ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The invention relates to an organic molecule, in particular for the application in optoelectronic devices. According to the invention, the organic molecule is represented by a plurality of units, wherein each unit includes or consists of a structure represented by Formula I

##STR00001##

wherein

n=0 or 1; and

X is at each occurrence independently selected from the group consisting of a direct bond, CR.sup.3R.sup.4, C═CR.sup.3R.sup.4, C═O, C═NR.sup.3, NR.sup.3, O, SiR.sup.3R.sup.4, S, S(O) and S(O).sub.2.

Claims

1-15. (canceled)

16. An organic molecule, comprising a structure represented by Formula I: ##STR00434## and wherein n=0 or 1; X is at each occurrence independently selected from the group consisting of a direct bond, CR.sup.3R.sup.4, C═CR.sup.3R.sup.4, C═O, C═NR.sup.3, NR.sup.3, O, SiR.sup.3R.sup.4, S, S(O) and S(O).sub.2; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.I, R.sup.II, R.sup.III, R.sup.IV and R.sup.V 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, B(R.sup.5).sub.2, OSO.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.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.2-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5; R.sup.d and R.sup.e are independently selected from the group consisting of: hydrogen, deuterium, CF.sub.3, CN, F, Br, I; which is optionally substituted with one or more substituents R.sup.a 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.a; and C.sub.2-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.a; R.sup.a is 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, B(R.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, F, Br, I; 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.2-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 one 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, B(R.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.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.2-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.6 is at each occurrence independently from one 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 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 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 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 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 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.2-C.sub.1 7-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.2-C.sub.17-heteroaryl).sub.2; and N(C.sub.2-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); wherein optionally, one or more of the substituents R.sup.a, R.sup.d, R.sup.e, and R.sup.5, each independently form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R.sup.a, R.sup.d, R.sup.e, and R.sup.5; and wherein optionally, one or more of the substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, and R.sup.V, each independently form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, and R.sup.V.

17. The organic molecule according to claim 16, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, and R.sup.V are each independently from one another 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, B(R.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, halogen; C.sub.1-C.sub.18-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.18-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.18-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.18-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.18-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.18-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.2-C.sub.17-heteroaryl, which is optionally substituted with one or more substituents R.sup.5 wherein optionally, one or more of the substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, and R.sup.V, each independently form a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, and R.sup.V.

18. The organic molecule according to claim 16, comprising a structure of Formula III: ##STR00435## and wherein in Formula III, R.sup.1, R.sup.2, R.sup.a, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V, and X are the same as respectively defined in connection with Formula I.

19. The organic molecule according to claim 16, wherein X is selected from the group consisting of: a direct bond, NR.sup.3 and O.

20. The organic molecule according to claim 16, comprising a structure of Formula III-2: ##STR00436## and wherein R.sup.3 is a C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.5, and wherein R.sup.1, R.sup.2, R.sup.a, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, and R.sup.V are the same as respectively defined in connection with Formula I.

21. The organic molecule according to claim 16, wherein R.sup.V is selected from the group consisting of: N(R.sup.5).sub.2; OR.sup.5; C.sub.1-C.sub.18-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.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.2-C.sub.17-heteroaryl, wherein the substituent R.sup.V optionally forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R.sup.2 and R.sup.IV, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents, deuterium, halogen, CN or CF.sub.3.

22. The organic molecule according to claim 16, wherein, when X is NR.sup.3 and R.sup.d and R.sup.e are connected to each other to form an aromatic ring system, R.sup.V is N(R.sup.5).sub.2 and/or forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R.sup.2, R.sup.3, R.sup.5, and R.sup.IV.

23. The organic molecule according to claim 16, wherein R.sup.a is 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, B(R.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, halogen; C.sub.1-C.sub.18-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.18-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.18-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.18-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.18-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; which is optionally substituted with one or more substituents R.sup.5; and C.sub.2-C.sub.17-heteroaryl, which is optionally substituted with one or more substituents R.sup.5.

24. The organic molecule according to claim 16, wherein at least one substituent selected from the group consisting of R.sup.1, R.sup.2, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, and R.sup.V forms a mono- or polycyclic, aliphatic, aromatic, heteroaromatic and/or benzo-fused ring system with one or more adjacent substituents selected from among R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.I, R.sup.II, R.sup.III, R.sup.IV, and R.sup.V.

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

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

27. 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.

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

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

30. 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.

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

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

33. A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 27 by a vacuum evaporation method or from a solution.

Description

EXAMPLES

[1468] ##STR00146## ##STR00147##

##STR00148## ##STR00149##

General Procedure for Synthesis:

[1469] AAV1: I0 (1.00 equivalents), 3,5-dichloro-iodobenzene (I0-1, 0.8 equivalents), palladium(II) acetate (0.03 equivalents), 2-dicyclohexylphosphino-2′, dimethoxybiphenyl (S-Phos, CAS: 657408-07-6, 0.06 equivalents) and tribasic potassium phosphate (K.sub.3PO.sub.4; 3.00 equivalents) were stirred under nitrogen atmosphere in a dioxane/water mixture at 90° C. for 12 h. After cooling down to room temperature (rt), the reaction mixture was extracted between DCM and brine and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography and I-1 was obtained with a yield of 84% GC-MS: 313.02 m/z.

[1470] AAV2: I-1 (1.00 equivalents), diphenylamine (CAS: 122-39-4, 2.5 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), tri-tert-butyl phosphine (CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (CAS: 865-48-5, 4.00 equivalents) were stirred under nitrogen atmosphere in dry toluene at 100° C. for 12 h. After cooling down to room temperature (rt) the reaction mixture was washed with water and brine and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by recrystallization and I-2 was obtained with a yield of 45%. LC-MS: 578.40 m/z at rt: 4.69 min.

[1471] AAV3: I-2 (1.00 equivalents) was placed in a round bottom flask under nitrogen. The solvent 1,2-dichlorobenzene was added. Boron tribromide (CAS: 10294-33-4, 6.00 equivalents) was added dropwise and it was heated to 180° C. After cooling to rt, it was further cooled to 0° C. DIPEA (CAS: 7087-68-5, 10.00 equivalents) was added and it was stirred for 1 h. The reaction mixture was washed with water and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography and P was obtained with a yield of 32%. LC-MS: 586 m/z at rt: 5.73 min.

##STR00150## ##STR00151## ##STR00152##

General Procedure for Synthesis:

[1472] AAV4: E1 (1.00 equivalents), bis(pinacolato)diboron (CAS: 73183-34-3, 1.0 equivalents), tris(dibenzylideneacetone)dipalladium (CAS: 51364-51-3, 0.02 equivalents), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (X-Phos, CAS: 564483-18-7, 0.08 equivalents) and potassium acetate (KOAc; CAS: 127-08-2, 2.00 equivalents) were stirred under nitrogen atmosphere in dry toluene at 105° C. for 24 h. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-4 was obtained as a solid.

