ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The disclosure pertains to an organic molecule for use in optoelectronic devices. The organic molecule has a structure of Formula I:

##STR00001## wherein X is selected from the group consisting of a direct bond, NR.sup.1, O, S, SiR.sup.1R.sup.2 and CR.sup.1R.sup.2; Y is selected from the group consisting of a direct bond, NR.sup.3, O, S, SiR.sup.3R.sup.4 and CR.sup.3R.sup.4; and R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each independently selected from the group consisting of: hydrogen, deuterium, N(R.sup.5).sub.2, OR.sup.5, SR.sup.5, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, halogen, C.sub.1-C.sub.40-alkyl, C.sub.1-C.sub.40-alkoxy, C.sub.1-C.sub.40-thioalkoxy, C.sub.2-C.sub.40-alkenyl, C.sub.2-C.sub.40-alkynyl, C.sub.6-C.sub.60-aryl, and C.sub.3-C.sub.57-heteroaryl.

Claims

1.-15. (canceled)

16. An organic molecule, comprising a structure represented by Formula I: ##STR00256## wherein in Formula I, X is selected from the group consisting of a direct bond, NR.sup.1, O, S, SiR.sup.1R.sup.2 and CR.sup.1R.sup.2; Y is selected from the group consisting of a direct bond, NR.sup.3, O, S, SiR.sup.3R.sup.4 and CR.sup.3R.sup.4; R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are at each occurrence independently selected from the group consisting of: hydrogen, deuterium, N(R.sup.5).sub.2, OR.sup.5, SR.sup.5, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, halogen, 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; wherein adjacent groups R.sup.5 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; wherein X and Y do not both represent a direct bond; R.sup.5 is at each occurrence independently from one another selected from the group consisting of: hydrogen, deuterium, N(R.sup.6).sub.2, OR.sup.6, SR.sup.6, Si(R.sup.6).sub.3, B(OR.sup.6).sub.2, OSO.sub.2R.sup.6, CF.sub.3, CN, halogen, 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 Re 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 Re 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)(Re), 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; wherein adjacent groups R.sup.6 are optionally bonded to each other and 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; R.sup.6 is at each occurrence independently from one another selected from the group consisting of: hydrogen, deuterium, halogen, OPh, SPh, CF.sub.3, CN, 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 each independently substituted by deuterium, halogen, CN, or CF.sub.3, C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms are each independently substituted by deuterium, halogen, CN, or CF.sub.3, C.sub.1-C.sub.5-thioalkoxy, wherein optionally one or more hydrogen atoms are each independently substituted by deuterium, halogen, CN, or CF.sub.3, C.sub.2-C.sub.5-alkenyl, wherein optionally one or more hydrogen atoms are each independently substituted by deuterium, halogen, CN, or CF.sub.3, C.sub.2-C.sub.5-alkynyl, wherein optionally one or more hydrogen atoms are each independently substituted by deuterium, halogen, CN, or CF.sub.3, 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); 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, R.sup.X, R.sup.XI, R.sup.XII, R.sup.XIII, R.sup.XIV, R.sup.XV, and R.sup.XVI are each independently selected from the group consisting of: hydrogen, deuterium, N(R.sup.7).sub.2, OR.sup.7, SR.sup.7, Si(R.sup.7).sub.3, B(OR.sup.7).sub.2, OSO.sub.2R.sup.7, CF.sub.3, CN, halogen, C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.7 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.7C═CR.sup.7, C≡C, Si(R.sup.7).sub.2, Ge(R.sup.7).sub.2, Sn(R.sup.7).sub.2, C═O, C═S, C═Se, C═NR.sup.1, P(═O)(R.sup.7), SO, SO.sub.2, NR.sup.7, O, S or CONR.sup.7, C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.7 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.7C═CR.sup.7, C≡C, Si(R.sup.7).sub.2, Ge(R.sup.7).sub.2, Sn(R.sup.7).sub.2, C═O, C═S, C═Se, C═NR.sup.1, P(═O)(R.sup.7), SO, SO.sub.2, NR.sup.7, O, S or CONR.sup.7, C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.7 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.7C═CR.sup.7, C≡C, Si(R.sup.7).sub.2, Ge(R.sup.7).sub.2, Sn(R.sup.7).sub.2, C═O, C═S, C═Se, C═NR.sup.1, P(═O)(R.sup.7), SO, SO.sub.2, NR.sup.7, O, S or