MATERIAS FOR ELECTRONIC DEVICES

Abstract

The present invention relates to a compound of the formula (I), (II) or (III), to the use of the compound in an electronic device, and to an electronic device comprising a compound of the formula (I), (II) or (III). The present invention furthermore relates to a process for the preparation of a compound of the formula (I), (II) or (III) and to a formulation comprising one or more compounds of the formula (I), (II) or (III).

Claims

1-17. (canceled)

18. A compound of the formula (I) ##STR00551## wherein A is C(R.sup.1).sub.2 or ##STR00552## where the dashed lines represent the bonds emanating from the group A; Z is, identically or differently on each occurrence, CR.sup.1, N, or, if a group is bonded in the relevant position, C; Ar.sup.1, Ar.sup.3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R.sup.1; Ar.sup.2 is, identically or differently on each occurrence, an arylene group having 6 to 30 aromatic ring atoms or a heteroarylene group having 5 to 14 aromatic ring atoms, optionally substituted by one or more radicals R.sup.1; Ar.sup.4 is, identically or differently on each occurrence, an aryl group having 6 to 30 aromatic ring atoms or a heteroaryl group having 5 to 14 aromatic ring atoms, optionally substituted by one or more radicals R.sup.1, with the proviso that radicals R.sup.1 on groups Ar.sup.4 do not define a ring system; R.sup.1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms, a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein the above-mentioned groups are optionally substituted by one or more radicals R.sup.2, and wherein one or more CH.sub.2 groups in the above-mentioned groups are optionally replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, C═O, C═S, C═NR.sup.2, —C(═O)O—, —C(═O)NR.sup.2—, NR.sup.2, P(═O)(R.sup.2), —O—, —S—, SO, or SO.sub.2, and wherein one or more H atoms in the above-mentioned groups are optionally replaced by D, F, Cl, Br, I, CN, NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R.sup.2, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R.sup.2, wherein two or more radicals R.sup.1 optionally define a ring system; R.sup.2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein the above-mentioned groups are optionally substituted by one or more radicals R.sup.3, and wherein one or more CH.sub.2 groups in the above-mentioned groups are optionally replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, —C(═O)O—, —C(═O)NR.sup.3—, NR.sup.3, P(═O)(R.sup.3), —O—, —S—, SO, or SO.sub.2, and wherein one or more H atoms in the above-mentioned groups are optionally replaced by D, F, Cl, Br, I, CN, or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R.sup.3, or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R.sup.3, wherein two or more radicals R.sup.2 optionally define a ring system; R.sup.3 is, identically or differently on each occurrence, H, D, F, or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by D or F; m is 0, 1, 2, or 3, wherein when m=0, the group is not present; n is 0, 1, 2, or 3, wherein when n=0, the group is not present; wherein the group Ar.sup.1 or the nitrogen atom is bonded to the fluorene ring system in the 1-position, in the 3-position, or in the 4-position; and with the proviso that the compound does not contain a heteroaryl group which contains more than 14 aromatic ring atoms.

19. The compound of claim 18, wherein the group Ar.sup.1 or, in the case where m=0, the group N(Ar.sup.3), is bonded to the fluorenyl ring system in the 3-position.

20. The compound of claim 18, wherein A is C(R.sup.1).sub.2.

21. The compound of claim 18, wherein Ar.sup.1 represents an aromatic ring system having 6 to 12 aromatic ring atoms, optionally substituted by one or more radicals R.sup.1.

22. The compound of claim 18, wherein Ar.sup.2 represents a phenylene group, optionally substituted by one or more radicals R.sup.1.

23. The compound of claim 18, wherein m is zero.

24. The compound of claim 18, wherein Z is CR.sup.1 if no group is bonded in the relevant position and wherein Z is C if a group is bonded in the relevant position.

25. The compound of claim 18, wherein n is 1 or 2.

26. The compound of claim 18, with the proviso that no condensed aryl group having more than 14 aromatic ring atoms is present in the compound.

27. The compound of claim 18, wherein the compound cannot be represented by a mirror-symmetrical structural formula.

28. The compound of claim 18, wherein Ar.sup.4 is phenyl, which may be substituted by one or more radicals R.sup.1, where radicals R.sup.1 on groups Ar.sup.4 cannot form rings.

