Composition for organic electronic devices

Abstract

The present invention relates to a composition which comprises an electron-transporting host and a hole-transporting host, to the use thereof in electronic devices and to electronic devices containing this composition. The electron-transporting host is particularly preferably selected from the class of the triazine-dibenzofuran-carbazole systems or the class of the triazine-dibenzothiophene-carbazole systems. The hole-transporting host is preferably selected from the class of the biscarbazoles.

Claims

1. A composition comprising at least one compound of the formula (1) and at least one compound of the formula (2) ##STR01522## where the following applies to the symbols and indices used: X is on each occurrence, identically or differently, CR.sup.0 or N, with the proviso that at least one group X stands for N; X.sub.1 is on each occurrence, identically or differently, CR or N; X.sub.2 is on each occurrence, identically or differently, CR′ or N; Y is selected from O or S; L is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3; Ar.sub.1, Ar.sub.2 are in each case, independently of one another on each occurrence, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3; 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 radicals R.sup.3; Ar.sub.4 and Ar.sub.5 are in each case, independently of one another, 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 radicals R.sup.3, with the proviso that Ar4 and Ar.sub.5 cannot simultaneously be phenyl; R.sup.0, R, R.sup.1 are selected on each occurrence, identically or differently, 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 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, which may in each case be substituted by one or more radicals R.sup.2, where one or more non-adjacent 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 H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.2, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.2; R.sup.2 is selected on each occurrence, identically or differently, 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 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, which may in each case be substituted by one or more radicals R.sup.3, where one or more non-adjacent CH.sub.2 groups may be replaced by HC═CH, R.sup.3C═CR.sup.3, CEC, 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 H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.3, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3, or a combination of these systems, where two or more adjacent substituents R.sup.2 may option-ally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R.sup.3; R.sup.3 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H 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; two or more adjacent substituents R.sup.3 may form a mono- or polycyclic, aliphatic ring system with one another; Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R.sup.3; two radicals Ar which are bonded to the same N atom, P atom or B 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 or S, and n and m, independently of one another, denote 0, 1, 2 or 3.

2. The composition according to claim 1, wherein the compound of the formula (1) corresponds to the formula (1a), (1b), (1c) or (1d), ##STR01523## where the symbols and indices used have a meaning as in claim 1 and p and o in each case, independently of one another, denote 0, 1, 2 or 3.

3. The composition according to claim 1, wherein the compound of the formula (2) corresponds to the formula (2a), ##STR01524## where the symbols and indices used have a meaning as in claim 1, q and t in each case, independently of one another, denote 0, 1, 2, 3 or 4 and r and s in each case, independently of one another, denote 0, 1, 2 or 3.

4. The composition according to claim 1, wherein one of the substituents Ar.sub.4 or Ar.sub.5 denotes 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 radicals R.sup.3, and the other substituent denotes an aromatic ring system having 6 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3, with the proviso that Ar.sub.4 and Ar.sub.5 cannot simultaneously be phenyl.

5. The composition according to claim 1, wherein the substituents Ar.sub.4 and Ar.sub.5 in each case, independently of one another, denote an aromatic ring system having 6 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3, with the proviso that Ar.sub.4 and Ar.sub.5 are not simultaneously phenyl.

6. The composition according to claim 1, wherein the composition comprises at least one further compound selected from the group consisting of hole-injection materials, hole-transport materials, hole-blocking materials, wide bandgap materials, fluorescent emitters, phosphorescent emitters, host materials, electron-blocking materials, electron-transport materials and electron-injection materials, n-dopants and p-dopants.

7. The composition according to claim 1, wherein L is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 6 to 18 C atoms, which may be substituted by one or more radicals R.sup.3.

8. A formulation comprising the composition according to claim 1 and at least one solvent.

9. An organic electronic device containing at least one composition according to claim 1.

10. The device according to claim 9, 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.

11. The device according to claim 9, 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).

12. The device according to claim 9, wherein the device contains the composition in an emission layer (EML), in an electron-transport layer (ETL), in an electron-injection layer (EIL) and/or in a hole-blocking layer (HBL).

