MATERIALS FOR ELECTRONIC DEVICES

Abstract

The invention relates to heteroaromatic, polycyclic condensed compounds according to the formulae (i) and (ii) defined below. Said compounds are suitable for use in electronic devices.

Claims

1.-22. (canceled)

23. A compound of formula (I) or (II) ##STR00628## where the variables that occur are as follows: Z, when no Ar.sup.1 unit binds thereto, is the same or different at each instance and is selected from CR.sup.1 and N; and Z, when an Ar.sup.1 unit binds thereto, is C; Ar.sup.1 is the same or different at each instance and is selected from a single bond, aromatic ring system which has 6 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, dibenzothiophene which may be substituted by one or more R.sup.2 radicals, and dibenzofuran which may be substituted by one or more R.sup.1 radicals; Ar.sup.2 is the same or different at each instance and is a group of formula (Ar.sup.2) ##STR00629## Y is the same or different at each instance and is selected from O, S, C(R.sup.3).sub.2, Si(R.sup.3).sub.2, ##STR00630## where, in the formulae ##STR00631## the free bonds are the bonds proceeding from the Y group to the rest of the group of the formula (Ar.sup.2); V is the same or different at each instance and is CR.sup.3 or N if the bond to the rest of the formula is not at the position in question, and V is C if the bond to the rest of the formula is at the position in question; where one or more pairs V-V may each be replaced by a unit selected from the following units: ##STR00632## where the free bonds indicate the bonds to the rest of the formula, and where T is the same or different at each instance and is CR.sup.3 or N if the bond to the rest of the formula is not at the position in question, and where T is C if the bond to the rest of the formula is at the position in question; R.sup.1, R.sup.2 are the same or different at each instance and are selected from H, D, F, C(═O)R.sup.4, CN, Si(R.sup.4).sub.3, P(═O)(R.sup.4).sub.2, OR.sup.4, S(═O)R.sup.4, S(═O).sub.2R.sup.4, 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.1 or 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 may each be substituted by one or more R.sup.4 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.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—, P(═O)(R.sup.4), —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, C(═O)R.sup.4, CN, Si(R.sup.4).sub.3, P(═O)(R.sup.4).sub.2, OR.sup.4, S(═O)R.sup.4, S(═O).sub.2R.sup.4, 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, heteroaromatic N-free ring systems having 5 to 40 aromatic ring atoms; and electron-deficient heteroaryl groups having 6 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 N-free ring systems and electron-deficient heteroaryl groups mentioned may each be substituted by one or more R.sup.4 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.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—, P(═O)(R.sup.4), —O—, —S—, SO or SO.sub.2; R.sup.4 is the same or different at each instance and is selected from H, D, F, C(═O)R.sup.5, CN, Si(R.sup.5).sub.3, P(═O)(R.sup.5).sub.2, OR.sup.5, S(═O)R.sup.5, S(═O).sub.2R.sup.5, 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.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 may each be substituted by one or more R.sup.5 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.5C═CR.sup.5—, —C≡C—, Si(R.sup.5).sub.2, C═O, C═NR.sup.5, —C(═O)O—, —C(═O)NR.sup.5—, P(═O)(R.sup.5), —O—, —S—, SO or SO.sub.2; R.sup.5 is the same or different at each instance and is selected from H, D, F, 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 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; a, b, c, d, e are the same or different and are selected from 1, 2, 3 and 4.

24. The compound as claimed in 23, wherein, for every six-membered ring in one unit ##STR00633## in the formulae (I) and (II), not more than one Z group is N.

25. The compound as claimed in 23, wherein Ar.sup.1 is the same or different at each instance and is selected from a single bond and the formulae: ##STR00634## ##STR00635## ##STR00636## ##STR00637## ##STR00638## ##STR00639## ##STR00640## ##STR00641## ##STR00642## ##STR00643## where the formulae may each be substituted by one or more R.sup.2 radicals.

