MATERIALS FOR ELECTRONIC DEVICES

Abstract

The present application relates to compounds of a formula (I), (II) or (III), to processes for preparing such compounds, and to electronic devices comprising one or more such compounds, and to the use of such compounds in electronic devices.

Claims

1.-19. (canceled)

20. A compound of one of the following formulae: ##STR00268## where: A is a group selected from the following formulae: ##STR00269## which is bonded to L.sup.1 via the bond marked *; Z is the same or different at each instance and is selected from CR.sup.1 and N; Ar.sup.L is the same or different at each instance and is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and are substituted by R.sup.2 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and are substituted by R.sup.2 radicals; k is 0, 1, 2 or 3, where, when k=0, the Ar.sup.L group is absent and the two groups that bind to Ar.sup.L in formula (I), (II) and (III) are bonded directly to one another, where, when k=2, two Ar.sup.L groups are bonded successively in a chain, and where, when k=3, three Ar.sup.L groups are bonded successively in a chain; in the case that k=0, Ar.sup.1 is the same or different at each instance and is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and are substituted by R.sup.3 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and are substituted by R.sup.3 radicals, where at least one Ar.sup.1 group is selected from the following groups in which the bond to the nitrogen atom in formula (II) is labelled *: ##STR00270## ##STR00271## when k=1, 2 or 3, Ar.sup.1 is the same or different at each instance and is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and are substituted by R.sup.3 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and are substituted by R.sup.3 radicals; L.sup.1 is the same or different at each instance and is a single bond, an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R.sup.5 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R.sup.5 radicals; L.sup.2 is the same or different at each instance and is a single bond, an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R.sup.5 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R.sup.5 radicals; L.sup.3 is the same or different at each instance and is an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R.sup.5 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R.sup.5 radicals; Y is the same or different at each instance and is selected from O and S, V is the same or different at each instance and is selected from Si(R.sup.3).sub.2, C(R.sup.3).sub.2 and a group ##STR00272## where the dotted bonds are the bonds to the radical of the formula Ar.sup.1-3, Ar.sup.1-4 or Ar.sup.1-5; R.sup.1 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(O)R.sup.6, CN, Si(R.sup.6).sub.3, N(R.sup.6).sub.2, P(O)(R.sup.6).sub.2, OR.sup.6, S(O)R.sup.6, S(O).sub.2R.sup.6, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms excluding fluorenyl, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.1 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R.sup.6 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, CO, CNR.sup.6, C(O)O, C(O)NR.sup.6, NR.sup.6, P(O)(R.sup.6), O, S, SO or SO.sub.2; R.sup.2 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(O)R.sup.6, CN, Si(R.sup.6).sub.3, N(R.sup.6).sub.2, P(O)(R.sup.6).sub.2, OR.sup.6, S(O)R.sup.6, S(O).sub.2R.sup.6, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.2 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R.sup.6 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, CO, CNR.sup.6, C(O)O, C(O)NR.sup.6, NR.sup.6, P(O)(R.sup.6), O, S, SO or SO.sub.2; R.sup.3 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(O)R.sup.6, CN, Si(R.sup.6).sub.3, N(R.sup.6).sub.2, P(O)(R.sup.6).sub.2, OR.sup.6, S(O)R.sup.6, S(O).sub.2R.sup.6, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.3 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R.sup.6 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, CO, CNR.sup.6, C(O)O, C(O)NR.sup.6, NR.sup.6, P(O)(R.sup.6), O, S, SO or SO.sub.2; R.sup.4 is the same or different at each instance and is selected from straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where any two R.sup.4 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R.sup.6 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, CO, CNR.sup.6, C(O)O, C(O)NR.sup.6, NR.sup.6, P(O)(R.sup.6), O, S, SO or SO.sub.2; with the proviso that no two R.sup.4 radicals bonded to the same carbon atom may both be aromatic ring systems; R.sup.5 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(O)R.sup.6, CN, Si(R.sup.6).sub.3, N(R.sup.6).sub.2, P(O)(R.sup.6).sub.2, OR.sup.6, S(O)R.sup.6, S(O).sub.2R.sup.6, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.5 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R.sup.6 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, CO, CNR.sup.6, C(O)O, C(O)NR.sup.6, NR.sup.6, P(O)(R.sup.6), O, S, So or SO.sub.2; R.sup.3 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(O)R.sup.7, CN, Si(R.sup.7).sub.3, N(R.sup.7).sub.2, P(O)(R.sup.7).sub.2, OR.sup.7, S(O)R.sup.7, S(O).sub.2R.sup.7, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.6 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups mentioned and the aromatic ring systems and heteroaromatic ring systems mentioned are each substituted by R.sup.7 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned may be replaced by R.sup.7CCR.sup.7, CC, Si(R.sup.7).sub.2, CO, CNR.sup.7, C(O)O, C(O)NR.sup.7, NR.sup.7, P(O)(R.sup.7), O, S, SO or SO.sub.2; R.sup.7 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.7 radicals may be joined to one another and may form a ring; and where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems mentioned may be substituted by one or more radicals selected from F and CN.

