temperature of between 65 0 C and 95 0 C and commonly between 75 0 C and 85 0 C.
  • Optimum reaction times can be determined by monitoring the reaction. For example, by removing aliquots of the reaction mixture periodically and by using thin-layer-chromatography (TLC) or high-performance-liquid chromatography (HPLC) analysis one can determine the amount of reactants present, e.g. unreacted starting amine, and one can determine the amount of product formed. In this manner the progress of the reaction can be monitored.
  • TLC thin-layer-chromatography
  • HPLC high-performance-liquid chromatography
  • the reaction times are 1 to 24 h, but maybe shorter or longer.
  • the optimum amount of the reactants relative to the initial amine compound as well as the optimum reaction conditions can be determined by doing designed experiments to maximize yield and minimize side-products.
  • the concentration of the reactants, the temperature of the reaction, and the time of the reaction can all be varied to determine preferred values, for example see D. C. Montgomery, Design And Analysis Of Experiments, 5th ed, John Wiley, New York, (2001).
  • the product amine can be isolated and purified if necessary. Purification maybe done by well-known methods such as sublimation, distillation, crystallization or column chromatography.
  • the product amine is an aromatic secondary or tertiary amine.
  • the product aromatic amine is a tertiary amine.
  • a desirable class of aromatic tertiary amines are those that include at least two aromatic tertiary amine moieties as described in US 4,720,432 and US 5,061 ,569. Such compounds include those represented by structural formula (A).
  • Qi and Q 2 are independently selected aromatic tertiary amine moieties and G is a linking group such as an arylene, cycloalkylene, or alkylene group of a carbon to carbon bond.
  • G is a linking group such as an arylene, cycloalkylene, or alkylene group of a carbon to carbon bond.
  • at least one Of Q 1 or Q 2 contains a polycyclic fused ring structure, e.g., a naphthalene.
  • G is an aryl group, it is conveniently a phenyl ene, biphenylene, or naphthalene moiety.
  • a useful class of triarylamines satisfying structural formula (A) and containing two triarylamine moieties is represented by structural formula (B):
  • R4 where R 1 and R 2 each independently represents a hydrogen atom, an aryl group, or an alkyl group or R 1 and R 2 together represent the atoms completing a cycloalkyl group; and R 3 and R 4 each independently represents an aryl group, which is in turn substituted with a diaryl substituted amino group, as indicated by structural formula (C), wherein R 5 and R 6 are independently selected aryl groups.
  • R 5 or R 6 contains a polycyclic fused ring structure, e.g., a naphthalene.
  • tetraaryldiamines Another class of useful aromatic tertiary amines is the tetraaryldiamines. Desirable tetraaryldiamines include two diarylamino groups, such as indicated by formula (C), linked through an arylene group. Useful tetraaryldiamines include those represented by formula (D). R 7. . Rs
  • each Are is an independently selected arylene group, such as a phenylene or anthracene moiety
  • n is an integer of from 1 to 4
  • Ar, R 7 , R 8 , and R 9 are independently selected aryl groups.
  • at least one of Ar, R 7 , R 8 , and R 9 is a polycyclic fused ring structure, e.g., a naphthalene.
  • the various alkyl, alkylene, aryl, and arylene moieties of the foregoing structural formulae (A), (B), (C), (D), can each in turn be substituted.
  • Typical substituents include alkyl groups, alkoxy groups, aryl groups, aryloxy groups, and halide such as fluoride, chloride, and bromide.
  • the various alkyl and alkylene moieties typically contain from about 1 to 6 carbon atoms.
  • the cycloalkyl moieties can contain from 3 to about 10 carbon atoms, but typically contain five, six, or seven ring carbon atoms ⁇ e.g., cyclopentyl, cyclohexyl, and cycloheptyl ring structures.
  • the aryl and arylene moieties are usually phenyl and phenylene moieties.
  • the product aromatic amine is represented by Formula (3).
  • Ar 1 and Ar 2 may be the same or different and each represents an independently selected aromatic group, such as a phenyl group or a naphthyl group.
  • Each d independently represents an independently selected substituent such as a methyl group or a phenyl group.
  • Each n independently is 0-4.
  • substituted or “substituent” means any group or atom other than hydrogen.
  • group when the term “group” is used, it means that when a substituent group contains a substitutable hydrogen, it is also intended to encompass not only the substituent's unsubstituted form, but also its form further substituted with any substituent group or groups as herein mentioned, so long as the substituent does not destroy properties necessary for device utility.
  • a substituent group may be halogen or may be bonded to the remainder of the molecule by an atom of carbon, silicon, oxygen, nitrogen, phosphorous, sulfur, selenium, or boron.
  • the substituent maybe, for example, halogen, such as chloro, bromo or fluoro; nitro; hydroxyl; cyano; carboxyl; or groups which may be further substituted, such as alkyl, including straight or branched chain or cyclic alkyl, such as methyl, trifluoromethyl, ethyl, t-butyl, 3-(2,4-di-t-pentylphenoxy) propyl, and tetradecyl; alkenyl, such as ethylene, 2-butene; alkoxy, such as methoxy, ethoxy, propoxy, butoxy, 2-methoxyethoxy, sec-butoxy, hexyloxy, 2-ethylhexyloxy, tetradecyloxy, 2-(2,4-di-t-pentylphenoxy)ethoxy, and 2-dodecyloxyethoxy; aryl such as phenyl, 4-t-butylphenyl,
  • the substituents may themselves be further substituted one or more times with the described substituent groups.
  • the particular substituents used may be selected by those skilled in the art to attain the desired desirable properties for a specific application and can include, for example, electron-withdrawing groups, electron-donating groups, and steric groups.
  • the substituents may be joined together to form a ring such as a fused ring unless otherwise provided.
  • the above groups and substituents thereof may include those having up to 48 carbon atoms, typically 1 to 36 carbon atoms and usually less than 24 carbon atoms, but greater numbers are possible depending on the particular substituents selected.
  • Example 1 Inventive Large Scale Preparation of 4,4'-Bis[N-(l-naphthyl)-N-(2- naphthyl)amino]biphenyl (AA-I).
  • N-l- ⁇ aphthyl-N-2-naphthylamine (12.7 kg, 47.14 mol), 4,4'- diiodobiphenyl (9.8 Kg, 24.2 mol), palladium (II) acetate (0.150 Kg, 0.663 mol), and toluene (140 Kg) were combined in a vessel. Nitrogen was bubbled through the mixture for 30 min to remove oxygen. The catalyst, tri-f-butylphosphine (0.6 Kg, 3.0 mol) was added as a 20 % by weight solution in toluene with stirring and the mixture was heated to 75°C over a 1 h period.
  • the filtrate was distilled to 1/10 volume and methanol was added. After cooling to 10°C, the product was allowed to crystallize for 12 hours and collected. The crude product was dissolved in hot cyclohexane, treated with silica gel, and stirred for 16 h at 70 0 C and then filtered. The filtrate was distilled to 1/10 volume and methanol was added. After cooling to 10 0 C, the product was allowed to crystallize for 12 hours and collected. The product was then slurried in isopropyl alcohol. The isopropyl alcohol was distilled and replenished with fresh isopropyl alcohol. This procedure was repeated seven times. Then methanol was added, and the methanol was removed by distillation and replenished with fresh methanol.
  • Example 2 Inventive Small-Scale Preparation of AA-I.
  • N-(l-Naphthyl)-N-(2-naphthyl)amine 64.08 g, 0.238 mol
  • 4,4'- diiodobiphenyl 48.28g, 0.118 mol
  • 0.8 g 2.4 mmol
  • the solution was put under vacuum, and then flushed with nitrogen to ensure that all oxygen was removed. This was repeated twice.
  • N-(l-Naphthyl)-N-(2-naphthyl)amine 40.41 g, 0.15 mol
  • 4,4'- diiodobiphenyl 31.5g, 0.078 mol
  • a solution of nitrogen-purged 20 % by weight sodium t- butoxide (90.0 g, 0.187 mol) in THF was added quickly to the reaction mixture. The solution was put under vacuum and then flushed with nitrogen to ensure that all oxygen was removed. This was repeated twice.
  • Table 1 shows the LC data measured for samples 1-1 and C-I .
  • the number of impurities corresponds to the number of peaks in the chromatograph that are not due to the desired product.
  • the level of the impurities corresponds to the sum of the area under all the impurity peaks divided by the area under all the peaks including the product peak multiplied by 100.
  • the yield of the product, AA-I was determined in a similar manner. It can be seen from Table 1 that the N,N,N'N'-tetraarylamine, AA-I, prepared according to the inventive process is formed in higher yield and greater purity than when synthesized by the comparative process.
  • Embodiment of this invention may provide amines of high purity and yield.
  • the aromatic amine compounds synthesized according to this invention maybe incorporated in an EL device. In one embodiment the aromatic amine materials are included in a hole-transporting layer of an EL device.

