ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The invention relates to an organic molecule for optoelectronic devices. According to the invention, the organic molecule has a structure of formula I: Formula I wherein T and V is independently from another selected from the group consisting of R.sup.1 and R.sup.2; R.sup.1 is at each occurrence comprising or consisting of a structure of formula II: Formula II which is bonded via the position marked by the dotted line; and Ar.sup.1 is C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.6.

##STR00001##

Claims

1. An organic molecule, comprising a structure of represented by Formula I: ##STR00094## wherein in Formula I, T and V are each independently selected from the group consisting of R.sup.1 and R.sup.2; R.sup.1 is at each occurrence independently comprising a structure of represented by Formula II: ##STR00095## which is bonded to the core of Formula I via a position marked by the dotted line; Ar.sup.1 is at each occurrence independently a C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.2 is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF.sub.3, CN, F, Si(C.sub.1-C.sub.5-alkyl).sub.3, Si(Ph).sub.3; C.sub.1-C.sub.5-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-aryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C.sub.1-C.sub.5-alkyl, Ph, CN, CF.sub.3 or F; C.sub.3-C.sub.17-heteroaryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C.sub.1-C.sub.5-alkyl, Ph, CN, CF.sub.3 or F; N(C.sub.6-C.sub.18-aryl).sub.2; N(C.sub.3-C.sub.17-heteroaryl).sub.2; and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); R.sup.6 is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF.sub.3, CN, F, Si(C.sub.1-C.sub.5-alkyl).sub.3, Si(Ph).sub.3; C.sub.1-C.sub.5-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; N(C.sub.6-C.sub.18-aryl).sub.2; N(C.sub.3-C.sub.17-heteroaryl).sub.2; and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); and wherein one from among T and V is R.sup.1 and an other one from among T and V is R.sup.2.

2. The organic molecule according to claim 1, wherein Ar.sup.1 is selected from the group consisting of: Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of D, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, SiMe.sub.3, Si.sup.iPr.sub.3, NPh.sub.2, carbazolyl and Ph, naphthyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of D, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, SiMe.sub.3, Si.sup.iPr.sub.3, NPh.sub.2, carbazolyl and Ph, and anthracenyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of D, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, SiMe.sub.3, Si.sup.iPr.sub.3, NPh.sub.2, carbazolyl and Ph.

3. The organic molecule according to claim 1, wherein Ar.sup.1 is at each occurrence independently selected from the group consisting of Formulae IIa to IIp: ##STR00096## ##STR00097## which is bonded to the boron atom B of Formula II via a position marked by “”.

4. The organic molecule according to claim 1, wherein R.sup.1 is selected from the group consisting of Formulae IIa-2 to IIp-2: ##STR00098## ##STR00099## ##STR00100## ##STR00101##

5. The organic molecule according to claim 1, wherein R.sup.2 is at each occurrence independently from one another selected from the group consisting of; OPh, SPh, CF.sub.3, CN, F, Si(C.sub.1-C.sub.5-alkyl).sub.3, Si(Ph).sub.3; C.sub.1-C.sub.5-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-aryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C.sub.1-C.sub.5-alkyl, Ph, CN, CF.sub.3 or F; C.sub.3-C.sub.17-heteroaryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C.sub.1-C.sub.5-alkyl, Ph, CN, CF.sub.3 or F; N(C.sub.6-C.sub.18-aryl).sub.2; N(C.sub.3-C.sub.17-heteroaryl).sub.2; and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl).

6. The organic molecule according to claim 1, wherein R.sup.2 is selected from the group consisting of: Me, .sup.iPr, .sup.tBu, SiMe.sub.3, SiPh.sub.3, and Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, and Ph.

7. The organic molecule according to claim 1, wherein R.sup.2 is selected from the group consisting of: .sup.iPr, and Ph, which is optionally substituted with one or more Ph substituents.

8. The organic molecule according to claim 1, comprising a structure represented by Formula IIIa: ##STR00102##
Formula IIa.