13. The device according to claim 9, wherein the device contains the composition in the emission layer together with a phosphorescent emitter.

14. A process for the production of a device which comprises applying at least one organic layer comprising a composition according to claim 1 by gas-phase deposition or from solution.

15. The process according to claim 14, wherein at least one compound of the formula (1) and at least one compound of the formula (2), are deposited from the gas phase successively or simultaneously from at least two material sources, optionally with further materials, and form the organic layer.

16. The process according to claim 14, wherein the composition is utilized as material source for the gas-phase deposition and forms the organic layer.

17. The process according to claim 14, which comprises utilizing a formulation comprising the composition and at least one solvent in order to apply the organic layer.

18. The composition according to claim 1, wherein L is an aromatic or heteroaromatic ring system having 6 to 18 C atoms, which may be substituted by one or more radicals R.sup.3.

Description

Example 1: Production of the OLEDs

(1) The use of the material combinations according to the invention in OLEDs is presented in Examples E1 to E10a below (see Table 16).

(2) Pretreatment for Examples E1-E10a: Glass plates coated with structured ITO (indium tin oxide) in a thickness of 50 nm are, before coating, treated firstly with an oxygen plasma, followed by an argon plasma. These plasma-treated glass plates form the substrates to which the OLEDs are applied.

(3) The OLEDs have basically the following layer structure: substrate/hole-injection layer (HIL)/hole-transport layer (HTL)/electron-blocking layer (EBL)/emission layer (EML)/optional hole-blocking layer (HBL)/electron-transport layer (ETL)/optional electron-injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer with a thickness of 100 nm. The precise structure of the OLEDs is shown in Table 16. The materials required for the production of the OLEDs are shown in Table 17.

(4) The data of the OLEDs are listed in Table 18. Example V1 is a comparative example in accordance with WO 2015/169412, Examples E1 to E10a show data of OLEDs according to the invention. Examples E5, E10 and E10a show the preferred OLEDs according to the invention.

(5) All materials are applied by thermal vapour deposition in a vacuum chamber. The emission layer here always consists of at least one matrix material (host material), in the sense of the invention at least two matrix materials, and an emitting dopant (emitter), which is admixed with the matrix material or matrix materials in a certain proportion by volume by co-evaporation. An expression such as CbzT1:BisC1:TEG1 (45%:45%:10%) here means that material CbzT1 is present in the layer in a proportion by volume of 45%, BisC1 is present in the layer in a proportion of 45% and TEG1 is present in the layer in a proportion of 10%. Analogously, the electron-transport layer may also consist of a mixture of two materials.

(6) The OLEDs are characterised by standard methods. For this purpose, the electroluminescence spectra, the current efficiency (CE, gemessen in cd/A) and the external quantum efficiency (EQE, measured in %) as a function of the luminous density, calculated from current/voltage/luminous density characteristic lines assuming Lambert emission characteristics, and the lifetime are determined. The electroluminescence spectra are determined at a luminous density of 1000 cd/m.sup.2 and the CIE 1931 x and y colour coordinates are calculated therefrom. The term U1000 in Table 18 denotes the voltage required for a luminous density of 1000 cd/m.sup.2. CE1000 and EQE1000 denote the current efficiency and external quantum efficiency respectively that are achieved at 1000 cd/m.sup.2.

(7) The lifetime LT defines the time after which the luminous density drops from the initial luminous density to a certain proportion L1 on operation at a constant current density j.sub.0. An expression L1=80% in Table 18 means that the lifetime indicated in column LT corresponds to the time after which the luminous density drops to 80% of its initial value.

(8) Use of Mixtures According to the Invention in OLEDs

(9) The material combinations according to the invention can be employed in the emission layer in phosphorescent OLEDs. The combination according to the invention of compound CbzT1, corresponding to compound 1, with BisC2 (corresponding to compound 89) or BisC3 (corresponding to compound 90) is employed in Examples E1 to E4 as matrix material in the emission layer. The combination according to the invention of compounds 9, 13 and 15 in each case with compound 91 is employed in Examples E5, E5a, E6, E7, E10 and E10a as matrix material in the emission layer. The combination according to the invention of compound 69 with compound 91 is employed in Example E8 as matrix material in the emission layer.

