ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The invention relates to an organic compound for the use in optoelectronic devices. According to the invention, the organic molecule has one first chemical moiety with a structure of formula I,

##STR00001##

and one second chemical moiety with a structure of Formula II,

##STR00002##

wherein the first chemical moiety is linked to the second chemical moieties via a single bond;
wherein # represents the binding site of a single bond linking the second chemical moiety to the first chemical moiety; Z is at each occurrence independently from 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; T, V, W, X and Y is independently from each other selected from the group consisting of R.sup.III and R.sup.1; R.sup.T, R.sup.V, R.sup.W, R.sup.X and R.sup.Y is independently from each other selected from the group consisting of R.sup.III and R.sup.2; R.sup.C is the binding site of a single bond linking the first chemical moiety to the second chemical moiety.

Claims

1. An organic molecule, comprising: one first chemical moiety comprising a structure of Formula I: ##STR00363## and one second chemical moiety comprising a structure of Formula II: ##STR00364## wherein the first chemical moiety is linked to the second chemical moieties via a single bond; wherein # represents the binding site of a single bond linking the second chemical moiety to the first chemical moiety; Z is at each occurrence independently from another selected from the group consisting of a direct bond, CR.sup.3R.sup.4, CCR.sup.3R.sup.4, CO, CNR.sup.3, N, O, SiR.sup.3R.sup.4, S, S(O) and S(O).sub.2; T is selected from the group consisting of R.sup.III and R.sup.1; V is selected from the group consisting of R.sup.III and R.sup.1; W is selected from the group consisting of R.sup.III and R.sup.1; X is selected from the group consisting of R.sup.III and R.sup.1; Y is selected from the group consisting of R.sup.III and R.sup.1; R.sup.T is selected from the group consisting of R.sup.III and R.sup.2; R.sup.V is selected from the group consisting of R.sup.III and R.sup.2; R.sup.W is selected from the group consisting of R.sup.III and R.sup.2; R.sup.X is selected from the group consisting of R.sup.III and R.sup.2; R.sup.Y is selected from the group consisting of R.sup.III and R.sup.2; R.sup.C is the binding site of a single bond linking the first chemical moiety to the second chemical moiety; R.sup.III is selected from the group consisting of CN and CF.sub.3; Q is at each occurrence independently from each other selected form the group consisting of N and CR.sup.III; R.sup.Tz is at each occurrence independently from 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; C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.1 is at each occurrence independently from 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, which is optionally substituted with one or more substituents selected from the group consisting of: deuterium, C.sub.1-C.sub.5-alkyl and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; R.sup.2 is at each occurrence independently from 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, which is optionally substituted with one or more substituents selected from the group consisting of: deuterium, C.sub.1-C.sub.5-alkyl and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; R.sup.I is 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; C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.II is 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; C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6; R.sup.a, R.sup.3 and R.sup.4 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, N(R.sup.6).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, 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, 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 another selected from the group consisting of hydrogen, deuterium, N(R.sup.6).sub.2, OR, 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 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, the substituents R.sup.a, R.sup.3, R.sup.4 or R.sup.5 independently from each other form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents R.sup.a, R.sup.3, R.sup.4 or R.sup.5; and wherein at least one ring member Q is N; at least one substituent selected from the group consisting of T, V, W, X and Y is R.sup.III, and at least one substituent selected from the group consisting of R.sup.T, R.sup.V, R.sup.W, R.sup.X and R.sup.Y is R.sup.III.

2. The organic molecule according to claim 1, wherein exactly one substituent j selected from the group consisting of T, V, W, X and Y is R.sup.III; and exactly one substituent is selected from the group consisting of R.sup.T, R.sup.V, R.sup.W, R.sup.X and R.sup.Y is R.sup.III.

3. The organic molecule according to claim 1, wherein R.sup.I, R.sup.II, R.sup.1 and R.sup.2 are at each occurrence independently from another selected from the group consisting of H, methyl, mesityl, tolyl and phenyl.

4. The organic molecule according to claim 1, wherein R.sup.III is CN.

5. The organic molecule according to claim 1, wherein the second chemical moiety comprises a structure of Formula IIa: ##STR00365##

6. The organic molecule according to claim 1, wherein the second chemical moiety comprises a structure of Formula IIb: ##STR00366## wherein R.sup.b is at each occurrence independently from another selected from the group consisting of: 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.2-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 the second chemical moiety comprises a structure of Formula IIc: ##STR00367## wherein R.sup.b is at each occurrence independently from another selected from the group consisting of 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, 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, 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.

