COMPOSITION FOR ORGANIC ELECTRONIC DEVICES

Abstract

The invention relates to a composition comprising an electron-transporting host and a hole-transporting host, to the use thereof in electronic devices and to electronic devices containing said composition. The electron-transporting host is most preferably selected from the class of triazine-dibenzofurane-fluorenyl systems or from the class of triazine-dibenzothiophene-fluorenyl systems. The hole-transporting host is preferably selected from the class of biscarbazoles.

Claims

1.-19. (canceled)

20. A composition comprising at least one compound of the formula (1) and at least one compound of the formula (2) ##STR03052## where the symbols and indices used are as follows: X is the same or different at each instance and is CR.sup.0 or N, with the proviso that at least two X groups are N; Y is selected from O and S; F is the same or different at each instance and is a single bond or an aromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted by one or more R.sup.5 radicals; R.sub.A is H, —F.sub.3—Ar.sub.4 or —F.sub.1—N(Ar).sub.2; R.sub.B is Ar.sub.3 or -L.sub.2-N(Ar).sub.2; L.sub.1, L.sub.2 are the same or different at each instance and are a single bond or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals; L.sub.3 is a single bond or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, where one substituent R.sup.1 on the carbazole may form a ring with a substituent R.sup.3; Ar.sub.1, Ar.sub.2 at each instance are each independently an aryl or heteroaryl group having 5 to 40 aromatic ring atoms which may be substituted by one or more R.sup.3 radicals; Ar.sub.3 is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 10 to 40 aromatic ring atoms, which may be substituted by one or more R.sup.3 radicals; Ar.sub.4 is the same or different at each instance and is an unsubstituted or substituted 9-arylcarbazolyl or unsubstituted or substituted carbazol-9-yl, which may be substituted by one or more R.sup.4 radicals, and where one or more instances each of two R.sup.4 radicals or one R.sup.4 radical together with one R.sup.1 radical may independently form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring, where aryl is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by R.sup.3; R* is the same or different at each instance and is a straight-chain alkyl group having 1 to carbon atoms or an aryl group having 6 to 12 carbon atoms, where two substituents R* together may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more substituents R.sup.5; R.sup.0, R, R.sup.1 are the same or different at each instance and are selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.2).sub.2, C(═O)Ar, C(═O)R.sup.2, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, Si(Ar).sub.3, Si(R.sup.2).sub.3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.2C═CR.sup.2, Si(R.sup.2).sub.2, C═O, C═S, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; at the same time, it is optionally possible for two substituents R.sup.0 and/or R and/or R.sup.1 bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sup.2 radicals; R.sup.2 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, NH.sub.2, N(R.sup.3).sub.2, C(═O)Ar, C(═O)H, C(═O)R.sup.3, P(═O)(Ar).sub.2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by HC═CH, R.sup.3C═CR.sup.3, C═C, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, P(═O)(R.sup.3), SO, SO.sub.2, NH, NR.sup.3, O, S, CONH or CONR.sup.3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; where it is optionally possible for two or more adjacent substituents R.sup.2 to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sup.3 radicals; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, N(Ar).sub.2, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, it is possible for two or more adjacent R.sup.3 substituents together to form a mono- or polycyclic, aliphatic ring system; R.sup.4 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, a straight-chain or branched alkyl group having 1 to 4 carbon atoms or CN; at the same time, two or more adjacent R.sup.4 substituents together may form a mono- or polycyclic ring system; R.sup.5 is the same or different at each instance and is selected from the group consisting of D, F, CN and an aryl group having 6 to 18 carbon atoms; at the same time, two or more adjacent substituents R.sup.5 together may form a mono- or polycyclic, aliphatic ring system; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R.sup.3 radicals; at the same time, two Ar radicals bonded to the same nitrogen atom, phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R.sup.3), C(R.sup.3).sub.2, O and S, and n and m at each instance are independently 0, 1, 2 or 3, o at each instance is independently 0, 1, 2, 3, 4, 5, 6 or 7; q at each instance is independently 0, 1, 2 or 3; p at each instance is independently 0, 1, 2, 3 or 4.

21. The composition as claimed in claim 20, wherein Y in formula (1) is O.

22. The composition as claimed in claim 20, wherein the compound of the formula (2) conforms to one of the formulae (2a) to (2d) ##STR03053## where the symbols and indices L.sub.1, L.sub.2, L.sub.3, Ar, Ar.sub.3, Ar.sub.4, R.sup.1, q and p used are as defined in claim 20.