29. The compound of claim 18, wherein Ar.sup.3 is an aromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R.sup.1.

30. The compound of claim 18, wherein R.sup.1 is on each occurrence, identically or differently, selected from H, D, F, CN, Si(R.sup.2).sub.3, N(R.sup.2).sub.2 or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, 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 may be replaced by —C≡C—, —R.sup.2C═CR.sup.2—, Si(R.sup.2).sub.2, C═O, C═NR.sup.2, —NR.sup.2—, —O—, —S—, —C(═O)O— or —C(═O)NR.sup.2—, or 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.2.

31. The compound of claim 18, wherein R.sup.2 is on each occurrence, identically or differently, selected from H, D, F, CN, Si(R.sup.3).sub.3, N(R.sup.3).sub.2 or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.3 and where one or more CH.sub.2 groups in the above-mentioned groups may be replaced by —C≡C—, —R.sup.3C═CR.sup.3—, Si(R.sup.3).sub.2, C═O, C═NR.sup.3, —NR.sup.3—, —O—, —S—, —C(═O)O— or —C(═O)NR.sup.3—, or 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.3.

32. A process for the preparation of the compound of claim 18, wherein a fluorenyl or spirobifluorenyl derivative is reacted with an arylamino compound in a first coupling reaction, and the resultant product is reacted with a triarylamino or carbazole compound in a second coupling reaction.

33. An oligomer, polymer, or dendrimer, containing one or more compounds of claim 18, wherein the bonds to the oligomer, polymer, or dendrimer, are optionally localised at any desired positions in formula (I) that are substituted by R.sup.1.

34. A formulation comprising at least one compound of claim 18 and at least one solvent.

35. A formulation comprising at least one polymer, oligomer, or dendrimer of claim 33 and at least one solvent.

36. An electronic device comprising at least one compound of claim 18.

37. An electronic device comprising at least one polymer, oligomer, or dendrimer, of claim 30.

38. The electronic device of claim 36, wherein said electronic device is selected from the group consisting of organic integrated circuit, organic field-effect transistor, organic thin-film transistor, organic light-emitting transistor, organic solar cell, organic optical detector, organic photoreceptor, organic field-quench device, light-emitting electrochemical cell, organic laser diode, and organic electroluminescent device.

39. The electronic device of claim 37, wherein said electronic device is selected from the group consisting of organic integrated circuit, organic field-effect transistor, organic thin-film transistor, organic light-emitting transistor, organic solar cell, organic optical detector, organic photoreceptor, organic field-quench device, light-emitting electrochemical cell, organic laser diode, and organic electroluminescent device.

40. The electronic device of claim 36, wherein the electronic device is an organic electroluminescent device, and wherein the compound is employed in one or more of the following functions: as hole-transport material in a hole-transport or hole-injection layer, as matrix material in an emitting layer, as electron-blocking material, as exciton-blocking material, as material for an interlayer.

41. The electronic device of claim 37, wherein the electronic device is an organic electroluminescent device, and wherein the polymer, oligomer, or dendrimer, is employed in one or more of the following functions: as hole-transport material in a hole-transport or hole-injection layer, as matrix material in an emitting layer, as electron-blocking material, as exciton-blocking material, as material for an interlayer.

Description

WORKING EXAMPLES

Syntheses of Compounds 1 to 13 According to the Invention:

[0132] The following syntheses are carried out, unless indicated otherwise, under a protective-gas atmosphere. The starting materials can be purchased from ALDRICH or ABCR (palladium(II)acetate, tri-o-tolylphosphine, inorganics, solvents). The synthesis of 3-bromofluorenone (Tetrahedron, 51, 7, 2039-54; 1995) and 3-bromofluorene can be carried out in accordance with the literature (Tetrahedron Letters, 51, 37, 4894-4897; 2010), as can the synthesis of bisbiphenyl-4-yl-(4′-bromobiphenyl-4-yl)amine (JP 2010-111605).

