ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The invention relates to an organic compound, in particular for the application in optoelectronic devices. According to the invention, the organic compound has a first chemical moiety with a structure of formula I,

##STR00001##

and two second chemical moieties, each independently from another with a structure of formula II,

##STR00002##

wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond;
wherein T, V is selected from the group consisting of R.sup.A and R.sup.1; W, X, Y is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of R.sup.A and R.sup.2; R.sup.A has a structure of Formula Py:

##STR00003##

which is bonded to the structure of Formula I via the position marked by the dotted line; and R.sup.W, R.sup.X, R.sup.Y is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is R.sup.I.

Claims

1.-15. (canceled)

16. An organic molecule, comprising a first chemical moiety comprising a structure of Formula Iaa: ##STR00276## and two second chemical moieties, each independently from another comprising a structure of Formula IIa: ##STR00277## wherein R.sup.D is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, T.sup.## is selected from the group consisting of R.sup.A and R.sup.1, V.sup.## is selected from the group consisting of R.sup.A and R.sup.1, W.sup.## is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of R.sup.A and R.sup.2, X.sup.## is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is R.sup.2, Y.sup.## is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is R.sup.2, wherein exactly one substituent selected from the group consisting of W.sup.##, Y.sup.## and X.sup.## represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties, and wherein exactly one substituent selected from the group consisting of T.sup.##, V.sup.## and W.sup.## is R.sup.A; R.sup.A comprises a structure of Formula Py: ##STR00278## wherein one Q is N and the other Q is CR.sup.Py, wherein the dashed bond represents the binding site of Py to the single bond linking the first chemical moiety and R.sup.A; # represents the binding site of a single bond linking the second chemical moieties to the first chemical moiety; R.sup.1 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.2 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.I is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.Tz is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.Py is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.a is at each occurrence independently from another 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, OS.sub.2R.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.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.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.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.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.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.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.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.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.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.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 from another 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, OSO.sub.2R.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.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.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.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.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-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.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.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.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.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.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.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; and R.sup.6 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh, CF.sub.3, CN, F, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkynyl, wherein one or more hydrogen atoms are optionally, 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); wherein the substituents R.sup.a and/or R.sup.5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R.sup.a and/or R.sup.5.

17. The organic molecule according to claim 16, wherein at each occurrence R.sup.1, R.sup.2 and R.sup.1 is independently from each selected from the group consisting of H, methyl, mesityl, tolyl, and phenyl.

18. The organic molecule according to claim 16, wherein R.sup.Tz and R.sup.Py is independently from each other at each occurrence selected from the group consisting of H, methyl, and phenyl.

19. The organic molecule according to claim 17, wherein R.sup.Tz and R.sup.Py is independently from each other at each occurrence selected from the group consisting of H, methyl, and phenyl.

20. The organic molecule according to claim 16, wherein R.sup.a is at each occurrence independently from another selected from the group consisting of H, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, phenyl (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, CN, CF.sub.3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other 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 from each other 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 from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, and N(Ph).sub.2.

21. The organic molecule according to claim 16, wherein R.sup.a is at each occurrence independently from another selected from the group consisting of H, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, 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, CN, CF.sub.3, and Ph, pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph, and triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph.

22. The organic molecule according to claim 16, wherein R.sup.a is at each occurrence independently from another selected from the group consisting of H, Me, .sup.tBu, 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, CN, CF.sub.3, and Ph, and triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph.

23. The organic molecule according to claim 16, wherein R.sup.a is H at each occurrence.

24. A composition comprising: (a) at least one organic molecule according to claim 16 as an emitter and/or a host; (b) one or more emitter and/or host materials different from the at least one organic molecule according to claim 16, and (c) optionally one or more dyes and/or one or more solvents.

25. An optoelectronic device comprising the organic molecule according to claim 16.

26. The optoelectronic device according to claim 25, 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.

27. The optoelectronic device according to claim 26, 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 disposed between the anode and the cathode and which comprises the organic molecule.

28. An optoelectronic device comprising the organic molecule according to claim 16, 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.

29. An optoelectronic device comprising the organic molecule according to claim 17, 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.

