MATERIALS FOR ELECTRONIC DEVICES

Abstract

The present invention relates to an electronic device comprising anode, cathode and at least one organic layer which comprises a compound of the formula (I) to (IV). The invention furthermore encompasses the use of compounds of the formula (I) to (IV) in an electronic device and to a compound of the formula (Ic) to (IVc).

Claims

1-15. (canceled)

16. An electronic device comprising anode, cathode and at least one organic layer, wherein the organic layer comprises at least one compound of the following formulae (I) to (IV) ##STR00394## where the following applies to the symbols occurring: X is a single bond; L is a divalent, or in the case of k=3, 4, 5 or 6 a tri-, tetra-, penta- or hexavalent group respectively, selected from C═O, C═NR.sup.1, Si(R.sup.1).sub.2, P(═O)(R.sup.1), SO, SO.sub.2, alkylene groups having 1 to 20 C atoms, alkenylene or alkynylene groups having 2 to 20 C atoms, where, in the case of the groups mentioned, one or more CH.sub.2 groups is optionally replaced by Si(R.sup.1).sub.2, O, S, C═O, C═NR.sup.1, C═O—O, C═O—NR.sup.1, NR.sup.1, P(═O)(R.sup.1), SO or SO.sub.2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO.sub.2, aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R.sup.1, and any desired combinations of 1, 2, 3, 4 or 5 identical or different groups selected from the above-mentioned groups; or L is a single bond, where k in this case must be equal to 2; R.sup.0 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, C(═O)R.sup.1, OSO.sub.2R.sup.1, COOR.sup.1, CON(R.sup.1).sub.2, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.1 and where one or more CH.sub.2 groups in the above-mentioned groups is optionally replaced by Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, C═NR.sup.1, P(═O)(R.sup.1), SO, SO.sub.2, NR.sup.1, —O—, —S—,—COO— or —CONR.sup.1— and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO.sub.2, or 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.1, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R.sup.1, or a combination of these systems, furthermore, two or more adjacent radicals R.sup.0 is optionally linked to one another here and form an aliphatic or aromatic ring, or a radical R.sup.0 is optionally linked to an adjacent radical R via a single bond or a divalent group Y and form an aliphatic or aromatic ring; R is equal to C(═O)R.sup.1, OSO.sub.2R.sup.1, COOR.sup.1, CON(R.sup.1).sub.2, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.1 and where one or more CH.sub.2 groups in the above-mentioned groups is optionally replaced by Si(R.sup.1).sub.2, Ge(R.sup.1).sub.2, Sn(R.sup.1).sub.2, C═O, C═S, C═Se, C═NR.sup.1, P(═O)(R.sup.1), SO, SO.sub.2, NR.sup.1, —O—, —S—, —COO— or —CONR.sup.1— and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO.sub.2, or 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.1, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R.sup.1, or a combination of these systems, where furthermore the radical R is optionally linked to one or more adjacent radicals R.sup.0 via a single bond or a divalent group Y; Y is on each occurrence, identically or differently, a divalent group selected from C═O, C═S, C═NR.sup.1, C(R.sup.1).sub.2, Si(R.sup.1).sub.2, NR.sup.1, PR.sup.1, P(═O)R.sup.1, O, S, SO and SO.sub.2; R.sup.1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R.sup.2).sub.2, C(═O)R.sup.2, P(═O)(R.sup.2).sub.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, CN, NO.sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, OSO.sub.2R.sup.2, OH, COOR.sup.2, CON(R.sup.2).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, where the above-mentioned groups may each be substituted by one or more radicals R.sup.2 and where one or more CH.sub.2 groups in the above-mentioned groups is optionally replaced by Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, —O—, —S—, —COO— or —CONR.sup.2— and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO.sub.2, or 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.2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R.sup.2, or a combination of these systems, where two or more radicals R.sup.1 is optionally linked to one another and may form an aliphatic or aromatic ring; R.sup.2 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more substituents R.sup.2 here may also be linked to one another and form an aliphatic or aromatic ring; and k is equal to 2, 3, 4, 5 or 6.

17. The electronic device according to claim 16, wherein the compound of one of the formulae (I) to (IV) represents a compound of one of the formulae (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (IVa) and (IVb) ##STR00395## where the symbols occurring are as defined in claim 16 and furthermore: Ar.sup.1 and Ar.sup.2 are, identically or differently, an aryl group containing 6 to 60 aromatic ring atoms or a heteroaryl group containing 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R.sup.1; and R is optionally linked, analogously to the definition indicated in claim 16, to one or more radicals R.sup.0 and/or an adjacent group Ar.sup.1 or Ar.sup.2 via a single bond or via a divalent group Y.