9. The organic molecule according to claim 1, comprising a structure represented by Formula IIIb: ##STR00103##
Formula IIIb.

10. An optoelectronic device comprising the organic molecule according to claim 1 as a luminescent emitter.

11. The optoelectronic device according to claim 10, wherein the optoelectronic device is comprises at least one selected from the group consisting of: organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED-sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

12. A composition, comprising: (a) the organic molecule according to claim 1 in the form of an emitter and/or a host, (b) an emitter and/or a host material, which differs from the organic molecule, and (c) optionally, a dye and/or a solvent.

13. An optoelectronic device, comprising the organic molecule according to claim 1, wherein the device comprises at least one selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED-sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

14. The optoelectronic device according to claim 13, comprising: a substrate, an anode, and a cathode, wherein the anode or the cathode is disposed on the substrate, and a light-emitting layer between the anode and the cathode, and comprising the organic molecule.

15. (canceled)

16. A method for producing an optoelectronic device, the method comprising depositing the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.

17. An optoelectronic device, comprising the composition according to claim 12, wherein the device comprises at least one selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED-sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

18. The optoelectronic device according to claim 13, comprising: a substrate, an anode, and a cathode, wherein the anode or the cathode is disposed on the substrate, and a light-emitting layer between the anode and the cathode, and comprising the composition.

19. A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 12 a vacuum evaporation method or from a solution.

Description

EXAMPLES

General Synthesis Scheme 1

[0320] General synthesis scheme I provides a synthesis scheme for organic molecules according to the invention wherein T=R.sup.2 and V=R.sup.1:

General Procedure for Synthesis AAV1:

[0321] ##STR00027##

[0322] I0 (1.00 equivalents), I0-1 (2.20 equivalents), tetrakis(triphenylphosphine)palladium(0) Pd(PPh.sub.3).sub.4(0.04 equivalents; CAS: 14221−01-3), and potassium carbonate (K.sub.2CO.sub.3; 4.00 equivalents) were stirred under nitrogen atmosphere in dioxane:water (4:1 volume ratio) at 110° C. overnight. After cooling down to room temperature (RT), the reaction mixture was extracted between DCM and brine and the phases were separated. The combined organic layers were dried over MgSO.sub.4 and then the solvent was removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography and AAV1 (I1) was obtained as a solid. Instead of a boronic acid ester, a corresponding boronic acid may be used.

General Procedure for Synthesis AAV2:

[0323] ##STR00028##

[0324] I1 (1.00 equivalents) and liquid bromine (4.0 equivalents; CAS 7726-95-6) were stirred under nitrogen atmosphere in anhydrous dimethylformamide (DMF) at room temperature overnight. The reaction mixture was poured into water. The precipitates were filtered off, washed with water and ethanol. The crude product obtained was purified by recrystallization or column chromatography and AAV2 (12) was obtained as a solid.

General Procedure for Synthesis AAV3:

[0325] ##STR00029##

[0326] wherein X was a halogen selected from the group consisting of F, Cl, Br, and I. In certain embodiments, X was F.

[0327] I2 (1.00 equivalents) was dissolved in THF or tertbutylbenzene under nitrogen atmosphere, n-butyllithium or tert-butyllithium (4.0 equivalents), and 12-1 (3.0 equivalents) were added in sequence and the reaction mixture was stirred at room temperature overnight. The reaction mixture was extracted between DCM and brine and the phases were separated. The combined organic layers were dried over MgSO.sub.4 and then the solvent was removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography to obtain P1.

General Procedure for Synthesis AAV2a:

[0328] ##STR00030##

[0329] I1a (1.00 equivalents) and liquid bromine (2.2 equivalents; CAS 7726-95-6) were stirred under nitrogen atmosphere in chloroform at room temperature overnight. The reaction mixture was extracted between dichloromethane and saturated sodium thiosulfate solution and the phases were separated. The combined organic layers were dried over MgSO.sub.4 and then the solvent was removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography and I2a was obtained as a solid.

