MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

Abstract

The present invention describes dibenzofuran derivatives substituted by electron-deficient heteroaryl groups, and electronic devices, especially organic electroluminescent devices, comprising these compounds as triplet matrix materials.

Claims

1.-14. (canceled)

15. A compound of formula (1) ##STR00627## where the symbols used are as follows: Y is O or S; Z is the same or different at each instance and is CR or N, with the proviso that at least two Z are N; Ar.sup.1 is the same or different at each instance and is an aromatic ring system which has 6 to 40 aromatic ring atoms and may be substituted by one or more R radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and which is bonded to the dibenzofuran or dibenzothiophene via a nitrogen atom and which may be substituted by one or more R radicals, or a dibenzofuran or dibenzothiophene group which may be substituted by one or more R radicals; Ar.sup.2 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R radicals; R is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar′).sub.2, N(R.sup.1).sub.2, OAr′, SAr′, CN, NO.sub.2, OR.sup.1, SR.sup.1, COOR.sup.1, C(═O)N(R.sup.1).sub.2, Si(R.sup.1).sub.3, B(OR.sup.1).sub.2, C(═O)R.sup.1, P(═O)(R.sup.1).sub.2, S(═O)R.sup.1, S(═O).sub.2R.sup.1, OSO.sub.2R.sup.1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.1 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.1).sub.2, C═O, NR.sup.1, O, S or CONR.sup.1, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and may be substituted in each case by one or more R.sup.1 radicals; at the same time, two R radicals together may also form a ring system; Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; at the same time, two Ar′ radicals bonded to the same nitrogen atom may also be bridged to one another by a single bond or a bridge selected from N(R.sup.1), C(R.sup.1).sub.2, 0 and S; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.2).sub.2, CN, NO.sub.2, OR.sup.2, SR.sup.2, Si(R.sup.2).sub.3, B(OR.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, OSO.sub.2R.sup.2, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.2).sub.2, C═O, NR.sup.2, O, S or CONR.sup.2 and where one or more hydrogen atoms in the alkyl, alkenyl or alkynyl group may be replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals; at the same time, two or more R.sup.1 radicals together may form an aliphatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; p, q are the same or different at each instance and are 0, 1, 2 or 3; r is 0, 1, 2, 3 or 4, with the proviso that r is not more than (4-j); s is 0, 1, 2 or 3, with the proviso that s is not more than (3-k); j, k are the same or different at each instance and are 0, 1, 2 or 3, with the proviso that j+k ≥1.

16. The compound according to claim 15, wherein all three Z groups are N, or in that two Z groups are N and the third Z group is CH.

17. The compound according to claim 15, wherein the compound is selected from the compounds of the formula (4) ##STR00628## where the symbols and indices used have the definitions given in claim 15.

18. The compound according to claim 15, wherein the compound is selected from the compounds of the formula (51 ##STR00629## where the symbols and indices used have the definitions given in claim 15.

19. The compound according to claim 15, wherein the compound is selected from the compounds of the formulae (6a) and (6b) ##STR00630## where the symbols and indices used have the definitions given above.

20. The compound according to claim 15, wherein the compound is selected from the compounds of the formulae (7a) and (7b) ##STR00631## where the symbols used have the definitions given in claim 15.

21. The compound according to claim 15, wherein, when j=1, the Ar.sup.1 group is bonded in the 7 or 8 position of the dibenzofuran or dibenzothiophene, and in that, when k=1, the Ar.sup.1 group is bonded in the 3 or 4 position of the dibenzofuran or dibenzothiophene.

22. The compound according to claim 15, wherein Ar.sup.2 is the same or different at each instance and represents an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R radicals.

23. The compound according to claim 15, wherein Ar.sup.1 is an aromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R radicals, or N-carbazolyl which may be substituted by one or more R radicals, or dibenzofuran or dibenzothiophene, each of which may be substituted by one or more R radicals.

24. A formulation comprising at least one compound according to claim 15 and at least one further compound and/or solvent.

25. An electronic device comprising at least one compound according to claim 15.

26. An organic electroluminescent device (OLED) comprising the compound according to claim 15 is used as matrix material for a phosphorescent emitter in an emitting layer.