18. The electronic device according to claim 16, wherein that the compound of one of the formulae (I) to (IV) represents a compound of one of the formulae (Ic), (IIc), (IIIc) and (IVc) ##STR00396## where the symbols occurring are as defined in claim 16 and furthermore: Ar.sup.1 and Ar.sup.2 are, identically or differently, an aryl group containing 6 to 60 aromatic ring atoms or a heteroaryl group containing 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R.sup.1; and R is optionally linked, analogously to the definition indicated in claim 16, to one or more adjacent groups Ar.sup.1 and Ar.sup.2 via a single bond or via a divalent group Y.

19. The electronic device according to claim 16, wherein the radical R represents an aryl or heteroaryl group having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.1, or represents an aralkyl or heteroaralkyl group having 5 to 20 aromatic ring atoms, which is optionally substituted by one or more radicals R.sup.1, where the radical R may furthermore be linked to one of the groups Ar.sup.1 and Ar.sup.2 via a single bond or via a divalent group Y.

20. The electronic device according to claim 16, wherein k is equal to 2 or 3.

21. The electronic device according to claim 16, wherein the compound of one of the formulae (I) to (IV) represents a compound of one of the formulae (IX-1) to (IX-3) and (X-1) ##STR00397## where the symbols occurring are as defined in claim 16 and furthermore Z is on each occurrence, identically or differently, CR.sup.1 or N, where not more than two adjacent groups Z may simultaneously be equal to N.

22. The electronic device according to claim 16, wherein the device is an organic integrated circuit (O-IC), organic field-effect transistor (O-FET), organic thin-film transistor (O-TFT), organic light-emitting transistor (O-LET), organic solar cell (O-SC), organic optical detector, organic photoreceptor, organic field-quench device (O-FQD), light-emitting electrochemical cell (LEC), organic laser diode (O-laser) and organic electroluminescent device (OLED).

23. The electronic device according to claim 22, wherein the device is an OLED.

24. The electronic device according to claim 16, wherein the compound of one of the formulae (I) to (IV) is employed as hole-transport material in a hole-transport layer or hole-injection layer and/or is employed as matrix material in an emitting layer.

25. A compound of one of the formulae (Ic) to (IVc) ##STR00398## wherein Ar.sup.1 and Ar.sup.2 are, identically or differently, an aryl group containing 6 to 60 aromatic ring atoms or a heteroaryl group containing 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R.sup.1; and R is an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.1, or an aralkyl or heteroaralkyl group having 5 to 20 aromatic ring atoms, which may be substituted by one or more radicals R.sup.1, where the radical R may furthermore be linked to an adjacent group Ar.sup.1 or Ar.sup.2 via a single bond or via a divalent group Y; X is a single bond; L is a divalent, or in the case of k=3, 4, 5 or 6 a tri-, tetra-, penta- or hexavalent group respectively, selected from C═O, C═NR.sup.1, Si(R.sup.1).sub.2, P(═O)(R.sup.1), SO, SO.sub.2, alkylene groups having 1 to 20 C atoms, alkenylene or alkynylene groups having 2 to 20 C atoms, where, in the case of the groups mentioned, one or more CH.sub.2 groups is optionally replaced by Si(R.sup.1).sub.2, O, S, C═O, C═NR.sup.1, C═O—O, C═O—NR.sup.1, NR.sup.1, P(═O)(R.sup.1), SO or SO.sub.2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO.sub.2, aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which is optionally substituted by one or more radicals R.sup.1, and any desired combinations of 1, 2, 3, 4 or 5 identical or different groups selected from the above-mentioned groups; or L is a single bond, where k in this case must be equal to 2; Y is on each occurrence, identically or differently, a divalent group selected from C═O, C═S, C═NR.sup.1, C(R.sup.1).sub.2, Si(R.sup.1).sub.2, NR.sup.1, PR.sup.1, P(═O)R.sup.1, O, S, SO and SO.sub.2; R.sup.1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R.sup.2).sub.2, C(═O)R.sup.2, P(═O)(R.sup.2).sub.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, CN, NO.sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, OSO.sub.2R.sup.2, OH, COOR.sup.2, CON(R.sup.2).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, where the above-mentioned groups may each be substituted by one or more radicals R.sup.2 and where one or more CH.sub.2 groups in the above-mentioned groups is optionally replaced by Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, —O—, —S—, —COO— or —CONR.sup.2— and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F, Cl, Br, I, CN or NO.sub.2, or 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.2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R.sup.2, or a combination of these systems, where two or more radicals R.sup.1 is optionally linked to one another and may form an aliphatic or aromatic ring; R.sup.2 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more substituents R.sup.2 here may also be linked to one another and form an aliphatic or aromatic ring; and k is equal to 2, 3, 4, 5 or 6.

