LIGHT-EMITTING TRIAZINE DERIVATIVES FOR OPTOELECTRONIC DEVICES

Abstract

SUMMARY

The invention relates to a light emitting organic molecule, in particular for the application in optoelectronic devices. According to the invention, the organic molecule has one 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 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; and exactly one substituent selected from the group consisting of R.sup.11, R.sup.12, R.sup.13, R.sup.14, and R.sup.15 is cyanophenyl.

Claims

1. An organic molecule, comprising: a first chemical moiety comprising a structure of Formula I, ##STR00407## and two second chemical moieties, each independently comprising a structure of Formula II, ##STR00408## wherein the first chemical moiety is linked to each of the second chemical moieties via a single bond; wherein T is a binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, or is R.sup.I; V is a binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, or is R.sup.I; W is a binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, or is selected from the group consisting of R.sup.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 a binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, or is R.sup.I; V′ is a binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, or is R.sup.I; W′ is a binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, or is selected from the group consisting of R.sup.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; R.sup.11, R.sup.12, R.sup.13, R.sup.14 and R.sup.15 are each selected from the group consisting of R.sup.I and R.sup.A; Z is at each occurrence independently from one another 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; # represents the binding site of the first chemical moiety to the second chemical moiety; R.sup.A comprises at each occurrence, independently from each other of a structure of Formula BN-I, ##STR00409## which is bonded to the structure of Formula I via the position marked by the dashed line and wherein exactly one R.sup.BN group is CN while the remainder 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.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.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5; 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.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.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, any of R.sup.a, R.sup.3, R.sup.4 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; 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 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 R.sup.A, 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; and exactly one substituent selected from the group consisting of R.sup.11, R.sup.12, R.sup.13, R.sup.14, and R.sup.15 is R.sup.A.

2. The organic molecule according to claim 1, wherein T and T′ are each a binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties, and W and W′ are each R.sup.A.

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

4. The organic molecule according to claim 1, wherein the second chemical moiety comprises a structure of Formula IIa: ##STR00410##

5. The organic molecule according to claim 1, wherein the second chemical moiety comprises a structure of Formula IIb: ##STR00411## 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.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5.

6. The organic molecule according to claim 1, wherein the second chemical moiety comprises a structure of Formula IIc: ##STR00412## 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.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5C═CR.sup.5, C═C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5.

7. The organic molecule according to claim 1, 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.

8. A method for preparing the organic molecule according to claim 1, the method comprising reacting a substituted 2,4-dichloro-6-(chlorophenyl)triazine.

9. An optoelectronic device comprising the organic molecule according to claim 1 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.

10. The optoelectronic device according to claim 9, 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.

11. A composition, comprising: (a) the organic molecule according to claim 1, 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.

12. The composition according to claim 11, 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 organic molecule; and (iv) optionally, 0-94% by weight of at least one further host compound D with a structure differing from the organic molecule; and (v) optionally 0-94% by weight of a solvent.

13. An optoelectronic device comprising the composition according to claim 11, 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.

14. The optoelectronic device according to claim 9, 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.

15. A method for producing an optoelectronic device, the method comprising depositing the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.

16. The optoelectronic device according to claim 13, 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.

17. A method for producing an optoelectronic device, the method comprising depositing the composition according to claim 11 by a vacuum evaporation method or from a solution.

Description

EXAMPLES

General Synthesis Scheme

[0370] The general synthesis scheme provides a synthesis scheme for organic molecules according to the invention.

##STR00028##

General Procedure for Synthesis AAV0-1

[0371] ##STR00029##

[0372] Under nitrogen atmosphere, dry THF was added to (3-chloro-iodobenzene (1.00 equivalents, CAS 625-99-0), cooled down to −20° C. followed by nitrogen-sparging for 10 min. Isopropylmagnesium chloride-lithium chloride complex solution in THF (1.3 M, 1.10 equivalents, CAS 745038-86-2) was added dropwise to the solution and the mixture was stirred at −20° C. for 1 h (solution A). In a separate flask under nitrogen atmosphere, dry THF was added to cyanuric chloride (1.50 equivalents, CAS 108-77-0), cooled down to −20° C. followed by nitrogen-sparging for 10 min (Solution B). Solution A was then transferred via cannula into solution B and the mixture was heated to 60° C. for 2 h. Subsequently, the reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic phases were dried by magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by recrystallization. The product was obtained as a solid.