26. The compound as claimed in 23, wherein Y is the same or different at each instance and is selected from O and S.

27. The compound as claimed in 23, wherein Ar.sup.2 conforms to a formula selected from the following formulae: ##STR00644## ##STR00645## where the free bond denotes the bond to the rest of the formula.

28. The compound as claimed in 23, wherein R.sup.1 is the same or different at each instance and is selected from H, D, F, CN, aromatic ring systems which have 6 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals.

29. The compound as claimed in 23, wherein R.sup.2 is the same or different at each instance and is selected from H, D, F, CN, aromatic ring systems which have 6 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals.

30. The compound as claimed in 23, wherein R.sup.3 is the same or different at each instance and is selected from H, D, F, CN, aromatic ring systems which have 6 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, and electron-deficient heteroaryl groups which have 6 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals.

31. The compound as claimed in 23, wherein R.sup.4 is the same or different at each instance and is selected from H, D, F, CN, Si(R.sup.5).sub.3, 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, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl and alkoxy groups mentioned, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned may each be substituted by one or more R.sup.5 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups mentioned may be replaced by —C≡C—, —R.sup.5C═CR.sup.5—, Si(R.sup.5).sub.2, C═O, C═NR.sup.5, —O—, —S—, —C(═O)O— or —C(═O)NR.sup.5—.

32. The compound as claimed in 23, wherein a=1 and b=1; or characterized in that a=1 and b=2, where the two Ar.sup.2 groups chosen are the same or different.

33. The compound as claimed in 23, wherein c=1, e=1 and d=1; or characterized in that c=1, e=1 and d=2, where the two Ar.sup.2 groups chosen are the same or different.

34. The compound as claimed in 23, wherein compound conforms to one of the formulae (I-A-1), (I-A-2), (I-A-3), (II-A-1) and (II-A-2) ##STR00646## where the groups that occur are as defined in claim 23, except that Ar.sup.1 is not a single bond.

35. The compound as claimed in 25, wherein the compound conforms to one of the formulae (I-A-1), (I-A-2) and (I-A-3) ##STR00647## where Z is CR.sup.3, Ar.sup.1 is as defined in claim 25, Ar.sup.2 is conforms to a formula selected from the following formulae: ##STR00648## ##STR00649## where the free bond denotes the bond to the rest of the formula. R.sup.1 is the same or different at each instance and is selected from H, D, F, CN, aromatic ring systems which have 6 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, R.sup.2 is the same or different at each instance and is selected from H, D, F, CN, aromatic ring systems which have 6 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, R.sup.3 is the same or different at each instance and is selected from H, D, F, CN, aromatic ring systems which have 6 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, and electron-deficient heteroaryl groups which have 6 to 40 aromatic ring atoms and may each be substituted by one or more R.sup.4 radicals, and R.sup.4 is the same or different at each instance and is selected from H, D, F, CN, Si(R.sup.5).sub.3, 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, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl and alkoxy groups mentioned, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned may each be substituted by one or more R.sup.5 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups mentioned may be replaced by —C≡C—, —R.sup.5C═CR.sup.5—, Si(R.sup.5).sub.2, C═O, C═NR.sup.5, O, S, C(═O)O— or —C(═O)NR.sup.5—.

36. A process for preparing the compound as claimed in 23, which comprises converting a compound of the formula (Z) ##STR00650## where X.sup.1 is selected from B(OR.sup.4).sub.2, Cl, Br and I in a Suzuki reaction.

37. An oligomer, polymer or dendrimer comprising one or more compounds of formula (I) or (II) as claimed in claim 23, wherein the bond(s) to the polymer, oligomer or dendrimer may be localized at any desired positions substituted by R.sup.1, R.sup.2 or R.sup.3 in formula (I) or (II).

38. A formulation comprising the at least one compound as claimed in claim 23 and at least one solvent.

39. A formulation comprising the polymer, oligomer or dendrimer as claimed in claim 37 and at least one solvent.

40. An electronic device comprising at least one compound as claimed in claim 23.

41. An organic electroluminescent device which comprises at least one compound as claimed in claim 23, is present as matrix material in an emitting layer together with at least one phosphorescent emitting compound and at least one further matrix material.