[1473] AAV5: I-4 (1.00 equivalents), E2 (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 001 equivalents), S-Phos (CAS: 657408-07-6, 0.04 equivalents) and potassium phosphate tribasic (K.sub.3PO.sub.4, CAS: 7778-53-2, 3.00 equivalents) were stirred under nitrogen atmosphere in a dioxane/water mixture at 100° C. for 2 h. After cooling down to room temperature (rt) the reaction mixture was washed with water and brine. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude material was purified by recrystallization or column chromatography and I-5 was obtained as a solid.

[1474] AAV6: I-5 (1.00 equivalents) was placed in a round bottom flask under nitrogen. The solvent 1,2-dichlorobenzene was added. Boron tribromide (CAS: 10294-33-4, 4.00 equivalents) was added dropwise and it was heated to 180° C. overnight. After cooling to rt, it was further cooled to 0° C. DIPEA (CAS: 7087-68-5, 10.00 equivalents) was added and it was stirred for 1 h. The reaction mixture was washed with water and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography or by recrystallization and P-1 was obtained as a solid.

##STR00153## ##STR00154## ##STR00155##

General Procedure for Synthesis:

[1475] AAV7: E3 (2.00 equivalents), E4 (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, CAS: 657408-07-6, 0.04 equivalents) and tribasic potassium phosphate (K.sub.3PO.sub.4; 3.00 equivalents) were stirred under nitrogen atmosphere in a THF/water mixture at 80° C. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-6 was obtained as solid.

[1476] AAV8: I-6 (1.00 equivalents), E5 (1.00 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 001 equivalents), tri-tert-butyl phosphine (CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (CAS: 865-48-5, 3.00 equivalents) were stirred under nitrogen atmosphere in dry toluene at 110° C. for 72 h. After cooling down to room temperature (rt) the reaction mixture was washed with water and brine and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by recrystallization or column chromatography and I-7 was obtained as a solid,

[1477] AAV9: I-7 (1.00 equivalents) was placed in a round bottom flask under nitrogen. The solvent 1,2-dichlorobenzene was added. Boron tribromide (CAS: 10294-33-4, 4.00 equivalents) was added dropwise and it was heated to 180° C. After cooling to rt, it was further cooled to 0° C. DIPEA (CAS: 7087-68-5, 10.00 equivalents) was added and it was stirred for 1 h. The reaction mixture was washed with water and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography or by recrystallization and P-2 was obtained as a solid.

##STR00156## ##STR00157##

General Procedure for Synthesis:

[1478] AAV10: E5 (1.05 equivalents), E6 (1.00 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.005 equivalents), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 1.50 equivalents) and tri-tert-butylphosphonium tetrafluoroborate (P(tBu).sub.3HBF.sub.4; CAS: 131274-22-1, 0.02 equivalents) were stirred under nitrogen atmosphere in dry toluene at 100° C. overnight. After cooling down to room temperature (rt) the reaction mixture was added water, the phases were separated and the combined organic layers dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-8 was obtained as solid.

[1479] AAV11: I-8 (1.00 equivalents), E3 (1.2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), X-Phos (CAS: 564483-18-7, 0.04 equivalents) and potassium phosphate tribasic (K.sub.3PO.sub.4, CAS: 7778-53-2, 2.00 equivalents) were stirred under nitrogen atmosphere in a THF/water mixture at 80° C. for 96 h. After cooling down to room temperature (rt) the reaction mixture was washed with water and brine, the combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude material was purified by recrystallization or column chromatography and I-7 was obtained as a solid.

[1480] The last reaction step was performed as described in AAV9, where 1,2-dichlorobenzene was used as the solvent and where the reaction temperature was 180° C.

##STR00158## ##STR00159## ##STR00160##

General Procedure for Synthesis:

[1481] The first reaction step is performed as described in AAV7.

[1482] AAV12: I-6 (2.00 equivalents), E7 (1.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), tri-tert-butyl phosphine (CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (CAS: 865-48-5, 6.00 equivalents) were stirred under nitrogen atmosphere in dry toluene at 110° C. for 72 h. After cooling down to room temperature (rt) the reaction mixture extracted between ethyl acetate and brine and the phases were separated and the solvent was removed under reduced pressure. The crude material was purified by recrystallization or by column chromatography and I-9 was obtained as a solid.

[1483] AAV13: I-9 (1.00 equivalents) was placed in a round bottom flask under nitrogen. The solvent 1,2-dichlorobenzene was added. Boron tribromide (CAS: 10294-33-4, 6.00 equivalents) was added dropwise and it was heated to 180° C. After cooling to rt, it was further cooled to 0° C. DIPEA (CAS: 7087-68-5, 10.00 equivalents) was added and it was stirred for 1 h. The reaction mixture was washed with water and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography or recrystallization and P-3 was obtained as a solid.

##STR00161## ##STR00162## ##STR00163##

General procedure for synthesis:

[1484] AAV14: E5 (2.10 equivalents), E8 (1.00 equivalents), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.15 equivalents) and tri-tert-butylphosphine (P(tBu).sub.3; CAS: 13716-12-6, 0.04 equivalents) were stirred under nitrogen atmosphere in dry toluene at 110° C. for 1 h. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and 1-10 was obtained as solid.

[1485] AAV15: I-10 (1.00 equivalents), E3 (1.2 equivalents), palladium(II) acetate (CAS: 3375-31-3, 0.06 equivalents), X-Phos (CAS: 564483-18-7, 0.12 equivalents) and potassium phosphate tribasic (K.sub.3PO.sub.4, CAS: 7778-53-2, 3.00 equivalents) were stirred under nitrogen atmosphere in a dioxane/water mixture at 100° C. for 55 h. After cooling down to room temperature (rt) the reaction mixture was extracted between toluene and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by recrystallization or column chromatography and I-11 was obtained as a solid.

[1486] AAV0-3:

[1487] Under nitrogen, I-11 (1.00 equivalents) was dissolved in tert-butylbenzene. At 20° C., n-BuLi (2.5 M in hexane, CAS: 10972-8, 1.1 equivalents) was injected and the mixture stirred for 15 min. Subsequently, t-BuLi (1 M in pentane, CAS: 594-19-4, 2.2 equivalents) was added and the mixture stirred at 60° C. for 2 h. Subsequently, the mixture was cooled down below −60° C., followed by dropwise addition of BBr.sub.3 CAS: 10294-33-4, 1.3 equivalents). The mixture was allowed to warm to rt, followed by stirring at rt for 16 h. The mixture was extracted between ethyl acetate and water and the combined organic layers were concentrated under reduced pressure. The crude was purified with column chromatography or by recrystallization to obtain the target compound P-4 as a solid.

##STR00164## ##STR00165## ##STR00166##

General Procedure for Synthesis:

[1488] AAV16: E3 (1.00 equivalents), E9 (1.1 equivalents), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, CAS: 14221-01-3, 0.02 equivalents) and potassium carbonate (K.sub.2CO.sub.3; 2.00 equivalents) were stirred under nitrogen atmosphere in a THF/water mixture at 80° C. for 48 h. After cooling down to room temperature (rt) the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-12 was obtained as solid.

