MATERIALS FOR ELECTRONIC DEVICES

Abstract

The present application relates to a compound which contains an indenocarbazole group, a particular arylamino group and an electron-deficient group bonded to the indenocarbazole group. The compound is suitable for use in electronic devices, in particular in organic electroluminescent devices.

Claims

1.-18. (canceled)

19. A compound of the formula (1) ##STR00357## where the following applies to the symbols and indices used: Y is, identically or differently, equal to N or CR.sup.1, where at least one group Y in the six-membered ring must be equal to N; W is, identically or differently, equal to CR.sup.1 or N; V is, identically or differently, equal to CR.sup.1 or N, with the proviso that two adjacent groups V=V stand for a group of the formula (2) ##STR00358## or two adjacent group V-V stand for a group of formula (3) ##STR00359## in which the dashed bonds indicate the linking of this unit; X is a divalent bridge selected from N(R.sup.2), B(R.sup.2), O, C(R.sup.2).sub.2, Si(R.sup.2).sub.2, C═NR.sup.2, C═C(R.sup.2).sub.2, S, S═O, SO.sub.2, P(R.sup.2) and P(═O)R.sup.2; Ar.sup.1, Ar.sup.2 are, identically or differently, an aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R.sup.1; wherein at least one of the group Ar.sup.1 or Ar.sup.2 stands for an aromatic ring system having 12 to 30 aromatic C atoms, an heteroaryl group having 13 to 30 aromatic ring atoms or an aryl group having 10 to 20 aromatic C atoms, each of which may be substituted by one or more radicals R.sup.1, Ar.sup.1 Ar.sup.3, Ar.sup.4 are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic C atoms or an heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R.sup.1; with the proviso that Ar.sup.4 is not an anthracenylene group; E is on each occurrence, identically or differently, a single bond, N(R.sup.3), O, S, C(R.sup.3).sub.2, C(R.sup.3).sub.2—C(R.sup.3).sub.2, Si(R.sup.3).sub.2 or B(R.sup.3); is on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R.sup.3, CN, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, P(═O)(R.sup.3).sub.2, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.3 and where one or more CH.sub.2 groups in the above-mentioned groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, C═O, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, SO or SO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 30 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 30 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3, where two adjacent radicals R.sup.1 located on Ar.sup.1 or two adjacent radicals R.sup.1 located on Ar.sup.2 may be linked to one another and may form a ring; R.sup.2 is on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R3, CN, Si(R3)3, N(R.sup.3).sub.2, P(═O)(R.sup.3).sub.2, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.3 and where one or more CH.sub.2 groups in the above-mentioned groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, C═O, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, SO or SO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 30 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 30 aromatic ring atoms, which may be substituted by one or more radicals R.sup.3; where two radicals R.sup.2 may be linked to one another and may form a ring; is on each occurrence, identically or differently, H, D, F, Br, Cl, I, C(═O)R.sup.4, CN, Si(R.sup.4).sub.3, N(R.sup.4).sub.2, P(═O)(R.sup.4).sub.2, S(═O)R.sup.4, S(═O).sub.2R.sup.4, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.4 and where one or more CH.sub.2 groups in the above-mentioned groups may be replaced by —R.sup.4C═CR.sup.4—, —C≡C—, Si(R.sup.4).sub.2, C═O, C═NR.sup.4, —C(═O)O—, —C(═O)NR.sup.4—, NR.sup.4, P(═O)(R.sup.4), —O—, —S—, SO or SO.sub.2, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.4, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R.sup.4, where two or more radicals R.sup.3 may be linked to one another and may form a ring; R.sup.4 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by D or F; two or more substituents R.sup.4 here may be linked to one another and may form a ring; n is equal to 0 or 1; and m is equal to 0 or 1.

20. The compound according to claim 19, wherein the index m is equal to 1.

21. The compound according to claim 19, wherein the index n is equal to 0.

22. The compound according to claim 19, wherein W is equal to CR.sup.1.

23. The compound according to claim 19, wherein X is equal to C(R.sup.2).sub.2.

24. The compound according to claim 19, wherein at least two groups Y in the ring are equal to N, and the remaining groups Y are equal to CR.sup.1.

25. The compound according to claim 19, wherein precisely three groups Y in the ring are equal to N, and the remaining groups Y are equal to CR.sup.1.

