MATERIALS FOR ELECTRONIC DEVICES

Abstract

The present invention relates to compounds according to formula (I), which are suitable for use in electronic devices, preferably organic electroluminescent devices.

Claims

1-18. (canceled)

19. A compound of formula (I): ##STR00129## wherein Y is the same or different in each instance and is CR.sup.1 or N; Z is C if X is present and is Y if X is not present; X is the same or different in each instance and is a bivalent group selected from the group consisting of C(R.sup.1).sub.2 and Si(R.sup.1).sub.2; R.sup.1 is the same or different in each instance and is selected from the group consisting of H, D, F, C(O)R.sup.2, CN, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, P(O)(R.sup.2).sub.2, OR.sup.2, S(O)R.sup.2, S(O).sub.2R.sup.2, straight-chain alkyl, or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups baying 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; wherein two or more radicals R.sup.1 are optionally joined to one another so as to define a ring; wherein the alkyl, alkoxy, alkenyl, and all ynyl groups, and the aromatic and heteroaromatic ring systems are each optionally substituted by one or more radicals R.sup.2; and wherein one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl, and alkenyl groups are optionally replaced by R.sup.2CCR.sup.2, CC, Si(R.sup.2).sub.2, CO, CNR.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; R.sup.2 is the same or different in each instance and is selected from the group consisting of H, D, CN, alkyl groups having 1 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; wherein two or more radicals R.sup.2 are optionally joined to one another so as to define a ring; and wherein the alkyl groups, aromatic ring systems, and heteroaromatic ring systems are each optionally substituted by F CN; a, b, c, and d are the same or different in each instance and are 0 or 1, with the proviso that a+b=1 and c+d=1, wherein when any one of a, b, c, or d is 0, the corresponding X is absent; wherein at least one Y has a group of formula (N) bonded thereto instead of R.sup.1, ##STR00130## wherein the bond identified by an asterisk indicates the bond to Y; Ar.sup.1 is the same or different in each instance and is selected from the group consisting of aromatic ring systems having 6 to 30 aromatic ring atoms and optionally substituted by one or more radicals R.sup.1 and heteroaromatic ring systems which have 5 to 30 aromatic ring atoms and optionally substituted by one or more radicals R.sup.1; E is a single bond or a divalent group selected from the group consisting of arylene groups optionally substituted by one or more radicals R.sup.1, heteroarylene groups optionally substituted by one or more radicals R.sup.1, B(R.sup.1) C(R.sup.1).sub.2, C(R.sup.1)C(R.sup.1), CC, Si(R.sup.1).sub.2; CO, CNR.sup.1, CC(R.sup.1).sub.2, O, S, SO, SO.sub.2, N(R.sup.1), P(R.sup.1), and P(O)R.sup.1, combinations of 2, 3, or 4 identical or different groups among these.

20. The compound of claim 19, wherein the compound of formula, (1) contains exactly one Y wherein a group of formula (N) is bonded thereto instead of R.sup.1.

21. The compound of claim 19, wherein in the group of formula (N), Ar.sup.1 is the same or different in each instance and is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, indenofluorenyl, carbazolyl, dibenzothiophenyl, dibenzofusanyl, benzofuranyl, benzothiophenyl, indolyl, triazinyl, pyrimidinyl, pyridyl, and pyridazinyl, each of which is optionally substituted by one or more radicals R.sup.1.

22. The compound of claim 19, wherein Ar.sup.1 is the same in each instance.

23. The compound of claim 19, wherein E in the group of formula (N) is the same or different in each instance and is selected from the group consisting of a single bond, arylene groups optionally substituted by one or more radicals R.sup.1, heteroarylene groups optionally substituted by one or more radicals R.sup.1, and the following divalent groups; ##STR00131##

24. The compound of claim 19, wherein the group of formula (N) is a group of formulae (N-1) through (N-12): ##STR00132## ##STR00133## ##STR00134## ##STR00135## wherein the groups of formulae (N-1) through (N-12) is optionally substituted with a radical R.sup.1 at any position indicated as unsubstituted.