[1489] AAV17: I-12 (1.00 equivalents), di-tert-butyl dicarbonate (CAS: 24424-99-5, 1.4 equivalents), 4-dimethylaminopyridin (4-DHAP, CAS: 1122-58-3, 1.00 equivalents) were stirred under nitrogen atmosphere in dry MeCN at room temperature for 16 h. The reaction mixture was added NaOH solution (1 M), the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-13 was obtained as solid.

[1490] AAV18: I-13 (1.00 equivalents), E5 (1.20 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), tri-tert-butylphosphonium tetrafluoroborate (CAS: 131274-22-1, 0.04 equivalents) and sodium tert-butoxide (CAS: 865-48-5, 2.00 equivalents) were stirred under nitrogen atmosphere in dry toluene at 110° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture was washed with water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude material was purified by recrystallization or column chromatography and I-14 was obtained as a solid.

[1491] AAV19: I-14 (1.00 equivalents) was solved in dichloromethane (DCM). Trifluoroacetic Acid (CAS: 76-05-1; 99.7 equivalents) was added at room temperature and the reaction mixture was stirred for 2 h. Subsequently, the phases were separated and the TFA layer was extracted with DCM. The combined organic layers were washed with a saturated NaHCO.sub.3 solution and water, dried over MgSO.sub.4 and filtered. After removal of the solvent under reduced pressure, the crude material was purified by recrystallization or column chromatography and I-15 was obtained as a solid.

[1492] AAV20: I-15 (1.00 equivalents) was placed in a round bottom flask under nitrogen. The solvent o-xylene was added. At 0° C., n-butyllithium (2.5 M in hexane, CAS: 109-72-8, 1.10 equivalents) was added dropwise and the mixture stirred for 15 min. Subsequently, Cert-butyllithium (1.6 M in hexane, CAS: 594-19-4, 2.20 equivalents) was added dropwise, the temperature was increased to 60° C. and the reaction mixture was stirred for 2 h. The reaction mixture was cooled down to room temperature. At 0° C., boron tribromide (1 M in heptane, CAS: 10294-33-4, 1.30 equivalents) was added dropwise, the mixture stirred at 0° C. for 1 h, followed by stirring at rt for 6 h. The reaction mixture was poured in 5% NH.sub.3 solution, the phases were separated and the organic layer was washed with water. The organic layer was dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and P-5 was obtained as a solid.

##STR00167## ##STR00168##

General Procedure for Synthesis:

[1493] AAV21: In dry DMSO E10 (1.10 equivalents), E11 (1.00 equivalents) and tribasic potassium phosphate (1.50 equivalents, CAS: 7778-53-2) are heated at 100° C. for 48 h. After cooling down to rt, the mixture was poured onto ice water. The precipitate was filtered off, washed with water and ethanol and collected. The crude was purified by recrystallization or column chromatography to yield compound I-16 as a solid.

[1494] AAV22: Under nitrogen, in a mixture of toluene/water (8:1 by vol.), I-16 (1.00 equivalents) was reacted with E3 (1.00 equivalents), tribasic potassium phosphate (1.80 equivalents, CAS: 7778-53-2), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalents, CAS: 51364-51-3) and X-Phos (0.04 equivalents CAS: 564483-18-7) at 95° C. for 48 h. After cooling down to rt, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography or recrystallization to yield compound I-17 as a solid

[1495] AAV23: Under nitrogen, in a mixture of dioxane/water (5:1 by vol.), I-17 (1.00 equivalents) was reacted with E12 (1.50 equivalents), tribasic potassium phosphate (3.00 equivalents, CAS: 7778-53-2), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalents, CAS: 51364-51-3) and X-Phos (0.04 equivalents, CAS: 564483-18-7) at 100° C. for 5 h. After cooling down to rt, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography or recrystallization to yield compound I-18 as a solid.

[1496] The last reaction step was performed as described in AAV20.

##STR00169##

General Procedure for Synthesis:

[1497] AAV24: In dry DMSO, E13 (1.10 equivalents), E11 (1.00 equivalents) and tribasic potassium phosphate (1.50 equivalents, CAS: 7778-53-2) were heated at 100° C. for 48 h. After cooling down to rt, the mixture was poured onto ice water. The precipitate was filtered off, washed with water and ethanol and collected, The crude was purified by recrystallization or column chromatography to yield compound 1-19 as a solid.

[1498] AAV25: Under nitrogen, in a mixture of toluene/water (8:1 by vol.), I-19 (1.00 equivalents) was reacted with E3 (1.20 equivalents), tribasic potassium phosphate (2.00 equivalents, CAS: 7778-53-2), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalents, CAS: 51364-51-3) and X-Phos (0.04 equivalents, CAS: 564483-18-7) at 100° C. for 5 h. After cooling down to rt, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography or recrystallization to yield compound I-20 as a solid

[1499] The last reaction step was performed as described in AAV0-3.

##STR00170## ##STR00171##

General Procedure for Synthesis:

[1500] AAV26: Under nitrogen, in a mixture of dioxane/water (10:1 by vol.), E14 (1.00 equivalents) was reacted with E3 (1.00 equivalents), potassium carbonate (2.00 equivalents, CAS: 584-08-7), tris(dibenzylideneacetone)dipalladium(0) (0.02 equivalents, CAS: 51364-51-3) and S-Phos (0.08 equivalents, CAS: 657408-07-6) at 90° C. for 72 h. After cooling down to rt, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography or recrystallization to yield compound I-21 as a solid.

[1501] AAV27: E5 (1.00 equivalents), I-21 (1.00 equivalents), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.00 equivalents) and tri-tert-butylphosphine (P(tBu).sub.3; CAS: 13716-12-6, 0.04 equivalents) were stirred under nitrogen atmosphere in dry toluene at 110° C. for 24 h. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-22 was obtained as solid,

[1502] AAV28: Under nitrogen in dry dichlorobenzene, I-22 (1.00 equivalents) was reacted with BBr.sub.3 (3.00 equivalents, CAS: 10294-33-4) at 135° C. for 45 min. After cooling down to rt, the mixture was further cooled down to 0° C., followed by the addition of DIPEA (10.0 equivalents, CAS: 7087-68-5). Water was added, the phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, dried over MgSO.sub.4, filtered and concentrated. The crude was purified by column chromatography or recrystallization to yield compound P-8 as a solid,

##STR00172## ##STR00173##

General Procedure for Synthesis:

[1503] AAV29: E5 (1.05 equivalents), E14 (1.00 equivalents), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.005 equivalents), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 1.50 equivalents) and tri-tert-butylphosphonium tetrafluoroborate (HP(tBu).sub.3BF.sub.4; CAS: 131274-22-1, 0.02 equivalents) were stirred under nitrogen atmosphere in dry toluene at 100° C. for 1 h. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-23 was obtained as solid.