27. An organic electroluminescent device (OLED) comprising the compound according to claim 15 is used in combination with a further matrix material for a phosphorescent emitter in an emitting layer, where the further matrix material is a compound of formula (9) ##STR00632## where R.sup.1, R.sup.2 and Ar′ have the definitions detailed in claim 15 and the further symbols and indices used are as follows: R.sub.A is H, -L.sup.3-Ar.sup.5 or -L.sup.1-N(Ar′).sub.2; R.sub.B is Ar.sup.4 or -L.sup.2-N(Ar′).sub.2; L.sup.1, L.sup.2 are the same or different at each instance and are a single bond or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; L.sup.3 is a single bond or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, where one substituent R.sup.1 may form a ring with a substituent R on the carbazole; Ar.sup.4 is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more R.sup.1 radicals; Ar.sup.5 is the same or different at each instance and is an unsubstituted or substituted 9-arylcarbazolyl or unsubstituted or substituted carbazol-9-yl, which may be substituted by one or more R.sup.1 radicals, and where one or more instances each of two R.sup.1 radicals or one R.sup.1 radical together with one R radical may independently form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring, where aryl is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by R.sup.1; u at each instance is independently 0, 1, 2 or 3; v at each instance is independently 0, 1, 2, 3 or 4.

Description

EXAMPLES

[0120] The syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere in dried solvents. The solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. The respective figures in square brackets or the numbers quoted for individual compounds relate to the CAS numbers of the compounds known from the literature.

[0121] Preparation of the Synthons:

[0122] S1:

##STR00341##

[0123] 2-(8-Chlorodibenzofuran-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [2140871-51-6] (32.86 g, 100.0 mmol), 2-chloro-4-dibenzofuran-3-yl-6-phenyl-1,3,5-triazine [2142681-84-1] (37.57 g, 105.0 mmol) and sodium carbonate (22.26 g, 210.0 mmol) are suspended in 600 ml of ethylene glycol dimethyl ether and 300 ml of water and inertized for 30 min. Subsequently, tri-o-tolylphosphine (913 mg, 3.0 mmol) and then palladium(II) acetate (112 mg, 0.5 mmol) are added, and the reaction mixture is heated under reflux for 20 h. After cooling, the precipitated solids are filtered off with suction and washed with ethanol. The crude product is recrystallized from m-xylene. Yield: 46.11 g (88 mmol, 88%) of solids, 98% by HPLC.

[0124] In an analogous manner, it is possible to prepare the compounds below. Purification can be effected using column chromatography, or recrystallization can be effected using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone etc.

TABLE-US-00001 Reactant 1 Reactant 2 [00342] [00343] [00344] [00345] [00346] [00347] [00348] [00349] [00350] [00351] [00352] [00353] Product Yield [00354] 85% [00355] 82% [00356] 91% [00357] 88% [00358] 78% [00359] 81%

[0125] S50:

##STR00360##

[0126] An initial charge of S1 (46.11 g, 88.0 mmol), bis(pinacolato)diboron [73183-34-3] (25.39 g, 100.0 mmol) and potassium acetate (28.82 g, 293.6 mmol) in 1,4-dioxane (700 ml) is inertized with argon for 2 min. Subsequently, XPhos [564483-18-7] (456 mg, 0.96 mmol) and Pd.sub.2(dba).sub.3 [51364-51-3] (435 mg, 0.48 mmol) are added and the reaction mixture is stirred under reflux for 26 h. After cooling, the solvent is removed by rotary evaporation and the residue is worked up by extraction with toluene/water. The organic phase is dried over Na.sub.2SO.sub.4 and concentrated to dryness by rotary evaporation. The residue is boiled under reflux with ethyl acetate for 2 h, and the solids are filtered off with suction and washed with ethyl acetate. Yield: 49.4 g (80.2 mmol, 91%) of solids; 97% by .sup.1H NMR.

[0127] In an analogous manner, it is possible to prepare the compounds below. Purification can be effected using column chromatography, or recrystallization can be effected using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone etc.

TABLE-US-00002 Reactant Product Yield [00361] [00362] 90% [00363] [00364] 88% [00365] [00366] 84% [00367] [00368] 80% [00369] [00370] 82% [00371] [00372] 79%

[0128] S100:

##STR00373##

[0129] Under inert atmosphere, 6-bromo-1-chlorodibenzofuran [2144800-21-3] (28.15 g, 100 mmol), 8H-[1]benzothieno-[2,3-c]carbazole [1255309-17-1] (28.70 g, 105 mmol) and sodium tert-butoxide (19.21 g, 200 mmol) were initially charged in 1000 ml of ortho-xylene. Subsequently, tri-tert-butylphosphine [13716-12-6] (1 mol/l solution in toluene, 5.0 ml, 5.0 mmol) and tris(dibenzylideneacetone)dipalladium [51364-51-3] (1.14 g, 1.25 mmol) are added one after the other, and the reaction mixture is heated under reflux for 16 h. The reaction mixture is cooled down to room temperature and worked up by extraction with toluene/water. The organic phases are combined and dried over Na.sub.2SO.sub.4, and the solvent is removed under reduced pressure on a rotary evaporator. The resultant solids are suspended in 300 ml of ethanol, stirred under reflux for 1 h and filtered off with suction. The crude product is recrystallized from ethyl acetate. Yield: 32.2 g (68 mmol, 68%) of solids, 97% by .sup.1H NMR.