Precursor A: 3-Bromo-9H-fluorene

[0133] ##STR00422##

[0134] 49 ml (1000 mmol) of hydrazine hydrate and then 3 g of freshly prepared Raney nickel are added to a vigorously stirred, refluxing suspension of 64 g (250 mmol) of 3-bromofluorene in a mixture of 1000 ml of toluene and 2000 ml of ethanol. After 2 h under reflux, the mixture is allowed to cool, the solvent is removed in vacuo, the residue is taken up in 1000 ml of warm chloroform, the solution is filtered through silica gel, the clear solution is evaporated to 100 ml, and 300 ml of ethanol are added. After the mixture has been left to stand for 12 h, the colourless crystals are filtered off with suction and subsequently recrystallised twice from chloroform/35 ethanol. Yield: 60 g (240 mmol), 98% of theory; purity: 97% according to .sup.1H-NMR.

Precursor B: 3-Bromo-9,9-dimethyl-9H-fluorene

[0135] ##STR00423##

[0136] 37 g (152 mmol) of 3-bromo-9H-fluorene are dissolved in 600 ml of dried DMSO in a flask which has been dried by heating. 43.9 g (457 mmol) of NaO.sup.tBu are added at room temperature. The suspension, which is now blue, is brought to an internal temperature of 80° C. At this temperature, 64.8 g (457 mmol) of iodomethane are added dropwise to the solution, which is now violet, at such a rate that the internal temperature does not exceed 90° C. (duration: about 30 min). The batch is kept at an internal temperature of 80-90° C. for a further 30 min, then poured into 1500 ml of ice-water and stirred for about 20 min. The precipitated solid is filtered off with suction and washed successively with about 200 ml of H.sub.2O and methanol. Yield: 39 g (144 mmol), 96% of theory; purity: 95% according to .sup.1H-NMR.

Precursor C: 3-Bromo-9,9′-spirobifluorene

[0137] ##STR00424##

[0138] The Grignard reagent prepared from 9.9 g (400 mmol) of magnesium turnings and 93.2 g (68 ml, 400 mmol) of 2-bromobiphenyl in 500 ml of dry diethyl ether is added dropwise over the course of 2 h to a boiling solution of 103 g (400 mmol) of 3-bromo-9-fluorenone in 100 ml of dry diethyl ether. When the addition is complete, the mixture is heated at the boil for a further 3 hours. After cooling overnight, the deposited precipitate is filtered off with suction and washed with cold ether. The residue is hydrolysed in a solution of 15 g of ammonium chloride in 250 ml of ice-water. After 1 h, the alcohol formed is filtered off with suction, washed with water and sucked dry.

[0139] For the ring-closure reaction, the dried fluorenol is boiled for 6 hours in 100 ml of glacial acetic acid, after addition of 3 drops of conc. HCl. The mixture is allowed to crystallise overnight, the product formed is filtered off with suction and washed with glacial acetic acid and water. Yield: 141 g (356 mmol), 95% of theory; purity: 96% according to .sup.1H-NMR.

Precursor D: Synthesis of 9,9-dimethyl-9,9′-spirobifluorene-3-boronic acid

[0140] ##STR00425##

[0141] 70 g (259 mmol) of 3-bromo-9,9-dimethyl-9H-fluorene are dissolved in 1500 ml of dry THF, 135 ml (337 mmol) of a 2.5 M solution of n-butyllithium in cyclohexane are added dropwise at −70° C., and, after 1 h, 37 ml of trimethyl borate (336 mmol) are added dropwise. The mixture is allowed to come to room temperature over the course of 1 h, and the solvent is removed. The residue, which is uniform according to .sup.1H-NMR, is employed in the subsequent reaction without further purification. The yield is 55 g (230 mmol), corresponding to 90% of theory.

[0142] Precursors E and F are obtained analogously:

TABLE-US-00003 Starting Ex. material 1 Product Yield E [00426] [00427] 88% F [00428] [00429] 69%

Precursor G: 3-(4-Bromophenyl)-9,9-dimethyl-9H-fluorene

[0143] ##STR00430##

[0144] 45 g (190 mmol) of 9,9-dimethyl-9,9′-spirobifluorene-3-boronic acid, 53 g (190 mmol) of iodobromobenzene and 13 g (123 mmol) of sodium carbonate are suspended in 180 ml of toluene, 180 ml of dioxane and 60 ml of water. 3.0 mg (2.6 mmol) of Pd(PPh.sub.3).sub.4 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum. The purity is 99.9%. The yield is 51 g (147 mmol), corresponding to 78% of theory.