[1504] AAV30: Under nitrogen, in a mixture of dioxane/water (5:1 by vol.), I-23 (1.00 equivalents) was reacted with E3 (1.10 equivalents), tribasic potassium phosphate (2.00 equivalents, CAS: 7778-53-2), tris(dibenzylideneacetone)dipalladium(0) (0.01 equivalents, CAS: 51364-51-3) and S-Phos (0.04 equivalents, CAS: 657408-07-6) at 100° C. for 48 h. After cooling down to rt, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography or recrystallization to yield compound I-24 as a solid

[1505] AAV31: Under nitrogen in dry dichlorobenzene, I-24 (1.00 equivalents) was reacted with BBr.sub.3 (3.00 equivalents, CAS: 10294-33-4) at 90° C. for 1 h. After cooling down to rt, the mixture was further cooled down to 0° C., followed by the addition of DIPEA (10.0 equivalents, CAS: 7087-68-5). Water was added, the phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, dried over MgSO.sub.4, filtered and concentrated. The crude was purified by column chromatography or recrystallization to yield compound P-9 as a solid.

##STR00174##

General Procedure for Synthesis:

[1506] AAV32: Under nitrogen, in a mixture of dioxane/water (4:1 by vol.), E3 (1.00 equivalents) was reacted with E9 (1.30 equivalents), potassium carbonate (2.00 equivalents, CAS: 584-08-7) and tetrakis(triphenylphosphine)palladium(0) (0.03 equivalents, CAS: 14221-01-3) at 80° C. for 8 h. After cooling down to rt, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography or recrystallization to yield compound I-12 as a solid.

[1507] AAV33: E5 (1.10 equivalents), I-12 (1.00 equivalents), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.20 equivalents) and tri-tert-butylphosphonium tetrafluoroborate (HP(tBu).sub.3BF4; CAS: 131274-22-1, 0.04 equivalents) were stirred under nitrogen atmosphere in dry toluene at 110° C. for 3 h. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-15 was obtained as solid.

[1508] AAV34: Under nitrogen, a solution of I-15 (1.00 equivalents) in dry o-xylene was added n-BuLi (2.5 M in hexane, 1.10 equivalents, CAS: 109-72-8) at rt. After 15 min of stirring, t-BuLi (1.6 M in pentane, 2.20 equivalents, CAS: 594-19-4) was added and the mixture heated at 60° C. for 2 h. Subsequently, the mixture was cooled below −78° C., followed by dropwise addition of BBr.sub.3 (1.50 equivalents, CAS: 10294-33-4). Subsequently, the mixture was stirred at 0° C. for 1 h, followed by stirring at rt for 16 h. The mixture was poured onto a saturated solution of NaHCO.sub.3. The phases were separated and the aqueous layers were extracted with ethyl acetate. The combined organic layers were washed with water, dried over MgSO.sub.4, filtered and concentrated. The crude was purified by column chromatography or recrystallization to obtain compound P5 as a solid.

##STR00175##

General Procedure for Synthesis:

[1509] AAV35: E15 (1.10 equivalents), E16 (1.00 equivalents), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), sodium tent-butoxide (NaOtBu, CAS: 865-48-5, 2.00 equivalents) and tri-tert-butylphosphine (P(tBu).sub.3; CAS: 13716-12-6, 0.04 equivalents) were stirred under nitrogen atmosphere in dry toluene at 60° C. until completion of the reaction (TLC control). After coaling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and E-5 was obtained as solid.

[1510] AAV36: E5 (1.00 equivalents), I-21 (1.00 equivalents), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), sodium Cert-butoxide (NaOtBu, CAS: 865-48-5, 2.00 equivalents) and tri-tert-butylphosphonium tetrafluoroborate (HP(t-Bu).sub.3BF.sub.4; CAS: 131274-22-1, 0.02 equivalents) were stirred under nitrogen atmosphere in dry toluene under reflux until completion of the reaction (TLC control). After cooling down to room temperature (rt) the reaction mixture was extracted between toluene and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-22 was obtained as solid.

[1511] AAV37: I-22 (1.00 equivalents) was placed in a round bottom flask under nitrogen. The solvent 1,2-dichlorobenzene was added. Boron tribromide (CAS: 10294-33-4, 3.00 equivalents) was added dropwise and it was heated to 180° C. until completion of the reaction (TLC control). After cooling to rt, it was further cooled to 0° C. DIPEA (CAS: 7087-68-5, 10.00 equivalents) was added and it was stirred for 1 h. The reaction mixture was washed with water and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography or by recrystallization and P-8 was obtained as a solid.

##STR00176## ##STR00177##

General Procedure for Synthesis:

[1512] AAV38: E17 (1.40 equivalents), E18 (0.9 equivalents), hydroiodic acid (CAS: 10034-85-2, 0.20 equivalents) were stirred under nitrogen atmosphere in dry acetonitrile at 100° C. for 16 h. The reaction mixture was cooled down to 0° C.; the precipitate was filtered and washed with cold acetonitrile. The solid was dissolved in acetonitrile; iodine (CAS: 7553-56-2, 0.40 equivalents) was added and the mixture was stirred at 100° C. until reaction completion (monitored by TLC). The reaction mixture was quenched with a saturated sodium thiosulfite solution and the precipitate was washed with cold acetonitrile, methanol and hexane. The crude material was purified by recrystallization or by column chromatography and I-25 was obtained as a solid.

[1513] AAV39: I-25 (1.00 equivalents), E19 (6.0 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.04 equivalents), tri-tert-butylphosphonium tetrafluoroborate (CAS: 131274-22-1, 0.16 equivalents) and sodium tert-butoxide (CAS: 865-48-5, 7.00 equivalents) were stirred under nitrogen atmosphere in dry toluene at 110° C. for 72 h. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the phases were separated and the solvent was removed under reduced pressure. The crude material was purified by recrystallization or by column chromatography and I-26 was obtained as a solid.

[1514] AAV40: I-26 (1.00 equivalents) was placed in a round bottom flask under nitrogen. The solvent 1,2-dichlorobenzene was added. Boron tribromide (CAS: 10294-33-4, 4.00 equivalents) was added dropwise and it was heated to 180° C. until reaction completion (TLC control). After cooling to rt, it was further cooled to 0° C. DIPEA (CAS: 7087-68-5, 10.00 equivalents) was added and it was stirred for 1 h. The reaction mixture was washed with water and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography or recrystallization and P-10 was obtained as a solid.

##STR00178## ##STR00179## ##STR00180##

General Procedure for Synthesis:

[1515] AAV41: E17 (2.00 equivalents), E20 (1.0 equivalents), and bis(trifluoromethyl)methanol (CAS: 920-66-1, 300 ml) were stirred under nitrogen atmosphere at room temperature until reaction completion (TLC control). The reaction mixture was cooled down to 0° C.; the precipitate was filtered and washed with cold acetonitrile. The solid was re-dissolved in acetonitrile; 1,4-benzoquinone (CAS: 106-51-4, 0.20 equivalents) was added and the mixture was stirred at room temperature until reaction completion (monitored by TLC). The solvent was removed under reduced pressure. The crude material was purified by recrystallization or by column chromatography and I-27 was obtained as a solid.

