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 first chemical moiety with a structure of formula (I), —two second chemical moieties with a structure of formula (II), wherein X and Y are at each occurrence independently from another selected from the group consisting of B and N; Z is a direct bond; R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V, R.sup.VI, R.sup.VII, R.sup.VIII, R.sup.IX, and R.sup.X are at each occurrence independently from another selected from the group consisting of the binding site of a single bond linking the first chemical moiety to the second moiety, and R*; R* is at each occurrence independently from another 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, C.sub.1-C.sub.5-alkoxy, C.sub.1-C.sub.5-thioalkoxy, C.sub.2-C.sub.5-alkenyl, C.sub.2-C.sub.5-alkynyl, C.sub.6-C.sub.18-aryl, C.sub.3-C.sub.17-heteroaryl, N(C.sub.6-C.sub.18-aryl).sub.2, N(C.sub.3-C.sub.17-heteroaryl).sub.2; N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); and the dashed lines represent the binding sites of the first chemical moiety to the second chemical moiety.

##STR00001##

Claims

1-15. (canceled)

16. An organic molecule, comprising: a first chemical moiety represented by Formula I: ##STR00069## and a second chemical moiety and a third chemical moiety, each of the second chemical moiety and the third chemical moiety being independently represented by Formula II: ##STR00070## wherein X and Y are at each occurrence independently selected from the group consisting of B and N; R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V, R.sup.VI, R.sup.VII, R.sup.VIII, R.sup.IX, and R.sup.X are each independently selected from the group consisting of: a binding site of a single bond linking the first chemical moiety to the second chemical moiety, a binding site of a single bond linking the first chemical moiety to the third chemical moiety, and R*; R* 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 substituted by deuterium (D), CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms are independently 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 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 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 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, Ph, CN, CF.sub.3 or F; C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents, 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); wherein the dashed lines in Formula II represent the binding sites of the second chemical moiety and the third chemical moiety to the first chemical moiety; Z is a direct bond; o is at each occurrence independently 0 or 1; p is at each occurrence independently 0 or 1; R.sup.2 is at each occurrence independently selected from the group consisting of: hydrogen; deuterium; N(R.sup.5).sub.2; OR.sup.5; Si(R.sup.5).sub.3; B(OR.sup.5).sub.2; OR.sup.5; CF.sub.3; CN; F; Br; I; C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5; R.sup.5 is at each occurrence independently selected from the group consisting of: hydrogen; deuterium; N(R.sup.6).sub.2; OR.sup.6; Si(R.sup.6).sub.3; B(OR.sup.6).sub.2; OR.sup.6; CF.sub.3; CN; F; Br; I; C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; 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 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 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 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 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 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); wherein adjacent groups R.sup.2 are optionally bonded to each other to form an aryl or heteroaryl ring, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents, deuterium, halogen, CN or CF.sub.3; and two atoms from among X and Y in the second chemical moiety and X and Y in the third chemical moiety are B and a remaining two atoms are N; and two adjacent substituents selected from the group consisting of: R.sup.I and R.sup.II, R.sup.II and R.sup.III, and R.sup.IV and R.sup.V represent the binding sites of single bonds linking the first chemical moiety to the second chemical moiety to form a ring, and two adjacent substituents selected from the group consisting of: R.sup.VI and R.sup.VII, R.sup.VII and R.sup.VIII, and R.sup.IX and R.sup.X represent the binding sites of single bonds linking the first chemical moiety to the third chemical moiety to form a ring.

17. The organic molecule according to claim 16, wherein the organic molecule is represented by Formula Ia: ##STR00071## wherein in Formula Ia, m is 0 or 1; n is 0 or 1; and exactly two selected from the two Xs and two Ys in Formula Ia are B and a remaining two selected from the two Xs and two Ys in Formula Ia are N.

18. The organic molecule according to claim 16, wherein the organic molecule is represented by Formula Ib: ##STR00072## wherein in Formula Ib, m is 0 or 1, n is 0 or 1, and exactly two selected from the two Xs and two Ys in Formula Ib are B and a remaining two selected from the two Xs and two Ys in Formula Ib are N.

19. The organic molecule according to claim 16, wherein the second chemical moiety and the third chemical moiety are each independently represented by Formula IIa: ##STR00073##

20. The organic molecule according to claim 16, wherein the second chemical moiety and the third chemical moiety are each independently represented by Formula IIb: ##STR00074##

21. The organic molecule according to claim 16, wherein R* is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, Me, .sup.iPr, .sup.tBu, SiMe.sub.3, SiPh.sub.3, and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, .sup.iPr, .sup.tBu, and Ph.

22. The organic molecule according to claim 16, wherein R.sup.2 is at each occurrence independently selected from the group consisting of: hydrogen, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, carbazolyl, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, triazinyl, which is optionally substituted with one or more substituents independently selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, and N(Ph).sub.2.