25. The compound of claim 19, wherein all Y are CR.sup.1.

26. The compound of claim 19, wherein X is C(R.sup.1).sub.2.

27. The compound of claim 19, wherein the radicals R.sup.1 of X are the same or different in each instance and are selected from the group consisting of straight-chain alkyl groups having 1 to 12 carbon atoms, branched or cyclic alkyl groups having 3 to 12 carbon atoms, and aromatic ring systems having 6 to 20 aromatic ring atoms; wherein the alkyl groups and aromatic ring systems are each optionally substituted by one of more radicals R.sup.2.

28. The compound of claim 19, Therein the radicals R.sup.1 in Y are the same or different each instance and are selected from the group consisting of H, D, F, CN, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl 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, wherein the alkyl groups and aromatic and heteroaromatic ring systems are each optionally substituted by one or more radicals R.sup.2.

29. The compound of claim 19, wherein the compound of formula (I) is a compound of formulae (I-1-1) through (I-4-1): ##STR00136##

30. A process for preparing the compound of formula (I) of claim 19, comprising reacting a monobenzoindenofluorene derivative comprising one or more reactive groups with an amine in a transition pleat-catalyzed coupling reaction.

31. An oligomer, polymer, or dendrimer comprising one or more compounds of formula (I) of claim 19, wherein the bond(s) to the polymer, oligomer, or dendrimer are located at any desired position(s) substituted by R.sup.1 or R.sup.2.

32. A formulation comprising at least one compound of formula (I) of claim 19 and at least one solvent.

33. A formulation comprising at, least one oligomer, polymer, or dendrimer of claim 31 and at least one solvent.

34. An electronic device comprising at least one compound of formula (I) of claim 19.

35. An electronic device comprising at least one oligomer, polymer, or dendrimer of claim 31.

36. The electronic device of claim 34, wherein the electronic device is an organic electroluminescent device comprising an anode, a cathode and at least one emitting layer, wherein at least one organic layer of the device, which is optionally an emitting layer, a hole transport layer, or another layer, comprises the at least one compound.

37. The electronic device of claim 35, wherein the electronic device is an organic electroluminescent device comprising an anode, a cathode and at least one emitting layer, wherein at least one organic layer of the device, which is optionally an emitting layer, a hole transport layer, or another layer, comprises the at least one oligomer, polymer, or dendrimer.

38. The electronic device of 36, wherein the at least one organic layer is an emitting layer.

39. The electronic device of 37, wherein the at least one organic layer is an emitting layer.

40. The electronic device of 38, wherein the emitting layer further comprises one or more matrix compounds.

41. The electronic device of 39, wherein the emitting layer further comprises one or more matrix compounds.

Description

[0087] The FIGURES for the proportions in % are understood in the context of the present application to mean % by volume when the compounds are applied from the gas phase, and to mean % by weight when the compounds are applied from solution.

[0088] Detailed hereinafter are generally preferred material classes for use as corresponding functional materials in the organic electroluminescent devices of the invention.

[0089] Suitable phosphorescent emitting compounds are especially compounds which, when suitably excited, emit light, preferably in the visible region, and also contain at least one atom of atomic number greater than 20, preferably greater than 38, and less than 84, more preferably greater than 56 and less than 80. Preference is given to using, as phosphorescent emitting compounds, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium, platinum or copper.

[0090] In the context of the present invention, all luminescent iridium, platinum or copper complexes are considered to be phosphorescent compounds.

[0091] Examples of the above-described phosphorescent emitting compounds can be found in applications WO 2000/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 2005/033244, WO 2005/019373 and US 2005/0258742. In general, all phosphorescent complexes as used for phosphorescent OLEDs according to the prior art and as known to those skilled in the art in the field of organic electroluminescent devices are suitable for use in the devices of the invention. It is also possible for the person skilled in the art, without exercising inventive skill, to use further phosphorescent complexes in combination with the compounds of the invention in OLEDs.