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Abstract

L'invention concerne un procédé de formation d'un produit d'amine aromatique. Ce procédé consiste : (a) à combiner une amine initiale primaire ou secondaire aromatique à un composé halogénure aromatique en présence d'un complexe palladium et d'un catalyseur de composé phosphine afin d'obtenir un mélange ; (b) à chauffer ce mélange à une première température d'au moins 60 °C ; (c) à ajouter un matériau de base au mélange chauffé ; et (d) à maintenir la température du mélange à la première température ou à une température supérieure, pendant une durée suffisante pour produire une forme substituée aromatique de l'amine initiale primaire ou secondaire aromatique. Le procédé selon l'invention permet d'obtenir des produits de haute pureté, avec un bon rendement.
PCT/US2004/021137 2004-06-30 2004-06-30 Procede de formation d'un compose amine aromatique WO2006011879A1 (fr)

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
JP2009062362A (ja) * 2007-07-24 2009-03-26 Samsung Electronics Co Ltd 芳香族化合物およびこれを含む有機膜を備えた有機発光素子並びにその製造方法
US9331285B2 (en) 2009-12-16 2016-05-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using same
US10263191B2 (en) 2009-04-24 2019-04-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US10297765B2 (en) 2007-12-28 2019-05-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using the same

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JP2009062362A (ja) * 2007-07-24 2009-03-26 Samsung Electronics Co Ltd 芳香族化合物およびこれを含む有機膜を備えた有機発光素子並びにその製造方法
KR101453872B1 (ko) 2007-07-24 2014-10-23 삼성디스플레이 주식회사 방향족 화합물 및 이를 포함한 유기막을 구비한 유기 발광소자
US10297765B2 (en) 2007-12-28 2019-05-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using the same
US11133478B2 (en) 2007-12-28 2021-09-28 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent device using the same
US10263191B2 (en) 2009-04-24 2019-04-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US10686137B2 (en) 2009-04-24 2020-06-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US11024806B2 (en) 2009-04-24 2021-06-01 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US9331285B2 (en) 2009-12-16 2016-05-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescent element using same
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