ORGANIC MOLECULES FOR USE IN ORGANIC OPTOELECTRONIC DEVICES

Abstract

The invention relates to an organic molecule, in particular for use in optoelectronic components. According to the invention, the organic molecule has a structure of Formula I

##STR00001##

with
XCN,
D=

##STR00002##

wherein
# is the point of attachment of unit D to one of the phenyl rings shown in Formula I;
Z is a direct bond or is selected from the group consisting of CR.sup.3R.sup.4, CCR.sup.3R.sup.4, CO, CNR.sup.3, NR.sup.3, O, SiR.sup.3R.sup.4, S, S(O), S(O).sub.2;

In each occurrence R.sup.1 and R.sup.2 is the same or different, is H, deuterium, a linear alkyl group having 1 to 5 C atoms, a linear alkenyl or alkynyl group having 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms can be replaced by deuterium or an aromatic ring system having 5 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.6;

and wherein at least one R.sup.a is not H, and
wherein at least one R.sup.2 is H.

Claims

1. An organic molecule, comprising a structure of Formula I ##STR00033## with XCN and D= ##STR00034## wherein # is the point of attachment of unit D to a phenyl ring of the structure according to Formula I; Z is a direct bond or is selected from the group consisting of CR.sup.3R.sup.4, CCR.sup.3R.sup.4, CO, CNR.sup.3, NR.sup.3, O, SiR.sup.3R.sup.4, S, S(O) and S(O).sub.2; in each occurrence R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of: H, deuterium; a linear alkyl group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium; a linear alkenyl or alkynyl group having 2 to 8 C atoms, wherein one or more H atoms can be replaced by deuterium; a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms can be replaced by deuterium; and an aromatic ring system having 5 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.6; in each occurrence R.sup.a, R.sup.3 and R.sup.4 is the same or different and is selected from the group consisting of: H, deuterium, N(R.sup.5).sub.2, OH, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.5; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; in each occurrence R.sup.5 is the same or different and is selected from the group consisting of: H, deuterium, N(R.sup.6).sub.2, OH, Si(R.sup.6).sub.3, B(OR.sup.6).sub.2, OSO.sub.2R.sup.6, CF.sub.3, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.6, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.6, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.6, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.6; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R.sup.6; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R.sup.6; in each occurrence R.sup.6 is the same or different and is selected from the group consisting of: H, deuterium, OH, CF.sub.3, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms, wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms; wherein each of the radicals R.sup.a, R.sup.3, R.sup.4 or R.sup.5 can also form a mono- or polycyclic, aliphatic, aromatic and/or benzoannelated ring system with one or more further radicals R.sup.a, R.sup.3, R.sup.4 or R.sup.5; and wherein at least one R.sup.a is not H, and wherein at least one R.sup.2 is H.

2. The organic molecule according to claim 1, wherein R.sup.1 is H or methyl and R.sup.2 is H.

3. The organic molecule according to claim 1, wherein D comprises a structure of Formula IIa: ##STR00035## wherein # and R.sup.a have the aforestated meanings.

4. The organic molecule according to claim 1, wherein D comprises a structure of Formula IIb: ##STR00036## wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: N(R.sup.5).sub.2, OH, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.5; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and # and R.sup.5 have the aforestated meanings.

5. The organic molecule according to claim 1, wherein D comprises a structure of Formula IIc: ##STR00037## wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: N(R.sup.5).sub.2, OH, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a linear alkenyl or alkynyl group having 2 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in each case be substituted with one or more radicals R.sup.5, wherein one or more non-adjacent CH.sub.2 groups can be replaced 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 and wherein one or more H atoms can be replaced by deuterium, CN, CF.sub.3 or NO.sub.2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted with one or more radicals R.sup.5; an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted with one or more radicals R.sup.5; and a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which can be substituted with one or more radicals; and # and R.sup.5 have the aforestated meanings.

6. The organic molecule according to claim 4, wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: Me, .sup.iPr, .sup.tBu, CN, CF.sub.3; Ph, which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; pyridinyl, which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; pyrimidinyl which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; carbazolyl which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; and N(Ph).sub.2.

7. A method for producing an organic molecule according to claim 1, wherein a in 3 position R.sup.1-substituted and in 4 and 6 position R.sup.2-substituted 2-bromo-5-fluorobenzonitrile is used as the educt.

8. An optoelectronic device comprising an organic molecule according to claim 1.

9. The optoelectronic device according to claim 8, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, 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.

10. A composition comprising: (a) at least one organic molecule according to claim 1, as an emitter and/or host, and (b) on 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.