[0130] In an analogous manner, it is possible to prepare the compounds below. Purification can be effected using column chromatography, or recrystallization can be effected using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone etc.

TABLE-US-00003 Reactant 1 Reactant 2 Product Yield [00374] [00375] [00376] 71% [00377] [00378] [00379] 34% [00380] [00381] [00382] 59%

[0131] S150:

##STR00383##

[0132] Under an inert atmosphere, an initial charge of 1-bromo-8-iododibenzofuran [1822311-11-4] (37.28 g, 100 mmol), 3-phenyl-9H-carbazole [103012-26-6] (16.71 g, 100 mmol) of potassium carbonate (34.55 g, 250 mmol), copper iodide (3.81 g, 20.0 mmol) and 1,3-di(2-pyridinyl)propane-1,3-dione (4.52 g, 20.0 mmol) in DMF (350 ml) are inertized with argon for a further 15 min and then stirred at 115° C. for 32 h.

[0133] The mixture is left to cool down to room temperature, filtered through a Celite bed and washed through twice with 200 ml of DMF, and the filtrate is concentrated to dryness on a rotary evaporator. The residue is worked up by extraction with dichloromethane/water, and the organic phase is washed twice with water and once with saturated NaCl solution and dried over Na.sub.2SO.sub.4. 150 ml of ethanol are added, dichloromethane is drawn off on a rotary evaporator down to 500 mbar, and the precipitated solids are filtered off with suction and washed with ethanol. Yield: 24.71 g (50.6 mmol, 51%) of grey solid; 95% by .sup.1H NMR.

[0134] In an analogous manner, it is possible to prepare the compounds below. Purification can be effected using column chromatography, or recrystallization can be effected using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone etc.

TABLE-US-00004 Reactant 1 Reactant 2 Product Yield [00384] [00385] [00386] 27% [00387] [00388] [00389] 57% [00390] [00391] [00392] 49% [00393] [00394] [00395] 51% [00396] [00397] [00398] 50% [00399] [00400] [00401] 61% [00402] [00403] [00404] 54% [00405] [00406] [00407] 46%

[0135] S200:

##STR00408##

[0136] To an initial charge of 8-bromodibenzofuran-1-yl trifluoromethanesulfonate [2247123-46-0] (47.00 g, 118.9 mmol), 4,4,5,5-tetramethyl-2-(2-triphenylenyl)-1,3,2-dioxaborolane (49.72 g, 140.4 mmol) and K.sub.2CO.sub.3 (32.88 g, 237.9 mmol) in a flask are added toluene (500 ml) and water (150 ml), and the mixture is inertized with argon for 30 min. Subsequently, Pd.sub.2(dba).sub.3 (545 mg, 0.59 mmol) and tri-ortho-tolylphosphine [6163-58-2] (724 mg, 2.38 mmol) are added and the mixture is heated under reflux for 24 h. After cooling, the precipitated solids are filtered off with suction and washed twice with ethanol. The crude product is extracted by stirring under reflux in ethanol for 2 h, and the solids are filtered off with suction after cooling. Yield: 58.8 g (108 mmol, 91%) of solids; purity 98% by .sup.1H NMR.

[0137] In an analogous manner, it is possible to prepare the compounds below. Purification can be effected using column chromatography, or recrystallization can be effected using standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone etc.

