ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The invention relates to a light emitting organic molecule, in particular for the application in optoelectronic devices. According to the invention, the organic molecule consists of a first chemical moiety with a structure of Formula I.

##STR00001##

and two second chemical moieties with a structure of Formula II,

##STR00002##

wherein
#represents the binding site of a single bond linking the first chemical moiety to the second chemical moiety;
exactly one substituent selected from the group consisting of W, X, and Y is cyanophenyl;
exactly one substituent selected from the group consisting of T, V and W represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties;
exactly one substituent selected from the group consisting of W, X, and Y is CN or CF.sub.3; and
exactly one substituent selected from the group consisting of T, V and W represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties.

Claims

1.-15. (canceled)

16. An organic molecule, comprising a first chemical moiety comprising or consisting of a structure of Formula I, ##STR00191## and two second chemical moieties, each independently comprising or consisting of a structure of Formula II, ##STR00192## wherein each of the second chemical moieties is linked to the first chemical moiety via a single bond; wherein T is a binding site of the single bond linking the first chemical moiety to one of the two second chemical moieties, or is R.sup.I; V is the binding site of the single bond linking the first chemical moiety to one of the two second chemical moieties, or is R.sup.I; W is the binding site of the single bond linking the first chemical moiety to one of the two second chemical moieties, or is selected from the group consisting of R.sup.I and R.sup.A; X is selected from the group consisting of R.sup.I and R.sup.A; Y is selected from the group consisting of R.sup.I and R.sup.A; T is the binding site of the single bond linking the first chemical moiety to one of the two second chemical moieties, or is R.sup.II; V is the binding site of the single bond linking the first chemical moiety to one of the two second chemical moieties, or is R.sup.II; W is the binding site of the single bond linking the first chemical moiety to one of the two second chemical moieties, or is selected from the group consisting of R.sup.II, CN, and CF.sub.3; X is selected from the group consisting of R.sup.II, CN, and CF.sub.3; Y is selected from the group consisting of R.sup.II, CN, and CF.sub.3; Z is at each occurrence independently from one another selected from the group consisting of a direct bond, CR.sup.3R.sup.4, CCR.sup.3R.sup.4, CO, CNR.sup.3, NR.sup.3, O, SiR.sup.3R.sup.4, S, S(O) and S(O).sub.2; #represents the binding site of the first chemical moiety to the second chemical moiety; R.sup.A comprises or consists of a structure of Formula BN-I, ##STR00193## which is bonded to the structure of Formula I via a position marked by the dashed line and wherein exactly one R.sup.BN group is CN while the other two R.sup.BN groups are each hydrogen; R.sup.I is at each occurrence independently from one another selected from the group consisting of: hydrogen; deuterium; C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C.sub.6-C.sub.18-aryl; R.sup.II is at each occurrence independently from one another selected from the group consisting of: hydrogen; deuterium; C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C.sub.6-C.sub.18-aryl; R.sup.11, R.sup.12, R.sup.13, R.sup.14 and R.sup.15 are at each occurrence independently selected from the group consisting of: hydrogen; deuterium; CN; CF.sub.3; phenyl; C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C.sub.2-C.sub.8-alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C.sub.6-C.sub.18-aryl; R.sup.a, 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; Si(R.sup.5).sub.3; B(OR.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.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5; R.sup.5 is at each occurrence independently from 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; OSO.sub.2R.sup.6; CF.sub.3; CN; F; Br; I; C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.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.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.6 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6CCR.sup.6, CC, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, CO, CS, CSe, CNR.sup.6, P(O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; 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 from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkynyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; N(C.sub.6-C.sub.18-aryl).sub.2; N(C.sub.3-C.sub.17-heteroaryl).sub.2; and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); wherein, optionally, R.sup.a, R.sup.3, R.sup.4 and/or R.sup.5 independently form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more other substituents R.sup.a, R.sup.3, R.sup.4 and/or R.sup.5; and wherein exactly one substituent selected from the group consisting of W, X, and Y is R.sup.A, and exactly one substituent selected from the group consisting of T, V, and W represents the binding site of the single bond linking the first chemical moiety and one of the two second chemical moieties; exactly one substituent selected from the group consisting of W, X, and Y is CN or CF.sub.3, and exactly one substituent selected from the group consisting of T, V, and W represents the binding site of the single bond linking the first chemical moiety and one of the two second chemical moieties.