21. The compound according to claim 20, wherein Z is CR.sup.1.

22. The compound according to claim 20, wherein Ar.sup.L is the same or different at each instance and is selected from phenyl, biphenyl, naphthyl and fluorenyl, each substituted by R.sup.2 radicals.

23. The compound according to claim 20, wherein the L.sup.1 is the same or different at each instance and is selected from single bond, phenylene substituted by R.sup.5 radicals, naphthylene substituted by R.sup.5 radicals, fluorenylene substituted by R.sup.5 radicals, and biphenylene substituted by R.sup.5 radicals.

24. The compound according to claim 20, wherein L.sup.2 is the same or different at each instance and is selected from single bond, phenylene substituted by R.sup.5 radicals, naphthylene substituted by R.sup.5 radicals, fluorenylene substituted by R.sup.5 radicals, and biphenylene substituted by R.sup.5 radicals.

25. The compound according to claim 20, wherein L.sup.3 is the same or different at each instance and is selected from phenylene substituted by R.sup.5 radicals, naphthylene substituted by R.sup.5 radicals, fluorenylene substituted by R.sup.5 radicals, and biphenylene substituted by R.sup.5 radicals.

26. The compound according to claim 20, wherein k=1, 2 or 3, and Ar.sup.1 is the same or different at each instance and is selected from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, fluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, where each of the monovalent groups is substituted by R.sup.3 radicals.

27. The compound according to claim 20, wherein, in the compounds of one of the formulae (I) to (III), zero, one, two or three R.sup.1 groups per formula are not H or D, and in that these groups that are not H or D are the same or different at each instance and are selected from F, CN, Si(R.sup.6).sub.3, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 25, aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, where the alkyl groups mentioned, the aryl groups mentioned and the heteroaryl groups mentioned are each substituted by R.sup.6 radicals.

28. The compound according to claim 20, wherein the compounds of one of the formulae (I) to (III) have at least one R.sup.1 group that is a phenyl groups substituted by R.sup.6 radicals.

29. The compound according to claim 20, wherein all R.sup.1 radicals in formulae (I) to (III) are H or D.

30. The compound according to claim 20, wherein R.sup.4 is the same or different at each instance and is selected from straight-chain alkyl groups which have 1 to 20 carbon atoms and are each substituted by R.sup.6 radicals, and branched or cyclic alkyl groups which have 3 to 20 carbon atoms and are each substituted by R.sup.6 radicals; where any two R.sup.4 radicals may be joined to one another and may form a ring.

31. The compound according to claim 20, wherein the compound conforms to one of the following formulae: ##STR00273## ##STR00274## where the groups that occur are as defined in claim 20; or in that the compound conforms to one of the following formulae: ##STR00275## ##STR00276## where the groups that occur are as defined in claim 20, and where Ar.sup.1 is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and are substituted by R.sup.3 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and are substituted by R.sup.3 radicals; or in that the compound conforms to one of the following formulae: ##STR00277## where the groups that occur are defined in claim 20.

32. The compound according to claim 20, wherein the unit ##STR00278## in formulae (I), (II) and (III) has one of the following structures: ##STR00279## ##STR00280## where R.sup.1 and R.sup.6 are as defined in claim 20.

33. A process for preparing the compound according to claim 20, comprising reacting a terphenyl derivative a) substituted by a reactive group in a coupling reaction with a secondary amine, or b) reacting in a coupling reaction with an aromatic or heteroaromatic species bearing a boron-containing group.