23. The composition as claimed in claim 20, wherein the composition further comprises at least one compound selected from the group consisting of hole injection materials, hole transport materials, hole blocker materials, wide band gap materials, fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron blocker materials, electron transport materials and electron injection materials, n-dopants and p-dopants.

24. The composition as claimed in claim 20, wherein the composition consists of a compound of the formula (1) and a compound of the formula (2).

25. A formulation comprising the composition as claimed in claim 20 and at least one solvent.

26. An organic electronic device comprising the composition as claimed in claim 20.

27. The device as claimed in claim 26, wherein the organic electronic device is selected from the group of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors.

28. An organic electronic device comprising at least one composition as claimed in claim 20 in at least one organic layer.

29. The device as claimed in claim 28, wherein the device is selected from the group of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors.

30. The device as claimed in claim 28, wherein the device is an electroluminescent device selected from organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).

31. An organic electronic device which comprises the composition as claimed in claim 20 in an emission layer (EML), in an electron transport layer (ETL), in an electron injection layer (EIL) and/or in a hole blocker layer (HBL).

32. An organic electronic device which comprises the composition as claimed in claim 20 in the emission layer together with a phosphorescent emitter.

33. A process for producing an organic electronic device, which comprises applying at least one organic layer comprising the composition as claimed in claim 20 by gas phase deposition or from solution.

34. The process as claimed in claim 33, wherein the at least one compound of the formula (1) and the at least one compound of the formula (2) are deposited from the gas phase successively or simultaneously from at least two material sources, optionally together with further materials, and form the organic layer.

35. A process for producing an organic electronic device, which comprises applying at least one organic layer comprising the composition as claimed in claim 24 by gas phase deposition or from solution and is utilized as a material source for gas phase deposition of the host system and forms the organic layer optionally together with further materials.

36. A process for producing an organic electronic device, which comprises applying at least one organic layer comprising the formulation as claimed in claim 25 is used in order to apply the organic layer.

37. A compound of the formula (1a) ##STR03054## where the symbols and indices used are as follows: Y is selected from O and S; L is the same or different at each instance and is an aromatic ring system having 6 to 18 carbon atoms, which may be substituted by one or more R.sup.5 radicals; Ar.sub.1, Ar.sub.2 at each instance are each independently an aryl or heteroaryl group having 5 to 40 aromatic ring atoms which may be substituted by one or more R.sup.3 radicals; R* is the same or different at each instance and is a straight-chain alkyl group having 1 to carbon atoms or an aryl group having 6 to 12 carbon atoms, where two substituents R* together may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R radicals; R is the same or different at each instance and is selected from the group consisting of D, F, CN and an aryl group having 6 to 10 carbon atoms. R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, N(Ar).sub.2, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, it is possible for two or more adjacent R.sup.3 substituents together to form a mono- or polycyclic, aliphatic ring system; R.sup.5 is the same or different at each instance and is selected from the group consisting of D, F, CN and an aryl group having 6 to 18 carbon atoms; at the same time, two or more adjacent substituents R.sup.5 together may form a mono- or polycyclic, aliphatic ring system; n and m at each instance are independently 0, 1, 2 or 3 and o at each instance is independently 0, 1, 2, 3, 4, 5, 6 or 7.

38. The compound as claimed in claim 37, wherein L is the same or different at each instance and is phenylene, biphenylene, naphthylene, phenanthrenylene or triphenylenylene, which may be substituted by one or more R.sup.5 radicals.

39. The compound as claimed in claim 37, wherein the compound is selected from the group of compounds ##STR03055## ##STR03056## ##STR03057## ##STR03058## ##STR03059## ##STR03060## ##STR03061## ##STR03062## ##STR03063##

Description

EXAMPLE 1: PRODUCTION OF THE OLEDS

[0261] Examples C1 to I10 which follow (see table 8) present the use of the material combinations of the invention in OLEDs.

[0262] Pretreatment for examples C1 to I10: Glass plaques coated with structured ITO (indium tin oxide) of thickness 50 nm are treated prior to coating, first with an oxygen plasma, followed by an argon plasma. These plasma-treated glass plaques form the substrates to which the OLEDs are applied.

[0263] The OLEDs basically have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL)/electron blocker layer (EBL)/emission layer (EML)/optional hole blocker layer (HBL)/electron transport layer (ETL)/optional electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminum layer of thickness 100 nm. The exact structure of the OLEDs can be found in table 8. The materials required for production of the OLEDs are shown in table 9. The data of the OLEDs are listed in table 10. Examples C1-C8 are comparative examples according to the prior art; examples I1 to I10 show data of OLEDs of the invention.