[0145] Precursors H and I are obtained analogously:

TABLE-US-00004 Starting Ex. material 1 Product Yield H [00431] [00432] 81% I [00433] [00434] 66%

Precursor J: Synthesis of (9,9-dimethyl-9H-fluoren-3-yl)phenylamine

[0146] ##STR00435##

[0147] 50 g (183 mmol) of 3-bromo-9,9-dimethyl-9H-fluorene, 20 ml (220 mmol) of aniline, 1.5 g (2.7 mmol) of DPPF, 0.5 g of palladium(11) acetate and 45 g (486 mmol) of sodium tert-butoxide are heated at the boil for 18 h in 1.51 of toluene under a protective atmosphere. The mixture is subsequently partitioned between toluene and water, the organic phase is washed three times with water and dried over Na.sub.2SO.sub.4 and evaporated in a rotary evaporator. The residue remaining is recrystallised from heptane/ethyl acetate.

[0148] The yield is 31.2 g (110 mmol, 52%). Yield: 46 g (165 mmol), 78% of theory; purity: 97% according to .sup.1H-NMR.

[0149] Compounds K to X are obtained analogously:

TABLE-US-00005 Starting Starting material Ex. material 1 2 Product Yield K [00436] [00437] [00438] 81% L [00439] [00440] [00441] 85% M [00442] [00443] [00444] 73% N [00445] [00446] [00447] 75% O [00448] [00449] [00450] 70% P [00451] [00452] [00453] 71% Q [00454] [00455] [00456] 86% R [00457] [00458] [00459] 89% S [00460] [00461] [00462] 72% T [00463] [00464] [00465] 75% U [00466] [00467] [00468] 79% V [00469] [00470] [00471] 72% W [00472] [00473] [00474] 70% X [00475] [00476] [00477] 65%

Example Compound 1

[0150] ##STR00478##

[0151] A degassed solution of 48 g (87 mmol) of bisbiphenyl-4-yl-(4′-bromobiphenyl-4-yl)amine and 23 g (80 mmol) of (9,9-dimethyl-9H-fluoren-3-yl)phenylamine in 1000 ml of dioxane is saturated with N.sub.2 for 1 h. Then firstly 0.9 ml (4.3 mmol) of P(tBu).sub.3, then 0.48 g (2.1 mmol) of palladium(II) acetate are added to the solution. 12.6 g (131 mmol) of NaOtBu in the solid state is subsequently added. The reaction mixture is heated under reflux for 18 h. After cooling to room temperature, 1000 ml of water are carefully added. The organic phase is washed with 4×50 ml of water, dried over MgSO.sub.4, and the solvent is removed in vacuo. The pure product is obtained by recrystallisation and final sublimation. Yield: 46 g (61 mmol), 71% of theory, purity according to HPLC 99.9%.

[0152] Compounds 2 to 18 are obtained analogously:

TABLE-US-00006 Starting Starting Ex. material 1 material 2 Product Yield 2 [00479] [00480] [00481] 83% 3 [00482] [00483] [00484] 80% 4 [00485] [00486] [00487] 84% 5 [00488] [00489] [00490] 80% 6 [00491] [00492] [00493] 77% 7 [00494] [00495] [00496] 72% 8 [00497] [00498] [00499] 65% 9 [00500] [00501] [00502] 84% 10 [00503] [00504] [00505] 78% 11 [00506] [00507] [00508] 69% 12 [00509] [00510] [00511] 63% 13 [00512] [00513] [00514] 73% 14 [00515] [00516] [00517] 76% 15 [00518] [00519] [00520] 77% 16 [00521] [00522] [00523] 79% 17 [00524] [00525] [00526] 73% 18 [00527] [00528] [00529] 76%

Device Examples: Production of OLEDs

[0153] OLEDs according to the invention and OLEDs in accordance with the prior art are produced by a general process in accordance with WO 2004/058911, which is adapted to the circumstances described here (layer-thickness variation, materials).