26. The compound according to claim 19, wherein Ar.sup.4 represents a group of the following formula (Ar.sup.4-I) ##STR00360## formula (Ar.sup.4-I), where the dashed lines represent the bonds to the indenocarbazole group and the group —NAr.sup.1Ar.sup.2, Ar.sup.5 is on each occurrence, identically or differently, an aryl or heteroaryl group having 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R.sup.1, where R.sup.1 is defined as in claim 19; and k is 1, 2, 3 or 4, where the index k is selected so that the number of aromatic ring atoms in the entire group Ar.sup.4 does not exceed the number 40.

27. The compound according to claim 19, wherein at least one of the groups Ar.sup.1 and Ar.sup.2 is selected, identically or differently, from the group consisting of biphenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, naphtyl, anthracyl, phenantryl, chrysenyl, triphenylenyl, pyrenyl, perylenyl, each of which may be substituted by one or more radicals R.sup.3.

28. The compound according to claim 19, wherein at least one of the groups Ar.sup.1 and Ar.sup.2 is selected, identically or differently, from the groups of the following formulae (11) to (77), ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370## ##STR00371## ##STR00372## where the dashed lines represent the bonds to the N atom and the group Ar.sup.1 or Ar.sup.2, and the groups may be substituted by one or more radicals R.sup.3 as defined in claim 19.

29. The compound according to claim 19, wherein the group of the formula (Y) ##STR00373## as constituent of the formula (I) conforms to one of the following formulae (Y-1) to (Y-6), where the dashed line denotes the bond to the remainder of the compound, ##STR00374## and where R.sup.1 and R.sup.3 are as defined in claim 19.

30. An oligomer, polymer or dendrimer containing one or more compounds according to claim 19, where the bond(s) to the polymer, oligomer or dendrimer may be localised at any desired positions in formula (I) which are substituted by R.sup.1 or R.sup.2.

31. A formulation comprising at least one compound according to claim 19 and at least one solvent.

32. A formulation comprising at least one polymer, oligomer or dendrimer according to claim 30 and at least one solvent.

33. An electronic device which comprises the compound according to claim 19.

34. An electronic device selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs), wherein the device comprises at least one compound according to claim 19.

35. An organic electroluminescent device which comprises an anode, a cathode and at least one emitting layer, where at least one layer of the device, selected from emitting layers, electron-transport layers, electron-injection layers or hole-blocking layers, comprises at least one compound according to claim 19.

36. The organic electroluminescent device according to claim 35, wherein said at least one compound is present in an emitting layer in combination with one or more phosphorescent emitter compounds.

37. A process for the preparation of the compound according to claim 19, which comprises reacting an indenocarbazole compound with an aromatic or heteroaromatic ring system which contains an electron-deficient heteroaryl group, where the aromatic or heteroaromatic ring system is coupled to the nitrogen atom of the indenocarbazole.

Description

WORKING EXAMPLES

[0153] The following working examples serve to explain the invention. They are not intended to be interpreted as restrictive.

[0154] The following syntheses are, unless indicated otherwise, carried out under a protective-gas atmosphere in dried solvents. Compounds (I), (XIII) and (XII) can be prepared in accordance with WO2010136109. Compounds (II), (XV), (XVI), (XX), and (XXIV) are commercially available. Compounds (IV), (VI) and (XIII) can be prepared in accordance with WO201155912. Comparative compounds (A), (B), and (C) can be prepared in accordance with WO2010136109. (D) can be prepared in accordance with WO2012014500A1.

Example 1

Preparation of Compound (V)

Synthetic Procedure for the Preparation of Compound (V)

[0155] ##STR00342##

Preparation of Compound (III)

[0156] To the suspension of 2.4 g (60.7 mmol, 60% in oil) of NaH in 100 mL of DMF, 20.0 g (55.2 mmol) of compound (I) in 180 mL of DMF is slowly added to the suspension and stirred for 1 h at room temperature. 17.7 g (66.4 mmol) of compound (II) is dissolved in 80 mL of DMF and slowly added to the suspension, and the reaction mixture is stirred for 16 h. The reaction mixture is poured on to ice, the organic phase is separated off, extracted three times with 200 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is washed with ethanol, filtered off and finally dried under reduced pressure. The yield is 28.2 g (47.6 mmol), corresponding to 78% of theory.