11. An optoelectronic device comprising the composition according to claim 10.

12. The optoelectronic device according to claim 11, comprising: a substrate, an anode and a cathode, wherein the anode or the cathode are disposed on the substrate, and at least one light-emitting layer, which is disposed between the anode and the cathode and which comprises the composition according to claim 10.

13. (canceled)

14. (canceled)

15. The optoelectronic device according to claim 8, wherein the organic molecule is one of an emitter and an absorber in the optoelectronic component.

16. The optoelectronic device according to claim 15, wherein the proportion of the organic molecule in the emitter or absorber is in the range of 1% to 80%.

17. An optoelectronic device comprising an organic molecule according to claim 2.

18. The optoelectronic device according to claim 16, wherein the organic molecule is one of an emitter and an absorber in the optoelectronic component.

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

20. The organic molecule according to claim 2, wherein both X are CN.

21. The organic molecule according to claim 5, wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: wherein in each occurrence R.sup.b is the same or different and is selected from the group consisting of: Me, .sup.iPr, .sup.tBu, CN, CF.sub.3; Ph, which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; pyridinyl, which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; pyrimidinyl which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; carbazolyl which can in each case be substituted with one or more radicals selected from Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, or Ph; and N(Ph).sub.2.

22. A process for producing an optoelectronic component, comprising processing of the organic molecule according to claim 1 by a vacuum vaporization process or from a solution.

Description

EXAMPLES

General Synthesis Scheme

[0100] ##STR00013##

General Synthesis Specification AAV1:

[0101] ##STR00014##

[0102] 2-bromo-5-fluorobenzonitrile (2.00 equivalent), bis(pinacolato)diboron (1.00 equivalent), pd.sub.2(dba).sub.3 (0.01 equivalent), SPhos (0.04 equivalent) and potassium phosphate tribasic (6.00 equivalent) are stirred into a dioxane/water mixture (ratio 20:1) at 110 C. for 16 hours under nitrogen. The insoluble constituents of the reaction mixture are subsequently filtered off and washed with dioxane. The solvent of the filtrate is removed and the obtained residue is dissolved in dichloromethane, filtered through a small amount of silica gel, the solvent is removed again and the thus obtained raw product is purified by recrystallization from ethanol. The product is obtained as a solid.

General Synthesis Specification AAV2:

[0103] ##STR00015##

[0104] Z1 (1.00 equivalent), the corresponding donor molecule D-H (2.00 equivalent) and potassium phosphate tribasic (4.00 equivalent) are suspended in DMSO under nitrogen and stirred at 110 C. (16 h). The reaction mixture is then added to saturated sodium chloride solution and extracted three times with dichloromethane. The combined organic phases are washed twice with saturated sodium chloride solution, dried over magnesium sulfate, and the solvent is subsequently removed. Lastly, the raw product was purified by recrystallization from toluene. The product is obtained as a solid.

[0105] D-H in particular corresponds to 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), an 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).

Photophysical Measurements

Pretreatment of Optical Glasses

[0106] All glasses (cuvettes and substrates made of quartz glass, diameter: 1 cm) were cleaned after every use: washed three times in each case with dichloromethane, acetone, ethanol, demineralized water, placed in 5% Hellmanex solution for 24 h, thoroughly rinsed with demineralized water. The optical glasses were dried by blowing nitrogen over them.

Sample Preparation, Film: Spin Coating

[0107] Device: Spin150, SPS Euro.

[0108] The sample concentration was equivalent to 10 mg/ml, prepared in toluene or chlorobenzene.

[0109] Program: 1) 3 s at 400 rpm; 2) 20 s at 1000 rpm at 1000 rpm/s. 3) 10 s at 4000 rpm at 1000 rpm/s. After coating, the films were dried on a LHG precision heating plate for 1 min at 70 C. in air.

Photoluminescence Spectroscopy and TCSPC

[0110] Steady-state emission spectroscopy was carried out using a fluorescence spectrometer of the company Horiba Scientific, Model Fluoromax-4, equipped with a 150 W xenon arc lamp, excitation and emission monochromators and a Hamamatsu R928 photomultiplier tube, as well as a Time-Correlated Single Photon Counting (TCSPC) option. The emission and excitation spectra were corrected by means of standard correction curves.

[0111] The emission decay times were likewise measured on this system, using the TCSPC method with the FM-2013 accessories and a TCSPC hub of the company Horiba Yvon Jobin. Excitation sources:

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

[0112] The analysis (exponential fitting) was performed using the DataStation software package and the DAS6 analysis software. The fit was specified with the aid of the Chi-square method

[00001]$c^2=\underset{k=1}{\overset{i}{.Math.}}.Math..Math.\frac{{\left(e_i-o_i\right)}^2}{e_i}$

with e.sub.i: variable predicted by the fit and o.sub.i: measured variable.