TABLE-US-00005 Reactant 1 Reactant 2 Product Yield [00409] [00410] [00411] 89% [00412] [00413] [00414] 92% [00415] [00416] [00417] 83% [00418] [00419] [00420] 91% [00421] [00422] [00423] 80% [00424] [00425] [00426] 82% [00427] [00428] [00429] 85% [00430] [00431] [00432] 77% [00433] [00434] [00435] 90%

[0138] Preparation of the Compounds of the Invention:

[0139] Synthesis of P1:

##STR00436##

[0140] To an initial charge of 2,4-diphenyl-6-[8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-dibenzofuranyl]-1,3,5-triazine [2138490-96-5] (15.31 g, 29.1 mmol), S200 (15.06 g, 27.8 mmol) and K.sub.3PO.sub.4 (12.17 g, 57.3 mmol) in a flask are added tetrahydrofuran (200 ml) and water (50 ml), and the mixture is inertized with argon for 30 min. Subsequently, Pd(OAc).sub.2 (124 mg, 0.55 mmol) and XPhos [564483-18-7] (556 mg, 1.11 mmol) are added and the mixture is heated under reflux for 24 h. After cooling, the precipitated solids are filtered off with suction and washed twice with water and twice with ethanol. The crude product is subjected to hot extraction with toluene/heptane (1:1) three times, then recrystallized three times from toluene and finally sublimed under high vacuum. Yield: 14.8 g (18.7 mmol, 67%); purity: >99.9% by HPLC

[0141] In an analogous manner, it is possible to prepare the compounds below. The catalyst system used here (palladium source and ligand) may also be Pd.sub.2(dba).sub.3 with SPhos [657408-07-6] or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Purification can also be effected using column chromatography, or recrystallization or hot extraction using other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, or recrystallization using high boilers such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

TABLE-US-00006 Reactant 1 Reactant 2 Product Yield [00437] [00438] [00439] 50% [00440] [00441] [00442] 48% [00443] [00444] [00445] 55% [00446] [00447] [00448] 57% [00449] [00450] [00451] 56% [00452] [00453] [00454] 63% [00455] [00456] [00457] 52% [00458] [00459] [00460] 55% [00461] [00462] [00463] 62% [00464] [00465] [00466] 49% [00467] [00468] [00469] 50% [00470] [00471] [00472] 60% [00473] [00474] [00475] 57% [00476] [00477] [00478] 45% [00479] [00480] [00481] 39% [00482] [00483] [00484] 60% [00485] [00486] [00487] 51% [00488] [00489] [00490] 55% [00491] [00492] [00493] 48% [00494] [00495] [00496] 51% [00497] [00498] [00499] 44% [00500] [00501] [00502] 44% [00503] [00504] [00505] 60% [00506] [00507] [00508] 53% [00509] [00510] [00511] 41% [00512] [00513] [00514] 42% [00515] [00516] [00517] 56% [00518] [00519] [00520] 45% [00521] [00522] [00523] 58% [00524] [00525] [00526] 50% [00527] [00528] [00529] 47% [00530] [00531] [00532] 50% [00533] [00534] [00535] 46% [00536] [00537] [00538] 44%

[0142] P100:

##STR00539##

[0143] To an initial charge of 2,4-diphenyl-6-[8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-dibenzofuranyl]-1,3,5-triazine [2138490-96-5] (15.31 g, 29.1 mmol), S150 (14.41 g, 29.5 mmol) and Na.sub.2CO.sub.3 (6.17 g, 58.2 mmol) in a flask are added toluene (300 ml) and water (100 ml), and the mixture is inertized with argon for 30 min. Subsequently, tetrakis(triphenylphosphine)palladium(0) [14221-01-3] (1.00 g, 0.87 mmol) is added and the mixture is heated under reflux for 36 h. After cooling, the reaction mixture is worked up by extraction with toluene and water, the combined organic phases are dried over Na.sub.2SO.sub.4, and the filtrate is concentrated to dryness by rotary evaporation. The residue is suspended in 350 ml of hot EtOH and stirred under reflux for 1 h, and the solids are filtered off with suction after cooling. The crude product is subjected to hot extraction with toluene/heptane (1:1) twice, then recrystallized three times from n-butyl acetate and finally sublimed under high vacuum. Yield: 14.8 g (18.7 mmol, 67%); purity: >99.9% by HPLC

[0144] In an analogous manner, it is possible to prepare the compounds below. The catalyst system used here, rather than tetrakis(triphenylphosphine)palladium(0), may also be Pd.sub.2(dba).sub.3 with SPhos [657408-07-6] (palladium source and ligand) or bis(triphenylphosphine)palladium(II) chloride [13965-03-2]. Purification can also be effected using column chromatography, or recrystallization or hot extraction using other standard solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, or recrystallization using high boilers such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.