17. The organic molecule according to claim 16, wherein T and T are each a binding site of the single bond linking the first chemical moiety to one of the two second chemical moieties, and either X is R.sup.A and X is CN or CF.sub.3; or W is R.sup.A and X is CN or CF.sub.3.

18. The organic molecule according to claim 16, wherein R.sup.I, R.sup.II, R.sup.11, R.sup.12, R.sup.13, R.sup.14, and R.sup.15 are at each occurrence independently selected from the group consisting of hydrogen, methyl, iso-propyl, tert-butyl, mesityl, xylyl, tolyl, and phenyl.

19. The organic molecule according to claim 16, wherein the second chemical moiety comprises or consists of a structure of Formula IIa: ##STR00194##

20. The organic molecule according to claim 16, wherein the second chemical moiety comprises or consists of a structure of Formula IIb: ##STR00195## wherein R.sup.b is at each occurrence independently from one another selected from the group consisting of: hydrogen; deuterium; N(R.sup.5).sub.2; OR.sup.5; Si(R.sup.5).sub.3; B(OR.sup.5).sub.2; 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.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5.

21. The organic molecule according to claim 16, wherein the second chemical moiety comprises or consists of a structure of Formula IIc: ##STR00196## wherein R.sup.b is at each occurrence independently selected from the group consisting of: hydrogen; deuterium; N(R.sup.5).sub.2; OR.sup.5; Si(R.sup.5).sub.3; B(OR.sup.5).sub.2; 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.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5CCR.sup.5, CC, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, CO, CS, CSe, CNR.sup.5, P(O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5.

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

23. A method for preparing the organic molecule according to claim 16, the method comprising providing a substituted 2,4-dichloro-6-phenyltriazine as a reactant.

24. An optoelectronic device comprising the organic molecule according to claim 16, as a luminescent emitter and/or a host material and/or an electron transport material and/or a hole transport material and/or a hole injection material and/or a hole blocking material.

25. The optoelectronic device according to claim 24, wherein the optoelectronic device is at least one selected from the group consisting of: organic light-emitting diodes (OLEDS), light-emitting electrochemical cells, OLED-sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

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

27. The composition according to claim 26, comprising: (i) 1-50% by weight of the organic molecule; (ii) 5-98% by weight of one host compound H; (iii) 1-30% by weight of at least one further emitter molecule with a structure differing from the structure of the organic molecule; and (iv) optionally, 0-94% by weight of at least one further host compound D with a structure differing from the structure of the organic molecule; and (v) optionally, 0-94% by weight of a solvent.

28. An optoelectronic device comprising a layer formed from the composition according to claim 26, wherein the device is at least one selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED-sensors, organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

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

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

32. A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 26 by a vacuum evaporation method or from a solution.

Description

EXAMPLES

General Synthesis Scheme I

[0403] The general synthesis scheme I provides a synthesis scheme for organic molecules according to the invention.

##STR00025##

General Synthesis Scheme II

[0404] The general synthesis scheme II provides an alternative synthesis scheme for organic molecules according to the invention.