General Procedure for Synthesis AAV3a:

[0330] ##STR00031##

[0331] wherein in certain embodiments, R.sub.2 was an C.sub.6-C.sub.18-aryl, wherein optionally one or more hydrogen atoms were independently from each other substituted by C.sub.1-C.sub.5-alkyl, Ph, CN, CF.sub.3 or F;

[0332] I2a (1.00 equivalents) was dissolved in toluene under nitrogen atmosphere, tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3; 0.04 equivalents), I2a-1 (5.0 equivalents), X-Phos (CAS: 564483-18-7; 0.16 equivalents) and potassium phosphate tribasic (CAS: 7778-53-2; 4.00 equivalents) were added in sequence and the reaction mixture was stirred at 110° C. overnight. The reaction mixture was extracted between DCM and brine and the phases were separated. The combined organic layers were dried over MgSO.sub.4 and then the solvent was removed under reduced pressure. The crude product obtained was purified by recrystallization or column chromatography to obtain P1.

General Synthesis Scheme II

[0333] General synthesis scheme II provides a synthesis scheme for the organic molecules of the invention, wherein T=R.sup.1 and V=R.sup.2:

##STR00032##

[0334] wherein X was a halogen selected from the group consisting of F, Cl, Br, and I. Preferably X was F.

[0335] The individual reaction steps were performed under similar conditions as described in General scheme I for AAV1, AAV2, and AAV3.

Cyclic Voltammetry

[0336] Cyclic voltammograms are measured from solutions having concentration of 10.sup.−3 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/L of tetrabutylammonium hexafluorophosphate). The measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp.sub.2/FeCp.sub.2.sup.+ as internal standard. The HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).

Density Functional Theory Calculation

[0337] Molecular structures are optimized employing the BP86 functional and the resolution of identity approach (RI). Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies are calculated with the B3LYP functional. Def2-SVP basis sets (and an m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.

Photophysical Measurements

[0338] Sample pretreatment: Spin-coating

[0339] Apparatus: Spin150, SPS euro.

[0340] The sample concentration is 0.2 mg/ml, dissolved in toluene/DCM.

[0341] Program: 7-30 sec. at 2000 U/min. After coating, the films are dried at 70° C. for 1 min.

Photoluminescence Spectroscopy and Phosphorescence Spectroscopy

[0342] For the analysis of Phosphorescence and Fluorescence spectroscopy, a fluorescence spectrometer “Fluoromax 4P” from Horiba was used.

[0343] Time-resolved PL spectroscopy in the μs-range and ns-range (FS5)

[0344] Time-resolved PL measurements were performed on a FS5 fluorescence spectrometer from Edinburgh Instruments. Compared to measurements on the HORIBA setup, better light gathering allows for an optimized signal to noise ratio, which makes the FS5 system more favorable especially for transient PL measurements of delayed fluorescence characteristics. The FS5 composed of a xenon lamp providing a broad spectrum. The continuous light source is a 150W xenon arc lamp, selected wavelengths are chosen by a Czerny-Turner monochromator, which is also used to set specific emission wavelengths. The sample emission is directed towards a sensitive R928P photomultiplier tube (PMT), allowing the detection of single photons with a peak quantum efficiency of up to 25% in the spectral range between 200 nm and 870 nm. The detector is a temperature stabilized PMT, providing dark counts below 300 cps (counts per second). Finally, to determine the transient decay lifetime of the delayed fluorescence, a tail fit using three exponential functions is applied. By weighting the specific lifetimes τ.sub.i with their corresponding amplitudes A.sub.i,

[00001]${\tau }_{\mathrm{DF}}={.Math.}_{i=1}^3\frac{A_i{\tau }_i}{A_i}$

[0345] the delayed fluorescence lifetime T.sub.DF is determined.

Photoluminescence Quantum Yield Measurements

[0346] For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0.