42. The device as claimed in claim 41, wherein the further matrix material is selected from bipolar matrix materials.

43. The electronic device as claimed in claim 41, wherein the further matrix material is selected from compounds of the formulae (BP-1) and (BP-2) ##STR00651## where the variables that occur are as follows: V is O or S; Ar, Ar.sub.1, Ar.sub.2 at each instance are each independently an aryl or heteroaryl group which has 5 to 40 ring atoms and may be substituted by one or more R.sub.3 radicals or an aromatic or heteroaromatic ring system which has 6 to 40 ring atoms and may be substituted by one or more R.sub.3 radicals; p, q are each independently 0, 1, 2, 3 or 4; s, r are each independently 0, 1, 2, 3 or 4; R is the same or different at each instance and is selected from the group consisting of D, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sub.2).sub.2, C(═O)Ar, C(═O)R.sub.2, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, Si(Ar).sub.3, Si(R.sub.2).sub.3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sub.2C═CR.sub.2, Si(R.sub.2).sub.2, C═O, C═S, C═NR.sub.2, P(═O)(R.sub.2), SO, SO.sub.2, NR.sub.2, O, S or CONR.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system which has 5 to 40 ring atoms and may be substituted in each case by one or more R.sub.2 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 ring atoms and may be substituted by one or more R.sub.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 ring atoms and may be substituted by one or more R.sub.2 radicals; at the same time, it is possible for a maximum of one substituent R together with Ar.sub.1 to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sub.2 radicals; R2 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, NH.sub.2, N(R.sub.3).sub.2, C(═O)Ar, C(═O)H, C(═O)R.sub.3, P(═O)(Ar).sub.2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R.sub.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by HC═CH, R.sub.3C═CR.sub.3, C≡C, Si(R.sub.3).sub.2, Ge(R.sub.3).sub.2, Sn(R.sub.3).sub.2, C═O, C═S, C═Se, C═NR.sub.3, P(═O)(R.sub.3), SO, SO.sub.2, NH, NR.sub.3, O, S, CONH or CONR.sub.3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system which has 5 to 60 ring atoms and may be substituted in each case by one or more R.sub.3 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 ring atoms and may be substituted by one or more R.sub.3 radicals, or a combination of these systems, where it is optionally possible for two or more adjacent substituents R.sub.2 to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sub.3 radicals; R.sub.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, it is possible for two or more adjacent substituents R.sub.3 together to form a mono- or polycyclic, aliphatic ring system.

44. A mixture comprising at least one compound as claimed in claim 23 and at least one further compound selected from bipolar matrix materials.

Description

EXAMPLES

A) Synthesis Examples

Step a: Synthesis of Intermediates

Example a: 10-(4-Bromophenyl)benzo[h]quinoline

[0125] ##STR00381##

[0126] 15.47 g (75 mmol) of 4-bromobenzeneboronic acid, 19.4 g of 10-bromobenzo[h]quinoline (75 mmol) and 110 ml of an aqueous 2M NaHCO.sub.3 solution (163 mmol) are suspended in 500 ml of dimethoxyethane. 3.0 g (3.45 mmol) of tetrakis(triphenylphosphine)palladium(0) is added to this suspension, and the reaction mixture is heated under reflux for 22 h. After cooling, the organic phase is removed, filtered through silica gel, washed four times with 400 ml of water and then concentrated to dryness. After filtration of the crude product through silica gel with heptane/toluene (10:1), 39 g (71%) of 10-(4-bromophenyl)benzo[h]quinoline is obtained.