CONR.sup.7, C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.7 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.7C═CR.sup.7, C≡C, Si(R.sup.7).sub.2, Ge(R.sup.7).sub.2, Sn(R.sup.7).sub.2, C═O, C═S, C═Se, C═NR.sup.1, P(═O)(R.sup.7), SO, SO.sub.2, NR.sup.7, O, S or CONR.sup.7, C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.7 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.7C═CR.sup.7, C≡C, Si(R.sup.7).sub.2, Ge(R.sup.7).sub.2, Sn(R.sup.7).sub.2, C═O, C═S, C═Se, C═NR.sup.1, P(═O)(R.sup.7), SO, SO.sub.2, NR.sup.7, O, S or CONR.sup.7, C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.7, and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.7; wherein adjacent groups R.sup.I to R.sup.IV are optionally bonded to each other and 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; wherein adjacent groups R.sup.V to R.sup.VIII are optionally bonded to each other and 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; wherein adjacent groups R.sup.IX to R.sup.XII are optionally bonded to each other and 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; wherein adjacent groups R.sup.XIII to R.sup.XVI are optionally bonded to each other and 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; R.sup.7 is selected from the group consisting of: hydrogen, deuterium, N(R.sup.8).sub.2, OR.sup.8, SR.sup.8, Si(R.sup.8).sub.3, B(ORB).sub.2, OSO.sub.2R.sup.8, CF.sub.3, CN, halogen, C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.8 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.8C═CR.sup.8, C≡C, Si(R.sup.8).sub.2, Ge(R.sup.8).sub.2, Sn(R.sup.8).sub.2, C═O, C═S, C═Se, C═NR.sup.8, P(═O)(R.sup.8), SO, SO.sub.2, NR.sup.8, O, S or CONR.sup.8, C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.8 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.8C═CR.sup.8, C≡C, Si(R.sup.8).sub.2, Ge(R.sup.8).sub.2, Sn(R.sup.8).sub.2, C═O, C═S, C═Se, C═NR.sup.8, P(═O)(R.sup.8), SO, SO.sub.2, NR.sup.8, O, S or CONR.sup.8, C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents Re and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.8C═CR.sup.6, C≡C, Si(R.sup.8).sub.2, Ge(R.sup.8).sub.2, Sn(R.sup.8).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.8, O, S or CONR.sup.8, C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents Re and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.8C═CR.sup.8, C≡C, Si(R.sup.8).sub.2, Ge(R.sup.8).sub.2, Sn(R.sup.8).sub.2, C═O, C═S, C═Se, C═NR.sup.8, P(═O)(R.sup.8), SO, SO.sub.2, NR.sup.8, O, S or CONR.sup.8, C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents Re 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.8).sub.2, Ge(R.sup.8).sub.2, Sn(R.sup.8).sub.2, C═O, C═S, C═Se, C═NR.sup.8, P(═O)(R.sup.8), SO, SO.sub.2, NR.sup.8, O, S or CONR.sup.8, C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents Re; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents Re; R.sup.8 is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, halogen, OPh, SPh, CF.sub.3, CN, 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 thereof are each independently substituted by deuterium, halogen, CN, or CF.sub.3, C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms thereof are each independently substituted by deuterium, halogen, CN, or CF.sub.3, C.sub.1-C.sub.5-thioalkoxy, wherein optionally one or more hydrogen atoms thereof are each independently substituted by deuterium, halogen, CN or CF.sub.3, C.sub.2-C.sub.5-alkenyl, wherein optionally one or more hydrogen atoms thereof are each independently substituted by deuterium, halogen, CN, or CF.sub.3, C.sub.2-C.sub.5-alkynyl, wherein optionally one or more hydrogen atoms thereof are each independently substituted by deuterium, halogen, CN, or CF.sub.3, 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.1-aryl); wherein the substituents R.sup.1, R.sup.2, R.sup.XIII, R.sup.XIV, R.sup.XV, or R.sup.XVI independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents selected from the group consisting of R.sup.1, R.sup.2, R.sup.XIII, R.sup.XIV, R.sup.XV, and R.sup.XVI; and wherein the substituents R.sup.3, R.sup.4, R.sup.IX, R.sup.X, R.sup.XI, or R.sup.XII independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents selected from the group consisting of R.sup.3, R.sup.4, R.sup.IX, R.sup.X, R.sup.XI, and R.sup.XII.