TABLE-US-00007 Reactant 1 Reactant 2 Product Yield [00540] [00541] [00542] 60% [00543] [00544] [00545] 57% [00546] [00547] [00548] 62% [00549] [00550] [00551] 51% [00552] [00553] [00554] 52% [00555] [00556] [00557] 49% [00558] [00559] [00560] 52% [00561] [00562] [00563] 40% [00564] [00565] [00566] 37% [00567] [00568] [00569] 42%

Device Examples

[0145] Pretreatment for Examples V1-V5, E1-E28 and B1 to B54

[0146] Glass plaques coated with structured ITO (indium tin oxide) of thickness 50 nm are treated prior to coating, first with an oxygen plasma, followed by an argon plasma. These plasma-treated glass plaques form the substrates to which the OLEDs are applied.

[0147] The OLEDs basically have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL)/electron blocker layer (EBL)/emission layer (EML)/optional hole blocker layer (HBL)/electron transport layer (ETL)/optional 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 table 1. The materials required for production of the OLEDs are shown in Table 3. The data of the OLEDs are listed in table 2.

[0148] All materials are applied by thermal vapour 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 co-evaporation. Details given in such a form as IV1:H4:TEG2 (44%: 44%:12%) mean here that the materials IV1 and 42 are each present in the layer in a proportion by volume of 44%, and TEG1 in a proportion by volume of 12%. Analogously, the electron transport layer may also consist of a mixture of two materials.

[0149] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, 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, as is the lifetime. The electroluminescence spectra are determined at a luminance of 1000 cd/m.sup.2, and the CIE 1931 x and y colour coordinates are calculated therefrom. The parameter U1000 in table 2 refers to the voltage which is required fora 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. The parameter U10 in table 2 refers to the voltage which is required for a current density of 10 mA/cm.sup.2. CE10 and EQE10 respectively denote the current efficiency and external quantum efficiency that are attained at 10 mA/m.sup.2.

[0150] The lifetime LT is defined as the time after which the luminance drops from the starting luminance to a certain proportion L1 in the course of operation with constant current density j.sub.0. A figure of L1=80% in table 2 means that the lifetime reported in the LT column corresponds to the time after which the luminance falls to 80% of its starting value.

[0151] Use of Materials of the Invention in the Emission Layer of Phosphorescent OLEDs

[0152] The inventive materials IV1 to IV31 are used in Examples E1 to E28 and B1 to B54 as matrix material in the emission layer of green-phosphorescing OLEDs. With otherwise comparable performance data of the OLEDs, the use of the compounds of the invention achieves distinctly higher lifetimes compared to PA1 (see table 2). E1-E3 can be compared here directly with V1, E4-E7 directly with V2, E8-E12 directly with V3, E13-E17 directly with V4, and E18-E28 directly with V5, and each comparison shows the improvement in lifetime relative to PA1.