8. The organic molecule according to claim 6, wherein independently from another, R.sup.b is 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.

9.-15. (canceled)

16. A composition comprising: (a) at least one organic molecule according to claim 1 as an emitter and/or a host; (b) one or more emitter and/or host materials different from the at least one organic molecule according to claim 1, and (c) optionally one or more dyes and/or one or more solvents.

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

18. The optoelectronic device according to claim 17, wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

19. The optoelectronic device according to claim 18, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is disposed on the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

20. An optoelectronic device comprising the organic molecule according to claim 1, wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.

21. An optoelectronic device comprising the organic molecule according to claim 5, wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

22. The optoelectronic device according to claim 21, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is applied to the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

23. An optoelectronic device comprising the composition according to claim 16.

24. The optoelectronic device according to claim 23, wherein the optoelectronic device is an organic light-emitting diode, light-emitting electrochemical cell, organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

25. The optoelectronic device according to claim 24, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is disposed on the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the composition.

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

27. A process for producing an optoelectronic device, comprising processing of the composition according to claim 16 by a vacuum evaporation method or from a solution.

Description

EXAMPLES

[0430] General Synthesis Scheme I

##STR00036##

[0431] General Procedure for Synthesis AAV1:

##STR00037##

[0432] 3,5-dichloro-4-fluorophenyl boronic ester (1.00 equivalents; CAS 1092485-88-5), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.1 equivalents), Pd(dppf).sub.2Cl.sub.2 (0.05 equivalent), and potassium acetate (3.00 equivalents) are stirred under nitrogen atmosphere in a THF/water mixture (ratio of 10:1) at 80 C. for 20 h. The cooled mixture is poured into brine, the precipitated product is filtered off and washed with water and cold ethanol. The product E1-1 is obtained as a solid.

[0433] General Procedure for Synthesis AAV2:

##STR00038##

[0434] The synthesis of E1-2 is done analogously to AAV1 exce-2,6-diphenyl-1,3-pyrimidine is used instead of 2-chloro-4,6-diphenyl-1,3,5-tria 3,5-dichloro-4-fluorophenyl boronic ester (1.00 equivalents; CAS 1092485-88-5), 4-chloro-2,6-diphenyl-1,3-pyrimidine (1.1 equivalents), Pd(dppf).sub.2Cl.sub.2 (0.05 equivalent), and potassium acetate (3.00 equivalents) are stirred under nitrogen atmosphere in a THF/water mixture (ratio of 10:1) at 80 C. for 20 h. Active carbon and Celite are added to the reaction mixture and stirred at 80 C. for 10 min, then the mixture is hot filtered and the organic phase is concentrated under reduced pressure. The residue is dissolved in dichloromethane and washed with water.

[0435] After concentrating the organic phase under reduced pressure the residue is washed with hot ethanol. The product E1-2 is obtained a solid.

[0436] General Procedure for Synthesis AAV3:

##STR00039##

[0437] The synthesis of E1-3 is done analogously to AAV2 except that 2-chloro-4,6-diphenyl-1,3-pyrimidine is used instead of 4-chloro-2,6-diphenyl-1,3-pyrimidine.

[0438] General Procedure for Synthesis AAV4-1:

##STR00040##

[0439] E1-1 (1.00 equivalents), the corresponding cyanophenylboronic acid E1-4 (2.2 equivalents), Pd.sub.2(dba).sub.3 (0.02 equivalent), XPhos (0.08 equivalents) and potassium acetate (3.00 equivalents) are stirred under nitrogen atmosphere in a dioxane/water mixture (ratio of 10:1) at 80 C. for 20 h. Active carbon and Celite are added to the reaction mixture and stirred at 80 C. for 10 min, the mixture is hot filtered and the residue is washed with dioxane. The organic phase is concentrated under reduced pressure, the residue is dissolved in dichloromethane and washed with water. After concentrating the organic phase under reduced pressure, the residue is washed with hot ethanol. The product Z1 is obtained a solid.