Quantum Efficiency Determination

[0113] The measurement of the photoluminescence quantum yield (PLQY) was carried out by means of an Absolute PL Quantum Yield Measurement C9920-03G system of the company Hamamatsu Photonics. Said system consists of a 150 W xenon gas discharge lamp, automatically adjustable Czerny-Turner monochromators (250-950 nm) and an Ulbricht sphere with a high reflectance Spectralon coating (a Teflon derivative), which is connected via a fiber optic cable to a PMA-12 multichannel detector with a BT (back-thinned)-CCD chip having 1024122 pixels (size 2424 m). The analysis of the quantum efficiency and the CIE coordinates was carried out using the software U6039-05 Version 3.6.0.

[0114] The emission maximum is measured in nm, the quantum yield Q is measured in % and the CIE color coordinates are stated as x, y values.

[0115] The photoluminescence quantum yield was determined according to the following protocol:

1) Implementation of quality assurance measures: Anthracene in ethanol at a known concentration serves as the reference material.
2) Determination of the excitation wavelength: The absorption maximum of the organic molecule was first determined and excited with said wavelength.
3) Implementation of the sample measurement:

[0116] The absolute quantum yield of degassed solutions and films was determined under a nitrogen atmosphere.

[0117] The calculation was performed within the system according to the following equation:

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

with the photon number n.sub.photon and the intensity Int.

[0118] Production and characterization of organic electroluminescence devices from the gas phase With the organic molecules according to the invention, OLED devices can be produced by means of vacuum sublimation techniques.

[0119] These not yet optimized OLEDs can be characterized in the usual manner. To do this, the electroluminescence spectra, the external quantum efficiency (measured in %) as a function of the brightness and calculated from the light detected by the photodiode, the electroluminescence spectra and the current are recorded.

Example 1

[0120] ##STR00016##

[0121] Example 1 was produced in accordance with AAV1 (Yield 29%) and AAV2 (Yield 13%).

[0122] Thin layer chromatography: R.sub.f=0.51 (cyclohexane/ethylacetate 5:1)

[0123] FIG. 1 shows the emission spectrum of Example 1 (10% in PMMA). The emission maximum is at 448 nm. The photoluminescence quantum yield (PLQY) is 82% and the full width at half maximum is 0.42 eV. The CIE.sub.x color coordinate is 0.16 and the CIE.sub.y color coordinate is 0.13.

Example 2

[0124] ##STR00017##

[0125] Example 2 was produced in accordance with AAV1 (Yield 29%) and AAV2.

[0126] Thin layer chromatography: R.sub.f=0,12 (cyclohexane/ethylacetate 5:1)

[0127] FIG. 2 shows the emission spectrum of Example 2 (10% in PMMA). The emission maximum is at 491 nm. The photoluminescence quantum yield (PLQY) is 77% and the full width at half maximum is 0.45 eV. The CIE.sub.x color coordinate is 0.21 and the CIE.sub.y color coordinate is 0.38.

Example 3

[0128] ##STR00018##

[0129] Example 3 was produced in accordance with AAV1 (Yield 29%) and AAV2 Yield 83%).

[0130] Thin layer chromatography: R.sub.f=0.51 (cyclohexane/ethylacetate 5:1)

[0131] FIG. 3 shows the emission spectrum of Example 3 (10% in PMMA). The emission maximum is at 520 nm. The photoluminescence quantum yield (PLQY) is 62% and the full width at half maximum is 0.51 eV. The CIE.sub.x color coordinate is 0.31 and the CIE.sub.y color coordinate is 0.49.

Example 4

[0132] ##STR00019##

[0133] Example 4 was produced according to AAV1 and AAV2.

Example 5

[0134] ##STR00020##

[0135] Example 5 was produced in accordance with AAV1 (Yield 29%) and AAV2 (Yield 21%).

[0136] FIG. 4 shows the emission spectrum of Example 5 (10% in PMMA). The emission maximum is at 444 nm. The photoluminescence quantum yield (PLQY) is 91% and the full width at half maximum is 0.42 eV. The CIE.sub.x color coordinate is 0.15 and the CIE.sub.y color coordinate is 0.11.

[0137] Further examples of organic molecules having a structure according to Formula I:

##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032##

FIGURES

[0138] The figures show:

[0139] FIG. 1 Emission spectrum of Example 1 (10% in PMMA).

[0140] FIG. 2 Emission spectrum of Example 2 (10% in PMMA).

[0141] FIG. 3 Emission spectrum of Example 3 (10% in PMMA).

[0142] FIG. 4 Emission spectrum of Example 5 (10% in PMMA).