30. The optoelectronic device according to claim 29, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is applied to the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

31. An optoelectronic device comprising the composition according to claim 24.

32. The optoelectronic device according to claim 31, 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.

33. The optoelectronic device according to claim 32, 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 disposed between the anode and the cathode and which comprises the composition.

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

35. A process for producing an optoelectronic device, comprising processing of the composition according to claim 24 by a vacuum evaporation method or from a solution.

Description

EXAMPLES

General Synthesis Scheme I

[0312] ##STR00059## ##STR00060##

General Procedure for Synthesis AAV0:

[0313] ##STR00061##

[0314] Bromofluorobenzene E0 (1.00 equivalent; e.g., 1-bromo-2-fluorobenzene CAS: 1072-85-1, 1-bromo-3-fluorobenzene CAS: 1073-06-9, or 1-bromo-4-fluorobenzene CAS: 460-00-4) the corresponding donor molecule D-H (1.00 equivalents) and tribasic potassium phosphate (3.00 equivalents) are suspended under nitrogen atmosphere in DMSO and stirred at 120 C. (16 h). After cooling to room temperature the reaction mixture is extracted with ethyl acetate/brine. Organic phases are collected, washed with brine and dried over MgSO.sub.4. The solvents are removed under reduced pressure. The crude product E1 is purified by recrystallization or by flash chromatography.

General Procedure for Synthesis AAV1:

[0315] ##STR00062##

[0316] E1 (1.00 equivalent), E1-1 (1.00 equivalent), tris(dibenzylideneacetone)dipalladium(0) Pd.sub.2(dba).sub.3 (0.04 equivalents; CAS 51364-51-3), X-Phos (0.08 equivalents, CAS 564483-18-7) and potassium phosphate (K.sub.3PO.sub.4, 3.00 equivalents) are stirred under nitrogen atmosphere in dry toluene/H2O (10:1) at 100 C. for 16 h. After cooling down to room temperature (RT), the reaction mixture is extracted with ethyl acetate/brine. Organic phase is collected, washed with brine and dried over MgSO.sub.4. The organic solvent is removed, the crude oily product E2 is additionally filtrated through silica filter column to remove rest of catalyst and further purified by recrystallization or by flash chromatography.

General Procedure for Synthesis AAV2:

[0317] ##STR00063##

[0318] E2 (1.00 equivalent), bis-(pinacolato)diboron (1.50 equivalents, CAS 73183-34-3), tris(dibenzylideneacetone)dipalladium(0) Pd.sub.2(dba).sub.3 (0.04 equivalents, CAS 51364-51-3), X-Phos (0.08 equivalents, CAS 564483-18-7) and potassium acetate (KOAc, 3.00 equivalents) are stirred under nitrogen atmosphere in dry toluene at 110 C. for 16 h. After cooling down to room temperature (RT) the reaction mixture is extracted with ethyl acetate/brine. The organic phases are collected, washed with brine and dried over MgSO.sub.4. The organic solvent is removed, the crude oily product is purified by recrystallization or by flash chromatography.

General Procedure for Synthesis AAV3:

[0319] ##STR00064##

[0320] E3 (1.00 equivalent), E3-1 (1.50 equivalent; e.g., 4-chloro-2,6-diphenyl-pyrimidine CAS 29509-91-9 or 2-chloro-4,6-diphenyl-pyrimidine CAS 2915-16-4), tris(dibenzylideneacetone)dipalladium(0) Pd.sub.2(dba).sub.3 (0.06 equivalents, CAS 51364-51-3), tricyclohexylphosphine P(Cy)3 (0.16 equivalents; CAS 2622-14-2), and potassium phosphate (K.sub.3PO.sub.4, 3.00 equivalents) are stirred under nitrogen atmosphere in dry toluene/dioxane/H2O (3:3:1) at 100 C. for 16 h. After cooling down to room temperature (RT) the reaction mixture is extracted with ethyl acetate/brine. Organic phase is collected, washed with brine and dried over MgSO.sub.4. The organic solvent is removed, the crude product is further purified by recrystallization or flash chromatography.

General Procedure for Synthesis AAV4:

[0321] ##STR00065##

[0322] Z0 (1.00 equivalent each), the corresponding donor molecule D-H (1.00 equivalents) and tribasic potassium phosphate (3.00 equivalents) are suspended under nitrogen atmosphere in DMSO and stirred at 120 C. (16 h). After cooling to room temperature the reaction mixture is extracted with ethyl acetate/brine. Organic phases are collected, washed with brine and dried over MgSO.sub.4. The solvents are remove under reduced pressure. The crude product is purified by recrystallization or by flash chromatography.