[0154] The data for various OLEDs are presented in Examples E1 to E16 below (see Tables 3 and 5 with device data and Tables 2 and 4 with the corresponding information on the device structures). Glass plates 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 basically have the following layer structure: substrate/optional hole-injection layer (HIL)/hole-transport layer (HTL)/optional interlayer (IL)/electron-blocking layer (EBL)/emission layer (EML)/optional hole-blocking layer (HBL)/electron-transport layer (ETL)/optional electron-injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer with a thickness of 100 nm. The precise structure of the OLEDs is shown in Tables 2 and 4. The materials required for the production of the OLEDs are shown in Table 1.

[0155] 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 (emitter), which is admixed with the matrix material or matrix materials in a certain proportion by volume by co-evaporation. An expression such as H1:SEB1 (95%:5%) here means that material H1 is present in the layer in a proportion by volume of 95% and SEB1 is present in the layer in a proportion of 5%. The electron-transport layer may analogously also consist of a mixture of two materials.

[0156] The OLEDs are characterised by standard methods. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in lm/W) and the external quantum efficiency (EQE, measured in percent) as a function of the luminous density, calculated from current/voltage/luminous density characteristic lines (IUL characteristic lines) assuming Lambert emission characteristics, and the lifetime are determined. The electroluminescence spectra are determined at a luminous density of 1000 cd/m.sup.2, and the CIE 1931 x and y colour coordinates are calculated therefrom. The term U @ 1000 cd/m.sup.2 in Table 3 and 5 denotes the voltage required for a luminous density of 1000 cd/m.sup.2. Finally, EQE @ 1000 cd/m.sup.2 denotes the external quantum efficiency at an operating luminous density of 1000 cd/m.sup.2. LT80 @ 6000 cd/m2 is the lifetime until the OLED at a luminance of 6000 cd/m.sup.2 has dropped to 80% of the initial intensity, i.e. to 4800 cd/m.sup.2. The device data for the various OLEDs are summarised in Table 3 and 5, while Tables 2 and 4 show the corresponding device structures.

Use of Compounds According to the Invention as Electron-Blocking Materials/Hole-Transport Materials in Fluorescent and Phosphorescent OLEDs

[0157] Compounds according to the invention are particularly suitable as hole-transport material (HTM), as matrix material or as electron-blocking material (EBM) in OLEDs. They are suitable for use as individual materials in a layer, but also for use in a mixture with one or more further components in the hole-transport layer (HTL), electron-blocking layer (EBL) or emitting layer (EML).

[0158] Compared with devices comprising NPB as EBM (V1 and V5), the devices comprising compounds according to the invention (E1 to E16) exhibit both higher efficiencies and also improved lifetimes.

[0159] Compared with the material in accordance with the prior art HTMV1 (V2), in which the carbazole group and the fluorene group are connected directly to one another via an amino group, the compounds according to the invention exhibit similar or better efficiencies and significantly better lifetimes. Thus, the lifetime of the reference device V2 is virtually 10 times longer compared with E1 and E2 (blue-fluorescent devices), and the lifetime is also virtually doubled in the green-phosphorescent device (V6 compared with E9 and E10).

[0160] The advantage of a 3-fluorene substitution compared with a 2-fluorene substitution is readily evident in the comparison between HTMV2 and HTM6. Better efficiencies and better lifetimes are evident in the blue-fluorescent devices (V3 and E6) and in particular in the green-phosphorescent devices (V7 and E14). The same is also readily evident in the comparison of HTMV3 (V8) against HTM7 (E15) and HTM8 (E16). Here too, a significantly improved efficiency and lifetime is evident, in particular in the case of green-phosphorescent devices.

[0161] The devices discussed above were merely emphasised by way of example. Similar effects can also be observed in the case of the other devices which are not discussed explicitly, as can be seen from the tables with the device data. In general, the devices denoted by V1 to V8 are comparative examples comprising compounds in accordance with the prior art. The devices denoted by E1 to E16 comprise compounds in accordance with the present invention and are thus examples according to the invention.