(10) TABLE-US-00016 TABLE 16 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex. Thickness Thickness Thickness Thickness Thickness Thickness Thickness V1 HATCN SpMA1 SpMA2 CbzT1:BisC1:TEG1 ST2 ST2:LiQ — 5 nm 230 nm 20 nm (45%:45%:10%) 30 nm 10 nm (50%:50%) 30 nm E1 HATCN SpMA1 SpMA2 CbzT1:BisC2:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (44%:44%:12%) 30 nm 10 nm (50%:50%) 30 nm E2 HATCN SpMA1 SpMA2 CbzT1:BisC3:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (44%:44%:12%) 30 nm 10 nm (50%:50%) 30 nm E3 HATCN SpMA1 SpMA2 CbzT1:BisC2:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm (50%:50%) 30 nm E4 HATCN SpMA1 SpMA2 CbzT1:BisC3:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm (50%:50%) 30 nm E5 HATCN SpMA1 SpMA2 9:91:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (23%:70%:7%) 30 nm 10 nm (50%:50%) 30 nm E5a HATCN SpMA1 SpMA2 9:91:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm (50%:50%) 30 nm E6 HATCN SpMA1 SpMA2 13:91:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm (50%:50%) 30 nm E7 HATCN SpMA1 SpMA2 16:91:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm (50%:50%) 30 nm E8 HATCN SpMA1 SpMA2 69:91:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm (50%:50%) 30 nm E9 HATCN SpMA1 SpMA2 CbzT1:91:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (46%:47%:7%) 30 nm 10 nm (50%:50%) 30 nm E10 HATCN SpMA1 SpMA2 9:91:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (44%:44%:12%) 30 nm 10 nm (50%:50%) 30 nm E10a HATCN SpMA1 SpMA2 9:91:TEG1 ST2 ST2:LiQ LiQ 1 nm 5 nm 230 nm 20 nm (22%:63%:12%) 30 nm 10 nm (50%:50%) 30 nm

(11) TABLE-US-00017 TABLE 17 Structural formulae of the materials for OLEDs HATCN SpMA1 SpMA2 ST2 TEG1 LiQ CbzT1 BisC1 BisC2 0 BisC3 SpMA3 9 13 16 69 91

(12) TABLE-US-00018 TABLE 18 Data of the OLEDs U1000 CE1000 EQE 1000 CIE x/y at j.sub.0 L1 LT Ex. (V) (cd/A) (%) 1000 cd/m.sup.2 (mA/cm.sup.2) (%) (h) V1 3.5 70 18.4 0.33/0.63 20 80 370 E1 3.2 67 18.0 0.33/0.63 20 80 930 E2 3.1 69 18.8 0.32/0.64 20 80 980 E3 3.2 74 20.1 0.32/0.63 20 80 650 E4 3.2 73 19.8 0.33/0.63 20 80 608 E5 3.4 69 19.0 0.31/0.64 20 80 1030 E5a 3.2 75 20.5 0.31/0.64 20 80 645 E6 3.2 75 20.4 0.32/0.64 20 80 850 E7 3.2 77 20.9 0.31/0.64 20 80 480 E8 3.4 79 21.5 0.31/0.64 20 80 520 E9 3.4 72 19.9 0.31/0.64 20 80 620 E10 3.2 66 18.3 0.32/0.64 20 80 990 E10a 3.4 60 16.5 0.31/0.64 20 80 1125

Example 2: Synthesis of Compound 1 (CBZT1)

(13) a) 6-Bromo-2-fluoro-2′-methoxybiphenyl

(14) ##STR01367##

(15) 200 g (664 mmol) of 1-bromo-3-fluoro-2-iodobenzene, 101 g (664 mmol) of 2-methoxyphenylboronic acid and 137.5 g (997 mmol) of sodium tetra-borate are dissolved in 1000 ml of THF and 600 ml of water and degassed. 9.3 g (13.3 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1 g (20 mmol) of hydrazinium hydroxide are added. The reaction mixture is subsequently stirred at 70° C. under a protective-gas atmosphere for 48 h. Toluene is added to the cooled solution, which is washed a number of times with water, dried and evaporated. The product is purified by column chromatography on silica gel with toluene/heptane (1:2). Yield: 155 g (553 mmol), 83% of theory.