General Procedure for Synthesis AAV0-2

[0373] ##STR00030##

[0374] Under nitrogen atmosphere, dry THF was added to (4-chloro-iodobenzene (1.00 equivalents, CAS 625-99-0), cooled down to −20° C. followed by nitrogen-sparging for 10 min. Isopropylmagnesium chloride-lithium chloride complex solution in THF (1.3 M, 1.10 equivalents, CAS 745038-86-2) was added dropwise to the solution and the mixture was stirred at −20° C. for 1 h (solution A). In a separate flask under nitrogen atmosphere, dry THF was added to cyanuric chloride (1.50 equivalents, CAS 108-77-0), cooled down to −20° C. followed by nitrogen-sparging for 10 min (Solution B). Solution A was then transferred via cannula into solution B and the mixture was heated to 60° C. for 2 h. Subsequently, the reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic phases were dried by magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by recrystallization. The product was obtained as a solid.

General Procedure for Synthesis AAV1-1

[0375] ##STR00031##

[0376] Under nitrogen atmosphere, a mixture of dioxane and water (ratio of 9:1) was added to (4-chloro-2-fluorophenyl)boronic acid (2.20 equivalents, CAS 160591-91-3), 2,4-dichloro-6-(3-chlorophenyl)-1,3,5-triazine (1.00 equivalents, product of AAV0-1), potassium carbonate (3.40 equivalents), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.04 equivalents, CAS 72287-26-4), followed by nitrogen-sparging for 10 min. The reaction mixture was stirred under reflux (heating plate set to 110° C.) for 1 h. Subsequently, the reaction mixture was poured into ice water, the precipitate was filtered and washed with water as well as ethanol. The crude product was purified by recrystallization. The product was obtained as a solid.

General Procedure for Synthesis AAV1-2

[0377] ##STR00032##

[0378] Under nitrogen atmosphere, a mixture of THF and water (ratio of 10:1) was added to (4-chloro-2-fluorophenyl)boronic acid (2.10 equivalents, CAS 160591-91-3), 2,4-dichloro-6-(4-chlorophenyl)-1,3,5-triazine (1.00 equivalents, product of AAV0-2), potassium carbonate (3.40 equivalents), and tetrakis(triphenylphosphine)palladium(0) (0.04 equivalents, CAS 14221-01-3), followed by nitrogen-sparging for 10 min. The reaction mixture was stirred at 60° C. for 3 h. Subsequently, the reaction mixture was poured into ice-cold water, the precipitate was filtered and washed with water as well as ethanol. The crude product was heated in ethanol under reflux for 1 h, hot-filtered and washed with ethanol. The product was obtained as a solid.

General Procedure for Synthesis AAV2-1

[0379] ##STR00033##

[0380] Under nitrogen atmosphere, 2,4-bis(4-chloro-2-fluorophenyl)-6-(3-chlorophenyl)-1,3,5-triazine (1.00 equivalents, product of AAV1-1), the corresponding donor molecule D-H (2.20 equivalents), and tribasic potassium phosphate (3.00 equivalents) were suspended in dry DMSO and stirred at 80° C. for 20 h. Subsequently, the reaction mixture was poured into a stirred mixture of water and ice, followed by the addition of ethyl acetate. The precipitate was filtered off and washed with water and ethyl acetate. The product was obtained as a solid.

General Procedure for Synthesis AAV2-2

[0381] ##STR00034##

[0382] The reaction conditions were analogous to AAV2-1, but 2,4-bis(4-chloro-2-fluorophenyl)-6-(4-chlorophenyl)-1,3,5-triazine (product of AAV1-2) was used as the reactant.

General Procedure for Synthesis AAV3-1

[0383] ##STR00035##

[0384] Under nitrogen atmosphere, a mixture of dioxane and water (ratio of 9:1 was added to the product of AAV2-1 (1.00 equivalents), (3-cyanophenyl)boronic acid (4.5 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 tribasic potassium phosphate (4.00 equivalents), followed by nitrogen-sparging for 5 min. The reaction mixture was stirred under reflux for 2 days, then cooled to room temperature, and poured into ice-cold water. The precipitate was filtered off and washed with water as well as isopropyl alcohol. The crude product was heated under reflux in acetonitrile for 2 h, hot-filtered, and washed with acetonitrile. Filtration through a short pad of silica using dichloromethane as solvent yields the product as a solid.

General Procedure for Synthesis AAV3-2

[0385] ##STR00036##

[0386] The reaction conditions were analogous to AAV3-1, but the product of AAV2-2 was used as the reactant.

[0387] 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).

[0388] Exemplarily a halogen-substituted carbazole, particularly 3-bromocarbazole, can be used as D-H.

[0389] 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.a—Cl and R.sup.a—Br.

[0390] 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.a—B(OH).sub.2] or a corresponding boronic acid ester.

[0391] HPLC-MS:

[0392] HPLC-MS analysis was performed on an HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL).

[0393] Exemplary a typical HPLC method was as follows: a reverse phase column 4.6 mm×150 mm, particle size 3.5 μm from Agilent (ZORBAX Eclipse Plus 95 Å C18, 4.6×150 mm, 3.5 μm HPLC column) 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

[0394] 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%)

[0395] An injection volume of 5 μL from a solution with a concentration of 0.5 mg/mL of the analyte was taken for the measurements.