##STR00026##

[0405] General Procedure for Synthesis AAV1-1

##STR00027##

[0406] Under nitrogen atmosphere, a mixture of THF and water (ratio of 4:1) was added to 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.00 equivalents, CAS 863868-29-5), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.50 equivalents, CAS 1700-02-3), potassium carbonate (2.00 equivalents), and tetrakis(triphenylphosphine)palladium(0) (0.03 equivalents, CAS 14221-01-3), followed by nitrogen-sparging for 15 min. The reaction mixture was stirred at 60 C. until full conversion of the boronic pinacol ester was reached as judged by GC and TLC. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and brine. The organic extracts were concentrated under reduced pressure. The resulting crude product was heated to reflux in ethanol for 20 min, followed by hot filtration and washing of the solid with ethanol. Purification by MPLC using cyclohexane and dichloromethane (ratio of 1:1) yields the product as a solid.

General Procedure for Synthesis AAV2-1

[0407] ##STR00028##

[0408] Under nitrogen atmosphere, a mixture of dioxane and water (ratio of 10:1; previously degassed by nitrogen-sparging for 15 min) was added to (5-chloro-2-fluorophenyl)boronic acid (1.00 equivalents, CAS 352535-83-2), 3-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-4-fluorobenzonitrile (1.10 equivalents, product of AAV1-1), potassium acetate (3.00 equivalents), and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.03 equivalents, CAS 72287-26-4). The reaction mixture was stirred under reflux (heating plate set to 110 C.) for 4 h. After cooling to room temperature, water was added, followed by extraction with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The resulting crude product was heated to reflux in ethanol for 3 h and, upon hot filtration, washed with ethanol. The product was obtained as a solid.

General Procedure for Synthesis AAV2-2

[0409] ##STR00029##

[0410] The reaction conditions were analogous to AAV2-1, but (4-chloro-2-fluorophenyl)boronic acid (1.00 equivalents, CAS 160591-91-3) was used as a reactant. After completion of the reaction (heated for 4 h) and cooling down to ambient temperature, the reaction mixture was poured into water. The resulting precipitate was filtered off and washed with water and cold ethanol. The crude product was heated to reflux in a mixture of toluene and cyclohexane (ratio of 3:1) for 1 h. Upon hot filtration, the product was washed with cold ethanol. It was obtained as a solid.

General Procedure for Synthesis AAV3-1

[0411] ##STR00030##

[0412] 3-(4-(5-chloro-2-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-4-fluorobenzonitrile (1.00 equivalents, product of AAV2-1), the corresponding donor molecule D-H (2.20 equivalents), and tribasic potassium phosphate (3.00 equivalents) were suspended under nitrogen atmosphere in dry DMSO and stirred at 80 C. for 72 h. Subsequently, the reaction mixture was poured into a stirred mixture of water and ice. The resulting precipitate was filtered off and washed with water and n-hexane. The crude product was purified by MPLC using cyclohexane and dichloromethane (ratio of 1:1) and subsequently heated to reflux in ethanol for 2 h. Upon hot filtration, the product was washed with ethanol. It was obtained as a solid.

General Procedure for Synthesis AAV3-2

[0413] ##STR00031##

[0414] The reaction conditions were analogous to AAV3-1, but 3-(4-(4-chloro-2-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-4-fluorobenzonitrile (1.00 equivalents, product of AAV2-2) was used as a reactant. The filtration through the AlO.sub.x column was performed using toluene. The resulting crude product was heated to reflux in acetonitrile for 2 h. Upon hot filtration, the product was washed with acetonitrile. Recrystallization from a mixture of toluene and acetonitrile (ratio of 3:2) affords the product as a solid.

General Procedure for Synthesis AAV4-1

[0415] ##STR00032##

[0416] Under nitrogen atmosphere, a mixture of dioxane and water (ratio of 20:3) was added to the product of AAV3-1 (1.00 equivalents), (2-cyanophenyl)boronic acid (1.25 equivalents, CAS 150255-96-2), tris(dibenzylideneacetone)dipalladium(0) (0.04 equivalents, CAS 51364-51-3), 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (X-Phos, 0.16 equivalents, CAS 564483-18-7), and potassium carbonate (2.50 equivalents), followed by nitrogen-sparging for 10 min. The reaction mixture was stirred under reflux for 2 h (reaction monitored by TLC), then cooled to ambient temperature, and poured into ice-cold water. The precipitate was filtered and washed with water. The crude product was recrystallized from n-hexane and ethyl acetate, followed by purification via MPLC using cyclohexane and dichloromethane in a ratio of 1:1. The product was obtained as a solid.