[0347] Emission maxima are given in nm, quantum yields CD in % and CIE coordinates as x,y values.

[0348] PLQY is determined using the following protocol:

[0349] Quality assurance: Anthracene in ethanol (known concentration) is used as reference

[0350] Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength

[0351] Measurement

[0352] Quantum yields are measured, for sample, of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

[00002]${\Phi }_{\mathrm{PL}}=\frac{n_{\mathrm{photon}},\mathrm{emitted}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{\int \frac{\lambda }{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(\lambda \right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{sample}}\left(\lambda \right)\right]d\lambda }{\int \frac{\lambda }{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(\lambda \right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{reference}}\left(\lambda \right)\right]d\lambda }$

[0353] wherein n.sub.photon denotes the photon count and Int. denotes the intensity.

Production and Characterization of Optoelectronic Devices

[0354] Optoelectronic devices, such as OLED devices, including organic molecules according to the invention can be produced via vacuum-deposition methods. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %. The total weight-percentage values amount to 100%, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100%.

[0355] The not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current. The OLED device lifetime is extracted from the change of the luminance during operation at constant current density. The LT50 value corresponds to the time, where the measured luminance decreased to 50% of the initial luminance, analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80% of the initial luminance, LT 95 to the time point, at which the measured luminance decreased to 95% of the initial luminance etc.

[0356] Accelerated lifetime measurements are performed (e.g. applying increased current densities). For example, LT80 values at 500 cd/m.sup.2 are determined using the following equation:

[00003]$\mathrm{LT}80\left(500\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}80\left(L_0\right){\left(\frac{L_0}{500\frac{{\mathrm{cd}}^2}{m^2}}\right)}^{1.6}$

[0357] wherein L.sub.0 denotes the initial luminance at the applied current density.

[0358] The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.

[0359] HPLC-MS

[0360] HPLC-MS analysis is performed on an HPLC by Agilent (1260 series) with MS-detector (Thermo LTQ XL).

[0361] For example, a typical HPLC method is as follows: a reverse phase column 3.0 mm×100 mm, particle size 2.7 μm from Agilent (Poroshell 120EC-C18, 3.0×100 mm, 2.7 μm HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) with the following gradients

TABLE-US-00001 Flow rate [ml/min] Time [min] A[%] B[%] C[%] 1.5 30 40 40 30 1.5 45 10 10 80 1.5 50 40 10 80 1.5 51 30 40 30 1.5 55 30 10 30

[0362] using the following solvent mixtures containing 0.1% formic acid:

TABLE-US-00002 Solvent A: H2O (10%) MeCN (90%) Solvent B: H2O (90%) MeCN (10%) Solvent C: THF (50%) MeCN (50%)

[0363] An injection volume of 2 μL from a solution with a concentration of 0.5 mg/mL of the analyte is taken for the measurements.

[0364] Ionization of the probe was performed using an atmospheric pressure chemical ionization (APCI) source either in positive (APCI+) or negative (APCI−) ionization mode or an atmospheric pressure photoionization (APPI) source.

Example 1

[0365] ##STR00033##

[0366] Example 1 was synthesized according to General synthesis scheme I and according to

[0367] AAV3 (27% yield), wherein

##STR00034##

(CAS 869340−02-3) was used as reactant I2 and dimesitylfluoroborane (CAS 436-59-9) as reactant I2-1.

[0368] MS (HPLC-MS), m/z (retention time): 783.45 (15.92 min).

[0369] The emission maximum of example 1 (0.001 mg/mL in dichloromethane (DCM)) is at 464 nm (2.67 eV), the full width at half maximum (FWHM) is 0.24 eV and the CIEy coordinate is 0.17. The onset of the emission spectrum is determined at 2.79 eV.

[0370] The emission maximum of example 1 (1% PMMA) is at 462 nm, the full width at half maximum (FWHM) is 0.26 eV and the CIEy coordinate is 0.17. The onset of the emission spectrum is determined at 2.81 eV.