[0092] Preferred fluorescent emitters are, aside from the compounds of the invention, selected from the class of the arylamines. An arylamine in the context of this invention is understood to mean a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 aromatic ring atoms. Preferred examples of these are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines or aromatic chrysenediamines. An aromatic anthraceneamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9 position. An aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10 positions. Aromatic pyreneamines, pyrenediamines, chryseneamines and chrysenediamines are defined analogously, where the diarylamino groups are bonded to the pyrene preferably in the 1 position or 1,6 positions. Further preferred emitters are indenofluoreneamines or -diamines, for example according to WO 2006/108497 or WO 2006/122630, benzoindenofluoreneamines or -diamines, for example according to WO 2008/006449, and dibenzoindenofluoreneamines or -diamines, for example according to WO 2007/140847, and the indenofluorene derivatives having fused aryl groups disclosed in WO 2010/012328. Likewise preferred are the pyrenearylamines disclosed in WO 2012/048780 and WO 2013/185871. Likewise preferred are the benzoindenofluoreneamines disclosed in WO 2014/037077, the benzofluoreneamines disclosed in WO 2014/106522 and the extended indenofluorenes disclosed in WO 2014/111269.

[0093] Preferred matrix materials for use in combination with fluorescent emitting compounds are selected from the classes of the oligoarylenes (e.g. 2,2,7,7-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), especially of the oligoarylenes containing fused aromatic groups, the oligoarylenevinylenes (e.g. DPVBi or spiro-DPVBi according to EP 676461), the polypodal metal complexes (for example according to WO 2004/081017), the hole-conducting compounds (for example according to WO 2004/058911), the electron-conducting compounds, especially ketones, phosphine oxides, sulfoxides, etc. (for example according to WO 2005/084081 and WO 2005/084082), the atropisomers (for example according to WO 2006/048268), the boronic acid derivatives (for example according to WO 2006/117052) or the benzanthracenes (for example according to WO 2008/145239). Particularly preferred matrix materials are selected from the classes of the oligoarylenes comprising naphthalene, anthracene, benzanthracene and/or pyrene or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulfoxides. Very particularly preferred matrix materials are selected from the classes of the oligoarylenes comprising anthracene, benzanthracene, benzophenanthrene and/or pyrene or atropisomers of these compounds. An oligoarylene in the context of this invention shall be understood to mean a compound in which at least three aryl or arylene groups are bonded to one another.

[0094] Particularly preferred matrix materials for use in combination with the compound of the formula (I) in the emitting layer are depicted in the following table:

TABLE-US-00002 [00061] [00062] [00063] [00064] [00065] [00066] [00067] [00068] [00069] [00070] [00071] [00072] [00073] [00074] [00075] [00076] [00077] [00078] [00079] [00080] [00081] [00082] [00083] [00084] [00085] [00086] [00087] [00088] [00089] [00090] [00091] [00092] [00093] [00094] [00095] [00096] [00097] [00098] [00099] [00100] [00101] [00102] [00103] [00104] [00105] [00106] [00107] [00108] [00109] [00110] [00111] [00112] [00113] [00114] [00115] [00116]

[0095] Suitable charge transport materials as usable in the hole injection or hole transport layer or electron blocker layer or in the electron transport layer of the organic electroluminescent device of the invention are, as well as the compounds of the invention, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials as used in these layers according to the prior art.

[0096] Examples of preferred hole transport materials which can be used in a hole transport, hole injection or electron blocker layer in the electroluminescent device of the invention are indenofluoreneamine derivatives (for example according to WO 06/122630 or WO 06/100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (for example according to WO 01/049806), amine derivatives having fused aromatic systems (for example according to U.S. Pat. No. 5,061,569), the amine derivatives disclosed in WO 95/09147, monobenzoindenofluoreneamines (for example according to WO 08/006449), dibenzoindenofluoreneamines (for example according to WO 07/140847), spirobifluoreneamines (for example according to WO 2012/034627 or WO 2013/120577), fluoreneamines (for example according to WO 2014/015937, WO 2014/015938 and WO 2014/015935), spirodibenzopyranamines (for example according to WO 2013/083216) and dihydroacridine derivatives (for example according to WO 2012/150001).