Preparation of Compound (V)

[0157] 30.0 g (50.6 mmol) of compound (III), 24.6 g (55.8 mmol) of compound (IV) and 5.8 g (5.5 mmol) of sodium carbonate are suspended in 600 mL of toluene and 220 mL of water. 590 mg (0.51 mmol) of tetrakis(triphenylphosphine)palladium(0) are added to this suspension, and the reaction mixture is stirred under reflux for 16 h. After cooling, the organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue was washed with heptane, filtered off and finally dried under reduced pressure. The yield is 37.2 g (40.9 mmol), corresponding to 84% of theory.

Example 2

Preparation of Compound (VII)

Synthetic Procedure for the Preparation of Compound (VII)

[0158] ##STR00343##

Preparation of Compound (VII)

[0159] 28.5 g (48.1 mmol) of compound (III), 23.3 g (52.9 mmol) of compound (VI) and 5.5 g (52.1 mmol) of sodium carbonate are suspended in 600 mL of toluene and 220 mL of water. 0.56 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium(0) is added to this suspension, and the reaction mixture is stirred under reflux for 16 h. After cooling, the organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is recrystallized from toluene and heptane. The yield is 21.7 g (23.9 mmol), corresponding to 50% of theory.

Example 3

Preparation of Compound (IX)

Synthetic Procedure for the Preparation of Compound (IX)

[0160] ##STR00344##

[0161] 25 g (42.1 mmol) of compound (VIII), 20.5 g (52.9 mmol) of compound (IV) and 4.8 g (45.6 mmol) of sodium carbonate are suspended in 600 mL of toluene and 220 mL of water. 0.42 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium(0) is added to this suspension, and the reaction mixture is stirred under reflux for 16 h. After cooling, the organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is recrystallized from toluene and heptane. The yield is 26 g (28.6 mmol), corresponding to 68% of theory.

Example 4

Preparation of Compound (X)

Synthetic Procedure for the Preparation of Compound (X)

[0162] ##STR00345##

Preparation of Compound (X)

[0163] 30 g (50.5 mmol) of compound (VIII), 24.5 g (55.6 mmol) of compound (VI) and 5.8 g (54.7 mmol) of sodium carbonate are suspended in 600 mL of toluene, and 220 mL of water. 0.58 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium(0) is added to this suspension, and the reaction mixture is stirred under reflux for 16 h. After cooling, the organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is recrystallized from toluene and heptane. The yield is 27 g (29.7 mmol), corresponding to 64% of theory.

Example 5

Preparation of Compound (XIV)

Synthetic Procedure for the Preparation of Compound (XIV)

[0164] ##STR00346##

Preparation of Compound (XII)

[0165] 30.0 g (50.8 mmol) of compound (XI) is suspended in 750 mL of THF. 12.6 g (70.8 mmol) of NBS is slowly added to this suspension, and the reaction mixture is stirred at room temperature for overnight. The reaction mixture is quenched by water. The organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is recrystallized from toluene. The yield is 21.6 g (32.2 mmol), corresponding to 63% of theory.

Preparation of Compound (XIV)

[0166] 20 g (29.9 mmol) of compound (III), 14.5 g (32.9 mmol) of compound (VIII) and 3.4 g (32.4 mmol) of sodium carbonate are suspended in 600 mL of toluene, and 220 mL of water. 0.35 g (0.3 mmol) of tetrakis(triphenylphosphine)palladium(0) is added to this suspension, and the reaction mixture is stirred under reflux for 16 h. After cooling, the organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is recrystallized from toluene and heptane. The yield is 18 g (18.3 mmol), corresponding to 61% of theory.

Example 6

Preparation of Compound (XIX)

Synthetic Procedure for the Preparation of Compound (XIX)

[0167] ##STR00347##

Preparation of Compound (XVII)

[0168] 34.7 g (153.5 mmol) of compound (XV), 35.0 g (153.5 mmol) of compound (XVI) and 17.9 g (168.8 mmol) of sodium carbonate are suspended in 120 mL of toluene, 300 mL of dioxane and 300 mL of water. 1.8 g (1.5 mmol) of tetrakis(triphenylphosphine)palladium(0) are added to this suspension, and the reaction mixture is heated at 110° C. for 16 h. After cooling, the organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is recrystallized from toluene and heptane. The yield is 32 g (85.6 mmol), corresponding to 56% of theory.