[0440] General Procedure for Synthesis AAV4-2:

##STR00041##

[0441] E1-2 (1.00 equivalents), the corresponding cyanophenylboronic acid E1-4 (2.2 equivalents), Pd.sub.2(dba).sub.3 (0.02 equivalent), XPhos (0.08 equivalents) and potassium acetate (3.00 equivalents) are stirred under nitrogen atmosphere in a dioxane/water mixture (ratio of 10:1) at 80 C. for 20 h. The reaction mixture is poured in brine, the precipitated product is filtered and washed with water, ethanol and hot dichloromethane. The product Z2 is obtained as a solid.

[0442] General Procedure for Synthesis AAV4-3:

##STR00042##

[0443] The synthesis of Z3 is done analogously to AAV4-2 except that E1-3 is used instead of E1-2.

[0444] General Procedure for Synthesis AAV5:

##STR00043##

[0445] The synthesis of Z4 is done analogously to AAV4-1, AAV4-2 or AAV4-3 except that the corresponding trifluoromethylphenylboronic acid E1-5 is used instead of E1-4. Alternatively, the corresponding trifluoromethylphenylboronic acid pinacol ester or a similar boronic acid ester can be used.

[0446] General Procedure for Synthesis AAV6:

##STR00044##

[0447] The synthesis of Z5 is done analogously to AAV5 except that the corresponding bis(trifluoromethyl)phenylboronic acid E1-6 is used instead of E1-5. Alternatively, the corresponding bis(trifluoromethyl)phenylboronic acid pinacol ester or a similar boronic acid ester can be used.

[0448] General Procedure for Synthesis AAV7:

##STR00045##

[0449] The synthesis of Z6 is done analogously to AAV5 except that the corresponding bis(cyano)phenylboronic acid ester, in particular bis(cyano)phenylboronic acid pinacol ester, E1-7 is used instead of E1-6

[0450] General Procedure for Synthesis AAV8:

##STR00046## ##STR00047## ##STR00048##

[0451] Z1, Z2, Z3, Z4, Z5, or Z6 (1 equivalent each), the corresponding donor molecule D-H (1.50 equivalents) and tribasic potassium phosphate (4.20 equivalents) are suspended under nitrogen atmosphere in DMSO and stirred at 120 C. (20 h). Subsequently the reaction mixture is poured into a saturated sodium chloride solution and the precipitate is filtered and washed with water. The solid is then dissolved in dichloromethane, dried over MgSO.sub.4 and the solvent is evaporated under reduced pressure. The crude product is purified by recrystallization out of ethanol or by flash chromatography. The product is obtained as a solid.

[0452] In particular, the donor molecule D-H is 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).

[0453] Exemplarily a halogen-substituted carbazole, particularly 3-bromocarbazole, can be used as D-H.

[0454] 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.

[0455] 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.

[0456] Cyclic Voltammetry

[0457] Cyclic voltammograms are measured from solutions having concentration of 10.sup.3 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/L of tetrabutylammonium hexafluorophosphate). The measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp.sub.2/FeCp.sub.2.sup.+ as internal standard. The HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).

[0458] Density Functional Theory Calculation

[0459] 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 a m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.

[0460] Photophysical Measurements

[0461] Sample pretreatment: Spin-coating

[0462] Apparatus: Spin150, SPS euro.

[0463] The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

[0464] Program: 1) 3 s at 400 U/min; 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.

[0465] Photoluminescence spectroscopy and TCSPC (Time-correlated single-photon counting) 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.

[0466] Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

[0467] Excitation Sources:

[0468] NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

[0469] NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

[0470] SpectraLED 310 (wavelength: 314 nm)

[0471] SpectraLED 355 (wavelength: 355 nm).

[0472] Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.

[0473] Photoluminescence Quantum Yield Measurements

[0474] 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.

[0475] Emission maxima are given in nm, quantum yields in % and CIE coordinates as x,y values. PLQY is determined using the following protocol: [0476] 1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference [0477] 2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength [0478] 3) Measurement [0479] Quantum yields are measured for sample of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

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

[0480] wherein n.sub.photon denotes the photon count and Int. the intensity.

[0481] Production and Characterization of Optoelectronic Devices

[0482] OLED devices comprising 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%.

[0483] 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. Accelerated lifetime measurements are performed (e.g. applying increased current densities). Exemplarily LT80 values at 500 cd/m.sup.2 are determined using the following equation:

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

[0484] wherein L.sub.0 denotes the initial luminance at the applied current density.