[0097] Preferred cathodes of the organic electroluminescent device are metals having a low work function, metal alloys or multilayer structures composed of various metals, for example alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Additionally suitable are alloys composed of an alkali metal or alkaline earth metal and silver, for example an alloy composed of magnesium and silver. In the case of multilayer structures, in addition to the metals mentioned, it is also possible to use further metals having a relatively high work function, for example Ag or Al, in which case combinations of the metals such as Ca/Ag, Mg/Ag or Ba/Ag, for example, are generally used. It may also be preferable to introduce a thin interlayer of a material having a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of useful materials for this purpose are alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g. LiF, Li.sub.2O, BaF.sub.2, MgO, NaF, CsF, Cs.sub.2CO.sub.3, etc.). It is also possible to use lithium quinolinate (LiQ) for this purpose. The layer thickness of this layer is preferably between 0.5 and 5 nm.

[0098] Preferred anodes are materials having a high work function. Preferably, the anode has a work function of greater than 4.5 eV versus vacuum. Firstly, metals having a high redox potential are suitable for this purpose, for example Ag, Pt or Au. Secondly, metal/metal oxide electrodes (e.g. Al/Ni/NiO.sub.x, Al/PtO.sub.x) may also be preferred. For some applications, at least one of the electrodes has to be transparent or partly transparent in order to enable the irradiation of the organic material (organic solar cell) or the emission of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is further given to conductive doped organic materials, especially conductive doped polymers.

[0099] The device is appropriately (according to the application) structured, contact-connected and finally sealed, since the lifetime of the devices of the invention is shortened in the presence of water and/or air.

[0100] In a preferred embodiment, the organic electroluminescent device of the invention is characterized in that one or more layers are coated by a sublimation process. In this case, the materials are applied by vapor deposition in vacuum sublimation systems at an initial pressure of less than 10.sup.5 mbar, preferably less than 10.sup.6 mbar. In this case, however, it is also possible that the initial pressure is even lower, for example less than 10.sup.7 mbar.

[0101] Preference is likewise given to an organic electroluminescent device, characterized in that one or more layers are coated by the OVPD (organic vapor phase deposition) method or with the aid of a carrier gas sublimation. In this case, the materials are applied at a pressure between 10.sup.5 mbar and 1 bar. A special case of this method is the OVJP (organic vapor jet printing) method, in which the materials are applied directly by a nozzle and thus structured (for example M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0102] Preference is additionally given to an organic electroluminescent device, characterized in that one or more layers are produced from solution, for example by spin-coating, or by any printing method, for example screen printing, flexographic printing, nozzle printing or offset printing, but more preferably LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing. For this purpose, soluble compounds of formula (I) are needed. High solubility can be achieved by suitable substitution of the compounds.

[0103] It is further preferable that an organic electroluminescent device of the invention is produced by applying one or more layers from solution and one or more layers by a sublimation method.

[0104] According to the invention, the electronic devices comprising one or more compounds of the invention can be used in displays, as light sources in lighting applications and as light sources in medical and/or cosmetic applications (e.g. light therapy).

WORKING EXAMPLES

A) Synthesis Examples

A-1) Synthesis of Compound 1

[0105] ##STR00117##

[0106] 5-Bromo-7,13-dihydro-7,7,13,13-tetramethylbenzo[g]indeno[1,2-b]fluorene (400 mg, 0.86 mmol, 95.4%), 5,7-dihydro-7,7-dimethylindeno-[2,1-b]carbazole (292.4 mg, 1.03 mmol, 1.2 equiv.), Pd.sub.2(dba).sub.3 (16.07 mg, 0.017 mmol, 2 mol %) and SPhos (14.12 mg, 0.034 mmol, 4 mol %) are weighed into a vial, provided with protective gas atmosphere and sealed a septum, and 8 mL of toluene are added. Subsequently, at RT, K.sub.3PO.sub.4 (583.3 mg, 2.69 mmol, 3.1 equiv.) is added to the reaction mixture while stirring. The reaction mixture is heated overnight at 105 C. for 8 d in a heating block while stirring. After allowing it to cool to room temperature, distilled H.sub.2O is added to the reaction solution and the aqueous phase is extracted with toluene. The organic phase is dried over MgSO.sub.4 and concentrated, and the crude product is purified by column chromatography (eluent:heptane:DCM vol./vol. 15:1.fwdarw.1:1) on silica gel.