[1516] AAV42: I-27 (1.00 equivalents), E21 (1.00 equivalents), were stirred under nitrogen atmosphere in dichloromethane at room temperature. Iodine (CAS: 7553-56-2, 0.03 equivalents) was added and the mixture was stirred at room temperature until reaction completion (monitored by TLC). The solvent was removed under reduced pressure. The crude material was purified by recrystallization or by column chromatography and I-28 was obtained as a solid.

[1517] AAV43: I-28 (1.00 equivalents), E19 (2.5 equivalents), tris(dibenzylideneacetone)dipalladium(0) (CAS: 51364-51-3, 0.03 equivalents), tri-tert-butylphosphonium tetrafluoroborate (CAS: 131274-22-1, 0.12 equivalents) and sodium tert-butoxide (CAS: 865-48-5, 4.00 equivalents) were stirred under nitrogen atmosphere in dry toluene at 110° C. until reaction completion (TLC control). After cooling down to room temperature (rt) the reaction mixture extracted between ethyl acetate and brine and the phases were separated and the solvent was removed under reduced pressure. The crude material was purified by recrystallization or by column chromatography and I-29 was obtained as a solid.

[1518] AAV44: I-29 (1.00 equivalents) was placed in a round bottom flask under nitrogen. The solvent chlorobenzene was added. Boron tribromide (CAS: 10294-33-4, 4.00 equivalents) was added dropwise and it was heated to 70° C. until reaction completion (TLC control). After cooling to rt, it was further cooled to 0° C. DIPEA (CAS: 7087-68-5, 10.00 equivalents) was added and it was stirred for 1 h. The reaction mixture was washed with water and the phases were separated and then the solvent was removed under reduced pressure. The crude material was purified by column chromatography or recrystallization and P-11 was obtained as a solid.

Generation E3

[1519] ##STR00181##

General Procedure for Synthesis:

[1520] AAV45: E22 (1.00 equivalents) was solved in dry chloroform and N-bromosuccinimide (CAS: 128-08-5, 1.1 equivalents) was added in portions under nitrogen atmosphere at 0° C. The mixture was stirred at room temperature for 4 h and subsequently extracted between dichloromethane and water and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and E2 was obtained as a solid.

[1521] AAV46: E2 (1.00 equivalents), bis(pinacolato)diboron (CAS: 73183-34-3, 1.5 equivalents), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride (CAS: 72287-26-4, 0.02 equivalents) and potassium acetate (KOAc; CAS: 127-08-2, 3.00 equivalents) were stirred under nitrogen atmosphere in dry dioxane at 95° C. for 24 h. After cooling down to room temperature (rt) the reaction mixture was extracted between dichloromethane and water and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and E3 was obtained as a solid.

##STR00182## ##STR00183## ##STR00184##

General Procedure for Synthesis:

[1522] AAV47: Under nitrogen, in a mixture of dry dioxane, E14 (1.00 equivalents) was reacted with bis(pinacolato)diboron (1.50 equivalents, CAS: 73183-34-3), potassium acetate (3.00 equivalents, CAS: 127-08-2), [1,1′-bis(diphenylphosphino)ferrocene]palladium (H) dichloride (0.04 equivalents, CAS: 72287-26-4) at 100° C. for 16 h. After cooling down to rt, water was added, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography or recrystallization to yield compound I-30 as a solid.

[1523] AAV48: E2 (1.00 equivalents), I-30 (1.00 equivalents), [1,1′-bis(diphenylphosphino)ferrocene]palladium (H) dichloride (CAS: 72287-26-4 0.02 equivalents) and potassium phosphate tribasic (K.sub.3O.sub.4P; CAS: 7778-53-2, 3.00 equivalents) were stirred under nitrogen atmosphere in dioxane/water (4:1 by vol) at 80° C. for 4 h. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and water and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-21 was obtained as a solid.

[1524] The last two reaction steps were performed as described in AAV27 and AAV28.

##STR00185## ##STR00186##

For R.sup.1═H, both isomers can be made in the last reaction step:

##STR00187## ##STR00188##

General Procedure for Synthesis:

[1525] AAV49: E23 (1.00 equivalents), E24 (1.15 equivalents), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.01 equivalents), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.20 equivalents) and tri-tert-butylphosphonium tetrafluoroborate (HP(t-Bu).sub.3E3F4; CAS: 131274-22-1, 0.04 equivalents) were stirred under nitrogen atmosphere in dry toluene to 70° C. until completion of the reaction (TLC control). After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and E5a was obtained as solid.

[1526] AAV50: Under nitrogen, in a mixture of dry dioxane, E14 (1.00 equivalents) was reacted with bis(pinacolato)diboron (1.50 equivalents, CAS: 73183-34-3), potassium acetate (3.00 equivalents, CAS: 127-08-2), [1,1′-bis(diphenylphosphino)ferrocene]palladium (H) dichloride (0.04 equivalents, CAS: 72287-26-4) at 100° C. for 16 h. After cooling down to rt, water was added, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude was purified by column chromatography or recrystallization to yield compound I-30 as a solid.

[1527] AAV51: E2 (1.00 equivalents), I-30 (1.00 equivalents), [1,1′-bis(diphenylphosphino)ferrocene]palladium (H) dichloride (CAS: 72287-26-4 0.02 equivalents) and potassium phosphate tribasic (K.sub.3O.sub.4P: CAS: 7778-53-2, 3.00 equivalents) were stirred under nitrogen atmosphere in dioxane/water (4:1 by vol) at 80° C. for 4 h. After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and water and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-21 was obtained as a solid.

[1528] AAV52: E5a (1.10 equivalents), I-21 (1.00 equivalents), tris(dibenzylideneacetone)-dipalladium(0) (CAS: 51364-51-3, 0.02 equivalents), sodium tert-butoxide (NaOtBu, CAS: 865-48-5, 3.20 equivalents) and tri-tert-butylphosphonium tetrafluoroborate (HP(t-Bu).sub.3BF.sub.4; CAS: 131274-22-1, 0.08 equivalents) were stirred under nitrogen atmosphere in dry o-xylol to 120° C. until completion of the reaction (TLC control). After cooling down to room temperature (rt) the reaction mixture was extracted between ethyl acetate and brine and the combined organic layers were concentrated under reduced pressure. The crude material was purified by column chromatography or by recrystallization and I-31 was obtained as solid.

[1529] AAV53: Under nitrogen in dry chlorobenzene, I-31 (1.00 equivalents) was reacted with BBr.sub.3 (4.00 equivalents, CAS: 10294-33-4) at −10° C. for 3 h, 2 h at rt, 16 h at 50° C. and additionally at 70° C. for 2 h. After cooling down to rt, the mixture was followed by the addition of DIPEA (10.0 equivalents, CAS: 7087-68-5). Water was added, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, dried over MgSO.sub.4, filtered and concentrated. The crude was purified by column chromatography or recrystallization to yield compound P-12 (and for R.sup.1═H additionally P-13) as a solid.

