Organic molecules for optoelectronic devices

Abstract

An organic molecule having a structure of Formula I: ##STR00001##
for the application in optoelectronic devices.

Claims

1. An organic molecule according to one of molecules below: ##STR00045##

2. A composition comprising: (a) at least one organic molecule according to claim 1 as an emitter and/or host; (b) one or more emitter and/or host materials different from the at least one organic molecule according to claim 1, and (c) optionally one or more dyes and/or one or more solvents.

3. An optoelectronic device comprising the organic molecule according to claim 1.

4. The optoelectronic device according to claim 3, wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

5. The optoelectronic device according to claim 3, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is disposed on the substrate; and at least one light-emitting layer arranged between the anode and the cathode and which comprises the organic molecule.

6. An optoelectronic device comprising the organic molecule according to claim 1, wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.

7. An optoelectronic device comprising the organic molecule according to claim 1, wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

8. The optoelectronic device according to claim 7, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is disposed on the substrate; and at least one light-emitting layer arranged between the anode and the cathode and which comprises the organic molecule.

9. An optoelectronic device comprising the composition according to claim 2.

10. The optoelectronic device according to claim 9, wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

11. The optoelectronic device according to claim 9, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is disposed on the substrate; and at least one light-emitting layer arranged between the anode and the cathode and which comprises the composition.

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

Description

EXAMPLES

(1) General synthesis scheme I

(2) General synthesis scheme I provides a synthesis scheme for organic molecules according to the invention wherein R.sup.I=R.sup.IV, and R.sup.II=R.sup.III:

(3) ##STR00009## ##STR00010##
General procedure for synthesis AAV1:

(4) ##STR00011##

(5) E1 (1.00 equivalents), E2 (2.20 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.02 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.08 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 6.00 equivalents) are stirred under nitrogen atmosphere in toluene at 80? C. for 2 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I1 is obtained as solid.

(6) General procedure for synthesis AAV2:

(7) ##STR00012##

(8) I1 (1.00 equivalents), 1-Bromo-3,5-diphenylbenzene (2.20 equivalents, CAS: 103068-20-8), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.02 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (0.08 equivalents, P(.sup.tBu).sub.3, CAS: 13716-12-6) and sodium tert-butoxide (NaO.sup.tBu; 5.00 equivalents) are stirred under nitrogen atmosphere in toluene at 100? C. for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I2 is obtained as solid.

(9) General procedure for synthesis AAV3:

(10) ##STR00013##

(11) After dissolving I2 (1 equivalent) under nitrogen atmosphere in THF and cooling to ?20? C., N,N,N,N-tetramethylethylenediamine (4 equivalents, CAS: 110-18-9) is added. Subsequently, sec-BuLi (2 equivalents, CAS: 598-30-1) is added and the reaction mixture is stirred at 0? C. After complete lithiation, the reaction is quenched and 1,3,2-dioxaborolane (2 equivalents, CAS: 61676-62-8) is added and the reaction mixture is stirred under reflux at 70? C. for 2 h. After cooling down to room temperature (rt), the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I3 is obtained as solid.

(12) General procedure for synthesis AAV4:

(13) ##STR00014##

(14) I3 (1 equivalent), N,N-diisopropylethylamine (10 equivalents, CAS: 7087-68-5) and AlCl.sub.3 (10 equivalents, CAS: 7446-70-0) are stirred under nitrogen atmosphere in chlorobenzene at 120? C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and P1 is obtained as solid.

(15) General Synthesis Scheme II

(16) General synthesis scheme I provides a synthesis scheme for organic molecules according to the invention, wherein R.sup.I=R.sup.IV, and R.sup.II=R.sup.III:

(17) ##STR00015## ##STR00016##

(18) The first two steps of the general synthesis scheme II are conducted accordingly to AAV1 and AAV2, respectively. The third step is conducted as described in AAV5:

(19) General procedure for synthesis AAV5:

(20) ##STR00017##

(21) I2 (1.00 equivalents) is dissolved in tert-butylbenzene under nitrogen atmosphere and the solution is cooled to ?30? C. A solution of tert-butyllithium (BuLi) (2.20 equivalents, CAS: 594-19-4) is added dropwise and the reaction mixture is allowed to warm up to 0? C. After stirring for 120 minutes at 60? C., the solvent of the .sup.tBuLisolution and byproducts are removed under reduced pressure and the reaction mixture is cooled again to ?30? C. A solution of boron tribromide (BBr.sub.3, CAS: 10294-33-4, 2.00 equivalents) is added dropwise, the cooling bath is removed and the reaction mixture is allowed to warm to room temperature (rt). After stirring for 30 minutes at rt, the reaction mixture is cooled to 0? C. and N,N-diisopropylethylamine (CAS: 7087-68-5, 3.00 equivalents) is added. The reaction mixture is allowed to warm to rt and then heated at reflux at 120? C. for 3 h. Subsequently, the reaction mixture is poured into water and the resulting precipitate is filtered and washed with a minimum amount of ethyl acetate to obtain P1 as a solid product. P1 can be further purified by recrystallization or by flash chromatography.

(22) General Synthesis Scheme III

(23) General synthesis scheme I provides a synthesis scheme for organic molecules according to the invention where the limitations of scheme I and II (i.e. R.sup.I=R.sup.IV and R.sup.II=R.sup.III) do not exist.

(24) ##STR00018## ##STR00019##
General procedure for synthesis AAV6:

(25) ##STR00020##

(26) 1-Bromo-3,5-diphenylbenzene (1 equivalents, CAS: 103068-20-8), E2 (2.20 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.02 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 3.00 equivalents) are stirred under nitrogen atmosphere in toluene at 80? C. for 5 h.

(27) After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and 14.1 is obtained as solid.

(28) General procedure for synthesis AAV7:

(29) ##STR00021##

(30) 1-Bromo-3,5-diphenylbenzene (1 equivalents, CAS: 103068-20-8), E2.1 (2.20 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.02 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.02 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 3.00 equivalents) are stirred under nitrogen atmosphere in toluene at 80? C. for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and 14.2 is obtained as solid.

(31) General procedure for synthesis AAV8:

(32) ##STR00022##

(33) E3 (1.00 equivalents), 14.1 (1.10 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.02 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 3.00 equivalents) are stirred under nitrogen atmosphere in toluene at 80? C. for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I5 is obtained as solid.

(34) General procedure for synthesis AAV9:

(35) ##STR00023##

(36) I4.2 (1.00 equivalents), I5 (1.10 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.02 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 3.00 equivalents) are stirred under nitrogen atmosphere in toluene at 110? C. for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I6 is obtained as solid.

(37) The last synthesis step of the general scheme III from I6 to P2 is carried out under similar conditions as described in AAV5.

(38) Cyclic Voltammetry

(39) 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).

(40) Density Functional Theory Calculation

(41) 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 a m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.

(42) Photophysical Measurements

(43) Sample pretreatment: Spin-coating

(44) Apparatus: Spin150, SPS euro.

(45) The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

(46) Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 s at 4000 U/min at 1000 Upm/s. After coating, the films are dried at 70? C. for 1 min.

(47) Photoluminescence spectroscopy and Time-Correlated Single-Photon Counting (TCSPC) Steady-state emission spectroscopy is measured by a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.

(48) Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

(49) Excitation Sources:

(50) NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

(51) NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

(52) SpectraLED 310 (wavelength: 314 nm)

(53) SpectraLED 355 (wavelength: 355 nm).

(54) Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.

(55) Photoluminescence Quantum Yield Measurements

(56) 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-C.sub.5 version 3.6.0.

(57) Emission maxima are given in nm, quantum yields D in % and CIE coordinates as x,y values. PLQY is determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference 2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength 3) Measurement

(58) Quantum yields are measured, for sample, of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

(59) ${?}_{PL}=\frac{n_{\mathrm{photon}},\mathrm{emited}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{?\frac{?}{hc}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(?\right)-In{t}_{\mathrm{absorbed}}^{\mathrm{sample}}\left(?\right)\right]d?}{?\frac{?}{hc}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(?\right)-In{t}_{\mathrm{absorbed}}^{\mathrm{reference}}\left(?\right)\right]d?}$
wherein n.sub.photon denotes the photon count and Int. the intensity.
Production and characterization of optoelectronic devices

(60) Optoelectronic devices, in particular OLED devices, comprising 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%.