23. The organic molecule according to claim 16, wherein o is 1.

24. An optoelectronic device comprising the organic molecule according to claim 16 as a luminescent emitter.

25. The optoelectronic device according to claim 24, wherein the optoelectronic device is 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.

26. A composition, comprising: (a) the organic molecule according to claim 16, as an emitter and/or a host, and (b) an emitter and/or a host material, which differs from the organic molecule, and (c) optionally, a dye and/or a solvent.

27. An optoelectronic device, comprising the composition according to claim 26, wherein the device is 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.

28. The optoelectronic device according to claim 24, comprising: a substrate, an anode, and a cathode, wherein the anode or the cathode is on the substrate, and a light-emitting layer between the anode and the cathode and comprising the organic molecule.

29. A method for producing an optoelectronic device, the method comprising depositing the organic molecule according to claim 16.

30. The method according to claim 29, wherein the depositing of the organic molecule comprises a vacuum evaporation method and/or a solution method.

31. The optoelectronic device according to claim 27, comprising: a substrate, an anode, and a cathode, wherein the anode or the cathode is on the substrate, and a light-emitting layer between the anode and the cathode and comprising the composition.

32. A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 26.

33. The method according to claim 32, wherein the depositing of the composition comprises a vacuum evaporation method and/or a solution method.

Description

EXAMPLES

General Synthesis Scheme I

[1001] General synthesis scheme I provides a synthesis scheme for organic molecules according to the invention wherein R.sup.III=R.sup.VIII; R.sup.IV, R.sup.VII, and R.sup.IX are hydrogen, [1002] adjacent substituents R.sup.V and R.sup.VI, represent the binding sites of single bonds linking the first chemical moiety to the second chemical moiety to form a ring, [1003] and two adjacent substituents R.sup.X and R.sup.I; represent the binding sites of single bonds linking the first chemical moiety to another (i.e., a second) second chemical moiety to form a ring with X═B, Y═N and o and p=0:

##STR00030##

[1004] 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) are 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 is extracted between DCM 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. Instead of a boronic acid ester, a corresponding boronic acid may be used.

General Procedure for Synthesis AAV2:

[1005] ##STR00031##

[1006] I1 (1.00 equivalents) and liquid bromine (4.0 equivalents; CAS 7726-95-6) are stirred under nitrogen atmosphere in anhydrous dimethylformamide (DMF) at room temperature overnight. The reaction mixture is poured into water. The precipitates are filtered off, washed with water and ethanol. The crude product obtained is purified by recrystallization or column chromatography and I2 is obtained as solid.

General Procedure for Synthesis AAV3:

[1007] ##STR00032##

[1008] wherein X.sup.H is a halogen selected from the group consisting of Cl, Br, and I. In certain embodiments, X.sup.H is Cl.

[1009] I2 (1.00 equivalents), I2-1 (2.20 equivalents), Tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.02 equivalents; CAS 51364-51-3), and sodium tert-butoxide (4.00 equivalents, CAS 865-48-5) are stirred under nitrogen atmosphere in dry toluene. Tri-tert-butylphosphine (1 M in toluene, 0.08 equivalents, CAS 13716-12-6) is added and the mixture is stirred at 80° C. until completion. After cooling down to room temperature (RT) the reaction mixture is extracted between DCM 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.

General Procedure for Synthesis AAV4:

[1010] ##STR00033##

wherein X.sup.H is a halogen selected from the group consisting of Cl, Br, and I. In certain embodiments, X.sup.H is Cl.

[1011] I3 (1.00 equivalents), bis(pinacolato)diboron (2.20 equivalents, CAS 73183-34-3), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride (0.05 equivalents; CAS: 72287-26-4), and potassium acetate (KOAc; 4.00 equivalents, CAS 127-08-2) are stirred under nitrogen atmosphere in dioxane at 100° C. overnight. After cooling down to room temperature (RT) the reaction mixture is extracted between DCM 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 is obtained as solid.

General Procedure for Synthesis AAV4:

[1012] ##STR00034##

[1013] I4 (1.00 equivalents) and sodium periodate (4 equivalents, CAS 7790-28-5 are dissolved under nitrogen atmosphere in THF/water (4:1 volume ratio). Hydrochloric acid (2 mol/L, 0.1 eq) is added and the mixture is stirred at room temperature for 24 h. Consequently the reaction mixture is extracted between DCM 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 15 is obtained as solid.

General Procedure for Synthesis AAV5:

[1014] ##STR00035##

[1015] I5 (1.00 equivalents) is dissolved under nitrogen atmosphere in Chlorobenzene. Boron tribromide (4.00 equivalents, CAS 10294-33-4) is added and the mixture is stirred at 100° C. for 2 h. After cooling down to room temperature (RT) water is added and the resulting solid is filtrated and washed with water and methanol. The crude product obtained is purified by recrystallization or column chromatography and I6 is obtained as solid.