(16) b) 6′-Bromo-2′-fluorobiphenyl-2-ol

(17) ##STR01368##

(18) 112 g (418 mmol) of 6-bromo-2-fluoro-2′-methoxybiphenyl are dissolved in 2 l of dichloromethane and cooled to 5° C. 41.01 ml (431 mmol) of boron tribromide are added dropwise to this solution over the course of 90 min. and stirring is continued overnight. Water is subsequently added slowly to the mixture, the organic phase is washed three times with water, dried over Na.sub.2SO.sub.4 and evaporated in a rotary evaporator, and the product is purified by chromatography. Yield: 104 g (397 mmol), 98% of theory.

(19) c) 1-Bromodibenzofuran

(20) ##STR01369##

(21) 111 g (416 mmol) of 6′-bromo-2′-fluorobiphenyl-2-ol are dissolved in 2 l of SeccoSolv® DMF (max. 0.003% of H.sub.2O) and cooled to 5° C. 20 g (449 mmol) of sodium hydride (60% suspension in paraffin oil) are added to this solution, stirring is continued for a further 20 min. after the addition is complete, and the mixture is then heated at 100° C. for 45 min. After cooling, 500 ml of ethanol are slowly added to the mixture, the mixture is evaporated in a rotary evaporator, and the product is then purified by chromatography. Yield: 90 g (367 mmol), 88.5% of theory.

(22) d) Dibenzofuran-1-boronic acid

(23) ##STR01370##

(24) 180 g (728 mmol) of 1-bromodibenzofuran are dissolved in 1500 ml of dry THF and cooled to −78° C. 305 ml (764 mmol/2.5 M in hexane) of n-butyllithium are added at this temperature over the course of about 5 min., and the mixture is subsequently stirred at −78° C. for a further 2.5 h. 151 g (1456 mmol) of trimethyl borate are added as rapidly as possible at this temperature, and the reaction mixture is allowed to come slowly to room temperature (about 18 h). The reaction solution is washed with water, and the precipitated solid and the organic phase are dried azeotropically with toluene. The crude product is washed by stirring with toluene/methylene chloride at about 40° C. and filtered off with suction. Yield: 146 g (690 mmol), 95% of theory.

(25) e) 2-Dibenzofuran-1-yl-4,6-diphenyl-1,3,5-triazine

(26) ##STR01371##

(27) 23 g (110.0 mmol) of dibenzofuran-1-boronic acid, 29.5 g (110.0 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 21 g (210.0 mmol) of sodium carbonate are suspended in 500 ml of ethylene glycol damine ether and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/heptane. The yield is 37 g (94 mmol), corresponding to 87% of theory.

(28) f) 2-(8-Bromodibenzofuran-1-yl)-4,6-diphenyl-1,3,5-triazine

(29) ##STR01372##

(30) 70 g (190.0 mmol) of 2-dibenzofuran-1-yl-4,6-diphenyl-1,3,5-triazine are suspended in 2000 ml of acetic acid (100%) and 2000 ml of sulfuric acid (95-98%). 34 g (190 mmol) of NBS are added in portions to this suspension, and the mixture is stirred in the dark for 2 h. Water/ice is then added, and the solid is separated off and rinsed with ethanol. The residue is recrystallised from toluene. The yield is 80 g (167 mmol), corresponding to 87% of theory.