[0323] In particular, the donor molecule D-H is a 3,6-substituted carbazole (e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g., 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1,8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g., 1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a 2-substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole, 2-tert-butylcarbazole), or a 3-substituted carbazole (e.g., 3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

[0324] Exemplarily, a halogen-substituted carbazole, particularly 3-bromocarbazole, can be used as D-H.

[0325] In a subsequent reaction, a boronic acid ester functional group or boronic acid functional group may be, for example, introduced at the position of the one or more halogen substituents, which was introduced via D-H, to yield the corresponding carbazol-3-ylboronic acid ester or carbazol-3-ylboronic acid, e.g., via the reaction with bis(pinacolato)diboron (CAS No. 73183-34-3). Subsequently, one or more substituents R.sup.a may be introduced in place of the boronic acid ester group or the boronic acid group via a coupling reaction with the corresponding halogenated reactant R.sup.a-Hal, preferably R.sup.aCl and R.sup.aBr.

[0326] Alternatively, one or more substituents R.sup.a may be introduced at the position of the one or more halogen substituents, which was introduced via D-H, via the reaction with a boronic acid of the substituent R.sup.a[R.sup.aB(OH).sub.2] or a corresponding boronic acid ester.

Cyclic Voltammetry

[0327] 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

[0328] 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.

Photophysical Measurements

[0329] Sample pretreatment: Spin-coating
Apparatus: Spin150, SPS euro.

[0330] The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

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 tried at 70 C. for 1 min.

[0331] Photoluminescence spectroscopy and TCSPC (Time-correlated single-photon counting) 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.

[0332] Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

Excitation Sources:

[0333] NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)
NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)
SpectraLED 310 (wavelength: 314 nm)
SpectraLED 355 (wavelength: 355 nm).

[0334] Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.

Photoluminescence Quantum Yield Measurements

[0335] 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.

[0336] Emission maxima are given in nm, quantum yields CD in % and CIE coordinates as x,y values. PLQY is determined using the following protocol: [0337] 1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference [0338] 2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength [0339] 3) Measurement [0340] Quantum yields are measured for sample of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

[00001]${}_{\mathrm{PL}}=\frac{n_{\mathrm{photon}},\mathrm{emited}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{\frac{}{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(\right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{sample}}\left(\right)\right].Math.d.Math.}{\frac{}{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(\right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{reference}}\left(\right)\right].Math.d.Math.}$ [0341] wherein n.sub.photon denotes the photon count and Int. the intensity.

Production and Characterization of Optoelectronic Devices

[0342] 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%.

[0343] 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). Exemplarily LT80 values at 500 cd/m.sup.2 are determined using the following equation:

[00002]$\mathrm{LT}.Math..Math.80.Math.\left(500.Math.\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}.Math..Math.80.Math.\left(L_0\right).Math.{\left(\frac{L_0}{5.Math.0.Math.0.Math.\frac{{\mathrm{cd}}^2}{m^2}}\right)}^{1.6}$

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

[0344] The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.

HPLC-MS:

[0345] HPLC-MS spectroscopy is performed on a HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL). A typical HPLC method is as follows: a reverse phase column 4.6 mm150 mm, particle size 3.5 m from Agilent (ZORBAX Eclipse Plus 95 C18, 4.6150 mm, 3.5 m HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) following gradients:

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:

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%)

[0346] 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.

[0347] Ionization of the probe is performed using an APCI (atmospheric pressure chemical ionization) source either in positive (APCI+) or negative (APCI) ionization mode.