26. An oligomer, polymer or dendrimer comprising one or more compounds according to claim 25, where the bond(s) to the polymer, oligomer or dendrimer may be localised at any position substituted by R or R.sup.1 in formula (Ic) to (IVc).

27. A formulation comprising at least one compound according to claim 25 and at least one solvent.

28. A formulation comprising at least one polymer, oligomer or dendrimer according to claim 26 and at least one solvent.

29. A process for the preparation of the compound of the formula (Ic) to (IVc) according to the invention according to claim 25, which comprises at least one of the two steps a) and b) indicated below is carried out: a) deprotonation at the 5- or 6-N atom of the benzimidazoquinazoline skeleton and subsequent reaction with an electrophilic compound, so that a bond is formed between the 5- or 6-N atom and the electrophilic compound; b) organometallic coupling under Hartwig-Buchwald or Ullmann conditions between the 5- or 6-N atom of the benzimidazoquinazoline skeleton and an aryl group Ar, which is employed as starting material Ar-Hal, where Hal is any suitable leaving group.

30. An electronic device which comprises the compound according to claim 25.

31. An organic electroluminescent device which comprises the compound according to claim 25.

32. An electronic device which comprises the at least one polymer, oligomer or dendrimer according to claim 26.

33. An organic electroluminescent device which comprises the compound according to claim at least one polymer, oligomer or dendrimer according to claim 26.

34. An organic electroluminescent device which comprises the compound according to claim 25 as hole-transport material, as matrix material, as emitter material, as electron-blocking material, as hole-injection material, as hole-blocking material and/or as electron-transport material.

35. An organic electroluminescent device which comprises said at least one polymer, oligomer or dendrimer as claimed in claim 26 as a hole-transport material, as matrix material, as emitter material, as electron-blocking material, as hole-injection material, as hole-blocking material and/or as electron-transport material.

Description

USE EXAMPLES

A) SYNTHESIS EXAMPLES

[0157] The following syntheses are carried out, unless indicated otherwise, under a protective-gas atmosphere in dried solvents. The solvents and reagents can be purchased from ALDRICH or ABCR. Benzimidazo[2,1-b]guinazolin-12(6H)-one [4149-00-2] was prepared in accordance with SU 1182043, 6,12-dihydrobenzimidazo[2,1-b]quinazoline [32675-34-6] was prepared in accordance with W. H. W. Lumm et al., J. Org. Chem. 1972, 37, 4, 607 and 5H-benzimidazo[1,2-a]benzimidazole [28890-99-5] was prepared in accordance with A. Reddouane et al., Bull, Soc. Chim. Beiges 96, 10, 787, 1987.

Example 1

Matrix M1

[0158] ##STR00360##

[0159] A mixture of 23.5 g (100 mmol) of benzimidazo[2,1-b]quinazolin-12(6H)-one, 34.0 g (110 mmol) of 1-bromo-3,5-diphenylbenzene [103068-20-8], 20.7 g (150 mmol) of potassium carbonate, 3.8 g (20 mmol) of copper iodide, 200 g of glass beads (diameter 3 mm) and 300 ml of NMP is heated at 200° C. for 20 h with vigorous stirring. After cooling, a mixture of 200 ml of water and 200 ml of ethanol is added, the mixture is stirred for a further 30 min., the suspension is filtered through a slotted frit in order to separate off the glass beads, the solid is then filtered off with suction, washed three times with 100 ml of ethanol each time and dried in vacuo. The solid is subjected to continuous hot extraction with o-xylene through an aluminium oxide bed (aluminium oxide, basic, activity grade 1), subsequently recrystallised five times from NMP and three times from o-dichlorobenzene and then subjected to fractional sublimation in vacuo (pressure about 10.sup.−5 mbar, temperature about 320° C.). Yield: 21.3 g (46 mmol), 46%; purity: 99.9% according to HPLC.