[0127] The following compounds are prepared in an analogous manner:

TABLE-US-00007 Reactant 1 Reactant 2 Product Yield 1a [00382] [00383] [00384] 58% 2a [00385] [00386] [00387] 49% 3a [00388] [00389] [00390] 51% 4a [00391] [00392] [00393] 56% 5a [00394] [00395] [00396] 43% 6a [00397] [00398] [00399] 54% 7a [00400] [00401] [00402] 49% 8a [00403] [00404] [00405] 52% 9a [00406] [00407] [00408] 66% 10a [00409] [00410] [00411] 71% 11a [00412] [00413] [00414] 68% 12a [00415] [00416] [00417] 75% 13a [00418] [00419] [00420] 70%

Step b: Synthesis of Compounds of the Invention

Example b: 10-(4-Dibenzothiophen-4-ylphenyl)benzo[h]quinoline

[0128] ##STR00421##

[0129] The following compounds are prepared under conditions analogous to those in example 1:

TABLE-US-00008 Reactant 1 Reactant 2 Product Yield 1b [00422] [00423] [00424] 67% 2b [00425] [00426] [00427] 68% 3b [00428] [00429] [00430] 60% 4b [00431] [00432] [00433] 72% 5b [00434] [00435] [00436] 65% 6b [00437] [00438] [00439] 74% 7b [00440] [00441] [00442] 73% 8b [00443] [00444] [00445] 80% 9b [00446] [00447] [00448] 82% 10b [00449] [00450] [00451] 73% 11b [00452] [00453] [00454] 70% 12b [00455] [00456] [00457] 72% 13b [00458] [00459] [00460] 69% 14b [00461] [00462] [00463] 66% 15b [00464] [00465] [00466] 75% 16b [00467] [00468] [00469] 65% 17b [00470] [00471] [00472] 63% 18b [00473] [00474] [00475] 81% 19b [00476] [00477] [00478] 84% 20b [00479] [00480] [00481] 80% 21b [00482] [00483] [00484] 78% 22b [00485] [00486] [00487] 71% 23b [00488] [00489] [00490] 82% 24b [00491] [00492] [00493] 80%

Step c: Synthesis of Compounds of the Invention

Example c: 10-(4-Biphenyl-4-yldibenzofuran-1-yl)benzo[h]quinoline

[0130] ##STR00494##

[0131] Under conditions analogous to those in example c, the following compounds are prepared proceeding from 10-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzo[h]quinoline:

TABLE-US-00009 Reactant 1 Reactant 2 Product Yield 1c [00495] [00496] [00497] 86% 2c [00498] [00499] [00500] 81% 3c [00501] [00502] [00503] 80% 4c [00504] [00505] [00506] 79% 5c [00507] [00508] [00509] 77% 6c [00510] [00511] [00512] 82% 7c [00513] [00514] [00515] 81% 8c [00516] [00517] [00518] 60% 9c [00519] [00520] [00521] 62% 10c [00522] [00523] [00524] 66% 11c [00525] [00526] [00527] 78% 12c [00528] [00529] [00530] 65% 13c [00531] [00532] [00533] 69% 14c [00534] [00535] [00536] 54% 15c [00537] [00538] [00539] 87% 16c [00540] [00541] [00542] 82% 17c [00543] [00544] [00545] 75% 18c [00546] [00547] [00548] 80% 19c [00549] [00550] [00551] 78% 20c [00552] [00553] [00554] 45% 21c [00555] [00556] [00557] 62% 22c [00558] [00559] [00560] 46% 23c [00561] [00562] [00563] 82% 24c [00564] [00565] [00566] 76% 25c [00567] [00568] [00569] 73% 26c [00570] [00571] [00572] 60% 27c [00573] [00574] [00575] 64% 28c [00576] [00577] [00578] 83% 29c [00579] [00580] [00581] 80% 30c [00582] [00583] [00584] 86% 31c [00585] [00586] [00587] 87% 32c [00588] [00589] [00590] 80% 33c [00591] [00592] [00593] 79% 34c [00594] [00595] [00596] 83% 35c [00597] [00598] [00599] 67% 36c [00600] [00601] [00602] 75% 37c [00603] [00604] [00605] 79% 38c [00606] [00607] [00608] 80% 39c [00609] [00610] [00611] 83% 40c [00612] [00613] [00614] 82%

B) Production and Characterization of OLEDs

[0132] Glass plaques coated with structured ITO (indium tin oxide) of thickness 50 nm are treated prior to coating with an oxygen plasma, followed by an argon plasma. These plasma-treated glass plaques form the substrates to which the OLEDs are applied.