TABLE-US-00008 TABLE 1 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex. thickness thickness thickness thickness thickness thickness thickness V1 SpMA1:PD1 SpMA1 SpMA2 PA1:H12:TEG1 ST2 ST2:LiQ LiQ (95%:5%) 215 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 20 nm 30 nm 30 nm E1 PA2:PD1 SpMA1 SpMA2 IV1:H12:TEG1 ST2 PA6:LiQ LiQ (95%:5%) 215 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 20 nm 30 nm 30 nm E2 SpMA1:PD1 SpMA1 SpMA2 IV2:H12:TEG1 ST2 ST2:LiQ LiQ (95%:5%) 215 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 20 nm 30 nm 30 nm E3 SpMA1:PD1 SpMA1 SpMA2 IV3:H12:TEG1 ST2 ST2:LiQ LiQ (95%:5%) 215 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 20 nm 30 nm 30 nm V2 SpMA1:PD1 SpMA1 SpMA2 PA1:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E4 SpMA1:PD1 SpMA1 SpMA2 IV1:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E5 SpMA1:PD1 SpMA1 SpMA2 IV5:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E6 SpMA1:PD1 SpMA1 SpMA2 IV10:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E7 SpMA1:PD1 SpMA1 SpMA2 IV3:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V3 SpMA1:PD1 SpMA1 SpMA2 PA1:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E8 SpMA1:PD1 SpMA1 SpMA2 IV1:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E9 SpMA1:PD1 SpMA1 SpMA2 IV5:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E10 SpMA1:PD1 SpMA1 SpMA2 IV10:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E11 SpMA1:PD1 SpMA1 SpMA2 IV11:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E12 SpMA1:PD1 SpMA1 SpMA2 IV3:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V4 SpMA1:PD1 SpMA1 SpMA2 PA1:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E13 SpMA1:PD1 SpMA1 SpMA2 IV1:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E14 SpMA1:PD1 SpMA1 SpMA2 IV5:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E15 SpMA1:PD1 SpMA1 SpMA2 IV10:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E16 SpMA1:PD1 SpMA1 SpMA2 IV11:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E17 SpMA1:PD1 SpMA1 SpMA2 IV3:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm V5 SpMA1:PD1 SpMA1 SpMA2 PA1:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E18 SpMA1:PD1 SpMA1 SpMA2 IV1:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E19 SpMA1:PD1 SpMA1 SpMA2 IV2:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E20 SpMA1:PD1 SpMA1 SpMA2 IV8:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E21 SpMA1:PD1 SpMA1 SpMA2 IV14:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E22 SpMA1:PD1 SpMA1 SpMA2 IV15:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E23 SpMA1:PD1 SpMA1 SpMA2 IV16:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E24 SpMA1:PD1 SpMA1 SpMA2 IV18:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E25 SpMA1:PD1 SpMA1 SpMA2 IV21:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E26 SpMA1:PD1 SpMA1 SpMA2 IV22:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E27 SpMA1:PD1 SpMA1 SpMA2 IV25:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm E28 SpMA1:PD1 SpMA1 SpMA2 IV26:H26:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B1 SpMA1:PD1 SpMA1 SpMA2 IV1:H4:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B2 SpMA1:PD1 SpMA1 SpMA2 IV1: H19:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B3 SpMA1:PD1 SpMA1 SpMA2 IV5:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B4 SpMA1:PD1 SpMA1 SpMA2 IV7:H17:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B5 SpMA1:PD1 SpMA1 SpMA2 IV7:H1:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B6 SpMA1:PD1 SpMA1 SpMA2 IV8:H5:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B7 SpMA1:PD1 SpMA1 SpMA2 IV9:H23:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B8 SpMA1:PD1 SpMA1 SpMA2 IV10:H2:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B9 SpMA1:PD1 SpMA1 SpMA2 IV10:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B10 SpMA1:PD1 SpMA1 SpMA2 IV12:H5:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B11 SpMA1:PD1 SpMA1 SpMA2 IV13:H4:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B12 SpMA1:PD1 SpMA1 SpMA2 IV13:H26:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B13 SpMA1:PD1 SpMA1 SpMA2 IV9:H11:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:22%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B14 SpMA1:PD1 SpMA1 SpMA2 IV4:H8:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B15 SpMA1:PD1 SpMA1 SpMA2 IV9:H14:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B16 SpMA1:PD1 SpMA1 SpMA2 IV1:H1:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B17 SpMA1:PD1 SpMA1 SpMA2 IV3:H8:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B18 SpMA1:PD1 SpMA1 SpMA2 IV1:H34:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B19 SpMA1:PD1 SpMA1 SpMA2 IV19:H2:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B20 SpMA1:PD1 SpMA1 SpMA2 IV2:H7:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B21 SpMA1:PD1 SpMA1 SpMA2 IV20:H1:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B22 SpMA1:PD1 SpMA1 SpMA2 IV22:H5:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B23 SpMA1:PD1 SpMA1 SpMA2 IV1:H9:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B24 SpMA1:PD1 SpMA1 SpMA2 IV1:H14:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B25 SpMA1:PD1 SpMA1 SpMA2 IV23:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B26 SpMA1:PD1 SpMA1 SpMA2 IV24:H9:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B27 SpMA1:PD1 SpMA1 SpMA2 IV10:H32:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B28 SpMA1:PD1 SpMA1 SpMA2 IV2:H19:TEG1 ST2 ST2:LiQ LiQ (95%:5%) 215 nm 20 nm (44%:44%:12%) 10 nm (50%:50%) 1 nm 20 nm 30 nm 30 nm B29 SpMA1:PD1 SpMA1 SpMA2 IV11:H29:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B30 SpMA1:PD1 SpMA1 SpMA2 IV1:H1:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B31 SpMA1:PD1 SpMA1 SpMA2 IV16:H2:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B32 SpMA1:PD1 SpMA1 SpMA2 IV18:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B33 SpMA1:PD1 SpMA1 SpMA2 IV15:H5:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B34 SpMA1:PD1 SpMA1 SpMA2 IV23:H19:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (23%:70%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B35 SpMA1:PD1 SpMA1 SpMA2 IV22:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (30%:60%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B36 SpMA1:PD1 SpMA1 SpMA2 IV20:H11:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (68%:20%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B37 SpMA1:PD1 SpMA1 SpMA2 IV26:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (22%:70%:8%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B38 SpMA1:PD1 SpMA1 SpMA2 IV14:H5:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (32%:61%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B39 SpMA1:PD1 SpMA1 SpMA2 IV12:H8:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B40 SpMA1:PD1 SpMA1 SpMA2 IV5:H6:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B41 SpMA1:PD1 SpMA1 SpMA2 IV24:H7:TEG3 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B42 SpMA1:PD1 SpMA1 SpMA2 IV27:H2:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B43 SpMA1:PD1 SpMA1 SpMA2 IV27:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B44 SpMA1:PD1 SpMA1 SpMA2 IV27:H5:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B45 SpMA1:PD1 SpMA1 SpMA2 IV28:H1:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:12%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B46 SpMA1:PD1 SpMA1 SpMA2 IV29:H2:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B47 SpMA1:PD1 SpMA1 SpMA2 IV29:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B48 SpMA1:PD1 SpMA1 SpMA2 IV29:H5:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B49 SpMA1:PD1 SpMA1 SpMA2 IV30:H2:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B50 SpMA1:PD1 SpMA1 SpMA2 IV30:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B51 SpMA1:PD1 SpMA1 SpMA2 IV30:H5:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B52 SpMA1:PD1 SpMA1 SpMA2 IV31:H2:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B53 SpMA1:PD1 SpMA1 SpMA2 IV31:H4:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm B54 SpMA1:PD1 SpMA1 SpMA2 IV31:H5:TEG2 ST2 ST2:LiQ LiQ (95%:5%) 200 nm 20 nm (44%:44%:7%)  5 nm (50%:50%) 1 nm 20 nm 40 nm 30 nm