[0160] The following compounds are prepared analogously:

TABLE-US-00005 Ex. Bromide Product Yield 2 [00361] [00362] 46% 3 [00363] [00364] 45% 4 [00365] [00366] 38% 5 [00367] [00368] 52% 6 [00369] [00370] 36% 7 [00371] [00372] 44% 8 [00373] [00374] 28%

Example 9

Matrix M9

[0161] ##STR00375##

[0162] A suspension of 23.5 g (100 mmol) of benzimidazo[2,1-b]quinazolin-12(6H)-one, 2.6 g (110 mmol) of sodium hydride and 29,4 g (110 mmol) of 1-chloro-3,5-diphenyltriazine [3842-55-5] in 300 ml of DMF is stirred at 120° C. for 16 h. After cooling, 100 ml of ethanol are added dropwise, and 100 ml of water are then added, the solid is filtered off with suction, washed three times with 100 ml of a mixture of ethanol/water (1:1, vv) each time, three times with 100 ml of ethanol each time and then dried in vacuo. After recrystallisation of the solid three times from NMP, the product is recrystallised a further seven times from o-dichlorobenzene and then subjected to fractional sublimation in vacuo (pressure about 10.sup.−5 mbar, temperature about 340° C.). Yield: 30.2 g (67 mmol), 67%; purity: 99.9% according to HPLC.

[0163] The following compounds are prepared analogously:

TABLE-US-00006 Ex. Diazine/triazine Product Yield 10 [00376] [00377] 59% 11 [00378] [00379] 63%

Example 12

Hole Conductor HTM 12

[0164] ##STR00380##

[0165] 7.6 g (200 mmol) of lithium aluminium hydride are added in portions to a vigorously stirred suspension, cooled to 0° C., of 46.4 g (100 mmol) of 6-[1,1;3′,1″]-terphenyl-5′-yl-6,12-dihydrobenzimidazo[2,1-b]quinazoline (Ex. 1) in 1000 ml of diethylene glycol dimethyl ether. The reaction mixture is allowed to warm slowly to room temperature over the course of 4 h and is then stirred for a further 12 h. A mixture of 7.6 ml of water and 50 ml of diethylene glycol dimethyl ether, 7.6 ml of NaOH solution (10% by weight) and then 23.0 ml of water is added dropwise to the reaction mixture with vigorous stirring. The salts are filtered off with suction, rinsed with 100 ml of diethylene glycol dimethyl ether and removed in vacuo. After recrystallisation of the solid five times from NMP, the product is subjected to fractional sublimation in vacuo (pressure about 10.sup.−5 mbar, temperature about 320° C.). Yield: 17.5 g (39 mmol), 39%; purity: 99.9% according to HPLC.

[0166] The following compounds are prepared analogously:

TABLE-US-00007 Ex. Benzimidazo[2,1-b]-quinazolin-12(6H)-one Product Yield 13 [00381] [00382] 46% 14 [00383] [00384] 45%

EXAMPLE 15

Hole Conductor HTM 15

[0167] ##STR00385##

[0168] A mixture of 20.7 g (100 mmol) of 5H-benzimidazo[1,2-a]benzimidazole, 34.0 g (110 mmol) of 1-bromo-3,5-diphenylbenzene [103068-20-8], 20.7 g (150 mmol) of potassium carbonate, 3.8 g (20 mmol) of copper iodide, 200 g of glass beads (diameter 3 mm) and 300 ml of NMP is heated at 200° C. for 20 h with vigorous stirring. After cooling, a mixture of 200 ml of water and 200 ml of ethanol is added, the mixture is stirred for a further 30 min., the suspension is filtered through a slotted frit in order to separate off the glass beads, the solid is then filtered off with suction, washed three times with 100 ml of ethanol each time and dried in vacuo. The solid is subjected to continuous hot extraction with o-xylene through an aluminium oxide bed (aluminium oxide, basic, activity grade 1), subsequently recrystallised twice from NMP and five times from o-dichlorobenzene and then subjected to fractional sublimation in vacuo (pressure about 10.sup.−5 mbar, temperature about 310° C.). Yield: 9.6 g (22 mmol), 22%; purity: 99.9% according to HPLC.

B) DEVICE EXAMPLES

Example 16

Production of OlEDs

[0169] OLEDs according to the invention and OLEDs in accordance with the prior art are produced by a general process in accordance with WO 04/058911, which is adapted to the circumstances described here (layer-thickness variation, materials used).