Cyclic Voltammetry

[1530] 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 is corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).

Density Functional Theory Calculation

[1531] 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

[1532] Apparatus: Spin150, SPS euro.

[1533] The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

[1534] 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.

[1535] Photoluminescence Spectroscopy and Time-Correlated Single-Photon Counting (TCSPC)

[1536] 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.

[1537] Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

[1538] Excitation Sources:

[1539] NanoLED 370 (wavelength: 371 nm, puts duration: 1.1 ns)

[1540] NanoLED 290 (wavelength: 294 nm, puts duration: <1 ns)

[1541] SpectraLED 310 (wavelength: 314 nm)

[1542] SpectraLED 355 (wavelength: 355 nm).

[1543] Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.

[1544] Photoluminescence Quantum Yield Measurements

[1545] 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.

[1546] Emission maxima are given in nm, quantum yields Φ in % and CIE coordinates as x,y values.

[1547] PLQY is determined using the following protocol:

[1548] Quality assurance: Anthracene in ethanol (known concentration) is used as reference

[1549] Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength

[1550] Measurement

[1551] Quantum yields are measured, for sample, of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

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

[1552] wherein n.sub.photon denotes the photon count and Int. denotes the intensity.

Production and Characterization of Optoelectronic Devices

[1553] Optoelectronic devices, such as OLED devices including 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%.

[1554] 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.

[1555] 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]$\begin{array}{cc}\mathrm{LT}80\left(500\frac{c{d}^2}{m^2}\right)=LT80\left(L_0\right){\left(\frac{L_0}{500\frac{c{d}^2}{m^2}}\right)}^{1.6}& \end{array}$

[1556] wherein L.sub.0 denotes the initial luminance at the applied current density.

[1557] The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.

HPLC-MS:

[1558] HPLC-MS analysis is performed on an HPLC by Agent (1100 series) with MS-detector (Thermo LTQ XL).

[1559] Exemplary 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 mm×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 Time [ml/min] [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

[1560] 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%)

[1561] 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.

[1562] 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

[1563] ##STR00189##

[1564] Example 1 was synthesized according to

[1565] AAV1 (84% yield),

[1566] AAV2 (45% yield),

[1567] AAV3 (32% yield).

[1568] MS (LC-MS): 586 m/z at rt: 5.73 min.

[1569] The emission maximum of example 1 (2% by weight in PMMA) is at 428 nm, the full width at half maximum (FWHM) is 0.27 eV. The CIEx coordinate is 0.16 and the CIEy coordinate is 0.08. The photoluminescence quantum yield (PLQY) is 54%.

Example 2

[1570] ##STR00190##

[1571] Example 2 was synthesized according to general synthesis scheme VII

[1572] AAV14 (33% yield), wherein 1,5-dibromo-2,3-dichlorobenzene (CAS: 81067-42-73) and 2,2″-dinaphthylamine (CAS: 532-18-3) were used as reactant E8 and E5, respectively,

[1573] AAV15 (34% yield), wherein 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) was used as reactant E3,

[1574] AAV0-3 (3% yield).

[1575] MS (LC-MS, APCI ion source): 786.5 m/z at rt: 7.00 min.

[1576] The emission maximum of example 2 (2% by weight in PMMA) is at 434 nm, the CIEx coordinate is 0.16 and the CIEy coordinate is 0.11.

Example 3

[1577] ##STR00191##

[1578] Example 3 was synthesized according to general synthesis scheme III

[1579] AAV4 (30% yield), wherein 5-bromo-N1,N1,N3,N3-tetraphenyl-1,3-benzenediamine (CAS: 1290039-73-4) was used as reactant E1,

[1580] AAV5 (21% yield), wherein 6-bromo-5H-benzofuro[3,2-c]carbazole (CAS: 1438427-35-0) was used as reactant E2,

[1581] AAV6 (4% yield).

[1582] MS (LC-MS, APCI ion source): 676.7 m/z at rt: 6.87 min.

[1583] The emission maximum of example 3 (2% by weight in PMMA) is at 440 nm, the full width at half maximum (FWHM) is 0.21 eV. The CIEx coordinate is 0.15 and the CIEy coordinate is 0.06. The photoluminescence quantum yield (PLQY) is 56%.

Example 4

[1584] ##STR00192##

[1585] Example 4 was synthesized according to general synthesis scheme IV

[1586] AA V7 (71% yield), wherein 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) and 3,5-dichloro-N,N-diphenylaniline (CAS: 1329428-05-8) were used as reactant E3 and E4, respectively,

[1587] AAV8 (52% yield), wherein N,N,N′-triphenyl-benzene-1,3-diamine (CAS: 1554227-26-7) was used as reactant E5,

[1588] AAV9 (3% yield),

[1589] MS (LC-MS, APCI ion source): 753.9 m/z at rt: 6.62 min.

[1590] The emission maximum of example 4 (2% by weight in PMMA) is at 427 nm, the full width at half maximum (FWHM) is 0.13 eV. The CIEx coordinate is 0.16 and the CIEy coordinate is 0,05. The photoluminescence quantum yield (PLQY) is 58%.

Example 5

[1591] ##STR00193##

[1592] Example 5 was synthesized according to general synthesis scheme V

[1593] AAV10 (68% yield), wherein 2,2′-dinaphthylamine (CAS: 532-18-3) and 1-bromo-3-chlorodibenzo[b,d]furan (CAS: 2043962-13-4) were used as reactant E5 and E6, respectively,

[1594] AAV11 (90% yield), wherein 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) was used as reactant E3,

[1595] AAV9 (38% yield).

[1596] MS (LC-MS, APCI ion source): 609.5 m/z at rt: 6.26 min.

[1597] The emission maximum of example 5 (2% by weight in PMMA) is at 462 nm, the full width at half maximum (FWHM) is 0.14 eV. The CIEx coordinate is 0.14 and the CIEy coordinate is 0.22. The photoluminescence quantum yield (PLQY) is 65%.

Example 6

[1598] ##STR00194##

[1599] Example 6 was synthesized according to

[1600] AAV7 (71% yield), wherein 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) and 3,5-dichloro-N,N-diphenylaniline (CAS: 1329428-05-8) were used as reactant E3 and E4, respectively,

[1601] AAV12 (54% yield), wherein N,N′-diphenyl-m-phenylenediamine (CAS: 5905-36-2) was used as reactant E7,

[1602] AAV13 (2% yield).

[1603] MS (LC-MS, APCI ion source): 1094.1 m/z at rt: 8.18 min.

[1604] The emission maximum of example 6 (2% by weight in PMMA) is at 443 nm, the full width at half maximum (FWHM) is 0.13 eV. The CIEx coordinate is 0.15 and the CIEy coordinate is 0.07. The photoluminescence quantum yield (PLQY) is 61%.