(61) 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. 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:

(62) $\mathrm{LT}80\left(500\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}80\left(L_0\right){\left(\frac{L_0}{500\frac{c{d}^2}{m^2}}\right)}^{1.6}$
wherein L.sub.0 denotes the initial luminance at the applied current density.

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

(64) HPLC-MS

(65) HPLC-MS analysis is performed on an HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL).

(66) Exemplarly a typical HPLC method is as follows: a reverse phase column 4.6 mm?150 mm, particle size 3.5 ?m from Agilent (ZORBAX Eclipse Plus 95A C18, 4.6?150 mm, 3.5 ?m HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) following gradients

(67) TABLE-US-00001 Flow rate [ml/min] Time [min] A [%] B [%] C [%] 2.5 0 40 50 10 2.5 5 40 50 10 2.5 25 10 20 70 2.5 35 10 20 70 2.5 35.01 40 50 10 2.5 40.01 40 50 10 2.5 41.01 40 50 10
using the following solvent mixtures:

(68) TABLE-US-00002 Solvent A: H.sub.2O (90%) MeCN (10%) Solvent B: H.sub.2O (10%) MeCN (90%) Solvent C: THF (50%) MeCN (50%)

(69) An injection volume of 5 ?L from a solution with a concentration of 0.5 mg/mL of the analyte is taken for the measurements.

(70) Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source either in positive (APCI+) or negative (APCI?) ionization mode.

Example 1

(71) ##STR00024##

(72) Example 1 was synthesized according to

(73) AAV1 (75% yield), wherein 1,3-Dibromo-2-chlorobenzene (CAS 19230-27-4) was used as reactant E1 and aniline (CAS 62-53-3) as E2;

(74) AAV2 (69% yield);

(75) AAV3 (41% yield);

(76) and AAV4 (34% yield).

(77) MS (HPLC-MS), m/z (retention time): 725.50 (9.62 min).

(78) The emission maximum of example 1 (5% by weight in PMMA) is at 457 nm, the full width at half maximum (FWHM) is 0.21 eV, the CIEy coordinate is 0.11 and the PLQY is 74%. The onset of the emission spectrum is determined at 2.84 eV.

Example 2

(79) ##STR00025##

(80) Example 2 was synthesized according to

(81) AAV1 (95% yield), wherein 1,3-Dibromo-2-chlorobenzene (CAS 19230-27-4) was used as reactant E1 and 4-Aminobiphenyl (CAS 92-67-1) as E2;

(82) AAV2 (89% yield);

(83) and AAV5 (6% yield).

(84) MS (HPLC-MS), m/z (retention time): 877.4 (12.6 min).

(85) The emission maximum of example 2 (5% by weight in PMMA) is at 475 nm, the full width at half maximum (FWHM) is 0.20 eV, the CIEy coordinate is 0.24 and the PLQY is 70%. The onset of the emission spectrum is determined at 2.73 eV.

Example 3

(86) ##STR00026##

(87) Example 3 was synthesized according to

(88) AAV1 (94% yield), wherein 1,3-Dibromo-2-chlorobenzene (CAS 19230-27-4) was used as reactant E1 and 3-Aminobiphenyl (CAS 2243-47-2) as E2;

(89) AAV2 (70% yield);

(90) and AAV5 (24% yield).

(91) MS (HPLC-MS), m/z (retention time): 877.5 (7.44 min).

(92) The emission maximum of example 3 (5% by weight in PMMA) is at 478 nm, the full width at half maximum (FWHM) is 0.19 eV, the CIEy coordinate is 0.28 and the PLQY is 84%. The onset of the emission spectrum is determined at 2.72 eV.

Example 4

(93) ##STR00027##

(94) Example 4 was synthesized according to

(95) AAV1 (62% yield), wherein 4-chloro-3,5-dibromotoluene (CAS 202925-C.sub.5-1) was used as reactant E1 and aniline (CAS 62-53-3) as E2;

(96) AAV2 (81% yield);

(97) and AAV5 (20% yield).