(31) g) 3-[9-(4,6-Diphenyl-1,3,5-triazin-2-yl)dibenzofuran-2-yl]-9-phenyl-9H-carbazole

(32) ##STR01373##

(33) 75 g (156 mmol) of 2-(8-bromodibenzofuran-1-yl)-4,6-diphenyl-1,3,5-triazine, 50 g (172 mmol) of N-phenylcarbazole-3-boronic acid [854952-58-2] and 36 g (340 mmol) of sodium carbonate are suspended in 1000 ml of ethylene glycol diamine ether and 280 ml of water. 1.8 g (1.5 mmol) of tetrakis(triphenyl-phosphine)palladium(0) are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The product is purified by column chromatography on silica gel with toluene/heptane (1:2) and subsequently sublimed in a high vacuum (p=5×10.sup.−7 mbar) (purity 99.9%). The yield is 50 g (78 mmol), corresponding to 50% of theory.

(34) The following compounds can be prepared analogously. The purification here can also be carried out using column chromatography, or other common solvents, such as n-heptane, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, N,N-dimethylformamide, tetrahydrofuran, ethyl acetate, n-butyl acetate or 1,4-dioxane, can be used for the recrystallisation or hot extraction.

(35) TABLE-US-00019 Starting material 1 G1 G2 G3 G4 G5 G6 G7 0 G8 G9 G10 G11 G12 G13 G14 G15 G16 G17 0 G18 G19 G20 G21 G50 G51 G52 Starting material 2 G1 G2 G3 00 G4 01 G5 02 G6 03 G7 04 G8 05 G9 06 G10 07 G11 08 G12 09 G13 0 G14 G15 G16 G17 G18 G19 G20 G21 G50 G51 0 G52 Product Yield G1 61% G2 56% G3 63% G4 60% G5 65% G6 54% G7 59% G8 60% G9 0 62% G10 54% G11 52% G12 50% G13 62% G14 57% G15 62% G16 56% G17 52% G18 55% G19 0 60% G20 54% G21 56% G50 62% G51 66% G52 55%

Example 3: Synthesis of Compounds 89 (BISC2) and 90 (BISC3)

(36) Compound 89 is known from the literature and is prepared analogously to US 20150001488.

(37) Compound 90 is known from the literature and is prepared analogously to Physical Chemistry Chemical Physics, 17(37), 2015, 24468-24474.

Example 4

(38) The following compounds can be prepared analogously to Example 2g). The purification here can also be carried out using column chromatography, or other common solvents, such as n-heptane, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, N,N-dimethylformamide, tetrahydrofuran, ethyl acetate, n-butyl acetate or 1,4-dioxane, can be used for the recrystallisation or hot extraction.

(39) TABLE-US-00020 Starting material 1 G23 G24 G25 G26 G27 0 G28 G29 G30 G31 G32 Starting material 2 G23 G24 G25 G26 G27 0 G28 G29 G30 G31 G32 Product Yield G23 62% G24 67% G25 64% G26 58% G27 0 53% G28 70% G29 59% G30 68% G31 53% G32 50%

Example 5

(40) A)

(41) Preparation of the bromine intermediate analogously to Example 2f) starting from 2-(dibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine [1651203-47-2]. Yield 83%.

(42) ##STR01476##
B)

(43) The following compounds can be prepared analogously to Example 2g). The purification here can also be carried out using column chromatography, or other common solvents, such as n-heptane, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, N,N-dimethylformamide, tetrahydrofuran, ethyl acetate, n-butyl acetate or 1,4-dioxane, can be used for the recrystallisation or hot extraction.

(44) TABLE-US-00021 Starting material 1 Starting material 2 Product Yield G34 63% G35 0 56% G36 66% G37 58% G38 0 65%

Example 6

(45) The following compounds can be prepared analogously to Example 2g). The purification here can also be carried out using column chromatography, or other common solvents, such as n-heptane, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, N,N-dimethylformamide, tetrahydrofuran, ethyl acetate, n-butyl acetate or 1,4-dioxane, can be used for the recrystallisation or hot extraction.

(46) TABLE-US-00022 Starting material 1 Starting material 2 Product Yield G40 58% G41 49% G42 00 66% G43 01 02 03 47% G44 04 05 06 51% G45 07 08 09 60% G46 0 49% G47 57% G48 41% G49 0 53%