TABLE-US-00007 TABLE 1 Structures of the materials used [00530] HIL1 [00531] HIL2 [00532] NPB [00533] ETM1 [00534] Alq3 [00535] H1 [00536] SEB1 [00537] LiQ [00538] H2 [00539] Irpy [00540] HTMV1 [00541] HTMV2 [00542] HTMV3 [00543] HTM1 (compound 3) [00544] HTM2 (compound 4) [00545] HTM3 (compound 7) [00546] HTM4 (compound 9) [00547] HTM5 (compound 10) [00548] HTM6 (compound 5) [00549] HTM7 (compound 16) [00550] HTM8 (compound 18)

TABLE-US-00008 TABLE 2 Structure of the OLEDs IL HTL IL HTL2 EBL EML ETL Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Ex. nm nm nm nm nm nm nm V1 HIL1 HIL2 HIL1 NPB H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm V2 HIL1 HIL2 HIL1 HTMV1 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm V3 HIL1 HIL2 HIL1 HTMV2 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm V4 HIL1 HIL2 HIL1 HTMV3 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm E1 HIL1 HIL2 HIL1 HTM1 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm E2 HIL1 HIL2 HIL1 HTM2 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm E3 HIL1 HIL2 HIL1 HTM3 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm E4 HIL1 HIL2 HIL1 NPB HTM4 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 130 nm 5 nm 10 nm 20 nm 20 nm 30 nm E5 HIL1 HIL2 HIL1 NPB HTM5 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 130 nm 5 nm 10 nm 20 nm 20 nm 30 nm E6 HIL1 HIL2 HIL1 HTM6 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm E7 HIL1 HIL2 HIL1 HTM7 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm E8 HIL1 HIL2 HIL1 HTM8 H1(95%):SEB1(5%) ETM1(50%):LiQ(50%) 5 nm 140 nm 5 nm 20 nm 20 nm 30 nm

TABLE-US-00009 TABLE 3 Data for the OLEDs U @ EQE @ LT80 @ 1000 cd/m2 1000 cd/m2 6000 cd/m.sup.2 CIE Ex. V % [h] x y V1 4.7 4.8 70 0.14 0.17 V2 4.4 6.5 10 0.14 0.16 V3 4.6 5.9 60 0.14 0.16 V4 4.5 6.7 90 0.14 0.16 E1 4.5 6.8 105 0.14 0.16 E2 4.4 6.9 110 0.14 0.16 E3 4.5 6.8 105 0.14 0.15 E4 4.6 7.0 120 0.14 0.16 E5 4.6 6.9 110 0.14 0.16 E6 4.5 6.6 80 0.14 0.16 E7 4.5 6.8 100 0.14 0.16 E8 4.5 6.9 95 0.14 0.16

TABLE-US-00010 TABLE 4 Structure of the OLEDs HTL IL HTL2 EBL EML ETL Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Thickness/ Ex. nm nm nm nm nm nm V5  HIL2 HIL1 NPB H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm V6  HIL2 HIL1 HTMV1 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm V7  HIL2 HIL1 HTMV2 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm V8  HIL2 HIL1 HTMV3 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm E9  HIL2 HIL1 HTM1 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm E10 HIL2 HIL1 HTM2 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm E11 HIL2 HIL1 HTM3 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm E12 HIL2 HIL1 NPB HTM4 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 10 nm 80 nm 30 nm 40 nm E13 HIL2 HIL1 NPB HTM5 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 10 nm 80 nm 30 nm 40 nm E14 HIL2 HIL1 HTM6 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm E15 HIL2 HIL1 HTM7 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm E16 HIL2 HIL1 HTM8 H2(88%):Irpy(12%) ETM1(50%):LiQ(50%) 70 nm 5 nm 90 nm 30 nm 40 nm

TABLE-US-00011 TABLE 5 Data for the OLEDs U @ Efficiency @ LT80 @ 1000 cd/m2 1000 cd/m2 8000 cd/m.sup.2 CIE Ex. V % [h] x y V5 3.6 14.4 85 0.32 0.63 V6 3.4 16.8 70 0.33 0.64 V7 3.4 15.6 120 0.33 0.64 V8 3.5 16.7 135 0.33 0.63 E9 3.3 17.6 155 0.34 0.62 E10 3.3 17.8 160 0.33 0.63 E11 3.4 17.0 145 0.33 0.64 E12 3.5 17.5 155 0.34 0.63 E13 3.5 17.8 160 0.34 0.63 E14 3.4 16.4 145 0.33 0.63 E15 3.5 17.6 155 0.33 0.64 E16 3.4 17.8 150 0.33 0.63