[0396] Ionization of the probe was performed using an APCI (atmospheric pressure chemical ionization) source either in positive (APCI+) or negative (APCI−) ionization mode.

Cyclic Voltammetry

[0397] 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).

Density Functional Theory Calculation

[0398] 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.

Photophysical Measurements

[0399] Sample pretreatment: Spin-coating

[0400] Apparatus: Spin150, SPS euro.

[0401] The sample concentration was 10 mg/ml, dissolved in a suitable solvent.

[0402] 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.

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

[0403] 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.

[0404] Excited state lifetimes were determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

[0405] Excitation Sources: [0406] NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns) [0407] NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns) [0408] SpectraLED 310 (wavelength: 314 nm) [0409] SpectraLED 355 (wavelength: 355 nm).

[0410] Data analysis (exponential fit) was done using the software suite DataStation and DAS6 analysis software. The fit was specified using the chi-squared-test.

Photoluminescence Quantum Yield Measurements

[0411] For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using the software U6039-05 version 3.6.0.

[0412] Emission maxima were given in nm, quantum yields CD in % and CIE coordinates as x,y values.

[0413] PLQY was determined using the following protocol:

[0414] Quality assurance: Anthracene in ethanol (known concentration) was used as reference

[0415] Excitation wavelength: the absorption maximum of the organic molecule was determined and the molecule was excited using this wavelength

[0416] Measurement

[0417] Quantum yields were measured for sample of solutions or films under nitrogen atmosphere. The yield was calculated using the equation:

[00001]${\Phi }_{\mathrm{PL}}=\frac{n_{\mathrm{photon}},\mathrm{emited}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{\int \frac{\lambda }{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(\lambda \right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{sample}}\left(\lambda \right)\right]d\lambda }{\int \frac{\lambda }{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(\lambda \right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{reference}}\left(\lambda \right)\right]d\lambda }$ [0418] wherein n.sub.photon denotes the photon count and Int. denotes the intensity.

Production and Characterization of Optoelectronic Devices

[0419] 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%.

[0420] 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 corresponds to the time point, at which the measured luminance decreased to 95% of the initial luminance etc.

[0421] 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]$\mathrm{LT}80\left(500\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}80\left(L_0\right){\left(\frac{L_0}{500\frac{{\mathrm{cd}}^2}{m^2}}\right)}^{1.6}$ [0422] wherein L.sub.0 denotes the initial luminance at the applied current density.

[0423] 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

[0424] ##STR00037##

[0425] Example 1 was synthesized according to AAV0-1 (yield 58%), AAV1-1 (yield 55%), AAV2-1 (yield 53%), and AA V3-1 (yield 75%).

[0426] MS (HPLC-MS), m/z (retention time): 1247.90 6.13 min).

[0427] FIG. 1 depicts the emission spectrum of example 1 (10% by weight in PMMA). The emission maximum (λ.sub.max) was at 517 nm. The photoluminescence quantum yield (PLQY) was 73%, the full width at half maximum (FWHM) was 0.40 eV, and the emission lifetime was 9.0 μs. The resulting CIE.sub.X coordinate was determined at 0.30 and the CIE.sub.y coordinate at 0.56.

Example 2

[0428] ##STR00038##

[0429] Example 2 was synthesized according to AAV0-2 (yield 67%), AAV1-2 (yield 47%), AAV2-2 (yield 25%), and AA V3-2 (yield 74%).

[0430] MS (HPLC-MS), m/z (retention time): 1248.1 (6.23 min).

[0431] FIG. 2 depicts the emission spectrum of example 2 (10% by weight in PMMA). The emission maximum (λ.sub.max) was at 515 nm. The photoluminescence quantum yield (PLQY) was 60%, the full width at half maximum (FWHM) was 0.40 eV, and the emission lifetime was 13.5 μs. The resulting CIE.sub.x coordinate was determined at 0.30 and the CIE.sub.y coordinate at 0.56.

Example D1

[0432] Example 1 was tested in an optoelectronic device in the form of 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 (85%): Example 1 (15%) 5 10 nm MAT2 4 10 nm TCTA 3 50 nm NPB 2 5 nm HAT-CN 1 50 nm ITO Substrate Glass [00039][00040]

[0433] OLED D1 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 18.4%. The emission maximum was at 514 nm with a FWHM of 76 nm at 6.4 V. The corresponding CIEx value was 0.27 and the CIEy value was 0.59. A LT95-value at 1200 cd/m.sup.2 of 142 h was determined.

Additional Examples of Organic Molecules of the Invention

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FIGURES

[0435] FIG. 1 Emission spectrum of example 1 (10% by weight) in PMMA.

[0436] FIG. 2 Emission spectrum of example 2 (10% by weight) in PMMA.