Example 2

[0371] ##STR00035##

[0372] Example 2 was synthesized according to General synthesis scheme I and according to

[0373] AAV3 (53% yield), wherein

##STR00036##

(CAS 27973-29-1) was used as reactant I2 and dimesitylfluoroborane (CAS 436-59-9) as reactant I2-1.

[0374] MS (HPLC-MS), m/z (retention time): 698.43 (7.42 min).

[0375] The emission maximum of example 2 (0.001 mg/mL in dichloromethane (DCM)) is at 441 nm (2.81 eV) and the CIEy coordinate is 0.06. The onset of the emission spectrum is determined at 2.93 eV.

Example 3

[0376] ##STR00037##

[0377] Example 3 was synthesized according to General synthesis scheme I and according to

[0378] AAV1 wherein

##STR00038##

(CAS 27973-29-1) was used as reactant I0 and

##STR00039##

(CAS 1392512-54-7) as reactant I0-1

[0379] AAV2,

[0380] and AAV3 wherein 1,6-dibromo-3,8-bis(4-fluoro-2,6-dimethylphenyl)pyrene was used as reactant I2 and dimesitylfluoroborane (CAS 436-59-9) as reactant I2-1.

Example 4

[0381] ##STR00040##

[0382] Example 4 was synthesized according to General synthesis scheme I and according to

[0383] AAV1 wherein

##STR00041##

(CAS 27973-29-1) was used as reactant I0 and

##STR00042##

(CAS 1423-27-4) as reactant I0-1

[0384] AAV2,

[0385] AAV3, wherein 1,6-dibromo-3,8-bis(2-(trifuoromethyl) phenyl) pyrene was used as reactant I2 and dimesityfluoroborane (GAS 436-59-9) as reactant I2-1.

Example 5

[0386] ##STR00043##

[0387] Example 5 was synthesized according to General synthesis scheme I and according to

[0388] AAV2a (70% yield), wherein example 2 was used as reactant I1a and

[0389] AAV3a (2% yield), wherein 2,4,6-trimethylphenylboronic acid (CAS 5980-97-2) was used as reactant I2a-1.

[0390] The emission maximum of example 5 (1% PMMA) is at 452 nm, the full width at half maximum (FWHM) is 0.30 eV and the CIEy coordinate is 0.13. The onset of the emission spectrum is determined at 2.88 eV.

Example D1

[0391] Example 1 was tested in the OLED D1, which was fabricated with the following layer structure:

TABLE-US-00003 Layer # Thickness D1 10 100 nm Al 9  2 nm Liq 8  20 nm NBPhen 7  10 nm MAT1 6  40 nm MAT2 (99%):   Example 1 (1%) 5  10 nm MAT3 4  10 nm TCTA 3  40 nm NPB 2  5 nm HAT-CN 1  50 nm ITO Substrate Glass

##STR00044##

[0392] OLED D1 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 8.7%. The emission maximum is at 469 nm with a FWHM of 46 nm at 4.9 V. The corresponding CIEx value is 0.12 and the CIEy value is 0.21. A LT95-value at 1200 cd/m.sup.2 of 7.1 h was determined.

Example D2

[0393] Example 2 was tested in the OLED D2, which was fabricated with the

TABLE-US-00004 Layer # Thickness D2 10 100 nm Al 9  2 nm Liq 8  20 nm NBPhen 7  10 nm MAT1 6  40 nm MAT2 (97%):   Example 2 (3%) 5  10 nm MAT3 4  10 nm TCTA 3  40 nm NPB 2  5 nm HAT-CN 1  50 nm ITO Substrate Glass

[0394] OLED D2 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 7.9%. The emission maximum is at 452 nm with a FWHM of 46 nm at 6.1 V. The corresponding CIEx value is 0.14 and the CIEy value is 0.10. A LT95-value at 1200 cd/m.sup.2 of 7.4 h was determined.

Additional Examples of Organic Molecules of the Invention

[0395] ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068##

##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083##

##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093##