(98) MS (HPLC-MS), m/z (retention time): 739.5 (11.04 min).

(99) The emission maximum of example 4 (5% by weight in PMMA) is at 454 nm, the full width at half maximum (FWHM) is 0.20 eV, the CIEy coordinate is 0.10 and the PLQY is 61%. The onset of the emission spectrum is determined at 2.85 eV.

Example 5

(100) ##STR00028##

(101) Example 5 was synthesized according to

(102) AAV1 (87% yield), wherein 4-chloro-3,5-dibromotoluene (CAS 202925-C.sub.5-1) was used as reactant E1 and 4-tert-butylaniline (CAS 769-92-6) as E2;

(103) AAV2 (81% yield);

(104) and AAV5 (16% yield).

(105) MS (HPLC-MS), m/z (retention time): 851.8 (10.2 min).

(106) The emission maximum of example 5 (5% by weight in PMMA) is at 457 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.11 and the PLQY is 59%. The onset of the emission spectrum is determined at 2.83 eV.

Example 6

(107) ##STR00029##

(108) Example 6 was synthesized according to

(109) AAV1 (91% yield), wherein 1,3-Dibromo-2-chlorobenzene (CAS 19230-27-4) was used as reactant E1 and 4-tert-butylaniline (CAS 769-92-6) as E2;

(110) AAV2 (99% yield);

(111) and AAV5 (20% yield).

(112) MS (HPLC-MS), m/z (retention time): 837.8 (10.2 min).

(113) The emission maximum of example 6 (5% by weight in PMMA) is at 461 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.10 and the PLQY is 73%. The onset of the emission spectrum is determined at 2.81 eV.

Example D1

(114) Example 1 was tested in the OLED D1, which was fabricated with the following layer structure:

(115) TABLE-US-00003 Layer # Thickness D1 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT1 5 20 nm MAT2 (99%): Example 1 (1%) 4 10 nm MAT3 3 50 nm MAT4 2 7 nm HAT-CN 1 50 nm ITO Substrate Glass 0

(116) Device D1 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 7.9%. The emission maximum is at 458 nm with a FWHM of 28 nm at 3.54 V. The corresponding CIEy value is 0.07.

Example D2

(117) Example 4 was tested in the OLED D2, which was fabricated with the following layer structure:

(118) TABLE-US-00004 Layer # Thickness D2 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT1 5 20 nm MAT2 (99%): Example 4 (1%) 4 10 nm MAT5 3 50 nm MAT4 2 7 nm HAT-CN 1 50 nm ITO Substrate Glass

(119) Device D2 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 9.8%. The emission maximum is at 456 nm with a FWHM of 26 nm at 3.55 V. The corresponding CIEy value is 0.06.

Example D3

(120) Example 5 was tested in the OLED D3, which was fabricated with the following layer structure:

(121) TABLE-US-00005 Layer # Thickness D3 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT1 5 20 nm MAT2 (99%): Example 5 (1%) 4 10 nm MAT3 3 50 nm MAT4 2 7 nm HAT-CN 1 50 nm ITO Substrate Glass

(122) Device D3 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 7.8%. The emission maximum is at 458 nm with a FWHM of 28 nm at 3.55 V. The corresponding CIEy value is 0.07.

Example D4

(123) Example 6 was tested in the OLED D4, which was fabricated with the following layer structure:

(124) TABLE-US-00006 Layer # Thickness D4 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT1 5 20 nm MAT2 (99%): Example 6 (1%) 4 10 nm MAT5 3 50 nm MAT4 2 7 nm HAT-CN 1 50 nm ITO Substrate Glass

(125) Device D4 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 10.2%. The emission maximum is at 462 nm with a FWHM of 26 nm at 3.43 V. The corresponding CIEy value is 0.08.

Additional Examples of Organic Molecules of the Invention

(126) ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044##

(127) Although illustrative embodiments of the present invention have been described herein with reference to the accompanying drawings, it is to be understood that the invention is not limited to those precise embodiments, and that various other changes and modifications may be made by one skilled in the art without departing from the scope or spirit of the invention.