17. The organic molecule according to claim 16, wherein the organic molecule comprises a structure represented by Formula Ia: ##STR00257## wherein in Formula Ia, X.sup.2 is selected from the group consisting of N, SiR.sup.2 and C—R.sup.2; ring a represents: a C.sub.6-C.sub.18-aryl ring, wherein optionally one or more hydrogen atoms thereof are each independently substituted by R.sup.5; or a C.sub.3-C.sub.7-heteroaryl ring, wherein optionally one or more hydrogen atoms thereof are each independently substituted by R.sup.5, and Z is selected from the group consisting of a direct bond, NR.sup.7, O, S, Si(R.sup.7).sub.2 and C(R.sup.7).sub.2.

18. The organic molecule according claim 17, wherein the molecule comprises a structure represented by Formula Ib: ##STR00258##

19. The organic molecule according to claim 16, wherein R.sup.V and R.sup.XII do not both represent hydrogen.

20. The organic molecule according to claim 17, wherein at least one of Y and Z is a direct bond.

21. The organic molecule according to claim 16, wherein R.sup.V, R.sup.VI, R.sup.VII, R.sup.VIII, R.sup.IX, R.sup.X, R.sup.XI and R.sup.XII are each independently selected from the group consisting of: hydrogen, deuterium, halogen, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, SiMe.sub.3, SiPh.sub.3, OPh, CMe.sub.2Ph, N(Ph).sub.2, and Ph, which is optionally substituted with one or more substituents each independently selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, and Ph; wherein the Ph in N(Ph).sub.2, OPh and CMe.sub.2Ph is optionally bonded to at least one group selected from groups R.sup.V to R.sup.XII positioned adjacent thereto to form an aryl or heteroaryl ring.

22. The organic molecule according to claim 16, wherein R.sup.V═R.sup.XII and/or R.sup.X═R.sup.VII.

23. The organic molecule according to claim 17, wherein X.sup.2═N.

24. A composition, comprising: (a) an 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.

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

26. The optoelectronic device according to claim 25, wherein the optoelectronic device is selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser, and down-conversion element.

27. The optoelectronic device according to claim 25, comprising: a substrate, an anode, and a cathode, wherein the anode or the cathode is disposed on the substrate, and a light-emitting layer, which is arranged between the anode and the cathode and which comprises the organic molecule.

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

29. An optoelectronic device, comprising the composition according to claim 24.

30. The optoelectronic device according to claim 29, wherein the optoelectronic device is selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED-sensor, organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser, and down-conversion element.

31. The optoelectronic device according to claim 29, comprising: a substrate, an anode, and a cathode, wherein the anode or the cathode is disposed on the substrate, and a light-emitting layer, which is arranged between the anode and the cathode and which comprises the composition.

32. A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 24 by a vacuum evaporation method or from a solution.

Description

EXAMPLES

[0572] ##STR00069##

##STR00070##

##STR00071##

General Procedure for Synthesis AAV1:

[0573] ##STR00072##

[0574] Under N2 atmosphere, a 2-necked flask equipped with a reflux condenser is charged with E1 (1.0 equiv.), chlorobenzene (100 mL) and subsequently boron tribromide [10294-33-4] (3.5 equiv.). After the mixture was stirred at 100° C. for 2 hours, the reaction was quenched by adding water (50 mL) at 0° C. The precipitate was filtered and dried to obtain the corresponding product P1 as a solid that is further used without further purification.

General procedure for synthesis AAV2:

##STR00073##

[0575] Under N2 atmosphere, a two-neck flask is charged with P1 (1.0 equiv.) and chlorobenzene (100 mL) and the mixture was degassed for 10 min. Boron trichloride [10294-34-5] (0.5 equiv.) was added at 0° C. and the mixture was allowed to warm up to room temperature and stirred for 2 hours. Under N2 atmosphere, a second two-neck flask was charged with E2 (3.0 equiv.) and dry tert-butyl benzene (50 mL) and the mixture was degassed for 10 min. A tert-butyllithium solution [54-19-4] (2.8 equiv.) was added at 0° C. to the 2.sup.nd flask and this reaction mixture was allowed to warm up at room temperature and stirred for 30 min. After slowly adding the reaction mixture of the second flask to the reaction mixture of the first flask at 0° C., the yellow mixture was stirred at room temperature overnight. After evaporating the solvent, the crude mixture was purified by column chromatography (eluent: cyclohexane/dichloromethane) to obtain the corresponding product P2 as a solid.

Cyclic Voltammetry

[0576] 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

[0577] 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

Sample Pretreatment: Spin-Coating

[0578] Apparatus: Spin150, SPS euro.