Example 7

[1605] ##STR00195##

[1606] Example 7 was synthesized according to

[1607] AAV16 (49% yield), wherein 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) and 1,3-dibromo-2-chlorobenzene (CAS: 19230-27-4) were used as reactant E3 and E9, respectively,

[1608] AAV17 (78% yield),

[1609] AAV18 (56% yield), wherein 2,2′-dinaphthylamine (CAS: 532-18-3) was used as reactant E5,

[1610] AAV19 (69% yield),

[1611] AAV20 (5% yield),

[1612] MS (LC-MS, APCI ion source): 519.6 m/z at rt: 5.54 min.

[1613] The emission maximum of example 7 (2% by weight in PMMA) is at 480 nm, the full width at half maximum (FWHM) is 0.18 eV. The CIEx coordinate is 0.13 and the CIEy coordinate is 0.33. The photoluminescence quantum yield (PLQY) is 53%.

Example 8

[1614] ##STR00196##

[1615] Example 8 was synthesized according to

[1616] AAV21 (85% yield), wherein 1-bromo-2,5-dichloro-3-fluorobenzene (CAS: 202865-57-4) and 7H-dibenzo[c,g]carbazole (CAS: 194-59-2) were used as reactants E10 and E11, respectively:

[1617] AAV22 (62% yield), wherein 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) was used as the substrate E3;

[1618] AAV23 (78% yield), wherein 2,4,6-trimethylphenylboronic acid (CAS: 5980-97-2) represented reactant E12;

[1619] and AAV0-3 (2% yield).

[1620] MS (LC-MS, APCI ion source): m/z=635.7 at rt=7.72 min.

[1621] The emission maximum of example 8 (2% by weight in PMMA) is at 470 nm, the full width at half maximum (FWHM) is 0.24 eV. The CIEx coordinate is 0.15 and the CIEy coordinate is 0.25. The photoluminescence quantum yield (PLQY) is 48%

Example 9

[1622] ##STR00197##

[1623] Example 9 was synthesized according to

[1624] AAV24 (70% yield), wherein 1-bromo-2-chloro-3-fluorobenzene (CAS: 883499-24-9) and 7H-dibenzo[c,g]carbazole (CAS: 194-59-2) were used as the reactants E13 and E11, respectively;

[1625] AAV25 (51% yield), wherein 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) was used as reactant E3;

[1626] and AAV0-3 (2% yield).

[1627] MS (LC-MS, APCI ion source): m/z=517 at rt=6.45 min.

[1628] The emission maximum of example 9 (2% by weight in PMMA) is at 478 nm, the full width at half maximum (FWHM) is 0.26 eV. The CIEx coordinate is 0.16 and the CIEy coordinate is 0.36. The photoluminescence quantum yield (PLQY) is 37%.

Example 10

[1629] ##STR00198##

[1630] Example 10 was synthesized according to

[1631] AAV21 (85% yield), wherein 1-bromo-2,5-dichloro-3-fluorobenzene (CAS: 202865-57-4) and 7H-dibenzo[c,g]carbazole (CAS: 194-59-2) were used as reactants E10 and E11, respectively;

[1632] AAV22 (62% yield), wherein 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) was used as the substrate E3;

[1633] AAV23 (69% yield), wherein phenylboronic add (CAS: 98-80-6) represented reactant E12;

[1634] and AAV0-3 (1% yield).

[1635] MS (LC-MS, APCI ion source): m/z=593 at rt=7.25 min.

[1636] The emission maximum of example 10 (2% by weight in P A) is at 485 nm.

Example 11

[1637] ##STR00199##

[1638] Example 11 was synthesized according to

[1639] AAV26 (34% yield), wherein 1-bromo-3-chlorodibenzo[b,d]furan (CAS: 2043962-13-4) and 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) were used as the reactants E14 and E3;

[1640] AAV27 (37% yield), wherein 2,2′-dinaphthylamine (CAS: 532-18-3) was used as reactant E5;

[1641] and AAV28 (3% yield).

[1642] MS (LC-MS, APCI ion source): m/z=609.5 at rt=6.38 min.

[1643] The emission maximum of example 11 (2% by weight in PMMA) is at 456 nm, the full width at half maximum (FWHM) is 0.22 eV. The CIEx coordinate is 0.15 and the CIEy coordinate is 0.13. The photoluminescence quantum yield (PLQY) is 45%.

Example 12

[1644] ##STR00200##

[1645] MS (LC-MS, APCI ion source): m/z=1275.2 at rt=8.99 min.

[1646] The emission maximum of example 12 (2% by weight in PMMA) is at 459 nm, the full width at half maximum (FWHM) is 0.15 eV. The CIEx coordinate is 0.14 and the CIEy coordinate is 0.13. The photoluminescence quantum yield (PLQY) is 53%.

Example 13

[1647] ##STR00201##

[1648] Example 13 was synthesized according to

[1649] AAV29 (71% yield), where 4-bromo-3-chlorodibenzo[b,d]furan (CAS: 1960445-63-9) and 2,2′-dinaphthylamine (CAS: 532-18-3) were used as the reactants E14 and E5, respectively;

[1650] AAV30 (54% yield), where 1-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1219637-88-3) was used as compound E3;

[1651] and AAV31 (31% yield).

[1652] MS (LC-MS, APCI ion source): m/z=609.7 at rt=6.23 min.

[1653] The emission maximum of example 13 (2% by weight in PMMA) is at 464 nm, the full width at half maximum (FWHM) is 0.13 eV. The CIEx coordinate is 0.14 and the CIEy coordinate is 0.18. The photoluminescence quantum yield (PLQY) is 58%.

Example 14

[1654] ##STR00202##

[1655] Example 14 was synthesized according to

[1656] AAV32 (31% yield), where 3,6-bis(1,1-dimethylethyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (CAS: 1510810-80-6) and 1,3-dibromo-5-tert-butyl-2-chlorobenzene (CAS: 1000578-25-5) were used as the reactants E3 and E9, respectively;

[1657] AAV33 (48% yield), wherein N-[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4-amine (CAS: 102113-98-4) was used as compound E5;

[1658] and AAV33 (24% yield).

[1659] MS (LC-MS, APCI ionization source): m/z=740.0 at rt=7.90 min.

[1660] The emission maximum of example 14 (2% by weight in PMMA) is at 440 nm, the full width at half maximum (FWHM) is 0.22 eV. The CIEx coordinate is 0.15 and the CIEy coordinate is 0.06. The photoluminescence quantum yield (PLQY) is 74%.

Example 15

[1661] ##STR00203##

[1662] Example 15 was synthesized according to

[1663] AAV38 (25% yield), where indole (CAS: 120-72-9) and 3,5-dibromobenzaldehyde (CAS: 56990-02-4) were used as the reactants E17 and E18, respectively;

[1664] AAV39 (51% yield), where diphenylamine (CAS: 122-39-4) was used as E19;

[1665] and AAV40 (38% yield).

[1666] MS (LC-MS, APC ionization source): m/z=1094.0 at it=8.14 min.

[1667] The emission maximum of example 15 (2% by weight in PMMA) is at 515 nm, the full width at half maximum (FWHM) is 0.13 eV. The CIEx coordinate is 0.31 and the CIEy coordinate is 0.64. The photoluminescence quantum yield (PLQY) is 31%.