[0107] The product is obtained as a pale yellow solid (78 mg, 14%).

[0108] MS (El) m/z calculated for C.sub.49H.sub.39N: 641.3, found [M]+: 641.4.

[0109] Elemental analysis calculated (%) for C.sub.49H.sub.39N: C, 91.69, H, 6.12, N, 2.18, found: C, 91.62, H, 6.55, N, 2.07.

A-2) Synthesis of Compound 2

[0110] ##STR00118##

[0111] 5-Bromo-7,13-dihydro-7,7,13,13-tetramethylbenzo[g]indeno[1,2-b]fluorene (400 mg, 0.86 mmol, 95.4%), 11-dihydro-5H-dibenz[b,f]azepine (184.7 mg, 0.95 mmol, 1.2 equiv.), Pd(OAc).sub.2 (3.93 mg, 0.017 mmol, 2 mol %) and SPhos (14.12 mg, 0.034 mmol, 4 mol %) are weighed into a vial, provided with protective gas atmosphere and sealed a septum, and 6 mL of toluene are added. Subsequently, n-hexyllithium (2.47 M in hexane) (0.39 mL, 0.96 mmol, 1.1 equiv.) is cautiously added dropwise to the reaction mixture at RT while stirring. The reaction mixture is heated overnight at 85 C. for one day in a heating block while stirring. After allowing it to cool to room temperature, distilled H.sub.2O is added to the reaction solution and the aqueous phase is extracted with toluene. The organic phase is dried over MgSO.sub.4 and concentrated, and the crude product is purified by column chromatography on silica gel (eluent:heptane:toluene vol./vol. 2:1.fwdarw.1:1.fwdarw.DCM).

[0112] The product is obtained as a pale yellow solid (28 mg, 6%).

[0113] MS (El) m/z calculated for C.sub.42H.sub.35N: 553.3, found [M].sup.+: 553.3.

[0114] Elemental analysis calculated (%) for C.sub.42H.sub.35N: C, 91.10, H, 6.37, N, 2.53, found: C, 89.91, H, 7.18, N, 2.25.

A-3) Synthesis of Compound 3

[0115] ##STR00119##

[0116] 5-Bromo-7,13-dihydro-7,7,13,13-tetramethylbenzo[g]indeno[1,2-b]fluorene (400 mg, 0.86 mmol, 95.4%), 5H-dibenzo[b,f]azepine (199.5 mg, 1.03 mmol, 1.2 equiv.), Pd(OAc).sub.2 (3.93 mg, 0.017 mmol, 2 mol %) and SPhos (14.12 mg, 0.034 mmol, 4 mol %) are weighed into a vial, provided with protective gas atmosphere and sealed a septum, and 6 mL of toluene are added. Subsequently, n-hexyllithium (2.47 M in hexane) (0.39 mL, 0.96 mmol, 1.1 equiv.) is cautiously added dropwise to the reaction mixture at RT while stirring. The reaction mixture is heated overnight at 85 C. for one day in a heating block while stirring. After allowing it to cool to room temperature, distilled H.sub.2O is added to the reaction solution and the aqueous phase is extracted with toluene. The organic phase is dried over MgSO.sub.4, filtered (under basic conditions) through AlOx and concentrated. The residue obtained is treated with acetonitrile and 2-propanol, and the precipitated solids are filtered and dried under reduced pressure. 445 mg (93%) of the product are obtained in the form of a shiny yellow solid.

[0117] MS (El) m/z calculated for C.sub.42H.sub.33N: 551.3, found [M].sup.+: 551.4.

[0118] Elemental analysis calculated (%) for C.sub.42H.sub.33N: C, 91.43, H, 6.03, N, 2.54; found: C, 91.13, H, 6.10, N, 2.52.