General Procedure for Synthesis AAV6:

[1016] ##STR00036##

[1017] I6 (1.00 equivalents) is dissolved under nitrogen atmosphere in chlorobenzene. At 0° C. boron trichloride solution (1 M in heptane, 0.67 equivalents, CAS 10294-34-5) is added and the mixture is stirred at room temperature for 2 h. A solution of an aryl Grignard reagent I6-1 (e. g. 1 M in THF, 6.00 equivalents) is added to the mixture at 0° C. The reaction mixture is stirred at room temperature for 1 h. Consequently the reaction mixture is extracted between DCM 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.

Cyclic Voltammetry

[1018] 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

[1019] 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

[1020] Sample pretreatment: Spin-coating

[1021] Apparatus: Spin150, SPS euro.

[1022] The sample concentration is 0.2 mg/ml, dissolved in Toluene/DCM.

[1023] Program: 7) 30 sec. at 2000 U/min. After coating, the films are tried at 70° C. for 1 min.

Fluorescence Spectroscopy and Phosphorescence Spectroscopy

[1024] For the analysis of Phosphorescence and Photoluminescence spectroscopy, a fluorescence spectrometer “Fluoromax 4P” from Horiba is used.

[1025] Time-Resolved PL Spectroscopy in the μs-Range and ns-Range (FS5)

[1026] 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 favors the FS5 system especially for transient PL measurements of delayed fluorescence characteristics. The FS5 consists of a xenon lamp providing a broad spectrum. The continuous light source is a 150 W 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 to 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]${\tau }_{\mathrm{DF}}={.Math.}_{i=1}^3\frac{A_i{\tau }_i}{A_i}$

[1027] the delayed fluorescence lifetime τ.sub.DF is determined.

[1028] Photoluminescence Quantum Yield Measurements

[1029] 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.

[1030] Emission maxima are given in nm, quantum yields ϕ in % and CIE coordinates as x,y values.

[1031] PLQY is determined using the following protocol: [1032] Quality assurance: Anthracene in ethanol (known concentration) is used as reference [1033] Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength

[1034] Measurement

[1035] Quantum yields are measured, for sample, of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

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

[1036] wherein n.sub.photon denotes the photon count and Int. denotes the intensity.

Production and Characterization of Optoelectronic Devices

[1037] Optoelectronic devices, such as 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%.

[1038] 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, and LT 95 corresponds to the time point, at which the measured luminance decreased to 95% of the initial luminance etc.

[1039] 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]$\mathrm{LT}80\left(500\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}80\left(L_0\right){\left(\frac{L_0}{(500\frac{{\mathrm{cd}}^2}{m^2}}\right)}^{1.6}$

[1040] wherein L.sub.0 denotes the initial luminance at the applied current density.

[1041] The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.

[1042] HPLC-MS

[1043] HPLC-MS analysis is performed on an HPLC by Agilent (1260 series) with MS-detector (Thermo LTQ XL).

[1044] 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

[1045] 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%)

[1046] 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.

[1047] Ionization of the probe is 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

[1048] ##STR00037##

[1049] Example 1 was synthesized according to General synthesis scheme II and according to

[1050] AAV3, AAV4, AAV5 and AAV6 wherein

##STR00038##

(CAS 27973-29-1) was used as reactant I2, 2-chloro-N-phenylbenzenamine (CAS 1205-40-9) as reactant I2-1 and 2,4,6-trimethylphenylmagnesium bromide (1 M in THF, CAS 2633-66-1) as reactant I6-1.

[1051] Additional Examples of Organic Molecules of the Invention

##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066##

SUMMARY

[1052] The invention relates to an organic molecule for optoelectronic devices. According to the invention, the organic molecule has: [1053] a first chemical moiety with a structure of Formula I:

##STR00067## [1054] two second chemical moieties with a structure of Formula II:

##STR00068## [1055] wherein [1056] X and Y are at each occurrence independently from another selected from the group consisting of B and N; [1057] Z is a direct bond; [1058] R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V, R.sup.VI, R.sup.VII, R.sup.VIII, R.sup.IX, and R.sup.X are at each occurrence independently from another selected from the group consisting of [1059] the binding site of a single bond linking the first chemical moiety to the second moiety, and R*; [1060] R* is at each occurrence independently from another selected from the group consisting of [1061] 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, C.sub.1-C.sub.5-alkoxy, C.sub.1-C.sub.5-thioalkoxy, C.sub.2-C.sub.5-alkenyl, C.sub.2-C.sub.5-alkynyl, C.sub.6-C.sub.18-aryl, C.sub.3-C.sub.17-heteroaryl, N(C.sub.6-C.sub.18-aryl).sub.2, N(C.sub.3-C.sub.17-heteroaryl).sub.2; N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); and [1062] the dashed lines represent the binding sites of the first chemical moiety to the second chemical moiety.