Example 16

[1668] ##STR00204##

[1669] Example 16 was synthesized according to

[1670] AAV38 (25% yield), where indole (CAS: 120-72-9) and 3,5-dibromobenzaldehyde (CAS: 56990-02-4) were used as the reactants E17 and E18, respectively;

[1671] AAV39 (70% yield), where 2,2′-dinaphthylamine (CAS: 532-18-3) was used as E19;

[1672] and AAV40 (47% yield).

[1673] MS (LC-MS, APCI ionization source): m/z=1494.0 at rt=8.74 min.

[1674] The emission maximum of example 16 (2% by weight in PMMA) is at 522 nm, the full width at half maximum (FWHM) is 0.09 eV. The photoluminescence quantum yield (PLQY) is 48%.

Example 17

[1675] ##STR00205##

[1676] Example 17 was synthesized according to

[1677] AAV41 (34% yield), wherein 4,7-dihydro-1H-indole (CAS: 26686-10-2) and 3,5-dibromobenzaldehyde (CAS: 56990-02-4) were used as the reactants E17 and E20;

[1678] AAV42 (15% yield), where trimethyl orthoformate (CAS: 149-73-5) was used as E21;

[1679] AAV43 (19% yield), where bis(3-biphenylyl)amine (CAS: 169224-65-1) was used as E19;

[1680] and AAV44 (27% yield).

[1681] MS (LC-MS, APCI ionization source): m/z=988.0 at rt=8.56 min.

[1682] The emission maximum of example 17 (2% by weight in PMMA) is at 444 nm, the full width at half maximum (FWHM) is 0.29 eV. The CIEx coordinate is 0.15 and the CIEy coordinate is 0.09. The photoluminescence quantum yield (PLQY) is 45%.

Example 18

[1683] ##STR00206##

[1684] Example 18 was synthesized according to

[1685] AAV45 (85% yield), wherein 3,6-di-tert-butylcarbazole (CAS: 37500-95-1) was used as the substrate E22;

[1686] AAV46 (83% yield);

[1687] AAV21 (85% yield), wherein 1-bromo-2,5-dichloro-3-fluorobenzene (CAS: 202865-57-4) and 7H-dibenzo[c,g]carbazole (CAS: 194-59-2) were used as reactants E10 and E11, respectively;

[1688] AAV22 (46% yield);

[1689] AAV23 (87% yield), wherein 2,4,6-trimethylphenylboronic acid (CAS: 5980-97-2) represented reactant E12;

[1690] and AAV0-3 (7.2% yield).

[1691] MS (LC-MS, APCI ion source): m/z=746 at rt=8.90 min.

[1692] The emission maximum of example 18 (2% by weight in PMMA) is at 471 nm, the full width at half maximum (FWHM) is 0.24 eV. The CIEx coordinate is 0.14 and the CIEy coordinate is 0.25. The photoluminescence quantum yield (PLQY) is 48%.

Example 19

[1693] ##STR00207##

[1694] Example 19 was synthesized according to

[1695] AAV47 (74% yield), wherein 4-bromo-2-chlorodibenzo[b,d]furan (CAS: 2087889-86-7) was used as the substrate E14;

[1696] AAV45 (85% yield), wherein 3,6-di-tert-butylcarbazole (CAS: 37500-95-1) was used as the substrate E22;

[1697] AAV48 (74% yield);

[1698] AAV27 (33% yield), where bis(4-tert-butylphenyl)amine (CAS: 4627-22-9) was used as compound E5;

[1699] and AAV28 (6.1% yield).

[1700] MS (LC-MS, APCI ion source): m/z=734.8 at rt=8.73 min.

[1701] The emission maximum of example 19 (2% by weight in PMMA) is at 471 nm, the full width at half maximum (FWHM) is 0.16 eV. The CIEx coordinate is 0.13 and the CIEy coordinate is 0.26. The photoluminescence quantum yield (PLQY) is 76%.

Example 20

[1702] ##STR00208##

[1703] Example 20 was synthesized according to

[1704] AAV49 (50% yield), wherein 2-bromoanthracene (CAS: 7321-27-9) and 3,5-di-tert-butylaniline (CAS: 2380-36-1) were used as the substrate E23 and E24, respectively;

[1705] AAV45 (85% yield), wherein 3,6-di-tert-butylcarbazole (CAS: 37500-95-1) was used as the substrate E22;

[1706] AAV50 (74% yield), wherein 4-bromo-2-chlorodibenzo[b,d]furan (CAS: 2087889-86-7) was used as E14;

[1707] AAV51 (74% yield);

[1708] AAV52 (49% yield);

[1709] and AAV53 (48% yield).

[1710] MS (LC-MS, APCI ion source): m/z=834.3 at rt=8.96 min.

[1711] The emission maximum of example 20 (2% by weight in PMMA) is at 486 nm, the full width at half maximum (FWHM) is 0.24 eV. The CIEx coordinate is 0.14 and the CIEy coordinate is 0.42. The photoluminescence quantum yield (PLQY) is 69%.

Example D1

[1712] Example 5 was tested in the OLED D1, which was fabricated with the following layer structure:

TABLE-US-00003 Layer # Thickness D1 9 100 nm Al 8  2 nm Liq 7  11 nm NBPhen 6  20 nm MAT1 5  20 nm MAT2 (98%):Example 5 (2%) 4  10 nm MAT3 3  50 nm MAT4 2  7 nm HAT-CN 1  50 nm ITO Substrate Glass [00209][00210][00211][00212]

[1713] OLED D1 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 8.7%. The emission maximum is at 466 nm with a FWHM of 18 nm at 3.9 V. The corresponding CIEx value is 0.13 and the CIEy value is 0.16. A LT95-value at 1200 cd/m.sup.2 of 55.2 h was determined.

Additional Examples of Organic Molecules/Oligomers of the Invention

[1714] ##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##

##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316##

##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324## ##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329## ##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357##

##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370## ##STR00371## ##STR00372## ##STR00373## ##STR00374## ##STR00375## ##STR00376## ##STR00377## ##STR00378## ##STR00379## ##STR00380## ##STR00381## ##STR00382## ##STR00383## ##STR00384## ##STR00385## ##STR00386## ##STR00387##

##STR00388## ##STR00389## ##STR00390## ##STR00391## ##STR00392## ##STR00393## ##STR00394## ##STR00395## ##STR00396## ##STR00397## ##STR00398## ##STR00399## ##STR00400## ##STR00401## ##STR00402## ##STR00403## ##STR00404## ##STR00405## ##STR00406## ##STR00407## ##STR00408## ##STR00409##

##STR00410## ##STR00411## ##STR00412## ##STR00413## ##STR00414## ##STR00415## ##STR00416## ##STR00417## ##STR00418## ##STR00419## ##STR00420## ##STR00421## ##STR00422## ##STR00423## ##STR00424## ##STR00425## ##STR00426## ##STR00427## ##STR00428## ##STR00429## ##STR00430## ##STR00431## ##STR00432## ##STR00433##