Example 1

[0348] ##STR00066##

[0349] Example 1 was synthesized according to

AAV0 (yield=63%), wherein carbazole was used as reactant D-H and 2-bromofluorobenzene (CAS 1072-85-1) as reactant E0;
AAV1 (yield=92%), wherein 5-chloro-2-fluorobenzeneboronic acid pinacol ester was used as reactant E1-1 and 9-(2-bromophenyl)-9H-carbazole (CAS 902518-11-0) was used as reactant E1;
AAV2 (yield=59%) wherein E2 was used as reactant;
AAV3 (yield=69%), wherein 4-chloro-2,6-diphenyl-pyrimidine (CAS 29509-91-9) was used as reactant E3-1;
AAV4 (yield=69%).
HPLC-MS: 714.64 m/z, 100%

[0350] FIG. 1 depicts the emission spectrum of example 1 (10% by weight in PMMA). The emission maximum (.sub.max) is at 443 nm. The photoluminescence quantum yield (PLQY) is 72% and the full width at half maximum (FWHM) is 0.41 eV.

Example 2

[0351] ##STR00067##

[0352] Example 2 was synthesized according to

AAV0 (yield=63%), wherein carbazole was used as reactant D-H and 2-bromofluorobenzene (CAS 1072-85-1) as reactant E0;
AAV1 (yield=92%), wherein 5-chloro-2-fluorobenzeneboronic acid pinacol ester was used as reactant E1-1 and 9-(2-bromophenyl)-9H-carbazole (CAS 902518-11-0) was used as reactant E1;
AAV2 (yield=59%) wherein E2 was used as reactant;
AAV3 (yield=69%), wherein 4-chloro-2,6-diphenyl-pyrimidine (CAS 29509-91-9) was used as reactant E3-1;
AAV4 (yield=64%).

[0353] HPLC-MS: 866.84 m/z, 100%

[0354] FIG. 2 depicts the emission spectrum of example 2 (10% by weight in PMMA). The emission maximum (.sub.max) is at 454 nm. The photoluminescence quantum yield (PLQY) is 82% and the full width at half maximum (FWHM) is 0.42 eV.

Example 3

[0355] ##STR00068##

[0356] Example 3 was synthesized according to

AAV0 (yield=63%), wherein carbazole was used as reactant D-H and 2-bromofluorobenzene (CAS 1072-85-1) as reactant E0;
AAV1 (yield=92%), wherein 5-chloro-2-fluorobenzeneboronic acid pinacol ester was used as reactant E1-1 and 9-(2-bromophenyl)-9H-carbazole (CAS 902518-11-0) was used as reactant E1;
AAV2 (yield=59%) wherein E2 was used as reactant;
AAV3 (yield=74%), wherein 4-chloro-2-(2-dibenzofuryl)-6-phenyl-pyrimidine was used as reactant E3-1;
AAV4 (yield=57%).

[0357] HPLC-MS: 955.28 m/z, 100%

[0358] FIG. 3 depicts the emission spectrum of example 3 (10% by weight in PMMA). The emission maximum (.sub.max) is at 453 nm. The photoluminescence quantum yield (PLQY) is 81% and the full width at half maximum (FWHM) is 0.40 eV.

Example 4

[0359] ##STR00069##

[0360] Example 4 was synthesized according to

AAV0 (yield=63%), wherein carbazole was used as reactant D-H and 2-bromofluorobenzene (CAS 1072-85-1) as reactant E0;
AAV1 (yield=92%), wherein 5-chloro-2-fluorobenzeneboronic acid pinacol ester was used as reactant E1-1 and 9-(2-bromophenyl)-9H-carbazole (CAS 902518-11-0) was used as reactant E1;
AAV2 (yield=59%) wherein E2 was used as reactant;
AAV3 (yield=69%), wherein 4-chloro-2,6-diphenyl-pyrimidine (CAS 29509-91-9) was used as reactant E3-1;
AAV4 (yield=53%).

[0361] HPLC-MS: 879.55 m/z, 100%

[0362] FIG. 4 depicts the emission spectrum of example 4 (10% by weight in PMMA). The emission maximum (.sub.max) is at 444 nm. The photoluminescence quantum yield (PLQY) is 74% and the full width at half maximum (FWHM) is 0.45 eV.

Additional Examples of Organic Molecules of the Invention

[0363] ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110##

##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163##

##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193##

##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222##

##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275##

FIGURES

[0364] FIG. 1 Emission spectrum of example 1 (10% by weight) in PMMA.

[0365] FIG. 2 Emission spectrum of example 2 (10% by weight) in PMMA.

[0366] FIG. 3 Emission spectrum of example 3 (10% by weight) in PMMA.

[0367] FIG. 4 Emission spectrum of example 4 (10% by weight) in PMMA.