[0170] The results for various OLEDs are presented in Examples 17 to 35 below (see Tables 1, 2 and 3). Glass plates which have been coated with structured ITO (indium tin oxide) in a thickness of 150 nm are coated with 20 nm of PEDOT (poly(3,4-ethylenedioxy-2,5-thiophene), applied by spin coating from water, purchased from H. C. Starck, Goslar, Germany) for improved processing. These coated glass plates form the substrates to which the OLEDs are applied. The OLEDs have in principle the following layer structure: substrate/hole-injection layer (HIL1, comprising HIL1, 20 nm)/hole-transport layer (HTL, comprising HTM1 (reference) or the HTMs according to the invention, 20 nm)/electron-blocking layer (EBL, 20 nm)/emission layer (EML comprising matrix materials M1 to M11 M according to the invention, 40 nm)/electron-transport layer (ETL, comprising ETL1, 20 nm)/electron-injection layer (EIL, comprising LiF, 1 nm) and finally a cathode. The cathode is formed by an aluminium layer with a thickness of 100 nm. The precise structure of the OLEDs, in particular the structure of the hole-conductor or emitter layer, and the results obtained with these OLEDs on use of the compounds according to the invention as matrix materials for phosphorescent emitters is shown in Table 1 for green-emitting OLEDs and in Table 2 for blue-emitting OLEDs. Table 3 shows the results for the use of compounds according to the invention both as matrix materials for phosphorescent emitters and also as hole-transport materials.

[0171] The materials used for the production of the OLEDs are shown in Table 4.

[0172] 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) and an emitting dopant (dopant, emitter), with which the matrix material or matrix materials is admixed in a certain proportion by volume by co-evaporation.

[0173] The as yet unoptimised OLEDs are characterised by standard methods. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd/A) and the voltage are determined. The efficiencies and voltages indicated in the tables relate to the corresponding values at an operating luminance of 1000 cd/m.sup.2.

TABLE-US-00008 TABLE 1 Green-emitting OLEDs Ex. EML Efficiency [cd/A] Voltage [V] CIE, x/y 17 M1: TEG1 (15%) 41.2 4.8 0.33/0.62 18 M2: TEG1 (15%) 37.9 4.7 0.33/0.62 19 M3: TEG1 (15%) 44.0 4.8 0.33/0.62 20 M4: TEG2 (15%) 52.0 4.5 0.32/0.61 21 M5: TEG2 (15%) 55.3 4.4 0.32/0.61 22 M6: TEG2 (15%) 48.0 4.4 0.32/0.61 23 M7: TEG2 (15%) 45.5 4.3 0.32/0.61 24 M8: TEG2 (15%) 34.6 4.5 0.32/0.61 25 M9: TEG2 (15%) 50.0 4.3 0.36/0.58 26 M10: TEG2 (15%) 45.0 4.1 0.36/0.58 27 M11: TEG2 (15%) 52.7 4.2 0.36/0.58

TABLE-US-00009 TABLE 2 Blue-emitting OLEDs Ex. EML Efficiency [cd/A] Voltage [V] CIE, x/y 28 M1: TEB1 (15%) 22.4 6.8 0.16/0.26 29 M5: TEB1 (15%) 24.0 6.6 0.16/0.27 30 M1: TEB2 (15%) 32.3 4.9 0.17/0.38 31 M5: TEB2 (15%) 28.1 4.8 0.17/0.38

TABLE-US-00010 TABLE 3 Green-emitting OLEDs Ex. HTM/EML Efficiency [cd/A] Voltage [V] CIE, x/y 32 HTM12/ 48.3 4.4 0.32/0.61 M6: TEG2 (15%) 33 HTM13/ 52.1 4.3 0.32/0.61 M6: TEG2 (15%) 34 HTM14/ 53.0 4.3 0.32/0.61 M6: TEG2 (15%) 35 HTM15/ 46.7 4.1 0.32/0.61 M6: TEG2 (15%)

TABLE-US-00011 TABLE 4 Structural formulae of the materials used [00386] [515834-67-0] HIL1 [00387] [123847-85-8] HTM1 (NPB) [00388] DE 102008056688.8 EBL [00389] [2085-33-8] ETM1 (Alq) [00390] [94928-86-6] TEG1 [00391] [359014-71-4] TEG2 [00392] [613682-85-2] TEB1 [00393] DE 102009007038.9 TEB2

[0174] As is clearly evident from the examples shown above, the materials according to the invention are particularly suitable for use as matrix materials for phosphorescent emitters and as hole conductors, where they result in high efficiencies and low operating voltages.