General Procedure for Synthesis AAV4-2

[0417] ##STR00033##

[0418] The reaction conditions were analogous to AAV4-1, but the product of AAV3-2 was used as a reactant.

General Procedure for Synthesis AAV5-1

[0419] ##STR00034##

[0420] Under nitrogen atmosphere, dry toluene was added to 3-chloro-4-fluoro-[1,1-biphenyl]-3-carbonitrile (1.00 equivalents) and 4,4,4,4,5,5,5,5-octamethyl-2,2-bi(1,3,2-dioxaborolane) (1.30 equivalents, CAS 73183-34-3), followed by nitrogen-sparging for 15 min. The reaction mixture was stirred at 110 C. for 3 h (reaction monitored by TLC), then cooled to 70 C. Celite and charcoal were added and the suspension was stirred at 70 C. for 20 min, filtered and the filtrate was extracted with ethyl acetate and brine. The combined organic layers were concentrated under reduced pressure and the crude product was recrystallized from n-hexane. The product was obtained as a solid.

General Procedure for Synthesis AAV6-1

[0421] ##STR00035##

[0422] Under nitrogen atmosphere, a mixture of THF and water (ratio of 4:1) was added to 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1-biphenyl]-3-carbonitrile (1.00 equivalents, product of AAV5-1), 2,4-dichloro-6-phenyl-1,3,5-triazine (1.50 equivalents, CAS 1700-02-3), potassium carbonate (2.00 equivalents), and tetrakis(triphenylphosphine)palladium(0) (0.03 equivalents, CAS 14221-01-3), followed by nitrogen-sparging for 10 min. The reaction mixture was stirred at 60 C. for 16 h. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and brine. The organic extracts were concentrated under reduced pressure. Purification by MPLC using cyclohexane and dichloromethane (ration of 1:1) yields the product as a solid.

General Procedure for Synthesis AAV7-1

[0423] ##STR00036##

[0424] Under nitrogen atmosphere, a mixture of THF and water (ratio of 25:3) was added to 3-(4-chloro-1-phenyl-1,3,5-triazin-2-yl)-4-fluoro-[1,1-biphenyl]-3-carbonitrile (1.00 equivalents, product of AAV6-1), 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.20 equivalents, CAS 863868-29-5), potassium carbonate (2.00 equivalents), and tetrakis(triphenylphosphine)palladium(0) (0.03 equivalents, CAS 14221-01-3), followed by nitrogen-sparging for 15 min. The reaction mixture was stirred at 60 C. for 16 h. After cooling to room temperature, a mixture of water and THF (ratio of 1:1) was added. The precipitate was filtered off and dissolved in dichloromethane. After washing with water, dichloromethane was removed under reduced pressure yielding the product as a solid.

General Procedure for Synthesis AAV8-1

[0425] ##STR00037##

[0426] 3-(4-(5-cyano-2-fluorophenyl)-6-phenyl-1,3,5-triazin-2-yl)-4-fluoro-[1,1-biphenyl]-3-carbonitrile (1.00 equivalents, product of AAV7-1), the corresponding donor molecule D-H (2.20 equivalents), and tribasic potassium phosphate (3.00 equivalents) were suspended under nitrogen atmosphere in dry DMSO and stirred at 90 C. for 11 h. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and water, followed by extraction of the organic layer with water. Dichloromethane was removed under reduced pressure affording the crude product. Filtration through a short pad of silica using dichloromethane was followed by concentration of the filtrate in vacuo. Acetonitrile was added and, upon treatment in an ultrasonic bath for 15 min and storing at 18 C., the formed precipitate was filtered off and washed with acetonitrile. The product was obtained as a solid.