B) Device Examples

Production of the OLEDs

[0119] OLEDs of the invention and OLEDs according to the prior art are produced by a general method according to WO 04/058911, which is adapted to the circumstances described here (variation in layer thickness, materials).

[0120] In the examples which follow (see tables 1 to 3), the data of various OLEDs are presented. Substrates used are glass substrates coated with structured ITO (indium tin oxide) of thickness 50 nm. The OLEDs basically have the following layer structure: substrate/buffer/hole injection layer 1 (95% HIL1+5% HIL2, 20 nm)/hole transport layer (HTL, thickness stated in table 1)/emission layer (EML, 20 nm)/electron transport layer (50% ETL+50% EIL, 20 nm)/electron injection layer (EIL, 3 nm) and finally a cathode. The cathode is formed by an aluminum layer of thickness 100 nm. The buffer applied by spin-coating is a 20 nm-thick layer of Clevios P VP Al 4083 (sourced from Heraeus Clevios GmbH, Leverkusen). All the rest of the materials are applied by thermal vapor deposition in a vacuum chamber. The structure of the OLEDs is shown in table 1. The materials used are shown in table 3.

[0121] The emission layer (EML) always consists of at least one matrix material (host, H) and an emitting dopant (D) which is added to the matrix material in a particular proportion by volume by co-evaporation. Details given in such a form as H1:D1 (97%:3%) mean here that the material H1 is present in the layer in a proportion by volume of 97% and D1 in a proportion by volume of 3%.

[0122] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra are recorded, and the current efficiency (measured in cd/A) and the external quantum efficiency (EQE, measured in percent) are calculated as a function of luminance, assuming Lambertian emission characteristics, from current-voltage-luminance characteristics (IUL characteristics), and finally the lifetime of the components is determined. The electroluminescence spectra are recorded at a luminance of 1000 cd/m.sup.2, and the CIE 1931 x and y color coordinates are calculated therefrom. The parameter EQE @ 10 mA/cm.sup.2 refers to the external quantum efficiency at an operating current density of 10 mA/cm.sup.2. The lifetime LD95 @ 10 mA/cm.sup.2 is the time that passes before the starting brightness at an operating current density of 10 mA/cm.sup.2 has dropped by 5%. The data obtained for the various OLEDs are collated in table 2.

[0123] Results: Use of the Compounds of the Invention as Dopants in Fluorescent OLEDs

[0124] The compounds of the invention are particularly suitable as blue-fluorescing dopants. The inventive compound D2 is used in the present examples as emitter in the emitting layer of OLEDs, in each case in combination with one of the host materials H1 and H2. As a comparative example, the emitter C-D1 is analyzed, likewise in each case in combination with one of the host materials H1 and H2.

[0125] The inventive OLEDs obtained are identified as 13 and 14 in table 2. They exhibit very good lifetime with deep blue emission. Compared to the emitter material C-D1 known in the prior art (cf. OLEDs C1 and C2 in table 2), both the external quantum efficiency and the lifetime are significantly improved, with deep blue emission.

TABLE-US-00003 TABLE 1 Structure of the OLEDs EML Ex. HTL Thickness/nm C1 20 nm H1 (95%):C-D1 (5%)/20 nm C2 195 nm H2 (95%):C-D1 (5%)/20 nm I3 20 nm H1 (95%):D2 (5%)/20 nm I4 195 nm H2 (95%):D2 (5%)/20 nm

TABLE-US-00004 TABLE 2 Data of the OLEDs EQE @ LD95 @ 10 mA/cm.sup.2 10 mA/cm.sup.2 CIE Ex. % [h] x y C1 6.8 55 0.149 0.123 C2 6.5 50 0.149 0.115 I3 7.5 90 0.150 0.118 I4 7.2 80 0.149 0.121

TABLE-US-00005 TABLE 3 Structures of the materials used [00120] HIL1 [00121] ETL [00122] HIL2 [00123] EIL [00124] HTL [00125] H1 [00126] H2 [00127] C-D1 [00128] D2