[0264] All materials are applied by thermal vapor deposition in a vacuum chamber. In this case, the emission layer always consists of at least one matrix material (host material), for the purposes of the invention at least two matrix materials, and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by co-evaporation. Details given in such a form as SoA1:CoH1:TEG1 (45%:45%:10%) mean here that the material SoA1 is present in the layer in a proportion by volume of 45%, CoH1 in a proportion of 45% and TEG1 in a proportion of 10%.

[0265] Analogously, the electron transport layer may also consist of a mixture of two materials.

[0266] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra and the current efficiency (CE, measured in cd/A) as a function of luminance, calculated from current-voltage-luminance characteristics assuming Lambertian emission characteristics, and the lifetime are measured. The electroluminescence spectra are determined at a current density of 10 mA/cm.sup.2, and the CIE 1931 x and y color coordinates are calculated therefrom. The parameter U10 in table 10 refers to the voltage which is required for a current density of 10 mA/cm.sup.2. CE10 refers to the current efficiency attained at a current density of 10 mA/cm.sup.2.

[0267] The lifetime LT is defined as the time after which the luminance drops from the starting luminance to a certain proportion L1 in the course of operation with constant current density j.sub.0. A figure of L1=80% in table 10 means that the lifetime reported in the LT column corresponds to the time after which the luminance falls to 80% of its starting value.

[0268] Use of Mixtures of the Invention in OLEDs

[0269] The material combinations of the invention can be used in the emission layer in phosphorescent green OLEDs. The inventive combinations of compounds 1 and 6 with compound 15, 19, 23, 26 or 27 are used in examples 11 to 110 as matrix material in the emission layer.

TABLE-US-00012 TABLE 8 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex. thickness thickness thickness thickness thickness thickness thickness C1 HATCN SpMA1 SpMA2 SoA1:15:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1nm 30 nm 30 nm C2 HATCN SpMA1 SpMA2 SoA1:19:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm C3 HATCN SpMA1 SpMA2 SoA1:23:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm C4 HATCN SpMA1 SpMA2 SoA1:26:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1nm 30 nm 30 nm C5 HATCN SpMA1 SpMA2 SoA1:27:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm C6 HATCN SpMA1 SpMA2 SoA2:23:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm C7 HATCN SpMA1 SpMA2 SoA3:15:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm C8 HATCN SpMA1 SpMA2 SoA3:23:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I1 HATCN SpMA1 SpMA2 6:15:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I2 HATCN SpMA1 SpMA2 6:19:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I3 HATCN SpMA1 SpMA2 6:23:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I4 HATCN SpMA1 SpMA2 6:26:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I5 HATCN SpMA1 SpMA2 6:27:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I6 HATCN SpMA1 SpMA2 1:15:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I7 HATCN SpMA1 SpMA2 1:19:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I8 HATCN SpMA1 SpMA2 1:23:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I9 HATCN SpMA1 SpMA2 1:26:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I10 HATCN SpMA1 SpMA2 1:27:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm

TABLE-US-00013 TABLE 9 Structural formulae of the materials for OLEDs [02952] [02953] [02954] [02955] [02956] [02957] [02958] [02959] [02960]

TABLE-US-00014 TABLE 10 Data of the OLEDs U10 CE10 CIE x/y at j.sub.0 L1 LT Ex. (V) (cd/A) 10 mA/cm.sup.2 (mA/cm.sup.2) (%) (h) C1 4.1 59 0.33/0.63 40 80 410 C7 4.3 63 0.33/0.63 40 80 470 I1 4.1 65 0.33/0.63 40 80 560 I6 4.0 65 0.33/0.63 40 80 490 C2 4.1 58 0.33/0.63 40 80 460 I2 4.0 64 0.33/0.63 40 80 610 I7 4.0 63 0.33/0.63 40 80 550 C3 4.0 57 0.32/0.64 40 80 320 C6 4.0 62 0.33/0.63 40 80 200 C8 4.3 62 0.33/0.63 40 80 350 I3 4.0 62 0.32/0.64 40 80 400 I8 4.0 61 0.32/0.64 40 80 380 C4 3.9 60 0.32/0.63 40 80 240 I4 3.9 65 0.32/0.63 40 80 310 I9 3.9 59 0.32/0.63 40 80 270 C5 3.9 60 0.33/0.63 40 80 280 I5 3.9 64 0.33/0.63 40 80 360 I10 3.9 60 0.33/0.63 40 80 330

EXAMPLE 2: SYNTHESIS OF COMPOUNDS OF THE INVENTION

a) 2-{12-chloro-8-oxatricyclo[7.4.0.0.SUP.2,7.]trideca-1 (13),2(7),3,5,9,11-hexaen-3-yl}-4-{8-oxatricyclo[7.4.0.0.SUP.2,7.]trideca-1(9),2,4,6,10,12-hexaen-3-yl}-6-phenyl-1,3,5-triazine