Preparation of Compound (XVIII)

[0169] To the suspension of 2.4 g (60.7 mmol, 60% in oil) of NaH in 100 mL of DMF, 20.0 g (55.2 mmol) of compound (I) in 180 mL of DMF and slowly added to the suspension and stirred for 1 h at room temperature. 24.8 g (66.4 mmol) of compound (II) is dissolved in 80 mL of DMF and slowly added to the suspension, and the reaction mixture is stirred for 16 h. The reaction mixture is poured on to ice, the organic phase is separated off, extracted three times with 200 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is washed with ethanol, filtered off and finally dried under reduced pressure. The yield is 29 g (41.4 mmol), corresponding to 75% of theory.

Preparation of Compound (XIX)

[0170] 20 g (28.6 mmol) of compound (VIII), 13.8 g (31.5 mmol) of compound (IV) and 3.3 g (31 mmol) of sodium carbonate are suspended in 600 mL of toluene and 220 mL of water. 0.33 g (0.3 mmol) of tetrakis(triphenylphosphine)palladium(0) is added to this suspension, and the reaction mixture is stirred under reflux for 16 h. After cooling, the organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is recrystallized from toluene and heptane. The yield is 18 g (17.7 mmol), corresponding to 62% of theory.

Example 7

Preparation of Compound (XXIII)

Synthetic Procedure for the Preparation of Compound (XXIII)

[0171] ##STR00348##

Preparation of Compound (XXI)

[0172] The solution of 50.8 g (186.0 mmol) of compound (XV) in 580 mL of THF is added to 4.5 g (185.1 mmol) of Mg turnings and the reaction mixture is stirred for 16 h. The reaction mixture is added to the solution of 35.0 g (154.8 mmol) of compound (XX) in 190 mL of THF at 0° C. The reaction mixture is slowly warmed up to room temperature. After 24 h, the reaction mixture is quenched by 12% of HCl aqueous solution, then the organic phase is separated off, extracted three times with 500 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is purified by column chromatography on silica gel using a mixture of dichloromethane/heptanes (1/5). The yield is 24 g (62.5 mol), corresponding to 40% of theory.

Preparation of Compound (XXII)

[0173] To the suspension of 2.4 g (60.7 mmol, 60% in oil) of NaH in 100 mL of DMF, 20.0 g (55.2 mmol) of compound (I) in 180 mL of DMF and slowly added to the suspension and stirred for 1 h at room temperature. 25.4 g (66.3 mmol) of compound (XXI) is dissolved in 80 mL of DMF and slowly added to the suspension, and the reaction mixture is stirred for 16 h. The reaction mixture is poured on to ice, the organic phase is separated off, extracted three times with 200 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is washed with ethanol, filtered off and finally dried under reduced pressure. The yield is 30 g (42.3 mmol), corresponding to 77% of theory.

Preparation of Compound (XXIII)

[0174] 20 g (28.21 mmol) of compound (XXII), 13.7 g (31.0 mmol) of compound (VI) and 3.23 g (30.5 mmol) of sodium carbonate are suspended in 600 mL Of toluene and 220 ml of water. 0.33 g (0.3 mmol) of tetrakis(triphenyl-phosphine)palladium(0) is added to this suspension, and the reaction Mixture is stirred under reflux for 16 h. After cooling, the organic phase is separated off, extracted three times with 300 mL of dichloromethane, dried over magnesium sulfate and subsequently evaporated to dryness. The residue is recrystallized from toluene and heptane. The yield is 21 g (20.5 mmol), corresponding to 72% of theory.

Example 8

Preparation of Compound (XXV)

Synthetic Procedure for the Preparation of Compound (XXV)

[0175] ##STR00349##

Preparation of Compound (XXV)

[0176] 30.0 g (50.6 mmol) of compound (VIII) and 16.8 g (50.6 mmol) of compound (XXIV) are suspended in 500 mL of toluene under Ar atmosphere. 226 mg (1.0 mmol) of Pd(OAc).sub.2 are added to the flask and stirred under Ar atmosphere then 2.0 mL of a 1 M tri-tert-butylphosphine solution and 7.3 g (75.5 mmol) of sodium t-butoxide are added to the flask. The reaction mixture is stirred under reflux for 24 h. After cooling, the organic phase is separated off, washed three times with 200 mL of water, dried over magnesium sulfate, filtered and subsequently evaporated to dryness. The residue is purified by column chromatography on silica gel using a mixture of ethylacetate/heptane (1:3). The yield is 33.0 g (39.6 mmol), corresponding to 78% of theory