TABLE-US-00009 TABLE 2 Data of the OLEDs U1000 CE1000 EQE1000 CIE x/y at j0 L1 LT Ex. (V) (cd/A) (%) 1000 cd/m2 (mA/cm.sup.2) (%) (h) V1 3.3 68 19 0.32/0.63 20 80 990 E1 3.3 70 19 0.35/0.61 20 80 1170 E2 3.3 73 20 0.35/0.61 20 80 1270 E3 3.4 71 19 0.34/0.62 20 80 1330 U10 CE10 EQE10 CIE x/y at j0 L1 LT Ex. (V) (cd/A) (%) 1000 cd/m2 (mA/cm.sup.2) (%) (h) V2 4.9 64 17 0.34/0.62 40 80 1210 E4 4.7 63 17 0.34/0.62 40 80 1420 E5 4.8 62 17 0.34/0.62 40 80 1350 E6 4.7 62 17 0.34/0.62 40 80 1310 E7 4.8 62 17 0.34/0.62 40 80 1490 V3 5.4 68 18 0.34/0.62 40 80 600 E8 5.3 71 19 0.34/0.62 40 80 710 E9 5.4 70 19 0.34/0.62 40 80 670 E10 5.3 70 19 0.34/0.62 40 80 650 E11 5.4 68 18 0.34/0.62 40 80 630 E12 5.4 70 19 0.34/0.62 40 80 750 V4 4.3 86 22 0.35/0.63 40 80 630 E13 4.4 89 23 0.35/0.63 40 80 810 E14 4.4 89 23 0.35/0.63 40 80 1030 E15 4.5 92 24 0.35/0.63 40 80 790 E16 4.5 87 23 0.35/0.63 40 80 770 E17 4.8 86 22 0.35/0.63 40 80 850 V5 4.6 85 22 0.35/0.63 40 80 550 E18 4.5 88 23 0.35/0.63 40 80 700 E19 4.4 92 24 0.35/0.63 40 80 640 E20 4.8 86 22 0.35/0.63 40 80 720 E21 4.4 87 23 0.35/0.63 40 80 790 E22 4.4 93 24 0.35/0.63 40 80 630 E23 4.5 88 23 0.35/0.63 40 80 730 E24 4.4 87 23 0.35/0.63 40 80 650 E25 4.4 85 22 0.35/0.63 40 80 840 E26 4.1 86 22 0.35/0.63 40 80 785 E27 4.1 84 22 0.35/0.63 40 80 900 E28 4.3 87 23 0.35/0.63 40 80 640 B1 4.3 79 21 0.35/0.63 40 80 1170 B2 4.8 60 16 0.34/0.62 40 80 1010 B3 4.4 77 20 0.35/0.63 40 80 1130 B4 4.6 64 18 0.34/0.62 40 80 1150 B5 4.4 77 20 0.35/0.63 40 80 1010 B6 4.7 63 17 0.34/0.62 40 80 1340 B7 4.3 75 20 0.35/0.63 40 80 1050 B8 4.3 78 21 0.35/0.63 40 80 1080 B9 4.4 77 20 0.35/0.63 40 80 1080 B10 4.5 78 21 0.35/0.63 40 80 1130 B11 4.3 78 21 0.35/0.63 40 80 1020 B12 4.8 58 16 0.34/0.62 40 80 1260 B13 3.9 69 18 0.35/0.63 40 80 910 B14 4.4 64 17 0.34/0.62 40 80 1390 B15 4.3 80 21 0.35/0.63 40 80 1010 B16 4.2 80 21 0.35/0.63 40 80 1150 B17 4.7 63 17 0.34/0.62 40 80 1540 B18 5.2 72 19 0.34/0.62 40 80 750 B19 5.5 71 19 0.34/0.62 40 80 860 B20 4.2 88 23 0.35/0.63 40 80 940 B21 4.6 64 18 0.34/0.62 40 80 1030 B22 4.3 86 22 0.35/0.63 40 80 1010 B23 4.4 90 24 0.35/0.63 40 80 870 B24 4.1 92 24 0.35/0.63 40 80 670 B25 5.3 70 19 0.34/0.62 40 80 870 B26 4.4 77 20 0.35/0.63 40 80 850 B27 5.1 67 18 0.34/0.62 40 80 740 B28 3.4 71 19 0.35/0.61 20 80 1250 B29 5.0 67 18 0.34/0.62 40 80 680 B30 4.3 82 21 0.35/0.63 40 80 990 B31 4.7 66 18 0.34/0.62 40 80 1230 B32 4.7 63 17 0.34/0.62 40 80 1450 B33 4.0 87 22 0.35/0.63 40 80 890 B34 5.0 74 20 0.34/0.62 40 80 610 B35 4.2 85 22 0.35/0.63 40 80 1040 B36 4.2 60 16 0.34/0.62 40 80 1210 B37 4.3 85 22 0.35/0.63 40 80 910 B38 5.4 72 19 0.34/0.62 40 80 890 B39 4.6 77 20 0.35/0.63 40 80 1170 B40 4.4 77 20 0.35/0.63 40 80 1410 B41 4.6 75 20 0.35/0.63 40 80 1080 B42 4.5 67 18 0.34/0.62 40 80 1120 B43 4.6 66 18 0.34/0.62 40 80 1170 B44 4.4 66 18 0.34/0.62 40 80 1090 B45 4.4 68 19 0.34/0.62 40 80 1290 B46 5.4 71 19 0.34/0.62 40 80 860 B47 5.3 71 19 0.34/0.62 40 80 830 B48 5.2 72 19 0.34/0.62 40 80 850 B49 5.5 70 19 0.34/0.62 40 80 890 B50 5.5 72 19 0.34/0.62 40 80 860 B51 5.3 72 19 0.34/0.62 40 80 860 B52 5.5 69 19 0.34/0.62 40 80 830 B53 5.5 71 19 0.34/0.62 40 80 820 B54 5.3 74 20 0.34/0.62 40 80 790