[0427] In particular, the donor molecule D-H was a 3,6-substituted carbazole (e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g., 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1,8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g., 1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a 2-substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole, 2-tert-butylcarbazole), or a 3-substituted carbazole (e.g., 3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

[0428] Exemplarily a halogen-substituted carbazole, particularly 3-bromocarbazole, can be used as D-H.

[0429] In a subsequent reaction a boronic acid ester functional group or boronic acid functional group may be exemplarily introduced at the position of the one or more halogen substituents, which was introduced via D-H, to yield the corresponding carbazol-3-ylboronic acid ester or carbazol-3-ylboronic acid, e.g., via the reaction with bis(pinacolato)diboron (CAS No. 73183-34-3). Subsequently, one or more substituents R.sup.a may be introduced in place of the boronic acid ester group or the boronic acid group via a coupling reaction with the corresponding halogenated reactant R.sup.a-Hal, preferably R.sup.aCl and R.sup.aBr.

[0430] Alternatively, one or more substituents R.sup.a may be introduced at the position of the one or more halogen substituents, which was introduced via D-H, via the reaction with a boronic acid of the substituent R.sup.a [R.sup.aB(OH).sub.2] or a corresponding boronic acid ester.

[0431] HPLC-MS:

[0432] HPLC-MS analysis was performed on an HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL).

[0433] Exemplary a typical HPLC method was as follows: a reverse phase column 4.6 mm150 mm, particle size 3.5 m from Agilent (ZORBAX Eclipse Plus 95 C18, 4.6150 mm, 3.5 m HPLC column) was used in the HPLC. The HPLC-MS measurements were 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 [0434] and 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%)

[0435] An injection volume of 5 L from a solution with a concentration of 0.5 mg/mL of the analyte was taken for the measurements.

[0436] Ionization of the probe was performed using an APCI (atmospheric pressure chemical ionization) source either in positive (APCI+) or negative (APCI) ionization mode.

[0437] Cyclic Voltammetry

[0438] Cyclic voltammograms were 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 were 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).

[0439] Density Functional Theory Calculation

[0440] Molecular structures were optimized employing the BP86 functional and the resolution of identity approach (RI). Excitation energies were calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies were calculated with the B3LYP functional. Def2-SVP basis sets (and an m4-grid for numerical integration were used. The Turbomole program package was used for all calculations.

[0441] Photophysical Measurements

[0442] Sample pretreatment: Spin-coating

[0443] Apparatus: Spin150, SPS euro.

[0444] The sample concentration was 10 mg/ml, dissolved in a suitable solvent.

[0445] 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 were tried at 70 C. for 1 min.

[0446] Photoluminescence spectroscopy and TCSPC (Time-correlated single-photon counting)

[0447] Steady-state emission spectroscopy was 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 were corrected using standard correction fits.

[0448] Excited state lifetimes were determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

[0449] Excitation sources:

[0450] NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

[0451] NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

[0452] SpectraLED 310 (wavelength: 314 nm)

[0453] SpectraLED 355 (wavelength: 355 nm).

[0454] Data analysis (exponential fit) was done using the software suite DataStation and DAS6 analysis software. The fit was specified using the chi-squared-test.

[0455] Photoluminescence Quantum Yield Measurements

[0456] For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) was used.

[0457] Quantum yields and CIE coordinates were determined using the software U6039-05 version 3.6.0.

[0458] Emission maxima were given in nm, quantum yields in % and CIE coordinates as x,y values.