34. An oligomer, polymer or dendrimer containing one or more compounds according to claim 20, wherein the bond(s) to the polymer, oligomer or dendrimer may be localized at any desired positions substituted by R.sup.1, R.sup.1, R.sup.3, R.sup.4 or R.sup.5 in formula (I), (II) and (III).

35. A formulation comprising at least one compound according to claim 20 and at least one solvent.

36. An electronic device comprising at least one compound according to claim 20.

37. The electronic device according to claim 36, wherein the device is an organic electroluminescent device and comprises an anode, cathode and at least one emitting layer, and wherein the compound is present in a hole-transporting layer or in an emitting layer of the device.

38. A method comprising proving the compound according to claim 20 and incorporating the compound in an electronic device.

Description

EXAMPLES

A) Synthesis Examples

1) Synthesis of 4-{[1,1-biphenyl]-4-yl}-3-bromo-1,1-biphenyl 1a

[0166] ##STR00182##

[0167] 16.5 g (83.5 mmol) of biphenylboronic acid, 30 g (83.5 mmol) of 3-bromo-4-iodo-1,1-biphenyl and 1.2 g (2 mmol) of bis(triphenylphosphine)Pd(II) chloride and 23 g (167 mmol) of potassium carbonate are suspended in 520 ml of acetonitrile and 220 ml of methanol. The reaction mixture is heated to boiling under a protective atmosphere overnight. The mixture is then filtered with suction and the filtride is washed with MeOH, water and MeOH again. The residue is purified by crystallization with MeOH. Yield: 29 g (85% of theory), purity by GC-MS >94%.

[0168] The following compounds are prepared in an analogous manner:

TABLE-US-00001 Ex. Halogen derivative Boronic acid Product 1b [00183] [00184] [00185] 1c [00186] [00187] [00188] 1d [00189] [00190] [00191] 1e [00192] [00193] [00194] 1f [00195] [00196] [00197]

2) Synthesis of N-(4-{[1,1-biphenyl]-4-yl}-[1,1-biphenyl]-3-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine 2a

[0169] ##STR00198##

[0170] N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (30 g, 75 mmol), 4-{[1,1-biphenyl]-4-yl}-3-bromo-1,1-biphenyl (29 g, 75 mmol) and sodium tert-butoxide (14.7 g, 150 mmol) are dissolved in 350 ml of toluene. The solution is degassed and saturated with N.sub.2. Then tri-tert-butylphosphine (7.5 ml; 7.5 mmol, 1 M in xylene) and 3.4 g (3.8 mmol) of Pd.sub.2(dba).sub.3 are added thereto. The reaction mixture is heated to boiling under a protective atmosphere overnight. The mixture is cooled and partitioned between toluene and water and the organic phase is washed three times with water and dried over Na.sub.2SO.sub.4 and concentrated by rotary evaporation. After the crude product has been filtered through silica gel with toluene, the remaining residue is recrystallized from toluene and finally sublimed under high vacuum; purity is 99.9%. The yield is 23.9 g (45% of theory).

[0171] The following compounds are prepared in an analogous manner:

TABLE-US-00002 Ex. Halide Amine Product 2b [00199] [00200] [00201] 2c [00202] [00203] [00204] 2d [00205] [00206] [00207] 2e [00208] [00209] [00210] 2f [00211] [00212] [00213] 2g [00214] [00215] [00216] 2h [00217] [00218] [00219] 2i [00220] [00221] [00222] 2j [00223] [00224] [00225]

3) Synthesis of N-[4-(4-{[1,1-biphenyl]-4-yl}-[1,1-biphenyl]-3-yl)phenyl]-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine 3a

[0172] ##STR00226##

[0173] 25.9 g (43 mmol) of N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-fluoren-2-amine and 16.6 g (43 mmol) of 4-{[1,1-biphenyl]-4-yl}-3-bromo-1,1-biphenyl are suspended in 400 ml of dioxane and 13.7 g of caesium fluoride (90 mmol). 4.0 g (5.4 mmol) of bis(tricyclohexylphosphine)palladium dichloride is added to this suspension, and the reaction mixture is heated under reflux for 18 h. After cooling, the organic phase is removed, filtered through silica gel, washed three times with 80 ml of water and then concentrated to dryness. After the crude product has been filtered through silica gel with toluene, the remaining residue is recrystallized from toluene and finally sublimed under high vacuum, purity is 99.9%. The yield is 11 g (33% of theory).