TABLE-US-00010 TABLE 3 Structural formulae of the materials for the OLEDs [00570] PD1 [00571] SpMA1 [00572] SpMA2 [00573] ST2 [00574] LiQ [00575] TEG1 [00576] TEG-2 [00577] TEG3 [00578] H12 [00579] PA1 [00580] H1 [00581] H2 [00582] H4 [00583] H5 [00584] H6 [00585] H7 [00586] H8 [00587] H9 [00588] H11 [00589] H14 [00590] H17 [00591] H19 [00592] H23 [00593] H26 [00594] H29 [00595] H32 [00596] H34 [00597] P3/IV1 [00598] P5/IV2 [00599] P1/IV3 [00600] P7/IV4 [00601] P105/IV5 [00602] P107/IV7 [00603] P102/IV8 [00604] P101/IV9 [00605] P14/IV10 [00606] P13/IV11 [00607] P17/IV12 [00608] P15/IV13 [00609] P18/IV14 [00610] P20/IV15 [00611] P21/IV16 [00612] P22/IV17 [00613] P23/IV18 [00614] P24/IV19 [00615] P26/IV20 [00616] P28/IV21 [00617] P29/IV22 [00618] P30/IV23 [00619] P109/IV24 [00620] P110/IV25 [00621] P100/IV26 [00622] P32/IV27 [00623] P33/IV28 [00624] P2/IV29 [00625] P34/IV30 [00626] P35/IV31