[0459] PLQY was determined using the following protocol:

[0460] Quality assurance: Anthracene in ethanol (known concentration) was used as reference

[0461] Excitation wavelength: the absorption maximum of the organic molecule was determined and the molecule was excited using this wavelength

[0462] Measurement

[0463] Quantum yields were measured for sample of solutions or films under nitrogen atmosphere. The yield was calculated using the equation:

[00001]${}_{\mathrm{PL}}=\frac{n_{\mathrm{photon}},\mathrm{emited}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{\frac{}{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(\right)-{\mathrm{Int}}_{\mathrm{absored}}^{\mathrm{sample}}\left(\right)\right]d}{\frac{}{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(\right)-{\mathrm{Int}}_{\mathrm{absored}}^{\mathrm{reference}}\left(\right)\right]d}$ [0464] wherein n.sub.photon denotes the photon count and Int. denotes the intensity.

Production and Characterization of Optoelectronic Devices

[0465] Optoelectronic devices, such as OLED devices, including an organic molecule 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 was given in %. The total weight-percentage values amount to 100%, thus if a value was not given, the fraction of this compound equals to the difference between the given values and 100%.

[0466] The not fully optimized OLEDs were 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 was extracted from the change of the luminance during operation at constant current density. The LT50 value corresponds to the time, where the measured luminance decreased to 50% of the initial luminance, analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80% of the initial luminance, and LT 95 to the time point, at which the measured luminance decreased to 95% of the initial luminance etc.

[0467] Accelerated lifetime measurements were performed (e.g. applying increased current densities). For example, LT80 values at 500 cd/m.sup.2 were determined using the following equation:

[00002]$\mathrm{LT}80\left(500\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}80\left(L_0\right){\left(\frac{L_0}{500\frac{{\mathrm{cd}}^2}{m^2}}\right)}^{1.6}$ [0468] wherein L.sub.0 denotes the initial luminance at the applied current density. The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels was given. The figures show the data series for one OLED pixel.

Example 1

[0469] ##STR00038##

[0470] Example 1 was synthesized according to AAV1-1 (yield 45%), AAV2-1 (yield 74%), AAV3-1 (yield 29%), and AAV4-1 (yield 29%).

[0471] MS (HPLC-MS), m/z (retention time): 1070.0 (5.79 min).

[0472] FIG. 1 depicts the emission spectrum of example 1 (10% by weight in PMMA). The emission maximum (.sub.max) was at 508 nm. The photoluminescence quantum yield (PLQY) was 70%, the full width at half maximum (FWHM) was 0.41 eV, and the emission lifetime was 8.9 s. The resulting CIEx coordinate was determined at 0.28 and the CIEy coordinate at 0.53.

Example 2

[0473] ##STR00039##

[0474] Example 2 was synthesized according to AAV1-1 (yield 41%), AAV2-2 (yield 63%), AAV3-2 (yield 63%), and AAV4-2 (yield 44%).

[0475] MS (HPLC-MS), m/z (retention time): 1070.6 (5.80 min).

[0476] FIG. 2 depicts the emission spectrum of example 2 (10% by weight in PMMA). The emission maximum (.sub.max) was at 515 nm. The photoluminescence quantum yield (PLQY) was 66%, the full width at half maximum (FWHM) was 0.41 eV, and the emission lifetime was 9.2 s. The resulting CIE.sub.x coordinate was determined at 0.31 and the CIE.sub.y coordinate at 0.56.

Example 3

[0477] ##STR00040##

[0478] Example 3 was synthesized according to AAV5-1 (yield 86%), AAV6-1 (yield 51%), AAV7-1 (yield 79%), and AAV8-1 (yield 10%).

[0479] MS (HPLC-MS), m/z (retention time): 1070.8 (5.92 min).

[0480] FIG. 3 depicts the emission spectrum of example 3 (10% by weight in PMMA). The emission maximum (.sub.max) was at 509 nm. The photoluminescence quantum yield (PLQY) was 71%, the full width at half maximum (FWHM) was 0.41 eV, and the emission lifetime was 10.2 s. The resulting CIE.sub.x coordinate was determined at 0.28 and the CIE.sub.y coordinate at 0.53.