[0270] ##STR02961##

[0271] 58 g (210 mmol; 1.00 eq.) of 1-boronyl-8-chlorodibenzofuran [CAS 162667-19-4], 90.2 g (252 mmol; 1.20 eq.) of 2-chloro-4-{8-oxatricyclo[7.4.0.0.sup.2,7]trideca-1(9),2(7),3,5,10,12-hexaen-3-yl}-6-phenyl-1,3,5-triazine [CAS 1883265-32-4] and 44.5 g (420 mmol, 2.00 eq.) of sodium carbonate [CAS 497-19-8] are suspended in a mixture of 1000 ml of dioxane [CAS 123-91-1], 1000 ml of toluene [CAS 108-88-3] and 400 ml of water. To this suspension is added 4.85 g (4.20 mmol; 0.02 eq.) of tetrakis(triphenylphosphine)palladium(0) [CAS 14221-01-3], and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is removed, filtered through silica gel, washed three times with 200 ml of water and then concentrated to dryness. The yield is 79.1 g (151 mmol; 72% of theory).

[0272] In an analogous manner, it is possible to obtain the following compounds;

TABLE-US-00015 No. Reactant 1 Product Yield 1a [02962] [02963] 80% 2a [02964] [02965] 65% 3a [02966] [02967] 67% 4a [02968] [02969] 75%

b) 2,4-Diphenyl-6-[12-(3-{9,9′-spirobi[fluoren]-7-yl}phenyl)-8-oxatricyclo[7.4.0.0.SUP.2,7.]trideca-1(9),2(7),3,5,10,12-hexaen-3-yl]-1,3,5-triazine

[0273] ##STR02970##

[0274] 100 g (209 mmol; 1.00 eq.) of 2□{12□bromo□8□oxatricyclo[7.4.0.0.sup.2,7]trideca□1(9),2(7),3,5, 10,12□hexaen□3□yl}□4,6□diphenyl□1,3,5□triazine [CAS 1160861-53-9], 114 g (220 mmol; 1.05 eq.) of (3□{9,9′□spirobi[fluoren]□2□yl}phenyl)boronic acid [CAS 1365812-76-5] and 133 g (627 mmol; 3.00 eq.) of tripotassium phosphate [CAS 14593-46-5] suspended in a mixture of 800 ml of dioxane [CAS 123-91-1], 800 ml of toluene [CAS 108-88-3] and 800 ml of water. To this suspension are added 3.86 g (4.80 mmol; 4.5 mol %) of dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (SPhos) [CAS 657408-07-6] and 2.87 g (3.14 mmol; 1.5 mol %) of tris(dibenzylideneacetone)dipalladium [CAS 51364-51-3], and the reaction mixture is heated under reflux for 16 h. The reaction mixture is cooled down to room temperature and phases are separated. After the aqueous phase has been extracted, the combined organic phases are washed with saline solution and dried over sodium sulfate. After filtration through alox, the solvent is removed. The resultant solid is recrystallized twice from ethyl acetate. After final sublimation under high vacuum, the purified product is obtained as a colorless solid, 96.3 g (122 mmol; 58%).

[0275] In an analogous manner, it is possible to obtain the following compounds:

TABLE-US-00016 No. Reactant 1 Reactant 2 Product Yield  1b [02971] [02972] [02973] 42%  2b [02974] [02975] [02976] 45%  3b [02977] [02978] [02979] 55%  4b [02980] [02981] [02982] 50%  5b [02983] [02984] [02985] 60%  6b [02986] [02987] [02988] 53%  7b [02989] [02990] [02991] 49%  8b [02992] [02993] [02994] 28%  9b [02995] [02996] [02997] 15% 10b [02998] [02999] [03000] 55% 11b [03001] [03002] [03003] 61% 12b [03004] [03005] [03006] 51% 13b [03007] [03008] [03009] 38% 14b [03010] [03011] [03012] 42% 15b [03013] [03014] [03015] 48% 16b [03016] [03017] [03018] 44% 17b [03019] [03020] [03021] 62% 18b [03022] [03023] [03024] 48% 19b [03025] [03026] [03027] 55% 20b [03028] [03029] [03030] 49% 21b [03031] [03032] [03033] 53% 22b [03034] [03035] [03036] 59% 23b [03037] [03038] [03039] 65% 24b [03040] [03041] [03042] 57% 25b [03043] [03044] [03045] 57% 26b [03046] [03047] [03048] 53% 27b [03049] [03050] [03051] 49%