[0174] The following compounds are prepared in an analogous manner:

TABLE-US-00003 Ex. Halide Amine Product 3b [00227] [00228] [00229] 3c [00230] [00231] [00232] 3d [00233] [00234] [00235] 3e [00236] [00237] [00238] 3f [00239] [00240] [00241] 3g [00242] [00243] [00244] 3h [00245] [00246] [00247]

B) Device Examples

1) General Production Process for the OLEDs and Characterization of the OLEDs

[0175] Glass plates which have been coated with structured ITO (indium tin oxide) in a thickness of 50 nm form the substrates to which the OLEDs are applied.

[0176] The OLEDs basically have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL1)/optional second hole transport layer (HTL2)/electron blocker layer (EBL)/emission layer (EML)/optional hole blocker layer (HBL)/electron transport layer (ETL1)/optional second electron transport layer (ETL2)/electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer of thickness 100 nm. The exact structure of the OLEDs can be found in the tables which follow. The materials required for production of the OLEDs are shown in table 7. The HTM-a material used in the HIL and the HTL is a fluorene derivative. The p-dopant A used is NDP-9 from Novaled AG, Dresden.

[0177] All materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the emission layer consists of at least one matrix material (host material) 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 H:SEB (95%:5%) mean here that the material H is present in the layer in a proportion by volume of 95% and SEB in a proportion of 5%. Analogously, the electron transport layer and the hole injection layer also consist of a mixture of two materials.

[0178] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the external quantum efficiency (EQE, measured in %) as a function of the luminance, calculated from current-voltage-luminance characteristics assuming Lambertian radiation characteristics, and the lifetime are determined. The parameter EQE @ 10 mA/cm.sup.2 refers to the external quantum efficiency which is attained at 10 mA/cm.sup.2. The lifetime LT is defined as the time after which the luminance drops from the starting luminance to a certain proportion in the course of operation with constant current density. An LT90 figure means here that the lifetime reported corresponds to the time after which the luminance has dropped to 90% of its starting value. The figure @60 mA/cm.sup.2, for example, means here that the lifetime in question is measured at 60 mA/cm.sup.2.

2) Examples of Use of the Compounds in the EBL of Blue-Fluorescing OLEDs

[0179] OLEDs are produced with the following structure:

TABLE-US-00004 TABLE 1 OLED structure Ex. HIL HTL1 HTL2 EBL EML ETL1 EIL Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ nm nm nm nm nm nm nm 1 HTM: p- HTM HTM-1: p- HTM-1 H:SEB ETM:LiQ LiQ dopant (5%) 160 nm dopant 10 nm (95%:5%) (50:50%) 1 nm 20 nm (5%) 20 nm 30 nm 20 nm 2 HTM: p- HTM HTM-2: p- HTM-2 H:SEB ETM:LiQ LiQ dopant (5%) 160 nm dopant 10 nm (95%:5%) (50:50%) 1 nm 20 nm (5%) 20 nm 30 nm 20 nm 3 HTM: p- HTM HTM-3: p- HTM-3 H:SEB ETM:LiQ LiQ dopant (5%) 160 nm dopant 10 nm (95%:5%) (50:50%) 1 nm 20 nm (5%) 20 nm 30 nm 20 nm 4 HTM: p- HTM HTM-4: p- HTM-4 H:SEB ETM:LiQ LiQ dopant (5%) 160 nm dopant 10 nm (95%:5%) (50:50%) 1 nm 20 nm (5%) 20 nm 30 nm 20 nm

[0180] OLEDs 1 to 4 show that the compounds according to the present application are of good suitability for use in the electron blocker layer of blue-fluorescing OLEDs.