[0133] The OLEDs have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL)/electron blocker layer (EBL)/emission layer (EML)/hole blocker layer (HBL)/electron transport layer (ETL)/electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminum layer of thickness 100 nm. The exact structure of the OLEDs can be found in table 1. The materials required for production of the OLEDs are shown in table 2. The data of the OLEDs are listed in table 3.

[0134] All materials are applied by thermal vapor deposition in a vacuum chamber. In this case, the emission layer always consists of at least one matrix material (host material) and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by coevaporation. In the case of mixed layers, data in such a form as IC1:1b:TEG1 (40%:40%:10%) mean that the material IC1 is present in the layer in a proportion by volume of 40%, 1b in a proportion by volume of 40%, and TEG1 in a proportion by volume of 10%.

[0135] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the operating voltage, the current efficiency (CE, measured in cd/A) and the external quantum efficiency (EQE, measured in %) are determined as a function of luminance, calculated from current-voltage-luminance characteristics assuming Lambertian emission characteristics. The electroluminescence spectra are determined at a luminance of 1000 cd/m.sup.2, and the CIE 1931 x and y color coordinates are calculated therefrom. The parameter U1000 in table 3 refers to the voltage which is required for a luminance of 1000 cd/m.sup.2. CE1000 and EQE1000 respectively denote the current efficiency and external quantum efficiency that are attained at 1000 cd/m.sup.2.

[0136] The materials of the invention can be used in green-phosphorescing emission layers of OLEDs, as shown by the following examples:

TABLE-US-00010 TABLE 1 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex. thickness thickness thickness thickness thickness thickness thickness E1 HATCN SpMA1 SpMA2 IC1:1b:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 1 nm 5 nm 230 nm 20 nm (58%:30%:12%) 40 nm 5 nm 30 nm E2 HATCN SpMA1 SpMA2 IC1:7b:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 1 nm 5 nm 230 nm 20 nm (58%:30%:12%) 40 nm 5 nm 30 nm E3 HATCN SpMA1 SpMA2 IC1:11b:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 1 nm 5 nm 230 nm 20 nm (58%:30%:12%) 40 nm 5 nm 30 nm E4 HATCN SpMA1 SpMA2 IC1:30c:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 1 nm 5 nm 230 nm 20 nm (58%:30%:12%) 40 nm 5 nm 30 nm E5 HATCN SpMA1 SpMA2 IC1:32c:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 1 nm 5 nm 230 nm 20 nm (58%:30%:12%) 40 nm 5 nm 30 nm E6 HATCN SpMA1 SpMA2 IC1:34c:TEG1 ST2 ST2:LiQ (50%:50%) LiQ 1 nm 5 nm 230 nm 20 nm (58%:30%:12%) 40 nm 5 nm 30 nm

TABLE-US-00011 TABLE 2 Materials used [00615] [00616] [00617] [00618] [00619] [00620] [00621] [00622] [00623] [00624] [00625] [00626] [00627]

TABLE-US-00012 TABLE 3 Data of the OLEDs U1000 SE1000 EQE 1000 CIE x/y at Ex. (V) (cd/A) (%) 1000 cd/m.sup.2 E1 3.4 62 17 0.32/0.62 E2 3.7 62 17 0.32/0.62 E3 3.7 56 16 0.32/0.62 E4 3.6 57 16 0.32/0.62 E5 3.6 59 17 0.32/0.62 E6 3.7 55 16 0.32/0.62

[0137] The data obtained show that the compounds of the application can be used in OLEDs. More particularly, the OLED use examples adduced above show high efficiency and low operating voltage.

[0138] It is also possible to use compounds 2b-6b, 8b-10b, 12b-24b, 1c-29c, 31c, 33c and 35c-40c, the synthesis of which is detailed above in part A, to obtain OLEDs having good efficiency and low operating voltage.