[0485] The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.

[0486] HPLC-MS:

[0487] HPLC-MS spectroscopy is performed on a HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL). A reverse phase column 4.6 mm150 mm, particle size 5.0 m from Waters (without pre-column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) with the solvents acetonitrile water and THF in the following concentrations:

TABLE-US-00001 solvent A: H.sub.2O (90%) MeCN (10%) solvent B: H.sub.2O (10%) MeCN (90%) solvent C: THF (100%)

[0488] From a solution with a concentration of 0.5 mg/ml an injection volume of 15 L is taken for the measurements. The following gradient is used:

TABLE-US-00002 Flow rate [ml/min] time [min] A[%] B[%] D[%] 3 0 40 50 10 3 10 10 15 75 3 16 10 15 75 3 16.01 40 50 10 3 20 40 50 10

[0489] Ionisation of the probe is performed by APCI (atmospheric pressure chemical ionization).

Example 1

[0490] ##STR00049##

[0491] Example 1 was synthesized according to AAV1 (yield 85%),

[0492] AAV4-1 (yield 63%) wherein 2-cyanophenylboronic acid was used as reactant, and AAV8 (yield 95%).

[0493] HPLC: Retention time 17.7 min, 97.8%

[0494] FIG. 1 depicts the emission spectrum of example 1 (10% by weight in PMMA). The emission maximum (.sub.max) is at 460 nm. The photoluminescence quantum yield (PLQY) is 71%, the full width at half maximum (FWHM) is 0.46 eV and the emission lifetime is 32 s. The resulting CIE.sub.x coordinate is determined at 0.16 and the CIE.sub.y coordinate at 0.19.

Example 2

[0495] ##STR00050##

[0496] Example 2 was synthesized according to AAV2 (yield 82%),

[0497] AAV4-2 (yield 78%) wherein 3-cyanophenylboronic acid was used as reactant, and AAV8 (yield 87%).

[0498] HPLC: Retention time 17.9 min, 96.8%

[0499] FIG. 2 depicts the emission spectrum of example 2 (10% by weight in PMMA). The emission maximum (.sub.max) is at 441 nm. The photoluminescence quantum yield (PLQY) is 44%, the full width at half maximum (FWHM) is 0.45 eV and the emission lifetime is 42 s. The resulting CIE.sub.x coordinate is determined at 0.15 and the CIE.sub.y coordinate at 0.10.

Example 3

[0500] ##STR00051##

[0501] Example 3 was synthesized according to AAV1 (yield 85%),

[0502] AAV4-1 (yield 69%) wherein 4-cyanophenylboronic acid, pinacol ester (CAS 171364-82-2) was used instead of reactant E1-4, and AAV8 (yield 19%).

[0503] HPLC: Retention time 10.3 min, 98.0%

[0504] FIG. 3 depicts the emission spectrum of example 3 (10% by weight in PMMA). The emission maximum (.sub.max) is at 465 nm. The photoluminescence quantum yield (PLQY) is 81%, the full width at half maximum (FWHM) is 0.44 eV and the emission lifetime is 51 s. The resulting CIE.sub.x coordinate is determined at 0.16 and the CIE.sub.y coordinate at 0.20.

Example D1

[0505] Example 3 was tested in the OLED D1, which was fabricated with the following layer structure:

TABLE-US-00003 Layer Thickness D1 10 100 nm Al 9 2 nm Liq 8 20 nm NBPhen 7 10 nm MAT1 6 50 nm Example 3 (20%): mCBP (80%) 5 10 nm mCBP 4 10 nm TCTA 3 40 nm NPB 2 5 nm HAT-CN 1 50 nm ITO Substrate glass [00052]

[0506] Device D1 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 12.7%. The emission maximum is at 472 nm with a FWHM of 73 nm at 7.6 V. The corresponding CIEx value is 0.15 and CIEy is 0.23.

[0507] Additional Examples of Organic Molecules of the Invention

##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##

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##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##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##

FIGURES

[0508] FIG. 1 Emission spectrum of example 1 (10% by weight) in PMMA.

[0509] FIG. 2 Emission spectrum of example 2 (10% by weight) in PMMA.

[0510] FIG. 3 Emission spectrum of example 3 (10% by weight) in PMMA.