[0181] The OLEDs have good results for lifetime, efficiency and operating voltage, as shown in the following table:

TABLE-US-00005 TABLE 2 OLED data LT90 V (at EQE @ (at 10 mA/ 10 mA/ 60 mA/ Ex. cm.sup.2) cm.sup.2 cm.sup.2) 1 3.60 7.56 176 2 3.79 8.39 173 3 3.47 8.16 124 4 3.67 8.44 184

3) Examples of Use of the Compounds in the EBL of Green-Phosphorescing OLEDs

[0182] OLEDs are produced with the following structure:

TABLE-US-00006 TABLE 3 OLED structure Ex. HIL HTL1 EBL EML ETL1 ETL2 EIL Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ nm nm nm nm nm nm nm 5 HTM: p- HTM HTM-1 TMM-1 (59%): ETM ETM:LiQ LiQ dopant (5%) 220 nm 10 nm TMM- 10 nm (50:50%) 1 nm 20 nm 2(29%):TEG(12%) 30 nm 30 nm 6 HTM: p- HTM HTM-2 TMM-1 (59%): ETM ETM:LiQ LiQ dopant (5%) 220 nm 10 nm TMM- 10 nm (50:50%) 1 nm 20 nm 2(29%):TEG(12%) 30 nm 30 nm 7 HTM: p- HTM HTM-3 TMM-1 (59%): ETM ETM:LiQ LiQ dopant (5%) 220 nm 10 nm TMM- 10 nm (50:50%) 1 nm 20 nm 2(29%):TEG(12%) 30 nm 30 nm 8 HTM: p- HTM HTM-4 TMM-1 (59%): ETM ETM:LiQ LiQ dopant (5%) 220 nm 10 nm TMM- 10 nm (50:50%) 1 nm 20 nm 2(29%):TEG(12%) 30 nm 30 nm

[0183] OLEDs 5 to 8 show that the compounds according to the present application are of good suitability for use in the electron blocker layer of green-phosphorescing OLEDs.

[0184] The OLEDs have good results for lifetime, efficiency and operating voltage, as shown in the following table:

TABLE-US-00007 TABLE 4 OLED data LT90 V (at EQE @ (at 2 mA/ 10 mA/ 40 mA/ Ex. cm.sup.2) cm.sup.2 cm.sup.2) 5 3.99 16.76 131 6 3.92 18.36 141 7 3.69 16.86 182 8 3.80 18.79 121

4) Example of Use of the Compounds in the HIL of Blue-Fluorescing OLEDs

[0185] OLEDs are produced with the following structure:

TABLE-US-00008 TABLE 5 OLED structure Ex. HIL HTL1 EBL EML ETL1 EIL Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ nm nm nm nm nm nm 9 HTM-1: p- HTM-1 EBM H:SEB ETM:LiQ LiQ dopant (5%) 180 nm 10 nm (95%:5%) (50:50%) 1 nm 20 nm 20 nm 30 nm 10 HTM-1: p- HTM-3 EBM H:SEB ETM:LiQ LiQ dopant (5%) 180 nm 10 nm (95%:5%) (50:50%) 1 nm 20 nm 20 nm 30 nm

[0186] OLEDs 9 and 10 show that the compounds according to the present application are of good suitability for use in the hole injection layer of blue-fluorescing OLEDs.

[0187] The OLEDs have good results for lifetime, efficiency and operating voltage, as shown in the following table:

TABLE-US-00009 TABLE 6 OLED data V (at EQE @ LT90 (at 10 mA/ 10 mA/ 60 mA/ Ex. cm.sup.2) cm.sup.2 cm.sup.2) 9 3.85 9.26 167 10 3.84 9.76 110

[0188] HTM-2 and HTM-4 can likewise be used as HIL in blue-fluorescing OLEDs, in a correspondingly suitable OLED stack.

5) Use of the Compounds in the EBL of Green-Phosphorescing OLEDs

[0189] OLEDs are produced with the following structure:

TABLE-US-00010 Ex. HIL HTL EBL EML HBL ETL EIL Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ nm nm nm nm nm nm nm 11 HTM-a: p- HTM-a HTM-5 TMM-1a (32%) HBM 5nm ETM-a: LiQ dopant A 50 nm 30 nm TMM-2a (60%) LiQ(50%) 1 nm (5%) TEG-a (8%) 30 nm 10 nm 35 nm

TABLE-US-00011 Data of the OLEDs EQE @ V (at LT90 (at 10 mA/ 10 mA/ 60 mA/ Ex. cm.sup.2 cm.sup.2) cm.sup.2) 11 23.17 4.1 110

[0190] HTM-1 to HTM-4 may be used in place of HTM-5 in the stack shown above.

TABLE-US-00012 TABLE 7 Materials used [00248] [00249] [00250] [00251] [00252] [00253] [00254] [00255] [00256] [00257] [00258] [00259] [00260] [00261] [00262] [00263] [00264] [00265] [00266] [00267]