[0579] The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

[0580] Program: 1) 3 s at 400 U/min; 2) 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.

Photoluminescence Spectroscopy and Time-Correlated Single-Photon Counting (TCSPC)

[0581] 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.

[0582] Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

[0583] Excitation sources:

[0584] NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

[0585] NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

[0586] SpectraLED 310 (wavelength: 314 nm)

[0587] SpectraLED 355 (wavelength: 355 nm).

[0588] 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

[0589] 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.

[0590] Emission maxima are given in nm, quantum yields ϕ in % and CIE coordinates as x,y values.

[0591] PLOY is determined using the following protocol:

[0592] Quality assurance: Anthracene in ethanol (known concentration) is used as reference

[0593] Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength

[0594] Measurement

[0595] Quantum yields are measured for sample of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

[00001]${\Phi }_{\mathrm{PL}}=\frac{n_{\mathrm{photon}},\mathrm{emited}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{\int \frac{\lambda }{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(\lambda \right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{sample}}\left(\lambda \right)\right]d\lambda }{\int \frac{\lambda }{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(\lambda \right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{reference}}\left(\lambda \right)\right]d\lambda }$

[0596] wherein n.sub.photon denotes the photon count and Int. denotes the intensity.

HPLC-MS

[0597] HPLC-MS analysis is performed on an HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL).

[0598] A typical HPLC method is as follows: a reverse phase column 4.6 mm×150 mm, particle size 3.5 μm from Agilent (ZORBAX Eclipse Plus 95 Å C18, 4.6×150 mm, 3.5 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[%] 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

[0599] using the following solvent mixtures:

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

[0600] An injection volume of 5 μL from a solution with a concentration of 0.5 mg/mL of the analyte is taken for the measurements.

[0601] Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source either in positive (APCI+) or negative (APCI−) ionization mode.

Production and Characterization of Optoelectronic Devices

[0602] Optoelectronic devices, such as OLED devices, including organic molecules according to the disclosure 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%.

[0603] 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.

[0604] 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:

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

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

[0605] The values correspond to the average of several pixels (typically two to eight), and the standard deviation between these pixels is given.

EXAMPLES

Example 1

[0606] ##STR00074##

[0607] Example 1 was synthesized according to AAV1 (yield 91%) and AAV2 (yield 31%) with E1=(2-(9H-carbazol-9-yl)phenyl)boronic acid [1189047-28-6] and E2=1,3,6,8-tetramethyl-9H-carbazole [6558-85-6].

[0608] FIG. 1 depicts the emission spectrum of example 1 (10% by weight in PMMA). The emission maximum (Amax) is at 535 nm. The photoluminescence quantum yield (PLQY) is 56%, the full width at half maximum (FWHM) is 0.36 eV and the emission lifetime is 1.33 μs. The resulting CIEx coordinate is 0.38 and the CIEy coordinate is 0.58.

[0609] .sup.1H NMR (300 MHz, methylene chloride-d.sub.2) δ 8.78 (d, J=8.8 Hz, 1H), 8.59 (d, J=8.6 Hz, 1H), 8.51 (dd, J=7.4, 1.2 Hz, 1H), 8.33 (ddd, J=7.7, 1.5, 0.6 Hz, 1H), 7.95 (ddd, J=8.8, 7.1, 1.8 Hz, 1H), 7.89-7.82 (m, 3H), 7.79 (dd, J=7.6, 1.8 Hz, 1H), 7.72 (ddd, J=8.6, 7.3, 1.4 Hz, 1H), 7.57-7.49 (m, 2H), 7.26 (ddd, J=7.8, 7.1, 0.8 Hz, 1H), 6.88 (s, 2H), 2.50 (s, 6H), 1.81 (s, 6H).

Example D1

[0610] Example 1 was tested in the OLED D1, which was fabricated with the following layer structure;

TABLE-US-00003 Layer # Thickness D1 10 100 nm Al 9  2 nm Liq 8 20 nm nBPhen 7 10 nm MAT1 6 50 nm MAT2 (80%): Example 1 (20%) 5 10 nm MAT2 4 10 nm TCTA 3 50 nm NPB 2  5 nm HAT-CN 1 50 nm ITO Substrate Glass [00075][00076]

[0611] OLED D1 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 16.7%. The emission maximum is at 542 nm with a FWHM of 75 nm at 5.2 V. The corresponding CIEx value is 0.387 and the corresponding CIEy value is 0.588.

[0612] Additional Examples of Organic Molecules of the Disclosure

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