Example 4

[0481] ##STR00041##

[0482] Example 4 was synthesized according to AAV1-1(yield 52%), AAV2-1(yield 74%), AAV3-1 (yield 59%), and AAV4-1 (yield 65%) replacing 2-cyanophenylboronic acid by 4-cyanophenylboronic acid (CAS 126747-14-6).

[0483] MS (HPLC-MS), m/z (retention time): 1072.1 (5.92 min).

[0484] FIG. 4 depicts the emission spectrum of example 4 (10% by weight in PMMA). The emission maximum (.sub.max) was at 509 nm. The photoluminescence quantum yield (PLQY) was 74%, the full width at half maximum (FWHM) was 0.41 eV, and the emission lifetime was 15.2 s. The resulting CIEx coordinate was determined at 0.28 and the CIEy coordinate at 0.53.

Example D1

[0485] Example 1 was tested in an optoelectronic device in the form of an 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 [00042][00043]

[0486] OLED D1 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 18.4%. The emission maximum was at 512 nm with a FWHM of 76 nm at 7.0 V. The corresponding CIEx value was 0.28 and the CIEy value was 0.59. A LT95-value at 1200 cd/m.sup.2 of 220 h was determined.

Example D2

[0487] Example 3 was tested in the OLED D2, which was fabricated with the following layer structure:

TABLE-US-00004 Layer # Thickness D2 10 100 nm Al 9 2 nm Liq 8 20 nm NBPhen 7 10 nm MAT1 6 50 nm MAT2 (85%):Example 3 (15%) 5 10 nm MAT2 4 10 nm TCTA 3 50 nm NPB 2 5 nm HAT-CN 1 50 nm ITO Substrate Glass

[0488] OLED D2 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 16.7%. The emission maximum was at 508 nm with a FWHM of 76 nm at 7.0 V. The corresponding CIEx value was 0.26 and the CIEy value was 0.58.

Example D3

[0489] Example 3 was tested in the OLED D3, which was fabricated with the following layer structure:

TABLE-US-00005 Layer # Thickness D3 10 100 nm Al 9 2 nm Liq 8 20 nm NBPhen 7 10 nm MAT1 6 50 nm MAT2 (84%): Example 3 (15%): MAT3 (1%) 5 10 nm MAT2 4 10 nm TCTA 3 50 nm NPB 2 5 nm HAT-CN 1 50 nm ITO Substrate Glass [00044]

[0490] OLED D3 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 18.3%. The emission maximum was at 532 nm with a FWHM of 36 nm at 5.5 V. The corresponding CIEx value was 0.31 and the CIEy value was 0.65.

Example D4

[0491] Example 4 was tested in the OLED D4, which was fabricated with the following layer structure:

TABLE-US-00006 Layer # Thickness D4 10 100 nm Al 9 2 nm Liq 8 20 nm NBPhen 7 10 nm MAT1 6 50 nm MAT2 (80%):Example 4 (20%) 5 10 nm MAT2 4 10 nm TCTA 3 50 nm NPB 2 5 nm HAT-CN 1 50 nm ITO Substrate Glass

[0492] OLED D4 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 19.3%. The emission maximum was at 514 nm with a FWHM of 78 nm at 6.4 V. The corresponding CIEx value was 0.28 and the CIEy value was 0.59. A LT95-value at 1200 cd/m.sup.2 of 245 h was determined.

Additional Examples of Organic Molecules of the Invention

[0493] ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068##

##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096##

##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146##

##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176##

##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190##

FIGURES

[0494] FIG. 1 Emission spectrum of example 1 (10% by weight) in PMMA.

[0495] FIG. 2 Emission spectrum of example 2 (10% by weight) in PMMA.

[0496] FIG. 3 Emission spectrum of example 3 (10% by weight) in PMMA.

[0497] FIG. 4 Emission spectrum of example 4 (10% by weight) in PMMA.