Examples 9 to 12

Preparation of a Solution-Processed OLED Devices

[0177] Compounds related to the present invention can be processed from solution to fabricate simple OLED devices with good performances. The preparation of these solution-processed OLED devices is similar to the preparation of polymer light-emitting diodes (PLEDs), which has been already widely described in the literature (eg. Example, in WO 2004/037887). In this case the compounds according to the invention (V), (VII), (IX), (X), (XIV), (XIX), (XXIII) and (XXV) were dissolved in toluene. The typical solids content of such solutions is between 16 and 25 g/L in order to achieve for a typical device a layer thickness of 80 nm by spin coating. The OLED devices show the following structure: ITO/PEDOT: PSS/interlayer/EML/cathode, where EML is the emissive layer. The emissive layer (EML) includes not only the compounds related to this invention (V), (VII), (IX), (X), (XIV), (XIX), (XXIII) and (XXV), which are present in a concentration of 80 wt %, but also a dopant, TEG-001 (commercially available by Merck), which is present in a concentration of 20%. Structured ITO substrates and the material for the so-called buffer layer (PEDOT, actually PEDOT: PSS) are commercially available (ITO of Technoprint and others, PEDOT: PSS as an aqueous dispersion Clevios Baytron® P from HC Starck. The interlayer is used for the hole injection; in this case, HIL-012 (commercially available by Merck) was used. HIL-012 is a polymer consisting of the following monomers:

##STR00350##

[0178] In an inert gas, argon atmosphere in this case, the emission layer is spin coated and heated at 120° C. for 10 minutes. Finally, a cathode of barium and aluminum is evaporated in vacuo. Between the emitting layer and the cathode, a hole blocking layer and/or an electron transport layer can also be evaporated. Also the interlayer can be replaced by one or more layers.

[0179] The devices are characterized by standard method and OLED examples are not optimized yet.

[0180] Structure of compounds related to the present invention and comparative examples.

##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356##

Example 9

[0181]

TABLE-US-00003 Max. Eff U@1000 cd/m.sup.2 CIE LT95 Compound [Cd/A] [V] [x/y] [h] A 48.7 6.2 0.32/0.62 52@8000 (IX) 63.8 4.2 0.32/0.62 88@8000

[0182] As can be seen from the results, the performances (in particular efficiency, lifetime and voltage) of a simple solution-processed OLED device fabricated with compound IX related to the present invention are better than the one obtained with comparative compound A.

Example 10

[0183]

TABLE-US-00004 Max. Eff U@1000 cd/m.sup.2 CIE LT95 Compound [Cd/A] [V] [x/y] [h] B 50.3 5.9 0.33/0.63 49@8000 (XIV) 65.0 3.9 0.31/0.63 90@8000

[0184] As can be seen from the results, the performances (in particular efficiency, lifetime and voltage) of a simple solution-processed OLED device fabricated with compound XIV related to the present invention are better than the one obtained with comparative compound B.

Example 11

[0185]

TABLE-US-00005 Max. Eff U@1000 cd/m.sup.2 CIE LT95 Compound [Cd/A] [V] [x/y] [h] C 47.9 5.8 0.33/0.61 50@8000 (XXV) 72.7 4.0 0.33/0.62 93@8000

[0186] As can be seen from the results, the performances (in particular efficiency, lifetime and voltage) of a simple solution-processed OLED device fabricated with compound XXV related to the present invention are better than the one obtained with comparative compound C.

Example 12

[0187]

TABLE-US-00006 Max. Eff U@1000 cd/m.sup.2 CIE LT95 Compound [Cd/A] [V] [x/y] [h] D 48.5 6.0 0.32/0.63 48@8000 (VII) 66.2 3.8 0.33/0.62 92@8000 (X) 64.3 4.0 0.33/0.60 87@8000 (XIV) 65.0 3.9 0.31/0.63 90@8000 (XIX) 66.1 3.7 0.31/0.63 95@8000

[0188] As can be seen from the results, the performances (in particular efficiency, lifetime and voltage) of a simple solution-processed OLED device fabricated with compounds VII, X, XIV and XIX related to the present invention are better than the one obtained with comparative compound D.